The Power of Innovation: Chris Denson

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“Now, as you know from listening to this here podcast, Chris Denson really loves innovation.” This line opens every episode of the Innovation Crush podcast hosted by Chris Denson, a self-proclaimed innovation fanatic and expert, global marketer, Director of Omnicom Media Group’s Ignition Factory, author, and speaker. Denson has built a bustling career off creativity, ingenuity, successful collaboration, and seeking out new and exciting ideas that will change the world. Denson stopped by Loeb NYC to discuss his book, the secrets of his success, his journey from stand-up to business, the magic of the creative process, and much more.

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This post centers on the key takeaways from Chris Denson’s wildly informative and entertaining interview with Katie Loeb, Director of Strategy and Innovation, as well as on his life as an exciting and cutting-edge creative. The key points include:

It’s okay to bomb: The importance of trying and trying and then trying again. Denson discusses his early experiences in stand-up comedy and how that helped erase the fear of failure.
Thinking outside and all around the box: How diversity of thought enhances the creative process and ensures that a finished product has more staying power.

Don’t be afraid to dive in: Denson urges innovators to fully immerse themselves in whatever field they pursue in order to enhance the quality of services or products.

Always empathy: Empathy is a matter of business. Empathy is about playing both roles of innovator and consumer. (He has this approach in common with Dr. Helen Rothberg).

Knowledge is power: The wealth of knowledge knows no limits. Know enough to be dangerous. Know enough to have intelligent conversations and be open to learning more.

Denson’s book is titled “Crushing the Box, 10 Essential Rules for Breaking Essential Rules.” The book includes such chapters as “Kick Some Balls,” “Ruin Everything,” and “Eat Your Brain,” a far cry from traditional snippets of advice one would expect to find inside a fortune cookie promising a future of success. Denson wants to step way outside of the box, where innovation, collaboration, and creativity intersect and create opportunities for breakthroughs. “Crushing the Box” challenges the limitations of rules and encourages readers to not fear going against the grain in order to pursue their dreams.

Chris Denson book
“Crushing the Box” by Chris Denson

Meet the Man Behind the Mission

Chris Denson was born in Detroit, Michigan to Christine Denson, a school teacher, and John Denson, a theologian. Denson was an active student at his high school in Lathrup Village, Michigan. He took part in the marching band, swim team, track and field, and golf. He later went on to attend Michigan State University where he dabbled in martial arts and comedy as he earned a degree in packaging engineering. His early enthusiasm and curiosity for life would follow him throughout his career and lead him on a varied and colorful journey through business, stopping off—if only briefly—at Loeb NYC along the way for our regular Speaker Series.

From Comedy to Business

Denson first got into comedy while still a student at Michigan State. He describes his first stand-up experience much like being tossed into water without knowing how to swim. His first time doing stand-up was an audition to open for a Cedric the Entertainer show on campus – a gig he landed. This led him to pursue performing as many shows as possible, winning comedy competitions, and eventually moving to Los Angeles after he realized engineering was not for him. Denson’s experience in the entertainment industry goes far beyond the comedy stage alone. He has worked both on screen and behind the scenes for Paramount, BET, Playboy Television, Machinima, the American Film Institute’s Digital Content Lab, and has served on advisory boards for the likes of SXSW and Pluto TV.

Denson sees stand-up comedy as the pursuit of universal life truths delivered with a unique perspective. He notes the progression of his comedy style, moving away from first doing what he thought was funny to incorporating more about his personal life and finding humor in the otherwise mundane. The lessons learned from doing stand-up have evidently carried over into Denson’s successful transition into business, a venture that is still very much alive and growing. When discussing the nature of stand-up, he notes that the entire operation is a “you-endeavour.” Once you are up on stage, all that you have is yourself, your personality, and your perspective. The spotlight is narrow. He offers a protracted, thoughtful “It’s…literally…just you.” Perhaps Denson’s ability to hold his own in a multitude of fields stems from first learning how to be comfortable on stage with only himself as a resource.

Diversity of Thought

The first chapter Denson and Loeb discuss is “Put Women in Their Place,” a title he calls a double entendre mixed with a little bit of intended shock value. Denson’s call for a more level playing field in business involves erasing unconscious bias that seems to perpetuate discrimination. He discusses working with such esteemed women in business like Linda Boff (CMO at GE for the last fourteen years) without expecting an applause for encouraging diversity in a male-dominated field. For Denson, diversity should be natural, easy, expected, and absolutely essential for success.

What Denson calls “diversity of thought” is the inclusion of all different perspectives. He wants a TV writer, a photographer, and a scientist all in one brainstorming room in order to bring all different kinds of experiences, points of view, attributes, and skills together. He calls it the spirit of curiosity. For Denson, the creative process is dynamic, fruitful, nimble, and requires voices other than one’s own so as to avoid a stagnant echo chamber of one’s own thoughts. Innovation is about exploring outside the box, and then “Crushing” it after.

Denson also practices what he preaches. He discusses working with and learning from the likes of Dan Goods (Visual Strategist for NASA) and Bruce Duncan (a psychologist who works with the sentient robot BINA48). He has interviewed hundreds of innovators on Innovation Crush, including FUBU owner and Shark Tank investor Daymond John, writer, and producer Dan Harmon, musician Damian Kulash, entrepreneur Krizstina Holly, skateboarder Rob Dyrdek, and rapper Chamillionaire. For Denson, the pursuit of knowledge is endless.

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Chris Denson and Dan Harmon (Innovation Crush podcast #100 — “Revenge of the Nerd”)

Swim Like an Otter

Another key factor to Denson’s success is empathy. The chapter, “Swim Like an Otter,” was inspired by NASA artist’s Dan Goods’ experience in art school. One day, an art professor told Goods to draw a picture of an otter. He then told the young artist to meet him at the pool the next day. When Goods arrived, the professor said “now get in the water and swim like one.” How does this relate to business? For Denson, empathy is essential to success. He encourages innovators and marketers to strive for the deepest sense of empathy in order to provide quality services or products. “Go there. Be a part of the community,” he urges. Swimming like an otter is about fully immersing oneself in the pursuit at hand, with empathy always the Northstar.

Sometimes swimming like an otter requires less action and more observation. He discusses the business strategy of Starbucks, a brand name that has become almost synonymous with coffee itself. Starbucks incorporates an eleven week period in which C-level executives go to different stores, travel the world, and observe the ways in which different demographics experience the massive coffee chain at the ground level. Empathy is a matter of business. Denson stresses the importance of narrowing in on the day-to-day experience of a company, service, or product. He says that if one works for Nascar, go to the races. Stand in the lines. Experience the debris flying off the track. He urges: “Discover pain points that you can actually solve for that specific group.” Empathy in business is about playing both roles of innovator and consumer.

Know Enough to be Dangerous

Another role that his book encourages is that of a mercenary. The chapter, “Become a Mercenary,” is inspired by the quote “know enough to be dangerous.” Denson credits this mindset for his ability to interact with experts in their fields (the Linda Boffs and Bruce Duncans of the world) without necessarily being an expert himself. Denson speaks of an acrobatic ability to confidently mingle in various different fields with something of an omnipotent command over the conversation. Perhaps confidence comes from an undying willingness to learn, the spirit of curiosity that motivates much of his work.

Should we all become generalists? Denson says no. “Knowing enough to be dangerous” is about being able to have intelligent conversations that open the door for more potential collaboration and learning. For Denson, an innovator does not need to be a psychologist, an astrophysicist, an expert coder, and world-renowned pianist all rolled into one. Curiosity and the willingness to learn along the way will grant one access to a wealth of knowledge. Denson wants to expand the scope of experience, both in business and beyond.

Heart First

Finally, Denson leaves Loeb NYC with a story of one of his most impressive friends, one who lives with severe disabilities. He lists his friend’s various impressive accomplishments: he’s a documentarian, has a PhD from Stanford, and was an ambassador for President Obama for persons with disabilities. Denson speaks of the extensive trips he has taken with his friend in Kenya and notes the hardships his friend encounters on a day-to-day basis. However, his friend does not quit, “all because he wants to make the world a better place for people like him.” Empathy for others is what motivates such incredible efforts. Denson calls it working with your “heart first.”

So why should we break the rules? For Chris Denson, breaking the rules allows for such incredible breakthroughs that his friend exhibits. As his book states, breaking the rules is how Grace Hopper invented the first computer; how George Lucas brought Star Wars to life; how Chris Denson became an innovative extraordinaire.

Early in the interview, Denson jokes that his mother had always envisioned her son walking to work with a briefcase and a three-piece suit. Denson thought outside the box – and then crushed it.

Dr. Helen Rothberg: From Bartender to Business Badass

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As one of Loeb Enterprises‘ paid summer interns, I appreciate the value that their weekly Speaker Series brings to the Internship Program. It elevates the internship experience from being purely transactional to being actively enriching and growth-oriented. 

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Interns Climbing the Career Ladder

Throughout the summer, we have had the privilege of learning from an array of people ranging from the experienced angel investor Brian Cohen to the director of strategy and operations at 3×3 Insights, Noah Friedman. Most speakers discussed their personal experience in the realm of finance and various lessons that we could extract from their stories.

However, Dr. Helen Rothberg did something a little different. Dr. Rothberg’s talk followed the theme of her book, The Perfect Mixwhich contains stories from her career as a New York City bartender and how those lessons have applications in the world of business (where she has achieved resounding success as a Competitor Intelligence Strategist and Intellectual Capital Manager). The book, as the author describes it, is “About leading yourself, because how can you lead anybody else if you can’t lead yourself?”

loeb nyc Speaker Series Helen Rothberg

This premise instantly drew in the audience since many people our age (college interns) have experience working in the hospitality industry, given its prevalence in high school employment.  We can relate to the thirst, struggle, and aspiration of working tough service jobs with the hope of “making it” in the world of entrepreneurship, startups, and business. Dr. Rothberg says, “If I were queen I would make everybody work in a restaurant or bar because that’s where you really get to understand how people work and human nature.”

Dr. Rothberg embodies the spirit of the Loeb NYC summer internship. A self-described “CUNY kid”,  she worked as a bartender throughout her academic career up until she received her Ph.D. From working as a consultant for many years and subsequently as a professor at the School of Management at Marist College, Dr. Rothberg is a model of adaptability, guts, and persistence. Especially in the face of rejection, and hearing “no”. 


Dr. Helen Rothberg’s book contains a cocktail at the end of each chapter which relates to that section’s theme. Her preference: vodka. But that’s not the only recipe she shares. Dr. Rothberg explains, “My book is about A.D.V.I.C.E. because bartenders give good advice. Action. Determination. Vision. Integrity. Communication. Empathy. Those are the ingredients that I think are essential to being able to lead yourself. Then I add to that two more things: Being who you really are, standing in your own shoes and not being afraid of change…because nothing stays the same.”


Taking Action: Do More. Say Less.

The concept of doing more and saying less is an extremely important life lesson in the digital age. Social media has fostered a culture of saying rather than doing, which has heavily influenced this generation. It is a valuable lesson, as it limits the times you over-promise and under-deliver. This is something that I am guilty of doing from time to time and is a pitfall a lot of eager young professionals and interns fall into as they attempt to create a good first impression.

It is always a lot more satisfying to not only be able to meet goals that you verbally set but also be able to exceed them. I don’t think I know a worse feeling than telling everyone about something that you are going to do or want to do only for it to be a public failure that everyone witnesses. It is much better to keep it to yourself only to acknowledge it when whatever you are working on is in development.

Dr. Rothberg refers to a time that she applied for a job at a bar that she had carefully researched (proximity to a police precinct, far from her prying PhD supervisors, an expensive menu for good tips), only to be told: “I don’t hire women bartenders.” And yet she persisted. “Showing what you can do is the best way to show what you can do. I offered to come in on their busiest night and work for free. And then they could decide whether I stay or not, I wouldn’t even take the tips. The lesson: Do more, say less. Be willing to show what you’re made of before you take for yourself. Because then you’re always going to get more…Think about how you can look at it differently.”

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Determination and Vision

For college students, earning a PhD is an intimidating prospect, but Dr, Rothberg put it in perspective. “Working on a PhD has nothing to do with intelligence it’s all persistence and humility.” It is true that it is easy to mistake intellect, cleverness, and smarts as the only keys to business success. Really the ability to stay focused, keep fighting the fight and having the patience to keep moving forward is sometimes underrated. Also underrated – civility.

In the race to succeed in school, business, whatever, it is easy to get distracted by competition and competitiveness. Dr. Rothberg advises, “Determination is about getting things done with ingenuity and civility. It’s about never stepping on someone else to make yourself look bigger. It’s about if you can’t get something done, figuring out a way to go around and get that done.” This attitude puts the focus back on yourself, rather than seeking blame, validation or comparison from outside sources. “Vision is about seeing what’s possible and sharing what you see with others.”

I and the other 39 summer interns for 2018 have been able to see that Michael Loeb, Rich Vogel, and Loeb NYC is a place of vision and innovation. It’s a quality that Dr. Rothberg noticed about us too. She said she has visited Fortune 500 companies and startups of all kinds, but that what we have at Loeb NYC is a buzz and energy that is hard to find elsewhere.

Something that Dr. Rothberg pointed out, which has been demonstrated by the startup portfolio companies I’ve worked with during my internship is that while a plan can be executed without a manager sharing their vision with their underlings, a great leader brings their team along and keeps them informed. “A good manager can get things done in the dark.  [But] you have to know what you’re selling. You have to know what you’re trying to create and you have to be able to share that with others…Have a vision for where you can take yourself, your company, your team, your community.”

Integrity: Always Tell the Truth

College interns are used to the concept of competition. Finding a quality, paid summer internship where you will be making an investment in your future, rather than just fetching coffee, involves competing with brilliant students from all over America. Especially in the case of coveted commercial internships in New York City. Some internship programs only take students from ivy league schools – which is a whole different battleground.

In this context, it is tempting to get caught up in fiction, drama, and politics. But Dr. Rothberg has some grounded, almost zen-like wisdom. She also espouses the value of taking risks, not being afraid to fail and being willing to learn from mistakes.

