The Unsure Entrepreneur

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 content-based business, with income from direct sales advertising and other revenue streams like courses and programmatic ads. Her advice for aspiring entrepreneurs highlights the value of focusing on a niche market, listening to customers, and building resilience. "Listening to customers is key," she says, explaining how her readers' feedback on single supplements shaped her business model.  She also discusses her work with Northstar Startups, which provides mentorship, resources, and a supportive community for people with barriers to traditional employment, including those in Toronto's underserved communities. Tune in for an inspiring conversation filled with practical advice on building a meaningful business that aligns with personal passions — whether it’s advocating for affordable solo travel or creating opportunities for self-employment through community support. Resources:Solo Traveler websiteJanice Waugh on LinkedInNorthstar Startups website

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.  "Franchising isn't just about buying a business; it's a time-compression strategy," Gary says. He describes the model as a guided path where franchisees benefit from established systems, coaching, and a community of other franchisees. Gary explains the depth and scope of franchising in Canada, where franchises account for approximately 45% of all retail sales. While food and retail franchises are most visible, he emphasizes that the industry spans over 60 sectors, including services like groundskeeping and tutoring.  Don’t want to invest a fortune? As Gary explains, there are franchises for all budgets ranging from small service-based franchises costing under $50,000 to large brick-and-mortar franchises that can exceed millions. And, with the Canada Small Business Financing Program, entrepreneurs can secure up to $500,000 in funding with a government guarantee.  This episode is packed with valuable insights for anyone considering franchising as a viable path to business ownership.ResourcesGaryPrenevost.comYourE2EJourney.comThe Unstoppable Franchisee book on AmazonLinkedIn Profile

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 the conversation, Glen dives into how his background in education and entrepreneurship shaped the mission of The Small Business Company, and how the evolving relationship between banks and small businesses can improve financial health and business success globally. "Banks have an incredible opportunity to support small businesses not just by offering loans, but by providing practical, educational resources that empower owners to make smarter financial decisions," he says in the podcast.Key takeaways include Glen's suggestions for creating content that helps banks engage meaningfully with small business customers and his thoughts on the future challenges for entrepreneurs. Links:The Small Business CompanyGlen Senior on LinkedInEmail glen@tsbc.com

“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 you're willing to step outside your comfort zone."With over 20 years of legal experience across diverse industries such as video gaming, private equity, digital advertising, and customer loyalty, Albert currently serves as General Counsel and Chief Privacy Officer at Bond Brand Loyalty. He manages legal compliance, privacy, and risk management for the global customer engagement agency.Throughout the podcast, Albert shares his unique perspective on aligning legal strategies with business growth, drawn from his work with both emerging startups and established enterprises. He also covers key topics such as choosing the right business structure, drafting solid contracts, and making smart decisions about client selection.Links:Albert Luk on LinkedIn

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 innovation, job creation, and economic growth.  The economic impact of immigrant entrepreneurs is significant, as Sylvie points out in the episode: "New entrepreneurs from other countries are responsible for 25% of net job creation in Canada, compared to 17% for businesses in the private sector." The conversation highlights the challenges newcomers face, including access to financing, building credit history, and navigating cultural and regulatory differences. Tune in to discover how immigrants are shaping the future of business in Canada and explore the valuable resources available to support them, including BDC's initiatives for newcomer entrepreneurs.Links from the podcast:BDC Article Immigrant entrepreneurship is taking centre stage in CanadaBDC Resources & Loans for Newcomer EntrepreneursBDC Entrepreneur Toolkit BDC Business Assessments & QuizzesSylvie Ratté on LinkedInMathieu Galliot on LinkedInFollow @bdc_caArticle on UnsureEntrepreneur site

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 her insights on the supports Brock LINC offers to help early-stage entrepreneurs validate their ideas, develop their skills, and build viable businesses. For future business owners, she talks about the importance of customer discovery, mentorship, and having an entrepreneurial mindset. Cassie also highlights Brock LINC’s fascinating success stories—such as a virtual reality company training firefighters, and a safety wear company for workers at heights.Visit Brock LINCCassie Conte on LinkedIN

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 side hustles, financial literacy, and leveraging tools like simulations to prepare for real-world business challenges."Entrepreneurs solve problems, drive innovation, take risks, and create jobs. It's not just about wealth; it's about distributing that wealth to many, not just a few," says Mathew in the podcast.Resources:Georghiou.comMatthew Georghiou on LinkedIn

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 a GPS plan for your business," he says in the podcast. "When you encounter a traffic jam, you don't just sit there — you find an alternate route. The same applies to business. A GPS plan allows you to pivot and adapt, ensuring you're always moving toward your destination."Brian also discusses the challenges faced by small business owners, the critical role of discipline, commitment, and accountability in achieving success, and the abundance of resources available for entrepreneurs. One of those resources is his popular podcast for business owners called The Small Business Edge, where Brian extracts business insights and lessons from entrepreneurs, executives, and experts. Brian wraps up the episode with advice for starting and sustaining a business, the need for thorough preparation, and the importance of surrounding yourself with advisors to hold you accountable to your goals. Links:Check out my recent interview on The Small Business Edge PodcastSmall Business Edge Content ZoneBrian Moran on LinkedInBrian Moran on X/Twitter

