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
Did I Just Get Promoted or Fired? [not-audio_url] [/not-audio_url]

Duration: 42:29
Ever wonder what happens when a founder gets 'promoted' out of the CEO role? Ryan and Will dive into the tricky terrain of founder transitions, exploring how it feels to be nudged into roles like Chief Vision Officer or…
Burnout is a Treatable Injury [not-audio_url] [/not-audio_url]

Duration: 39:42
Ever felt like burnout is inevitable in your startup journey? You're not alone. Burnout can feel like a silent co-founder, but it doesn't have to signal the end of your entrepreneurial story. In this episode, we discuss…
Stop Pretending You Don't Have Enough Time! [not-audio_url] [/not-audio_url]

Duration: 40:11
Ever feel like you need more hours in the day? Turns out, you don't. In this episode, we dive deep into time management for founders, starting with a viral Reddit post that stirred some controversy. We'll explore how com…
Are Founders Aligned with Those Around Them? [not-audio_url] [/not-audio_url]

Duration: 40:33
The complexities of alignment among founders, employees, and even spouses. They debunk the notion that perfect alignment exists, emphasizing that often, perceived alignment is more fiction than reality. The conversation…
Will the Payout be Worth the Sacrifice? [not-audio_url] [/not-audio_url]

Duration: 44:13
The challenging question of whether the sacrifices made in pursuit of entrepreneurial success are ultimately worth the payoff. Will retells his personal story of almost buying an expensive house in Bel Air only to realiz…
How Founders Blow Their Fortunes [not-audio_url] [/not-audio_url]

Duration: 47:21
The critical do's and don’ts after a big financial win as a startup founder. They emphasize the importance of not oversharing about your wealth, shifting from an offensive to a defensive mindset, preserving your gains, a…
When is Enough, Enough? [not-audio_url] [/not-audio_url]

Duration: 40:37
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 i…
Can Entrepreneurship Alleviate Poverty? [not-audio_url] [/not-audio_url]

Duration: 47:57
How entrepreneurship can transform lives and communities? Will shares his personal journey from a challenging childhood to becoming a successful entrepreneur. They explore whether entrepreneurship can be a means to allev…
Should Startups Be a Family? [not-audio_url] [/not-audio_url]

Duration: 37:22
In this episode of the Startup Therapy Podcast, Ryan and Will discuss the challenges and dynamics of blending friendship and professionalism in startups. They delve into the potential pitfalls of treating your startup te…
Can Founders be Replaced by AI? [not-audio_url] [/not-audio_url]

Duration: 38:05
Ryan and Will talk about the growing role of AI in startups. They explore how AI is automating traditional founder tasks like writing, coding, and analyzing data. The conversation delves into the existential threat AI po…