“Tell the truth. All the time. It’s not an option. Don’t play into drama and don’t create drama. But if you do play into drama, own it. None of us are perfect, and that’s what’s perfect. Failure can be your best opportunity to learn. You’ve got to embrace it and not be afraid. Some of us really begin to play it safe after a while because we’re afraid that we’re not going to live up to some image that someone has of us, or we’re not going to get it right. The best thing you can do is not be afraid and have the courage to try things. If it doesn’t work: own it as yours.”

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How to Communicate Better

One aspect of Dr. Rothberg’s Speaker Series talk that resonated with me was the idea of being a better communicator. It can be easy to assume people understand our intentions when we converse with them. However, communication extends way further than words alone. Adjusting body language and truly listening with the intent to learn rather than with the intent to respond is something that I am personally working on as I feel that it is an extremely important skill to learn.

Jason Blankfield, a Performance Coach, also touched upon this concept when he spoke to the interns at Internatopia. Internatopia is a feature of the Loeb Enterprises internship program. Michael Loeb describes it as “An entrepreneur boot camp comprised of programming developed by myself and other startup veterans to help prepare the students for their immersive summer experience.” Blankfield pointed out that we generally ask questions and instantly begin to think of how to reply to the answer we are given rather than truly listening to the answer and internalizing what it means and how it can be applied to our lives.

Sure, some questions and answers can be trivial, but one thing I am extremely guilty of doing is completely tuning out someone right after I ask them what their name is. I am horrible with names because I generally attempt to further the conversation rather than actually listening to the name the other person responds with. These kinds of miscommunications have significant implications in the business world. Better communication creates a situation where a manager is truly listening to the input of their team members. Effective communication is the foundation of a positive business relationship. Dr. Rothberg says, “The hardest thing to do is communicate in a way that what you really mean is received as you meant it.”

Cocktail for Success

In summation, Helen Rothberg challenged us to “Dare to care about yourselves, about your communities about the people around you. If you can do that you can lead yourself.” Her closing comments echoed another Speakers Series guest, Damian Woetzel, who told us “Live big, happy, lives”.  Rothberg’s version: “Lead yourselves to good, happy lives, to do good things for your companies, your community, your nation.” It must be significant that these themes unintentionally recur through Speakers Series.

From her engaging stories, relatable to college students and young professionals alike, to her vast knowledge of personal and professional advice, the hour Dr. Helen Rothberg spoke seemed like minutes.


Penrose Hill: Bringing Wine Into the 21st Century

Philip James is the founder and CEO of Penrose Hill – a wine company aiming to bring the wine industry into the 21st century. Click on the underlined text to jump to the section you want to read!:

1. Background on Penrose Hill their algorithm-based business model and the 3 branches driving growth.
2. Wine pairing advice from Penrose Hill CEO, Philip James.
3. Q&A with an entrepreneur: advice, startup breakthroughs.
4. Cheddar video interview (and transcript) with Philip James on Firstleaf wine club.

The use of data analytics means that Penrose Hill has gained unconventional perspectives into a somewhat conventional industry – to see wine differently and in ways that allow them to eliminate inefficiencies. James says his goal is to “provide consumers a better product for a better price”.

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Turning Data Into Wine

Data is at the heart of what Penrose Hill does. They use feedback from customers and partners to optimize every aspect of the winemaking process; from label design to flavor profile. As an independent winery, Penrose Hill eliminates the layers of middlemen between the producer and consumer, giving customers exclusive access to small-batch wines for less, while delivering higher margins to their partners.

Firstleaf Wine Club

There are three distinct branches driving Penrose Hill’s growth. The first and largest being the Firstleaf wine club. James says, “Penrose Hill wants to build the world’s most customer-centric wine company, and Firstleaf is our key to achieving that. Using a specially designed algorithm that combines machine learning and wine chemistry into an AI-based platform, we are able to match wines to customer’s tastes with unprecedented specificity. We’re constantly innovating new ways to please customers.”

Direct-to-trade Wines

The second branch driving Penrose Hill’s growth is a line of direct-to-trade wines. The company diversifies their sales base by venturing into the largest segment of the wine market: traditional, distributor-driven sales to retail and restaurants. Leveraging the savvy gleaned from market testing by Firstleaf, new packaging options and dynamic customer experiences allow them to “Breathe new life into this segment of the industry. We are introducing several new brands in 2018”. Canned wine Right Now Red no. 8 is already in some stores in New York, “it’s made to be enjoyed anywhere you are it is perfect for a busy city.” 

penrose hill quote we focus on making wines that our members love and that are incredibly high quality at a fair price

Another of their wines to look out for is Bodewell—a collaboration with the charity Wine to Water. The proceeds from the sales fund their mission to provide access to clean water to those who need it the most globally. For Bodewell, Penrose only sources from exciting and distinct wine regions, “in an effort to highlight our interconnectedness through the land.”

Corporate Partnerships

The third branch of Penrose Hill is corporate partnerships. They have been working to launch wine clubs and build labels for brands interested in diversifying client outreach, for example, a “really fun” Loeb NYC “family” partnership with the team from Thnks.  

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Wine Pairing Advice from Penrose Hill CEO, Philip James

Here is some practical wine pairing advice. In my opinion, wine pairings are all dependent on what you are eating and what you like, but here are a few quick tips that may help lift any meal or dinner party. The most important “rule” is to have fun and drink what you like, there are no hard-and-fast rules when it comes to pairing wine! That said, here are a few typical recommendations:

● Start with something sparkling! Champagne is often saved for toasts, but sparkling wines deserve a place at any dinner table, as they pair well with nearly all foods. Our Clarabelle Sparkling Wine was a club favorite this past holiday season.

● For whites, we love anything with higher acidity. Acidity allows a wine to highlight and mix with the food’s flavors. Our Play Riesling is a great option for such a meal.

● If you prefer reds, I’d suggest a Pinot Noir, like our Cassiday Blare, or a medium-bodied blend. You want wines with the fruit and acidity to stand up to a meal with a lot of different flavors present.

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Interview with an Entrepreneur – Philip James Takes Our Questions

What are Penrose Hill’s goals?

I’ve been in the wine business for almost 15 years and have started several companies. With every iteration, I’ve grown more and more focused on delivering quality and value to the end customer. With Penrose Hill, we focus on making wines that our members love and that are incredibly high quality at a fair price. We want to offer the best of both worlds (quality and fair pricing) because we believe it can be done.

Why did you choose to work with Loeb NYC?

In 2015, while raising our seed round of funding, Primary Ventures introduced me to Michael Loeb and Rich Vogel as people who could give expert insight into running a successful direct to consumer business. Our first meeting was in the construction site of what is now the “rainforest” floor of Loeb NYC.

One of the things that drew me to Michael is his ability to perceive customer pain points and inefficiencies and work to find a way to fix them. Loeb has a proven track record of success with subscription economics and consumer-focused goods, and we feel incredibly fortunate to be working with Loeb Enterprises.

What has been your startup breakthrough?

There have been a few notable breakthroughs at Penrose Hill. Most recently, it has been focusing on offering even more robust services to our customers. We grew our Member Experience team from 2 to 15 employees in the last 12 months, and are starting to offer more ways to buy and enjoy our wines. Very soon we will be launching our online store and selling wines by the bottle.  Our members will be able to easily reorder wines or order a gift for someone else. It will also allow prospective members the opportunity to try out our award winning wines before joining the club!

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Cheddar Interviews Penrose Hill

Watch Cheddar’s video interview of Philip James, Penrose Hill CEO. Cheddar asks about how Firstleaf differs from its competitors, Philip’s background in computational chemistry and how Firstleaf uses an algorithm to match subscriber’s taste preferences.

Penrose Hill’s algorithm is able to ascertain on a chemical level what an individual likes or doesn’t like about the wines they try. The algorithm also adapts when a person’s taste changes.

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Cheddar Video Transcript:


[Edited for clarity]

Cheddar: Philip, Firstleaf is not the only wine subscription service on the market. So what makes you different from the others?

Philip: There are a lot of places to buy wine. You want to set up two things. You want to make sure that the place you buy from has very good wine, and then you also need someone or a service to help pinpoint which of the wines is right for you. And I think we do both those things very well. We have a very talented team, a very good wine, but our algorithm also helps us figure out the perfect wine for you.

C: You’ve got a very interesting background to be able to successfully do this. A Master’s degree in Computational Chemistry and Business at both Oxford and Columbia. Tell us what that means for the service that you provide?

P: I have an undergraduate degree in chemistry and then I have a Master’s thesis in the mathematical modeling of chemicals. I don’t actually build the algorithm, we have a data science team that does it, and they are much smarter than I am. So my hope is that I’m the one who can help set the goals, and they’re the ones who have to go build the algorithm.

C: I know the Sommelier tests are incredibly difficult to do. How does that background that you have maybe help with your understanding of how to pair flavors together and to suggest flavors to your customers?

penrose hill quote when someone says, “I didn’t like this wine, I liked that wine” to be able to understand chemically what it is about those wines that they like.

P: I think having a science and math background is helpful. I mean, the service we have created – like I said, having great wine is like table stakes, you have a start there, but having an understanding at the chemical level of what’s in that wine, and maybe there’s someone who doesn’t like tannin, or you know, like acidity and they don’t like the feel or it gives them a stomach ache or whatever it is, being able to use the algorithm. So when someone says, “I didn’t like this wine, I liked that wine” to be able to understand chemically what it is about those wines that they like and then we can go recommend a fourth or fifth wine, based on –

C: – You apply it to everything in your catalog.

P: Yes, that’s right.

C: There are two different types of wino’s out there, there’s the ones that are consumers and the ones that think they’re connoisseurs but really they are just consumers, and then there’s – well, there’s perhaps three, there’s the ones who are actually the really good connoisseurs. How do you make sure that the ones who are the consumers and the ones who are the connoisseurs who are really just consumers, how do you make sure that you’re maturing their tastes and diversifying their experience in the right way as they do go along this process and the algorithm arguably will stay the same but match them up with something new as they go along?

penrose hill quote wine has acid right, but what kind of acid? There’s citric acid and malic acid, right. You have to get down to a really deep level

P:   I think this is something we actually do really well, right. So your tastes change and they might change just stylistically in the summer you’re going to BBQ a lot and maybe you’re going to be outside and you want rosé or maybe with the heavy meats that you BBQ you’re going to want big red wines or maybe you got on a health kick and now you want a different kind of a wine because you’re having lighter food. The algorithm is constantly updating. It’s kind of like Pandora for wine, so you don’t just stay at the seed song that creates the station, but as you rate songs the radio changes over time and so for us as you rate wines up or down, as you give us reviews, humans read them and the computers process it and it is continually updating as your tastes evolve.

H: Yeah, I love that analogy a lot. Speaking of kind of Pandora, one of the benefits of using Pandora is that they have a lot of data on you and what you like. What about on the supply side, we talk a lot about big data with our other guests, big data in healthcare and obviously in social, is there data in the wine industry? Are wineries getting more, I don’t know, sensors, uploading more of that information into a service like yours to make it easier for you to select the wines and to offer it to customers?

P: There is a lot of data, so our head winemaker has a masters in oenology and a masters in chemistry as well, and I talked about our data science team, and that’s led by a guy with a PhD in Chemistry so there is a strong, so we have a strong focus on the wine and the chemistry of the wine. We take a lot of chemical analysis of the wine. So wine has acid right, but what kind of acid? There’s citric acid and malic acid, right. You have to get down to a really deep level. Some of that comes from the wineries that we work with and some of that is our own chemical testing then all of that gets fed into a database along with customer ratings.

Penrose Hill quote You want to make sure that the place you buy from has very good wine, and then you also need someone or a service to help pinpoint which of the wines is right for you.

H: How many of these databases are out there for wine? Is there like a central one? Or like an open source?

P: No.

H: How do you guys all work together, then? I find it fascinating.

P: There is no universal, centralized, like rating system or information about wine like that, not at that level. So wines that we are making or wines that we are buying we have to run the chemistry on them and we have to take that data and we work with wine laboratories in California to do that.

H: Is that where the highest concentration of the wineries that you work with are? In California?

P: Yes, about half the wine that we sell is from California and the other half is from the rest of the world. Our facilities, our production, and shipping, our winemakers are in California.

H: And how much does your service cost?

P: We sell an introductory box of 3 wines for $15 and we lose money on that, but the idea is that’s what gets the algorithm going, it seeds it for us and then thereafter, shipment is 6 bottles and it’s $79 plus shipping.

H: Philip James, CEO of Firstleaf joining us here today on set – very interesting stuff.

Block Or Not?

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As marketers, we’re constantly being inundated with the next big marketing tactic. We’re lured in by the promise of reach, potential, relevance and the ever-elusive “cool factor” to capture the slippery attention of our evolving audience. We are duped into believing that without the latest technology or platform, our products will lack impact and lose importance. Our entire careers are now determined by our ability to leverage bleeding edge tactics (and often times, gimmicks) so that we can sell our brands, and keep our jobs. Of course, none of this is mandated.

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Marketing Tactics That Work

I hear my dad, Michael Loeb, say all the time that the same marketing tactics that worked in the Mad Men era still work today, it’s just the format that marketers need to adjust to. Meaning, the conversations, the segmentation, the communication has not changed, and never will. What will change is where those conversations take place, how we segment users, how the communication looks. The advent of data and technology has spurred this pivot, but any good marketer will be experienced enough not to panic in the face of these changes – rather, keen to learn how they could benefit from them.

This is a fine line that only few can tread. Marketers are destined to the overwhelming fate of sifting through too-many flashy options and having others tell them what is right for their own brands, making it impossible to distinguish the real from the fluff. Which is why Loeb NYC paired up with our partner and friend Bonin Bough to offer a course-correction opportunity through our event series, The Or Not Experience.

The Or Not Experience

The series is designed to focus on the trendiest marketing tactics, the ones shrouded in pomp and frill, in order to demystify them for brand marketers, creating a safe space where they can ask the questions they may have been too intimidated to ask in a formal setting. This year’s subject: Blockchain. The title? Block Or Not.

