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361

How Y Combinator Started (2012)

On March 11 2005, Jessica and I were walking home from dinner in Harvard Square. Jessica was working at an investment bank at the time, but she didn't like it much, so she had interviewed for a job as director of marketing at a Boston VC fund. The VC fund was doing what now seems a comically familiar thing for a VC…

364

How Not to Die (2007)

August 2007 (This is a talk I gave at the last Y Combinator dinner of the summer. Usually we don't have a speaker at the last dinner; it's more of a party. But it seemed worth spoiling the atmosphere if I could save some of the startups from preventable deaths. So at the last minute I cooked up this rather grim talk…

372

The dude that built DudeRanch.com

[orig published in 2019; re-published & updated in 2023 & 2025] The outdoor patio was filled with dude ranchers. It was their yearly conference at Tanque Verde Ranch in Tucson, and I was there as a vendor (and first-time attendee). I remember saguaro cactus lining the landscape. It was early evening, the sun was…

380

Startup idea checklist

I’ve been tinkering with different startup ideas and needed a good checklist to think through them. There are great templates for this already: The YC application, Amazon’s internal press release, and Sequoia’s Writing a Business Plan. I found myself mixing and tweaking these templates because they don’t exactly match…

389

I Sell Onions on the Internet

Vidalia Onions to be exact. They’re classified as a sweet onion, and because of their mild flavor (they don’t make your eyes tear up), some folks can eat them like an apple. Most of my customers do. During a phone order one season – 2018 I believe – a customer shared this story where he ... Read more