How Entrepreneurs Can Get David Bookspan’s Attention

David Bookspan (Photo courtesy of DreamIt Ventures.)

Sitting in a coffee shop with David Bookspan, I wish I had a business idea to pitch. After all, he’s a founding partner of DreamIt Ventures, a $30 million venture capital fund in Philadelphia that’s sprung success stories like Meerkat, SeatGeek and LevelUp.

We spoke at length about how he handles all the entrepreneurs clamoring for his attention, the importance of keeping DreamIt companies in Philly, and the criticism that DreamIt isn’t encouraging its alumni companies to work together. He even revealed some embarrassing professional failures (like a Hollywood Fantasy Camp.) For a guy who’s so sought after, he comes off as very approachable, soft-spoken and generally nice. We even talked baseball for a while after our interview.

BizPhilly: Is it hard for an entrepreneur to get a meeting with you?

Bookspan: I handle it in two ways. If it’s an introduction through somebody I’m close with, I’ll take that meeting. If it’s somebody I don’t know and they’re very persistent, I tell them I’ll be at various events throughout the month in Philadelphia and they can find me there for a few minutes. The DreamIt companies, of course, have unfettered access. That’s where I spend most of my time.

BizPhilly: When an entrepreneur does get your attention, how can they keep it?

Bookspan: If you can wow me in a sentence, that’s a great thing. If somebody is giving a pitch and they are taking a long time to get to the punch line, I’ll try to help them along. But it’s a real high-class problem that we have since there are so many people that want to start companies and have ideas and who are really passionate about what they’re doing.

BizPhilly: How do you respond to the criticism that DreamIt doesn’t encourage its alumni companies work together? 

Bookspan: I think it’s fair and I think it’s something we need to work on. We haven’t been leveraging the alumni community among each other and for the benefit of DreamIt like we need to do. I think the criticism is appropriate against DreamIt with regard to a lot of the companies. We have to do a better job of inventorying what’s available for DreamIt companies from the portfolio itself. That includes sourcing mentors for companies. We now have a group that’s over 600 entrepreneurs. It’s tough to manage, particularly when we haven’t been historically focused on generating revenue for DreamIt. Alumni networks take capital and people to organize, but we’re trying really hard to up our game in that area.

BizPhilly: How important is it for DreamIt to keep companies in Philly?

Bookspan: Personally, it’s important for me. As a DreamIt mission, the companies need to go to places that serve their needs best. Typically, what we found is that companies follow capital. One of things we’re looking at and trying to switch around is that I believe capital will follow customers. I think it will be a long time until Philadelphia can compete with the Valley, New York or even Boston on capital for early stage. But we might be able to do better at connecting companies with customers — then the capital will follow the customers and companies will be more likely to stay.

BizPhilly: When evaluating companies to invest in, what is DreamIt looking for?

Bookspan: The overarching principle for accepting companies into DreamIt is: Can they achieve an important commercial milestone within the period that DreamIt is running. In the case of DreamIt Tech, that’s three months. For DreamIt Health that’s four months. Can they achieve a commercial milestone that they can leverage past DreamIt? Because it’s fly-or-die during DreamIt.

BizPhilly: What’s your biggest professional failure?

Bookspan: There have been lots. I’ve tried a bunch of things. Things as silly as Hollywood Fantasy Camp. It was an idea I had with Mike Levinson [founding partner at DreamIt] — I’ll drag him into this with me. He and I talked about starting a fantasy camp that’s like a baseball fantasy camp but for Hollywood. It was stupid. You would go with actors being your coaches and you would produce a film or a play in a week. It never got off the ground. We actually got the idea in front of John Travolta but he passed on it. We also got it in front of Jamie Lee Curtis and she had some interest that was charity connected, and we wanted it to be a for-profit. Perhaps a fun business but not one that has tremendous commercial viability.

Another idea centered around doing a TV show that would showcase Philadelphia bands, trying to showcase the Philly sound.

My greatest professional failure, though, is that I wanted to be a professional baseball player. I pitched in the semi-pro Spanish Federation of Baseball Leagues.  I was pretty good in high school, my college did not have a baseball team — even though they promised they would. So I went back after college to play ball. The slider which was a pretty good out pitch for me in high school. Our claim to fame was that Caroline Kennedy used to come to the games. She was dating one of the other three gringos on the team. She wasn’t there to watch me.

BizPhilly: What advice do you have for entrepreneurs starting out?

Bookspan: We really encourage companies to sell it before they build it. Get out into the market. Use wireframes, prototypes, mockups — whatever you’ve got — and go into the market and see if you can sell it. See if you’re building something that anybody cares about. If enough people care about it, it can be a viable, scalable commercial business.

BizPhilly: What are some of the most successful DreamIt companies?

Bookspan: We love all our children equally. But if you’re talking about financial success based upon what investors have put a lot of money behind, you can look at Meerkat, SeatGeek, LevelUp and Adaptly. Those are the companies that have gotten the most investment.

But that’s not the only measure of success. We’ve had companies like Tidal Labs that have taken no money from outside investors and are doing well.

BizPhilly: Do you watch the show Silicon Valley and is it an accurate portrayal of the startup world?

Bookspan: I do. I love it. There’s so much inside baseball in that too. It’s a total caricature. I’m not embedded in the Valley, I’m not living that life, but a lot of friends and people I’m aware of are. The stories that they use as plot lines, in many instances are based on real events that have happened.