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Side Hustle Hero

Author: Joan Posivy

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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/
187 Episodes
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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!        
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!        
If someone asked you what makes you unique, could you answer immediately? Many capable professionals struggle with that question because the very things that set them apart, often come so naturally they overlook them. Today, Kyle Elliott shares how to recognize your "fabulousness" - the qualities that make you distinct, valuable, and memorable in the marketplace. Kyle started his side hustle on Fiverr, charging $5 to review resumes and write LinkedIn profile summaries. Today he's a tech career coach, & trusted confidant to Silicon Valley's top talent. You'll also learn a practical exercise for uncovering patterns in what others consistently see in you, along with a simple tool you can create for yourself, to keep real reminders of your value close at hand. 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/185 Connect with Kyle: https://caffeinatedkyle.com/ https://www.linkedin.com/in/kylecromerelliott/ Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!      
Finding clients can take more time than actually doing the work, especially when you are building a side hustle alongside a full time job. But what if you could bring opportunities to you instead of constantly chasing them? Today Megan Leasher explains how she built a client pipeline by positioning herself inside existing ecosystems instead of relying on traditional outreach. Instead of hunting for clients, she focuses on partnerships, visibility, and strategic positioning that bring opportunities directly to her. She also shares how she structured things with her employer so her side hustle and full time role can coexist smoothly, along with practical steps you can take this week to start building your own pipeline. In this episode, you will learn: The three ways she consistently gets clients without chasing them How contractor pools and partner firms can become built in lead sources Why smaller firms can be powerful allies for growing your client base Low cost and no cost ways to build credibility and visibility How speaking, writing, and communities can act as referral engines What to know about joining a Forbes advisory council and whether it is worth it 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/184 Connect with Megan: LinkedIn Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!    
If you've been thinking about starting or growing a side hustle but haven't yet followed through, you'll want to check out this episode. Here I share a simple two-step accountability process I've used myself many times to move from talking about taking action, to actually doing it. I walk you through; how I create forward progress, why keeping your word matters so much, and how this approach helps you actually stay in motion on your side hustle without overcomplicating things or getting stuck in planning mode. 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/183 Be on the show! https://www.sidehustlehero.com/guests/intake/    
How do you turn a tour guide side hustle into a $600K local business in under three years? Paul Whitten shares the real strategies behind growing a simple weekend hustle into a high-margin tour company, by starting with just $3,600 and scaling through smart pricing, partnerships, and consistent customer demand. In this episode, you'll learn: How Paul attracted his first customers with no marketing budget Why Google reviews and platforms like TripAdvisor became growth engines The upselling approach that increased revenue without sounding salesy How private and corporate events boosted profits Ways to turn one service into multiple revenue streams If you're building a side hustle, or thinking about starting one, this episode shows what's possible when you dream big, have a vision, and are willing to put in the work. 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/182 Connect with Paul: Nashville Adventures website Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!      
Delegating is one of the hardest skills for side hustle owners to master, especially when you care deeply about your business and want everything done right. Today Renee Hastings shares why fear, perfectionism, and trust issues often stop entrepreneurs from letting go, even when they know it's holding them back. You'll learn: What tasks make sense to delegate first  How to set clear expectations so things don't fall apart Common mistakes that can derail the process If you've ever felt overwhelmed trying to do everything yourself, this conversation will help you start building a side hustle that can actually grow. 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/181 Connect with Renee: Executive Help Now website Renee's LinkedIn Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!      
Side hustles are no longer just about earning extra money. For many professionals, they've become a strategic part of modern career planning. Here we break down why side hustles are becoming a normal part of professional life. We look at how building something alongside your career can help you stay relevant, build real assets, and create options beyond a single employer. We walk through five reasons forward-thinking professionals are choosing to build side hustles intentionally. They can: Keep professional skills current, relevant, and adaptable Allow you to build assets you actually own Increase credibility and professional respectability Create a portable network that stays with you over time Provide leverage, flexibility, and long-term security This episode will help you take a more deliberate approach to building a side hustle, not as a hobby or a backup plan, but as a smart extension of your career. 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/180 Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!      
Most people don't fail because they lack ideas, talent, or motivation. They stall because they're waiting to feel ready. In this episode, I revisit a powerful conversation from the very beginning of the Side Hustle Hero podcast with my first-ever guest, Joel Young. It opens with a simple but uncomfortable truth: you don't really grow until you're willing to fail ... in front of other people. Joel shares how he got started recording voiceovers in his closet with almost no experience, no studio, and no certainty about where it would lead. That willingness to start before he felt ready eventually helped him become one of Fiverr's all-time top earners, with $2.7 million in earnings at the time of our interview. In this conversation, we talk about: why waiting for confidence keeps most people stuck why practicing in private only gets you so far how starting before you feel ready builds real skill how reframing what you think of as "giving something up" can make working on a side hustle feel more empowering If you've been holding back because you don't want to look foolish, make mistakes, or put yourself out there before you feel ready, this conversation will help you rethink what it really takes to get started. 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/179 Connect with Joel: Joel's Main Site JumpStart Video Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!      
