Will and Ryan discuss the dangerous mindset founders can fall into after hitting it big with their startups. They reflect on the story of Peter Chesky, co-founder of Wish, who became a billionaire during the tech IPO boom of early 2021 but saw his net worth plummet as the company's stock tanked. The episode emphasizes the importance of treating any major payout as if it's the last one you'll ever receive. With only a small percentage of startups ever having significant exits, and even fewer doing it repeatedly, Ryan and Will stress why founders should be cautious with their newfound wealth instead of assuming it will keep flowing.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:01:01 The Rise and Fall of Wish03:01 Lessons from the Wish IPO05:15 The Psychology of Founders11:52 A Counter Story: Priceline's IPO15:13 Reflecting on High School Memories15:37 The Illusion of Endless Wealth15:51 The Reality of Financial Downturns19:09 Understanding Venture Capital Statistics21:28 The Rarity of Repeat Success24:18 Advice for Founders: Secure Your Wins28:11 The Importance of Financial Safety30:39 Final Thoughts: Keep the Win

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