The Unsure Entrepreneur

Roger Pierce
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  • Entrepreneurship
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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.

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

    3d ago

    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

    37 min
  2. Roger Pierce and Leigh Mitchell discuss risk, freedom, and The Unsure Entrepreneur book

    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

    25 min
  3. Closing the Entrepreneurship Education Gap (w/Evan Carmichael)

    Apr 28

    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 entrepreneurshipRead Evan's booksVisit EvanCarmichael.comSubscribe to Evan's YouTube Channel https://www.youtube.com/@EvanCarmichaelSee the video of this episode

    26 min
  4. Hard Truths and Tax Tips for New Entrepreneurs (w/Barbara Weltman)

    Apr 15

    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

    32 min
  5. Why Authentic Leadership Builds Strong Teams (w/Bruce Mayhew)

    Mar 24

    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.comFind Bruce on LinkedInGet his new book: The Path of an Inspired Leader

    38 min
  6. The Body Language Edge Every Entrepreneur Needs (w/Mark Bowden)

    Mar 10

    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.comThe Behavior Panel on YouTubeMark Bowden on LinkedIn

    51 min
  7. How a Health Tech Startup Raised $5 Million (w/Emile Maamary)

    Feb 13

    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
  8. Shrinking the Sales Prevention Department (w/Jamie Irvine)

    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
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About

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.

Information

  • Creator
    Roger Pierce
  • Years Active
    2024 - 2026
  • Episodes
    44
  • Rating
    Clean
  • Copyright
    © Roger Pierce
  • Show Website
    The Unsure Entrepreneur