When Our Startup Outgrows Us

When Our Startup Outgrows Us

Author: Startups.com May 10, 2025 Duration: 25:59

In this episode of the Startup Therapy Podcast,Ryan and Will delve into the emotional journey of startup founders who feel out of place in the very companies they built from scratch. They discuss the guilt and struggle founders experience when their roles change and they no longer enjoy their jobs. They share personal anecdotes and examine the impact of forced roles, from management misfits to a loss of personal fulfillment. The duo also explores the concept of evolving with or beyond your startup, and how to come to terms with these difficult but often necessary transitions.

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:
00:48 The Shift from Building to Managing

01:29 The Struggles of Management

02:13 The Evolution of Roles

04:17 The Peter Principle in Action

05:29 The Emotional Toll of Management

08:34 Reflecting on the Past and Moving Forward

09:57 The Realization and Acceptance

12:39 The Dilemma of Founder Evolution

13:10 Learning from the Past

13:42 Commitment and Introspection

15:02 The Cost of Doing What You Hate

17:40 Recognizing and Embracing Change

20:16 The Hard Decision to Move On

25:03 Celebrating Growth and Moving Forward


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
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…
How We Secretly Lose Control of Our Startups [not-audio_url] [/not-audio_url]

Duration: 37:28
In this episode of the Startup Therapy Podcast, Ryan and Will discuss the complex dynamics of maintaining control in a startup. They explore the misconception that not having investors means maintaining control and highl…
Should Kids Follow in our Founder Footsteps? [not-audio_url] [/not-audio_url]

Duration: 36:25
In this episode of the Startup Therapy Podcast, Ryan and Will explore the complexities of encouraging their children to become entrepreneurs. With nearly 300 episodes discussing the founder's journey, they delve into whe…
The Evolution of Entry Level Workers [not-audio_url] [/not-audio_url]

Duration: 46:31
In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Will Schroter discuss the evolving landscape of entry-level hiring for startups. They dive into why U.S. college graduates have fallen to the fourth pi…
Assume Everyone Will Leave in Year One [not-audio_url] [/not-audio_url]

Duration: 32:31
In this episode of the Startup Therapy Podcast, Ryan and Will discuss the challenges of managing early-stage startup teams, particularly the high likelihood of turnover and the risks of handing out equity prematurely. Th…