Which Version of Me is Coming to Dinner Tonight

Which Version of Me is Coming to Dinner Tonight

Author: Startups.com August 3, 2026 Duration: 43:50

Ever wonder which “version of you” should show up to dinner, a board meeting, or a team update? This episode breaks down why founders feel like they’re constantly auditioning different personas—optimistic forecaster, calm leader, guarded partner—because the honest answer (“I don’t know” or “we’re struggling”) can carry real consequences with investors, employees, customers, friends, and family. The conversation explores the difference between confidence about an uncertain future versus crossing into deception, the emotional burn rate founders pay to stay composed, and how compartmentalization becomes muscle memory—even through illness, grief, or shutdowns. They highlight how group dynamics push founders to match the room’s tone, and why having one place to take the mask off—like a trusted founder group—can be essential to staying sane and healthy.

03:27 First Pitch Meeting Lesson
04:33 Choosing What To Share
07:26 Buckets Of Consequence
15:54 Gray Area Of Belief
19:07 Founder Pressure Cooker
20:50 Founder Groups And Leaks
27:55 Working Through Pain
30:52 Joy Versus Consequence
36:23 Honesty Sets The Tone
42:06 You’re Not Alone

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/


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: 50

Startup Therapy
Podcast Episodes
What if we run out of goals? [not-audio_url] [/not-audio_url]

Duration: 40:59
In this episode of the Startup Therapy Podcast, Ryan and Will talk about what happens when you hit all your big goals and realize there might not be any more mountains left to climb. They discuss the complex feelings and…
Founders, Reinvention IS your Constant! [not-audio_url] [/not-audio_url]

Duration: 41:06
Will and Ryan talk about the fascinating and often overlooked journey of reinventing oneself. Will shares his diverse background, from being an ad guy to becoming a multi-time startup founder, and stresses the importance…
Founder Isolation is Getting Worse [not-audio_url] [/not-audio_url]

Duration: 40:22
Ryan and Will talk about the growing isolation that founders are feeling despite having more ways to connect. They delve into how the shift to remote work, the impact of social media, and the rise of AI have contributed…
Forging Founder Confidence [not-audio_url] [/not-audio_url]

Duration: 39:22
Ryan and Will discuss the journey of becoming a confident founder. Celebrating their 300th episode, they reflect on how learning to lead and building confidence starts with curiosity. They emphasize asking questions, eve…
Is College a Waste of Time for Founders? [not-audio_url] [/not-audio_url]

Duration: 41:25
In this episode of The Startup Therapy Podcast, Ryan and Will discuss the true value of a college education for aspiring entrepreneurs. They explore whether the traditional path through higher education is the best route…
Are We Preventing Our Startup From Evolving? [not-audio_url] [/not-audio_url]

Duration: 29:10
The realities of evolving a startup. Ryan and Will discuss how the first idea is rarely the final solution, sharing insights on how to navigate the pivoting process. Using Uber and their own experiences at startups.com a…
Building a Startup That Loves You Back [not-audio_url] [/not-audio_url]

Duration: 31:12
Ryan and Will delve into the complexities of maintaining a healthy relationship with your startup. They discuss their personal experiences and challenges in balancing the demands of a startup with personal well-being. Wi…
When Our Friends Resent Our Success [not-audio_url] [/not-audio_url]

Duration: 43:01
Ryan and Will discuss the surprising reactions founders often face when they achieve success. They explore how unexpected resentment from friends and peers can arise, why it happens, and how to navigate these tricky soci…
When Our Startup Outgrows Us [not-audio_url] [/not-audio_url]

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 f…