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.
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00:00 — Introducing Bob Moore
01:15 — Dial-up modems, AOL, and a house that valued tinkering
02:30 — Tony Luke’s: building the coolest cheesesteak website you’ve ever seen
03:45 — Skipping a summer at Wawa: his first web design agency
04:52 — Princeton and “financial engineering”
06:10 — Insight Partners: 100 cold calls a week, one deal a year
07:06 — Ryan Hinkle and Deven Parekh
09:05 — His class at Insight, and meeting Jake Stein on day one
11:30 — College FOMO and Yes Letter
12:08— The Moraculator: poker odds and product-market fit
14:36 — A.J. Khubani and the As Seen on TV playbook
16:14— The Spill Bullet and a spring break in Chinese factories
17:30 — The Sharper Image, and why software beat hardware
19:12 — Golden handcuffs: deciding to leave Insight
21:42 — Quitting on Friday, Lehman collapses on Saturday
23:02 — Spinning Stitch out of the Magento deal
24:51 — The “Triple Lindy” and Bob’s weekly call with Jake
26:10 — Watching a rival sell for $2.6 billion
27:15 — When your biggest rival becomes your first partner
28:30 — The origin of Crossbeam: a data standoff between partners
32:06 — Solving the cold start problem with your network
33:00 — $3.5 million on a PowerPoint deck in a week
34:04 — Creating the ecosystem-led growth category
35:45 — AI, MCP, and agents that need permission to share
38:10 — Closing
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