Side Hustle Hero

Hosted by Joan Posivy

Business Entrepreneurship Education

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Episodes

205

Latest episode

Oct 2026

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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

November 10, 2026Episode 20652 min

206: How an Oncologist Grew a Travel Side Hustle to $4M in Sales (Through Referrals!)

A week before her family's trip to Hawaii, oncologist Merry Jennifer Markham realized the planning had been her favourite part of travelling. She shared the idea with a friend, and within 48 hours she'd bought a domain name. Merry Jennifer tells us that her travel side hustle, MMarkham Travel, did more than $4 million in sales, almost entirely through referrals, and she still works three and a half days a week in medicine. In this episode, you'll learn: How your next side hustle idea might be found in your day job The difference between a travel agent and a travel advisor, and how host agencies work Why she charges a planning fee, and why it grew from $200 to $750 and up How commissions work, and why they can arrive months after a client travels The Galapagos booking mistake that taught her to make sure she gets paid What she learned about pricing group trips What it really costs to start as a travel advisor, from about $40 a month to a $10,000 investment Why paid ads didn't work for her, and where her clients come from instead How she told her employer about her side hustle and set clear boundaries 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/206 Connect with Merry Jennifer: MMarkham Travel LinkedIn Connect with Joan: Instagram Facebook About Joan Be on the show! Do you have a side hustle success story to tell? We want to hear from you.

October 27, 2026Episode 20526 min

205: 10 Years of Rejections, Then The New York Times Crossword

What does it take to turn a hobby into a side hustle that lands in The New York Times? For Mark MacLachlan, it took ten years of rejections. By day, Mark is a chemist and the Dean of the Faculty of Science at the University of British Columbia. On evenings and weekends, he creates crossword puzzles. After nearly a decade of submissions, his first puzzle was accepted by the LA Times in 2016, and his second ran in The New York Times, where more than 200 puzzles compete each week for just seven spots. He kept his side hustle a secret from most of his colleagues for almost 20 years, and when word finally got out, paid contracts followed. Even if you have zero interest in crosswords, Mark's story will inspire anyone stuck in that stretch where the effort is high and the results are slow. In this episode, you'll learn: How a crossword puzzle is built, from theme to final clue What separates a puzzle that gets accepted from one that gets rejected What crossword constructors get paid, from about $200 to $2,500 US per puzzle How Mark fits 30 to 40 hours of work per puzzle around a demanding full-time career How going public with his side hustle brought new paid work his way Where AI helps him, and where it falls short Mark's two best tips to start and grow your side hustle Be sure to catch the wrapup where I take a close look at the myth of the overnight success, and why choosing a side hustle you truly enjoy matters when the results take 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/205 Connect with Joan: Instagram Facebook About Joan Be on the show! Do you have a side hustle success story to tell? We want to hear from you.

October 6, 2026Episode 20436 min

204: How to Earn $2,500 per Month as a Part-Time Speaker

What if a single talk a month could add $2,500 to your income? It could be a boost to the side hustle you already have, or a brand-new side hustle of its own. My guest today says that's realistic by the end of your first year if you're willing to put in the work. One of the speakers she manages now earns $100,000 for a single hour on stage. When she started working with him, he was getting a mere $500 for a gig. Li Hayes is the founder of the speaker management agency Go Leeward and host of the Path to the Main Stage podcast. Today, Li walks us through; the path from that first free talk to $2,500 per gig the thing to figure out before you write a single word of your talk when speaking for free is a really smart move how to price virtual gigs (yes, there is a difference!) how to handle travel costs, and the biggest mistake new speakers make on stage. And if you're an introvert like me who thinks this isn't for you, Li might just change your mind! Plus, I share how one piece of honest feedback during a sales pitch led me to Toastmasters, and why practising in front of people who will tell you the truth, is one of the best ways to prepare for paid speaking gigs. 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/204 Connect with Li: Path to the Main Stage Podcast Connect with Joan: Instagram Facebook About Joan Be on the show! Do you have a side hustle success story to tell? We want to hear from you.

