Podcast Episodes
Back to SearchFounders, Embrace Your Flaws
Episode 316
Are you convinced that you need to fix all your flaws as a founder? In this episode, we explore why that's not necessarily true. Ryan and Will dive deep into the idea that both startups and their fou…
Published on 14 hours ago
Is Remote Culture, Actually Culture?
Episode 315
Have you ever wondered if remote work is better than being in the office? Ryan and Will dive into their experiences and how their work culture has evolved over 20 years. They discuss the pros and con…
Published on 1 week, 1 day ago
Can I Hand Off My Startup?
Episode 314
Ever dreamt of handing off your startup to a killer operator and sipping margaritas while the money keeps rolling in? It sounds perfect, but reality often has other plans. In this episode, we break d…
Published on 2 weeks, 1 day ago
Did I Just Get Promoted or Fired?
Episode 313
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 Chi…
Published on 3 weeks, 1 day ago
Burnout is a Treatable Injury
Episode 312
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…
Published on 4 weeks, 1 day ago
Stop Pretending You Don't Have Enough Time!
Episode 311
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. …
Published on 1 month ago
Are Founders Aligned with Those Around Them?
Episode 310
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 reali…
Published on 1 month, 1 week ago
Will the Payout be Worth the Sacrifice?
Episode 309
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 B…
Published on 1 month, 2 weeks ago
How Founders Blow Their Fortunes
Episode 308
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, pre…
Published on 1 month, 3 weeks ago
When is Enough, Enough?
Episode 307
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 tu…
Published on 2 months ago