The Unsure Entrepreneur - podcast cover

The Unsure Entrepreneur

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.
Last refreshed:
Follow this podcast in the Metacast mobile app to refresh it and see new episodes.
Download Metacast podcast app
Podcasts are better in Metacast mobile app
Don't just listen to podcasts. Learn from them with transcripts, summaries, and chapters for every episode. Skim, search, and bookmark insights. Learn more

Episodes

Unhappy with Your Business? Reinvent It (w/Faith Seekings)

In this episode, longtime business owner Faith Seekings opens up about one of the most personal — and necessary — challenges in entrepreneurship: reinvention. She shares how she moved from building a full-service graphic design agency to becoming a solo content strategist focused on writing, storytelling, and strategic communication. Faith founded Rapport Communications Inc. and grew it into a thriving agency with 10 employees and even acquired another firm. But after years of success, something...

Aug 11, 202528 minSeason 1Ep. 30

What Entrepreneurs Should Know Before Starting a Podcast (w/Jamie Irvine)

Is podcasting worth your investment of time, money, and energy? One of the best people I know to answer that question is Jamie Irvine, National Sales Director at Parts for Trucks and seasoned podcast host. Jamie has produced over 150 episodes of the Build a Better Business podcast and 350 episodes of The Heavy Duty Parts Report, giving him rare insight into how podcasting can power business growth. Jamie shares how he turned podcasting into a career amplifier. What started as a solo side project...

Jul 28, 202542 minSeason 1Ep. 29

Venture for Canada Teaches You How to Buy a Business (w/Scott Stirrett)

What if the best way to start a business is to buy one that already exists? In this episode of The Unsure Entrepreneur Podcast , host Roger Pierce speaks with Scott Stirrett , Founder and CEO of Venture for Canada , a national charity helping young Canadians gain entrepreneurial experience and skills. Since 2013, Scott and his team have raised more than $80 million and supported over 10,000 early-career professionals through fellowships, internships, and real-world work placements in small busin...

Jun 24, 202528 minSeason 1Ep. 28

Accounting Truths That Could Save Your Business (w/Daryl Ching)

Most small business owners rely on a part-time bookkeeper and an accountant who shows up once a year. My guest explains why that setup leads to inaccurate financials and lost opportunities: “We lost deals because the financials were a mess—expenses were recorded in the wrong months, balance sheets were out of whack, and investors walked away.” In this episode, Daryl Ching , CFA and Managing Partner at Vistance Accounting , shares what every founder needs to hear about accounting, cash flow, and ...

May 21, 202538 minSeason 1Ep. 27

Overcoming Doubt and Building a Purpose-Driven Business (w/Leigh Mitchell)

In this episode of The Unsure Entrepreneur Podcast , Roger Pierce talks with Leigh Mitchell—founder of Women in Biz Network and ChangeMaker Collective—about pushing through fear and insecurity to build a business with purpose. Leigh gets honest about self-doubt, imposter syndrome, and the quiet fears that creep in at 4 a.m. “Even when you think you’ve got it figured out, those feelings still show up,” she admits. Her go-to strategies? Mindfulness, long-term thinking, and reminding herself that t...

Apr 23, 202528 minSeason 1Ep. 26

How to Build a Smarter Business with AI (w/Emily Baillie)

What does it really take to leave your 9-to-5 and build a successful business? Emily Baillie did it — but not by jumping in blindly. On this episode of The Unsure Entrepreneur Podcast , host Roger Pierce speaks with Emily, a digital marketing strategist, AI educator, and founder of Compass Content Marketing—recently nominated for a Canadian SME Small Business Award. With over 15 years of experience, Emily now trains entrepreneurs, marketers, and nonprofits across Canada to adapt and grow in the ...

Apr 03, 202533 minSeason 1Ep. 25

How the Competition Bureau Ensures Fair Play for Small Businesses (w/Majid Charania)

Ever feel like the big players in your industry have the game rigged against you? Find out how one government agency is working hard to level the playing field during this talk with Majid Charania, Director of Compliance & Outreach at the Competition Bureau Canada . From price fixing and bid rigging to deceptive marketing and monopolistic practices, Majid shares eye-opening insights on what’s legal, what’s not, and how entrepreneurs can protect themselves. “Our work is meant to foster a situ...

