Jesse Middleton @srcasm

In 2024, the conversation was all about models. In 2025, it shifted to agents. This year, it feels like it’s finally about the people driving the technology forward. That’s why Flybridge is hosting one of our favorite events of NY Tech Week, The 100 Women in AI Celebration. • Date: Thursday, June 4th • Time: 6:00pm - 9:00pm • Location: New York, NY (Get on the list for full location details) While the room is mostly reserved for the honorees, we saved a handful of spots for the broader tech community. If you’re around for Tech Week and want to join us, drop a comment below and I’ll send over the invite link.

Super fun day today! @Flybridge completely took over a local bodega, handing out free BECs while founders pitched us their startups. We had a dozen VCs and a couple hundred entrepreneurs pack the space. We even got to pay it forward by serving free food to the neighborhood regulars. Tonight, I’m heading over to the Pitch Roast show. Text me if you want to snag some last-minute tickets! Or just DM me :)

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@roseajohnson @flybridge @AWSstartups @sasyrae The most entrepreneurial of the bunch are going to take those tickets you took a picture of, print some more, and try to show up before our event finishes :)

Alright @flybridge and @AWSstartups win the title for ‘most NYC’ event of the week. Bodega takeover was 10/10 @sasyrae @srcasm

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I’ll be at Pitch Roast Live this Wednesday for #NYTechWeek. Instead of sitting safely in the audience, I’m stepping in as one of the investors for the night. I'll be reviewing pitches from 4+ brave founders while comedians Dan Toomey, Sienna Hubert-Ross, and Troy Bond roast all of us live on stage. It should be a good time, mostly because I’m fully expecting to get torn apart 😂. Cocktail hour is at 6:00 PM, and the show starts at 7:00 PM. I have a code for a handful of free tickets. If you want to come out and watch, comment below and I’ll send it over.

@brlands @salesforce @OpenAI @SlackHQ 👏 👏 👏

@Emily_Sundberg This should be fun. partiful.com/e/NhoyBpx8rlyJ…

NY Tech Week is here! I’m organizing a few events with the Flybridge team, but my main goal for the week is actually to keep things low-key. If you’re in town (or live here) and building in the AI space, I’d love to connect. We’re actively investing out of our 7th fund at Flybridge, typically writing $1M to $3M checks for teams building AI infrastructure, agents, and prosumer applications. I'm particularly looking to chat with founders working on: • Invisible Infrastructure: The safe, auditable plumbing that makes autonomous systems reliable enough for enterprise scale. • Outside the Chat Box: Voice-native and next-gen interfaces, like a task manager that can turn a brain-dump into something clean. • Deep Vertical AI: Founders tackling messy, non-linear problems (like healthcare or finance) because they have deep, lived insight into the space. Drop a comment below or slide into my DMs to grab a coffee while you're in town. Let's chat 👇

Borrowing this entire post from the one and only @sasyrae… Next week at #NYTechWeek I'm going full Bodega Baddie. @Flybridge, in partnership with @awscloud, is hosting "Pitch VCs, Free BECs," a full Bodega takeover. It's time we add some authentic NY vibes to TECH WEEK by a16z! If you're a founder, you'll have the chance to pitch early-stage investors from Flybridge, @LaconiaCapital, MGV.VC, @Techstars, @NextWaveNYC, and @differentialvc + a few more. Here's the link to RSVP + Apply to Pitch: partiful.com/e/eaZmQ8Q59gAV… Not in pitch mode? Come by and grab a FREE Bacon, Egg, & Cheese, Chopped Cheese, or whatever your Bodega fave is. We'll be giving out $10 vouchers to support our local bodega from 8 AM - 12 PM (or until we run out!). We're also dropping some limited-edition summer swag that you definitely want to get your hands on. S/O to everyone who made this possible! Founder Pro-Tip: Check out each participating firm's thesis and make sure your company aligns when you apply. Investor match notifications will be distributed the morning of June 2 :)

I recently looked at a company building AI for churches. Churches have always been interesting to me because they have a heavy real estate portfolio and huge volunteer network that sits mostly idle six days a week. They have parking lots, event spaces, and member lists. The immediate wedge the team identified was in member retention. For a church, the lifeblood is the congregation. When someone stops showing up or stops donating, it’s often because of a life change, like a kid going to college. AI can help pastors identify those patterns. From there, the opportunity expands into volunteer management, communications, and media. Most small to medium businesses won't solve these problems by building their own AI systems. They need a vertical tool that speaks their specific language. There are roughly 130,000 churches in the US, and on average, they spend about $5,000 a year on software. It’s a massive market that has been largely ignored by modern tech. That's why I love businesses like this.

