The Side Hustle Show

On any given weekend in San Francisco, out of earshot from the barking harbor seals at Pier 39 and the clang of the cable cars, a small group of urban hikers are exploring the city from a different vantage point. For three hours, they walk, climb, and even slide their way through historic neighborhoods and scenic outlooks. They’re led by Alexandra Kenin, or one of her carefully selected guides, an...

Kara Lamerato is a work-at-home-mom of 2, but runs a successful business in her spare time. Kara's Vineyard Wedding supplies brides with wine-themed wedding decorations, and has shipped thousands of orders. Kara started the business before having kids while she was still working full-time in private banking. The idea came from her own wedding and thinking there might be other brides out there look...

Tom Morkes has worked on the book launches for a number of previous Side Hustle Show guests, including John Lee Dumas, Dan Norris, Taylor Pearson, and Neil Patel. What I wanted to do in this conversation was reverse engineer some of the steps that go into producing, launching, and marketing a bestselling book, even if you don't have thousands of fans waiting for it. And selfishly, I wanted to get...

Rachel Pedersen was using social media to bring customers to her hairdressing chair, but never really imagined it would turn into a full-time business of its own. One of her hairdressing clients owned a popular restaurant chain, but was struggling with online marketing and social media. Rachel offered to help and the rest is history. Today her little social media management side hustle is a 6-figu...

Dropshipping is also a topic we haven't really covered in depth in the past, but many listeners have been requesting to learn more about it. I reached out to Anton Kraly, who's one of the most successful people I know in this space. He's been selling online for almost 10 years and he and his team have built out an impressive portfolio of drop-ship stores. Dropshipping is where you sell a product a...

Matt is a former Air Force pilot who was looking into various side hustles to support his family after some salary cuts at work. After hustling and selling used books (among other things), he realized it really wasn't sustainable and took up too much of his time. That's when he found a gumball vending machine for sale on eBay for $36. The seller was local in Houston so he drove over with two of hi...

Before people can do business with you, they have to know about you, and before they know about you, they have to find you. And that’s universal, whether you’re running a brick-and-mortar shop, an ecommerce store, a blog, or a virtual consulting business. Neil Patel is a master at solving the first step in that equation: getting people to find you. Through SEO, content marketing, and social media,...

Dan Harris had me at "meditation for skeptics." In the last 5 years, it seems like meditation has gone from a weird woowoo practice to a daily staple of most top entrepreneurs, executives, and leaders. But so far, I haven't been able to get into it. Have you? I've tried a few of the guided meditation apps, including Headspace and Calm, but when I tried meditating in the morning, I had this impatie...

Eight years ago this month I pulled out of the parking lot of my corporate job for the last time. It was a weird moment, filled with hope and excitement, but also nervousness. Sure, I'd built my side hustle to the point I was comfortable taking the leap, but it was still a leap. The responsibility of cutting your own paycheck each month is stressful! In this episode I attempt to pull out 8 of the...

Teaching what you know in the form of an online course has become the bread and butter for many online entrepreneurs. You can see the appeal: package all your best stuff into a logical and well-presented lesson plan, record it, and sell it over and over again. Course creation has the potential to be a fantastic passive income business, just like book sales or software. Build an asset that has low-...

Last fall, Chris Deardorff had a passion for startups and entrepreneurship, but wasn't sure which direction to go. He had -- and still has -- a good job doing product marketing. But as he studied the local startup scene, he noticed a common problem. Many startups struggled to gain traction for the products and services; a problem an experienced product marketer could solve. In this episode, you'll...

As you know, I'm excited about alternative investments like peer-to-peer lending. And if your aim is to replace your income, I think it makes sense to invest for cash flow. This week's Side Hustle Show guest argues when you want something in other areas of your life, you go out and buy it: a pair of shoes, a computer, a new car. You don't make it from scratch! So why are we so insistent on buildin...

It's time to dive into the ol' listener mailbag and answer a few questions in this special Friday edition of The Side Hustle Show. The last Q&A show I did was back in November and I've had quite a few interesting questions come in since then. Today we're chatting about SEO tools and strategies, affiliate marketing, self-publishing, Udemy, real estate, taxes, consulting, and more. Full Show Notes:...

