The Unsure Entrepreneur
Are you thinking about starting your own business? Know what you're getting into — before you commit. If you're an aspiring entrepreneur grappling with doubts, or just curious about the self-employed life, this podcast demystifies the entrepreneurial process by sharing stories and insights of founders who have successfully launched and built a small business.
Episodes
Lubaina shares how she built a Canadian food company around organic date sugar, date powder, and date syrup.
A diagnosis of gestational diabetes during her third pregnancy pushed Lubaina Rakla to rethink sugar. After other sweeteners caused blood sugar spikes and gut problems, she found date sugar. The change helped her balance her blood sugar and improve her health. It also gave her the idea for Liva Foods and she's never looked b...
Dreaming of starting a business and making it bigger? You'll likely need to hire some help.
Hiring your first employee is a major milestone, but it also brings payroll, legal, and management responsibilities many founders underestimate. Roger Pierce speaks with Sharilyn Vandermolen, founder of HR Collab, a fractional HR consultancy that helps small businesses build strong hiring and people systems.
Sharilyn is a Certified Human Resou...
At only 16, Chanelle Chalazan has already spent three years building Chic & Charmed Boutique, a Canadian jewelry business focused on affordable 925 sterling silver pieces. She began selling handmade earrings through Facebook Marketplace at age 13. What started with one customer coming to the family home each day grew to 20, then expanded into online sales, trade shows, radio campaigns, and billboards.
Chanelle tells the Unsure E...
Are you waiting for the perfect time to start a business? Steve Strauss says this may be it.
“This really is, I think, the golden age of entrepreneurship.”
One of America’s best-known small business voices, Steve is the bestselling author of The Small Business Bible and 17 other business books. He spent more than 20 years as USA Today’s senior small business columnist, now writes for Inc., and was named by SC...
Marvin Garellek, known as the Montreal Finance Guy, joins Roger Pierce to discuss one of the biggest challenges facing entrepreneurs: access to capital. In this episode, Marvin breaks down the realities of business financing, explaining why banks are lenders rather than investors, what entrepreneurs need to qualify for funding, and the common mistakes that prevent business owners from securing the capital they need. He shares pract...
Roger Pierce sits down with Lisa Taylor, founder and CEO of Challenge Factory, to explore how careers, and entrepreneurship are evolving in a world shaped by AI, longer working lives, and constant change.
Lisa explains the concept of “broken talent escalators” and why many workplace systems still operate on assumptions created decades ago, despite dramatic shifts in demographics, technology, and workforce expectations.
Th...
“You’re an entrepreneur. You’re in charge of everything — that comes with a lot of responsibility, but it comes with a lot of freedom.”
In this episode, Leigh Mitchell turns the mic around and interviews Roger Pierce about his book, The Unsure Entrepreneur. Leigh is the founder of Women in Biz Network, host of the ChangeMaker Leader Podcast, and an entrepreneurship and digital marketing instructor...
In this special episode of The Unsure Entrepreneur Podcast, Roger Pierce talks with friend Evan Carmichael — author, speaker, and one of the top business content creators on YouTube with 4.5 million subscribers. Evan has built a global following by sharing entrepreneurship insights and lessons from top performers, all while championing one core idea: #Believe in yourself.
They dig into a gap that’s tough to ignore: schoo...
Discover realities many new entrepreneurs overlook.
One of the most respected small business experts in the U.S., Barbara Weltman is an attorney, founder of Big Ideas for Small Business, and bestselling author of J.K. Lasser’s Small Business Taxes 2026, 500+ Big Ideas for Your Small Business, and the Home-Based Business Start-Up Guide. Called the “guru of small business taxes” by The Wall Street Journal, Barbara ha...
Listen to this episode to learn about the kind of leadership that builds trust, strong teams, and lasting businesses — and discover a great new book about exactly that.
Bruce Mayhew has spent more than 20 years helping executives, managers, and entrepreneurs improve communication skills, boost leadership development, and increase organizational performance. He's just released an exciting new book called The Path of an Inspired...
