srcasm's profile picture. General Partner at @Flybridge. Board of @TechNYC. Father to an awesome nine year old and a two year old toddler girl! 💍 @thecatmiddleton.

Jesse Middleton

@srcasm

General Partner at @Flybridge. Board of @TechNYC. Father to an awesome nine year old and a two year old toddler girl! 💍 @thecatmiddleton.

Great resume ≠ great startup fit (there, I said it). I’ve seen plenty of Big Tech folks join tiny startups and do great. I’ve also more than enough that haven’t. The difference is not something you’ll find on a resume. You have to remember that at companies like Amazon or…

srcasm's tweet image. Great resume ≠ great startup fit (there, I said it).

I’ve seen plenty of Big Tech folks join tiny startups and do great. I’ve also more than enough that haven’t. The difference is not something you’ll find on a resume.

You have to remember that at companies like Amazon or…

Jesse Middleton reposted

Dear algo, please show this post only to the weirdest founders building cool shit who could use a $50K investment. Please instruct the users to tell me what they are building.


Recently @JKalifowitz said to me that he can’t ever put his finger on *why* he loves New York so much but he knows it in his bones. Every time he’s away his favorite part of the trip is flying back home to New York City. I feel the same way. There’s nowhere I’d like to be…

BREAKING: New York City still the greatest city in the world.

packyM's tweet image. BREAKING: New York City still the greatest city in the world.


The king of SoLoMo is back! Remember that era — Social Local Mobile? @dens and team are working on a magical app for AirPods called BeeBot. I’ve been playing with and listening to DJ BeeBot for a number of months now and while it’s not perfect yet, it truly hits me with some…

👋 We’ve been working on something new & we’re finally ready to let people play with it. It’s an “app for AirPods” called BeeBot – think of it like a social city guide emceed by an AI-powered radio DJ. I wrote a giant blog post (manifesto!) about it here: dens.medium.com/say-hello-to-d…



I’m so glad @kobyjconrad reached out. I’ve told people before, cold outreach can work. @sunflowersober is certainly solving a problem near and dear to my heart as my father, brother, and I are all living a sober life through addiction and other trials and tribulations. It’s not…

I first pitched our seed lead @srcasm w/ Flybridge exactly a year ago today We were pre product, pre revenue, pre team 😅 Jesse came onboard 8 months later after watching us consistently crush The market is a weighing machine, the best fundraising strategy is execution 🫡

kobyjconrad's tweet image. I first pitched our seed lead @srcasm w/ Flybridge exactly a year ago today 

We were pre product, pre revenue, pre team 😅

Jesse came onboard 8 months later after watching us consistently crush

The market is a weighing machine, the best fundraising strategy is execution 🫡


Jesse Middleton reposted

One of my absolute all time favorite quotes about addiction: "the opposite of addiction is not sobriety, it's human connection" it's a bit counter intuitive, but our AI Sponsor actually drives more human connection because that's a major objective we optimize it for 🧵

kobyjconrad's tweet image. One of my absolute all time favorite quotes about addiction: 

"the opposite of addiction is not sobriety, it's human connection" 

it's a bit counter intuitive, but our AI Sponsor actually drives more human connection because that's a major objective we optimize it for 🧵

Jesse Middleton reposted

Really proud to introduce Caira, the intelligent camera of the future, available now on @Kickstarter ! At @camera_int we're building Caira to allow more people to capture beautiful content without the complex workflow. Every year tens of millions of people upgrade from their…


I love getting to work with these brilliant people all day, every day. Looking forward to these new partners backing the next generations’ most awesome and awe inspiring founders.

NYC’s AI scene is exploding — and we were built to back the city’s most ambitious pre-seed founders. We just leveled up our team with some of the most influential builders & operators in the game:

NextWaveNYC's tweet image. NYC’s AI scene is exploding — and we were built to back the city’s most ambitious pre-seed founders.

