Bob Moore: You Never Really Start From Nothing

Bob Moore has sold two software companies and raised more than $100 million for a third. So how did he get here? Like most entrepreneurs, he got his start when someone gave him a chance. For Bob it was a neighbor who owned Tony Luke’s, the Philly cheesesteak shop, and paid a seventh grader a couple hundred bucks to build its website. That turned into a high school web design business. At Princeton he ran three businesses at once, each with very different business models. None became a huge hit, but they forged him into an entrepreneur. Right after college he joined Insight Partners, where he learned what investors look for in software companies and made friendships that have lasted his whole career.Being an entrepreneur can be humbling, and luck plays a bigger role than most people admit. Bob and his co-founder, Jake Stein, quit their jobs to start RJMetrics on a Friday, and Lehman Brothers collapsed the next day. They kept at it and sold RJMetrics to Magento, a real win. Then Looker, the rival that had beaten them in head-to-head deals, sold to Google for $2.6 billion. As Bob puts it, “your $100 million rounding error was greater than the amount that we sold RJMetrics for.”Bob didn’t stop. Each company fed the next. Raising money got easier, and so did finding early customers: Crossbeam’s first three were companies he had already built or worked with. His story shows how relationship capital and the entrepreneurial spirit compound over time, as long as you have grit, stay humble, and keep going.www.whogotmehere.comTime stamps:00:00 — Introducing Bob Moore01:15 — Dial-up modems, AOL, and a house that valued tinkering02:30 — Tony Luke’s: building the coolest cheesesteak website you’ve ever seen03:45 — Skipping a summer at Wawa: his first web design agency04:52 — Princeton and “financial engineering”06:10 — Insight Partners: 100 cold calls a week, one deal a year07:06 — Ryan Hinkle and Deven Parekh09:05 — His class at Insight, and meeting Jake Stein on day one11:30 — College FOMO and Yes Letter12:08— The Moraculator: poker odds and product-market fit14:36 — A.J. Khubani and the As Seen on TV playbook16:14— The Spill Bullet and a spring break in Chinese factories17:30 — The Sharper Image, and why software beat hardware19:12 — Golden handcuffs: deciding to leave Insight21:42 — Quitting on Friday, Lehman collapses on Saturday23:02 — Spinning Stitch out of the Magento deal24:51 — The “Triple Lindy” and Bob’s weekly call with Jake26:10 — Watching a rival sell for $2.6 billion27:15 — When your biggest rival becomes your first partner28:30 — The origin of Crossbeam: a data standoff between partners32:06 — Solving the cold start problem with your network33:00 — $3.5 million on a PowerPoint deck in a week34:04 — Creating the ecosystem-led growth category35:45 — AI, MCP, and agents that need permission to share38:10 — Closing This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit whogotmehere.substack.com