The audience was split between Brand Marketers and crypto pioneers – two groups who have rarely ever overlapped, now together bonding under one roof. The idea was to bring together these two dichotomous camps to have conversations about how one can benefit from the other and more importantly introduce themselves and their missions in a setting where they can let down their guard.loeb nyc quote block or not marketing experience We expected a few connections to be made. We thought a couple of follow up meetings would be scheduled. But in reality, we were stunned by the results. We saw meaningful relationships form and deals born. I’ve even watched partnerships germinate between entities in our own portfolio and some of the blockchain networks we met. Collaborations and new career paths were forged that day – all out of the simple necessity for honest and accurate information.

For that reason, The Or Not Experience is becoming a staple event marketing brand between Loeb NYC and Bonin ventures. Each year, we plan to host dinners and activations at major conferences like SXSW and CES, and of course, our curate our own flagship event in Southampton, NY. And while each year the theme will change, the requirement for empowerment via information will never change. As we’ve already seen, the juice is worth the squeeze.

What Did The Experts Say About Blockchain?

Babs Rangaiah, Exec. Partner, Global Marketing, IBM:

“Blockchain is going to be a truly transformative technology. In fact, our CEO [Ginni Rometty] said that blockchain will do for transactions what the internet did for communications. Think about how big of a statement that is.”

Ryan Singer, Co-Founder, President Chia Network Inc.:

“I’ve been surprised by the utopianism” around blockchain technology. They’re taking a technology that very much was broken in a different industry and pretending it can fix the things that are broken in their industry, just because they’re looking for an opportunity to change.”

Douglas Rushkoff, Media Theorist:

“My main message is the blockchain a lot of them are wishing on, it’s not only that it’s a pyramid scheme that is going to crash for 99% of the people who are involved in it, it’s not just that. I would say 0.1% of the applications that people are envisioning for blockchain could actually work.”

Sam Cassatt, Chief Strategy Officer, Consensys:

“What is really is, is a new type of trusted database technology, that can allow parties that don’t trust each other to share the same source of information.”

“This is like a global computer that’s trustable because no one owns it.”

Does Blockchain Technology Fit with Your Brand and Marketing?

Shelly Palmer, CEO Palmer Group:

“Blockchain technology is open source and free to use by any developer who is competent. What is not in any way commoditized is domain expertise. That’s what you bring to any project.”

Bob Lord, Chief Digital Officer, IBM:

“My objective was to have them specifically understand that blockchain can be a tool for marketers to use. But more importantly, how do you use blockchain technology to enhance your brand?” 

“With a trusted transaction system, I can create a value exchange with a customer in ways I’ve never been able to do before. I can get it down to their mobile devices, I can have it that one to one exchange which we all have been dreaming about.”

Loeb NYC Takes Cannes, 2018

This has been a year of many “firsts” for Loeb NYC. We hosted our first activation at SXSW, our first #BlockOrNot Experience in Southampton, and for the first time, Michael Loeb, Katie Loeb and Bonin Bough are attending Cannes Lions to represent Loeb NYC. Michael Loeb is speaking at a Brand Innovators event on Monday, June 18 (details below) and will be sharing ideas with the world’s best advertisers, innovators, and thinkers in the glamorous setting of the French Riviera.

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cannes, people walking and luxury cars in front of hotel intercontinental carlton
Cannes Carlton Hotel

What Happens in Cannes (Doesn’t Stay in Cannes)

June 18 – 22nd, 2018 marks the 65th Cannes Lions “International Festival of Creativity”. To win a prestigious Lion award is a feat coveted by elite agencies and the major players in “creative and marketing communications, entertainment, tech and design industries” the world over. To take home a Lion is a sign of greatness that resonates and creates ripples through various ad/tech echelons.

loeb nyc quote to take home a cannes lion is a sign of greatness

To give you an idea of the scope and grandeur of Cannes Lions, consider the numbers. This year, 16,000 attendees (28% of them members of the C-suite) from over 4,700 companies will converge on the pristine city to network, demonstrate their creative advancements and, essentially, show off their talents. The festival attracted 40,000+ entries in categories such as “health”, “reach”, “experience”, “craft” and importantly, “good” – as well as many others.

Legacy Cannes Lions participants admit that the event is not without its criticisms and issues (Too much peacocking! Too expensive!). However, despite facing critique, skepticism and philosophical questioning as to value and ROI, the festival has still seen an 22% increase in work submitted by in-house marketing teams over last year. Cannes still has the potential to elevate brands and generate powerful introductions.

Why is Loeb NYC Going to Cannes?

Many of the reasons why Loeb NYC decided to attend Cannes this year are elucidated in an insightful article by SummitSync (a Loeb NYC portfolio company), “Changing Tides: The Rise of Brands at Cannes.” As an aside, SummitSync’s razor-sharp platform “enables your team to shake more of the right hands to hit your meeting goals”. In other words, to get the most out of events and maximize lead generation.

Katie Loeb explains the benefits of participating in Cannes festival like this; “Cannes offers a style and propensity for deal flow in a way that other conferences are not able to. For us, it beautifully balances the business with the fun. We’re so excited about some of the connections we made and how they will affect our portfolio in the future.”

Loeb NYC is making moves this year and has planted its flag. Michael Loeb and Rich Vogel embarked on a decades-long, proverbial journey of one thousand miles, to conceive of and execute a company factory that grows businesses from idea, to seed, to growth-hacked company to market and potential exit. Loeb explains, “Our model – a self-funded Company Factory is unique. It’s what my partner, Rich Vogel, and I envisioned a decade ago when we concluded that for us Synapse was not the last chapter but the opportunity for a bold new one. What was then a germ of an idea is now burgeoning into full flower.”


Loeb NYC and Michael Loeb at Cannes Lions
Bonin Bough, Brand Innovator co-founder – Marc Sternberg and Michael Loeb


Our full-flower, unique, marketing and startup engine is ready for the big leagues. Not only that – we have some inspiration and inventive ideas of our own to demonstrate to the world. Does this sound like hype? You don’t have to take us at our word. Witness the Loeb effect in person.

Michael Loeb’s Speaking Engagements at Cannes

There is still time to register for the Brand Innovators event (Monday, June 18th), where Michael Loeb will be speaking. Details on the event can be found here.

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SummitSync has compiled a useful list of parties and events at Cannes Lions to get the most out of your time there (or to find out about what you might be missing).

If you are not going to be anywhere near France this weekend but would still like to hear a sample of what you can expect, watch this video of Michael Loeb and Bonin Bough at SXSW.

Loeb NYC Speaker Series: Damian Woetzel

loeb nyc logo green

On May 30, 2018, Damian Woetzel attended Loeb NYC’s Manhattan offices as the guest speaker for Loeb NYC’s recurring Speaker Series. Woetzel is a world-renowned ballet danseur and recently appointed Juilliard School President.

Ed McCabe, Executive Director at Loeb NYC, moderated a verbal “Pas De Deux” which led us through engaging topics such as; the effect of tech on the arts and arts accessibility, how to maximize creativity and ingenuity, and why New York City is especially fertile ground both for the arts, and for unique companies (like Loeb NYC) which operate in its midst.

This is a blog post about Damian Woetzel’s fascinating life and career, and how what he has learned as a dancer and proponent for arts education, applies to entrepreneurship and startup culture.

Ed McCabe, Damian Woetzel and Michael Loeb at Loeb NYC Speaker Series
Ed McCabe, Damian Woetzel and Michael Loeb at Loeb NYC Speaker Series

Damian Woetzel at Loeb NYC

Damian Woetzel grew up in Newton, MA. His father, Robert Kurt Woetzel, a professor of political science and international law, was born in China to German parents. At the conclusion of World War II, Robert Woetzel migrated to the United States. His experiences spurred an idealism that ensured that his sons, Jonathan and Damian, received a broad and deep cultural education. He wanted his sons to live “big lives”.

Woetzel’s mother, Sheila, brought Damian to an international and humanitarian perspective, building off of her life at UNICEF as a program officer based in four continents over the course of her career.

As young children, Damian Woetzel and his older brother took lessons in flute, guitar, martial arts, Chinese, athletics, and ballet (Woetzel started ballet lessons at 4 years old).

It was a time of in-betweeness both personally and for performing arts in america

This is not the narrative where an infantile wunderkind is introduced to an art-form and is instantaneously revealed to be a prodigy. Woetzel acknowledges he did not love ballet “right off the bat”, but does remember certain pivotal points that kept him on the path, for example, an enjoyment of music and his performance in a production of The Nutcracker as a 6-year-old in Boston, running around backstage and knowing every “nook and cranny like it was home”.

Woetzel shared a memory from the age of 12, sitting in the car with his brother, on their way back from their Sunday morning lessons. Jonathan said he would give up dance and continue learning Chinese. Damian wanted the opposite. These early choices reflected (or predicted) the future trajectory of both brothers’ “big lives”. Jonathan Woetzel earned a Ph.D in Asian studies and has been with McKinsey & Company in Shanghai since 1985.

Woetzel’s focus on ballet first “widened and then narrowed”. Initially, Woetzel learned and absorbed all he could about ballet: history, theory, and practice. Access to information was restricted to books that could be found on the subject, as well as the occasional film. Woetzel thirstily absorbed as much information as he could. The narrowing of focus, to a particular style and genre of dance, came later in New York City.

Big Leaps in the Big Apple

The site of Woetzel’s New York debut was the Joyce Theater, at age 18. He fondly describes the Joyce as “a revolutionary startup at work”. In Chelsea, 1985, the theater’s immediate surroundings were relatively barren, culturally speaking. The success of the Joyce’s creative engine attracted public grant investment and a rejuvenation of restaurants, community, and vibrancy to the area.

Woetzel’s performance reviews were good enough for Damian’s parents to approve his pursuit of ballet as a career path. As Woetzel puts it, this was a “time of in-betweenness”, both personally and for performing arts in America. Institutional titans like Carnegie hall had reached a zenith and were moving into a new phase. Icons like Bernstein and Balanchine passed away. A new type of performance was experiencing its adolescence. Jerome Robbins, one of the creative geniuses behind West Side Story, sponsored Woetzel’s career and created roles for him to perform at the New York City Ballet.

Damian Woetzel at Loeb NYC Speaker Series
Damian Woetzel at Loeb NYC Speaker Series

New York City is culturally speaking “the room where it happens” as Lin Manuel Miranda might agree. It has, Woetzel says, “a special foothold and a gravity that matters. So and so did that on this stage. It’s important”. Artists and giants leave their footprints here and their legacies echo through streets and stages. (See: “Loeb NYC Plants its Flag at SXSW” to find Michael Loeb’s perspective on “legacy”.) The “NYC” part of “Loeb NYC”, was selected because businesses can thrive in this dynamic and vivacious environment. Art dances with technology, technology elevates art.

As contemporary American ballet grew, so did Woetzel’s prowess and profile. Woetzel joined the NYCB in 1985. A principal dancer in his early 20s, a top-tier principal in his mid 20’s and an in-demand entity in his mid-to-late 20’s, he was invited to speak at conferences and attend forums.

Damian Woetzel quote: New York City has a special foothold and a gravity that matters

One such forum was a young leadership conference in China. Woetzel remembers sitting next to another young leader, Gabrielle Giffords, who was then a State Senator (the youngest elected to the Arizona Senate). At the age of 33, Woetzel was considering retirement from ballet and his next step (so to speak). Giffords suggested the Kennedy School Masters program at Harvard. Woetzel followed this lead. Woetzel has subsequently lectured at Harvard Law School, he says if he hadn’t been a danseur he might have been a lawyer.

Woetzel’s Second Act and Juilliard School

Having retired from ballet performance in 2008, Woetzel proceeded to “carve another life”. One of his enterprises has included directing the Vail International Dance Festival (marking its 30th anniversary this year) in Colorado. Woetzel describes the festival as a “creative engine and lab” where musicians and dancers can experiment but are also “exposed” and are not insulated from external review or critique. He has also acted as Director of Arts Programs at the Aspen Institute.

In late 2016, Woetzel received a call asking if he was interested in applying to become the 7th president of Juilliard. In May 2017, the application process culminated in Woetzel being offered the role. Woetzel anticipates that he will be able to combine the threads of his passions and experiences from “arts education to education writ large, the future of arts and arts and humanities”. Woetzel will still be involved with the Vail Festival, and will bring Juilliard there – the two will “feed each other”. Woetzel officially takes the helm in July 2018, and has spent the past year shadowing his admired predecessor, Joseph W. Polisi, who Woetzel describes as a “role model”.

Woetzel’s goal is for Juilliard to be an engine for innovative work (not dissimilar to his description of his early years at The Joyce Theater), for Juilliard to produce students who edge and push each other and for it to be an avant-garde incubator that upholds and advances its global reputation. This (realistic) idealism and expectation for Juilliard’s students echoes Woetzel’s own “live big lives” philosophy.

Loeb NYC CEO and founder, Michael Loeb, is a member of the Juilliard Board and supports Woetzel’s goals and ambitions for that institution. Loeb also believes in ‘giving back’ and actively contributing to NYC’s community and culture. For example, every Halloween, Michael Loeb opens his “haunted house” to the public. Thousands of guests attend at no charge. He was also honored by Build.NYC for his contributions to that organization. Loeb extols the virtuosity and talent of Juilliard students and recognizes the extremely high standard of work that the students perform at.

The “Edge Effect” and Advice for Young Entrepreneurs

Loeb NYC is home to many trailblazers and those with great aspirations. Woetzel is a person of diverse interests and curiosities. He mentions the “Edge Effect”, a concept he learned about from Yo-Yo Ma; “When two ecosystems meet, at the edge where they meet, you have the most diversity, and new life forms”. Incidentally, the floor where Loeb NYC resides was designed by Michael Loeb and Rich Vogel with a “rainforest” theme, because a rainforest represents the highest rate of growth and a diversity of species. The Edge Effect, Woetzel explains, is “where the spring meets the valley.” Where sections overlap and diverse elements are unified, that is where the richest invention is found. New York is one of those “edge” places: The home of hundreds of cultures and a city of contradictions.

In this fascinating video, Yo-Yo Ma explains the Edge Effect and gives the example of the Napa Valley.

