By day, Bryan Orr helps runs an air conditioning company in Central Florida, and by night he’s a father of 9 -- yet somehow he's found the time to build his HVAC School podcast into a 5-figure a month business in less than a year.And it might sounds like an overnight success, but Bryan's actually been side hustling for quite a while, mostly in the podcasting and freelance audio production space.Tasked with training technicians at his day job, he had the idea to put it into an on-demand audio format, and that's where he found his side hustle sweet spot.It was on a whim he decided to publish the content online and make it available to a wider audience. “In the process it just exploded, I never thought there would be an audience like the audience that I found,” Bryan said.With 1000 downloads in the first 48 hours and synergy with his day job, Bryan started allocating more time to his show.As his audience grew he started negotiating sponsorship deals with large companies in the HVAC niche.Less than a year into this new side hustle, he's built an email list of over 7500 subscribers, generated more than 500,000 podcast downloads, and is earning $11k a month in sponsorship revenue.Tune in to hear how Bryan promoted his show to gain that initial traction, how he worked with influencers in his niche for extra exposure, and how he secured sponsors to monetize his show.Full Show Notes and PDF Highlight Reel: Finding Your Sweet Spot: How Talking About Air Conditioning Turned Into a 5-Figure a Month Side Hustle

“You have a skill, but you’re not using it correctly."That the tough love advice Vincent Pugliese's father gave him.Vincent was working what he thought was his dream job as a photojournalist. He'd just won the most prestigious award in his industry (International Sports Photographer of the Year), and he and his wife Elizabeth had a baby on the way.Yet the newspaper job didn't pay well. With the impending arrival of their son, Vincent took a hard look at his financial picture: he was in his mid-30s, 6-figures in debt, and earning $15 an hour.Not great.Something had to change, and something did.Four years later, the family was debt free and self-employed, thanks to the success of their freelance photography side hustle.I met Vincent at Podcast Movement and invited him on the show to share his inspiring and relate-able story. With a growing trend toward freelance workers, his transition is one many people will need to make over the next few years.With his newfound time freedom, Vincent has kept busy with a number of new projects including his upcoming book Freelance to Freedom, and an online course teaching parents how to take better sports pictures of their kids.(Even though Vincent had no "audience" of his own to sell to, the course did over $30k on launch day, giving us the hook for this episode.)Tune in to hear how he and his wife got it done and how you can apply the same strategies to the skills on your own resume.Full Show Notes and PDF Highlight Reel: Freelance to Freedom: From $30k a Year to $30k in a Day

Quit my job? “That’s stupid,” Kim Anderson said.But she eventually did, and it turned out to be a really smart move. Together with her husband Cressel, they paid off $93k in debt in less than 2 years, setting themselves up for a life of “financial flexibility.”They did it through a combination of conscious spending, creative side hustles, and having a clear goal in mind. And perhaps what’s more exciting is what that new time freedom has allowed: starting a family, starting new businesses, and most recently even “retiring” Cressel from his engineering job.In this inspiring episode, Kim and Cressel break down their path to financial freedom, which I think will get your gears turning on how to do the same.Full Show Notes: Your Escape Plan: How to Make Early “Retirement” a Reality

Would you trade $1000 for $2000? How about $10,000 for $18,000?If you're anything like me, I'll make those trades all day long!Well, Deacon Hayes is doing exactly that every month through his blog, Facebook ads, and affiliate marketing.Although he'd been blogging for years, his traffic and revenue had kind of stagnated.Inspired by the success of The Penny Hoarder using a similar strategy in a similar niche, Deacon decided to jump in and throw $1000 toward his new Facebook Ads experiment. Within a month he'd effectively doubled his investment.Ten months later he's built a beautiful machine that combines compelling helpful content, affiliate relationships, and the massive reach of Facebook.In this episode, you'll hear the type of content Deacon has found most profitable to promote, the types of ads he runs, and how he's able to get his costs per click down to around $0.05.Full Show Notes and PDF Highlight Reel: Facebook Ads Arbitrage: How to Drive Consistent Profitable Traffic to Your Blog

Dustin Lien from StrategicSauce.com reached out to me with an interesting pitch for an episode.Dustin had experienced a side hustle failure and wanted to know if the Side Hustle audience would be interested in hearing his story.I threw the idea out to the Side Hustle Facebook Group and received an overwhelming amount of feedback saying, “Yes,” they wanted to hear the “other side” of a side hustle when it fails.In this episode Dustin lifts the lid on a business he invested a large chunk of time and money into, only to pull the plug on it a year and a half later.He designed a great product that solved a pain point for people in the fitness community.So, what went wrong?Tune in to hear exactly what did and didn’t work for Dustin, and why he decided to throw in the towel on this project.Dustin shares what he would do differently if he had to start over, as well as what he's working on today. He's loaded with valuable insight for anyone starting a new venture.Full Show Notes and PDF Highlight Reel: When a Side Hustle Fails - Lessons, Pivots, and Next Steps from a Less-Than-Successful Side Project

Guest Christopher Gimmer, Co-founder of Snappa, shares how they bootstrapped Snappa to $33k MRR in 2 years. Topics include idea validation, successful launch, growth strategies, freemium model, user engagement, marketing tactics, and strategies for sustainable growth in SaaS companies.

