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.

2d ago

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. ResourcesStartup Canada Podcast https://www.startupcan.ca/learn/startup-canada-podcast/Canadian Entrepreneur Bloghttps://canentrepreneur.blogspot.com/Almost A Boss Newsletterhttps://www.unsureentrepreneur.com/subscribeShow CreditsHost & Producer: Roger Pierce | Artwork: Kaitlyn Pierce | Sound Engineering & Editing: Aleksandar Nikolic, FixTheAudio.com
Sep 14

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.” ResourcesLiva Foods website https://livafoods.com/ (check out the Dragons' Den clip)Read Lubaina's story in my new bookhttps://www.unsureentrepreneur.com/bookShow CreditsHost & Producer: Roger Pierce | Artwork: Kaitlyn Pierce | Sound Engineering & Editing: Aleksandar Nikolic, FixTheAudio.com
Aug 20

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. ResourcesHRCollab.ca The Resume Whisperer Podcast Almost A Boss Newsletterhttps://www.unsureentrepreneur.com/subscribeShow CreditsHost & Producer: Roger Pierce | Artwork: Kaitlyn Pierce | Sound Engineering & Editing: Aleksandar Nikolic, FixTheAudio.com
Jul 25

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 storehttps://chicncharmedjewelry.com/ Show CreditsHost & Producer: Roger Pierce | Artwork: Kaitlyn Pierce | Sound Engineering & Editing: Aleksandar Nikolic @ FixTheAudio.com
Jun 26

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. ResourcesSteve's website MrAllBiz.comhttps://www.mrallbiz.com/Steve's columns at Inc Magazinehttps://www.inc.com/author/steve-straussSteve's newsletter "Notes To An Entrepreneur" https://news.planetsmallbusiness.com/SCORE Mentorshttps://www.score.org/ Show CreditsHost and Producer: Roger Pierce | Artwork: Kaitlyn Pierce | Sound Engineering & Editing: Aleksandar Nikolic, FixTheAudio.com
Jun 9

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.comMarvin Garellek on LinkedIN
Jun 3

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

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. ResourcesRead The Unsure Entrepreneur bookVisit LeighMitchell.comListen to ChangeMaker Leader PodcastVisit RogerPierce.com

Trailer

Welcome to The Unsure Entrepreneur Podcast

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.

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

50
Rating

Clean
Copyright

© Roger Pierce
Show Website

The Unsure Entrepreneur