The investor who asked me one question that sunk my whole pitch
Back in 2019 I was running a little delivery app in Austin, nothing fancy, just local restaurants and a two man team. We got a meeting with a seed investor who seemed genuinely interested, and I had this whole deck with growth charts and market size numbers. He sat there for like 20 minutes nodding along, then he asked me, 'What happens when DoorDash drops their fees to zero in your zip code?' I just froze, because I had no real answer, I mumbled something about niche loyalty but we both knew it was BS. He passed on the deal, and honestly the business folded about 4 months later when exactly that scenario played out. That question stuck with me more than any of the success story advice, because it forced me to see my plan had no moat at all. Has anyone else had a single pointed question from an investor or advisor that exposed a fatal flaw you were too close to see?