Mar 02, 202531 minSeason 1Ep. 24

Building a Consulting Business That Lasts (w/Bruce Mayhew)

In this episode of The Unsure Entrepreneur Podcast , host Roger Pierce interviews Bruce Mayhew, founder of Bruce Mayhew Consulting, who shares his experiences in leadership development and communication training. He helps leaders and organizations to address challenges like time management, bridging generational gaps, and fostering respectful communication. With 20 years in business, Bruce knows a thing or two about staying in the game. He discusses the popularity and misconceptions of starting ...

Jan 29, 202535 minSeason 1Ep. 23

Lessons from a Bootstrapped Startup Acquired for Millions (w/Dave Sinkinson)

Canadian Entrepreneur Dave Sinkinson, co-founder of AppArmor, shares what it takes to build a successful business without outside funding. Starting with a simple idea for improving campus safety, Dave and his brother Chris turned their vision into a trusted solution used by institutions across North America. Their journey ended with a multi-million-dollar acquisition. You’ll hear about the pitfalls of chasing rapid growth and the realities of bootstrapping, tech debt, and the long sales cycles o...

Jan 08, 202539 minSeason 1Ep. 22

How Carbon Accounting Helps Businesses Stay Competitive (w/Sanders Lazier)

Host Roger Pierce talks with Sanders Lazier, the founder and CEO of Carbonhound. Sanders leads a groundbreaking platform that empowers businesses to achieve low-carbon futures through accessible carbon accounting and climate intelligence tools. With a background in Fintech and sales, Sanders brings a unique perspective to addressing the growing challenges of climate change for mid-market businesses. Episode highlights include: Insights on how regulatory pressures like the EU's Carbon Border Adju...

Dec 03, 202433 minSeason 2Ep. 8

Entrepreneur Helps Solo Travelers See the World (w/Janice Waugh)

In this episode of The Unsure Entrepreneur , host Roger Pierce interviews Janice Waugh, Founder of Solo Traveler and Co-founder of the nonprofit organization Northstar Startups. Janice’s company Solo Traveler has transformed the solo travel industry by advocating for affordable travel experiences, partnering with companies that limit single supplements to 20% or less, and building a community of over 275,000 followers on Facebook. "Solo travel comes from a personal place for me," Janice explains...

Nov 15, 202432 minSeason 2Ep. 7

How to Buy Your Ideal Franchise Business (w/ Gary Prenevost)

In this episode of The Unsure Entrepreneur , Roger Pierce interviews Gary Prenevost, a Franchise Expert with over 30 years in the industry and author of the USA Today top-selling book, The Unstoppable Franchisee . As the President of FranNet Southern Ontario and Eastern Canada and a Board Member of the Canadian Franchise Association, Gary has guided thousands of entrepreneurs through the complexities of franchise ownership. If you’re exploring entrepreneurship, consider this: A key advantage of ...

Oct 22, 202436 minSeason 2Ep. 6

Bridging the Gap Between Banks & Small Businesses (w/Glen Senior)

In this episode of The Unsure Entrepreneur Podcast , Roger Pierce interviews Glen Senior, Founder and CEO of The Small Business Company, a specialized marketing agency providing expert small business content to banks, credit unions, and brands. Glen’s company partners with financial institutions across six countries to provide free, accessible educational content and tools for small business owners. These resources range from cash flow templates and business plan guides to webinars and financial...

Sep 30, 202437 minSeason 2Ep. 5

Your Legal Ally: Advice from the Entrepreneur-Friendly Lawyer (w/Albert Luk)

“Invest in your business's legal health now, and you’ll save yourself from costly headaches down the road,” says Albert Luk, J.D., in this value-packed episode of The Unsure Entrepreneur . Dubbed the “Entrepreneur-Friendly Lawyer,” Albert offers actionable strategies for business owners looking to mitigate risk while still fostering growth. In the episode, he explains that legal protection is crucial but shouldn’t hold entrepreneurs back from taking smart risks. As he puts it, “You can’t grow a ...

