In this episode of the Startup Therapy Podcast, Ryan and Will debunk the myth that each startup venture becomes progressively easier with experience. They explore the truths and fallacies surrounding repeat entrepreneurship, sharing personal anecdotes and insights from their extensive history of building and acquiring startups. Discussing expectation management, the double-edged sword of experience, and the harsh realities of repeating past mistakes, Ryan and Will emphasize that while experience offers certain advantages, it does not guarantee success in new ventures. They also highlight the emotional resilience required to endure the cyclical nature of startup challenges and the ever-present difficulties of achieving product-market fit and successful marketing, regardless of prior victories.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/community/st...Websitehttps://www.startups.com/beginLinkedIn   / startups-co  Join our Network of Top Founders Wil Schroter  / wilschroter  Ryan Rutan  / ryan-rutan  What to listen for:00:15 Debunking the Myth of Easier Startups01:27 The Double-Edged Sword of Experience02:32 Drawing from Multiple Experience Buckets05:15 Expectation Management in Startups09:39 Avoiding Duplicate Mistakes13:01 Raising Capital: Lessons Learned15:16 The Value of Experience in Decision Making17:07 The Reality of Investor Promises17:17 Understanding People: A Founder's Key Skill18:38 Emotional Maturity in Leadership20:00 Challenges That Never Get Easier21:57 The Ever-Changing Landscape of Product Market Fit25:39 Marketing Struggles for Experienced Founders27:40 The Pain of Failure: It Never Gets Easier31:30 The Value of Experience and the Role of Luck32:38 Join the Startups.com Community

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