Scott Tarcy reached out to me with a listener success story of taking some of his on-the-job skills and turning them into a business on the side. Scott's a mechanical engineer by trade, and his job involved lots of product design work, including computer aided drafting and 3D modeling. Recognizing that other individuals and companies might have a need for those skills, he took to the interwebs. Fu...

More than 150,000 women have completed Tiffany “The Budgetnetista” Aliche’s Live Richer Challenge. The roughly 30-day challenge participants step-by-step instructions on how to get their financial lives in order, get out of debt, and start saving money. Collectively, Tiffany’s tribe has saved $17 million and paid off $1.5 in debt! I first heard Tiffany tell the story of how she started the challen...

Darrel is a full-time Operations Manager for a startup in Atlanta, but has built a sizable side hustle on eBay. In the last 12 months, he's sold over 6-figures worth of merchandise. eBay still gets massive traffic; it's currently the 7th most popular site in the US and 26th most popular in the world. That's a lot of eyeballs, and more importantly, that's a lot of buyers! In this conversation, Darr...

At the end of nearly every episode of The Side Hustle Show, I ask my guests for their #1 tip for Side Hustle Nation. There’s always a great variety of responses, and I wanted to take some time today to go through some of my favorites from the past 50-ish interviews. My #1 Tip? Find your WHY. Why side hustle? What are you trying to build? What will that afford you? Full Show Notes: What I’ve Learne...

Matt Inglot was following the hustler's path. He built some skills on his spare time, and began selling those skills as a freelancer. The first project he sold was to build a website for $300. Soon, he had a full-time freelance business, and decided to grow into an agency. But before long, Matt found himself working 80 hour weeks and stressed out during down months about covering rent and payroll....

If you want to learn English, you may have come across one of Gabby Wallace's hundreds of YouTube videos on the subject. Her channel, which started only because the video she recorded for her classroom students was too big to email, has grown to more than 170,000 subscribers and nearly 9 million views. Gabby is a long-time teacher and found a way to turn her subject matter expertise into a busines...

Jesse Gernigin is a professional stage hypnotist and online freelancer. He used to do up to 200 shows a year and even sold his own products, but realized there was always going to be a ceiling to his earning power. Turning to the world of online work, Jesse applied his performance and sales skills to land freelance work in his spare time. Today he specializes in copywriting for email sequences, sa...

"To build income you can hustle, but to build wealth you need to build something that doesn’t require your hands." That's what this week's guest told me, and then walked me down an interesting path in building that elusive "hands-free" business. His angle? Product licensing. Full Show Notes and PDF Highlight Reel: How to Turn Your Ideas Into Recurring Revenue, with Stephen Key

Carey Green had spent the last 20 years as a pastor, before making the leap into entrepreneurship. As he studied to become a licensed mortgage broker, an idea took hold to put his study notes online. Today Carey helps other aspiring mortgage brokers pass their certification exam, a test he says was the hardest he ever took. That business, which actually derives most of its traffic from YouTube, ge...

Want to get paid to create content? Jason Zook is the undisputed king when it comes to sponsored content. You may know Jason as the IWearYourShirt guy, where he earned over $1,000,000 wearing t-shirts for various companies. He's even sold his last name (twice -- each for $40k+), formerly going as Jason Surfrapp and Jason Headsetsdotcom. In this episode, he shares his tips for getting sponsors for...

In my recent annual member survey, one of the biggest challenges named was coming up with the right side hustle idea. Over the years, I've been on both ends of the idea spectrum: feeling hopeless in search of a business idea, and (more recently) feeling like there are more ideas than I could ever hope to tackle. Still, if you're in the brainstorming stage, I think this week's podcast session with...

This is the second in what will (at least) be a 2-part series on side hustlers earning income from their land investment endeavors. In this special Friday edition of the show, I'm joined by Chris Pritchard. Chris is a software developer by day, but has built his land investing business up to $1500/mo in recurring revenue. In addition, Chris does the occasional cash flip and also has more than $70,...