Episode 24: Master Class on Enterprise Investing (Eliot Durbin)

In just seven years of operating, Eliot Durbin and Ed Sim (pictured above) have established Boldstart Ventures as one of the sharpest funds in the city with a specific focus on enterprise. I recently got the chance to talk to Eliot about the fund’s origins, “the scars on his back” from the early years, and the unique nature of investing in B2B startups.

We were also able to delve into some of the trends that Boldstart is most excited about in 2016, including Smart Data, Saas 2.0, and the Googleization of IT. Eliot shared some further insights on working with serial entrepreneurs, the rise of “shadow IT,” and the implications of increased decision-making power for engineers in big corporations. Over the course of the discussion, it was easy to see how Eliot’s precise, thematic thinking has influenced Boldstart’s growth, benefited their portfolio (including Divide, Rapportive, and Handshake) and the New York tech ecosystem generally.

Shadow IT and engineers being the end-customer for enterprise startups: (20m)

“There are entire companies that have been created to address Shadow IT."

“If you’re Procter & Gamble, you’re developing software…almost every company that’s publicly traded has to develop software in some way shape or form…The folks that are driving that acceleration and that efficiency in the enterprise are the engineers.”

On serial entrepreneurs:

“I love the longer term founders who are on their second or third companies… there is something special about backing a founder a second or third time… They come back and say, ‘Ok, now I have a really big idea.’"

The uniqueness of working with enterprise companies:

“We built BOLDStart with a purpose, to be the best seed fund for enterprise companies."

“If you’re thinking about a solution to a big problem that you have, and you’re considering leaving your job to start that company, we want to talk to you."


“It’s kind of like golf, you get better over time. You got to just keep playing the game."

Episode 22: On Debunking Venture Mythology (Paul Martino)

In this episode of Venture Studio, we hear from Paul Martino. He is the founder and General Partner at Bullpen Capital (one of the pioneers in post-seed round funding) and has a way of thinking and talking about the venture ecosystem that is uniquely his own, and unapologetically contrarian.

Paul founded Bullpen in 2010 and his data-intensive approach to investing in companies such as FanDuel, Namely and Life360 has resulted in what will perhaps be one of the all-time great first-time funds.

Prior to starting Bullpen Capital, Paul was the founder of four companies and an active angel investor in companies such as Zynga, TubeMogul, uDemy, and PayNearMe.

Paul and I cover a lot of ground in the episode. In his infinitely quotable manner, Paul talks about how the herd mentality of most venture investors presented a huge opportunity for Bullpen, discusses how to effectively manage your board, and shares some insider experience on what it's like to be coached by the legendary Bill Campbell, (behind-the-scenes guru to Jobs, Bezos, Brin, and so many of the Valley elite).

Some of the most memorable quotes were:

On raising money:

"Once you get ten ‘no’s’, you know you're going to get 50 ‘no’s'"

"Don't be 10% better, be different.”

On the problem with traditional funds:

“Many funds are momentum players and when the music stops they go home and don't do any deals…[they’re] already playing golf.”

On the people doing it right:

“Floodgate, First Round, Felicis and True, these are three or four of the absolute best seed funds… those funds are the next great generation…Those funds will be the names in the pantheon.”

On learning how to be a CEO from the great Bill Campbell:

“Being a CEO…is lonely, it’s scary.”

“One of the things he said in that first meeting [I had with him] was, ‘CEO’s get paid for judgment. Do you think you’re good at that or not?…Two to three times a year you need to tell your board of directors that they’re 100% wrong.’”

“[You need to ask yourself:] what are you uniquely qualified to do in this particular business? Is this something you were born to do?”

“There are certain kind of people, I don’t care how much money you make or how successful you are, you kinda still have that hard-work, blue-collar, chip on your shoulder mentality. That’s who Bill is, and that’s absolutely who I am.”

On Bullpen’s subversive strategy:

“We [Bullpen] ignore venture mythology…we do the deals that people are scared to do.”

“VC suffers from a herd mentality…[But] it’s so much more fun to make money when you're right being contrarian than when you're 10% better than anybody else.”

“Almost all of our deals have a little bit of a contrarian streak to them…when everyone’s in the category, that’s exactly when we don’t want to be there.”

"Most venture people wake up in the morning and go ‘I’m gonna go to Y Combinator’s [Demo] Day, and the prettiest company at the dance is the one I’m gonna invest in.’ That is the opposite of what I’m gonna do.”

