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
Job vs Startup - What Should I Do? [not-audio_url] [/not-audio_url]

Duration: 37:14
In today's Startup Therapy Podcast, Wil and Ryan discuss whether you should get a steady paycheck or start your own startup. Choosing between a regular job and starting your own business is a big decision many face. Work…
Founders Need a Steady Hand in the Storm [not-audio_url] [/not-audio_url]

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In today's Startup Therapy Podcast, Wil and Ryan discuss the idea of managing chaos as a founder. Keeping a startup on track is like steering a ship through rough waters. Founders must stay calm and focused amid the chao…
So You Think You Need a Co-Founder? [not-audio_url] [/not-audio_url]

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In today's Startup Therapy Podcast, Wil and Ryan discuss the idea of having a co-founder. A co-founder can offer numerous benefits for a business. It allows for shared responsibilities, diverse skill sets, and a support…
Can I Scale My Impact Without Scaling My Team? [not-audio_url] [/not-audio_url]

Duration: 28:09
In today's Startup Therapy Podcast, Wil and Ryan discuss the concept of scaling without adding or hiring more people. Making a significant impact doesn't always mean having a large team. You can achieve remarkable result…
Grind or Guilt, the Founder Dilemma [not-audio_url] [/not-audio_url]

Duration: 43:41
In today's Startup Therapy Podcast, Wil and Ryan discuss about the grind and guilt dilemma of founders. Founders often struggle with the never-ending hard work of growing their business, driven by their passion and ambit…
Are Founders Driven by Fear or Greed? [not-audio_url] [/not-audio_url]

Duration: 26:33
In today's Startup Therapy Podcast, Wil and Ryan discuss whether founders are driven by fear or greed. In the world of startups, there's a question that keeps coming up: what drives founders? Is it the fear of failure, o…
What if I'm Building the Wrong Product? [not-audio_url] [/not-audio_url]

Duration: 37:34
In today's Startup Therapy Podcast, Wil and Ryan discuss how you as a founder will know if you’re building the right or wrong product. Have you ever had an idea, but you're just not sure if it's good? It's something that…
How Startups Actually Get Bought [not-audio_url] [/not-audio_url]

Duration: 30:55
In today's Startup Therapy Podcast, Wil and Ryan discuss how startups are actually bought and sold. The process of buying and selling startups can be tricky. It's easy to get confused about how much a startup is really w…
Am I Quitting My Startup, Or Letting Go? [not-audio_url] [/not-audio_url]

Duration: 29:05
In today's Startup Therapy Podcast, Wil and Ryan discuss when to quit or let go of your startup. If your startup has struggled for an extended period without meaningful progress, causing financial strain, and lacks marke…

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