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."

Investing:

“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.”

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

To subscribe to my podcast on Venture Capital in NYC via #iTunes https://itun.es/i6S78vQ or Soundcloud https://soundcloud.com/venture-studio

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!

Dave