@nickbilton 🤯 Truly amazing! Congratulations!

We’ve built @flybridge around the New York-Boston corridor for a reason. While a lot of the industry looks West by default, we’ve found that the symbiosis between these two cities creates a unique advantage for early-stage founders that you can't find elsewhere. Boston is a research powerhouse. Between MIT, Harvard, and the broader New England ecosystem, it’s the center of gravity for deep tech, robotics, and complex engineering. It is where some of the hardest technical problems in the world are being solved. We’re seeing that expertise bleed more into sectors every day. New York provides the market scale. It’s the hub for finance, fashion, and real estate, and it’s home to a massive concentration of Fortune 500 companies. If you’re building for the enterprise, you can find almost any major buyer on the planet within a few blocks of our office. We find a lot of value in the connection between the two. It creates a feedback loop for AI and infrastructure founders that’s hard to replicate anywhere else on earth. It's just a short flight or a train ride between the two. I've made many trips back and forth in a single day. If you are a founder based in the New York or Boston area and want to connect over a quick coffee sometime in the next few weeks, I'm going to have some time on my calendar. Drop a line with a little bit about what you're building. We write small checks (~$50k) into early-stage startups that are still just an idea and larger checks ($1-3M) into folks that have a little bit more traction. I'd love to hear from you!

@johnfein Thanks!

Looking for a recommendation for a Paris tour operator who does a great Eiffel Tower tour for my parents and my in-laws, who are going to be going up for the first time ever. In addition any other recommendations for places to eat or unique things to do while we're there with the family?

The fastest way to kill a startup is to stop focusing on what made it work in the first place. My parents once made a wooden step-stool for my son. On the side, they painted a simple reminder: "When you’re doing something, do it well." I think about that every time I hear a founder talk about their new side project. I was recently texting with someone who built an internal AI tool for their team and now want to launch it as a separate side business. I've seen this same story out firsthand. Part of our downfall at WeWork was our premature loss of focus. Even when we were generating a billion dollars in revenue, we lost our discipline. We were investing in wave pool companies, private schools, and enterprise B2B products before we had truly mastered our core business. We mistook scale for stability. AI has made it dangerously easy to build a prototype over a weekend. It feels like progress, but usually, it's just a distraction. If you think your company is ready to manage a second product, it almost certainly isn’t if you’re still in the early stages with your first. Focus is a discipline. Right now, in a world of endless tools and shortcuts, it is the most undervalued asset a founder can have. One thing at a time until the job is done.

@yoheinakajima I am the ultimate optimist and dreamer. I need AI to push back and show me why things won't work. It is my sparring partner to test business models and markets before a founder sets out to change a billion lives.

I have a quick AI question… At Flybridge, we’ve been running an experiment with an internal AI tool that votes on every deal alongside our partnership. It ingests pitch decks, transcripts, and emails, then scores companies based on market size, team quality, and deal dynamics. So far, it hasn't actually sped up our decision-making. If anything, it’s a halfway decent devil's advocate. I think that's because AI is a pattern-matching engine trained on existing data. In venture, we are looking for things that don’t fit the pattern. As a result, we are finding that the AI tends to regress to the mean. If the model thinks a deal is a good investment, it usually means the idea is too obvious. It’s safe and logical, which usually means it's already been done or the market is about to get crowded. I'm sure some other folks have figured out a way to solve for this. If you have any tips on how we can refine our prompt or criteria, let me know. Drop them in the comments or hit me up for a quick chat. … P.S. Would it be helpful to share some of these devil’s advocate findings?

It’s not about one size fits all. I think patterns are helpful in learning and certainly are a part of what we do but the anti-pattern is also important. The opposite of what didn’t work. Or what did work but it a different world and era. I think about all of the SMB plays that didn’t work and then along comes Squire. That sort of thing is more about catching what’s different, not the same.

@shaiunterslak Let’s hang out and we can *not* talk about it!