The Startup Different Podcast
The Startup Different Podcast is here to help bootstrapped startups go from $0 to $5M in annual revenue. Why? Because that's what hosts (and brothers) Dave and Chris Sinkinson did. They know their stuff - the brothers would go on to sell their bootstrapped business for $40M. Startup Different gives you proven ideas and frameworks that can help you create, build, and scale a profitable business. Dave and Chris bring on some of the most exciting entrepreneurs to tackle tough early business challenges, provide tactical insight, and dispel startup myths to reach you startup dreams.
Episodes
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...
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 sandwich. It’s startup different!
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.
It’s Season Six of Startup Different! This season comes loaded with a bunch of crazy stories, like trying to close your latest round of funding the day the market has a historic collapse, a firefighter market flipped upside down, and a tinder swindling senior employee. It’s a wild ride.
We're Dave and Chris and this is Startup Different. We’re tracking down the craziest startup stories and paying it forward to entrepreneurs with a...
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, the discussion touches on the inte...
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 complexities of offshoring development. H...
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 unique features of the Goldminds app...
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