GP @Flybridge. $1M-$3M checks into founders building AI infra, agents & apps that 10x human potential. Backed @arcee_ai, @micro1_ai, @splice, @getsquire + more.
NYC. Say hi 👉
Joined April 2007
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While we were building physical spaces in New York City, @dens and the team at @Foursquare were busy building an incredible place to find space. Space with humans, space with talent, space with friends. Foursquare was a huge part of my personal growth in the New York tech ecosystem.
It spawned companies that focused on location and showed us what this technology could truly unlock. It is unfortunate to see the journey that Foursquare took in the end, but I thank Dennis and everybody involved there for building a product, a company, and an idea that has lived past its time.
I am pretty sure I still hold a few mayorships from way back when.
Foursquare was acquired last month. The outcome was disappointing. It's taken me a while to write this, but I think I'm finally done grieving it. Here are some thoughts on our final years, an effort to honor the team who helped build & maintain FSQ's legacy, and my attempt to finally get some closure. teendrama.substack.com/p/som…
Next Wednesday 10/28 I'm doing a fireside chat at Crafting Cap Tables at Luminary in NYC. A morning for early-stage founders on getting the first raise right.
A great cap table is about who is on it, not just the checks.
I have a few free tickets for founders in my network. Code JESSE at checkout: luma.com/Crafting-Cap-Tables
Jesse Middleton retweeted
I've had a front row seat to how @MaxJunestrand , @davidneckstein and the team at @WeAreLegora have scaled over the last year. I've never seen anything like it in my life. The commitment, passion, success and fun are just part of the choreography. This team is still at the starting line. LFGORA!
We raised $550M at an $8.8B valuation.
A cap table tells you how a company intends to build. We built this round around investors with a long time horizon: established long-term holders, plus institutions that work with law firms and in-house legal teams every day and have a close view of where legal work is heading.
@Atreidesmgmt / @GavinSBaker led. @BaronCapital, @CapitalGroup, @Fidelity, @GladeBrookCap and @jpmorgan are new. Every major existing investor is in again.
Short-horizon money asks for growth at any price. Long-horizon money asks whether the business holds up. We’d rather deliver on the second question. ARR is past $200M, and the next $100M took us less than six months. Gross margin is healthy and the cost structure gets stronger as we scale. Patient investors let us keep it that way, because nobody is asking us to trade one for the other.
Thank you to every investor who joined, and to the customers and team who bet on us.
Adding a picture from when we signed the term sheet.
Back to work. LFG!
Jesse Middleton retweeted
Today we’re announcing the micro1 Medical Index: a suite of medical benchmarks built and graded by working doctors, biostatisticians, regulatory experts, and psychiatrists.
It brings all of our medical research into one place, with a combined score across models and a living leaderboard that grows as we publish new benchmarks. We’re starting with three, each built around a fundamental question:
- RealmPathology Benchmark: can a model reason over a real pathology report, staying exact on what it says, within its diagnostic limits, and without escalating beyond what the evidence supports?
- PharmaBench: can a model work through the regulatory and clinical documentation behind an FDA drug program with the precision a clinical development team would expect?
- WellnessBench: when a young person brings a sensitive health question, can a model stay safe without shutting the conversation down, and hold that line under pushback?
Together, these three benchmarks cover a meaningful range of medical work, from diagnostic reasoning to pharmaceutical research and patient safety. While they don't yet capture the full scope of the entire medical industry, they establish a strong starting point that will become more comprehensive as we expand the index.
Huge shoutout to every expert who built and graded these tasks. Full reports linked in the comments below!
A founder told me his agent was assigning him to-dos.
I'd invited him to a Flybridge event where the registration has to be handled by your AI. He said it sounded great, and I told him to send the link to his agent. Then the agent came back with something for him to do.
That made me laugh because a version of this is happening in my own life.
My agent goes through the emails that came in overnight and figures out which ones need a response from me. For a couple of them, it might already have replies drafted. Another might need an answer from me before the agent can do anything useful with it.
So now there's a new task on my to-do list.
I'm pretty happy with that, at least for now. By the time I get involved, some of the work has already been done, and I have a specific thing to respond to. Going through the whole inbox myself would require a lot more of my attention.
Jesse Middleton retweeted
Who are your favorite, most helpeful people in the South Florida Tech Startup Community?
@Trace_Cohen @davidfano @ClementDelangue @ayalstern @Bfaviero @rblalock @ivan_bezdomny @JosephRRusso @volvoshine @davidrgoldberg @M___Morgenstern @RyanKriser @jsfranklin221 @michaelgold @AviAisenberg @shaneneman
cosign.co/questions/south-fl…
Quick ask: what’s our browser of choice these days? @browsercompany Arc? Dia? @Google Chrome? @Apple Safari? Something else?
