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. They discuss the hidden costs of success, the pitfalls of romanticizing alternative outcomes, and the importance of realistic risk assessment. The key takeaway? Embrace risk to avoid the regret of missed opportunities.

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https://www.startups.com/community/startup-therapy
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Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:

00:07 – Reflecting on milestones and 'what ifs'
00:44 – The risks and rewards of entrepreneurship
04:00 – A hilarious temp job experience
07:34 – The reality of alternate paths
09:02 – The danger of romanticizing 'what ifs'
13:48 – The cost of success
15:29 – Building a realistic mental model
16:18 – Stop guessing and get real answers
16:26 – The cost of staying in a job you hate
17:30 – Should you stay or leave?
18:10 – The true cost of success
19:12 – The hindsight trap: romanticizing outcomes
21:56 – Learning from failure and modeling risk
22:55 – Zirtual acquisition: a case study in risk
28:47 – Surviving failure and moving forward
31:35 – Avoiding regret and embracing risk