Side Hustle Hero Podcast with host Joan Posivy
Hosted by Joan Posivy
A podcast offering practical advice and inspirational stories for people looking to start and grow a source of income outside their day job.
Side Hustle Hero is a hybrid-format podcast that serves as both a mindset coach and a practical business guide. Solo episodes see host Joan Posivy tackle the psychological hurdles of entrepreneurship, like self-sabotage and fear, often using personal anecdotes. Interview episodes are chronological deep-dives into the journeys of successful side hustlers, focusing on their origins, financial milestones, and specific operational tactics.
“The show's unique angle is its dual focus on mindset and mechanics. Unlike many business podcasts, it explicitly addresses the psychological barriers to starting, while its interviews are notable for probing into specific financial details like startup costs and revenue figures, grounding aspirational stories in reality.”
Who hosts this show
Joan Posivy hosts this podcast dedicated to building the courage and confidence to launch a profitable side hustle. She is the bestselling author of "The Way Success Works: How to Decide, Believe & Begin To Live Your Best Life" and has a background as an entrepreneur and former bank manager. Through a mix of solo episodes and interviews, she provides listeners with actionable strategies and insights from experienced entrepreneurs.
Credentials & credits
- Bestselling author of "The Way Success Works"
- Host and producer of the Side Hustle Hero podcast
- Former bank manager, reportedly the youngest in Canada at the time of her appointment
- Founder of training company Programs for Peak Performance
- Entrepreneur (revitalized a failing delicatessen, ran a Christmas tree lot)
Other ventures
- The Way Success Works (Book)
- sidehustlehero.com (Official Website)
- Programs for Peak Performance (Training Company)
- Online Masterclass: How To Turn Your Thoughts Into Wanted Things
What kind of podcast
When new episodes drop
- 01Why Right Now Is Your Competitive Advantage | Starting During Economic UncertaintyJun 24, 2026 · 16 min
- 02
- 03Is Your Mindset Killing Your Side Hustle? - 3 Stages of Self SabotageMay 12, 2026 · 25 min
- 04Building A Six-Figure Side Hustle That Actually Gives A DamnApr 28, 2026 · 51 min
- 05Authentic Connections: The One Thing AI Can't ReplaceApr 21, 2026 · 25 min
- 06Why a Side Hustle Gets You Noticed at WorkApr 7, 2026 · 26 min
- 07How to Turn Your Skills Into Multiple Income StreamsMar 31, 2026 · 20 min
- 08Side Hustle Not Making Money? Start HereMar 24, 2026 · 8 min
Notable episodes
- 01Photo Booth, Bubble Soccer, Amazon FBA: How He Built Multiple Side Hustles That Replaced His Income
A quintessential interview episode demonstrating the host's chronological style and focus on financial specifics as she deconstructs a guest's journey from zero to a $3M/year business.
- 02Is Your Mindset Killing Your Side Hustle? - 3 Stages of Self Sabotage
This episode showcases the show's solo-host, mindset-focused format, where Joan Posivy breaks down a key psychological barrier to success using personal stories and concepts like the 'mental thermostat'.
- 03Why Right Now Is Your Competitive Advantage | Starting During Economic Uncertainty
Highlights the host's use of personal narrative, telling the story of her own success buying a failing business during a recession to inspire listeners to act despite economic fears.
What you'll be asked on this show
Joan Posivy's interview style is methodical and chronological. She typically begins by asking about the guest's very first venture and proceeds sequentially through their journey. A signature of her approach is to repeatedly ask for specific financial details, such as startup costs, pricing structures, and the revenue milestones that enabled them to quit their day jobs. She frequently clarifies industry jargon (like 'FBA') for the audience and uses transitional phrases like "Apparently that wasn't enough..." to move the story from one business to the next. Her questioning aims to deconstruct a guest's success into a series of practical, understandable steps.
The podcast alternates between solo narrative episodes and guest interviews. Joan's solo shows are tightly structured around a single theme (e.g., self-sabotage) and often incorporate clips from past interviews. Interview episodes chronologically trace a guest's path from their first side hustle to their current success. A consistent feature is the host's sign-off, "Hustle on."
Questions Joan Posivy keeps coming back to
10 cataloguedIf you're going on this show as a guest, expect some version of each of these. Each note explains when Joan Posivy reaches for it.
origin
2- Q.01
“Walk us through how this side hustle got started.”
This is often her opening question, used to establish the origin story of the guest's first venture.
- Q.02
“What was the next side hustle you added to your plate?”
