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
This is WHY More Money Means MORE Problems [not-audio_url] [/not-audio_url]

Duration: 31:01
Why sometimes, less is more? Ryan Rutan and Will Schroeder discuss the misconception that reaching revenue milestones in startups will solve all problems. Explore how each milestone brings new challenges, why growing lia…
Committees are Where Progress Goes to Die [not-audio_url] [/not-audio_url]

Duration: 29:28
In this episode of the Startup Therapy Podcast, we discuss the inefficiencies and dangers of making decisions by committee. Why committees often fail and why founders should avoid relying on them for critical decisions.…
Giving Up Equity? Press Pause First [not-audio_url] [/not-audio_url]

Duration: 37:54
In this episode of the Startup Therapy Podcast, we talk about equity distribution in startups. Explore the psychological traps of seeking validation, the dangers of making hasty decisions when most vulnerable, and offer…
Why Do 99% of Founders Suck at Asking for Help? [not-audio_url] [/not-audio_url]

Duration: 29:42
In this insightful episode of the Startup Therapy Podcast, Ryan Rutan and Wil Schroter discuss the importance of asking questions as a startup founder.Why founders often hesitate to seek advice, the untapped wealth of kn…
The Value of Actually Getting Paid (Avoid This Big Danger) [not-audio_url] [/not-audio_url]

Duration: 34:28
In this episode of the Startup Therapy Podcast, Ryan Rutan and Wil Schroter, discuss the misconception that startup founders are incredibly wealthy on paper, while in reality, many struggle with personal financial stabil…
Will Investors Bail Me Out? Brutal Truth About Startup Investments [not-audio_url] [/not-audio_url]

Duration: 31:29
In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Wil Schroter talk about sacrifices founders make — accumulating debt and foregone salaries, with the expectation of being reimbursed. They discuss how…
Is the problem the Player or the Coach? Team Building Hacks [not-audio_url] [/not-audio_url]

Duration: 35:10
In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Wil Schroter delve into evaluating startup team and management performance. Find out the importance of constant evaluation, highlighting the significan…
Do people really want me to succeed? Founders vs World [not-audio_url] [/not-audio_url]

Duration: 37:14
In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Wil Schroter explore the harsh reality of seeking support as a founder. Surprising, limited number of people who genuinely want to see a founder succee…
You only THINK you work HARD — The Hard Work Illusion [not-audio_url] [/not-audio_url]

Duration: 31:38
In this episode of the Startup Therapy podcast, hosts Ryan Rutan and Wil Schroter talk about the common misconception around 'working hard' within startups. They question the measurement of hard work, arguing that effort…
SMALL is the New Big - Embracing Efficiency in the Age of AI [not-audio_url] [/not-audio_url]

Duration: 38:59
In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Wil Schroter discuss the evolution of startups from the emphasis on scaling and headcount to prioritizing efficiency and output, largely due to advance…