Jesse Middleton

GP @Flybridge. $1M-$3M checks into founders building AI infra, agents & apps that 10x human potential. Backed @arcee_ai, @micro1_ai, @splice, @getsquire + more.

[Jesse Middleton @srcasm]

It's not easy to convert teams that are AI-enabled to be AI-native. It doesn't feel like a big leap, but at times it can be. It can feel like a drastic difference when you cede control to the underlying code or workflow and step back and allow agents to start to take on the brunt of it.

[Dorothy Jean Chang @dj]

Last week, @sama told Stanford GSB that his chronic disappointment in MBAs is that they "always want to just go do the thing that was cool like five years ago and not do the new thing. And I think this is a great time to go do the new thing.”

Our @flybridge summer associate, Claudia Chen, followed up cheekily: "So go do the new thing, even if AI is the cool thing right now?"

Sam deadpanned: "I don't think this is a good time to start another copy of OpenAI.”

Then he continued with a thoughtful point: “But I think there are many companies that can be built on top of technology that OpenAI has put out into the world that will be much, I hope, bigger and more important than OpenAI."

They covered a lot more ground in this interview - pacing, safety, alignment, Sam’s near-miss with becoming an investment banker, what’s really important in life and much more. Great insight into the mind of one of the most influential innovators of our time.

[Jesse Middleton @srcasm]

@davidfano It seems like an opportunity for a company like Rewind to just watch everything you're doing and figure out where you're handing over keys, usernames, or passwords for auditability for use later on.

It might be interesting.

[Jesse Middleton @srcasm]

@davidfano Damn. :(

[Jesse Middleton @srcasm]

@Clara_Gold Fascinating!

[Jesse Middleton @srcasm]

@jamesoniam This X post was not SOC 2 compliant.

[Jesse Middleton @srcasm]

@arcinternet What about on mobile?

[Jesse Middleton @srcasm]

@davidrgoldberg Nope.

[Jesse Middleton @srcasm]

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.

[Dennis Crowley 🇺🇸 (mostly on Threads, @dens) @dens]

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. https://t.co/HgcgI9DWvy

[Jesse Middleton @srcasm]

@N_Sportelli I am not a bot... boop beep bop bop.

[Jesse Middleton @srcasm]

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: https://t.co/IViilLZeUW

[Jesse Middleton @srcasm]

@katienotopoulos @dj @mims Yeah, it was through Ticketmaster but I think I got in under the wire before they started blocking AND I think my agent handed the browser to me for one step if I remember correctly. It was Weezer and The Shins. It was a good show. :)

[Jesse Middleton @srcasm]

Quick list off the top of my head (my agent told me):

- Wiper blades for the car
- A new MacBook Pro from B&H
- Clothing
- A birthday gift (jewelry) for my wife
- Roses for our anniversary
- Tickets to a show at MSG
- Travel:
- The full trip to Cabo (flights and hotels)
- The full trip to Cancun (flights and hotel) for a wedding + the clothing I needed for the wedding
- SF Tech Week travel
- November SF travel (hello to those of you in SF!)
- A couple of Blades for last minute trips
- And it's built out an itinerary for end of year family trip but I haven't booked it yet

I'm sure I'm missing some but this is a lot. :)

[Jesse Middleton @srcasm]

@dj @katienotopoulos @mims My number is embarrassingly higher than $200. :)

[Jesse Middleton @srcasm]

@ashleevance @blakejharrisNYC Been listening to @AcquiredFM on Larry David last day. There’s so much good Larry content out now. It’s pretty, pretty, pretty good.

[Jesse Middleton @srcasm]

@benspringwater Absolutely loving Sundrop!

[Ellen DaSilva @ellenjdasilva]

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!

[Jesse Middleton @srcasm]

@ajs Same. Side chats are A+ with Muse. As is the feed, surprisingly.

[micro1 @micro1_ai]

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!

[Jesse Middleton @srcasm]

@cyantist Include HEKTAD. He’s amazing and in NYC.