When Being in the 1% Feels like Failure

When Being in the 1% Feels like Failure

Author: Startups.com April 29, 2025 Duration: 34:27

Ryan and Will discuss the psychological challenges founders face by constantly looking ahead and rarely celebrating their achievements. They explore how important it is for founders to practice gratitude and recognize their progress, even if their ultimate goals haven't been reached. The conversation delves into personal experiences, including Ryan's move to Guatemala and Will's time in Beverly Hills, highlighting how perspective and gratitude can significantly impact one’s satisfaction and motivation in their entrepreneurial journey.

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:
00:29 The Psychological Cost of Milestones
00:58 The 1% of Startups
02:01 Celebrating Small Wins
02:38 The Comparison Trap
03:45 Balancing Credit and Complacency
04:33 Contrasting Success Stories
09:14 Perspective on Startup Success
16:26 The Olympic Mindset and Startup Mentality
17:39 The Power of Perspective and Gratitude
19:35 Balancing Ambition and Gratitude
21:16 Family Traditions and Simple Joys
22:47 Reinforcing Self-Worth and Capability
28:19 The Curse of the Exited Founder
31:02 Changing Perspectives for Greater Happiness


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
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…
How do I Stay Positive In Tough Times? [not-audio_url] [/not-audio_url]

Duration: 43:37
Ryan and Will discuss the omnipresent challenges that come with running a startup. They delve into the perpetual 'shit storm' that founders face and share practical advice on how to keep moving forward even when everythi…
Are Investors Trying to Push Us a Cliff? [not-audio_url] [/not-audio_url]

Duration: 20:06
In this episode of the Startup Therapy Podcast, Ryan and Will delve into the often misunderstood motivations of venture capitalists. They discuss why investors push startups to grow rapidly, the pressures VCs face to del…
What Previously Funded Founders Do Differently [not-audio_url] [/not-audio_url]

Duration: 33:21
In this episode of the Startup Therapy Podcast, Ryan and Will discuss the daunting realities of raising capital for startups. By sharing insights and experiences from both first-time and repeat founders, they delve into…
Are Startups Easier for Experienced Founders? [not-audio_url] [/not-audio_url]

Duration: 33:01
In this episode of the Startup Therapy Podcast, Ryan and Will debunk the myth that each startup venture becomes progressively easier with experience. They explore the truths and fallacies surrounding repeat entrepreneurs…
Who's Working for Who? [not-audio_url] [/not-audio_url]

Duration: 32:28
Ryan Rutan and Will Schroter explore the intricate and often misunderstood relationship between founders and their startups. They tackle the question of whether the founder works for the startup or vice versa, challengin…
Let's Get Back to Our WHY [not-audio_url] [/not-audio_url]

Duration: 36:35
In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter explore the vital importance of maintaining a startup's foundational 'why' – the core reason for its existence. They discuss the excitement and…