Jesse Middleton
@jessemiddleton.com
@srcasm on Twitter. Parent to a splendid eight year old son and rambunctious one year old daughter. Husband to a brilliant woman. GP at Flybridge and co-founder of Next Wave NYC and WeWork Labs.
I couldn't be more excited to finally share that I'm hiring a Chief of Staff to join me at Flybridge. This person will work side-by-side with me here in New York every day and will get to join board meetings, pitches, LP meetings, and everything in between.
July 3, 2025 at 3:50 PM
I couldn't be more excited to finally share that I'm hiring a Chief of Staff to join me at Flybridge. This person will work side-by-side with me here in New York every day and will get to join board meetings, pitches, LP meetings, and everything in between.
Today marks 3 years sober and my 9-year anniversary with Flybridge.
For years, I thought drinking was essential to my job. Happy hours...client dinners. I believed that's how business relationships were built. But those moments came with hidden costs I didn't anticipate.
For years, I thought drinking was essential to my job. Happy hours...client dinners. I believed that's how business relationships were built. But those moments came with hidden costs I didn't anticipate.
June 13, 2025 at 2:54 PM
Today marks 3 years sober and my 9-year anniversary with Flybridge.
For years, I thought drinking was essential to my job. Happy hours...client dinners. I believed that's how business relationships were built. But those moments came with hidden costs I didn't anticipate.
For years, I thought drinking was essential to my job. Happy hours...client dinners. I believed that's how business relationships were built. But those moments came with hidden costs I didn't anticipate.
A single endowment can burn six figures a year on lawyers just to confirm that a private-equity subscription agreement matches the side letters it already negotiated.
May 7, 2025 at 2:29 PM
A single endowment can burn six figures a year on lawyers just to confirm that a private-equity subscription agreement matches the side letters it already negotiated.
Love how accessible Uber is but riding in a Waymo is like seeing into and riding in the future. It’s as close as we have made it to teleportation yet. And it’s basically the same price as a human driving you erratically through the city.
May 5, 2025 at 10:48 PM
Love how accessible Uber is but riding in a Waymo is like seeing into and riding in the future. It’s as close as we have made it to teleportation yet. And it’s basically the same price as a human driving you erratically through the city.
I don’t know where I got this from but every night I put my kids to sleep I say, “You are safe. You are loved. You are mine. And I am yours forever and always.”
May 4, 2025 at 6:19 PM
I don’t know where I got this from but every night I put my kids to sleep I say, “You are safe. You are loved. You are mine. And I am yours forever and always.”
I’m off to Amsterdam this evening to meet LPs, GPs, and some brilliant European founders. Who should I meet while I’m in town? Tag one person who’s at the top of your list.
P.S. I’ll be missing these three while I’m gone. 😔
P.S. I’ll be missing these three while I’m gone. 😔
April 2, 2025 at 12:44 AM
I’m off to Amsterdam this evening to meet LPs, GPs, and some brilliant European founders. Who should I meet while I’m in town? Tag one person who’s at the top of your list.
P.S. I’ll be missing these three while I’m gone. 😔
P.S. I’ll be missing these three while I’m gone. 😔
I turn 39 today :)
It’s not a milestone like 40, so I wouldn’t call it a huge deal, but I'll still do something that feels meaningful.
Maybe next year I’ll plan something more elaborate, but right now, life is so packed that I’m happy to just be around the people I care about.
It’s not a milestone like 40, so I wouldn’t call it a huge deal, but I'll still do something that feels meaningful.
Maybe next year I’ll plan something more elaborate, but right now, life is so packed that I’m happy to just be around the people I care about.
March 25, 2025 at 11:04 PM
I turn 39 today :)
It’s not a milestone like 40, so I wouldn’t call it a huge deal, but I'll still do something that feels meaningful.
Maybe next year I’ll plan something more elaborate, but right now, life is so packed that I’m happy to just be around the people I care about.
It’s not a milestone like 40, so I wouldn’t call it a huge deal, but I'll still do something that feels meaningful.
Maybe next year I’ll plan something more elaborate, but right now, life is so packed that I’m happy to just be around the people I care about.
By agreeing to go to Athens on a whim, I was able to break open a conversation that’s been locked behind boardroom doors. For once, we got real about the emotional price tag of building big ideas. Sometimes, the best choices are the ones we don’t overthink.
February 26, 2025 at 6:54 PM
By agreeing to go to Athens on a whim, I was able to break open a conversation that’s been locked behind boardroom doors. For once, we got real about the emotional price tag of building big ideas. Sometimes, the best choices are the ones we don’t overthink.
Put this note out on LinkedIn the other day but offering it up here too. Looking for 1-2 of the most interesting people you know in Miami – founders, investors, or generally brilliant and creative folks – that should be invited, let me know.
January 8, 2025 at 3:44 PM
Put this note out on LinkedIn the other day but offering it up here too. Looking for 1-2 of the most interesting people you know in Miami – founders, investors, or generally brilliant and creative folks – that should be invited, let me know.
For the holidays I’m watching @nbcsnl’s “A Saturday Night Live Christmas” and up pops @AdamSandler singing The Chanukah Song! 🎵 🎶 🕎 👏
December 22, 2024 at 9:26 PM
For the holidays I’m watching @nbcsnl’s “A Saturday Night Live Christmas” and up pops @AdamSandler singing The Chanukah Song! 🎵 🎶 🕎 👏
Who do you think I should meet and talk to? No person is too far out of reach IMO. Let me know.
(Pretty sunset photo has nothing to do with this post. I just took it and liked it.)
(Pretty sunset photo has nothing to do with this post. I just took it and liked it.)
