

Side Hustle Hero
Joan Posivy
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/
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/
Episodes
Mentioned books

Nov 18, 2025 • 38min
172: How to Start a Photo Organizing Side Hustle
I've got photos scattered everywhere - on my desktop, laptop, phone, Dropbox, the cloud, and who knows how many memory sticks. Can you relate? Chances are, yes. Most people are drowning in decades of digital and printed photos… and here's the surprising part: many would happily pay someone to sort it all out. That's where a photo organizing side hustle comes in. Cathi Nelson is a pioneer in this field, having built a business that helps people take control of their scattered digital photos, printed collections, home movies, scrapbooks, and other keepsakes. In this rebroadcast episode, you'll discover: the multiple revenue streams within a photo organizing side hustle how to price a job (including complex digital cleanups) where to find your first paying clients the tools you need ... and the ones you don't simple steps Cathi uses to organize her own photos the traits that make someone successful in this work how to grow from a small project to ongoing referrals We're talking about working with people's most meaningful keepsakes, so it's a side hustle that can be personally fulfilling as well as financially rewarding. 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/172 Connect with Cathi: The Photo Managers Academy - to learn how to organize your photos Photo Manager Training - Cathi's 1-year program to start and build this as a side hustle Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

Nov 11, 2025 • 13min
171: How to Surround Yourself with Success (and Why It Matters!)
Ever notice how one conversation can make you want to take on the world, and another can make you want a nap? Today I share a personal story from one of my own side hustles - buying a deli that was going out of business, to illustrate how the people you surround yourself with can directly shape your mindset, energy, and success. You'll learn how to recognize whether your current circle is fueling your vision or quietly holding you back, what to do when that negativity comes from someone you care about, and practical ways to intentionally build an environment that keeps you inspired and moving forward. If you've ever struggled to stay positive when those around you aren't quite on the same wavelength, this episode will help you protect your energy, upgrade your circle, and attract the kind of people who help you thrive. You'll Learn: How your environment and relationships directly influence your results Why even well-meaning people can unknowingly hold you back The story of how a struggling deli turned profitable through mindset and community What to do when a negative friend or family member drains your energy The five-step framework to intentionally upgrade your circle A simple trick Joan used to stay privately focused on her goals Why being the positive, encouraging person in someone else's life can elevate your own Listen to hear how surrounding yourself with success can completely change the trajectory of your side hustle — and your life. 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/171 Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

Nov 4, 2025 • 47min
170: Stop Undervaluing Your Work: 5-Part Framework To Profit
Have you ever wondered if you're charging too little for what you do? Or caught yourself thinking that lowering your price will make it easier to sell? This episode could change that, and quite possibly make you more money. Author, coach, and 6-figure artist Miriam Schulman joins us to share her five-part framework that helps creatives and business owners turn their passion into profit. We dive into what those five parts are, how you can apply them to confidently charge what you're worth, stop undervaluing your work, and be ready when the right customer walks in — whether that's online or in person. You'll learn: The mindset shift behind charging premium prices with confidence The five core areas that drive creative income Why lowering your prices doesn't make sales easier — and what actually does How to believe in your customer even more than they believe in themselves Practical ways to turn your creative passion into sustainable profit 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/170 Connect with Miriam: Free Masterclass Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

Oct 29, 2025 • 42min
169: How to Earn $2K–$5K/Month Fundraising for Nonprofits
What if you could earn $2K–$5K a month using skills you already have, while helping causes you care about at the same time? Most people assume fundraising means simply asking for donations. This episode shows you how it actually becomes a paid side hustle by improving a nonprofit's messaging, website, email strategy, and storytelling so donors want to give. Fundraising pro, Elaine Allan, explains; what the work looks like, what to charge when starting out, how to land your first client, and why this is one of the few side hustles where your income and your impact show up in the same place. If you want a side income that is both profitable and meaningful, this conversation will show you a path most people never consider. 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/169 Connect with Elaine: Inbox Impact website Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