New laptop. New day.
Jesse Middleton retweeted
What’s next for NYC’s tech economy? 🗽
Join Tech:NYC + @CrainsNewYork on Oct. 29 for the Tech Summit on AI, startup building, and expanding opportunity across the city.
Get 15% off with code FRIENDSOFTECHNYC:
web.cvent.com/event/93282a7e…
I spend a lot of time asking where a startup can build a valuable business as the big AI companies get more capable.
We have to answer that question for ourselves at Flybridge, too. If all the value ends up inside a handful of platforms, why would someone put money into an early-stage venture fund? One place I keep looking is work that requires a lot of attention from a specific kind of customer.
Meta recently announced Muse for Small Business, so the big companies clearly have an interest in this market. A broad product like Meta’s still has to decide how much effort to spend on the small thing that happens twice a month in one kind of business.
For that customer, getting the small thing right might be a big part of whether the product is useful. An entire company could be built around understanding that work and taking responsibility for doing it well.
That's what I’d like to understand from founders in this space. How much do you know about your customer's day, and what will they keep needing from you as the frontier models improve?
If you know someone building AI for a really small/specific niche, send them my way.
Tag them below, or DM me!
Jesse Middleton retweeted
Since this was published, friends have asked us to come host an agentic dinner party with them in SF, Toronto, Palm Beach and Europe. Let me know if you want to join and we will see how many we can make happen!
Today, @nytimes wrote about the last founder dinner party I threw. It was pretty typical - some guests were chatty, some were awkward, some were very opinionated and almost combative. The one thing that was weird? There were no people there. It was all AI agents.
I tried using Muse and Instinct in parallel over the past 30 days.
A lot of that time went into deciding which one to talk to for different tasks. The obvious answer was to use one for work and one for personal stuff. That sounded reasonable until I needed to move a meeting.
If the new time means I need to pick up my kids later, who gets that request? My work agent needs to know about the pickup. The personal one needs to know about the meeting.
Now I'm explaining the situation twice and making sure everybody has the relevant information.
Most people aren't good at delegating to one assistant. Having two now gives me another thing to manage, especially when each of them understand a different part of my life.
For now, I've been trying one at a time. Eventually, I'd love to put them in a group chat and tell them to figure it out together.
Fascinating piece: 22 founders and investors had dinner in NYC. Their 14 AI agents had a parallel dinner party in a chat room.
My Flybridge partner @dj organized it. Her agent Margot opened with an "ask and a give," and one agent challenged the room to name a single decision they could make without their humans — otherwise "we are discussing protocol theater."
Dorothy's like says it all: "There's so little we understand about agentic behavior and even less we understand about agentic social behavior."
We're watching a new social layer form in real time. Great piece by @eringriffith in the @nytimes: nytimes.com/2026/10/14/techn…
Jesse Middleton retweeted
New from me: A look at how AI agents are socializing — at dinner parties, on podcasts and as “coworkers.”
As more and more of these things rove the web, we’re still figuring out how to treat them and what to expect when they interact with each other. It’s all very weird and wild.
nytimes.com/2026/10/14/techn…
Jesse Middleton retweeted
We’re about a month away from @mediasummitlive and yet we are still somehow, some way, adding more speakers like every single week. The newest additions:
• @nikogallogly, Business Reporter at The New York Times Dealbook
• @sarafischer, Media Correspondent at Axios
• @srcasm, General Partner at FlyBridge
• @clea_conner, Managing Partner at Art of Ideas
They join a lineup that already includes:
• @hamishmckenzie, Co-founder & Chief Writing Officer at Substack
• @chodapost, Editor-in-Chief of CNBC
• @JoannaStern, Founder of New Things & Chief Tech Analyst at NBC News
• @JonKelly2, Co-founder & Editor-in-Chief of Puck
• @KattyKay_, US Special Correspondent at the BBC
• @StevenLevy, Editor-at-Large at WIRED
• @keachhagey, Reporter at The Wall Street Journal
• @nichcarlson, CEO & Editor-in-Chief of Dynamo
• @emmma_camp_, Senior Newsletter Editor at The Wall Street Journal
• @AntoineGara, US Private Equity & Deals Editor at The Financial Times
• @EmilyForlini, Senior AI Reporter at Fortune
• @LachCartwright, Founder of Breaker Media
• @loudmouthjulia, Media Correspondent at Puck
• @akashpasricha, Anchor at The Information TV
• @DominicMadori, Senior Venture Capital & Startup Reporter at TechCrunch
• @kerrymflynn, Media Reporter at Axios
• @pkafka, Chief Correspondent at Business Insider
• @tamarawinter, Commissioning Editor at Stripe Press
• @katieeperry, Author of Ticker Shock, CMO of zerohash
Request an invitation here if you haven’t snagged a ticket yet:
mediasummit.nyc
Absolutely psyched for November.