“I conceived of Bullpen as a bear market fund…the fact that we made this work as well as we did in a bull market, is in some ways the surprise. This is the market condition we always assumed where our fund would flourish.”

Episodes 18 & 19: Bitcoin Jesus (Roger Ver)

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I recently spoke with Roger Ver, entrepreneur, bitcoin investor, bitcoin evangelist, and voluntaryist. If you thought we were just going to talk about bitcoin on this episode, think again.

Roger Ver, nicknamed “Bitcoin Jesus” is a fascinating guy. Credited as the first person in the world to invest in bitcoin startups, he’s been the leading voice and catalyst in bitcoin ecosystem for years. Why? according to his website, Bitcoin is the most important invention in the history of the world since the internet.

In part 1 of our two-part series, Roger and I discuss why people should care about bitcoin, a few companies that are accelerating mainstream bitcoin adoption and why bitcoin is a non-political means to freeing up the entire world’s economy. We take a quick foray into macroeconomic and government theory and then, for good measure, we’ll talk about George Washington, Vietnam and World War 2.

In part 2 we picked things up right after Roger began to describe how and why he renounced his US citizenship. I asked Roger about the repercussions of his actions and beliefs, including his 9 month stint in federal prison. After discussing the justice system and unauthorized explosive sales, we reeled it back to bitcoin by digging into blockchain, fixed supply and some predictions for 2016.

Whether you agree with his views or not- Roger is truly a person who has walked the walk. He's a pioneer and thinks completely for himself and lives by his own credo. Not something you see to often these days. I really enjoyed this conversation and hope you do as well.

Episode 17: The Woman who runs the largest Seed Fund in World History (Ming Yeh)

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I learned a lot from my recent conversation with Ming Yeh. Ming is a long-time veteran of venture capital and is now co-founder and managing partner of CSC Upshot Ventures, the largest fund dedicated to financing seed-stage startups, ever.

This launch was a big deal indeed. CSC Upshot is a $400MM venture fund created to invest primarily in US seed-stage technology startups via AngelList. It’s biggest LP is CSC Group, one of China’s 3 largest private equity firms, with $12B under management.

Now that the words “$400MM” and “AngelList” have sunk in, lets dissect this a bit. Earlier this month, you learned about the Angel List’s Syndicates product in our interview with Dustin Dolginow of Maiden Lane. Today, we dig further into the massive opportunity. Some stats: as of October 2015 (when CSC Upshot was announced), AngelList Syndicates had helped over 650 companies raise $205MM from 4,400 individuals and Maiden Lane’s $25MM vehicle. Now, CSC Upshot joins the Syndicates ecosystem with a fund nearly double the size of all Syndicate activity to date.

In this episode Ming and I talk about CSC Upshot, the need for more liquidity at the seed stage, the difference between Chinese and US entrepreneurs, and whether we’re seeing the great unbundling of VC or just a natural evolution of the venture financing market.

Episode 16: A Deep Dive into AngelList Syndicates (Dustin Dolginow)

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We recently welcomed Dustin Dolginow to Venture Studio. Dustin a co-founder of Maiden Lane Ventures, the first institutional venture fund built for AngelList Syndicates.

Here’s an excerpt from Maiden Lane’s AngelList page: "Raising seed capital is unnecessarily complicated. Great angel investors have always helped founders cut through the noise. Maiden Lane's mission is to make partnering with world-class angels more impactful. To do that, we use capital and software to rethink the workflow of seed investing."

Seems pretty logical, right? Maybe even a bit boring? Well, not really. Syndicates and funds like Maiden Lane have been called, progressive, disruptive, cute and fraudulent, and everything in between. Today, we’ll learn why.

Dustin and I discuss the facts behind Syndicates, the massive opportunity for individual investors and founders that Syndicates presents, and the support, critiques and criticisms from others in the venture capital industry.

We also talk more broadly about how thought leaders like like Chris Sacca, Brad Feld, Paul Graham and Mark Suster have approached innovation and unbundling in venture capital.

This episode is just the first installment of our series on AngelList Syndicates. We'll soon catch up with Ming Yeh, Founder and Managing Partner of CSC UpShot Ventures, a $400 million venture fund formed to invest in startups on AngelList.

You can find Dustin on AngelList (obviously) and on twitter and Medium under @dolginow.

