Parade. Thursday. Manhattan.

Let's gooooooo! Congrats everyone!

We asked Claude to fix one file. It read 47, including the SSH keys. Spotlight reads your Claude Code Codex sessions and shows you what actually happened: what to fix, what's burning tokens, what's worth reusing. Free.

AI Question: If you wanted to brainstorm or be creative with a model, which one would you use? What prompts would you leverage? Are there tools you can imagine having an impact on this? Most of the time the current generation of LLMs regress to the mean, they’re built to not hallucinate and that’s usually good. But the way that humans test new theories and come up with new ideas (think: geniuses or the most brilliant musicians) is by iterating, collaborating, trying out new things, even crazy ideas, and then testing them out. The current models don’t feel capable of this. It’s at least not their strongest suit.

We don't hype this up on X really because it's only live in PA but ladies & gentlemen... The Sunflower Clinic of Addiction Medicine is officially shipping Rx And "unlike" our competitors, Sunflower IS designed for the treatment of AUD, not simply "drinking less" 🌻

AI has terrible memory Introducing Micro, an agent that remembers more than Claude, Codex & OpenClaw Leave a comment (eg "memory") & I'll send 30 days for free to try it

New York is the best place on earth to build. Over the past 15 years of investing in and backing the New York tech ecosystem, I’ve watched this community evolve from an underdog into an absolute powerhouse. Silicon Valley will always be an incredible sandbox for core technology infrastructure. However, if your goal is to build a company that deeply integrates with, scales within, and transforms the global economy, NYC has become the ultimate launchpad. Here’s why: 1. Elite Talent Pool The historic playbook of elite engineering and business graduates automatically packing a bag for the West Coast has shifted. New York now commands one of the dense and diverse talent pipelines in the world. • According to recent ecosystem talent studies, New York captures 10.1% of the entire U.S. college graduating class. For context, the next closest market is Los Angeles at 4.9%. • The region is anchored by world-class institutions like Columbia, NYU, Cornell Tech, and Princeton, generating a massive annual surplus of technical degrees. • NYC offers an unmatched concentration of seasoned operators from the Fortune 500. Founders can access developers who deeply understand enterprise procurement, global compliance, and commercial scaling. 2. Vertical Dominance Building software for other software companies is a viable model, but building for massive, real-world legacy industries is where the greatest value is created. New York naturally dominates these sectors because the buyers, experts, and operators live here. • Fintech: According to data from Carta, NYC startups secured 48.5% of all fintech venture dollars raised in the United States, nearly doubling the Bay Area’s 25.9%. • Healthcare & BioTech: Driven by nine major academic medical centers and extensive public-private investments, NYC is the nation’s #1 market for healthtech funding. • PropTech & Retail/Commerce: As the undisputed global capital of both real estate and retail, NYC serves as the primary testing ground for commerce, luxury tech, and property management. • Media & AdTech: The city remains the epicenter of global media, giving local B2B SaaS and marketing tech platforms immediate, direct access to major enterprise enterprise accounts. 3. Capital Resilience and Ecosystem Value The myth that massive, sophisticated early-stage checks are exclusive to the West Coast has been thoroughly debunked by now. • According to the Startup Genome Global Startup Ecosystem Report, NYC’s ecosystem value has now surpassed $620 billion. • Even during broader macroeconomic market corrections, PitchBook and NVCA data shows that median seed and Series A round sizes in New York have remained remarkably resilient, occasionally outpacing the Bay Area in deal velocity stability. • Tech sector employment in NYC has grown by 160% over the last 15 years, outperforming the national tech sector growth rate by nearly 3x. 4. Structural Diversity Building a global product for a diverse world requires an environment that reflects that world. Groupthink is a silent killer of early-stage startups. NYC’s greatest superpower is its built-in cognitive diversity. • Tech ecosystem demographic data highlights that Black and Hispanic workers make up 24.3% of NYC’s tech workforce, compared to roughly 8.2% in the San Francisco Bay Area and 10.4% in Boston. • According to regional ecosystem tracking, 17% of all Black and Latino founders in the U.S. who have successfully raised $1M are based right here in New York. Next Wave NYC We built our pre-seed venture fund, wholly backed by Flybridge Capital, to be a reflection of this exact ecosystem. Our fund is run entirely by founders and operators who have spent the last decade helping scale the NYC startup scene. Our extended investment team includes leaders and alumni from OpenAI, Google, Snowflake, Foursquare, Bowery Farming, Casper, Chief, Flatiron School, Major League Hacking, Squire, WeWork, and The Wing. We are laser-focused on being the very first commitment and the loudest operational supporter for builders tackling: • Native AI applications • Agentic AI for the enterprise • Developer platforms for AI builders If you are building the future here in New York, we would love to learn more about what you're working on. Our inboxes are always open. Let's build. 🗽 — Jesse

