The Unsure Entrepreneur

Hosted by Roger Pierce

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Oct 2026

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About the show

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.

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52 recent

November 11, 2026Episode 5233 min

Is Your Business Taking a Toll on Your Health? (w/Martha Trahan)

What happens to your meals, movement, and health when your business takes up your day? In this episode of The Unsure Entrepreneur , host Roger Pierce talks with Martha Trahan, founder of She Nutrition, about building a business while looking after yourself. Based in Toronto, Martha exclusively coaches women over 40. She holds certifications as a Nutritional Practitioner, Menopause Coaching Specialist, and Canfitpro Personal Training Specialist. Her work includes coaching, the Midlife Warriors Club, and workshops for organizations. Martha opens up about what her training didn’t prepare her for, including marketing, administration, and selling a service that requires clients to change their habits. Very active on social media, you’ll hear how an Instagram post brought in a client from Alabama, why she sets aside time to record content, and how accountability supports her clients. Because it's so challenging to properly fuel busy entrepreneurs, Martha suggests keeping easy ingredients on hand, assembling meals, and planning what to eat before hunger interrupts work. “It's a matter of having a plan that will adapt to wherever you are in life,” she says. Shenutrition.ca https://shenutrition.ca/ Facebook/Insta @shenutrition.ca LinkedIn https://www.linkedin.com/in/martha-trahan/ Show Credits Host & Producer: Roger Pierce | Artwork: Kaitlyn Pierce | Sound Engineering & Editing: Aleksandar Nikolic, FixTheAudio.com

October 28, 2026Episode 5134 min

Can You Learn to Be an Entrepreneur? (w/Susan Kates)

Before you start a business, how can you find out whether entrepreneurship suits you? In this episode of The Unsure Entrepreneur Podcast , Roger Pierce speaks with Susan Kates, a professor at Humber Polytechnic, entrepreneur, and faculty advisor to Enactus Humber. Susan teaches entrepreneurship, has coordinated Humber’s Entrepreneurial Enterprise Business Management Program, and earned a Masters degree in innovation and entrepreneurship. In 2026, she received the Ontario Centre of Innovation’s inaugural Educator Innovation and Entrepreneurship Award. “One of the biggest mistakes that entrepreneurs tend to have is that they don't do their research,” she says. That research can start with a customer conversation or taking a booth at a farmers market. For example, Susan shares how three founders tested snack boxes with customers and how Humber students applied innovation to turn discarded cosmetics into paint. She also explains why spending time alongside a business owner can teach you things a classroom cannot. Listen to this podcast to learn how to test demand, ask questions about ownership, and develop entrepreneurial thinking. Resources Email Susan Kates: susan.kates@humber.ca LinkedIn page Humber College website Show Credits Host & Producer: Roger Pierce | Artwork: Kaitlyn Pierce | Sound Engineering & Editing: Aleksandar Nikolic, FixTheAudio.com

October 1, 2026Episode 5043 min

Entrepreneurship Is a Team Sport, Says Rick Spence

Starting a business means making decisions you’ve never faced. Who will help you make them? The Unsure Entrepreneur Podcast celebrates its 50th Episode with Rick Spence joining Roger Pierce to talk about why mentors, advisors, and learning belong in your plans before you launch. They also explore why Canada needs more entrepreneurs to serve customers, create opportunities, and help other businesses grow. “I say entrepreneurship is a team sport,” says Rick, who has spent 35 years working with entrepreneurs as a journalist, author, former editor and publisher of PROFIT Magazine , and now host of the Startup Canada Podcast. His advice begins with reaching out to people who know your industry. “My favourite entrepreneurs are the ones who build an advisory board before they even start.” That group can include people who understand finances, hiring, and the market you want to enter. Rick says new entrepreneurs don’t need meetings or paperwork — you need people who will answer when you call. He explains how to build those relationships, learn from customer feedback, and test your idea while keeping your day job. For unsure entrepreneurs, Rick also challenges you to ask for help before spending months developing something customers don’t want. “Entrepreneurship is a do-it-yourself thing, but you don't have to do it by yourself.” If you’re weighing business ownership, this conversation gives you a starting point: talk to people, ask questions, and use what you learn to decide your next move. Resources Startup Canada Podcast https://www.startupcan.ca/learn/startup-canada-podcast/ Canadian Entrepreneur Blog https://canentrepreneur.blogspot.com/ Almost A Boss Newsletter https://www.unsureentrepreneur.com/subscribe Show Credits Host & Producer: Roger Pierce | Artwork: Kaitlyn Pierce | Sound Engineering & Editing: Aleksandar Nikolic, FixTheAudio.com

September 14, 2026Episode 4933 min

Entrepreneur Delivers a Better Way to Sweeten Food (w/Lubaina Rakla)

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 back. She got the product into Sobeys and Loblaws in the company's very first year. Today, its products are sold through retailers including Metro, Whole Foods, Bulk Barn, Amazon, and Walmart.ca. Lubaina also talks about her 2023 appearance on the hit TV show Dragons’ Den . She accepted an offer from investor Wes Hall on the show, then chose not to give up 33% of her company. However, the advice she received on the show did change Liva Foods, when Dragons' Den Star Arlene Dickinson urged her to treat the company as an ingredient brand. Lubaina acted on that advice, and now Liva’s wholesale food-service business has surpassed retail. The conversation covers startup costs, margins, supply problems, negotiation, and the loneliness of entrepreneurship. Lubaina also explains why purpose and passion matters when a business gets hard. “There’s no overnight success,” she says. “It’s just a journey.” Resources Liva Foods website https://livafoods.com/ (check out the Dragons' Den clip) Read Lubaina's story in my new book https://www.unsureentrepreneur.com/book Show Credits Host & Producer: Roger Pierce | Artwork: Kaitlyn Pierce | Sound Engineering & Editing: Aleksandar Nikolic, FixTheAudio.com