Your pitch deck may be solid — but people often decide whether they trust you before you even finish the first slide.
Host Roger Pierce interviews Mark Bowden, ranked the World’s #1 Communication Keynote Speaker (Global Gurus 2026) and voted three-times as the #1 Body Language Professional in the world. Mark is the founder of Truthplane.com, a bestselling author, and co-host of The Behavior Panel — one of YouTube's...
Emile Maamary is co-founder and Chief Marketing Officer of Steadiwear, a Canadian health tech company developing non-invasive solutions for people living with Parkinson’s disease and essential tremor. Inspired by their own grandmothers’ struggles, Emile and his co-founder Mark Elias set out to close the gap between medication and surgery.
Their flagship product, the Steadi-3, is a wearable glove that reduces tremors for ...
Jamie Irvine returns to The Unsure Entrepreneur Podcast for a wide-ranging conversation on sales, focus, and the hidden systems that quietly kill growth. With more than 25 years in the heavy-duty parts and trucking industry, and operating several business of his own, Jamie brings a unique view on how businesses actually win and lose revenue.
On his popular podcast The Heavy Duty Parts Report, Jamie and his guests discuss tips, ...
Entrepreneurial ambition in Canada has reached an eight-year high. In this episode of The Unsure Entrepreneur Podcast, Roger Pierce speaks with Karen Svendsen, Senior Director of Small Business and Partnerships at Royal Bank of Canada, about what is driving that surge and what holds people back from getting started.
She helps lead RBC’s national small business strategy and played a central role in the 2025 RBC Small Business P...
Rieva Lesonsky joins the podcast to talk about small business trends, fears, and the changing face of entrepreneurship.
A trailblazer in the world of entrepreneurship advocacy, Rieva worked for 25 years as Editorial Director of Entrepreneur Magazine. She’s a best-selling author of several books, including Start Your Own Business and Small Business Hacks: 100 Shortcuts to Success. She’s written about small business issue...
The conversation explores speak-up culture — what it is, why it matters, and how it drives retention and innovation. Stephen Shedletzky is the author of Speak-Up Culture, a leadership coach, and former member of Simon Sinek’s founding team. Stephen helps leaders create psychologically safe environments where people feel confident using their voices.
Why is this important for entrepreneurs? Employees in speak-up cultures...
Most accountants and bookkeepers are drowning in long hours and underpriced work. Ryan Lazanis says it doesn’t have to be that way.
On this special Accountex 2025 episode of The Unsure Entrepreneur Podcast, Roger Pierce talks with Ryan Lazanis, CPA, Founder of Future Firm. Ryan built and sold Zen Accounting, one of Canada’s first 100% cloud-based firms, and now helps thousands of accounting professionals create modern pr...
Paul Chato has done it all — comedian, CBC exec, web entrepreneur, and YouTuber with 130,000 subscribers. In this episode of The Unsure Entrepreneur Podcast, Paul shares how he went from making Canadians laugh with The Frantics and cult hero Mr. Canoehead to building over 2,000 websites and pioneering a subscription model long before it was cool.
He even explains how doing Rick Green’s taxes (yes, that guy from The Red G...
Whether you’re pitching investors, leading a team, or serving customers, this episode will show you how to strengthen your most valuable entrepreneurial skill: communication.
Host Roger Pierce talks with Ric Phillips, Founder of 3V Communications, to explore why developing communication skills is make-or-break factor for new and existing entrepreneurs.
Ric has been coaching entrepreneurs and professionals since 2006, helping th...
In this episode, longtime business owner Faith Seekings opens up about one of the most personal — and necessary — challenges in entrepreneurship: reinvention. She shares how she moved from building a full-service graphic design agency to becoming a solo content strategist focused on writing, storytelling, and strategic communication.
Faith founded Rapport Communications Inc. and grew it into a thriving agency with 10 emp...
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