Sep 20, 202430 minSeason 2Ep. 4

The Rise of Immigrant Entrepreneurship in Canada (w/Sylvie Ratté & Mathieu Galliot)

In this episode of The Unsure Entrepreneur podcast, host Roger Pierce discusses immigrant entrepreneurship in Canada with two special guests from the Business Development Bank of Canada (BDC): Sylvie Ratté, Senior Economist, and Mathieu Galliot, Economist. Sylvie and Mathieu share their insights on the fascinating research appearing in their recent BDC article titled, "Immigrant entrepreneurship is taking centre stage in Canada." (See link below). In the podcast, you'll learn how immigrants are ...

Sep 04, 202429 minSeason 2Ep. 3

How Brock LINC is Shaping the Next Generation of Entrepreneurs (w/Cassie Conte)

In this episode of The Unsure Entrepreneur , host Roger Pierce chats with Cassie Conte, the Program Manager at Brock LINC, Brock University’s hub for innovation and entrepreneurship. What's clear in the interview is how valuable this resource is to aspiring entrepreneurs. Brock LINC is more than just a program—it’s a hub that nurtures innovation, creativity, and entrepreneurship. “We focus a lot on the early stage,” says Cassie. “Students come to us with great ideas, but they don’t always know w...

Aug 27, 202428 minSeason 2Ep. 2

Why Experiential Learning is Key to Entrepreneurial Success (w/Mathew Georghiou)

In this episode of The Unsure Entrepreneur Podcast , host Roger Pierce sits down with Mathew Georghiou, a dynamic entrepreneur, engineer, writer, and inventor, and founder of several companies including MediaSpark, GoVenture World, and KleverToys. Mathew shares his journey in revolutionizing business education through the creation of advanced educational games and simulations, such as the GoVenture Entrepreneur simulation. He discusses the importance of experiential learning in entrepreneurship,...

Aug 19, 202431 minSeason 2Ep. 1

Follow a GPS Plan to Reach Your Business Goals (w/Brian Moran)

In this episode of The Unsure Entrepreneur , host Roger Pierce interviews Brian Moran, a seasoned entrepreneur, small business expert, and host of The Small Business Edge Podcast. Brian talks about his transition from working in executive roles at prestigious publications such as The Wall Street Journal, Entrepreneur Magazine , and Inc. Magazine to founding his own companies, Brian Moran & Associates and Small Business Edge. The conversation delves into Brian's passion for supporting small b...

Aug 01, 202436 minSeason 1Ep. 13

Control Your Destiny by Learning How to Sell, Advises Small Business Coach (w/David Cohen)

In the latest episode of The Unsure Entrepreneur Podcast , host Roger Pierce sits down with David Cohen, a seasoned entrepreneur, small business coach, and the founder of YourBigVenture.com. A beacon of inspiration and wisdom for small business owners, David has dedicated his career to empowering entrepreneurs through coaching, teaching, and various educational programs. As the author of the motivational book Live Life Swift, David encourages readers to pursue their entrepreneurial dreams with c...

Jul 18, 202429 minSeason 1Ep. 12

YEDI Helps Entrepreneurs Turn Dreams Into Reality (w/Maria Konikov)

In this episode of The Unsure Entrepreneur Podcast, host Roger Pierce interviews Maria Konikov, the Director of Operations at the York Entrepreneurship Development Institute (YEDI). Maria discusses YEDI’s mission to support entrepreneurs through various programs, including their flagship incubator program and the one-year Entrepreneurship and Small Business Management Program. She highlights the importance of learning key business skills, having community support, and overcoming the fear of the ...

Jul 09, 202430 minSeason 1Ep. 11

Death or Public Speaking? Communication Coach Helps Entrepreneurs Conquer Their Fear (w/Bruce Hunt)

An astonishing 75% of people fear public speaking more than death. Thankfully, public speaking coach Bruce Hunt is here to talk us off that ledge in this episode of The Unsure Entrepreneur Podcast . Bruce shares his experience in helping individuals and organizations improve their communication skills. He has worked with major companies such as TD Bank, Xerox Canada, YMCA, George Brown College, and the Canadian Down Syndrome Society. Bruce also served as president of the prestigious Downtown Tor...

Jun 26, 202431 minSeason 1Ep. 10

Why Gen AI is the Answer to Canada’s Productivity Problem (w/Patrick Gill)

In this episode of The Unsure Entrepreneur podcast, host Roger Pierce sits down with Patrick Gill, Senior Director of Operations at the Business Data Lab at the Canadian Chamber of Commerce. The conversation dives deep into the productivity gap in Canada, the adoption and impact of generative AI (Gen AI) on small businesses, and the potential for AI to enhance productivity and competitiveness. Patrick highlights the urgent need for Canadian businesses to embrace AI, citing low productivity growt...

