Side Hustle Hero

Hosted by Joan Posivy

Business Entrepreneurship Education

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Episodes

194

Latest episode

May 2026

Language

EN-US

About the show

Side Hustle Hero is the podcast for everyone who wants to build the courage, confidence, and drive to launch, persevere, and succeed at creating a source of income beyond their regular job. Each episode is crafted with the goal of having you take action and win. You'll hear insights from experienced side hustle heroes who share what's worked and what hasn't so you can execute smarter and for more profit. Hosted by Joan Posivy, bestselling author of The Way Success Works, How to Decide, Believe & Begin To Live Your Best Life. Listen online https://www.sidehustlehero.com/ Connect with Joan https://www.joanposivy.com/

Listen to episodes

60 recent

June 16, 2026Episode 19543 min

195: Photo Booth, Bubble Soccer & Amazon FBA: How One Guy Built Multiple Side Hustles That Replaced His Income

What would you do if 70% of your income was about to disappear overnight? Rich Potter didn't panic. Instead, he went home, talked to his wife, and started building. What followed was a photo booth business, a bubble soccer company, and an Amazon FBA operation that Rich reports is now doing $3M a year in sales. All of it built on the side while he kept his day job. One by one, those side hustles replaced his income entirely. Today Rich walks us through how he did it, what it cost, what he learned, and what he'd tell anyone just starting out today. In this episode you'll hear: How Rich borrowed $10K from his dad to buy his first photo booth, and why it was the wrong one What bubble soccer is and how he stumbled into it as a side hustle Why the potential of losing a client that represented 70% of his commissions was the wake-up call he needed The real reason he sold two of his businesses What he learned going to conferences and connecting with others His advice for anyone sitting on a side hustle idea right now Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/195 Connect with Rich: Franchise Heroes LinkedIn Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

May 12, 2026Episode 19424 min

194: The Three Stages of Side Hustle Self-Sabotage - Which One Is Stopping You?

If you've been wanting to start a side hustle, or grow the one you've got, but something keeps getting in the way, this episode is for you! In my conversations with people lately, the thing holding them back has nothing to do with their idea, the market, or the timing. In every case, the obstacle is internal. They're getting in their own way. Self-sabotage doesn't just show up once. On the side hustle journey it shows up at three very specific stages, and each time it looks a little different, which is exactly why it's so easy to miss. In this encore episode you'll learn: The three stages where self-sabotage shows up on your side hustle journey and how to recognize each one Why "productive-looking" procrastination is one of the sneakiest forms of self-sabotage The escape hatch moment; what it is, when it hits, and how to push through it Why success itself can trigger a pullback and what to do when opportunity shows up and your instinct is to shrink The one commitment to make before you launch that can change everything If you've ever wondered why you keep getting in your own way, you've landed in the right spot. Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/194 Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

April 28, 2026Episode 19351 min

193: From Fired to 6-Figure Side Hustle: Building Businesses That Give a Damn

What does it take to go from getting fired at 27 to building a 6-figure side hustle? If you ask Colin Macintosh, the answer might surprise you. It's not the flashiest strategy or the biggest budget. It's something a lot of businesses have stopped doing altogether, genuinely caring about the people they serve. Colin is a CTO recruiter by day and side hustle entrepreneur by night. He got fired at 27, and somewhere between the pink slip, the margaritas, and a movie he'd watched, an idea was born. That idea became Sheets and Giggles, a eucalyptus bedsheets brand he built, scaled, and exited. But this episode is really about what came next. Dirt Cheap Compost is exactly the kind of side hustle I love most; simple, low cost, profitable, and scalable. No complicated tech stack, no outside funding. Just a real problem, a real market, and a flyer tucked inside a Halloween pumpkin. Sheets Resume is a different kind of story. An AI-powered resume builder doing thirty thousand resumes a month that sounds like an overnight success, until you find out about the years old Reddit post driving all that traffic. In this conversation Colin and I cover: The lessons from Sheets and Giggles that shaped everything that came after Why raising venture capital was a treadmill he'll never step on again How a $40K compost business was built with flyers and a seasonal pumpkin campaign How a Reddit post written in 2018 became the foundation of a 6-figure side hustle The customer experience rule that turns buyers into your most powerful sales people Colin genuinely gives a damn; about his customers, about the problems he's solving, and about the people he builds with. And as you'll hear today, that's not just good character ... it's good business. Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/193 Connect with Colin: Personal Website Sheets Resume Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

April 21, 2026Episode 19225 min

192: How to Win with Real Human Connection While Everyone Else Goes AI

If you've ever walked into a networking event and thought, "What am I even doing here?" this episode is going to change how you approach it. With more people relying on AI to write their content, messages, and outreach, real human connection networking is becoming the advantage. The problem is, most people either try to connect with everyone or leave without building anything meaningful. In this episode, Business Relationship Strategist Melissa Snow shares a smarter, more intentional way to network. One that saves you time, feels natural, and actually leads to relationships that matter. You'll learn: How to decide who you actually want to connect with before you walk into a room Why networking isn't about finding clients (and what to focus on instead) The biggest mistakes people make at events that cost them opportunities How to follow up in a way that feels genuine and gets responses If you're more introverted or networking has ever felt forced, her approach will feel like a sigh of relief. Fear not... this is not about "working the room." Instead, it's about building the right relationships that support your side hustle long term. Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/192 Connect with Melissa: Her website Melissa's Co-ed Virtual Networking Recommendation: Laura Livingston's Real Connections Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

