The Unsure Entrepreneur

Paul Chato has done it all — comedian, CBC exec, web entrepreneur, and YouTuber with 130,000 subscribers. In this episode of The Unsure Entrepreneur Podcast, Paul shares how he went from making Canadians laugh with The Frantics and cult hero Mr. Canoehead to building over 2,000 websites and pioneering a subscription model long before it was cool.

He even explains how doing Rick Green’s taxes (yes, that guy from The Red Green Show) helped him learn business basics, why recurring revenue beats “dragging an elephant back to the office,” and how asking for advice is the best sales pitch you’ll e...

Whether you’re pitching investors, leading a team, or serving customers, this episode will show you how to strengthen your most valuable entrepreneurial skill: communication.

Host Roger Pierce talks with Ric Phillips, Founder of 3V Communications, to explore why developing communication skills is make-or-break factor for new and existing entrepreneurs.

Ric has been coaching entrepreneurs and professionals since 2006, helping them master verbal, vocal, and visual communication. With an MBA and a background in sociology and psychology, Ric combines academic insight with practical coaching experience. He also serves as Director of the York Entrepreneurship Development Institute (YE...

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 shifted. “I wasn’t happy anymore,” she says. That realization sparked a bold decision to dismantle what she had built and return to working on her own te...

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 with a poor webcam and free editing tools became a strategic marketing channel that...

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 businesses across the country.

Scott is also the author of the upcoming book The Uncertainty Advantage, a guide for early-career professionals on...

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 the real cost of ignoring your books. 

With ten years on Bay Street and ano...

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 the goal is to serve others—not to be perfect.

Leigh shares how a volunteer trip planted the...

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 digital world.

Emily shares how she built her business while holding onto her full-time job, working nigh...

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 situation where small and medium-sized businesses have an equitable opportunity to compete,” he explains.

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 a consulting business and emphasizes that while entry into the field is fairly easy, achieving lasting success requires perseverance, adaptability, and delivering exceptional value.

"Staying...

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 of enterprise clients. In the podcast, Dave explains why market validation matters more than raising capital. "Your first customer is a b...

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:

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, reflecting on how a life transition inspired her business.

Janice also shares insights into the financial aspects of running a con...

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 franchising is the lower failure rate compared to traditional startups — under 20%, versus 50% for businesses started from scratch. 

"Franchis...

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 calculators — all with the aim of helping businesses start, grow, and thrive. Content from The Small Business Company reaches millions of entrepreneurs globally.

In...

“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 business by saying 'no' to everything. Success often comes when you balance risk with reward — sometimes the biggest gains happen when...

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 transforming the entrepreneurial landscape. For example, with 34% of all Canadian entrepreneurs being immigrants — a rate higher than other developed countries — immigrants are driving innov...

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 what to do next. We help them figure that out.”

Cassie shares...

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, the value of embracing failure, and how his products are helping both students and professionals develop essential business skills. Mathew also offers practical advice for aspiring entrepreneurs, emphasizing the importance of...

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 business owners, his insights on foundational business planning, and the significance of having a GPS plan over a rigid business plan.

"Imagine having...

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 clarity and vigor.

During the conversation, David emphasizes the importance of selling skills and relationship building in entrepreneurship. "If you learn how to sell...

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 unknown in entrepreneurship. Maria shares inspiring stories of entrepreneurs who have successfully navigated their business journeys with YEDI's help, emphasizing the value of mentorship and continuous learning. While many en...

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 Toronto Toastmasters Club, where he developed his passion for guiding people to public speaking breakthroughs.

Throughout the interview, Bruce...

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 growth and the opportunities AI presents to streamline operations, automate tasks, and ultimately improve the standard of living in...

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 insights into the concept of ‘super niching,’ where she advises businesses to narrow their focus to a specific niche market...

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 organizing virtual events, how nervous people can be online, and the kinds of supports his company provides, including technical checks, e...

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 philosophy, which is deeply rooted in client satisfaction and tailored services.

Rachel provides invaluable advice fo...

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 harnessing his technical background to create unique business opportunities, providing listeners with actionable tips for turning entrepreneurial aspirations into successful ventures.

[Visit Nate Simpson Business...

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 high-profile clients.

Whether you're a new business owner or dreaming of starting one, Janine offers practical advice on the...

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. 

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 of predictable revenue, work-life balance, and the autonomy entrepreneurship provides.

Listeners will gain insights into the challenges and rewards of entrepreneurship, the significance of t...

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...