The Unsure Entrepreneur

Roger Pierce

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ENTREPRENEURSHIP
UPDATED WEEKLY

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.

4D AGO

How a Health Tech Startup Raised $5 Million (w/Emile Maamary)

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 over 75% of users and has helped more than 5,000 people regain independence. Getting there wasn't easy — it took five years and multiple iterations to reach market. "Whatever you think it's going to take to build, multiply that number by three,” emphasizes Emile. Listen to this podcast if you want to learn how to raise money for your business: Steadiwear has secured over $5 million in funding from angel investors, government incentives, and grants — including winning the $10,000 Zensurance Small Business Grant in 2025. Emile shares lessons about manufacturing, regulation, reimbursement hurdles, and raising capital. His core advice for aspiring entrepreneurs is direct: “Who's going to pay for this?” Resources:Zensurance Small Business Grant (*Apply by March 3, 2026 for the $10,000 grant*)Steadiwear.comEmile Maamary on LinkedInNew book! The Unsure Entrepreneur

29 min
JAN 30

Shrinking the Sales Prevention Department (w/Jamie Irvine)

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, tools, and technology that help heavy-duty parts manufacturers and distributors. In our conversation, Jamie explains why trucking is the backbone of the economy, noting that most grocery stores hold only three days of inventory and that if trucks stopped rolling, “within a few days people start dying.” That reality makes the industry an early warning system for broader economic trouble. He also shares why layoffs among drivers and mechanics signal deeper issues in Canada’s economy. The discussion then turns to what Jamie calls the “sales prevention department” — the internal friction that makes it harder for customers to buy. He argues every company has one, and the goal is to shrink it. From delayed follow-ups to confused roles, small breakdowns cost real money. Jamie offers clear advice on separating business development from account management, focusing on strengths, and designing sales teams that actually work. He also shares a practical closing technique that replaces pressure with silence and insight. As Jamie puts it, “The best pressure you can put on a buyer is silence.” The episode is packed with usable lessons for entrepreneurs at any stage. Resources:Check out Jamie's podcast The Heavy Duty Parts ReportVisit Jamie on LinkedInVisit Heavy Duty Parts Consulting Corporation

39 min
12/22/2025

Why So Many Canadians Want to Start a Business (w/Karen Svendsen)

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 Poll. The results are very exciting — with 59% of Canadians saying they want to start a business, and a whopping 81% believing business ownership is a viable way to earn a living. Ontario leads the country, with 68% showing entrepreneurial ambition, followed by Atlantic Canada and the Prairies. In the pod Karen talks about why independence, flexibility, and purpose now matter more than traditional career paths. "People want more control over their time and their long term prospects, and they want the ability to shape that future for themselves and for their family," says Karen. She also speaks candidly about blockers such as uncertainty, access to funding, lack of confidence, and not knowing where to begin. RBC wants to make it easier to get going. ”We think that a big part of our role is making the early stages feel less overwhelming. So we help people understand the practical steps to take, from registering their business to working through their business plan to securing or identifying sources of financing." Resources mentioned:RBC tools, resources, learning, & partnerships to start or grow a businessRBC 2025 Small Business Poll results

30 min
12/03/2025

Rieva Lesonsky on Trends, Fear, and the New Reality of Entrepreneurship

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 issues for The Huffington Post, Entrepreneur Magazine, and AllBusiness.com. She now runs her own site SmallBusinessCurrents.com, where she publishes data-driven insights about consumer behaviour, industry trends, business opportunities, and, of course, advice for entrepreneurs. Unsurprisingly, Rieva's impact has been recognized by the U.S. Small Business Administration and she's been inducted into the Business Journalists Hall of Fame. In our interview, Rieva explains why fear plays a useful role when you start a business. As she puts it, “Fear tells you what to look at… Fear is not there to stop you.” She discusses the rise of mid-career entrepreneurs, noting that “the typical age of startup is mid-40s to mid-50s.” She also identifies fast-growing opportunities in home improvement, beauty, ageing-in-place, niche consumer products, and male grooming — and shares fascinating stories of entrepreneurs who made it big. Amazing insights await! Enjoy this conversation with one of my professional heroes. Resources:SmallBusinessCurrents.comRieva Lesonsky on LinkedIn

41 min
11/13/2025

Building a Speak-Up Culture: Lessons in Leadership (w/Stephen Shedletzky)

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 are 92% more likely to stay and perform at their best. Through his company, Shed Inspires, he teaches that “we can’t ask people to perform at their best if we haven’t created an environment in which they feel it’s psychologically safe to do so.” From psychological safety to feedback and self-awareness, Stephen’s message is clear: leadership starts the day you hire your first team member. And his definition of leadership is simple but powerful. “Leadership is the attempt to leave the people and world around you better than when you found them.” Visit his website ShedInspires.com Buy his book Speak-Up Culture on Amazon