April 7, 2026Episode 19126 min

191: Why a Side Hustle Gets You Noticed at Work

So what makes someone get noticed at work? If you're doing good work, showing up, and delivering results, you'd think that would be enough! But often, it's not. And this is where side hustles come in, because what you do outside your job can start to change how you're viewed at work. Today you'll hear how Roger Smith's side hustles changed the trajectory of his career. Roger is a computer scientist who went on to become Chief Technology Officer for the U.S. Army, worked inside a surgical training center, and now consults in robotic surgery. As he explains, none of that came from applying for jobs in the traditional way. He started to get noticed and stand out from his peers because of what he was doing on the side. I first sat down with Roger a couple of years ago, and for this episode, I pulled key excerpts from that conversation that show how it all came together. In this episode: How a side hustle can lead to unexpected opportunities Why you don't need to have everything figured out to start One way to stand out without changing jobs Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/191 Connect with Roger: His book website - Medical Thrillers of the Near Future Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

March 31, 2026Episode 19019 min

190: How to Turn Your Skills Into Multiple Income Streams

Most people think they need one great side hustle idea. But that's not the only path. Today you'll hear from Norman Leach, how multiple income streams can come from at least three places that are already part of your life: the skills you have, the problems you notice, and the interests you naturally follow. None of his multiple income streams started as big, polished business ideas. Instead, they started small, and grew over time. If you've been waiting for the "right" idea, may this episode help you see that it's closer than you think. In this episode, you'll hear: How a simple skill turned into a long-term income stream How noticing a problem led to a business opportunity Why not every side hustle needs to be a full business How one interest can lead to multiple opportunities over time Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/190 Connect with Norman: LinkedIn Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

March 24, 2026Episode 1898 min

189: Make Your Side Hustle Pay - What to Focus on First

If you've been putting time into your side hustle but not seeing much return yet, this condensed episode will help you take a step back and refocus. You'll hear four simple areas to focus on so you can zero in on what actually brings in revenue, along with a practical way to start buying back your time so you're not doing everything yourself. We also get into what it really costs to get help, and why it may be more accessible than you think. If you've been struggling to get traction and make your side hustle pay, this conversation is a good place to start. Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/189 Connect with George: (at his website and for his book) Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

March 17, 2026Episode 18849 min

188: How to Earn Up to $10K/Month as a Baby Sleep Consultant (From Home)

If you have ever wondered whether a simple service could become a profitable side hustle, this episode offers a fascinating example. Jayne Havens built a successful business as a baby sleep consultant, helping exhausted parents get their babies and toddlers sleeping through the night. What started as helping friends turned into a flexible consulting business that now supports families around the world. In this conversation, Jayne explains how the baby sleep consulting business works and how she built a client pipeline that consistently brings in new families. In this episode you will learn: How Jayne built a thriving business as a baby sleep consultant Why you do not need to be a parent yourself to succeed in this field What a typical day looks like for a sleep consultant How much sleep consultants charge and how pricing works The importance of pre screening potential clients before booking calls How referral partnerships helped grow her consulting business Who makes the best sleep consultants Even if you have no interest in becoming a baby sleep consultant, the strategies Jayne shares apply to almost any side hustle. From structuring discovery calls to building trusted partnerships, this episode offers practical ideas that entrepreneurs can adapt to their own businesses. If you are exploring service based side hustles or looking for a niche where expertise can translate into real income, this episode will give you a clear look at how one entrepreneur built a successful business helping families sleep better. Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/188 Connect with Jayne: The Snoozefest.com Website Centre for Pediatric Sleep Management Becoming A Sleep Consultant Podcast Becoming A Sleep Consultant Facebook Group Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

March 10, 2026Episode 18736 min

187: From Furloughed to $560K Agency

What would you do if your job disappeared tomorrow? After six years at Ticketmaster, that's what happened to Rachel Minion. She was suddenly furloughed during the pandemic. At the same time, her husband had just been laid off. There was no backup plan. But Rachel had something that many of you have or are wanting to have ... a side hustle with a small handful of clients. So she made a decision. She called those clients and told them she was now available full-time. She shares that since then, her marketing agency is now generating about $560,000 a year. We also learn from Rachel, how she made the leap from side hustle to full-time business, how she turns expertise into offers clients will pay for, and why marketing your own business, can feel harder than marketing someone else's. If you're currently building something on the side or thinking about starting, this conversation with Rachel may expand what you think is possible, for you. Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes and links, head on over to the home of Side Hustle Hero. Connect with Rachel: Website Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

March 3, 2026Episode 18632 min

186: 3 Things That Make Clients Choose You

Branding seems to be important, but at the same time, can be hard to pin down. So in this episode, we're making sense of it. You'll hear from brand strategist Rob Genovesi about the three things that made the difference in 4X'ing his revenue, without making big changes. We touch on all three, but spend most of our time on what makes you different and how to express that more effectively so people remember you and choose you. You'll also hear about a few simple and practical shifts, the kind Rob calls "dumb little things," that don't cost anything but can change how people experience your work. Since recording this conversation, I've already implemented two of them and I share what I did in the end of the episode wrap-up. Let me know your key takeaways, as I always love hearing what resonates with you. Do you like what you're hearing? Consider giving it a caffeinated thumbs up. We'd really appreciate it! Need a little (and sometimes big) push to start and stay focused to grow your side hustle? Dive into my online Masterclass: How To Turn Your Thoughts Into Wanted Things. For the full show notes and a link to a free digital copy of Rob's book, Don't Fear The Brand, head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/186 Connect with Rob: LinkedIn Rob's Build Strong Brands website Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!