Build a Lifestyle Business Giving You Freedom You've Always Wanted

Our 6-part course gives you a strategy to start right now. Put control of your life back in your hands. Sign up below and let’s do this together.

By entering your email address you agree to receive emails from Location Rebel. We'll respect your privacy and you can unsubscribe at any time.

How to Turn a Hobby into a Hustle (7 Unique Strategies)

by Guest Post | Last Updated: April 10, 2018

Note from Sean: This is a guest post from Dan Pierson. I love what Dan is doing with Bolt Collective. and we share a lot of similar interests when it comes to building businesses around things we love.

I was pumped when he asked if he could share some tips and stories from his own experiences, so if you’ve been thinking about building a brand around a hobby or interest – pay attention!

Take it away, Dan!

I’ve spent a lifetime turning side projects into businesses, with a lifetime of learnings from successes and failures along the way.

I’m lucky to have somehow fallen into work that keeps me focused, fulfilled, and stoked on life, and (after a lot of trial and error) pays the bills at the end of the month.

Over the past 10 years, I’ve:

And that was all before my new venture, Bolt, which takes a decade of planning travel for friends and family, and pours those lessons into a community that uses collective purchasing power to unlock otherwise impossible travel experiences like chartering a fleet of catamarans and sailing through the British Virgin Islands.

Dan Pierson

When Jetblue cancels your flight from Puerto Rico to Saint Thomas…sometimes you have to charter your own plane.

So with three “passion projects” under my belt, and this latest venture underway, it’s a great time to stop and reflect on a few key takeaways.

1. You Don’t Need to be an Expert to Enter the Marketplace

By nature, I’m a dabbler; I think it stems from my short attention span. I like to try a million things, but never seem to focus on anything long enough to reach mastery.

Growing up, this frustrated me tremendously, as I watched friends excel at guitar, become Olympic snowboarders, and reach levels of fitness I could only dream of.

In my thirties, I increasingly realize the importance of breadth, alongside (or even in the place of) depth. That’s because the vast majority of your audience won’t be experts, either.

They’ll be everyday enthusiasts, just like you, and that means you’ll understand their needs, and how to bring them value.

Lesson: Silence the inner critic – you have all the competence you need to take this step.

2. Ask Yourself: What Unique Skill Set do You Bring to Your Hobby?

Can I tell you how much I LOVE Sean’s “The Eighty Club” golf travel community? It’s not because I’m a golfer – I haven’t picked up a club in 10+ years. Instead, I’m excited by how he applied his skill set to find ways to get even more pleasure out of his hobby, off the course.

By Sean’s own account, he’s a solid golfer, but no Tiger Woods. His athletic prowess isn’t what has turned his passion for the links into a six-figure business.

Instead, he focused on what he’s really, really great at: creating dynamic, insightful content, nurturing vibrant online and offline communities, and then building a thriving enterprise around the momentum he’s created.

Lesson: The hobby itself is just the beginning. The value you create in the marketplace will come from how you apply your unique talents and insight.

Build a Lifestyle Business Giving You Freedom You've Always Wanted

Our 6-part course gives you a strategy to start right now. Put control of your life back in your hands. Sign up below and let’s do this together.

By entering your email address you agree to receive emails from Location Rebel. We'll respect your privacy and you can unsubscribe at any time.

3. Dig into the Difference – What Sets Your Approach Apart?

There has literally never been a better time to turn your hobby into an income – ease of access to capital (Kickstarter, Indiegogo, Stripe), powerful, simple tools (Shopify, Squarespace, etc), and an audience (the good people of the Internet) has never been more available.

But you’re certainly not the only one to realize it, so you need to concentrate on amplifying your signal, to rise over the noise. What makes your offering different from the crowd?

While I loved going to shows, the thought of promoting music was TERRIFYING – in a place like New York City, there are literally hundreds of concerts happening every single night, which means the talent is basically a commodity.

But I had a secret weapon, marketing my unique concept – Subway Sets, which takes New York’s best underground music up to rooftops above the city. So instead of trying to present regular musicians at regular music venues, our refreshingly different angle allowed us to gain crucial early momentum.