Within Loeb NYC the “Edge” exists in many forms, for example, it is evident in the types of companies we are investing in and the industries in which they operate, from beauty to transport and health to the beverage industry, surprising symbiotic relationships and connections are revealed daily. Our staff has a wide range of backgrounds, talents, interests, and training. One thing they have in common is the “Entrepreneurs’ Gene.”

Woetzel’s advice to his students could equally apply to our young entrepreneurs: “Don’t separate the things that interest you” the overlapping of interest is a wellspring of invention. Take risks: “Be thoughtful about the level of risk you want to take… but I’m glad I took risks as a dancer” (Woetzel says he is lucky not to have suffered any major injuries through his career).

Tech and the City

The impact of the internet and technological developments on the arts has been, like on anything else, both positive and negative. Woetzel is interested in the “democratization of education and advancing opportunities for access to culture…to see Baryshnikov when he was young took effort.” Now access to information and digital content means that the gap has narrowed. Despite the screens we surround ourselves with, Woetzel also reminds us of an “appetite for experience” that transcends our virtual culture. In this vein, Vail performances are intentionally new and context specific. You can’t experience them anywhere else.

Before the internet age, one could only learn ballet “in the room” from a teacher, in a sort of oral tradition. Today, technical aids make the art-form more accessible, both to practitioners and to audiences. Woetzel observes technological advancements have “democratized choice on what is considered good”. But the shortening attention spans of the modern audience is an issue. “Taste is a valuable commodity and arbiters of taste are missing.” The glut of available opinions makes it harder to navigate between artistic trash and treasure.

Damian Woetzel quote don't separate the things that interest you

Dance is a beautiful form of communication and expression. Having the ability to be expressive and convey emotion wordlessly takes practice and dedication to achieve. This is a concept Loeb NYC’s marketing teams likely relate to, as we strive to seek ever-more effective methods of communicating messages and connecting with people.

The Loeb NYC Speaker Series has a few quirks and rituals, one of which is that our guests literally leave their mark by writing a message on one of the walls. Woetzel’s message to us is similar to what his parents’ might be… but with a sunny addition: “Happy big lives”.

Damian Woetzel Signature on Loeb NYC wall happy big lives
Damian Woetzel’s signature on a Loeb NYC wall

Loeb NYC Plants its Flag at SXSW

I was sitting on the stairs of a packed house in the middle of downtown Austin. The room filled with people, many of them the brightest minds at South by Southwest (SXSW). Brand marketers and influencers mingled with investors, founders, artists and everyone in between. Yet everyone’s attention was fixed on the front of the room, where entrepreneur and a good friend to Loeb NYC, Bonin Bough was moderating a fireside chat, between Gary Vaynerchuk (of Vayner Media) and my boss, Michael Loeb.

The discourse ricocheted between topics like the state of entrepreneurship, the blessing of “micro failures”, parenting techniques, and tombstone carvings. Prominently marked on banners throughout the room was the unmistakable logo of “Loeb NYC”, proudly displayed our brand to the world. Michael was captivating the audience,

“I want to prove Keats wrong. Keats said, our ‘names are writ on water’…The legacy I want to have is going to be enduring. I want somebody to point to me and say I learned something from that guy, or he built something for me, or he changed something, or he made things better.”

Loeb NYC quote I want to prove Keats wrong. Keats said, our ‘names are writ on water’…The legacy I want to have is going to be enduring
Michael Loeb on “Legacy”

Select founders and operators of Loeb NYC investment portfolio companies were dotted throughout the room, as were members of the Loeb NYC team itself. Given the size of the crowd, the room was remarkably silent. There was a palpable, powerful energy and excitement that manifested in an unmistakable buzz. It was at this very moment—when the nucleus of SXSW seemed to have converged within the “Loeb House”—that I realized I was witnessing a defining moment in the life-cycle of Loeb NYC. At this moment it became undeniably clear that we, Loeb NYC, had planted a flag and boldly announced to the world, “We are here. We’re here to play. And we’re here to stay.”

Loeb Enterprises has been operating for roughly ten years, and in that span has produced results many accelerators and incubators only dream of. Three companies, most notably, sit perched within the “trophy case”: Synapse Group, Priceline, and Script Relief, each of which have achieved storied status within its industry. Additionally, as of today, upwards of 15 companies operate within the greater Loeb NYC portfolio. So why did SXSW feel like a watershed moment for Loeb NYC? What had changed? Why did this moment, in the illustrious history of the company, feel different?

loeb nyc quote we are here we are here to play and we're here to stay

To answer those questions, let’s consider that simply put, the dynamics of media and consumer attention are going through tectonic shifts in style and technique. Past operating styles and methodologies will not cut it for firms that want to survive and thrive in 2018 and beyond. Those who want to be in the game and, more importantly, win are required to take a new tack, if prominence and reputation are at all important to them. For Loeb NYC, these things matter, not only for legacy, but for efficacy.

We believe that what we do day in and day out is special. There’s a magic inside the walls of Loeb HQ that allows us to view the world with optimism and the future with possibility. In the words of Katie Loeb, Director of Innovation at Loeb NYC and the mastermind behind our Austin event, our program at SXSW was an activation, a deliberate statement to the world of our presence and vision.  

The better one gets to know the man in charge, Michael Loeb, the clearer it is that his vision and ambition for Loeb NYC is massive.  In the words of Mr. Loeb himself, the vision for Loeb NYC is “What my partner, Rich Vogel, and I envisioned a decade ago when we concluded that for us Synapse was not the last chapter, but the opportunity for a bold new one.”

Bonin Bough, Michael Loeb and Gary Vaynerchuk at Loeb NYC's SXSW activation.
Bonin Bough, Michael Loeb and Gary Vaynerchuk at Loeb NYC’s SXSW activation.

This vision is clear and enticing. A company factory: vertically integrated company-building from an idea, to execution, to exit. The nomenclature is simple, it more or less describes the lifecycle of almost any successful startup investment. But in the case of Loeb NYC company-building, both the theory and practice are very different. Traditional venture capital firms and accelerators generally think of themselves as hotbeds for successful market disruptors and innovations. As places where exciting early-stage ventures blossom into unicorn companies with regularity. The reality is that it’s difficult to build a company – read Michael Loeb’s post, “The Entrepreneurs’ Gene” to see the proof from a man who has done it many times over. Most early-stage companies will fail, plain and simple.

So, how does one create a closed-ecosystem with better odds and better pathways to success for early-stage companies, at scale? From my perspective, the model at Loeb NYC achieves this by removing the constraint of constant-capital raising from founders and CEOs, so they can focus on running their companies. Providing back-office support and advice to the early-stage companies so that the headaches of administrative work are largely mitigated. We challenge the odds by offering portfolio companies access to expert teams of marketers so that they can quickly augment a small marketing with a larger, advisory one. A real sense of community means that companies can leverage each other’s networks and speedily earn credibility and connections with customers. Place this in a beautiful working space that can compete to attract talent with the best of ‘em. Add outstanding talent, commitment, and creativity to that mix and you have something special. We have this. We have it now. And at SXSW, we told the world.

magic inside walls at loeb nyc

Loeb NYC is a place where true talent can thrive and where meritocracy is honored and respected. Above all else, it is a place deeply passionate and committed to building successful enterprises across multiple industries. That is our foundation and inspiration. Walk around our offices at 712 Fifth Avenue and a clear sensation is realized of the kinetic energy and momentum present in this environment. Startups pack the floor, each targeting a different industry with intensity and drive. One common thread emerges; an undying commitment to results and growth. The aforementioned confluence of success-factors cannot be created overnight. It is possible through years of focus, merged with a willingness to test, experiment and iterate. You can feel it the moment you step off the elevator.

Mike Provance, the CEO of 3×3 Insights describes his company’s relationship with Loeb NYC in terms of a streamlined symbiosis:

“Our company is housed inside Loeb NYC, and we can’t go a day without spending time talking to Michael about what we’re doing. He’s very hands-on in the way that he engages with his portfolio companies and is constantly thinking of ideas that help us better execute on what we are trying to do, whether it’s sending emails any time of the day, or wandering through the Loeb NYC incubator, Michael is always available to us, as are his team of experts in various areas of marketing, of product development, direct mail, about anything you can think of he’s got some sort of experts who can support the efforts you’re trying to do.”

Personally, I have been in the Loeb orbit for the past three years or so. In that time I’ve seen expansion into two new floors in our midtown Manhattan headquarters, and a threefold growth in the size of our portfolio. Sitting on the stairs in that Austin house at SXSW, it’s apparent that the last ten years of innovation, company-building, and pure hard work have been leading up to this moment: a powerful declaration of our identity and intentions.

Our efforts at SXSW excited and encouraged me about what’s still to come. As the team returned home and settled back into our rhythm of operating and building, one resounding statement from our time at SXSW remained fixed at the front of my mind: We are just getting started.

Profits and Losses of Employee Appreciation

A company’s ability to retain talent often has consequences to its reputation and the quality of productivity and culture.  A 2013 Gallup survey report entitled, “How to Tackle U.S. Employees’ Stagnating Engagement” which studied almost 5 million employees, concluded that actively disengaged employees cost the United States economy $450 Billion – $550 Billion in lost productivity every year.

To contextualize the scale of this cost, the Federal Government has budgeted $412 Billion for mandatory Medicaid spending in 2019. Employee disengagement and workplace departures risk lowering morale amongst remaining employees and results in recruiting and training costs. While some employee turnover is natural and to be expected, consider the following eye-opening, preventable reason for disruption to employee retention.

The OC Tanner Learning Group published the results of a 10-year, 200,000 person study, “Performance: Accelerated.” Managers and employees were interviewed for the study, which centered on employee engagement and retention. The results revealed that 79% of people who left their jobs cited ‘lack of appreciation’ as their reason for leaving. Forbes online recently cited a poll which showed that more than 35% of employees consider “lack of recognition” of their work as the biggest hindrance to their productivity. The Wall Street Journal commented that this report provided “a startling link between recognition and profitability.”

Reasons for quitting work pie chat and statistic

Given the extremely high number of people who attribute their reason for leaving a job to feeling (or being) under-appreciated and the resulting costs to business, one would think that employers would make appreciation and gratitude expression a top priority for themselves and managerial staff.

Over the past thirteen years, I have managed the operations and functionality of teams in a range of industries. I am now an (appreciated and thankful) administrative member of the Corporate Development team at Loeb.NYC.  

Throughout my career, I have witnessed numerous acts of appreciation, as well as some demoralizing methods for seeking performance results. Eventually, people who didn’t feel they were treated well always resigned, and sometimes did lasting reputational damage to a business. The reputation of one company suffered so severely as the result of complaints by a disgruntled former-employee that relationships with other businesses and customers were severely impacted. The situation attracted enough community attention that sales drastically decreased. The company closed its doors late last year. 

Nina Lichtman illustration two people in meeting

Fortunately, there are simple ways to mitigate the risks and costs associated with employee turnover and low morale, as well as to boost Return on Investment (ROI) of retained employees. Genuine and well-timed expressions of appreciation have multiple benefits (financial, time, production output, etc.), and are not costly or time-consuming.

Say “Thanks”, Show Thanks

A verbal “thank you for [specific of what you’re thankful for],” can change a colleague’s mood and outlook, and let them know that you care about their professional well-being. Brendan Kamm, CEO of business-centric, mobile gifting app, “Thnks” has founded an entire venture on the premise that expressing gratitude has a ripple-effect and is a valuable workplace exercise with multiple rewards. He states,

“The most powerful tool you have for creating success is to appreciate others. Simple, considerate gestures, like saying ‘thank you,’ have the power to completely change another person’s perspective. It demonstrates that you value their time and respect your relationship. The Art of Appreciation is the ultimate game changer.”

Thnks’ platform allows users to send (customizable) gifts with personalized messages and requires only the recipient’s email, twitter or SMS address. Kamm cites the following effective examples:

Send someone an Uber Ride on a rainy morning to make their commute a little easier and their day a little brighter.”

Coffee for the Week is a great way to show your appreciation to someone who you know has a trying week of work ahead of them. Help keep them caffeinated!”

For the person who is always on the road, a more legroom seat upgrade or carry-on cocktail kit can make their life on the move a little more comfortable while demonstrating your thoughtfulness.”

To gain further and more immediate insight into the effects of appreciation in the professional context, we conducted an anonymous, external “Workplace Appreciation Survey.”  We asked, “Have you personally been shown appreciation by someone at work?”. Most examples provided in answer to that question were not major pecuniary or grand gestures, but rather tokenistic or verbal acknowledgments, not tied to a formal reward or review program. For example:

Nina Lichtman illustration appreciation gift ideas



“I got a cookie.”

“Praise, recognition, gratitude.”

“Kind words in a card, token gifts, food.”

“I was rewarded with praise from my supervisor and a gift card.”

“Thank you emails, shout-outs in meetings or at events, thank you cards.”

“I frequently hear from other team members how much they appreciate having me there.”



These examples may seem simplistic, even infantile, but what these responses demonstrate is that people remember small, timely expressions of gratitude. And that genuine expressions of gratitude, rather than the monetary worth of the gift itself, is meaningful and effective for building morale and improving employee retention in addition to team building and a formal pay increase structure.

Showing appreciation is not a one-way street or exclusively “top-down” in nature. While it benefits both parties (and business) for employers to show gratitude to their employees and subordinates, it is also pragmatic and valuable for the recognition or consideration to flow in the opposite direction as well. Managers and high-level executives deserve thanks too. A survey respondent added,

My partner and I tell each other “good job” frequently. He’s very good about giving positive feedback. We meet daily and go over our agenda and pending requests from clients. We also talk about ways we could both improve. I feel extremely valued at work, not only by my partner but by our clients as well.”

It doesn’t cost you anything to say “thanks”, but it might cost you not to.

it doesn't cost you anything to say thanks

Team Building vs. Targeted Gratitude

Lest one think that group offerings like company events and team building exercises are enough to prevent or cure “under-appreciitis”, this way lies false hope. While group events and team-building are important in their own right and may serve to demonstrate collective recognition and morale-boosting, team recognition does not adequately tackle the problem of an individual employee feeling despondent, undervalued or taken for granted. Group activities are not designed to focus on the performance of any one individual.   

