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
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]

Duration: 37:39
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]

Duration: 34:35
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…

«1...678910