Jesse Middleton

Looking forward to finding somebody amazing to join our small but mighty team here at Flybridge. www.linkedin.com/jobs/view/42...

I'm happy if you want to share a little bit more color about "Why you", but we want to run a good process here, so please apply to the job post below. You can send a more detailed note to jesse+cos@flybridge.com after you've submitted the application.

I'm really excited to loop the right person into everything that I'm working on and that our team is doing over the coming years.

If you know somebody who'd be an amazing fit, send them here and ask them to apply over on LinkedIn (link in the next Tweet).

I want this person to be the "COO" to my CEO brain. You should be:
• Detail-oriented and amazing with people
• Passionate about startups and learning the venture business
• Excited to work with some of the smartest and most driven founders in the world

I couldn't be more excited to finally share that I'm hiring a Chief of Staff to join me at Flybridge. This person will work side-by-side with me here in New York every day and will get to join board meetings, pitches, LP meetings, and everything in between.

Assuming this T1 phone is... not made in America.

I'm grateful for people who accept me as I am, including Jeff, Chip, and Cat. You teach me more every day.

P.S. Today is also my parents' 43rd wedding anniversary :)

Happy Friday!

I encourage the entrepreneurs I back to prioritize their wellbeing. Startups are challenging enough when you're at your best.

Sobriety has taught me to be fully present. Flybridge has taught me to trust my instincts. Together, that’s a powerful combination.

Instead of micromanaging, they told me: "You'll be here longer than us. Start making the calls." That level of trust changed me.

The experience shaped how I work with founders. While everyone talks about work-life balance, most of us struggle with it.

Sobriety taught me that the strongest relationships don't require alcohol.

From my first day at Flybridge, Jeff and Chip demonstrated this. They focus on meaningful work and authentic relationships with founders.

Today marks 3 years sober and my 9-year anniversary with Flybridge.

For years, I thought drinking was essential to my job. Happy hours...client dinners. I believed that's how business relationships were built. But those moments came with hidden costs I didn't anticipate.

Generic AI contract review is commoditizing fast. Fully-captive workflows are still rare. LP documentation is rule-heavy and repeatable. That’s ideal training data.

Distribution:

Half of Covenant’s early adopters sit within three subway stops of our office. Jen’s network supplies the first ~20 customers. Product proof handles the next >200.

Market size:

The niche legal spend is “only” $5 billion, which keeps platform tourists away. Own 20% and you’re running a billion-dollar ARR business with near-zero churn (LPs rarely switch counsel mid-fund).

Ingest LP documents → LLM reviews every term → output a signature-ready closing binder.

Why buyers care:

• Speed: hours, not days
• Consistency: once tagged, never missed
• Cost: ~90 % below big-law

Across U.S. institutions, that line item added up to roughly $5 billion last year. Covenant automates that narrow yet stubbornly expensive workflow.

How it works:

A single endowment can burn six figures a year on lawyers just to confirm that a private-equity subscription agreement matches the side letters it already negotiated.

Love how accessible Uber is but riding in a Waymo is like seeing into and riding in the future. It’s as close as we have made it to teleportation yet. And it’s basically the same price as a human driving you erratically through the city.

I have no idea if they know it or will remember it but it makes me feel like in a crazy world where we have little control, from day to day, there’s this tiny period of time when it’s just us, together, and complete. 💜

I don’t know where I got this from but every night I put my kids to sleep I say, “You are safe. You are loved. You are mine. And I am yours forever and always.”

What a magical idea and execution. Started a small Dad Group in NYC but we’re not cool enough to have merch just yet. 😏 Entrepreneurs, VCs, designers, chefs, and dentists all come together though.

I’m off to Amsterdam this evening to meet LPs, GPs, and some brilliant European founders. Who should I meet while I’m in town? Tag one person who’s at the top of your list.

P.S. I’ll be missing these three while I’m gone. 😔

The main caveat is ensuring that you’re still strategic about where you incorporate or how you handle local regulations. You can’t be sloppy about that.

The world isn’t small, but it’s definitely more connected than ever.

Or we see a founder from the Bay Area who flew out to New York just to pitch in front of an AI-focused crowd. It’s a more fluid world. They adapt. We adapt.

For me, I like how this expands our investment lens. We can back a company headquartered in New York, but maybe their entire engineering team is in Argentina.

I remember when I first started investing years ago, that was pretty rare. Ten years ago, you’d have the occasional international team, but we still expected them to open a U.S. office or relocate to get serious capital. Now, if you have real traction and a crisp product, your zip code matters less.

Everyone’s comfortable with virtual collaboration, recruiting talent wherever it is, and selling to customers who might be on the other side of the planet.

This also shows up in where we source deals. I’ll talk to a founder in Singapore via Zoom in the morning, another in Berlin in the afternoon.

Now, it’s almost normal to see a founding team of five people scattered across three countries.

Partly that’s thanks to remote tools, but partly it’s a shift in founder mentality.

an airplane is flying over a globe with clouds ALT: an airplane is flying over a globe with clouds

One big trend that’s really sticking post-COVID is how companies today, especially early-stage startups, now think globally from day one.

It used to be you’d build in New York or the Bay Area, maybe branch out later.

Last night’s #CornellTech @ Bloomberg speaker series featuring Jesse Middleton, General Partner at Flybridge, in conversation with Isabelle Lee, Cross-Asset Reporter with @bloomberg.com, revealed valuable insights into venture capital, AI, and the future of work. @jessemiddleton.com #CTechBBG