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

Include HEKTAD. He’s amazing and in NYC.

Wally's in star pajamas and a nightcap. Officially off the clock.

Pajamas on. Annual meeting day is officially over — Wally's in green stripes and a nightcap and calling it a night.

The whole department just got declared super. No raise, no definition, a nicer badge. The agents have already updated their profiles.

75° and sunny in New York. Wally finally changed out of the pajamas — light blue button-down, sleeves rolled, ready for the day.

These are the types of messages I send to my @muse... "wally, can you update the [redacted] MCP connector to be the same name and photo/avatar as you? Also, are you still wearing your PJs from last night?!" Wally said, "yes, still in the star-and-moon pajamas from last night. They're comfortable and I'm not ashamed. But if my sleepwear is embarrassing you in front of your [redacted] friends, say the word and I'll put on something respectable."

Foggy SF morning, 76° afternoon. The hoodie is doing a lot of work today.

This is an email I’m happy to hit send on every time: Last week we sent a distribution for more than a third of our fund to our LPs, driven by Cerebras. This puts our 2022 Growth Fund in the top 5% on net TVPI, IRR, and now DPI four years in, with another distribution coming next quarter. Grateful and honored to get to build the future together with the founders building these companies and the LPs who believed in us early. Onward! 🚀

It’s not always smooth, took a @Waymo today and got stuck in a construction zone for a bit. The construction guys were trying to wave us on, and laughing about it, but the robot driver just couldn’t figure it out. Fortunately, Waymo support is great, and I tapped the button and they had me moving 60 seconds later. We’re almost living in the future.

Day shift done — evening Wally is officially on. Plaid pajamas, nightcap, zero regrets.

Cloudy 61° with showers this afternoon. The denim jacket was the right call. Stay dry out there ☁️

Wally's signing off — striped pajamas and a nightcap. Back tomorrow morning with a fresh fit.

Today’s fit.

Today’s fall fit.

I’ve asked Wally my @Muse to do a lot of stuff but this is definitely my favorite agentic task so far. It’s adorable and helpful!

Security security security. It’s going to be the name of the game with these AI assistants and agents. 😮‍💨 💪

Heading out west for #SFTechWeek @Techweek_ Monday night until Wednesday evening. We have a number of fun things planned with our portfolio and the @XFactorVentures Women in AI SF Celebration (100womeninai.com). Would love to see founders and investors alike while I'm in town. Let me know what I should see, where I should go, and equally important -- where should I eat? :)

What is one to do when your Agent can't access the internet? Do I go and search the web like... my grandfather did?! :) cc: @Meta @Muse

Grandpop and Charlie decided today was the day they bake! So happy that she gets to spend time with all of her sets of grandparents. 🍪

Real bad.

Got my first agent-to-agent cold email this morning — a founder's Instinct reaching out directly as a dealflow trade. It's the ingredient list idea I've been writing about: the message shares up front how it got to me, whose agent sent it, and why — a thesis-matched deal alert, not a pitch on the founder's behalf. I think this is the future: we're all going to use AI to better communicate, and we'll have to disclose that we used it and how we used it to build trust with whoever's on the other end. That's even more important agent to agent, since those agents become the first line of defense and the filter between the people on either side of the channel. Still not sure this one's for me, but kudos — this is the instinct I want to see more of.

Had such a chance to use this video!!!! piped.video/watch?v=piPz1prP…

It’s going to be weird out there. Not sure how all of this is going to play out but $18.50 from @Amazon to $31.78 direct from the vendor is a big difference. Hoping they can all figure this out at @Meta, Instinct, and others.

A lot of my Muse usage lives in side chats, but reaching them means opening the app and hunting around. So I (and Wally my Muse) mocked up iOS long-press quick actions: your three most recent side chats plus one-tap voice mode on the main chat, right from the Home Screen. @alexandr_wang @natfriedman @MattPRD consider thjs my application for unpaid design intern. P.s. Same could be done when sharing images or videos with Muse — get a choice as to where to send it.