Most "top 10 side hustle" lists recycle the same ideas with very little context. This episode takes a different approach. These 10 side hustles are drawn from real conversations with guests who are actually doing the work. Some are simple and inexpensive to start. Others require more capital or coordination. None are ranked, because the right side hustle depends on your situation and circumstances. The list includes mystery shopping, selling at farmers markets, printables, online courses, virtual assistant work, AI workflow consulting, fundraising, direct mail postcards, high-ticket dropshipping, and luxury restroom trailers. The focus is on what's working heading into 2026, what often flies under the radar, and how people are building income without chasing hype. 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/178 Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!      
Why do so many people quit their side hustle, even when the idea itself isn't bad? Today I break down 3 real reasons most people walk away from their side hustle and why quitting is often more about behaviour than talent, motivation, or market demand. If you've ever started a side hustle, put in the effort, and then stopped (especially when the money didn't show up as quickly as you hoped,)  you're not alone. You'll learn: Why early income is a lagging indicator, not a verdict on your idea The three most common reasons people quit too soon How starting too big actually works against you Why lack of clarity around progress creates unnecessary doubt How isolation sabotages follow-through What to do differently next time so quitting isn't the default response This isn't about pushing harder or working longer hours. It's about setting yourself up with the right expectations, structure, and support so your side hustle has a real chance to grow. 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/177  Share this with someone who's tried before and is thinking about giving it another shot. Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!    
Building a business that is a profitable side hustle from the start is not about luck. It comes down to the decisions you make early and the discipline to stick with them. Today I revisit my conversation with Mellisa Mills, founder and CEO of Millsie, formerly known as Spread'Em. Mellisa built her "cashew dip" company that has been profitable from day one and has grown into a multi million dollar business without outside investors. This episode pulls together the most valuable lessons from our original interview, including: How Melissa tested demand before scaling Why she prioritized margins and cash flow over rapid expansion How reinvesting profits allowed the business to grow steadily and sustainably Why slower, more intentional growth can outperform build fast strategies, especially in product based businesses Since this interview, Spread'Em has been rebranded to Millsie, a change driven by growth, clarity, and an expanding footprint in the United States. If you are building a business or thinking about starting one and want a grounded, real world perspective on profitability, decision making, and figuring things out as you go, this episode offers practical insights you can apply immediately. 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/176 Connect with Mellisa & Millsie: LinkedIn Millsie website Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!      
If you keep telling yourself you want to start a side hustle, but weeks keep passing with no real movement, there's a reason. And it's not a lack of ideas, time, or talent. It's the silent mindset traps that play out in the background and quietly keep you stuck at the starting line. After interviewing more than 170 side hustle heroes, I've heard the same patterns again and again. Today we break down 7 of the most common thinking mistakes that stop people from ever getting traction: Waiting to feel ready Overlearning instead of acting Staying busy with low-impact tasks Underestimating the value of your skills Comparing your Day 1 to someone else's Year 5 Believing confidence must come first Falling into the all-or-nothing time trap You'll learn how each one shows up, how to spot it in yourself, and what small, practical shift gets you moving. By the end of this episode, you'll know exactly which mindset has been holding you back, and the next step that will move your side hustle forward today. 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/175 Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!      
If you've been searching for remote side hustles but keep running into unrealistic promises of passive income and overnight success, this episode takes a different approach. Here Joan shares 10 real remote side hustles to make money from home, based on actual examples from her first hand experience and past Side Hustle Hero guests. These are practical ways to make money from home that fit around full-time jobs, family life, and real schedules, without shortcuts or hype. The side hustles are presented in no particular order and cover a mix of service-based work, creative income, digital products, and client-based roles. You'll also hear honest discussion about income ranges, startup costs, and what it actually takes to sustain each option. 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/174 Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!    
If you've ever wanted a simple side hustle with no upfront costs, this episode may spark something for you. Rachel Smith and Dalton Joyner break down how they run "Community Postcards," a direct-mail model where they sell ad space on physical postcards, design the layout, and mail them out … all after advertisers have already paid. You'll hear how the model works, why business owners say yes, and what you can realistically earn each month. In this episode, you'll learn: how to start a postcard side hustle with zero upfront expenses the exact pitch they use to land $150 advertisers what to expect in terms of time, income, and workflow how to keep your risk close to zero ways this simple project can lead to larger recurring clients If you enjoy connecting with local businesses and want something easy to test, this is a model worth considering. 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/173 Connect with Rachel & Dalton: Free Community Card Playbook Mini Course Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!    
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!      
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!    
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!    
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!      
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!      
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