Venture Studio Rising


As of a few years ago and well before podcasts had become "a thing", I was doing video interviews of entrepreneurs and investors regularly on my show-  Venture Studio. A confluence of factors led me to put the show on hold for a while, not the least of which was the unexpected and deeply painful loss of my father. I have my own family with young kids and have also been looking after my mom, who has had a tough time adjusting after 50+ years of marriage to her best friend. Recently though, I noticed that podcasts had really gone mainstream with the advent of bluetooth-enabled cars, ease of production, new podcast apps with great UX (such as Overcast), and talented media people switching to "podcast first" (such as Bill Simmons and the Gimlet Media team).  I started thinking about reprising the show as a podcast with more of a focus on investors. With the encouragement of a terrific former student of mine- Kevin Weeks, Venture Studio rose from the ashes a couple of months ago in its new incarnation as a podcast. It's been incredibly gratifying to experience the support and encouragement from so many of you and I'm happy to say that with just 15 episodes in, the growth of the show on this medium has been just terrific. Kevin is crushing it as the producer of the show and I'm able to concentrate on what I love doing- interviewing the talented and thoughtful guests that comprise the investment community of New York City and beyond.

So I just want to thank everyone who has subscribed and is listening for the support. I also want to thank the incredible guests who bring such rich insights to the conversation. So huge thanks to @davetisch @benlerer @mattcharris @jeff @bopeabody @john_frankel @amol @alexiskold @joannewilson @stephpalmeri @mikeyavo and @cshapiro .

If for some reason you haven't checked it out as of yet or know of a friend who would enjoy our show please share this link with him or her and/or subscribe here.

I'm really looking forward to taking things to the next level in 2016. I hope you can join the community.

Happy New Year!


Episode 9: the one and only Gotham Gal

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I recently had @thegothamgal, (Joanne Wilson), on my podcast. She's a true original- one of a kind- just special. She's also a prolific angel investor in New York, (85 companies and counting), and a major supporter of the city’s startup ecosystem.

Joanne began angel investing in New York after careers in retail, wholesale, media, non-profit, education and real estate. Very few investors can match the deep understanding of "the customer" she brings to the teams she decides to back. I learned a ton from our conversation.

Joanne blogs regularly at and you can find her on twitter @thegothamgal. She is an outspoken supporter of women entrepreneurs and the co-founder of Women Entrepreneurs Festival.

I hope you enjoy and learn as much as I did.

Episode 7: the fox and the hedgehog: my talk with Amol Sarva

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A fox knows many things, but a hedgehog knows one important thing

In a recent episode of my show, Venture Studio, I spoke with one of the most fascinating people in the New York technology/entreprenurial community, Amol Sarva, on a wide range of topics. We spoke about his life not just as a company builder, (for which he is widely known), but also about his approach to angel investing. He's in 38+ companies already and it was fascinating to learn of his philosophy and approach.

At one juncture Amol, (who has a Phd in philosophy from Stanford), refers to an ancient parable attributed to Archilocus, which philosopher Isaiah Berlin wrote an essay about in 1953. The fragment read, "a fox knows many things, but a hedgehog knows one important thing". Amol realized close to a decade ago that he identified with the fox, even though everything in his upbringing and education had trained him to be a hedgehog.

This realization has led to an immense creative and productive period in his life in which he's co-founded several startups such as Halo Neuroscience (backed by Andreessen Horowitz and others), Knotable, BEMAVEN and Knotel, constructed a building in Long Island City known as East of East and invested in 38+ companies. Of course this is alongside his family life as a husband and father.

Prior to all this he co-founded Virgin Mobile USA which went public on the NASDAQ and Peek (which pioneered the mass-market smartphone), which he sold to a large Indian conglomerate. He studied cognitive science for his Ph.D. at Stanford with an undergraduate degree from Columbia University.

Amol blogs regularly at and you can see a list of his investments at His personal website is Follow him here on: twitter

Enjoy our conversation just below and please share via twitter if you enjoy

Sign-up for my podcast: Venture Studio


Friends- if you're interested in the venture capital and angel investing scene in NYC, subscribe to my podcast via iTunes:  and/or listen to us on SoundCloud: . For regular updates, follow us via twitter: @venturestudio My show has been around since 2011 but is now available in podcast format so you can listen while you walk, jog, drive, train, or rest on a couch. It will also come with a short summary of the venture deals in NYC so you can stay abreast of everything easily.

There are a few vintage episodes up already with the likes of Matt Harris from Bain Capital Ventures, Jeff Clavier of Softtech Ventures, Bo Peabody of Greycroft Ventures, Dave Tisch of Box Group and Ben Lerer of Lerer Hippeau Ventures.

Enjoy and please email me some feedback once you've signed up!