Bringing Wine Into the 21st Century

I’m Philip James, Founder and CEO of Penrose Hill – a wine company aiming to bring the wine industry into the 21st century. At Penrose Hill, we rely on data analytics to gain unconventional perspectives into a somewhat conventional industry. We want to see things in new ways, especially if it allows us to eliminate inefficiencies so that we can provide consumers a better product for a better price.

Turning Data Into Wine

Data is at the heart of what we do. We use feedback from our 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 our customers exclusive access to small-batch wines for less, while delivering higher margins to our partners.

bottle of wine with toy truck

Firstleaf Wine Club

There are three distinct branches driving our company’s growth. The first and largest being the Firstleaf wine club. Penrose Hill’s goal is 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. Even with this incredible tool, we’re constantly innovating new ways to connect our members with great wine.

penrose hill bottles and audience match

Direct-to-trade Wines

The second branch driving our growth is a line of direct-to-trade wines. We are diversifying our sales base by venturing into the biggest segment of the wine market: traditional, distributor-driven sales to retail and restaurants. Leveraging the savvy we gleaned from market testing from Firstleaf, new packaging options and dynamic customer experiences allow us to breathe new life into this segment of the industry. We are introducing several new brands in 2018. Our canned wine Right Now Red no. 8 is already in some stores in New York! We made it to be enjoyed anywhere you are – perfect for a busy city.

canned red wine

Another of our 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 we only source from exciting and distinct wine regions, in an effort to highlight our interconnectedness through the land.

Corporate Partnerships

The third branch of our company is corporate partnerships. We have been working to launch wine clubs and build labels for brands interested in diversifying their client outreach. A really fun “Loeb family” partnership we have just completed is with the team from Thnks!

Wine Pairing Advice

I thought it would fun to end with a little 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.

three people with wine glasses and wine bottle

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.

Interior driverless cars

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.

inside 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.

When 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 at SxSW

Loeb NYC logo forrest background

While 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.

Here you will find a lively conversation between Michael Loeb and Gary Vaynerchuk, moderated by Bonin Bough.

Additionally, we hosted the Real Inclusivity panel, in which 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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Speakers Series: Crypto’s

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.

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.

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.


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

What can be done about Offensive Content on Social Platforms? Content moderation on social media is a weird pet obsession of mine. The internet is full of garbage, 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 too.

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.

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 diletantes 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 three reasons why no major social platform has “solved” abuse:

  1. The valuation of social media platforms depends on discovery capabilities and wide, active social graphs.
  2. Many (most?) major platform founders and top brass genuinely believe in unmitigated discovery and free speech as universal 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 on 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 (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

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”.  

A Herd of Unicorns

In 2016, the VC ecosystem echo-chamber fabricated 160-something unicorns, a.k.a startups with billion-dollar-plus “valuations” (why the quotes? Read on). 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. 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, 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.   

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 view. To be sure, the market puts a premium on innovation, novelty and first-in-market positions – that is where you find big growth and 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 (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.  

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.  


Office Culture and Startup Success

Is establishing an office culture important 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 are 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.

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.

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.

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 Entrepreneurs’ 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 is 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 Entrepreneurs’ 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. 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?’  

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.

Entrepreneuring is a total-brain full-contact sport. Be shy and die; delay – you’re 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 is 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, 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 to an adoring crowd, the16th 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 some place between a paradox and a contradiction. But for my money, it comes down to this: the entrepreneurs’ gene.

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 this year’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

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 to 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.


10,000 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 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

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

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 them 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 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.

Our Company Factory

“Michael, what you have here is unique, isn’t it?”

Swinging by our 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 into full flower.

We rejected the incubator model

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 start-ups 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 for this common start-up 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? 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 start-ups 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.

Unique ‘Company Factory’ model

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; world-class talent in tech, digital business development, accounting, finance, analytics, data science, promotional design, manufacture and a dozen direct-to-consumer marketing sources, allows small 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 community. But inasmuch as all start-ups 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.

We still have much to do. Unique is hard; unique takes time. But we are getting there one groundbreaking start-up at a time. And for that, I thank you – our community, our merry, exceptional band – all.

Michael Loeb CEO and Founder

Michael Loeb, a serial entrepreneur, is currently the President and CEO of both Loeb Enterprises (LE) and Loeb.NYC. He knows success, past and present. Loeb.NYC, Michael Loeb’s privately funded venture lab leverages his expertise and vision to build prosperous companies from the ground up. World-class analytics, design, marketing, and tech-development pave the way to rapid growth and significant scale.

Bitcoin: Things You Don’t Know

Loeb NYC logo forrest background

If you’re involved in startups, finance, or investing, you have likely heard of Bitcoin, Initial Coin Offerings (ICO’s), and Blockchain. You probably have a good idea of the basics and are aware of the social, philosophical, and economic issues. Here are 10 things you may not have known about how Bitcoin’s Blockchain actually works:

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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