September 22, 2026Episode 20317 min

203: 9 Fan-Favourite Side Hustle Hero Episodes: An Encore Edition

What do AI vending machines, sound baths, faceless YouTube videos, and mystery shopping have in common? They all made it into the Top 9 most loved side hustle episodes from Year 3 of the show…as chosen by you! Welcome to this encore episode! It first aired back in June 2025, and a lot has changed with AI since then. When I looked back at the side hustles featured in this episode though, they're all still strong choices. Some have since been tweaked or enhanced by AI to varying degrees, but with the right approach, every one of them is still viable today. This encore brings back the top 9 most loved episodes - as chosen by audience downloads, watch time, comments, feedback, and heaps of analytics across all major podcast apps and YouTube. "AI Vending Machines" took the #1 spot on both platforms, but after that, listener and viewer favourites went in very different directions. This recap features top episodes on everything from: Starting a sound bath business Becoming an Amazon Influencer Making faceless viral videos Hosting profitable craft workshops Mystery shopping for real income Renting out luxury restroom trailers … and more. Discover what made these episodes stand out, and which one you might've missed that could inspire your next side hustle. 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/203 Connect with Joan: Instagram Facebook About Joan Be on the show! Do you have a side hustle success story to tell? We want to hear from you.

September 8, 2026Episode 20215 min

202: How to Choose the Best Side Hustle for You

With hundreds (thousands?) of side hustle ideas out there, the hard part isn't finding one, it's figuring out which one actually is a fit for you . Today I walk you through the process I've successfully used over the years to help people cut through the noise and land on a side hustle that fits their life, strengths, and goals. In this episode, you'll learn: How to mine your own interests and hidden skills for side hustle ideas, and why AI can help but can't do this part for you The lifestyle-alignment questions, and why skipping them is one of the top reasons side hustles fail Whether you should ever turn a passion into a side hustle (including a story about a friend who turned down buying into a ski hill) A simple way to break a tie when you're stuck between two or three ideas you genuinely can't choose between By the end of it, you'll have a real answer, or at least a real shortlist, for which side hustles are actually worth your 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/202 Connect with Joan: Instagram Facebook About Joan Be on the show! Do you have a side hustle success story to tell? We want to hear from you.

August 25, 2026Episode 20155 min

201: How a Small Email List Can Be Your Most Valuable Asset

Think your email list is too small to matter? Copywriter Tanya Brody says think again. In this episode, Tanya makes the case for why a small, engaged list can outperform a massive disengaged one, whether you're starting from zero or already have a hundred subscribers, fifty, or just three. We cover: Why showing up each week beats list size How to start building an email list from scratch (and grow from a small one) The "serve first, sell second" approach to writing emails people actually want to open What a strong welcome sequence looks like How to keep your list healthy and deliverable over time How Tanya uses (and doesn't use) AI in her own email writing Tanya also shares why treating your list like an ongoing relationship, not a broadcast, shapes how people respond to what you send. Whether you're just starting your side hustle or have been putting off building an email list until you have "enough" people, this episode will change how you think about the list you already have. 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/201 Connect with Tanya: Her copywriting website Subject Line Generator Connect with Joan: Instagram Facebook About Joan Be on the show! Do you have a side hustle success story to tell? We want to hear from you.

July 28, 2026Episode 20054 min

200: AI Didn't Kill the Virtual Assistant Side Hustle: Here's How to Start One

Is being a virtual assistant still a viable side hustle in this age of AI? Today's guest, Rachael Davila, is here to show us why the answer is yes, and how you can turn your existing skills and experience into a VA business. Rachael has been a virtual assistant for more than 20 years. But today, she's also a VA mentor, author, and the founder of Extra Hands! Virtual Assistance. In our conversation, she draws on her decades of experience to share valuable insights on finding and working with the right clients, why the best VAs think beyond simply completing tasks, and how the right mindset can help you confidently charge what you're worth. We also get into practical details, from pricing and the best billing model, to the different ways you can structure your business so it actually pays you, and how to get started without having to know everything before you begin. In this episode: Why AI hasn't replaced virtual assistants ... and what it still can't do The difference between a "doer" VA and a "collaborator" VA How to price your services and get comfortable charging what you're worth A prepaid billing system that solves the "you're almost out of hours" problem What to ask (and listen for) in a discovery call before taking on a new client How to get started as a VA without already knowing everything 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/200 Connect with Rachael: Extra Hands! Virtual Assistant Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