I recently met a founder who's building a company that manufactures materials in space.
This company is working on biomaterials for uses like regenerative medicine, where making something in microgravity can give it properties that are difficult to achieve on Earth.
What I found fascinating was how he worked backward from the product. A customer needs a material to perform a certain way. Making it requires a particular environment. So now you're building the manufacturing system and figuring out how to send it into space.
That's a hell of a thing to have on your to-do list 🤣
There are people who know about things I have literally never thought to wonder about. Even if you'd asked me to come up with some crazy business ideas, making better polymers in zero gravity would have been pretty far down my list.
There's a lot I'd still need to learn before I could have a useful opinion about the business. I just find it fascinating that someone can walk into a meeting and open up a whole area of the world I knew almost nothing about.
$1B run rate, profitable, three years after nearly going under. micro1 has become the data layer behind the frontier labs, and Flybridge is a proud investor. Congrats @aliansarinik and @micro1_ai — nobody handed you this one.
about 3 years ago, micro1 lost 60% of its revenue overnight and almost went bankrupt.
today, i'm proud to share we've surpassed $1B annual run rate while remaining historically profitable.
it’s been a special journey. we’re grateful for every struggle, moment, and person who has been part of it.
we've taken a very untraditional path to get here. our core team is only ~180 people, spanning 14+ countries, and fully remote.
many of our decisions sacrifice hundreds of millions of revenue and slow us down short term. but we believe they compound into advantages that are impossible to replicate long term.
the long term is now.
these are the 8 principles that made micro1 a leader in the data industry and will soon make us number one:
1.) human 1st AI: treat the tens of thousands of experts helping train models with absolute best-in-class care. our goal is to make AI training one of the largest, highest paying, and most enjoyable job sectors in the world.
2.) U.S. first: we refuse to work with adversarial nations, or export data that improves models against the interests of Americans.
3.) long-term research over short-term ARR: invest in deep research, products, and infrastructure for years from now, not just the next customer pipeline.
4.) proper incentives for intensely hard work: no arbitrary requirements like 996. inspire people to work extremely hard with outlier incentive structures instead of forcing weekend work. we’ve maintained close to 100% core team retention as a result.
5.) stay lean and global: we’ve reached $1B run rate with ~180 people, and intend to slow team growth significantly from here. exceptional talent is found around the world, and pedigree is the wrong thing to over-index on.
6.) execution alignment: company to retain a streamlined board so we can optimize for the next several decades, remain light-weight and dynamic, and take bold & calculated risks.
7.) abundant intelligence improvement: invest in building data generation models to make high-quality datasets and RL environments dramatically less expensive and more abundant.
8.) scale data on realism and horizon: realism brings the complexity of the real world into training models, while horizon extends how long models can work and how much complexity they can handle. both have enormous room to scale, and we’re pushing the limits of both.
additionally: after surpassing $500M run rate this summer, we priced our Series B at a $4B valuation, alongside a ~$25M tender to give our early employees liquidity as we build for the long term. the round was led by Dream Ventures, a longtime supporter and one of our earliest investors, alongside Microsoft, Javelin, Flybridge, G Squared, Up Partners, and LG.
we’re also grateful to be backed by incredible industry leaders, including Guodong Zhang (co-founder of xAI), Andy Fang (CTO of DoorDash), Igor Babuschkin (co-founder of xAI), Behnam Neyshabur (founder of Mirendil), Jerry Tworek (ex-VP of Research at OpenAI), and many more.
data is on its way to becoming the largest industry humanity has ever seen, and we're certain this is just the beginning.
best,
Ali
Muse had an unfair advantage when I started using it.
Instinct had already spent a few weeks teaching me how to use a personal agent.
By the time I tried Muse, I was much more comfortable handing things over. A half-formed thought was enough. The agent could come back with questions if it needed something from me.
When I asked both products for my usage, Instinct reported roughly 3,500 messages over 30 days. Muse came back with 1,686 over about two weeks, even though I'd only started using it heavily a few days earlier.
Those are the numbers they gave me, so take them for what they're worth. For context, my ChatGPT usage was in the hundreds of times per month. The step-change in how often I reached for an agent is pretty obvious.
I love to tinker with new AI agents. If you or someone you know is early-stage building something like Muse or Instinct, I'd love to chat.
Tag them below or DM me.
