The Unsure Entrepreneur

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 wa...

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...

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 w...

“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 instruc...

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...

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...

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...

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...

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 t...

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 , Ja...

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...

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 ab...

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? Employ...

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 pro...

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...

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 prof...

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 thr...

Is podcasting worth your investment of time, money, and energy? One of the best people I know to answer that question is Jamie Irvine, National Sales Director at Parts for Trucks and seasoned podcast host. Jamie has produced over 150 episodes of the Build a Better Business podcast and 350 episodes of The Heavy Duty Parts Report, giving him rare insight into how podcasting can power business growth...

What if the best way to start a business is to buy one that already exists? In this episode of The Unsure Entrepreneur Podcast , host Roger Pierce speaks with Scott Stirrett , Founder and CEO of Venture for Canada , a national charity helping young Canadians gain entrepreneurial experience and skills. Since 2013, Scott and his team have raised more than $80 million and supported over 10,000 early-...

Most small business owners rely on a part-time bookkeeper and an accountant who shows up once a year. My guest explains why that setup leads to inaccurate financials and lost opportunities: “We lost deals because the financials were a mess—expenses were recorded in the wrong months, balance sheets were out of whack, and investors walked away.” In this episode, Daryl Ching , CFA and Managing Partne...

In this episode of The Unsure Entrepreneur Podcast , Roger Pierce talks with Leigh Mitchell—founder of Women in Biz Network and ChangeMaker Collective—about pushing through fear and insecurity to build a business with purpose. Leigh gets honest about self-doubt, imposter syndrome, and the quiet fears that creep in at 4 a.m. “Even when you think you’ve got it figured out, those feelings still show...

What does it really take to leave your 9-to-5 and build a successful business? Emily Baillie did it — but not by jumping in blindly. On this episode of The Unsure Entrepreneur Podcast , host Roger Pierce speaks with Emily, a digital marketing strategist, AI educator, and founder of Compass Content Marketing—recently nominated for a Canadian SME Small Business Award. With over 15 years of experienc...

Ever feel like the big players in your industry have the game rigged against you? Find out how one government agency is working hard to level the playing field during this talk with Majid Charania, Director of Compliance & Outreach at the Competition Bureau Canada .   From price fixing and bid rigging to deceptive marketing and monopolistic practices, Majid shares eye-opening insights on what’...

In this episode of The Unsure Entrepreneur Podcast , host Roger Pierce interviews Bruce Mayhew, founder of Bruce Mayhew Consulting, who shares his experiences in leadership development and communication training. He helps leaders and organizations to address challenges like time management, bridging generational gaps, and fostering respectful communication. With 20 years in business, Bruce knows a...

Canadian Entrepreneur Dave Sinkinson, co-founder of AppArmor, shares what it takes to build a successful business without outside funding. Starting with a simple idea for improving campus safety, Dave and his brother Chris turned their vision into a trusted solution used by institutions across North America. Their journey ended with a multi-million-dollar acquisition.  You’ll hear about the pitfal...