July 21, 2026Episode 19947 min

199: Why Fewer Clients Meant More Revenue

What if the fastest way to grow your business isn't more clients, but fewer? Today, Damien Schreurs founder of EasyTECH, shares how he built his side hustle: testing ideas for free, negotiating time away from a full-time R&D engineering job, and running on minimal sleep just to make it all fit. When he finally went all-in, he was confident he had the right plan. He didn't. Damien came within one late invoice of bankruptcy, and it took a friend from his networking group pointing him toward the right training and mentorship before he found the number that actually mattered: revenue per customer. That single shift led him to cut his client list from 45 down to 9, multiplying his revenue per customer by nine times in the process. In this episode, you'll hear: The real math behind "fewer clients, more revenue," and why total client count can be the wrong thing to chase How Damien nearly lost everything before he found the metric that turned his business around Why he kept running a newsletter for years out of pure habit, long after it stopped working for him The one regret he still carries about staying quiet about his business, and what he'd do differently How he's using AI today as a co-CEO, CMO, and CFO for EasyTECH 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/199 Connect with Damien: LinkedIn Macpreneur Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!

July 14, 2026Episode 19833 min

198: Turn Your Everyday Skills into Paid Offers

You have a skill you're not counting as a skill. Because it comes so easily to you, it doesn't feel like something anyone would pay for. Adrienne Wheeler disagrees, and by the end of this episode, you might too. Adrienne spends her days in call center management and her side hustle helping people - which includes chefs, security guards, bakers, even someone who helps her mom's generation get their Wi-Fi working - turn the thing they already know how to do into a real, paid offer. In this episode, we cover: How to spot the skill you're already sitting on (even if it feels too easy to count) The Do It Yourself / Do It With You / Do It For You framework for structuring any offer Why pricing isn't about your time, but rather it's about the value you're creating How to price your first offer, and when to raise it What to do with the fear, the doubt, and the loneliness that come with building something new 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/198 Be on the show! https://www.sidehustlehero.com/guests/intake/

July 7, 2026Episode 19747 min

197: $500 for the Hour: The Wedding Officiant Side Hustle

What if you could earn a surgeon's hourly rate without years of school, a huge student loan, or even a related degree? In some places, all it takes is an online ordination, a script, and about fifteen minutes on your feet. Today we'll hear from Brad Lau, a wedding officiant who has led over 800 ceremonies and built a business people now pay $500 a wedding for. Brad walks us through how he got started, how he turned his very first nervous, low paying weddings into a stream of five star reviews and referrals, and why he believes stepping in front of a room full of strangers and making them feel comfortable is the real skill behind the job. But is this side hustle scalable? Brad's wife has turned it into a full service operation by layering in photography, hair and makeup, florists, and more. Whether you want to keep this simple as a weekend side gig or turn it into something much bigger, Brad breaks down the real numbers, the marketing strategy, and the mindset that got him started: stop planning to plan, and just start. Topics covered in this episode: How Brad built his first year of bookings starting from zero The strategy he follows for turning happy guests into five star reviews What officiants actually charge and how and when to collect payment How to expand a simple side hustle into a bigger operation Why you must check your local requirements before you get started Brad's best advice for anyone afraid to start something new Freebie alert! Brad is offering listeners a free 30-minute video consult to help you get your own version of this business off the ground. Just mention you heard about him on Side Hustle Hero. 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/197 Connect with Brad: Wedding Officiant Website Connect with Joan: Instagram Facebook About Joan Be on the show! Tell us about your side hustle success story!