When is Enough, Enough?

11/08/2025 40 min Episodio 307
When is Enough, Enough?

Listen "When is Enough, Enough?"

Episode Synopsis


Ryan and will talks about a critical issue many founders face: knowing when to say 'enough is enough.' They explore the constant pursuit of growth both personally and professionally and how it can turn into a liability if not checked. They dive into the psychological roots of why founders struggle with the concept of 'having enough,' the impact of a scarcity mindset, and the importance of recognizing diminishing returns. The hosts share personal anecdotes and offer practical advice on how to balance ambition with fulfillment, emphasizing the need for diversified 'buckets' of happiness beyond just business success.Resources:Startup Therapy Podcast https://www.startups.com/community/startup-therapyWebsitehttps://www.startups.com/beginLinkedIn https://www.linkedin.com/company/startups-co/Join our Network of Top Founders Wil Schroterhttps://www.linkedin.com/in/wilschroter/Ryan Rutanhttps://www.linkedin.com/in/ryan-rutan/What to listen for:00:07 The Founder’s Dilemma: Knowing When Enough is Enough01:26 The Scarcity Mindset and Its Impact02:35 The Law of Diminishing Returns03:12 Personal Anecdotes on Ambition and Satisfaction05:38 The Concept of Utility in Economics12:00 Balancing Growth and Happiness in Startups16:56 Post-Exit: The Risk of Overreaching20:11 The Downfall of a Legend21:15 The Cost of Ambition22:32 The Utility of Wealth23:25 Chasing More: A Founder’s Dilemma25:42 The Search for True Happiness28:48 Redefining Success33:50 Balancing Ambition and Value