I watched someone I love almost die because there was nowhere for them to go between a weekly therapy appointment and a locked hospital unit. That gap shouldn't exist.
I was 22 when I started this. People told me I was too young to build a healthcare company. But the kids we treat are 15, 16, 17. They couldn't wait for me to get older.
I was CFO of Facebook and Genentech. I could have done a lot of things. But mental health is the biggest solvable problem in healthcare, and nobody was solving it well.
I was 24 when I started this company. People told me I was too young to sell to Fortune 500 HR departments. Turns out HR departments don't care how old you are if your outcomes data is better than everyone else's.
Dentists were still mailing physical molds through UPS in 2020. That's not an industry ripe for disruption — that's an industry begging for it.
Our first order was a book called "Leaving Microsoft to Change the World." We were leaving Amazon to change India. The irony wasn't lost on us.
We hit our first-year sales target in three weeks. We had a 20,000-person waitlist. Turns out people really hated paying $300 for something that costs $5 to make.
I was a CPA sitting in a cubicle thinking, this can't be it. I quit to teach yoga, started designing shorts in my apartment, and ten years later SoftBank valued the company at $4 billion. Life is weird.
Our first ad got 3 million views on Facebook before we had a single can of water to sell. That told us everything we needed to know. The brand was the product.
I spent my whole career in advertising watching brands spend millions to be 5% funnier than their competitor. I thought, what if we just made the funniest brand in the world and put water in it?
I read the back of a baby food pouch and couldn't pronounce half the ingredients. Then I looked at the expiration date — two years out. That's when I knew we could do better.
We started OpenSea in 2017 and nobody cared about NFTs for three years. Then one day in 2021, everyone cared at the same time. Being early is indistinguishable from being wrong — until suddenly it isn't.
CryptoKitties crashed the Ethereum network in 2017. That was simultaneously our greatest marketing moment and the moment we realized we needed to build our own blockchain.
I got food poisoning and wanted to find a good doctor online. There was literally nothing useful. That frustration became a company worth billions. Food poisoning is underrated as a startup origin story.
The wholesale industry was a $2 trillion market still running on handshakes, trade shows, and paper invoices. We just put it online. Sometimes the simplest ideas are the biggest.
We were four Square employees who saw small businesses struggle every day. The retailers had no good way to find products. The brands had no good way to find retailers. We just connected the dots.
I was 17, traveling across India, and every budget hotel was a gamble. Dirty sheets, broken AC, cockroaches. I thought, what if every cheap hotel room was actually clean and predictable? That question became OYO.
I made Google Earth. Then Google Maps. Then Pokemon Go. My career has been about getting people to explore the real world through technology. That thread has never changed.
I started ThredUp because my closet was full of stuff I never wore. Turns out 73 billion garments end up in landfills every year. That felt like a problem worth solving.
I failed eight startups before Toss. Each one taught me what not to build. Toss was the first time I built something people actually needed every day.
I built the prototype in a weekend. The idea was simple — what if video had a character limit like Twitter had for text?
I built CrowdFlower, sold it, and then spent two years doing ML research. The tooling was so bad I kept building internal tools just to get work done. That became Weights & Biases.
I started Whoop as a senior at Harvard because I was overtraining and had no way to measure it. My body was breaking down and no device on the market could tell me why.
I helped start OpenAI as a nonprofit to keep AI safe. Then it became a for-profit chasing Microsoft money. So I had to start xAI to do what OpenAI was supposed to do.
We started at Y Combinator as two guys who did not know anything about payments. We just knew that every business in Southeast Asia was struggling to get paid online.
I was a day trader for 10 years before starting Zerodha. I lost money, I made money, I understood exactly what retail traders needed because I was one of them.
I went to a street market in Bangkok and realized every small vendor there had amazing products but no way to sell them online. That was the spark for Zilingo.
I started Zirtual because I needed a virtual assistant and every service I tried was terrible. Bad communication, missed deadlines, zero accountability. So I built my own.
I started with $10,000 and built affordable housing that nobody else wanted to build. Now I build neighborhoods. The principle is the same — find what other people will not do and do it better.
I started Starwood Capital with $20 million during the savings-and-loan crisis. Everyone was running away from real estate. I was running toward it with a shopping cart.
I bought my first duplex for $40,000 at 21 years old. I had no idea what I was doing. That duplex taught me more about money than any college class ever could.
We started as a plagiarism detection tool for universities. Turns out helping people write better was a much bigger business than catching people who write badly.
I emptied my entire 401(k) to fund Calendly. Every penny of my retirement savings. My financial advisor thought I had lost my mind. That was the best investment I ever made.
We have never had an office. Not because of COVID — we were remote from day one in 2011 because we were in Missouri and could not afford San Francisco rent. Turns out that was a competitive advantage, not a limitation.
We met at a Startup Weekend in Columbia, Missouri. Three guys who could not afford to move to Silicon Valley built one of the most valuable SaaS companies in the world. Location does not matter. The product matters.
At my previous job I had to open 15 different tools to figure out why the site was down at 3 AM. I thought — this is insane. What if all of this was in one place? That became Datadog.
I built Grafana as a side project because the existing dashboarding tools were ugly and inflexible. I open-sourced it because I thought maybe 50 people would care. Millions of people cared.
I built Sentry at Dropbox because I was tired of finding out about bugs from angry customer support tickets. By the time a user complains, 1,000 other users already hit the same error and left silently.
We started in Perm, Russia. Not Moscow. Not St. Petersburg. Perm — a city in the Ural Mountains that most investors have never heard of. Location did not matter. The product mattered.
We pivoted from user testing to video messaging. The pivot felt terrifying at the time. It turned out to be a $975 million decision.
At our launch event, I let the audience build an app that made phone calls during the demo. A real phone rang in the room. A developer in the audience answered it. That was the moment people understood what Twilio was.
Modern software is 80% open-source code. Nobody was checking whether that code had vulnerabilities. That is why I started Snyk.
I was detecting fake ad clicks at Twitter. Then I realized the same AI could detect fake emails. Business email compromise costs $50 billion a year. The math was obvious.
We sold Blue Coat for $4.65 billion. Then I looked at the mid-market and realized 90% of companies had zero security operations. That was the opportunity.
We got sick and needed a doctor. We could not find a trustworthy recommendation. That frustration was the original idea.
We arrived in Los Angeles with no money, no return ticket, and an agreement that if the show flopped we would disband. We had nothing to lose — and that is exactly the right state of mind for doing something that has never been done before.