VCs Would Bet on Open-Source AI Over OpenAI and Anthropic | E2341

Jason Calacanis (0:00)

All right, everybody, welcome back to This Week in Startups slash This Week in VC. We are every week trying to do a This Week in VC panel.

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Jason Calacanis (0:45)

And my Lord, we've got an incredible panel here. I'll call this old school. Jeff Clavier is here, my old friend, founding partner, Uncork Capital. Jeff, how are you doing?

Jeff Clavier (0:58)

I'm good, thanks for having me. How are you doing? It's been a while.

Jason Calacanis (1:02)

It has been a minute. You and I have known each other for three decades, I think, since the early 2000s. You started in Venture Capital when?

Jeff Clavier (1:09)

In 2004 I mean, 2000 as a traditional VC, 2004, I kind of started the whole seed craziness.

Jason Calacanis (1:18)

Yes, you were there early. I think it was you. Let's see, first round capital came after you in that same zone?

Jeff Clavier (1:27)

We sort of started around the same time with Josh. They were raising like vintage funds every year. I raised one of the first seed funds in history in 2007 after being like what they called at the time Super Angel for three years.

Jason Calacanis (1:42)

Yes, so there was Super Angel, which meant you did more than a couple of checks a year and you might have had LPs. Then we had the, I think we called it micro funds or micro VC early, some people did.

Jeff Clavier (1:55)

For a few months, they called us Super Angel funds and then Mike Maples came up with the term seed. I think he kind of invented it. And starting, I guess 2007 or 2008, they called us seed funds.

Jason Calacanis (2:11)

What size was the first fund?

Jeff Clavier (2:12)

Well, the first fund was $15 million and you made fun of me on the TechCrunch 40 stage because we announced it together on September 12th of 2007

SPEAKER_2 (2:25)

Check out the elephant here. Yep.

I think I'm the elephant in the room.

Dave McClure (2:29)

He's got receipts, baby. Better watch it.

Jeff Clavier (2:32)

And you were like, who the hell sort of raises a $15 million fund makes no sense. But good luck to you.

Dave McClure (2:38)

I mean, it's not exactly what you said.

Jason Calacanis (2:40)

You were an innovator.

SPEAKER_2 (2:41)

What were the sizes of the rounds that seed back then?

Jeff Clavier (2:44)

When we invested, you know, 250K in a million dollar round, it was actually a pretty standard round. Fitbit in 2008 raised a $2 million seed round. It was massive, massive.

Jason Calacanis (2:59)

And that was at what kind of valuation? Like an 8 million post, a 7 million convertible node?

Jeff Clavier (3:04)

It was five pre.

Jason Calacanis (3:05)

Five pre. There you go. Right in that zone. Jenny Fiedling is here.

Also been in the business for a while. How did you make your first investment?

SPEAKER_2 (3:15)

That's a good question. I was a founder and I did a little angel investing. And then I was working on my third company and I ran into the founders of Techstars, David Cohn and Brad Feld. And they said, what do you think about being on the other side of things?

So I thought, oh, maybe I could like incubate my company, learn a little bit on the other side. And I ended up really loving early stage investing and stayed there for seven and a half years running Techstars New York.

Jason Calacanis (3:41)

Yes, and this was in the time period where each of those Techstars had like really amazing leadership and they ran like in this affiliated network. Think sometime during COVID, they consolidated, put a CEO in charge. It didn't work out. They may have broken up that federation and it got a little dicey. But tell us about the golden age there of Techstars.

SPEAKER_2 (4:09)

I started like 2013-14 and actually this is so funny. I have my little mug from my accelerator. I had two unicorns in this class.