Three years ago Design Pickle didn't exist. It wasn't even an idea in founder Russ Perry's head yet.That's why it seems crazy to me that today the unlimited graphic design service is doing $400k in monthly recurring revenue!Back in 2014 Russ was running a creative agency, but he started to hate everything about it. “I felt like I was in a prison of my own creation,” he said.By January 2015, he'd shut down his agency and started working as a freelancer. Not wanting to build a similar prison again, he sought out a different business model -- one with a simpler service offering that was designed to scale.From taking on a friend as his first client to now completing more than 800 design jobs a day, it’s been an incredibly quick ascension and a great example of how to scale a service business.Tune in to hear how Russ grew his business from zero to $410k+ in monthly recurring revenue in less than 3 years.We cover his marketing strategies, his hiring best practices, and what Design Pickle does to keep customers coming back month after month.Full Show Notes and PDF Highlight Reel: Scaling Up a Service Business: From Idea to $400k in Monthly Recurring Revenue (in Under 3 Years)

Zeona McIntyre is earning $12-18k a month through her portfolio of vacation rental properties and her "co-hosting" service for other property owners.All this has afforded Zeona financial independence at a very young age, as she built her operation largely by piggybacking on the growing popularity of Airbnb (get $40 off your first trip!).She first became aware of Airbnb and the potential to earn some extra revenue back in 2011. She was in massage school at the time, but a friend of hers in New York subletted his apartment on Airbnb to the tune of $50k for the year -- all while traveling full-time.“I couldn’t ignore it from then; I started right away,” Zeona said.She started by subletting a room in her apartment, then her whole apartment, and now owns five rental properties and manages or "co-hosts" another 15-20 properties on the behalf of her clients.With a small team, some smart decisions, and some online tools, Zeona now manages her business from her home in Boulder, Colorado relatively hands-off.This is the second episode in our recurring revenue series this month. If you missed last week, be sure to check out how a full-time cop built a subscription box service to $15k a month.This week, tune in to hear how Zeona chooses vacation rental properties, how she calculates the potential ROI, and how you can get started in this location independent side hustle today with just a spare room in your home.Full Show Notes and PDF Highlight Reel: How To Shortcut Your Financial Freedom with Short-Term Rentals

From the spare bedroom to $15k in monthly recurring revenue, Sam Gonzalez has grown the subscription style service UrbaneBox.com (affiliate link) all on the side from his day job as a police officer.He noticed his wardrobe was getting pretty outdated and with family and work life, he didn’t have any time (or desire, really) to go shopping. So he decided to do something about it and create an online subscription box business with a cool value proposition: $120 worth of designer clothes for $60.In this episode Sam talks through the steps he took from building his website, pitching suppliers, experimenting with different pricing models, and outsourcing the order fulfillment.He’s used a combination of AdWords, social media promotion, collaborating with other bloggers and YouTube influencers, and an interesting Facebook “hack” to rapidly grow his business.Tune in to hear how Sam went from idea to 6-figures in 3 years, from packing and shipping his first order from his spare bedroom to a business that now does $15k in monthly recurring revenue.Full Show Notes and PDF Highlight Reel: How to Start a Subscription Box Service: From Spare Bedroom to $15k in Monthly Recurring Revenue

It’s time to dive into the ol' listener mailbag and answer a few questions in this week’s edition of The Side Hustle Show.It’s been 6 months since the last Q&A show I did (where does the time go??) and I’ve had quite a few interesting questions come in since then. I picked 20 to talk through in today’s show.Like this format? This is the 4th installment of "20 Questions" so feel free to go back and binge on the older ones too: 219: Growing Traffic, Monetization, List-Building, a Day in the Life, and More: 20 Questions with Nick 198: Blogging, Branding, Book Writing, and Finding the Right Side Hustle for You: 20 Questions with Nick 181: SEO, Affiliate Marketing, Self-Publishing, Udemy, and More: 20 Questions with Nick A common piece of advice you’ll hear is to take audience questions and turn them into content, so here’s a meta example of that in action.This episode covers questions on affiliate marketing, audience building, network marketing, imposter syndrome, my income streams today, and my side hustle mistakes.Tune in to hear my responses to those questions and a dozen more below.Full Show Notes: Network Marketing, Imposter Syndrome, My Side Hustle Mistakes, and More: 20 Questions with Nick