You Only Have to Be Right Once

You Only Have to Be Right Once

Author: Startups.com February 24, 2025 Duration: 32:58

In this episode of the Startup Therapy podcast, Ryan and Will chat about how startup success isn’t always a straight path. They use Mark Cuban’s story as a prime example, showing why sticking it out for the long run is so important—because success can happen at any time in a founder’s career. They also talk about how those early small wins can build up to something bigger and why setting strict timelines for success doesn’t really make sense. At the end of the day, one big right moment in a 50-year career can be a total game-changer.

Sign up for the Startups Newsletter
https://www.startups.com/newsletter

Resources:
Startup Therapy Podcast 
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn 
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders 
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
00:07 The Reality of Founders' Success

02:00 Mark Cuban's Journey to Billionaire Status

06:35 The Importance of Small Wins

10:15 Financial Stability and Early Success

15:57 The Value of Consistent Small Wins

18:02 Success Doesn't Have a Timeline

18:12 When Does Success Happen?

18:20 Examples of Late Bloomers

18:45 The Myth of Early Success

19:59 The Impact of Timing

20:44 The Internet Era and Young Wealth

21:40 Outliers and Unrealistic Expectations

25:13 Consequences of Chasing Quick Success

27:28 The Value of Longevity in Business

30:02 Unexpected Success Stories

31:46 Staying in the Game

32:36 Join the Startups.com Community


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
It's really HARD to REPEAT A WIN [not-audio_url] [/not-audio_url]

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 boo…
Does LOCATION matter for your startup? [not-audio_url] [/not-audio_url]

Duration: 36:57
Ryan and Will discuss the evolution of startup location strategies. They reminisce about the bygone era when relocating to major hubs like San Francisco was essential for success due to access to talent, investors, and n…
Are The Sacrifices Worth It? [not-audio_url] [/not-audio_url]

Duration: 47:45
In this episode of the Startup Therapy Podcast, the guys tackle the big question: was the entrepreneurial journey worth it? They discuss the sacrifices, the missed experiences, and the immense pressures that come with be…
Are Founders Forged Over Youth? [not-audio_url] [/not-audio_url]

Duration: 43:45
In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter discuss how childhood experiences influence the entrepreneurial journey. They explore why many founders' origin stories trace back to their ear…
Assets OVER Exits [not-audio_url] [/not-audio_url]

Duration: 39:42
In this episode of Startup Therapy, Ryan Rutan and Will Schroeter challenge the startup world's focus on big exits and venture capital. They highlight the benefits of cash-flowing businesses, showing how consistent profi…
What Would I do Differently [not-audio_url] [/not-audio_url]

Duration: 33:18
In this episode of The Startup Therapy, Ryan Rutan and Will Schroter explore the 'what if' scenarios that often preoccupy founders. Will shares personal milestones, showing how taking bigger risks shaped his journey. The…
When Can I Afford to GAMBLE? [not-audio_url] [/not-audio_url]

Duration: 30:41
In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter dive into an interesting perspective: taking risks in entrepreneurship is actually a luxury, not the norm. They break down what it really costs…
Can Founders Find Contentment? [not-audio_url] [/not-audio_url]

Duration: 43:19
In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroeter delve into the anxiety surrounding contentment in the startup ecosystem. They question the conventional wisdom that equates contentment with s…
Why do Investors FIRE Founders? [not-audio_url] [/not-audio_url]

Duration: 45:48
Ryan Rutan and Will Schroeter discuss the complexities and challenges faced by startup founders, particularly the frequent occurrence of founders being replaced by investors. The conversation delves into the motivations…
The Burden of Unrealistic Expectations [not-audio_url] [/not-audio_url]

Duration: 38:00
In this episode Ryan and Will delve into the intense pressures faced by founders from investors, peers, and the startup community. They discuss how these external expectations often drive founders to pursue goals misalig…