It's really HARD to REPEAT A WIN

It's really HARD to REPEAT A WIN

Author: Startups.com April 1, 2025 Duration: 31:25

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.

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Wil Schroter
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Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:

01:01 The Rise and Fall of Wish
03:01 Lessons from the Wish IPO
05:15 The Psychology of Founders
11:52 A Counter Story: Priceline's IPO
15:13 Reflecting on High School Memories
15:37 The Illusion of Endless Wealth
15:51 The Reality of Financial Downturns
19:09 Understanding Venture Capital Statistics
21:28 The Rarity of Repeat Success
24:18 Advice for Founders: Secure Your Wins
28:11 The Importance of Financial Safety
30:39 Final Thoughts: Keep the Win


Building a company is far more chaotic and personal than any business school case study lets on. Startup Therapy from Startups.com digs into that reality, moving past polished success stories to focus on the raw, unvarnished journey. Hosts Wil Schroter and Ryan Rutan, who have each navigated these trenches themselves, lead conversations that feel more like essential conversations between founders than a standard interview show. They tackle the specific pressures that come with trying to transform an idea into something meaningful-the financial strain, the team dynamics, the personal sacrifices, and the frequent moments of doubt that rarely make the keynote speech. This podcast operates on a simple premise: the best guidance comes from those who have been there, not from abstract theory. Each episode is a candid session, dissecting the professional hurdles and the intense emotional toll that founders manage daily. You’ll hear direct talk about fundraising fails, partnership conflicts, burnout, and the small victories that keep everything moving forward. It’s a resource for anyone in the thick of building something, offering practical perspectives and a sense of shared experience when the path gets especially tough. The dialogue is straightforward and focused on actionable insight, providing a genuine look at the resilience required to change the world, one startup at a time.
Author: Language: English Episodes: 100

Startup Therapy
Podcast Episodes
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Ryan and Will delve into the complexities of maintaining a healthy relationship with your startup. They discuss their personal experiences and challenges in balancing the demands of a startup with personal well-being. Wi…
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Duration: 43:01
Ryan and Will discuss the surprising reactions founders often face when they achieve success. They explore how unexpected resentment from friends and peers can arise, why it happens, and how to navigate these tricky soci…
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Duration: 50:24
Dive into the common struggle founders face with burnout and the inability to truly relax. Ryan and Will share their personal experiences and discuss how traditional relaxation methods often fail for them. Instead, they…
You probably should be TERRIFIED. At least a bit.. [not-audio_url] [/not-audio_url]

Duration: 31:19
Ryan and Will discuss the prevalent fear in the market due to economic uncertainty in April 2025. They delve into how fear is a constant companion for founders and argue that it's not a weakness but a strength. Drawing o…
Make Money First - Then Make a Product [not-audio_url] [/not-audio_url]

Duration: 41:00
In this episode, Ryan and Will discuss the common misconception that startups need funding before generating revenue. They emphasize that the actual business isn't just the product but the revenue it generates. The discu…