Tonight, we’re announcing the 2026 100 Women in AI! My partners, Cheraé and Chip, spent weeks sorting through nearly 1,000 nominations to narrow the field down to 105 incredible honorees. These women spent the past year hosting dinners, organizing demo days, and building the backbone of the AI scene. We’re celebrating them tonight. If you’re around for Tech Week, come find us. Check out the full list here: 100womeninai.com/

Super fun day today! @Flybridge completely took over a local bodega, handing out free BECs while founders pitched us their startups. We had a dozen VCs and a couple hundred entrepreneurs pack the space. We even got to pay it forward by serving free food to the neighborhood regulars. Tonight, I’m heading over to the Pitch Roast show. Text me if you want to snag some last-minute tickets! Or just DM me :)

Alright @flybridge and @AWSstartups win the title for ‘most NYC’ event of the week. Bodega takeover was 10/10 @sasyrae @srcasm

In 2024, the conversation was all about models. In 2025, it shifted to agents. This year, it feels like it’s finally about the people driving the technology forward. That’s why Flybridge is hosting one of our favorite events of NY Tech Week, The 100 Women in AI Celebration. • Date: Thursday, June 4th • Time: 6:00pm - 9:00pm • Location: New York, NY (Get on the list for full location details) While the room is mostly reserved for the honorees, we saved a handful of spots for the broader tech community. If you’re around for Tech Week and want to join us, drop a comment below and I’ll send over the invite link.

I’ll be at Pitch Roast Live this Wednesday for #NYTechWeek. Instead of sitting safely in the audience, I’m stepping in as one of the investors for the night. I'll be reviewing pitches from 4 brave founders while comedians Dan Toomey, Sienna Hubert-Ross, and Troy Bond roast all of us live on stage. It should be a good time, mostly because I’m fully expecting to get torn apart 😂. Cocktail hour is at 6:00 PM, and the show starts at 7:00 PM. I have a code for a handful of free tickets. If you want to come out and watch, comment below and I’ll send it over.

NY Tech Week is here! I’m organizing a few events with the Flybridge team, but my main goal for the week is actually to keep things low-key. If you’re in town (or live here) and building in the AI space, I’d love to connect. We’re actively investing out of our 7th fund at Flybridge, typically writing $1M to $3M checks for teams building AI infrastructure, agents, and prosumer applications. I'm particularly looking to chat with founders working on: • Invisible Infrastructure: The safe, auditable plumbing that makes autonomous systems reliable enough for enterprise scale. • Outside the Chat Box: Voice-native and next-gen interfaces, like a task manager that can turn a brain-dump into something clean. • Deep Vertical AI: Founders tackling messy, non-linear problems (like healthcare or finance) because they have deep, lived insight into the space. Drop a comment below or slide into my DMs to grab a coffee while you're in town. Let's chat 👇

