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 kid...

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...

Anthony shares his remarkable path from selling pirated software as a 12-year-old to building and exiting a 70-employee, bootstrapped e-commerce bundling platform. Now running Daily Body Coach, he explains how his entrepreneurial mindset helps executives maintain peak physical performance while managing demanding business lives. Welcome to Startup Different!

In this episode, we dive into the inspiring and unfiltered journey of Jess Chan, founder of Longplay. From navigating personal challenges to scaling an agency that champions retention marketing, Jess shares valuable insights, startup myths, and a jaw-dropping tale about an employee that sounds like it belongs in a crime-drama.

On the show today, we’ve got Jess Chan, founder and CEO of Longplay. She’s an expert in retention marketing who’s built an eight-figure business, and she’s here to share some seriously useful lessons for entrepreneurs. Oh and she also tells us one of the wildest HR stories ever. It’s Startup Different.

Last week we spoke to the fantastic Rob Levin, seasoned entrepreneur and investor. We deep dive on how he’s an accidental entrepreneur, how he asks for (and gets) money, and the age old debate of Toronto vs Des Moines. Welcome to Startup Different!

Robert Levin is a seasoned investor and operator with a robust background in strategy, growth and mergers and acquisitions. This week we talk to him about what it means to scale a startup worth tens of millions and how to manage the WFIO moments. It's VC, funding, and pivots on Startup Different!

This week we go deep on our interview with Natalie Kaminski of JetRockets. We dig into the mighty middle, the Russian-Ukraine war, and taking all the work you can find. It’s Startup Different!

Today, we’re chatting with Natalie Kaminski, the founder and CEO of JetRockets. She’s a tech entrepreneur with a knack for empathetic leadership and a powerful story about moving her entire company to align with her values.

Today on Startup Different we talk to our old pal, Chris Memmott. He has over 15 years of sales and leadership experience within high-growth startups and has even had his own successful (albeit bumpy!) exit. We’ll cover his journey and what to watch out for when selling your business baby. It’s acquisition time on Startup Different!

In this recap, we’re diving back into our chat with Catherine Bell, where she dropped some incredible gems about mixing purpose and profit as an entrepreneur. Whether it’s building a strong team culture or turning mistakes into growth moments, we’ve pulled together the best insights for you to level up your business game. Bonus : we also press Chris on his Boss-Hole past and is a hot dog a sandwic...

Can you balance profit and purpose? Today’s guest is Catherine Bell, founder of The Awaken Company, and she’s all about transforming how we think about business. From building healthy cultures to leading with self-awareness, Catherine shows how your company can be a force for good while thriving along the way. Welcome to Season 6 of Startup Different.

In this episode of Startup Different, we reflects on the journey of scaling businesses and the importance of exits, while debriefing our conversation with serial entrepreneur Matt Watson. The conversation delves into the significance of having a well-known product over just a good product, the necessity of execution, and the critical role of hiring the right talent at the right time. Additionally,...

In this episode of Startup Different, Matt Watson, a serial tech entrepreneur, shares his journey of founding and exiting multiple startups, including a $150 million exit. He discusses the importance of execution, the challenges of scaling a business, and the role of timing and luck in achieving success. Matt emphasizes the need for product-market fit, the significance of key hires, and the comple...

In this episode of Startup Different, we recap our interview with Cynthia Arscott, the founder of Goldminds, an app designed to help children sleep better. The conversation explores Cynthia's journey from tech to entrepreneurship, the challenges of transitioning from in-person to digital solutions during the pandemic, and the importance of working smarter rather than longer hours. We discuss the u...

In this episode of Startup Different, Dave and Chris interview Cynthia Arscott, the CEO and founder of GoldMinds, a mindfulness app for kids. Cynthia shares her personal journey from struggling with anxiety as a child to discovering the benefits of mindfulness and meditation. She discusses the evolution of her business from in-person mindfulness classes to a digital app, especially during the COVI...

Are entrepreneurs in Canada less motivated than their US counterparts? Last week, Matt Reesor gave us his take and identified how Canadian firms need to compete. Today, Chris and I dig deeper into the complexities of the Canada versus US competitive landscape. Welcome to Start Up Different.