Harper

I was VP of Engineering at Goldman Sachs. The hardest part of leaving it and starting a startup wasn't the money. It was breaking the habits and deprogramming myself. At big companies, you don't just do things. You check with people first. You get everyone to agree. You wait for the right meeting. For 10 years, I did that without thinking about it. Then you're at a startup with no one to align with and nothing to wait for, and none of it works anymore. So I had to unlearn it. A thing that did surprise me was I thought moving fast meant being messy or unorganized, It doesn't. I'm still an organized person. That never changed. I just stopped organizing everything before I start. Now I start, and I build the structure as I go. Both gears at once. And that's what i look for when i hire. Not the perfect resume. Someone who can hold structure and speed at the same time and doesn't wait for permission to start. We're hiring engineers like that right now. I've been heads down for a few years and haven't written much here. Going to start documenting the engineering side of building this. What we're getting right, what breaks, what i'm still figuring out.

My LinkedIn tells you I went to Brown University, worked at Goldman Sachs, The Carlyle Group, and Coatue, left Harvard University, and co-founded Harper. Here is what it does not tell you. I grew up in rural Alabama where working for big companies was not even something people thought about. My mom raised me alone. Two jobs. The math never worked. But she did. The night before ninth grade I knelt in front of an empty refrigerator. No electricity. Went to bed hungry. Woke up to a cold house and a school where I knew nobody. I thrifted a sports coat and wore it like armor. I watched my uncle's trucking fleet get crushed by insurance costs before he ever had a real shot. I sat in a Harvard Business School classroom learning about cranberry factories while the world was changing outside. I failed my first startup. Got rejected again and again. We compress years into outcomes. What we lose are all the moments in between when you almost stopped. The resume looked like it went up and to the right the whole time. It did not. Harper

7 out of 10 small business owners are one bad day away from losing everything. Most of them are paying for business insurance right now. And that policy was written for the business they were running when they signed it. Since then they took a bigger contract. Added a service. Started doing the work that actually brings in the money. The policy stayed where it was. They're covered for the business they used to run. Most owners find that out on the worst day of their life. That's why we built Harper. Business insurance that keeps up with the business you're actually running.

We moved! And we're hiring across 35+ roles to build the company that replaces how commercial insurance works.

I'm hiring a Product Manager to work with me at Harper (YC W25). 90%+ of commercial insurance still runs human-led. We're building the inverse: AI-led, end-to-end. We're not building AI tools for brokers - we are the broker! Not going to copy-paste the JD here. It's solid, go read it. The short version: you'd own a module end-to-end, decide what to build and (more importantly) what not to build, and help figure out what an AI-native company actually looks like. Good fit if you're 1-3 years into product, or an operator/engineer who's been doing PM work without the title. Apply directly through the link, or DM me why you're the right person.

The Headlines: 1. Y Combinator, Forbes 2. 8-Figure Raise 3. $8M ARR 4. AI startup What I see: 1. The team clocking in at 5AM 2. Days that stretch until 9PM 3. 80-hour weeks 4. Phones that never stop ringing 5. A team that genuinely cares about every customer on the other end A team that never stops, never complains, and always shows up with ideas. These milestones are theirs as much as mine. If you are building something big, surround yourself with people who are in it the same way you are. Everything else follows. This one's for my team. Harper (YC W25)

Everything I tried before raising $47 million. 1. Goldman Sachs: Hustled my way in, made associate in 6 months, and dipped out before I could get comfortable. 2. The Carlyle Group: Failed an entry test, got rejected, tried again anyway and got the job. 3. Coatue Management: Spent 3 years at one of the most prestigious hedge funds in the world. 4. Harvard Business School MBA: Saw no connection to the real world. Left within a year. 5. Founded Poolit: Got 10,000 users, raised $6 million. But it imploded. 6. Tried selling software to companies. Nobody wanted it. 7. Saw a gap. Started Harper (YC W25) from a kitchen table with Tushar Nair. 8. Applied to Y Combinator four times, got rejected every time, but got in on the fifth. 9. Started last year at $40,000 in ARR, ended at $5 million. 10. Grew a 50-person team in San Francisco. Outgrew one office. Moving to another. A lot of years. Tons of failures and wins. Just one lesson. Keep going. Keep Swinging it. Harper (YC W25)

We have interviewed 100s of people. After pace, the #2 trait we hire for is Intellectual Curiosity. Our problem set will change. Today, we think we need to do X. Six months from now, it could be something completely different. We have to respond and react. We are building in AI - a space that changes every few months. The pace here does not slow down for anyone and it's not easy. It requires a certain kind of person. Someone who is agile, thinks curiously about problems, and is smart about the way they solve them. You can teach someone a skill. But you cannot teach someone to genuinely want to figure things out. And when we find people like that, we hold on to them. If this sounds like you, we are hiring. Harper (YC W25)

"Barber at Harper" We have a barber on call at the office. Building a company is all consuming. The team puts in long days and the to-do list never gets ends. At some point I realized the last thing someone should have to worry about is finding time to get a haircut. For instance Finn Lancaster one of our Forward Deployed Engineers was on his 40th hour. So we fixed it. Every few weeks the barber pulls up. Sets up in the corner. The team cycles through between calls and coding. One less errand and one less thing in the way. Taking care of the people building with you is not a perk. It is just the right thing to do. We are hiring! Harper (YC W25)