29 min
10/20/2025

How Accountants Can Work Less & Earn More (w/Ryan Lazanis)

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 practices that deliver profit and lifestyle. “It’s hard to scale advice,” Ryan says. “But if you standardize your offer and productize your services, you remove variables and free yourself from being the bottleneck.” On the subject of fees, a sensitive area for most accounting professionals, he shares why three-tier pricing works: “With one option, you’re nervous to raise prices. With three options, you can be aggressive—and most clients pick the middle.” Ryan also opens up about how AI is reshaping the profession, including his own experiment with cloning his voice and avatar to deliver a recent online presentation. While excited about AI’s potential, he’s cautious: “I think it’s actually going to make our lives more difficult, not easier, because expectations are so much higher now.” > Catch Ryan’s Accountex 2025 Keynote in Toronto on Nov 5, where he’ll reveal insights from the Top 50 Modern Accounting Firm Survey. > Attend Roger's session on How to Close More Sales for Your Accounting Practice also on Nov 5. Important links:FutureFirm.coAccountex Canada 2025 on Nov 4 & 5

32 min
09/30/2025

Comedy, Cash Flow, and YouTube Fame with Paul Chato

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 Green Show) helped him learn business basics, why recurring revenue beats “dragging an elephant back to the office,” and how asking for advice is the best sales pitch you’ll ever make. I've known Paul for years and wanted to hear his unique take on small business ownership. “An entrepreneur is someone who is absolutely certain of success and surprised when it happens,” Paul quips. We talk about Hackintoshes, YouTube tricks, and why it’s smart to keep your employees at arm’s length (hint: they’re not your friends). And here’s a gem revealed in the podcast — Paul tells us that he met his wife because of John Candy, the revered Canadian comic legend. This episode is part strategy, part stand-up. You’ve been warned. Resources mentioned:Call Me Chato on YouTubeCall Me Chato video about John CandyaPauling News on YouTubeYour Web DepartmentThe Frantics

45 min
09/12/2025

Why Entrepreneurs Must Master Communication (w/Ric Phillips)

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 them master verbal, vocal, and visual communication. With an MBA and a background in sociology and psychology, Ric combines academic insight with practical coaching experience. He also serves as Director of the York Entrepreneurship Development Institute (YEDI) and Executive Director of the National Communication Coaching Association of Canada. Ric explains his “3V” framework — verbal, vocal, and visual — as a tool to align words, tone, and body language for maximum impact. He stresses that confidence and competency fuel each other in a cycle: “The more competent you are at something, you get more confident, and the more confident you are, the more chances you take.” The conversation highlights the cost of poor communication: 68% of consumers have walked away from a business relationship because of it. Ric argues that entrepreneurs must pair technical details with emotional storytelling to connect with their audience. He also points out that nonverbal cues outweigh verbal ones “every single time,” making body language and delivery as critical as the content itself. Listeners will learn how to improve trust through comfort, why a pitch needs both emotional and technical balance, and why investing in communication skills pays off throughout your business journey. As Ric notes, “There’s no magic bullet… but there are tools available that give us structure.” Resources mentioned:NCCA3V CommunicationsYEDI

32 min

TRAILER

Intro / Know What You're Getting Into BEFORE You Commit to Starting a Business

Are you teetering on the edge of starting your own business but find yourself overwhelmed by the what-ifs? Dive into The Unsure Entrepreneur Podcast with your host, Roger Pierce to unravel the mysteries of entrepreneurship. This podcast is your compass in the world of self-employment, guiding you through the highs and lows of starting a small business. With over 30 years of entrepreneurial experience, Roger doesn't just share his journey; he opens the door to a myriad of small business owners and experts, offering insights that are as diverse as they are enlightening. What's in it for you? Learn from firsthand accounts from those who've been where you stand – at the precipice of decision.Glean wisdom from top small business experts.Find out if your business idea has legs, or if it's back to the drawing board.Uncover why some businesses thrive and others don't make the cut.From raising start-up capital to the nitty-gritty of business planning, we've got you covered.Starting a business might just be the most daunting venture of your life, but it's also potentially the most rewarding. Whether you're aiming for financial independence, seeking personal fulfillment, or both, The Unsure Entrepreneur Podcast is your first step towards making an informed decision. Author, columnist, and coach Roger Pierce has worked with thousands of entrepreneurs and weathered 14 small businesses of his own over the past 30 years. Join him weekly to explore if entrepreneurship is your calling, or if the stability of employment is where your heart lies. Subscribe now to enjoy what could be the turning point in your professional life. For more insights and to join our community, visit ⁠unsureentrepreneur.com⁠.

S1, E1

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3 min

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.

Creator

Roger Pierce
Years Active

2024 - 2026
Episodes

38
Rating

Clean
Copyright

© Roger Pierce
Show Website

The Unsure Entrepreneur