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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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
The Spectrum of Investor Advice [not-audio_url] [/not-audio_url]

Duration: 43:24
In this episode of the Startup Therapy Podcast, Ryan Rutan and Wil Schroter discuss the complexities of handling feedback from investors, emphasizing the critical need for founders to properly qualify and assess the advi…
$10K Per Month isn't Just Revenue. It's Life Support [not-audio_url] [/not-audio_url]

Duration: 31:52
In today's Startup Therapy Podcast, Wil and Ryan talks about why earning atleast $10,000 per month is one of the most important milestones in your startup career. They stress the need to do whatever it takes to keep your…
Why Do VCs Keep Giving "failed" Founders Money? [not-audio_url] [/not-audio_url]

Duration: 33:42
In today's Startup Therapy Podcast, Wil and Ryan talks about why investors choose to invest on “failed” founders. They debunk the myth that failure marks the end of a founder's journey and shows why giving people a secon…
If It Makes Money, It Makes Sense [not-audio_url] [/not-audio_url]

Duration: 38:09
In today's Startup Therapy Podcast, Wil and Ryan talks about the importance of generating revenue and being willing to do whatever it takes to move a startup forward. They discuss why it's crucial for entrepreneurs to pr…
The Hidden Treasure of Failed Startups [not-audio_url] [/not-audio_url]

Duration: 35:48
In today's Startup Therapy Podcast, Wil and Ryan talks about the hidden treasure of failed startups. From redefining valuation to creative acquisition strategies, they share insights on salvaging value from adversity. Tu…
My Competitors Just Raised Funds - Am I Screwed? [not-audio_url] [/not-audio_url]

Duration: 36:25
In today's Startup Therapy Podcast, Wil and Ryan talks about what happens if your competitor got funded. Join as they discuss the common concern of competitors securing funds and share valuable perspectives on why this m…
Can Having Zero Experience Be a Huge Asset? [not-audio_url] [/not-audio_url]

Duration: 33:53
In today's Startup Therapy Podcast, Wil and Ryan explore whether lacking prior experience can be a game-changer for startup founders. Having zero experience means you're new to something, and surprisingly, that can be a…
What If I Build a Startup That Just Makes Money? [not-audio_url] [/not-audio_url]

Duration: 31:19
In today's Startup Therapy Podcast, Wil and Ryan talks about whether a founder should focus on building a startup that just makes money. Ever thought about ditching the whole fundraising craze and simply building a start…
How to Get Rockstar Startup Advisors [not-audio_url] [/not-audio_url]

Duration: 41:07
In today's Startup Therapy Podcast, Wil and Ryan discuss how you can get rockstar advisors for your startup. Discover the common mistakes people make when they are getting people to be their advisors and what are the bes…