We just leveled up our team with some of the most influential builders & operators in the game:


Jesse Middleton reposted

guys last night was so fun. ily. everyone go request your @trygoodword invite or DM me for a code if you're impatient 🤫

alexchungtweets's tweet image. guys last night was so fun. ily. everyone go request your @trygoodword invite or DM me for a code if you're impatient 🤫
alexchungtweets's tweet image. guys last night was so fun. ily. everyone go request your @trygoodword invite or DM me for a code if you're impatient 🤫
alexchungtweets's tweet image. guys last night was so fun. ily. everyone go request your @trygoodword invite or DM me for a code if you're impatient 🤫
alexchungtweets's tweet image. guys last night was so fun. ily. everyone go request your @trygoodword invite or DM me for a code if you're impatient 🤫

The future of networking isn’t AI replacing humans — it’s AI reminding us to be human. That’s why I backed @trygoodword a new networking copilot that helps you stay connected to the people who matter most. It organizes your relationships, surfaces the right people at the right…


Whatever @bdistel is doing -- you should reach out to him if you're solo founder in NYC. It'll be worth it!

Have a really cool opportunity for Solo Founders in NYC to help promote your startup. DM me for details. Friends, can you help spread for awareness? @TechNYC @nihalmehta @erica_wenger @srcasm @micahjay1 @FirstMarkCap @everettcookny @swangentr @TeddySolomon11 @_sonith



I didn’t screen my last two hires for the most important question…do you drink coffee? 😂 Here’s how we onboarded Taiki (my new chief of staff) with nothing more than water: Day one meetings: portfolio founder → big-company CRO → WeWork’s ex-CLO → LP managing billions →…


LFG @sunflowersober @kobyjconrad @shaiunterslak and team! 🚀 🌻

The most popular YC F25 company with 266k monthly website visitors is an AI agent for researchers. The top 10 list: 1. @answerthisio - 266k visitors Founders: @ayushgarg, @MccarrollRyan 2. Mixy - 139k Founders: @joekndy , @JonahSiegle 3. @bolna_dev - 84k Founders:…

chrispisarski's tweet image. The most popular YC F25 company with 266k monthly website visitors is an AI agent for researchers. 

The top 10 list: 

1. @answerthisio - 266k visitors
Founders: @ayushgarg, @MccarrollRyan 

2. Mixy - 139k
Founders: @joekndy , @JonahSiegle 

3. @bolna_dev - 84k
Founders:…


🚜🤖 Huge news! @Agtonomy raises $18M Series B led by DBL Partners to accelerate physical AI adoption in agriculture & beyond. Expanding globally with AI-powered autonomous fleets! 🌎✨ agtechnavigator.com/Article/2025/1…


Jesse Middleton reposted

Today, I'm taking a big step forward by joining @sunflowersober as Director of City Partnerships. AI 🤝 Sobriety, together! 🧵 @kobyjconrad @garrytan #recovery

Twolfrecovery's tweet image. Today, I'm taking a big step forward by joining @sunflowersober as Director of City Partnerships.
AI 🤝 Sobriety, together! 🧵
@kobyjconrad @garrytan #recovery
Twolfrecovery's tweet image. Today, I'm taking a big step forward by joining @sunflowersober as Director of City Partnerships.
AI 🤝 Sobriety, together! 🧵
@kobyjconrad @garrytan #recovery

Traditional deals bury knowledge in PDFs. The insights vanish the minute the ink dries. Covenant is a hybrid of law firm + software where AI is the leverage. LPs can ask plain-English questions of their own verified legal history and get instant, structured answers, plus charts…


🔥 The new AI wave isn’t a crash—it’s a wildfire. It’s going to burn inefficient models, clear the old guard, and leave a stronger infrastructure behind. If you’re building AI-infra, now’s the time. The winners aren’t just apps—they’re the foundation. #AI #startup Worth reading:…

I was saying exactly the same thing - though far less eloquently - on a panel last night. It’s not a bubble. There will be a wild fire.



When AI works, it works magically. @Superhuman absolutely crushed this request. See you soon, Boston.

srcasm's tweet image. When AI works, it works magically. @Superhuman absolutely crushed this request. See you soon, Boston.

I don’t ignore cold emails. Breaking through the noise is a skill you’ll need for customers, hires, and press. A crisp cold email can be a leading indicator of execution. Warm intros help too. They de-risk the “who.” They surface references fast. That’s valuable. Then there’s…


Venture is a relationship business disguised as finance. Dogpatch Labs, years ago. Tony’s Chartbeat office was next to mine. We spent a lot of time at the bars all around the neighborhood. Cat (now my wife) was there too, head of people at Chartbeat. Tony and I hung out. Cat and…


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