Sandra is an experienced accounting and finance professional in New York City. She has worked both as a low-to-mid-level employee but has also held managerial and CFO positions. Sandra has experience across enormous, big-name corporations as well as smaller hedge funds and companies. She makes the case that while team events can be useful for boosting morale, some employees would also like flexibility for “priorities outside work” and that team-building works  best if it feels organic and not forced:

“I have a life outside of work; I have priorities outside of work… [which take] time to maintain. Organic colleague bonds are really strong, but… I prefer an organization to respect the individual. If you’re on a good team with good people who support each other, it’s hugely instrumental in defraying feelings of unfair work or lack of appreciation.”

Nina Lichtman illustration happy employees

One person who answered the survey made the following point about group versus individual appreciation:

“Although I didn’t leave the job because I didn’t feel appreciated (it was a one-year residency), I will not return to work at that organization because I felt like the morale was so low. A huge part of that [decision] is lack of recognition and appreciation from management for the efforts of those in the department…The manager explicitly stated that she did not believe in recognizing people individually because it creates “animosity” between staff members… She was not even supportive of getting people candy bars on their birthdays. It fostered an environment full of animosity and a focus on the negative. Hardly anyone in the department felt appreciated.”

Our external “Workplace Appreciation Survey” asked a question derived from the OC Tanner study mentioned earlier, “Does the person you report to do a good job of recognizing employee contributions?” One answer stated, “Currently, no. I no longer work in an environment where we are praised or recognized for the things that we do.”

How do I manage?

I realized that a good manager is a great leader

For three years, I was a manager at an ice cream company.  When I started, there was one small store in San Francisco.  There were eight people on staff, including two founders. We received investment capital, and suddenly I was opening stores and hiring at pace. At that time, I had a conversation with a team member, which impacted how I view the importance of appreciation and myself as a manager.  

He had been working overtime, late shifts and sacrificing weekends. He was drained. I didn’t notice until it was too late.  In one of our final conversations, he told me, “I feel like I am doing everything for everyone else and no one is doing anything for me.”  I felt like I had failed him. He left shortly after that.

From that point, I realized that a good manager is a great leader. I started having weekly one-on-one check-ins with people I managed. We discussed roadblocks in operations and what I could do to set them up for success.  We held manager meetings where staff could showcase their wins. As a result of these efforts, day-to-day operations were smoother, and the team more cohesive. It was a tangible improvement. Taking the time to hear employees out, address concerns and provide individual feedback, made my team feel appreciated.  Sandra (hedge fund CFO) agrees,

Part of learning how to manage is to be actively trained on what your staff is doing. In my position, I like to keep a list, for people I work with when they’ve done something really positive. If it’s something negative, I will usually address that right away. If [one] think[s] reinforcing positive behavior is far more beneficial [than only noting negative behavior] you’re in better place at the end of a reporting cycle if you track performance in real time, to more accurately weigh the employees’ pros, good qualities, and development areas.”

Low-Cost Methods to Help Staff Feel Appreciated*

*With High ROI.

Give regular, constructive feedback

Set aside some time to go over changes your staff could make to improve. Express what you genuinely like about a team member’s performance, contribution or abilities.  Avoid creating a situation reflected in this survey response: “My boss was not into positive feedback. It was just assumed we should work well. He only let us know when there were issues.” Inform individuals precisely what you like about their work. Contextualize your comments by identifying how their efforts contributed to the team’s goals.  

Timing is everything

Giving feedback when the timing is not linked to formal performance reviews or deadlines will be perceived as more genuine. Sandra comments,

“There has to be out of cycle performance rewards for people who you value. Too many times only when someone is leaving, has [the employer] pulled the ‘money card’ and at that point it’s disingenuous and it’s too late. A clear indicator [of disingenuousness] is people who express praise only when there’s a pressing deadline, or there’s a linked benefit. But that’s why genuine feedback or taking time out of the normal stress and routine of work, or taking someone for coffee and informally going through their strengths and development points, has been a much better way to give that kind of information because it’s a conversation in somewhat isolation.”

By showing appreciation you can significantly lessen recruiting, re-hiring, training and gap-filling costs

Be aware of your employee’s time

Employees can feel taken advantage of if their manager is not mindful of personal time, is not aware of what the staff-member does with their work time, or lacks a realistic picture of how long tasks take to complete. According to a survey respondent, “When my shift was over, I wish [my manager] could have been more aware that I am tired and I want to go home. Not have me linger around longer ‘cause my employer wants to talk… I think some people are not aware of how much work goes into some of the projects I work on.” 

Advocate for your staff

Have a system to remind yourself of the positive work your team members and colleagues are doing and spread the word.  An extra step is being an advocate for a person. Managers may not have a say over their team’s pay, but it is meaningful for a supervisor to inform a senior person or HR member of the value a person adds and their strongest skills. A respondent claimed, “When people promote the work I do for them or acknowledge the effort and love I put into it, it brightens my life up.

The Profits of Proactive Appreciation

By showing appreciation, you can significantly lessen recruiting, re-hiring, training and gap-filling costs. You can mitigate the risk of damage to morale and business-reputation caused by employee turnover due to feelings of unappreciation. The prophylactic for this scenario is to offer small and timely words or gestures of thanks, and it makes financial sense to take those steps. If those words and gestures not only prevented loss, but stimulated profit, growth, and productivity, it would be suboptimal business not to consider it.

Happily for me, Loeb.NYC is an environment that cultivates a fun and rewarding employee culture, and actively cares about staff satisfaction. I’m grateful for that.


 *Original Illustrations by Nina Lichtman, (Dashride). Graphics by Alyssa Liegel. Leigh Adler, Editor. Contributions by Brendan Kamm. 

Driverless Cars, The Future of Ground Transport

Dashride, by creating software for ground transport companies,  has empowered their customers to compete with companies like Uber and Lyft. I interviewed Dashride’s CEO and Co-founder, Nadav Ullman, about their work with the tech for driverless cars and the future of the automotive industry.

As an Administrative Assistant, my seat at the reception desk at Loeb.NYC gives me the perfect vantage point to learn about all of our companies. I meet everyone who steps through our doors. Working here and seeing everyone and everything, every day is incredibly exciting. One of our companies in particular has stood out to me lately. A software company in the taxi and transportation services industry, Dashride.

Dashride’s work in creating software for taxi/limo companies both large and small has helped empower their customer base to compete with “transport on demand” companies like Uber and Lyft. Dashride is also finding the best ways to introduce autonomous cars (self-driving cars) in the very near future.

What is Dashride? How did you build the company?

Nadav Ullman: ­Dashride is a B2B SaaS [Business to Business, Software as a Service] platform. The platform allows ground transportation companies to modernize their operations and consumer offerings. Our platform helps these fleets by adding automation, reducing costs, and allowing them to properly compete in a rapidly changing industry.


When Tom [Bachant, Dashride co-founder] and I were still in college, we were working on a B2C ridesharing app that connected college students who needed safe rides to the designated drivers on campuses [Sobrio]. We had launched the app on 8 different large college campuses across the country and had thousands of people using it to get around safely.

Before long, Uber and Lyft began to come out of beta and launch in major cities. Existing fleets started to call us saying “Hey, that technology that you built for the universities, we need that for our business.” We quickly realized there were two things going on: one, existing fleets were using antiquated systems to run their companies, which inevitably led to antiquated processes, and two, Uber and Lyft were acting a forcing mechanism to push these companies to modernize. The demand was obvious, and with over two-hundred-thousand fleets in the US alone, it was clear there was a massive opportunity. We soon pivoted the college-focused app to an enterprise platform.

Today, over four-hundred fleets from across the world use Dashride to run their businesses. Our customers range from legacy taxi companies to US municipalities to, more recently, driverless tech companies who are looking to launch a consumer offering.

Interior driverless cars

What is the future of ground transportation?

Nadav: Today if you want to get from point A to point B, you can buy a car, rent a car, get a taxi, or use mass transit. These options are quickly converging in a variety ways. Driverless technology is coming to the consumer in the very near future. Alphabet’s Waymo is already expanding their trial in Phoenix and driving folks around every day without a human controlling the wheel. There are at least twenty to thirty other companies who are not very far behind. Right now on average eighty percent of the cost of an Uber goes to the driver, so by cutting out the driver we’re drastically reducing the cost of ground transport. By adding complex pooling functions on top of that, we’re able to cut the costs even further.

Existing bus and shuttle routes will become dynamic, based on real-time demand. Existing car manufacturers who have built massive businesses by selling expensive assets are now all investing heavily to figure out how to start providing transportation-as-a-service instead. Car Rental Companies, OEMs (car manufacturers), and ridesharing solutions, and new tech startups are all finding themselves competing with each other to deploy the most highly accessible and cost-effective fleet.

Are driverless cars a good ownership investment? What does car ownership look like in a self-driving world?

Nadav: The average person uses their car for thirty minutes a day, and at any point, there are over a trillion dollars worth of parked cars just sitting around unused. For the average person, owning a car will certainly not make sense. In the short-term, there will continue to be a consumer market for buying cars, and during their under-utilized times, owners will put them up on a driverless network. As rides continue to commodify, car ownership will continue to drop over time. This is both an existential threat to the existing OEMs and car rental companies, as well as an enormous opportunity. The Dashride platform is well-positioned to help usher these companies into the future of driverless cars by providing a proven platform to launch a consumer ride-sharing solution.

If everyone uses driverless taxis, will companies like Uber dominate the market, or is there room for competition?

Nadav: Uber’s greatest value right now is that they have the closest available driver to you. Once drivers aren’t in the equation, their greatest competitive advantage disappears quickly. Soon, it will instead come down to who has the closest available autonomous vehicle. By 2025, the AV (autonomous vehicle) industry in the US is speculated to be forty-five billion dollars and seventy-seven billion dollars by 2035. Some project far higher. It should not come as a surprise that there’s massive companies are investing and vying for a portion of the driverless cars market. The coming disruption in the ground transportation industry is going to be far larger than the disruption that Uber and Lyft have been creating. We still have a long way to go before there are clear winners in the industry.

inside driverless carsWhen are driverless cars going to hit the market?

Nadav: They already have. Waymo is currently providing rides to a handful of communities in Phoenix and has already announced expansion plans of the taxi service to a larger territory. There are driverless shuttles available to the public in places like Greece, China, the Netherlands and even in Las Vegas. Autonomous transport on public roads isn’t just speculation. Dashride is currently providing software to several autonomous technology companies to help them bring their technology to consumers, and these companies are most often waiting to be approved to operate by local governments. The technology is built, and regulations are just starting to catch up.

How will autonomous cars affect the environment?

Nadav: The important trend in the industry that’s happening as it relates to the environment is the uptick in production of electric cars. India, France, Britain, and Norway have already announced that they plan to phase out gas-powered cars altogether through regulation. Other countries and even US states like California have hinted at similar moves in the future. Car manufacturers are responding quickly with electrified future lineups, so we’re going to see a lot more EVs on the marketplace. Between regulations, and the rapid decrease in the costs for battery tech, we are seeing there are a lot of reasons to be optimistic.

Caroline: Elon Musk’s The Boring Company has been designing underground highways with the expectation that we can use these for faster long-distance travel and use existing roads for shorter distances. Alphabet, Google’s parent company, has started building its first “techified” city in Toronto through the Sidewalk Labs project. We appear to be heading toward designing cities and infrastructure with tech and innovation in mind.

Nadav: Designing cities with the latest technology has always been the case. Ancient Rome became successful in part due to their innovative techniques of constructing concrete buildings and installing aqueducts in their major hubs. Innovation is certainly happening at a faster pace now, so it becomes harder for governments to keep up. Public/private partnerships like the one between Sidewalk and Toronto will be an important way to balance the pace of the tech sector, and the promotion of general welfare for citizens. We’re seeing this happen first-hand. Dashride has partnered with US municipalities to help modernize their city taxi offerings. They are using our tech to increase accessibility to reliable transportation, an important function of a local government.

new york city street view

Will we need to change infrastructure to work for driverless cars?

Nadav: I think about it from the other way around. What we’re seeing is that in the effort to bring products to market, companies are designing their autonomous vehicle technology to accommodate to our current environment, and reacting to existing signals. We don’t need new highways or signage to make it a reality. Where it gets interesting is how our surroundings will be designed differently once the adoption occurs. Right now, when you look out the window, think about how much of our environment today is designed around the behavior of human driver – how much space is taken up by massive roads and driveways, parking lots, and highways.

It’s not the case that we should start building new infrastructure to accommodate for upcoming driverless cars, it’s that these new vehicles will allow us totally redesign our towns and cities to better accommodate for other priorities – more bikers, communal spaces, and parks.

Tom Bachant and Nadav Ullman were included in Inc. Magazine’s list of “30 Under 30” Most Brilliant Entrepreneurs, 2017. 

Loeb NYC Brings Inclusivity to SxSW

Loeb NYC logo hamptons background

While Loeb NYC has historically participated in various conferences as attendees, in March, 2018, we hosted our first activation at SxSW in Austin, Texas. With Bonin Ventures, we hosted two days of content with some rockstar panelists, including Gary Vaynerchuk (CEO of Vayner Media), Swan Sit (VP of Global Digital @ Nike) and Kris Skrinak (Machine Learning Architect @ Amazon) — not to mention our inspiring leader, Michael Loeb.

In addition to a lively conversation between Michael Loeb and Gary Vaynerchuk, moderated by Bonin Bough (you can find the video here), we also hosted the Real Inclusivity panel. Some pretty badass women discuss how to generate cultures in which all voices are heard:

At SxSW we also promoted the second annual “___OrNot” conference to be hosted in Southampton, NY (at “the Billions house”) on May 18th, 2018. The Or Not conference aims to help brand marketers separate marketing hype cycles from the real opportunities that are appropriate for their brands. Visit the for more information.

