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The Unsure Entrepreneur

Roger Pierce
Entrepreneurship
Leadership
Royal Bank Of Canada
Entrepreneurship Education
Chic & Charmed Boutique By Chanel
Heavy Duty Consulting Corporation
Sales
The Path Of an Inspired Leader
Taxes
3V Communications
Speak-Up Culture
Psychological Safety
Jamie Irvine
Steadiwear
Authenticity
Human Skills
Small Business
The Unsure Entrepreneur
Challenge Factory
Non-Linear Careers

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.

PublishesTwice monthlyEpisodes48Founded2 years ago
Number of ListenersCategories
EntrepreneurshipBusiness

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Artwork for The Unsure Entrepreneur

Latest Episodes

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

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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

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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

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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

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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

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“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

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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

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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

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Recent Guests

Chanelle Chalazan
Young founder of Chic & Charmed Boutique by Chanel
Chic & Charmed Boutique by Chanel
Episode: What a Teen Founder Can Teach You About Starting Up (w/Chanelle Chalazan)
Steve Strauss
Author, attorney, entrepreneur, content creator
The Strauss Group / mrallbiz.com / planetsmallbiz.com
Episode: Steve Strauss on Why America Needs More Small Business Owners
Marvin Garellek
Montreal Finance Guy, advisor to small business owners on funding and financing
Montreal Finance Guy
Episode: The Funding Mistakes Most Entrepreneurs Don't See Coming (w/Marvin Garellek)
Lisa Taylor
Founder and CEO of Challenge Factory
Challenge Factory
Episode: What Entrepreneurs Get Wrong About Growth (w/Lisa Taylor)
Roger Pierce
Entrepreneur, content producer, educator; author of The Unsure Entrepreneur
Episode: Roger Pierce and Leigh Mitchell discuss risk, freedom, and The Unsure Entrepreneur book
Evan Carmichael
Entrepreneur, author, and prolific content creator known for entrepreneurship education
Self-employed / Entrepreneur
Episode: Closing the Entrepreneurship Education Gap (w/Evan Carmichael)
Barbara Weltman
Attorney and founder of Big Ideas for Small Business
Big Ideas for Small Business
Episode: Hard Truths and Tax Tips for New Entrepreneurs (w/Barbara Weltman)
Bruce Mayhew
Founder of Bruce Mayhew Consulting; author of The Path of an Inspired Leader
Bruce Mayhew Consulting
Episode: Why Authentic Leadership Builds Strong Teams (w/Bruce Mayhew)
Mark Bowden
Global body language expert and author, founder of Truthplane
Truthplane, Gestureplane
Episode: The Body Language Edge Every Entrepreneur Needs (w/Mark Bowden)

Host

Roger Pierce
Host of The Unsure Entrepreneur

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Talking Points

Recent interactions between the hosts and their guests.

What a Teen Founder Can Teach You About Starting Up (w/Chanelle Chalazan)
Q: What advice would you give to another young person who has an idea but is unsure about starting?
Turn any no or maybe into yes, be willing to take risks, and understand that failure and rejection are part of learning—pushing through builds momentum and can lead to real opportunities.
Unhappy with Your Business? Reinvent It (w/Faith Seekings)
Q: How do you know when it's time to evolve your business versus doubling down on what's already working?
She emphasizes listening to personal happiness and market signals, noting that doubling down might mean shedding in-house capabilities that no longer fit, while evolving should balance passion with revenue and client needs.
What Entrepreneurs Should Know Before Starting a Podcast (w/Jamie Irvine)
Q: How should a new podcaster approach niching and building a sustainable show?
Start with a narrow focus where you have deep expertise, test by running concurrent shows, then double down on the most promising niche; continually bring in diverse guests to enrich the same core topics, because the host's consistency and relationship with the audience drive long-term success.
What Entrepreneurs Should Know Before Starting a Podcast (w/Jamie Irvine)
Q: What advice would you give someone thinking about getting into podcasting easily?
Buy a microphone and start recording with people, keep content focused on your ideal audience, and follow a simple formula: identify the hero (the customer), outline the problem (the villain), position yourself as the guide, present solutions, add proof, and finish with a clear call to action.
Why Entrepreneurs Must Master Communication (w/Ric Phillips)
Q: What makes a pitch stand out to an investor or potential client?
The pitch stands out when the business, team, and story resonate with the audience; it's about whether the audience sees themselves in the opportunity and whether the messaging matches their interests, not just whether the entrepreneur likes the idea.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
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Professions
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Frequently Asked Questions About The Unsure Entrepreneur

What is The Unsure Entrepreneur about and what kind of topics does it cover?

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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Which podcasts are similar to The Unsure Entrepreneur?

These podcasts share a similar audience with The Unsure Entrepreneur:

1. The Loonie Hour

How many episodes of The Unsure Entrepreneur are there?

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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Our systems regularly scour the web to find email addresses and social media links for this podcast. We scanned the web and collated all of the contact information that we could find in our podcast database. But in the unlikely event that you can't find what you're looking for, our concierge service lets you request our research team to source better contacts for you.

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What guests have appeared on The Unsure Entrepreneur?

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

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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