August 20, 2026Episode 4834 min

What Every Founder Needs to Know Before Hiring (w/Sharilyn Vandermolen)

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 Resources Leader, Certified Diversity and Inclusion Professional, and workplace investigator with 15+ years of experience. She has hired over 1,000 employees, reviewed 100,000+ resumés, and advised teams across Canada, the U.S., and Latin America. She also hosts The Resume Whisperer Podcast. They discuss when to bring in HR support, how to define roles, why hiring based on “liking” candidates is risky, contractor misclassification, and how small businesses on a budget can compete for talent. Like many small business owners, it's easy to wait until the last minute to hire. “Desperation leads to bad hires,” warns Sharilyn in the podcast, instead recommending clear success criteria, consistent interview questions, and hiring for complementary skills. Resources HRCollab.ca The Resume Whisperer Podcast Almost A Boss Newsletter https://www.unsureentrepreneur.com/subscribe Show Credits Host & Producer: Roger Pierce | Artwork: Kaitlyn Pierce | Sound Engineering & Editing: Aleksandar Nikolic, FixTheAudio.com

July 25, 2026Episode 4731 min

What a Teen Founder Can Teach You About Starting Up (w/Chanelle Chalazan)

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 Entrepreneur Podcast how her father’s construction business and her mother’s love of jewelry helped shape the idea. She explains how the company keeps prices down by avoiding retail stores and overhead costs. She discusses balancing business with high school, where she earns grades in the high 90s, and her plans to study business before pursuing medicine. She also shares some surprising insights on what rejection, risk, customer service, and time management have taught her at a very young age. “You learn so much from just doing things in person,” she says. Check out Chanelle's very inspiring start-up story. Visit her store https://chicncharmedjewelry.com/ Show Credits Host & Producer: Roger Pierce | Artwork: Kaitlyn Pierce | Sound Engineering & Editing: Aleksandar Nikolic @ FixTheAudio.com

June 26, 2026Episode 4648 min

Steve Strauss on Why America Needs More Small Business Owners

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 SCORE Mentors as the country’s leading champion of small business. In our conversation, Steve makes a strong case for why America needs more entrepreneurs. The U.S. has more than 36 million small businesses. They represent 99% of all American businesses and employ about 62 million people. But those numbers only tell part of the story because small businesses are at the heart of our communities. Small businesses are the ones you see in your own neighborhood; the local pub, the busy hair salon on the corner, the tradesperson shingling a new roof, and your favorite coffee shop where the owner knows you take one sugar. Steve sees entrepreneurs as builders. They create work. They serve customers. They support families. They bring ideas into the world. They give people hope. “What I love about entrepreneurs, what I love about small business, is it’s positive,” he says. If you feel the pull of entrepreneurship, listen to our conversation for a clearer, more encouraging look at what it takes to begin. Resources Steve's website MrAllBiz.com https://www.mrallbiz.com/ Steve's columns at Inc Magazine https://www.inc.com/author/steve-strauss Steve's newsletter "Notes To An Entrepreneur" https://news.planetsmallbusiness.com/ SCORE Mentors https://www.score.org/ Show Credits Host and Producer: Roger Pierce | Artwork: Kaitlyn Pierce | Sound Engineering & Editing: Aleksandar Nikolic, FixTheAudio.com

June 9, 2026Episode 4546 min

The Funding Mistakes Most Entrepreneurs Don't See Coming (w/Marvin Garellek)

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 practical insights on business plans, cash flow management, credit scores, government funding programs, alternative lenders, and the importance of surrounding yourself with experienced professionals. Throughout the conversation, Marvin challenges common misconceptions about money and entrepreneurship while offering actionable advice for both startup founders and established business owners. As he explains, “Without a plan you can’t get to where you’re going,” and reminds entrepreneurs that financing success starts long before you apply for a loan. Whether you're launching your first business or looking to grow an existing one, this episode provides a realistic roadmap for understanding and managing the financial side of entrepreneurship. MontrealFinanceGuy.com Marvin Garellek on LinkedIN

June 3, 2026Episode 4436 min

What Entrepreneurs Get Wrong About Growth (w/Lisa Taylor)

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. The conversation explores career development for entrepreneurs, the importance of building a business that aligns with your personal growth, and why nonlinear career paths are becoming the norm rather than the exception. Lisa also shares insights from leading a certified B Corporation and discusses how entrepreneurs can think bigger about growth, impact, and opportunity. As she puts it, “Most entrepreneurs don't realize that you actually can build a business that you resent.” Whether you're launching your first venture or scaling an established business, this episode offers wisdom on building a company and a career that grows with you. Resources: https://challengefactory.ca/ The Talent Revolution - Book Lisa on LinkedIn

May 19, 2026Episode 4325 min

Roger Pierce and Leigh Mitchell discuss risk, freedom, and The Unsure Entrepreneur book

“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. Roger is an entrepreneur, content producer, educator, and small business expert who has launched 14 businesses over a 30-year career. He has worked with thousands of entrepreneurs through training programs, seminars, and partnerships with banks and major organizations. Roger talks about the emotional side of business ownership, which he believes is too often ignored. “The emotional risk part of running a business, I think, is often under discussed and underestimated.” He shares why stress, fear, financial pressure, and responsibility can take a toll. The episode also explores the upside: freedom, flexibility, control, and the ability to build work around your life. As Roger says, “Being able to weave in your family life to your small business life, that is a true benefit.” If you're curious about starting a business, listen to this episode to help assess whether or not it's the right path for you. Resources Read The Unsure Entrepreneur book Visit LeighMitchell.com Listen to ChangeMaker Leader Podcast Visit RogerPierce.com