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Over 40 people signed up to each event! Thank you! I'm honored and feeling grateful. I'm going to organize more – more founder dinners, more AI engineers. Stay tuned

I'm hosting several dinners in the coming weeks! AI PMs: luma.com/gh86on8x Founders at House of Prime Rib: luma.com/i5kv6lej AI Engineers: luma.com/nvr17npf

My friend and I are bringing together a group of incredible founders for House of Prime Rib. 10 of us – good laughs, good food, good conversations. Next dates: 1. Tue, Oct 13 at 7pm 2. Wed, Nov 18 at 7pm Who wants in? DMs open!

Startup pivots are always surprising. Most people don't know that our first idea was Notion/Asana for content creators. It was April 2020, we were all at home consuming online content, and it made sense to help creators organize their talent.

One of my favorite things is when people assume we compete with @UseCorgi. We don't. We're operating in different worlds. We insure some of the largest builders and operators of the physical world - hospitals, highways, data centers, housing and more.

CTOs who ship code.

History doesn't repeat; it rhymes... at least in the tech world, it does... Magic was a text-based service that could do anything for you. Today, we call it "AI" nitter.cf/MrFireDragon/status/57…

There is no better feeling than getting DMs during a team meeting about how hyped the individual is about the vision and the work we're doing. LFG.

Wanna play poker and talk about AI? I've got the event for you. We're hosting a poker + AI engineers tomorrow night: luma.com/ytrcqyrt

Hot take: im slowly but surely moving more and more of my usage from Claude to Codex. 1. Much better desktop app, that actually works! 2. Cowork is much better and more reliable on Codex 3. Better features with coding 4. My MCPs dont random stop working and I'm wondering why

New role alert: *AI Product Manager* We're completely rethinking how underwriting happens at Shepherd with AI agents – and we're best positioned to solve this. We have years of data, a best-in-class modern platform, and an incredible set of hungry/driven/talented engineers. Come work with Angelina, Prajwal, Esmé, Angela and Preston on solving one of the hardest problems in insurance. DM me if you're interested!

I want to create the job board with the most data about startups, investors and trends. Every startup profile has a detailed overview of the company, funding, founders, news and more. See for Shepherd:

I built the website I wish I had when I was looking for a job: jobswithstartups.com Allows you to semantic search to find the perfect job for you. More features coming: - upload resume, find the best matching jobs - customize resume to match a job's reqs - more!

Congrats on the release of Prisma 8, team @prisma! Is there a migration path for those who want to move to 8 without rewriting our entire backend?

That's me right there 👇 You might be wondering how the CTO of an Insurtech ended up at Nasdaq’s Opening Bell Ceremony. Shepherd came in at No. 139 on the 2026 Inc. 5000 this morning and no. 11 in the SF Bay Area on 2,334% revenue growth over three years. Inc. Magazine brought founders on the list here to ring the opening bell, and it is one of the more surreal rooms I have stood in. Everyone here built something amazingly unique that happened to work. And to be welcomed into a room full of artifacts of great companies that are listed on the Nasdaq, including Airbnb (my former employer!), Lime, Tesla, Apple, AMD, Qualcomm and many more.

It's here. Our first *real* NYC office. And it's awesome. I'll be sharing more in the coming weeks about our expansion into NYC, engineering, and the actuarial work we're doing. And we're hiring across the board, including our first engineers in the NYC office. If you like sitting next to the people who use what you make, come move in with us @withshepherd

Oftentimes, the simplest ideas win. Uber: one click, a car shows up. Airbnb: stay in someone's home while they're away. Robinhood: zero commission stock trading. GEICO: skip the agent, go direct. Netflix (v1): DVDs by mail, no late fees. Zoom: click a link, you're in the meeting. Shopify: an online storefront, without a developer. Dropbox: a folder that's on every device. And for Shepherd: adopt technology on your job sites, pay less premium. It's a simple promise to customers that helps these ideas win.

Vercel is what Heroku should have become. Dont sell to Salesforce.

Startups are funny. We've generated more revenue in the first 6 weeks of Q2 than in our first year in business. 10x more. The compounding effects of startups are magical.