The Unsure Entrepreneur

Hosted by Roger Pierce

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Aug 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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48 recent

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

April 28, 2026Episode 4225 min

Closing the Entrepreneurship Education Gap (w/Evan Carmichael)

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: schools aren't teaching enough about entrepreneurship. Two thirds of students say they want to become entrepreneurs, yet over 80% feel they learn nothing about it in school. Evan explains how his own path changed after discovering Junior Achievement, where he got his first real exposure to building a business. The conversation then shifts to how people learn about small business ownership. Instead of waiting on schools, both young people and midlife entrepreneurs are turning to content such as YouTube videos, social platforms, and online learning. As Evan says, “Whatever you don’t know how to do, go to YouTube… somebody awesome is sharing how they won.” The episode closes with clear advice for anyone considering entrepreneurship — whether you're 18 or 42. Start small. Act. “The fastest way… is to take the smallest first step and do it.” Resources for aspiring entrepreneurs: Watch Evan's YouTube video about schools and entrepreneurship Read Evan's books Visit EvanCarmichael.com Subscribe to Evan's YouTube Channel https://www.youtube.com/@EvanCarmichael See the video of this episode

April 15, 2026Episode 4132 min

Hard Truths and Tax Tips for New Entrepreneurs (w/Barbara Weltman)

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 has spent decades advising entrepreneurs and has been featured across major outlets including The New York Times, The Washington Post, CNBC, and Fox News. The discussion cuts straight to the fundamentals that determine whether a new business survives. “When people start their businesses, they’re very enthusiastic,” she says. “But what I help small business owners focus on are the unfun things… tax, financial and legal matters that if you don’t do it, your business is not going to survive.” You’ll hear hear advice on the mistakes that show up early — poor recordkeeping, mixing personal and business finances, and misunderstanding cash flow. Barbara also reinforces a point many entrepreneurs learn too late: “Taxes are the difference between what you earn and what you keep.” For aspiring entrepreneurs, this episode offers a clear message: much of business success depends on discipline, awareness, and getting the fundamentals right from day one. Big Ideas for Small Business https://bigideasforsmallbusiness.com Barbara Weltman on LinkedIn Barbara Weltman’s Books

March 24, 2026Episode 4037 min

Why Authentic Leadership Builds Strong Teams (w/Bruce Mayhew)

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 Leader , a book that focuses on empathy, self-awareness, and human connection as the foundation of effective leadership. During the conversation, Bruce challenges the traditional idea that leaders must have all the answers. Instead, he argues that authenticity and trust matter more than authority. “Authenticity doesn’t mean that I have to be perfect,” he explains. “It actually sometimes means I’m vulnerable. It means being able to say I don’t know.” According to Bruce, many business owners spend too much time proving their credentials instead of showing clients how they care about their needs. The discussion also explores how “human skills” — empathy, curiosity, communication, and emotional intelligence — give entrepreneurs a competitive advantage. Listen in for ways to build trust, improve emotional intelligence, and lead teams with confidence. BruceMayhewConsulting.com Find Bruce on LinkedIn Get his new book: The Path of an Inspired Leader

March 10, 2026Episode 3950 min

The Body Language Edge Every Entrepreneur Needs (w/Mark Bowden)

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 most popular shows on body language and human behavior with more than 1.1 million subscribers. Recognized globally for his work on nonverbal communication, Mark's clients include Zoom, Shopify, Toyota, KPMG, American Express, the U.S. Army, and NATO. In this conversation, Mark and Roger explore a critical truth for entrepreneurs: your business is judged through you before it is judged on your product. As Mark puts it, “The way your product and your service is initially going to get judged and continue to be judged is on your performance in front of people.” You’ll learn why first impressions are difficult to undo, the body language mistakes many founders make under pressure, and how entrepreneurs can project calm authority when the stakes are high. Mark and Roger also talk about making videos, books, credibility, and why communication may be the most powerful competitive advantage an entrepreneur can develop. Resources: Truthplane.com The Behavior Panel on YouTube Mark Bowden on LinkedIn