$36M Bootstrapped, Rejected by YC | Rebecca Shostak, S3E14
Rebecca Shostak grew up in Silicon Valley, where her friends’ dads landed on the cover of Forbes and her own father had an IPO. When she was 14, a magazine asked her what she wanted to do when she grew up and she said she wanted her own tech company. Twenty years later she has one. Flodesk is at over $36 million in ARR, bootstrapped, after being rejected by YC. In this episode, Rebecca and I get into what it does to you when a definition of success is painted for you before you’re old enough to drive. We talk about the advice her father gave her instead of teaching her to parallel park, why a profitable business doing $500K a year wasn’t enough, and the years she spent waiting for somebody else to build the idea sitting in her notebook before she decided to do it herself. She walks through what happened when one email from a friend turned into 50 trials in an hour and then hundreds a day, with no support team and a product full of bugs. We get into what she had to learn on the fly when a designer who liked working alone suddenly became responsible for a hundred people, how anxiety she’s carried her whole life showed up at work, and what finally helped. At the end, I asked her what it feels like now that she’s “made it”. Tune in to find out her answer. If you’ve ever wondered what it’s like for a founder to grow up in Silicon Valley, this one’s for you. _______ (01:13) Growing up in Silicon Valley (04:00) On a magazine cover at 14 (07:09) Her dad's one warning (09:49) Why $500K wasn't enough (13:25) The barrier that felt insurmountable (17:37) Pooling their own money (19:58) Why Y Combinator said no (25:41) One email, 50 trials (27:16) The footer that went viral (29:20) 500 support tickets a day (29:54) Never chasing profitability (32:07) "She's a little crazy" (33:42) The moment in the shower (35:49) The hardest part right now (41:29) What she had to learn (42:15) Anxiety and leading 100 people (43:35) Calming her nervous system (46:52) The horse barn, her sanctuary (49:14) Does she feel she's made it (52:25) $200 million and the feeling Show notes: Find show notes of each episode on ProfitLed.fm . Connect with our host: Follow Melissa on LinkedIn where she shares stories & lessons from her founder journey weekly. Connect with Melissa at melissakwan.com and subscribe to ' your founder next door ', Melissa's weekly newsletter on what it's like to build a company without an abundance of resources and friends in high places. Follow @themelissakwan on Instagram and YouTube where she shares short videos of business advice and other truth-bomb sound bites. This podcast was brought to you by eWebinar: Find out how you can turn pre-recorded videos into interactive experiences with chat so you can run your demos, onboarding calls, and training sessions on autopilot, 24/7, without being there. Hop into a demo at eWebinar.com , no salesperson required.