December 2, 2024 at 2:10 PM
Who do you think I should meet and talk to? No person is too far out of reach IMO. Let me know.
(Pretty sunset photo has nothing to do with this post. I just took it and liked it.)
(Pretty sunset photo has nothing to do with this post. I just took it and liked it.)
I’m not saying it’s right for everyone but I’m alright with the help. I used a TI-89 calculator in school, Excel at work, and AI for anything I can in today’s day and age. It’s alright to get help and to use the tools available to you.
AMA.
AMA.
November 30, 2024 at 3:44 PM
I’m not saying it’s right for everyone but I’m alright with the help. I used a TI-89 calculator in school, Excel at work, and AI for anything I can in today’s day and age. It’s alright to get help and to use the tools available to you.
AMA.
AMA.
Headed to Miami for two days tomorrow. Who’s around? A walk, a juice, and a coffee?
(Holden “Jobs” Middleton won’t be joining this trip but… isn’t he awesome?!)
(Holden “Jobs” Middleton won’t be joining this trip but… isn’t he awesome?!)
November 29, 2024 at 6:33 PM
Headed to Miami for two days tomorrow. Who’s around? A walk, a juice, and a coffee?
(Holden “Jobs” Middleton won’t be joining this trip but… isn’t he awesome?!)
(Holden “Jobs” Middleton won’t be joining this trip but… isn’t he awesome?!)
Happy Thanksgiving to you and your family from ours. I hope your bellies are full and your hearts are even fuller. But most importantly I hope you look at your loved ones and they look back at you and you all smile your biggest smiles. It’s contagious! 🦃 😊 🥰
November 29, 2024 at 2:07 PM
Happy Thanksgiving to you and your family from ours. I hope your bellies are full and your hearts are even fuller. But most importantly I hope you look at your loved ones and they look back at you and you all smile your biggest smiles. It’s contagious! 🦃 😊 🥰
I recently invested in one of the most fascinating AI companies I've seen this year.
After moving to the US in 2014, Nyamitse-Calvin Mahinda’s mother passed away due to challenges navigating healthcare. Instead of being defeated, he channeled that loss into innovation.
www.vitalaudio.io
After moving to the US in 2014, Nyamitse-Calvin Mahinda’s mother passed away due to challenges navigating healthcare. Instead of being defeated, he channeled that loss into innovation.
www.vitalaudio.io
November 15, 2024 at 11:43 PM
I recently invested in one of the most fascinating AI companies I've seen this year.
After moving to the US in 2014, Nyamitse-Calvin Mahinda’s mother passed away due to challenges navigating healthcare. Instead of being defeated, he channeled that loss into innovation.
www.vitalaudio.io
After moving to the US in 2014, Nyamitse-Calvin Mahinda’s mother passed away due to challenges navigating healthcare. Instead of being defeated, he channeled that loss into innovation.
www.vitalaudio.io
Had a great time supporting my brother's music performance at Spring Place Wednesday night. Made it even more special having my sister-in-law and mom there with us! 🎵
November 15, 2024 at 1:07 PM
Had a great time supporting my brother's music performance at Spring Place Wednesday night. Made it even more special having my sister-in-law and mom there with us! 🎵
With all the new folks on this platform, it’s probably time I start cross posting and creating fresh content here. But for now here’s my darling daughter!
Hello world!
Hello world!
November 12, 2024 at 2:16 PM
With all the new folks on this platform, it’s probably time I start cross posting and creating fresh content here. But for now here’s my darling daughter!
Hello world!
Hello world!
Bluesky now has over 10 million users, and I was #18,248!
October 11, 2024 at 11:44 AM
Bluesky now has over 10 million users, and I was #18,248!
This kid is just too cool for school. Pre-babymoon trip with the toddler before our actual babymoon has been a success so far. ❤️ @thecatmiddleton.bsky.social and Holden!
June 9, 2023 at 7:20 PM
This kid is just too cool for school. Pre-babymoon trip with the toddler before our actual babymoon has been a success so far. ❤️ @thecatmiddleton.bsky.social and Holden!
Kind of insane outside last night in NYC. Air quality was real low due to 🔥 from Canada. 😳
June 7, 2023 at 11:19 AM
Kind of insane outside last night in NYC. Air quality was real low due to 🔥 from Canada. 😳
Enjoyed an evening with friends and family (no politics) at a wedding in Brooklyn. Happy times are the happiest of times. ❤️ @danmaccarone.bsky.social, Devon, and @thecatmiddleton.bsky.social!
May 14, 2023 at 11:24 AM
Enjoyed an evening with friends and family (no politics) at a wedding in Brooklyn. Happy times are the happiest of times. ❤️ @danmaccarone.bsky.social, Devon, and @thecatmiddleton.bsky.social!
A weekend with the family. Everyone is doing their “work”. 👋🏻 @thecatmiddleton.bsky.social
May 8, 2023 at 12:57 AM
A weekend with the family. Everyone is doing their “work”. 👋🏻 @thecatmiddleton.bsky.social
My favorite espresso cups are “right handed” cups. To be honest, I appreciate a cup with an opinion.
May 4, 2023 at 3:40 PM
My favorite espresso cups are “right handed” cups. To be honest, I appreciate a cup with an opinion.
I had a phenomenal time at this thing called a #Junto last night in NYC. The organizer, Andrew Yeung, has been throwing some outstanding events for the NY tech community and I’m looking forward to attending more.
April 27, 2023 at 5:38 PM
I had a phenomenal time at this thing called a #Junto last night in NYC. The organizer, Andrew Yeung, has been throwing some outstanding events for the NY tech community and I’m looking forward to attending more.