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Loeb NYC Inclusivity Panel at SXSW

Loeb NYC Speakers Series: Cryptocurrencies with Alyse Killeen

Loeb NYC background image lilac

Around the Loeb.NYC offices, I’ve noticed chatter about cryptocurrencies and blockchain. Given the nascent, confusing, and somewhat mysterious nature of the technology and its ecosystem, I suggested that we host Alyse Killeen for the monthly Loeb NYC Speakers Series. Alyse is a Los Angeles-based venture capital investor who focuses on data science, network infrastructure, fintech, e-commerce, and blockchain. She has contributed to two books on cryptocurrencies: “The Handbook of Digital Currency” (2015) and “The Handbook of Digital Banking” (2017).

The Bitcoin Surge and Decentralization

When I first met Alyse at Michael Loeb’s Founders & Funders event in 2014, the price of a Bitcoin was around $400. Now, in late November 2017, Bitcoin’s price is approaching $10,000. With this massive surge in price (+2,400% in just three years), Bitcoin has generated major interest from the mainstream. As talent and capital have poured into the space, it’s become clear that Bitcoin and other cryptocurrencies are here to stay. One of the goals of the Loeb NYC Speaker Series is to promote company-wide understanding and discussion of new ideas. Given the amount of buzz in the space right now, hosting Alyse to explain Bitcoin, blockchain, and its implications going forward was a no-brainer.

Above: Fintech Silicon Valley interview with Alyse Killeen on what drew her to the blockchain, and on inclusivity.

For Alyse, the importance of blockchain technology can be boiled down to its power to decentralize structures and institutions that are traditionally relied upon to establish trust between multiple parties.

Alyse explained that Bitcoin emerged in the wake of the 2008 financial crisis, partly in response to eroding trust in financial institutions and governments. She explained that Bitcoin users can choose to transact on their own terms without the consent of any intermediary. As more people earn, buy, and use the currency, its price increases. While rampant speculation has obviously contributed to Bitcoin’s rapid price increase, adoption and usage has grown substantially as well.

Alyse explained that instead of a central institution like a bank maintaining a ledger of balances, the Bitcoin blockchain is maintained by a worldwide network of financially-incentivized “miners” — people who have set up computing hardware to verify Bitcoin transactions. Miners earn Bitcoin rewards in exchange for their participation in the network. Mining is intentionally expensive, requiring high-powered computers and substantial electricity consumption. Thus, miners have begun to set up shop in regions like China and Venezuela where electricity is relatively inexpensive.

Alyse Killeen signs the wall at Loeb NYC Speakers Series Decentralize all the things
Alyse Killeen signs the wall at Loeb NYC Speakers Series

How does Bitcoin Mining Work?

The system is designed to work as follows: as Bitcoin’s price increases, more miners will participate in the network. As more miners join in, the faster and more secure the network becomes, ideally creating a virtuous cycle that allows for seamless, borderless, and secure exchanges of value without the need for any centralized intermediary. This is particularly important in nations without the institutional stability that we tend to take for granted in the US. In a country like Venezuela that has experienced hyperinflation, Bitcoin has become a viable alternative to its national currency. For those interested in investing in Bitcoin, Alyse had a few recommendations: only invest what you’re willing/able to lose and store your cryptocurrency in a hardware wallet like the Trezor or Ledger.

Initial Coin Offerings

Another subject that came up was the recent Initial Coin Offering (ICO) craze. Alyse warned that a lot of these ICOs are scams but believes this financing model will ultimately democratize access to capital. To briefly explain an ICO, companies seeking venture funding can create and issue their own token as a means of financing rather than traditional equity or debt deals. Presumably, as the company grows, the value of its token will increase. Token holders are immediately liquid, unlike with traditional venture capital or angel investments. Alyse recommends doing serious diligence on ICOs before investing, as one should with any investment.

It is an exciting time in the world of cryptocurrencies. There is a lot to learn and sometimes answers to the questions you have may not even exist. From all of us at Loeb, we’d like to say thank you to Alyse! For more information about Alyse, visit her website and follow her on Twitter.

Adam Rice

Adam is a Venture Associate at Loeb NYC, where he sources, evaluates, and pursues new business and investment opportunities. He is currently focused on fintech and blockchain. Prior to joining Loeb.NYC in 2014, Adam received his BA from the University of Michigan.

Offensive Content on Social Platforms

Content moderation on social media is a weird pet obsession of mine. The internet is full of garbage, both benign and insidious, but a number of recent headlines bring the issue into stark relief:

Google links to hoax articles during breaking news. Twitter is filthy with Nazis. YouTube’s algorithm has been suggesting and promoting bizarre, disturbing content to children. And Facebook has an overseas army of content janitors, a legion of hundreds who still can’t keep the platform clean. Indeed, many tasked with scrubbing Facebook of offensive content end up traumatized, permanently shaken by the sheer volume of violence and depravity the job exposes them to, and what it reveals about the darkness of humanity.

The reason I describe my obsession with content moderation on social platforms as ‘weird’ is that I have no solution in mind. The more I understand about the problem, the more convinced I am that social platforms, as they are presently understood, will never be able to keep their users safe from offensive content. It’s like fighting a Hydra, where if you cut off one of its heads, two will grow in its place. But in this case, it’s hundreds and thousands of hours of content that a handful of underpaid moderators are tasked with parsing. 

Unwanted Interactions

Here’s a story: a few years back I was doing community management for a small social media platform operating in stealth. This was a social network built on small groups that facilitated text, image, video, and audio sharing, and (alarm bells) live video chat. It was also (glaring siren) aimed at a teen demographic. If you remember Chatroulette, I don’t need to tell you what happened next.

Now before you sprain your neck rolling your eyes at the hubris of such a venture, a few facts about this company: we had a famously brilliant CEO, the seed funding for the company was brow-raising, and our engineering staff was world-class. Our, ahem, “unwanted interactions” problem was not the result of unskilled dilettantes throwing darts at a board. The people behind the product strongly believed in both social discovery and the power of live interactions. They knew they had both a moral and business duty to make their platform a place that was fun and safe for everyone. It was their number one priority.

Yet in the end, they decided they simply could not do it. At least, not with the product they had. Ultimately, they pivoted from large, public groups to small, private groups. Last I checked they’re doing fine. But they’re not huge.

Because it turns out, the very thing that drives growth (and valuation) in social platforms, facilitates the abuse that comes to plague them.

It’s very hard to have viral growth of any app without incorporating levers built to aggressively expand every user’s social graph: suggested friends, suggested pages, suggested rooms. In the hands of users with good intentions, this can very quickly bring one into contact with toxic elements. In the hands of malicious users, this presents endless new targets to harass, stalk, and intimidate, each of whom is outside the malicious user’s real-world social circle.

So that’s how abuse becomes commonplace on social platforms. But why is it so hard to stop? Why can’t platforms simply ban the offending user, delete the offending content, close the offending channel?

As I see it, there are 3 reasons why no major social platform has “solved” abuse:

  1. The valuation of social media platforms depends on the discovery capabilities it provides and on wide, active social graphs.
  2. Many (most?) major platform founders and top brass, genuinely believe in unfettered discovery and in free speech as universal, absolute social positives.
  3. Decision makers at major platforms know that any effective solution to offensive content on their platform would involve unbelievably complex, contextually aware AI, that simply does not exist right now.

Worth noting: the major platform with probably the smallest abuse problem is Snapchat, which requires users to either know each other’s name or snap each other’s QR code in order to connect. In other words, the app that is least aggressive at expanding the social graph has the smallest abuse problem. Not a coincidence.

Audience Plus Content

Point number 1 seems self-explanatory: social media platforms require a virtuous cycle of content generation and discovery to stay relevant. A user posts content knowing it will have an audience. That audience interacts with the content, sending positive reinforcement to the author, inspiring the author to make more content. The audience itself is inspired by the content to create its own, and the cycle continues. Keeping the user returning requires consistently fresh content, and fresh content requires both an active community and easy discovery of content outside a user’s existing network. Nail that and you’ll always have users, which means you’ll always have advertisers. Nail that, and you’re a billionaire.

Free Speech Issues

Point number 2 might be a bit controversial, but without making a political judgment of any kind, I’d direct you to former Twitter VP Tony Wang’s famous “free speech wing of the free speech party” line, Facebook’s stated purpose (until recently) of “making the world more open and connected,” and various statements made by Reddit founders and executives on why, among other things, they let /r/jailbait exist for more than one nanosecond.

Machines Aren’t Ready to Help with Content Moderation (Yet)

The real rub comes from point number 3. The sad fact of the matter is that the flow of content generated by both human and bot actors on the internet is far wider and faster than any human-dependent solution could possibly counter. There are 500 million Tweets posted, 30 trillion pages crawled by Google, 432,000 hours of video uploaded to YouTube, and 576,000 new users added to Facebook every single day. You can’t ban every offensive account, you can’t screen every video, you can’t even tell who is going to be toxic when they join Facebook.

Or at least, no human, no amount of humans can (not when malicious actors are deploying bots to facilitate their aims). But word filters can be built, AI can identify certain errm, human parts, and patterns of behavior can be mapped for the most regularly reported users.

But these are all imperfect half-measures. Because AI is bad at stopping abuse before it happens and bad at using context to flag offensive content. The purest example of this failure can be seen in the recent viral post, There Is Something Wrong On The Internet, where the author documents how the YouTube algorithm has been gamed by spam accounts to rack up millions of views of bizarre, frightening content, all the while reaping ad dollars for the account owners.

No AI could stop content like this because you couldn’t describe to an AI why it was offensive – or at least, you couldn’t describe why in a useful way, a way that prevents future content from this from ever being served from children. Filtering stuff like this takes a human eye. At least, for now.

Of course, there is another option. Google can stop pushing discovery on its YouTube platform. It can trust that if the user wants something, she will seek that out. But for that to happen, for Google to stop thinking about their platform as a neutral territory for discovery and start thinking of it as either an archive to be browsed, or a media channel to be managed, Google would have to completely upend what they see as the actual purpose of YouTube. That of course, would mean accepting slower, smaller growth.

So I wouldn’t count on it.

Silicon Valley Valuations - Let it Be Real

loeb nyc logo green

The Venture Capital (VC) landscape, for the past decade steeped in Silicon Valley culture, has fabricated hundreds of “unicorns” – startups with billion-dollar-plus “valuations” (why the quotes? Read on). The question is, are these valuations real? Are they merited or earned? 

My Dad, the great Marshall Loeb, told the joke of “this guy” (joke maker-uppers are evidently misogynists – or is the opposite the case?) and the $10,000 dog. Each day he goes to a bar, mangy mutt in tow. This guy is subject to unrelenting derision from his fellow revelers, which only intensifies when in defense of his pet, he declares ‘this dog is worth $10,000’. After a time, he has quite enough of the mutt-busting. “Ok, I will prove it to you”, he countered in defiance, “Be here tomorrow.”

The following day, like clockwork, he reenters the bar with a smirk wider than the gulf between Pelosi and Trump, and matching cats under his arms. “You see, I told you pagans that the dog you made so much fun of was worth $10,000 and now I have the proof”.  “Say what?”, asked the confused chorus. “I traded him for two $5,000 cats”.  

michael loeb quote how many of these mythical creatures will be more than myths

A Herd of Silicon Valley Unicorns

In 2016, the VC ecosystem echo-chamber fabricated 160-something unicorns. I asked two-dozen start-up CEOs, carefully selected for some gray hair wisdom, two questions:

How many of these mythical creatures will be more than myths? And; how much green ($) will the founders ever see? Answers: Few and little.

Fund managers are subject to a number of pressures, one of which is finding deals. On the spectrum of asset classes, venture is illiquid, risky and in theory, high returning. Committed capital from investors is ‘called’ over time as deals are consummated, requiring that funds are held in highly liquid, safe and therefore low returning instruments – in sum – the opposite end of the asset spectrum.

michael loeb quote fund managers are promiscuous always on the next fund

Investment outcomes are generally thought to be highly dependent on a specific asset allocation formula. Investors count on VCs to make their investments with alacrity so as not to, egads, wither in the wrong class.  And while not all entrepreneurs are serial entrepreneurs (and not all would-be entrepreneurs have the “entrepreneur’s gene“), fund managers are invariably promiscuous, always on to the next and bigger fund for the increasing fees – which investors are subject to shine (good returns) or rain (bad ones) – and marketplace juju.

In a low return world sloshing in cash, (why else would the Nets, a team that last ruled their conference during the Internet winter of 2001, be worth $2 billion?) startups are bid-up and are ‘marked to market’; that is, valued from the last overheated investment, often by another VC firm. This is long before the mutated unicorns become sickly, but in time for display on the VC-scoreboard to impress the big wallets for the next fund in the series.  

I know what you’re thinking: the government (oy vey) should do something about this. Watchdogs are obliged to protect the little guy, and venture targets the ‘sophisticated’ investor. You better know what you are doing to ski the black runs or you may just fall – hard. You’ve been served; fat-cats beware.   

michael loeb quote you better know what you are doing to ski the black runs

A case, from zillions of postulants, in point. A VC fund in which I have invested (does this make me a hypocrite?) marked-to-market a lipstick-on-a-pig startup (old product, pretty digital interface) for which revenues this year will drop by a predicted 1/3rd, will lose over $200 million, owns little unique IP, but has a brand-name VC money sponsor (hint: there is an intimate connection to the White House’s alpha male) to $2.8 billion. Huh? For a negative growth newbie? Oh, but management has projected revenues to triple in 2018 with a $300 million swing on the bottom line to profitability. And no, it’s not in cannabis so ‘eating home cooking’ doesn’t explain the hyperventilation.   

Real Growth and Real Time

‎There is a reason why Warren Buffett doesn’t touch this stuff – he takes a long-term viewTo be sure, the market puts a premium on innovation, novelty and first-in-market positions – that is where you find big growth and the big opportunity. Investor insanity is fleeting and corrections are violent: my founder’s shares in Priceline went from $16 at IPO to $163 in months to $1.28 months later at the nadir of Internet meltdown #1 (Nick Bilton argued in 2015 that there will be more). In the long run, the market values what is real: real companies inventing real solutions, real revenues, real profits, real value. Not unicorns, nor $10,000 dogs, nor two $5,000 cats.

michael loeb quote investor insanity is fleeting and corrections are violent

We live at a time of great transformation, in which every industry will be subject to wrenching disruption. As an entrepreneur, nothing could be more invigorating. There are great ideas – big and brilliant – which will be sown and burgeon in vast new companies.  The ones that will stand the test of time, the ones of which Keats would say are not ‘writ in water’, will be made of sturdier stuff.