Jun 13, 202435 minSeason 1Ep. 9

Stand Out in Business by ‘Super Niching’ Advises Marketing Coach (w/Chala Dincoy)

Listen to this episode for expert strategies to win more customers. In this episode of The Unsure Entrepreneur , host Roger Pierce interviews Chala Dincoy, CEO and founder of The Repositioning Expert ( Repositioner.com ). Chala shares her journey from a successful corporate marketer at companies like Pepsi and Frito-Lay to becoming a sought-after marketing coach who helps B2B service providers reposition their marketing messages to better connect with decision-makers. Chala shares valuable insig...

Jun 04, 202437 minSeason 1Ep. 8

Surprise and Delight Your Customers, Advises Virtual Event Producer (w/Louis Trahan)

If you've ever been nervous about clicking the wrong button during a Zoom event, listen up. In this episode of The Unsure Entrepreneur Podcast , host Roger Pierce interviews Louis Trahan, the owner of Learngistics, a company specializing in corporate in-person and virtual learning experiences. Louis shares his journey from founding Last Minute Training to expanding into corporate learning and virtual events through his current company called Learngistics. He talks about the challenge of organizi...

May 23, 202432 minSeason 1Ep. 7

Work Until Your Clients Love It, Says Award Winning Designer (w/Rachel Ott)

In this episode of The Unsure Entrepreneur podcast, host Roger Pierce welcomes Rachel Ott, the dynamic force behind Varga Girl Design, a leading Canadian graphic design firm known for its innovative visual and technical design solutions. Rachel shares her diverse background from print to web design, and her journey to becoming one of the top designers recognized by Clutch.co. With a candid look into the challenges and triumphs of entrepreneurship, Rachel discusses the essence of her design philo...

May 15, 202429 minSeason 1Ep. 6

How to Quit Your Job to Start a Business Development Company (w/Nate Simpson)

In this insightful episode of The Unsure Entrepreneur Podcast , Nate Simpson, owner of Nate Simpson Business Development, joins host Roger Pierce to discuss his transition from a technical expert in fire protection to founding his own company. Nate delves into the nuances of business development within the architecture, engineering, and construction sectors, offering valuable advice for retaining clients and maximizing profitability. He shares personal stories of overcoming risk aversion and har...

May 08, 202432 minSeason 1Ep. 5

Releasing the Secrets of Video Production Success (w/Janine Harris)

This episode of The Unsure Entrepreneur Podcast with host Roger Pierce goes behind the scenes to look at the fascinating start-up journey of Janine Harris, founder of KeyRing Media. Janine shares her transition from a video production employee to the owner of a successful video production company that collaborates with giants like Toyota and BMW. Discover how Janine transformed her insight into a thriving business, the challenges she encountered, and her strategies for securing and retaining hig...

May 01, 202429 minSeason 1Ep. 4

The Pointman's Playbook for PR & Entrepreneurship (w/Patrick McCaully)

Join host Roger Pierce on The Unsure Entrepreneur Podcast as he engages with Patrick McCaully , founder of Pointman News Creation and a public relations virtuoso. In this revealing episode, Patrick shares his transformative journey from journalism to the founding of his PR firm, showcasing how a deep understanding of media can lead to groundbreaking campaigns. Discover the secrets behind creating newsworthy content, mastering the art of the pitch, and turning mundane information into compelling ...

Apr 23, 202433 minSeason 1Ep. 3

Organic Journey to Starting a Social Media Agency (w/Andrew Jenkins)

In this episode, host Roger Pierce interviews Andrew Jenkins , CEO of Volterra Digital who shares his amazing entrepreneurial journey from starting an e-commerce menswear business in 1995 to establishing a specialized social media and social selling firm. Andrew shares the lessons learned through failures, the evolution of his business into a retainer-based model offering outsourced social media management, and the importance of focused service offerings. In the podcast, he emphasizes the value ...

Apr 12, 202430 minSeason 1Ep. 2

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 an...

Apr 11, 20243 minSeason 1Ep. 1
Hosted on Transistor
For the best experience, listen in Metacast app for iOS or Android