Yesterday I grabbed Flybridge GP Jesse Middleton on the day they announced their 7th fund for a quick interview. Excited to share what we learned with you!
First, the tl;dr:
- By the numbers: 7th fund, $100 million investing in 10 companies per year with $1-3 million lead checks
- Thesis: Investing in AI companies ranging “from enablement to imagination” based outside of Silicon Valley
- Stage: 1st checks usually come post-product (including some early users/customers), pre-PMF
- Exits: Notables include MongoDB (IPO) and Firebase (acq. by Google)
The firm now has most of its investment team based in NYC, with Jesse flying to Boston monthly while the Boston team comes down a couple times a month. It’s a model that captures both the research depth of MIT/Harvard and lets them tap into the ecosystem of 7,000+ venture-backed companies in New York.
A Unique Sourcing Model
Instead of building a traditional venture scout program, they’ve built four micro-funds with distinct theses:
- X Factor Ventures: 20 female founders backing the next generation
- Graduate Syndicate: Harvard grads backing Harvard grads
- Next Wave New York: NYC tech veterans and community builders
- Next Wave Operators: Big tech alumni (Asana, Google, YouTube) backing other alumni
A scout affiliated with one of those funds can do any deal they like (as Jesse told me: “I don’t have a veto right”), and the scout keeps 100 percent of the upside on the ($50K-$100K) investment.
One example Jesse shared was the scout who heads up Anthropic’s NYC startup program. She spots a promising founder before they’ve even incorporated, writes a check through one of the scout funds, and Flybridge gets 3-4 months to build a deeper relationship with that founder.
Founders Have It Their Way
Most VC pitch meetings look the same, and most founders get to that point in the same way. Founder builds deck. Founder sends deck. Founder meets one investor. And if that goes well, founder pitches partners.
That last part? It’s quite different at Flybridge versus other VC firms, as I found out from Jesse. For example, before the team meeting, founders get bios of everyone who’ll be in the room. No surprises, no power games. Just: how can we meet you where you are?
Another example:
What is your style of pitching? What makes you most comfortable? You want to be on video or not? Do you want to present or not? Do you want less people in the room or more?
And that “partner” pitch isn’t just the partners. Jesse specifically mentioned their CFO and head of community as regularly attending those pitches.
A Personal (Burrito) Story
No, that’s not an AI hallucination. There is actually a burrito involved in my first memory about Flybridge. And yes, this does relate to the interview with Jesse. Let me explain…
Back when I was an post-MBA associate, I was tracking a startup called 10gen. Which now we all know as MongoDB. 10gen had a great founding team (who started and IPO’d DoubleClick) and awesome tech, but product-market fit wasn’t there yet. And it was time for them to raise again.
Somehow I managed to get a meeting with one of the founders, Dwight Merriman — at a now defunct burrito joint near Union Square. Dwight politely entertained my questions and left the door open to continue the discussions. And like the rookie investor I was, I decided for a multiple reasons that I wasn’t going to pursue it.
Oops. Soon after that, Flybridge announced that they were making an investment in the company. And the rest is NYC startup history.
I brought the MongoDB pivot up with Jesse in our interview. Although it happened before he joined Flybridge, it led to a discussion highlighting one of the advantages founders may get from having an established firm like Flybridge in their round. It’s not just about the check. It’s about pattern recognition. Or as Jesse said:
One of the advantages we have is we see thousands of companies… what are the few things they got right, what are the few things they got wrong?
The Venture5 Take
Put it this way. I took a break from editing this post to refer one of my angel investments to Jesse. It had nothing to do with the interview and had everything to do with the reputation he and the firm have built in the ecosystem over ~20 years.
If you’d like to learn more about Flybridge’s new fund, you can read the the official announcement linked here.