So entrepreneurs, summon your genius and courage to build something good that lasts, something that fuels the soul, something that will make you and your investors’ money and your Mama proud. Let it be real.  

Establishing Office Culture is Key to Startup Success

 One of the best things about starting your own business is that you get to (try to) build whatever type of company you want — including the culture. Everybody has been in organizations where the overall culture and values, or at least certain management styles, were toxic. Or maybe a lack of leadership undermined employee morale and performance. So why would you want that to happen in your own business?

The case for actively creating a culture

Surprisingly, startups and closely-held businesses often fail to instill values and foster a culture conducive to a positive and productive working environment. I’ve seen many small businesses where the organization’s culture was defined by the dynamic and dysfunction of its founders. In startups, where long hours, tight deadlines and high stress is the norm — and where high-performance and passion are critical to success — low morale and high turnover can be a recipe for disaster.

Taking the time to define, communicate and instill your startup’s cultural principles may seem like a luxury compared to launching, marketing and selling your products and services. However, if you don’t take the time to do it up front, you may not get a second chance.

Michael Loeb quote summon your genius and courage to build something good that lasts

How do I start(up)?

In a startup, it’s easy to place the focus on whatever the shortest path is to get things done and meet critical deadlines, launches, and milestones. But if you’re not careful, you can end up with an organization that lacks a clear set of cultural values or leadership practices, and a staff that’s not motivated or empowered to do their best work. Here are some ways to prevent this:

Write it down

Think about what kind of culture you want for your organization, and write down a set of cultural principles and company values you want to aspire to for your employees, customers, and partners.

Include the team 

Communicate your cultural principles and company values to your employees, and take steps to get feedback and buy-in from them.

Show you’re invested 

Commit to actions the company will take to instill and uphold cultural principles and values.

Empower your employees 

Allow them the freedom to perform in the roles they were hired for, and give them room to make mistakes and learn from them.

loeb nyc employees high five
Loeb NYC employees support each other

Foster accountability 

Establish standards of trust and independence among employees, and strive to weed out those who consistently fail to live up to it.

Hire carefully 

When hiring for key roles, especially those in management positions, make sure have you a clear understanding of a candidate’s leadership style and skills, and that they align with your desired values.

Walk the walk 

Strive to embody the values you want to instill in your organization in your daily actions and communications.

Celebrate success 

Take the time to recognize great work and contributions.

Using the above techniques can set your startup on the right track for success, productivity, and low employee turnover. At Loeb NYC, I have observed a large emphasis placed on establishing a culture of fun, employee satisfaction, and fulfillment, and continued learning. This is done through events like “Speakers Series” and weekly staff meet-ups (celebrating birthdays and milestones). It helps make people happy to come to work on a Monday.

Creativity, Inc. Book Cover Ed Catmull

Recommended Reading

Part of our company culture: Loeb NYC has started a monthly book club (and sponsors the books for whoever wants to join in). Each month, a new “Loebster” moderates the meeting, leads a discussion on the book of the month and votes on the set text for the following month. The books selected relate to improving business, productivity, creativity, innovation, and inspiration. Loeb NYC’s book for April 2018, was “Creativity, Inc.” by Pixar’s founder, Ed Catmull. Catmull, after the release and success of Pixar’s first movie (and the first ever computer-animated feature, “Toy Story”) was faced with the challenge of breathing inspiration into a burnt-out, uncommitted staff. Catmull describes how he made actively, continually improving company culture his personal mission, as a crucial ingredient to the creative process and Pixar’s success.

Chris Dowling VP of Product, DgDean

DgDean develops the technology necessary to fuel businesses – whether for startups or established companies. DGDean eliminates the burden of tech with a unique, proven approach and guiding principles. They enable your digital structure to evolve with your customers’ needs. This includes data collection, analytics, coding, design and more.

The Entrepreneur's Gene

So… you want to start a business. And you want to know the most important thing? Forget capitalization, the right industry, the board of directors or the business model. Why, it’s the entrepreneurs’ gene, of course. For decades, scientists have been trying to isolate and replicate this elusive gene but have thus far been unsuccessful. The objective is to make the gene generally available so that anyone can be a Jobs, a Zuckerberg or a Bezos. (Note: in a free, democratic and fair society, why should only entrepreneurs be blessed with the entrepreneur’s gene? So elitist.)

Here is what scientists know about the Entrepreneur’s Gene  

Entrepreneurs have a number of unusual qualities. First, they are smart – unsmart entrepreneurs become un-trepreneurs real quick. They are indefatigable, accustomed to years and years of long, grueling hours. They inherently know that to be an entrepreneur the gene requires nurturing, fueling, and developing with continuous inputs of data, insight, and experiences.

And they persevere, Thomas Edison, one of their Gods, famously said: “I never failed, I just learned 10,000 ways how not to make a lightbulb”.  The devout have no understanding of failure, but they do understand how to try, try again. Not the same way every time, mind you, because doing the same thing over and over expecting a different result is endemic of insanity, according to Einstein, definitely an entrepreneur.  Freud, recently voted into the HOF by the Entrepreneur’s Writers Association, would tell you that the entrepreneur is delusional and perhaps insane (Van Gogh was reputed to have the gene, and yes, he was maybe crazy, but ohmygawd inventive – have you seen his stuff?)

Entrepreneurs have an unbridled audacity of belief. The audacity to believe they have an idea that no one in the history of human civilization thought of before them. The audacity to believe that their start-up (not just can, but) WILL work; that others will follow, that still others will invest and an army of others will buy.

The Entrepreneurial Personality

And here’s where the audacity crosses over into insanity: they believe the rules do not apply to them. Eight or ten new ventures fail? Not mine. The regulations don’t allow it? These will change. VCs will never invest? They haven’t heard the pitch. Turns out that the gene makes the entrepreneur hearing impaired. They can’t hear the words ‘no,’ ‘impossible,’ ‘this can’t work’ or ‘are your nuts?’

Similarly, the laws of physics and just plain simple rules that others accept and regard are ignored by these renegades as if they don’t recognize them. These qualities start to emerge in youth, as early as pre-school: ‘Why is Johnny not joining circle time but building a 1:24 scale replica of the Eiffel tower with blocks instead?’, or ‘Why does Jane doodle – her stuff complex, advanced, inscrutable – when the class is supposed to be learning about the famous clothespin decision of 1932?’  

Michael Loeb Quote being an entrepreneur has never been more important

Scientists have also discovered that the entrepreneur gene is closely identified with the pirate gene, the guerrilla gene and in particular, the MacGyver gene. Entrepreneurs have to make everything out of nothing and decisions quickly, assertively and without hesitation. Some of these are a matter of life or death (we refer here to the life or death of the company, not the entrepreneur or employees). Invariably these crucial decisions are made with too little data and MacGyvered interpretations of the evidence.

Captain Kirk was an entrepreneur. Un-trepreneur Spock, God Bless, would always share with Kirk the odds of surviving, say, a surprise attack on the Klingons with some new, unproven torpedo (has anyone ever called Roddenberry out for having a ‘torpedo’ in space?) which were as infinitesimal as Congress passing something useful this session. Kirk would smirk (earning him the moniker ‘Smirky Kirk’) and do it anyway. He sneered at the chances, cast aside the playbook, ignored the rules to save the universe, in a crazily creative, ridiculously risky, never-been-tried-before way each 50-minute episode. And it always worked out. Now that’s an entrepreneur. Except for the “always worked out” bit. That’s Hollywood.

I also find that the gene is inherited, and sometimes by osmosis. Many entrepreneurs grew up with entrepreneur talk around the dinner table, and entrepreneur-friendly parents. ‘Oh, she’s getting Cs but has an IQ of 145? I’m good with that’. Lest we forget, Einstein redrafted all the universal rules of physics as a Swiss patent examiner.  I don’t know much about Switzerland’s patent office, but I have to imagine that it’s a black hole for talent, and despite his prophecy to the contrary, Einstein escaped – but he was probably the only one. Like I said, the entrepreneur gene is irrepressible. Its genius ascends on canvas, in a light bulb, or in the stars… but it appears.

Michael Loeb quote entrepreneuring is a total-brain full-contact sport
Entrepreneuring is a total-brain full-contact sport. Be shy and die; delay – you’re the prey; you can’t be polite and fight. Both brain hemispheres are tingling with firing synapses that meld into… analytical creativity. Oxymoron? Jay Walker, friend, genius, founder of Priceline talks about the difference between data… and information. Data are numbers, plain (very plain) and simple. Information is numbers animated. DNA is a string of amino acids, the building blocks of life. But these do not a life make. Entrepreneurs turn data into the blood, vessels, muscles, and heartbeat of a company. The best of the lot can look at columns of numbers – thousands – and select the one or two that are aberrant. Seen through the right lens, new worlds appear … and the difference between success and failure. Without creative application numbers are symbols on a screen signifying nothing.

Entrepreneurs have visual acuity, both high and low. High – the big picture, a perspective from 35,000 feet. Low refers to the unit economics – the single customer.  If the unit economics don’t pencil out, no amount of scaling will a business make. After a talk with an adoring crowd, the 16th President of the United States was asked ‘Mr. Lincoln, why such a long speech?’ ‘Because I didn’t have the time to write a short one’ came the rejoinder. Entrepreneurs appreciate the elegance of concision and it’s power in communication. The best can put both the high and the low on the back of a business card. An entire business vision and unit economics in little more than a bumper sticker; a sound bite. Catch-phrases are repeated; speeches are read.     

Bobby Fischer, in his time the greatest chess player on the planet, was famous for playing two dozen games at once, processing billions of options in nanoseconds. His game was bold, inventive, and defied conventional wisdom.  But Fischer was no entrepreneur. Fischer could astonish, inspire… but he could not lead. And this is yet another quality of the gene, leadership. You see, the entrepreneur’s belief system is infectious. It is enveloping and passionate, and the best of them evangelize with the conviction and erudition of a Churchill, a Kennedy, a King. They dazzle; they mesmerize; intellectual shock and awe. They can flip the stubbornest of minds, the most jaundiced of opiners, into a legion of followers.

If you trawl for advice about the most important thing you’ll find plenty – too much actually – as though there were thousands of most important things, which is someplace between a paradox and a contradiction. But for my money, it comes down to this: the entrepreneurs’ gene.

My Top 3 Transferrable Skills

National Job Action Day

Didn’t realize it was Job Action Day?  Me neither – and I’ve been working in career development for almost 10 years (with my company, WORKS – a partner to LoebNYC). So I did a little research and discovered that this auspicious occasion was created in 2008 by LiveCareer. In the spirit of 2017’s theme; “Survive and Thrive: Using Transferable Skills to Give Your Career New Life,” I’ve picked the top three transferable skills we need to continually hone if we want to kick-ass in our careers.

Time Management Skills

One day, I decided to go running. I got back and said to my then-husband, “I just ran 15 minutes.” He was like, “that’s great, babe.” The next day I went out and ran a little further. I texted him at work: I ran 20 minutes. He came home that night and presented me with a sports watch so I could track my progress. The next morning, I went out, ran past my 25-minute marker, looked down at the watch and discovered I’d only run 7 fucking minutes. The point of this story is that when we’re doing something that is challenging, we tend to overestimate not underestimate, the amount of time we spend doing it.

You might have read Malcolm Gladwell’s, Outliers: The Story of Success (if you haven’t, pick it up).  He suggests it takes 10,000 hours to get to phenom status.  That’s a lot of time, a lot of dedication, and a tough threshold to reach when you’re sneaking peeks at your Instagram every fifteen minutes. Managing your time is no different than managing your money or your weight – tracking your progress is the key. Pick a skill, goal, passion project that you’d like to succeed at and track how many hours you actually spend doing it. My guess is that you’re going to be surprised.

Nicole Williams Book Cover Girl on Top
Nicole Williams, “Girl on Top”


Ten-thousand hours doesn’t come without commitment, and the root of your commitment is your ‘why.’ Why are you doing what you’re doing? For me, my mom worked in a paint factory while I was growing up and I hated how it sucked the life out of her. My why started out as, “Sure as shit that won’t be me,” but it turned into something larger, “I want to help others.”  There’s a secret to the why, the deeper you go… the more altruistic you go, the more likely you are to sustain it.  Your first answer may be “To pay the rent,” but think about what you’re contributing to the world, how you’re making people’s lives better, dig into that ‘why’ and find the wellspring of motivation.  Another book suggestion. Pick up Simon Sinek’s, Start With Why and find one of my favorite quotes as it relates to business; “People don’t buy what you do, they buy why you do it.”  What’s your why?

Relationship Building is a Skill

I was in the office of the Academy Award-winning producer of Silver Linings Playbook – in the pitch of my life. I was out of my mind nervous and used the trick of the trade in that kind of situation: get the focus off of you. I looked around his office, and on his wall was the framed Oscar-winning card with American Beauty printed on it (another film he produced).  I asked, “What was that moment like?”  He took a minute to think about it and told me a story about allowing himself to want, really want, to win, so that in the event he did win he could sink into the moment. 

Anyways, the meeting was a success and months later he told me, “You know, I’ve had the envelope framed on my wall for years. Everyone is so busy pitching me, no one thinks to ask about it.”  Our natural inclination when trying to build a relationship is to make sure we get seen and heard and that’s all well and good but the truth is the best way of making a good impression is by letting them take the lead, especially when it’s you in the selling seat.  Be armed with questions like; “What do you wish you would have known going into that situation?”,  “What was that moment like?”,  “Why did you make that decision?”

The above tactics are applicable and useful, whether you are looking to grow your current career, switch to a new career – or are simply looking for greater satisfaction in your current role.

Nicole Williams Job Quote
Click the quote to download Nicole Williams’ “Get the Job You Want” FREE ebook

Nicole Williams

CEO, Career Expert, Best-selling author, LinkedIn spokesperson and Today Show career correspondent.

After working both as a Career Counselor and as a Sr. Business Consultant, Nicole Williams founded WORKS in 2006, with the help of Michael Loeb. Nicole had the vision of building a business that not only helps young women create the careers of their dreams, but also supports the companies attempting to recruit and retain them as employees, and the businesses that are interested in providing products and services aimed at enriching their lives.


