Scaling Founders

Most founders expect the pressure to ease once the product starts working. For Tom Brunskill, CEO and founder of Forage (YC W19), it did the opposite: the more the product and company grew, the more people needed something from him, and the more he organized himself around giving it to them. He felt lonelier after his Series A than he had working out of his kitchen in Palo Alto during Forage's early days.Amy coached Tom for almost 5 years. In this conversation, drawing on audio clips from their coaching sessions, they trace a single belief - that Tom's job was to keep everyone happy - through two decisions, years apart: a Series A term sheet he nearly signed because he felt he owed someone, and the decision to sell the startup he'd built.What changed between those moments was whose voice he decided to trust.ABOUT TOMFounder CEO of Forage (YC W19), which built online job simulations for companies like J.P. Morgan, Goldman Sachs, and Verizon to train and hire students right out of college. Tom went through YC in winter 2019, raised a Series A in 2020, scaled revenue to $10 million ARR, and was acquired in 2024.IN THIS EPISODE00:00 Why Amy made this show05:56 From law to a kitchen in Palo Alto to YC07:52 Why Tom reached out to a coach10:02 Alone, uncertain, and people-pleasing15:29 The Series A and imposter syndrome19:42 The term sheet29:25 The acquisition38:48 A coaching session, replayed43:34 From alone and uncertain to peace45:12 Amy on integrityRead more, with related essays: scaleyourself.com/the-user-manual/scaling-founders-tom-brunskillProduced by Kathleen Quillian and Mickey Capper. Music by Scott Bell.