This week on Earn Your Leisure, we sit down with Sonny Adams and Dave Salvant, the co-founders of Squire, to break down how they built a barbershop tech platform into a $750 million company. They share how they met, landed their first customers, and built their first product without deep technical skills — including why they gave Squire away for three years before ever charging. The conversation dives into the realities of fundraising, from relying on angel investors to survive, taking 60 meetings to secure one VC, and how an $8 million Series A helped unlock massive growth. Sonny and Dave also explain the role Y Combinator played, the strings attached to outside capital, ownership dilution, and what investors truly expect when they invest. We also explore how Squire scaled to 32,000 barbers and 10 million customers, what their $750M valuation actually means, and the challenges of being two Black founders raising capital. Plus, we discuss Squire’s marketing strategy, deploying $100 million in one year, and whether AI or rising haircut costs could disrupt the barber industry. EYL University: https://eyluniversity.com #EarnYourLeisure #Squire #SonnyAdams #DaveSalvant #StartupJourney #Fundraising #VentureCapital #BlackFounders #Entrepreneurship #TechStartups