WORKS is a career brand dedicated to inspiring, revitalizing, educating and energizing professional women striving towards career success. Today, under the WORKS banner, and with an incredible team, Nicole Williams has authored three bestselling books: Wildly Sophisticated: A Bold New Attitude for Career Success, Earn What You’re Worth, and Girl on Top. She has worked with Fortune 500 companies including LinkedIn, Ford Motor Company, Banana Republic, The Limited, and Proctor & Gamble on hiring, retention & marketing programs. Nicole has had her career advice covered in national outlets such as The Wall Street Journal, The New York Times, Marie Claire, TODAY, Good Morning America & CNN.

What is Loeb NYC's "Company Factory"?

Michael Loeb, Entrepreneur and CEO of Loeb Enterprises

Michael Loeb, a serial entrepreneur, is the Founder and CEO of Loeb Enterprises, a New York City venture capital firm. He and Richard Vogel (COO/CFO, Loeb Enterprises) used their expertise and legacy of success to create Loeb NYC, a privately funded lab. Loeb NYC builds and grows startups from inception to exit. Here Michael Loeb describes his concept for a “Company Factory” and Loeb NYC’s unique Shared Services model.

Michael Loeb quote michael what you have at loeb nyc is uniqueLoeb NYC’s Company Factory

Swinging by Loeb NYC’s Midtown Manhattan office not long ago was a brilliant and remarkably successful entrepreneur, Jonathan Klein. Jonathan and Mark Getty were founders of the eponymous Getty Images. All that company did was revolutionize the stock photo, editorial photo, and film business. With his work largely done – Getty was sold years back to Carlyle for $3 billion-plus. Jonathan serves as Getty Images Chairman, has sat on the boards of two other unicorns since their relatively early days (Etsy and Squarespace), works with various non-profits and advises multiple VC businesses, all while traveling the world to seek out great companies and investments. To be sure, Jonathan has seen a thing or two … but not our model, not once.

“Michael, what you have here is unique, isn’t it?” Jonathan is South African but has lived in England for 20 plus years, so he can be British in tone. So, the quizzical “isn’t it” is at once charming, colloquial, rhetorical, and by turns confounding.

His words were high praise. Our model – a self-funded Company Factory – is, I suspect, accurately referred to as unique. It’s what my partner, Rich Vogel, and I envisioned a decade ago when we concluded that for us Synapse was not the last chapter but the opportunity for a bold new one. What was then a germ of an idea is now burgeoning into full flower.

helen rothberg quote loeb nyc vision

Accelerator vs Incubator vs Company Factory

When described, our factory model sometimes draws comparisons to an Incubator, or its cousin the Accelerator. I describe these as ‘pieces in the middle’: desk space where cohorts of startups or young companies, filtered in by type (adtech, health-tech, fintech, whatthehecktech) are paying tenants for 3 to 12 months, and enjoy, ostensibly, the benefits of sage advice from some grey hairs and community.

What a traditional Incubator is not, is the pieces in the beginning – the ideas, capital or talent. Nor is it the pieces in the end – more and more capital and the exit. For its trouble ‘the house’ gets a sliver of equity and may or may not write a check for a modest $50k or thereabouts. The true value of the incubator model for the entrepreneur? Connections to capital. Famously, Y-Combinator, la creme de la creme, has a queue of VCs – the likes of Andreessen, Sequoia, Greylock – lap up its graduates like Skittles at a Halloween bash.

Add to this the disadvantages of this common startup model. They don’t tell you this in entrepreneur’s school, but founders spend half of their time raising round after round of money, and then more time keeping the money happy. Other hours are spent coding bills, planning payments, nudging receivables, pouring over leases, contracts, and the like. Alas, what about the business building? Um, well, not so much.

Another thing they don’t tell the newbies: the game is kinda-sorta rigged. VCs know that the universal rules of construction apply: the business of building a business takes longer and costs more than the business builders presuppose. Starter-uppers are optimists who ask for too little at first, and upon the re-ask, VCs often invoke the ‘down round’ edict; that is, more equity for less. Ever hear of Waze? A friend and founder Uri Levine told me he owned just 3% of his company when it was it was sold to Google after the VCs had their “waze” with him.

Greedy? Attribute more to odds and probability. Most VC’s will candidly tell you that only 2 startups in 10 have an appreciable return. A little verity from a shot of Casamigos and they will confess to less. Moreover, they are counting – banking actually – on the performance of a rare winner (the most profound of which are fancifully referred to as Unicorns) to pay for all the losers … and their wood-paneled offices, partner mortgages and a long list of green fees.

Shared Services – a Turnkey Solution

By contrast, our model spans the business lifecycle from ideas-to-execution-to-exit. We are self-funded, so our starter-uppers spend not their precious time soliciting investors, but rather soliciting results. Our Shared Services are world-class talent in tech, digital business development, accounting, finance, analytics, data science, promotional design, manufacture and a dozen direct-to-consumer marketing sources, which allows small startup teams to punch way above their weight and have access to capabilities other companies can only dream of.

We think our model is also a magnet for talent. With so many companies in the factory, the odds of collective failure are markedly reduced, and the work is more varied and interesting. The net effect: the chances of success for each company and its rate of growth is markedly increased. The #1 cause of death for a start-up is not the lack of a good idea, it is the lack of capital. But not at our shop. #2 cause of death is dismal execution. But all the less likely with our accomplished and experienced practitioners. I say of us today that once every 5 years we start 10 companies. In truth, it could be twice that number at this very moment, depending on how you count ’em.

‎Another promise of an incubator is a community. But inasmuch as all startups in a conventional incubator are more than a little bit competitive – they share the same physical and metaphysical space after all – not much is collaborative. And that is also part of the dream that Rich and I had: the making of a bonafide entrepreneurial community. A band of start-up pirates, all sharing best practices, and best resources, all participating in the spoils.

michael loeb quote time

Loeb NYC Speaker Series

We believe in giving our staff every tool they need to grow professionally. One of the opportunities for enrichment comes in the form of our Speaker Series. This is a program where “persons of excellence” in any and all fields (from high net-worth business people to actors and dancers), are invited to Loeb NYC to speak. The Speaker Series ramps up in frequency in the summer months, with a weekly guest speaker. This is so that our cohort of paid summer interns can benefit from learning from the successes, failures and philosophies of inspiring and motivating personalities.

Speakers have included Carolyn Everson (Facebook Head of Global Marketing), David Blumberg (Blumberg Capital, one of Silicon Valley’s most prescient Venture Capital firms) Tim Blake Nelson (actor/director), Katie Meyler (a Time Magazine “Person of the Year”) and Damian Woetzel (famous ballet danseur and president of Juilliard School).

When Dr. Helen Rothberg, Intelligence Strategist and Corporate Consultant visited,  she “got” the Loeb NYC vision right away,  “This whole place feels like one big, buzzing vision to me. I was in the “rainforest” and that place is pretty amazing. As an outsider who’s walking in, who’s been to many different companies over the years; Fortune 500, small tech startups, there’s a buzz, there’s an energy, there’s a vision here.” 

The “rainforest” refers to the floor of Loeb Enterprises where all of our startup portfolios are based. The theme was chosen deliberately, as rainforests have the fastest growth rate and highest diversity of species. It is a fertile environment which fosters life, evolution, and renewal.

katie loeb quote shared services

Loeb Enterprises Paid Summer Internship

One of the programs that we are most proud of is our paid summer internship program. In 2018 we received over 1,000 applications and hired 40 interns. The interns gain immersive, hands-on experience in New York City startups and are matched with portfolio companies with which they share a mutual interest and passion. We welcome the contributions, ideas and drive offered by the enthusiastic interns. Many go on to gain full-time employment at Loeb NYC, and have attained positions at our startups like AllTheRooms, Thnks, 3×3 insights and more.

At Loeb NYC we still have much to do. Unique is hard, unique takes time. But we are getting there one groundbreaking startup at a time. And for that, I thank you – our community, our merry, exceptional band – all.

Things You Didn't Know About Bitcoin's Blockchain

Loeb NYC logo hamptons background

Once a speculation point among those involved in startups, finance, or investing, Bitcoin, Initial Coin Offerings (ICO’s), and Blockchain have entered the broader cultural lexicon. You probably have a good idea of the basics and are aware of the social, philosophical, and economic issues, but what follows is a list of things you may not have known about how Bitcoin’s Blockchain actually works.

A slew of Silicon Valley startups and opportunists (some with legitimate intentions, other with get-rich-quick agendas) are raising capital to launch ICO’s on the back of newly invented tokens and cryptocurrencies. A report published by “” in February 2018 and cited by Forbes indicated that, “46% of startups that raised capital via initial coin offerings (ICO) are “dead already…despite raising over $104 million.” and that “The failure rate for ICOs is nearly double that of the one-year failure rate for an average startup going the traditional route of venture capital.” You can read more about inflated Silicon Valley valuations in this blog piece by Loeb.NYC CEO, Michael Loeb.

Despite wild volatility and steep trading peaks and valleys, people are still asking “is Bitcoin still a good investment?” Let’s go back to some basics about the Bitcoin blockchain to gain a better understanding of its underlying technology (which I predict is here to stay, no matter what happens with the value of the coin itself).

1: The Bitcoin Blockchain is a public ledger

Anyone can inspect every transaction that has ever occurred

Here is the very first block #0 in the chain, and here is block #492435. Within each block there are many individual transactions, and the flow of value in a transaction can be explored visually, using tools like this one where we can click through any orange circle that represents a spent value. Because everyone can see every transaction, anyone can confirm that the flow is valid – such that the receiver of value always comes from sources that have sufficient unspent value.

2. Transactions are not from one sender’s address to a recipient’s address

The inputs to each bitcoin transaction in the blockchain are the outputs of previous unspent transactions. So, if Alice wants to send Bob 50 BTC (Bitcoin units of currency), she would do so by specifying one or more of her previous transactions where the total output is more than 50 BTC. This is a subtle but important difference from using Alice’s Chase or Paypal account as transaction deposits are not aggregated into a single identifiable account, and they remain anonymous.

3. Transactions spend all the inputs

In order to efficiently verify transactions, every transaction uses the total value of the inputs and will create a new output address for any change. So for example, if Alice wants to send 50 BTC to Bob and she has 3 prior transactions where she received 25, 20, and 15 BTC, her bitcoin client or wallet software would use all three prior transactions to send 50 BTC to Bob and would result in 10 BTC to a new address as change, and all three prior transactions would be marked as spent and no longer usable.


4. The Bitcoin Blockchain Ledger stores every transaction and is currently ~140GB with over 11k copies in nodes distributed globally

Anyone can start a node, download the ledger, and start verifying and confirming transactions. This makes Blockchain highly resilient to data loss or central control. Natural disasters or individual or company failures will have no adverse effect as long as there are sufficient copies running.

The “Game” of Blockchain…

5. Confirming a block of transactions is a 10-minute guessing game

In order to prevent Alice from using the same coins more than once, all the nodes need to agree on the order of transactions so that once a previous output is used, it can’t be used again.  This is achieved by setting up a difficult guessing game designed to take approximately 10 minutes to win so that a single order of transactions is accepted.

Each player puts together a block of valid transactions that have occurred since the last confirmed block, including the hash of the last successful block, a special transaction to deposit winnings to the player, and a number the player can change called the nonce. The player then runs a hash function over the data and tries to win by producing a hash that is less than a certain target number known as the difficulty. If the hash result is higher than the difficulty, they change the value of the nonce and try again. When a winner succeeds, that block is confirmed and broadcast to everyone, and the game begins again with the next block containing the hash of the last one, hence the name, blockchain.

6. It generally takes a mind-boggling number of guesses to win each game

The process of confirming a block is called mining, and the players are called miners. The combined guessing rate, or hash rate, of all the miners, was approximately 11 million TH/s at the end of October 2017, where 1TH/s is 1 billion hashes per second. At the current difficulty level, this means that it takes an average of approximately 6 billion (10^18) guesses. That’s:




7. The difficulty of the game adjusts every 2 weeks

Since the purpose of the game is to demonstrate Proof of Work and is designed to take 10 minutes to solve, the difficulty of the game is adjusted every 2016 blocks (approximately 2 weeks based on 10 mins per block) in order to keep the length of each game close to 10 minutes. This is done by adjusting the target difficulty number to be higher (easier) or lower (harder) proportional to the amount of time it took to complete the last 2016 blocks being greater or less than 2 weeks.

8. The winner gets rewarded in Bitcoin until the entire 21M prize pool finishes by the year 2140

The first transaction in a newly confirmed block is the reward the miner awarded themselves according to the rules and is called the coinbase. The reward started at 50 BTC per confirmed block and is halved every 210,000 blocks or approximately 4 years. You can see this yourself by looking at block 209999, and then block 210000. This mechanism results in a total supply of 21M BTC awarded, after which there will be no more new BTC entered into circulation. At this point, miners will be paid by transaction fees for their work to confirm new transactions in a block.

9. Confirmed transactions are irreversible

By design, once a transaction is confirmed and added to the blockchain, every subsequently confirmed block creates an increasingly long chain making it virtually impossible to rewrite history and undo the transaction. This results in low transactions costs because similar to paying in cash, there is no need to account for chargebacks.  

10. Proof of Work currently costs more than $1.1B annually, using more electricity than many countries

While the blockchain mechanism is effective in its objectives, it has drawn criticism for the increased use of electricity and resources consumed by an activity that is an artificial means for introducing difficulty and effort. Several alternative mechanisms such as Proof of Storage and Proof of Stake are intended to address this.

If you learned something interesting and would like more information about the inner workings of the Bitcoin Blockchain, I recommend watching this excellent Khan Academy series hosted by cryptographer Zulfikar Ramzan.

Michael Yoon CTO, Investor, Advisor

Michael is Principal and Founder of Yono Consulting where he provides product, strategy and technology consulting services and helps companies like THNKS to design, implement, and scale their products and technology. He is an experienced product management and technology executive with a track record of success in top-tier financial, consumer and technology companies.


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