Podcast Episodes
Back to SearchBetter is Better than Bigger
Episode 318
Is getting bigger always better for startups? This episode dives into the hidden costs of scaling up and how growth can sometimes make a company wors…
8 months ago
Founder Authenticity: Use with Caution
Episode 317
Ever wonder if being your authentic self at work might sometimes do more harm than good? The delicate balance of authenticity and diplomacy in leader…
8 months, 1 week ago
Founders, 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 d…
8 months, 2 weeks 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 ev…
8 months, 3 weeks 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 …
9 months 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, explo…
9 months, 1 week 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 sig…
9 months, 2 weeks 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…
9 months, 2 weeks 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 oft…
9 months, 4 weeks 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 perso…
10 months ago