Used as a transition to explore how the guest expanded from one income stream to another.
process
4- Q.01
“How were you finding customers in those early days?”
She asks this to uncover the guest's initial marketing and customer acquisition tactics.
- Q.02
“How did you choose which products would be lucrative?”
This question probes the guest's research and validation process before launching a product or service.
- Q.03
“What gave you the credibility to deal with suppliers/wholesalers?”
She asks this to understand how new entrepreneurs establish trust and legitimacy in their industry.
- Q.04
“Can you define [industry jargon] for our listeners?”
She frequently pauses the conversation to have guests explain acronyms or technical terms.
money
2- Q.01
“Can you give us a rundown of the numbers, like startup costs or pricing?”
A recurring question used to ground the narrative in concrete financial details for the listener.
- Q.02
“What were your earnings by the time you quit your full-time job?”
A key question to identify the specific financial tipping point that made entrepreneurship a full-time reality.
mindset
2- Q.01
“Why did you decide to focus on one business and sell the others?”
This question explores the strategic thinking and lifestyle choices behind scaling or simplifying their business portfolio.
- Q.02
“What's the biggest challenge for people just getting started?”
Often used in solo episodes or to frame a discussion around common entrepreneurial roadblocks.
Signature segments
- · Sign-off: "Hustle on."
- · Branded intro/outro music sequence
- · Host's personal anecdotes about her own business ventures
- · Focus on overcoming mindset blocks and self-sabotage
Topics covered repeatedly
Who gets booked here
Guests are typically entrepreneurs who have successfully built one or more side hustles, often to the point of replacing their full-time income. They come from a diverse range of industries, including e-commerce (Amazon FBA), local services (photo booths), and consulting.
- Rich Potteron Photo Booth, Bubble Soccer, Amazon FBA: How He Built Multiple Side Hustles That Replaced His Income
- Laura Nicole Jenningson Is Your Mindset Killing Your Side Hustle? - 3 Stages of Self Sabotage
- Colin Macintoshon Building A Six-Figure Side Hustle That Actually Gives A Damn
- Melissa Snowon Authentic Connections: The One Thing AI Can't Replace
- Roger Smithon Why a Side Hustle Gets You Noticed at Work
- Norman Leachon How to Turn Your Skills Into Multiple Income Streams
Where to find this show
Audience & reach
Based on the episodes reviewed, the podcast primarily promotes the host's own products, including her book "The Way Success Works," a free "Smart Start" guide, and an online video course. There is also a call for listeners to provide support via a "virtual coffee" on the website.
Subscriber and view counts are pulled live from YouTube and re-verified on a 30-day cycle. Listener estimates for the RSS feed aren't published here unless they're host-verified.
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People also ask
- What is the host's name?
- The host is Joan Posivy. The name 'Joan Crossovy' appears to be a transcription error in one episode's data.
- Is the podcast still active?
- Yes, the podcast appears to be active, releasing episodes on a weekly basis as of mid-2026.
- What is the format of the show?
- It's a hybrid format, featuring a mix of solo episodes focused on mindset and strategy, and long-form interviews with entrepreneurs who have built successful side hustles.
- How can I pitch a guest for the show?
- The official podcast website has a section titled "Be on the show!" which invites listeners to share their side hustle success stories.
- Where can I listen to the podcast?
- Side Hustle Hero is available on YouTube and major podcast platforms like Apple Podcasts.
- What is the host's background?
- Joan Posivy is a bestselling author, speaker, and entrepreneur. She was a bank manager by age 22, later started several businesses including turning around a failing delicatessen, and founded a training company called Programs for Peak Performance.
Built from the show's public RSS feed, YouTube, the host's own websites, and the cited sources below. Computed and AI-extracted fields are labelled. Facts only — no private info, no fabrication, no transcripts republished.
Sources & how this page was built
This page is AI-assisted, grounded in the public sources cited below, and host-verifiable. We publish facts only; we do not republish transcripts. If anything here is wrong, the host can claim and correct the page above.Model: gemini-2.5-pro · high confidence
- [01]Official Podcast Websitesidehustlehero.com
- [02]Host's Official Websitejoanposivy.com
- [03]The Way Success Works (Book Page)joanposivy.com
- [04]Side Hustle Hero on Apple Podcastspodcasts.apple.com
- [05]Side Hustle Hero Podcast on YouTubeyoutube.com
- [06]Guest Appearance: All Ears Englishallearsenglish.com
- [07]Guest Appearance: The Agent of Wealth Podcastbautisfinancial.com
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