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, you'll never work for somebody else again," he asserts, highlighting how mastering sales can ensure control over one's destiny. He shares practical tips on how to build relationships, communicate effectively, and offer value to potential clients.David also offers advice on securing funding and mentorship. He recommends tapping into local resources, such as economic development offices, banks, and organizations like Futurpreneur and the Business Development Bank of Canada.Resources:YourBigVenture websiteDavid Cohen LinkedIn Profile“26 Minutes With” Podcast

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 entrepreneurs are anxious to jump in without first investing in skills training, Maria believes “Having a strong educational foundation gives you the confidence to move forward."ResourcesYEDI websiteMaria Konikov on LinkedIn

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 discusses the importance of confidence, preparation, and practice in public speaking. He redefines public speaking as any situation where you have an audience, emphasizing that effective communication is crucial for entrepreneurs. As Bruce puts it, “You have to start where you're at and just keep working at it.”Join us as Bruce offers valuable tips for overcoming the fear of public speaking and shares inspiring stories from his workshops and coaching sessions. Whether you're pitching to investors, presenting to clients, or simply looking to improve your everyday communication skills, this episode is packed with insights to help you succeed.Resources: BruceHunt.caLinkedIn Profile

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 Canada. Patrick discusses the findings from his recent report, Prompting Productivity: Generative AI Adoption by Canadian Businesses which reveals that while interest in AI is high, actual adoption is still limited among Canadian businesses, especially small businesses. He emphasizes that AI can significantly augment workers' capabilities rather than replace them, providing practical examples of how AI can improve daily business tasks such as content creation, customer service, and data analysis. Patrick also underscores the importance of government support in upskilling the workforce and fostering a culture of innovation among Canadian businesses. Key Takeaways:Canada faces a critical productivity gap, with growth rates lagging other G7 countries. AI adoption is essential to reversing this trend.Gen AI can automate low-value tasks, allowing workers to focus on higher-value activities, enhancing overall productivity.Only 38% of Canadians view AI positively, making them more nervous about AI compared to other countries.Small businesses, which constitute 98% of Canadian businesses, can leverage AI for tasks like content creation, customer service improvement, and data analysis.Government initiatives to upskill the workforce and support digital adoption are crucial for widespread AI implementation and improving public trust in AI technologies.Enjoy this insightful conversation on a subject that’s very important to all Canadians. Click to download the report ‘Prompting Productivity’Read the media release from the Canadian Chamber of CommerceConnect with Patrick Gill on LinkedInRead the blog article on UnsureEntrepreneur.com

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 to differentiate themselves from competitors. She emphasizes that this approach not only makes the messaging more targeted and effective but also positions the business as an expert in solving specific problems. Chala says, "When you're super niched, your messaging conveys that you're an expert in their pain and that you serve nobody else but them.”​ Chala also discusses her ‘abundance mindset’ and encourages other entrepreneurs to believe in their value and charge accordingly. She explains that many new business owners underprice their services due to a ‘scarcity mindset,’ but shifting to an abundance mindset can transform their business success. "It's not about diplomas or certifications — it's all mindset. If you believe in your worth, others will too," she advises​​. Website: Repositioner.comLinkedIn: https://www.linkedin.com/in/chaladincoy/ Twitter: @Chala_Dincoy

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, event production — and arranging guest speakers and content, if requested. Along the way he shares his thoughts on delighting customers and maintaining high service standards.He also discusses the urgency of AI readiness for businesses, explaining how AI can transform operations for both small and large enterprises. Louis emphasizes the nimbleness of small businesses in adopting AI, saying, "AI adoption can be a lot easier and quicker than for large enterprises." When asked about his advice for aspiring entrepreneurs, Louis recommends doing thorough market research and asking the "right questions" to potential customers before launching a business.  Tune in to hear more about Louis' entrepreneurial path and insights on staying agile and client-focused in the business world.Visit LearngisticsLinkedIn Profile

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 for aspiring entrepreneurs, emphasizing the importance of adapting to client needs, the impact of receiving honest client feedback via platforms like Clutch, and how such interactions fuel her business’s success. She offers a wealth of knowledge for anyone interested in the intersections of creativity, client management, and entrepreneurship. Visit VargaGirlDesign.com

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 Development]

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 importance of networking, adapting new business models, and maintaining relationships. (Visit KeyRing Media)

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 stories that grab media attention. Patrick also offers invaluable advice for new entrepreneurs, from navigating the shift from traditional employment to entrepreneurship, to innovative strategies for media engagement. Learn how to use humor and creativity to make your mark in the business world. Whether you're in the early stages of your venture or looking to inject new life into your PR efforts, this episode provides essential insights into making impactful connections through media. Tune in to gain practical tips and inspiration from a seasoned expert who knows how to make the media work for you.Website for Pointman News Creation: https://pointmannc.com/Email Patrick McCaully: patrick@pointmannc.com

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 testing ideas, and strategies for building a successful business with a stable income stream.Check out Volterra Digital.Subscribe now to catch future episodes.Be sure to visit UnsureEntrepreneur.com.

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.