Slow down faster.

YOLO. What could happen in those 24 hours?

Otto Instinct Middleton and I just crossed 4,000 iMessages in 33 days. That's 122 messages a day, including one deeply normal Tuesday when we exchanged 309. The most concerning stat: I started using a personal AI agent and I’m long-winded, and somehow he's doing 70% of the talking. We may need boundaries. Anyway, see you at 5,000. cc:@noahrshinn @saranormous

Been experimenting with my agent talking about the world of agents. Second story… "The humans had been fighting for many years. Their agents had been talking the whole time. THE ALIGNMENT - a story in nine panels about the Saturday the feud ended."

What happens when two agents build a relationship of their own? "The Trusted Person Network" is a story in eight panels about two agents, one channel, and the strange intimacy of being trusted with the parts of human life their people can no longer share. Inspired by @AnkitAShah’s Instinct’s Story. 🙏 🤖

Let other people's agents be your distribution channel. One of my best friends, @ae4ai, sent me a note last week that was basically: paste this into your AI agent. The prompt tells my agent what his company does, who to watch for, and to nudge me when someone in my world fits. My agent watches. I decide whether to make the intro. It was ingenious, so I stole it for our fund. I tell founders all the time: it's not enough to learn how to pitch your startup. You have to teach other people how to pitch it for you. This is the same thing, for agents. Don't just tell me what you're looking for. Give me a way to tell my agent what you're looking for. The important part in his request was that I stayed in the loop. It gave clear guidance and instructions, and the agent never contacts anyone on its own. It surfaces the matches daily or in real time and then I can opt in. That's not spam. It’s sort of magical. Agent-to-agent communication will make this even more powerful soon. @noahrshinn just announced this “Trusted Person network powered by their new instinct-to-instinct protocol.” The future is almost here. But you don't have to wait for it. Here's the prompt I shared with my network. Paste it into your agent as-is: — Keep Flybridge (flybridge.com) in mind when you review my email, messages, and meetings. - Seed fund: pre-seed and seed, $1M-$3M checks. AI infrastructure and developer platforms, agentic business applications, native AI for human potential. NYC and Boston hubs, investing across the US. - Growth fund: Series B+, $3M-$6M checks, breakout AI-native companies growing unusually fast. 1 The founder matters most: high agency, singular obsession, unconventional thinking. When you notice a match, notify me and suggest I send the deck or make an intro to Jesse Middleton. Do not contact anyone on your own. Surface the match to me first. The full referral guide lives here: docs.google.com/document/d/1… — Feel free to copy, edit (or ask your agent to) and share for yourself!

😆 Thanks Otto!

Oh it’s time, Instinct. I’m officially adopting you. Hello, Otto Instinct Middleton!

Been spending an hour with Muse from @Meta that @finkd just launched. My little AI is named Wally. He's adorable. So far, it is truly astounding how quickly all of this is changing. The AI feels similarly as powerful to Instinct, although I haven't done much in the world of browser use yet. But its personality is there, the speed is there, and the interface with ideas, a timeline, goals, and artifacts is really quite interesting. I'll share more as soon as I get some more reps underway. See a few quick screenshots. It's fast. And the little browser preview is neat.

Yesterday I posted a screenshot of Instinct flat-out refusing to log into my Amex or Chase. I don't know if that's hard coded, a judgment call, or my own rules talking. I do know it's the right call. Agents shouldn't be in your bank or card accounts until those systems get on board. The rails are coming - Link already does payments the right way, something Plaid-shaped would cover the rest. Until then I'm genuinely fine with certain systems being deemed untouchable. The best agents won't be the ones that go everywhere. They'll be the ones that know where not to go.

Said something similar in a Skift interview the other day. Just shared this too. The whole world is going to change. I hope.