Oct 21, 2025 • 39min
168: The System That Drives Side Hustle Success
That system is EOS® - the Entrepreneurial Operating System. It's often seen as a system for big companies, but it can be adapted to give a solo side hustle the same benefits; clarity, structure, and follow-through. It gives you a simple structure to decide what matters, turn it into concrete 90-day priorities, and hold yourself accountable so the right work actually gets done. I tested it inside Side Hustle Hero and it immediately reduced noise, eliminated guesswork, and pushed the truly important work into my week. EOS Implementer Rani Dabrai explains how to apply EOS even if you're a team of one, so you can: stop reacting and start running with a plan replace intention with measurable execution make visible progress on a 10-year vision using 90-day moves Links to the downloadable VTO (Vision Traction Organizer) are in the show notes (which live at our website - link below), so you can start working through EOS for your own side hustle. Gain clarity, focus, and follow-through instead of overwhelm. 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 (which contain the VTO link) head on over to the home of Side Hustle Hero. https://www.sidehustlehero.com/168 Connect with Rani: LinkedIn Her EOS website page Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

Oct 14, 2025 • 17min
167: Grow Bigger Than Your Problems
Every side hustle comes with challenges, but what if the problem isn't really the problem? Here you'll discover why problems are not the problem, and how growing your capability changes everything. You'll learn how to: Reframe setbacks so they fuel your progress Strengthen your scale of capability to handle pressure Stay calm and confident when plans go sideways Turn obstacles into opportunities for growth If you're starting or scaling a side hustle, this conversation will help you build the mindset to face challenges head-on, and grow bigger than your problems. 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/167 Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

Sep 30, 2025 • 56min
166: How to Make Your Online Course Sell
Think you need to be a guru to sell an online course? Not true! Dan Henry explains why focusing on solving problems, and not teaching topics, is the real key to making your course sell. You don't need to be a world-class expert to create an online course people will pay for. Dan shows us how to stop obsessing over "topics" and instead focus on solving real problems … the kind that people will gladly spend money to fix. From doing a simple "brain dump" on your phone and running it through AI to uncover profitable course ideas, to understanding why solving an "insomnia" or even "bleeding neck" problem is far more valuable than teaching just another skill, Dan breaks it all down with clarity and candor. He also shares how his $37 mini-course turned into $150,000 in sales, and why shifting from "information" to "problem-solving" can completely change the way you approach creating your own course. 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/166 Connect with Dan: Instagram YouTube Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

Sep 23, 2025 • 43min
165: How to Start a Litter Cleanup Service
You're about to hear how to start a litter cleanup service, which is a low-cost, flexible business where you can literally get paid to go for a walk through parking lots and outside of commercial properties. Brian Winch (author of Clean Lots) returns to share the exact steps: which properties to target first, how to reach the decision maker at property management companies (and who not to pitch), what to say, how to handle the most common objection, and the simple free reporting add-on that helps you stand out. We also talk startup costs (basic hand tools + insurance), pricing and routes, why early morning is the sweet spot, and free publicity moves that have landed Brian media coverage. For context, Brian has grown this business to gross over $600,000 a year, and for beginners he explains how 2–3 hours a day can translate into $2K–$3K/month in extra income. If you want a simple, service-based side hustle with early-morning hours and room to scale, this episode gives you a practical blueprint. You'll learn: Best starter properties to pitch How to connect with the right decision maker What to say on first contact (and what to avoid) A low-effort value add that wins clients (free reporting) How to start smart so you don't get discouraged Free publicity tactics to grow faster 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/165 Connect with Brian: CleanLots website Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

Sep 16, 2025 • 32min
164: How To Find The Right Side Hustle Idea
How do you know which side hustle idea is right for you? Jason VanDevere, the author of Dream Driven, shares how to uncover an idea that actually fits your life, and how to test it before you sink time or money into it. You'll learn: Why dreaming daily can reveal the ideas that truly stick Jason's "3 L's" test (Longing, Lifting, Light) to know if an idea is right for you How to validate that your idea solves a real problem The best way to confirm demand: pre-selling vs. surveys The role of mentors, and creative ways to find them — even if you're starting from zero Why setting boundaries around your work time makes you more productive Get clear on a side hustle that lights a fire inside you, and not just one that looks good on paper. 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/164 Connect with Jason: Goal Crazy website His book, Dream Driven Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

Sep 9, 2025 • 28min
163: From Planner Idea to Six Figures
What happens when you walk away from the family business to chase an idea of your own? Jason VanDevere did exactly that, and grew his planner idea to a six figures business. Here in Part 1, he shares how the Goal Crazy Planner went from rough draft, to a product that has gained real traction. You'll learn: How he set up zero-cost focus groups Simple ways to recruit testers for free His launch & traction strategy How he went from idea to 6-figures If you're building something tangible and want real-world ways to test it, launch it, and get those first waves of customers, here Jason shares how. 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/163 Connect with Jason: Goal Crazy website His book, Dream Driven Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!


