
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.
| Publishes | Twice monthly | Episodes | 48 | Founded | 2 years ago |
|---|---|---|---|---|---|
| Number of Listeners | Categories | EntrepreneurshipBusiness | |||

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... more
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. Wh... more
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 S... more
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... more
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 ... more
“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 Entr... more
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 s... more
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 2... more










Recent interactions between the hosts and their guests.
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The show centers on practical entrepreneurship for aspiring founders and current small-business owners, with a strong emphasis on taking action, funding options, and building sustainable ventures. Across episodes, listeners hear firsthand experiences from founders, mentors, and specialists—ranging from financing strategies and tax basics to leadership, sales engines, and go-to-market tactics. Guests span startups in health tech, software, services, and media, offering pragmatic guidance on cash flow, pricing, governance, and personal resilience. The format blends personal stories with actionable frameworks, making it likely helpful for anyone evaluating entrepreneurship, seeking mentorship, or planning a real-world path to launch and scale ... more
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The Unsure Entrepreneur launched 2 years ago and published 48 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.
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Recent guests on The Unsure Entrepreneur include:
1. Chanelle Chalazan
2. Steve Strauss
3. Marvin Garellek
4. Lisa Taylor
5. Roger Pierce
6. Evan Carmichael
7. Barbara Weltman
8. Bruce Mayhew
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