The Startup Different Podcast

What happens after you exit your startup and don't want a boss again? Taylor Crane shares how that moment led to a new way of working—and a new way of thinking about early hires. We dig into product lessons, co-founder dynamics, and what fractional roles look like behind the scenes. Plus, we cover when bringing on part-time leadership is actually smarter than hiring full-time.

She quit her job, had no funding, and started fermenting cider in a garage with her husband. What could go wrong?! Hint: it's not what you think. Within a year, Alicia Hardman and her hubby were running a 10,000 sq. ft. winery with lines out the door—thanks in part to a viral swing table. But what happens when your startup grows faster than you can manage? Was all that growth a good thing?

When COVID wiped out her luxury event business, Virginia Frischkorn didn’t just survive—she reinvented. By turning her workflows into software, she launched Partytrick, a SaaS company now on track for $15M ARR. What started in crisis became a better business than she ever imagined.

Before she turned 22, Jodie Cook had worked 15 different jobs — from mystery shopping to football stadiums. That wild ride set her up for a seven-figure exit, a global digital nomad life, and her latest venture, Coachvox. In this episode, Jodie shares how early hustle shaped her entrepreneurial mindset and why AI is the next frontier for scaling personal brands.

Retail investors represent 53% of the investing market. 🤯

In this episode, we break down our chat with Jane Crowell of Particle Capital and what founders get wrong about funding. We explore smarter paths to capital, the rise of retail investors, and why founder-led sales still matter. Plus, the mindset shift that separates resilient entrepreneurs from the rest.

Tired of chasing VCs and getting ghosted? Jane Crowell drops in to share how Particle is flipping startup funding on its head—connecting founders to capital without the pitch deck circus. If fundraising feels like a full-time job, this episode shows you how to skip the grind and get back to building.

Ever heard of someone getting robbed—only to land their dream job days later?

Melissa Cash’s journey from Disney to co-founding Pok Pok is full of wild turns, but her startup’s genius lies in something deceptively simple: it’s intentionally a bit boring. In this episode, we explore how quiet design, thoughtful screen time, and serendipitous moments led to a kids’ app that actually respects how kids play.

What does it take to build a billion-dollar company from scratch—in one of the toughest, most regulated industries in the world? Brice Scheschuk, co-founder of Wind Mobile, joins us to unpack the raw, real story behind a $1.6B exit that nearly didn’t happen. From regulatory wars to hiring 1,000 people in a single year, this is a gritty, no-BS blueprint for scaling a unicorn under fire.

What if the second half of your life held more purpose than the first? Physician-turned-founder Brian Mahoney shares how a midlife pivot and a deep sense of mission led him to launch a startup transforming surgery recovery—before the surgery even starts.

From selling bootleg software as a teenager to exiting a successful SaaS company, Anthony’s entrepreneurial journey is nothing short of fascinating. In this recap, we break down the hustle, the bold pivots, and the key lessons from his story—like why fearlessness in sales matters and how spotting the right opportunity can change everything. Plus, we debate whether entrepreneurs are truly 'born' or 'made.' Welcome to Startup Different!