Jesse Middleton (@srcasm) 's Twitter Profile
Jesse Middleton

@srcasm

General Partner at Flybridge. Father to an awesome eight year old and a newborn baby girl! 💍 @thecatmiddleton.

ID: 4188111

linkhttps://flybridge.com/ calendar_today11-04-2007 14:36:59

45,45K Tweet

12,12K Followers

3,3K Following

Max Crowley (@maxjcrowley) 's Twitter Profile Photo

Would you split a paycheck for something you believed in? Jesse Middleton Jesse Middleton & his friend SPLIT one paycheck to go all-in on WeWork. No safety net. No fancy titles. Just belief in the vision — and the willingness to burn the boats. Full episode on our bio.

Jesse Middleton (@srcasm) 's Twitter Profile Photo

My wife, Cat, and I have an unspoken rule at home: When we walk through the door, work stays on the other side. Both of us spend the day deep in venture conversations, so it would be easy to keep that thread going over dinner. And yes, late-night calls or a founder crisis still

Jesse Middleton (@srcasm) 's Twitter Profile Photo

Too many founders pitch “AI” like it’s the product. The winning teams treat it like plumbing. Take Covenant (legal ops) and Noetica (deal intel). Both wrap generative models in workflows that CFOs already budget for. That’s because no users want to just “try AI.” They want to

Jesse Middleton (@srcasm) 's Twitter Profile Photo

For a long time I put founders in two buckets: “the tortoise” and “the hare.” But the truth is, the best ones survive market swings by switching between those modes at will. Two real life examples..... "The Hare" - Day 1 was a bare-bones Chrome extension. 12 weeks later the Git

Jesse Middleton (@srcasm) 's Twitter Profile Photo

We need clearer windows into how AI agents work (here's my solution): Last month, a customer-success bot send the same email to the same person, seven times! The bug sat three agents deep, so tracing it took all afternoon. This scenario reminds me of the “self-driving car runs

Jesse Middleton (@srcasm) 's Twitter Profile Photo

NY Tech Week has officially outgrown itself, but that’s exactly the problem we want to have. It was impossible to be everywhere at once this year. The event has gotten so big that even people who know everyone still had to pick and choose. My dad friends and I were texting all

Jesse Middleton (@srcasm) 's Twitter Profile Photo

I have a new litmus test for investments. If I'm not willing to get on a plane and miss time with my kids to meet you, we might not be the right fit (might sound a little harsh, but it’s a pretty good barometer). Last week, I booked a flight to Berlin within the 24-hour

Jesse Middleton (@srcasm) 's Twitter Profile Photo

About to post a role that I’m hiring for at Flybridge in NYC. Where would you share it other than LinkedIn, X, and my own person newsletter? What are the best spots to share to find the best people?

Jesse Middleton (@srcasm) 's Twitter Profile Photo

If you haven't yet, and you're interested in venture, you should take a look at John Gannon's VC Salary Survey -> johngannonblog.com/venture-capita… It's important to be educated.

Alex Konrad (@alexrkonrad) 's Twitter Profile Photo

Exclusive: AI research labs are in a NBA-style free agency frenzy. Upstarts Media obtained OpenAI's comp tiers for research staff, and its pitch for top talent to turn down offers from rival teams like Meta. upstartsmedia.com/p/meta-openai-…