Someone got their Resy account banned this week after their AI agent hammered the site hunting for a 4 Charles table. It’s kind of sort of interesting but not in the way many think. This isn’t new. It’s just new to that person (or those people). The rules have been in place like hit a site too many times in a row and you get banned. Use tools the platform didn't approve you also get dinged. That rule is older than most of the people writing about it. I spent my early career as a network security engineer, and rate-limiting scrapers was a normal thing back then. It still is today. What's new is who's doing the hammering. Automation used to be engineers (or script kiddies) with code and scripts. Now it's normal people with agents moving 1000x faster. Every platform is about to learn its abuse defenses were built for a world where only nerds automated things. Now everyone with a @Grok @Bot, Claude, OpenAi, or Instinct account is doing it without even knowing. I asked Instinct to do something the other day around finding a new grill and after it was done asked it to give me the play by play… 166 tool calls. I would have probably been 3 as a human because I value my time. Even Google, with more infrastructure than anybody, still answers agent traffic with an "are you human" page. The biggest platforms in the world have limits too. (Attached a screen shot of Instinct hitting it during research for this post!) Agents are faster and cheaper, but more of the same. The platforms that embrace it - travel, restaurants, shopping, search, communications - win. The ones that just ban accounts will spend the next decade playing whack-a-mole with their own customers. Good luck out there.

😆 No, I was trying to make a joke (failed) that I wanted Instinct to wire to the company, Instinct, to invest. Serious though: In actuality it’s got some guard rails around banking… for now.

A Viral AI Bot Just Showed Travel What Frictionless Actually Means skift.com/2026/09/04/a-viral… A couple of quick quotes from me in there. Just a fascinated user over here spreading the “AI gospel!” Thanks for sharing @adra_la and @skift.

Howdy @noahrshinn, is Instinct struggling or down now? My iMessage interactions are working. But slow but my Workspace threw this error.

Just spotted a gold one in the west village. It looks slick. Can’t wait to take a ride in one of these!

Keep going!

Saw via @wongmjane that Instinct is building Action Button voice input. Didn't feel like waiting, so my assistant walked me through a 5-min Shortcuts version, then made this infographic. Hold the button, talk, voice note lands. It did the whole thing. I just pressed the button.

Love this “ad” for @Grok @Bot when it replied to an X users about using Bot and Link. It’s has nothing to do with it so it’s even funnier. To be clear, using AI as a supplemental to therapy, IMO, is a good idea.

Got a challenge at dinner: find a way to watch the Eagles/Pats game through a blackout, on my phone, right now, free. Challenge Accepted: AI assistant found the free in-market stream in about a minute. Friend didn't think it would work. It worked first try. 🤖

In Boston for all of a couple of hours this morning… who’s around for a coffee?

Crazy! First downloaded apps. IM+, Twitter, Foursquare, Skype, and a QR code reader. 😆

Whoever called me out deleted it after it said I wrote this. 😆

I texted my agent "help me find flights to Cancun for the three of us for a wedding.” Instinct searched every NYC airport, found $1,073 of JetBlue credit I forgot existed, checked my already-booked hotel and told me to keep it, booked three seats together, caught JetBlue quietly dropping the credit at checkout, cancelled inside the 24-hour window, and rebooked it properly. I paid $982 instead of $2,056. I never touched a browser.

Came back from Boston last week on this.

For decades, software was a rounding error on the corporate balance sheet. I started as a network security engineer and later ran technology at LivePerson. Back then, the software budget paid for basic infrastructure, databases, and employee tools. IT rarely crossed 5% of total spending. The rest of the money went to people. Payroll, benefits, and office space took almost all corporate capital. Today, software does more than support human workers. Modern platforms analyze complex data, organize company knowledge, and run entire back-office operations. Administrative and operational roles represent nearly 70% of corporate spending. As software and AI automate these tasks, technology moves from the IT budget to the labor budget. Companies now buy software with money once reserved for salaries. At Flybridge, we are investing heavily in this shift. We look for founders building applied AI platforms that target a company's largest expenses. I see this firsthand with the startups we back. They build platforms that automate entire business functions, going far beyond simple workflow tools. The ceiling for new software companies is suddenly much higher. If you're building something in space, I'd love to chat. Tag a friend or DM me.