Borrowing this entire post from the one and only @sasyrae… Next week at #NYTechWeek I'm going full Bodega Baddie. @Flybridge, in partnership with @awscloud, is hosting "Pitch VCs, Free BECs," a full Bodega takeover. It's time we add some authentic NY vibes to TECH WEEK by a16z! If you're a founder, you'll have the chance to pitch early-stage investors from Flybridge, @LaconiaCapital, MGV.VC, @Techstars, @NextWaveNYC, and @differentialvc a few more. Here's the link to RSVP Apply to Pitch: partiful.com/e/eaZmQ8Q59gAVM… Not in pitch mode? Come by and grab a FREE Bacon, Egg, & Cheese, Chopped Cheese, or whatever your Bodega fave is. We'll be giving out $10 vouchers to support our local bodega from 8 AM - 12 PM (or until we run out!). We're also dropping some limited-edition summer swag that you definitely want to get your hands on. S/O to everyone who made this possible! Founder Pro-Tip: Check out each participating firm's thesis and make sure your company aligns when you apply. Investor match notifications will be distributed the morning of June 2 :)

I recently looked at a company building AI for churches. Churches have always been interesting to me because they have a heavy real estate portfolio and huge volunteer network that sits mostly idle six days a week. They have parking lots, event spaces, and member lists. The immediate wedge the team identified was in member retention. For a church, the lifeblood is the congregation. When someone stops showing up or stops donating, it’s often because of a life change, like a kid going to college. AI can help pastors identify those patterns. From there, the opportunity expands into volunteer management, communications, and media. Most small to medium businesses won't solve these problems by building their own AI systems. They need a vertical tool that speaks their specific language. There are roughly 130,000 churches in the US, and on average, they spend about $5,000 a year on software. It’s a massive market that has been largely ignored by modern tech. That's why I love businesses like this.

We’ve built @flybridge around the New York-Boston corridor for a reason. While a lot of the industry looks West by default, we’ve found that the symbiosis between these two cities creates a unique advantage for early-stage founders that you can't find elsewhere. Boston is a research powerhouse. Between MIT, Harvard, and the broader New England ecosystem, it’s the center of gravity for deep tech, robotics, and complex engineering. It is where some of the hardest technical problems in the world are being solved. We’re seeing that expertise bleed more into sectors every day. New York provides the market scale. It’s the hub for finance, fashion, and real estate, and it’s home to a massive concentration of Fortune 500 companies. If you’re building for the enterprise, you can find almost any major buyer on the planet within a few blocks of our office. We find a lot of value in the connection between the two. It creates a feedback loop for AI and infrastructure founders that’s hard to replicate anywhere else on earth. It's just a short flight or a train ride between the two. I've made many trips back and forth in a single day. If you are a founder based in the New York or Boston area and want to connect over a quick coffee sometime in the next few weeks, I'm going to have some time on my calendar. Drop a line with a little bit about what you're building. We write small checks (~$50k) into early-stage startups that are still just an idea and larger checks ($1-3M) into folks that have a little bit more traction. I'd love to hear from you!

The fastest way to kill a startup is to stop focusing on what made it work in the first place. My parents once made a wooden step-stool for my son. On the side, they painted a simple reminder: "When you’re doing something, do it well." I think about that every time I hear a founder talk about their new side project. I was recently texting with someone who built an internal AI tool for their team and now want to launch it as a separate side business. I've seen this same story out firsthand. Part of our downfall at WeWork was our premature loss of focus. Even when we were generating a billion dollars in revenue, we lost our discipline. We were investing in wave pool companies, private schools, and enterprise B2B products before we had truly mastered our core business. We mistook scale for stability. AI has made it dangerously easy to build a prototype over a weekend. It feels like progress, but usually, it's just a distraction. If you think your company is ready to manage a second product, it almost certainly isn’t if you’re still in the early stages with your first. Focus is a discipline. Right now, in a world of endless tools and shortcuts, it is the most undervalued asset a founder can have. One thing at a time until the job is done.

Looking for a recommendation for a Paris tour operator who does a great Eiffel Tower tour for my parents and my in-laws, who are going to be going up for the first time ever. In addition any other recommendations for places to eat or unique things to do while we're there with the family?