Here’s an example, and a huge milestone: Queen Latifah’s producers found the project on Kickstarter and flew me and one of the Subway Sets musicians out to LA for an interview and performance on her (sadly, since canceled) daytime talk show.

Dan Pierson Queen Latifa

Me and the Queen. We are glowing in this photo.

Lesson: Your hobby may be the most popular pastime in the world, but I guarantee you there’s an angle or twist that hasn’t yet been explored. What’s your “hook”?

4. Look for (or Create!) the Catalyst to Turn Your Hobby into a Hustle

In each business I’ve started, I can point to a specific moment that provided the catalyst to step up and start.

I’ve always loved writing, and during college, I moonlit after class, creating web content, blog posts, and articles to pay for beer money (I went to school in New Orleans, so you can imagine that beer money wasn’t exactly a cheap proposition).

Freelancing was a great way to dive into the early days of content marketing, but even at a young age, I knew I wanted more.

Right after graduation, I moved to Argentina, and in my first few days stumbled into an expat party. As I circled the room, meeting underemployed English teacher after underemployed English teacher, I realized I could provide all of these talented, college-educated Americans with steadier, higher-paying work, creating the same kind of web content.

Within six months, I’d turned freelancing into an agency, signed a six-figure contract, and we were off to the races.

I would never have thought moving abroad would give me the opportunity to work with Inc. 500 corporations in the United States, while at the same time fulfilling dreams like riding a bicycle around the North and South Islands of New Zealand.

Dan Pierson New Zealand

A much younger Dan, living the Location Rebel lifestyle in New Zealand.

Lesson: Spend time with folks who share similar interests, and keep yourself open to the universe.

5. Experiment on your Friends and Family

Think of your friends and family as guinea pigs.

These people want to support you. Every time you’ve backed a Kickstarter, donated to a GoFundMe, heck, when you’ve just “liked” a Facebook post – you’ve added to your piggy bank of goodwill. So when you’ve clearly put your passion, thought, and hard work into putting something out into the world, these people will be THRILLED to see you succeed.

I didn’t realize it at the time, but with each trip I planned for family and friends, I continue to build my travel production muscles. After years of success (and quite a few mishaps!), those muscles became strong to the point where I felt totally comfortable putting using them for complete strangers – and voila, Bolt Collective was born.

Dan Pierson

Little did I know this “friends and family” NYE sailing trip would be a key step in the journey towards starting Bolt.

Lesson: Your friends will overlook early mistakes, and that’s key because you’ll make them – guaranteed.

6. Get SOMEONE to pay you for SOMETHING

Every single article you read about starting a  business will tell you this, but it’s so crucial that it bears repeating again: your hobby is just a hobby, until you get someone to pay you for it. I’ve talked about a few successes along the way. Here’s a huge failure.

With SlingShot, I spent an entire year building a fancy product before earning a single dollar in revenue. I had people using it, and I kept telling myself people were spending so much time using our tools – eventually, once they were robust enough, we’d get folks to pay for them. Nope.

On the Internet, people will give you time, but it’s much, much harder to get them to pull out their wallet. Once they do, regardless of what they’re actually paying for, you’ve found a valuable offering – even if it’s only a stepping stone on the way to your final product. Rome may not have been built in a day, but you can bet they were collecting taxes from the very beginning.

I know this is Sean’s gospel, and for good reason. Check out his recent article “14 Ways to Make Your First Dollar Online” – it has plenty of tips for getting those dollars EARLY.


7. Wait Forever to Hire…Then Wait Some More

Painfully difficult to type this story, but here goes: hiring the wrong virtual assistant cost me $15,000, and almost sunk my agency.

The contract with our biggest client included posting thousands of pieces of content on article directories each week. Our project manager was managing a virtual assistant, who was, in turn, managing another virtual assistant – you can likely see where this is going.

That last contractor flaked, the articles didn’t get posted, and we ended up eating tens of thousands of dollars and almost losing our most important relationship.

Sean runs a very successful business with the help of his excellent community manager Liz, and I imagine their Asana dashboard is pretty succinct and to the point. As ambitious entrepreneurs, our instinct is to grow, grow, grow. But you can often reap the same rewards by keeping things simple.

Lesson: Resist the urge to add headcount.

It’s Time to Get Going

I started this post by telling you that expertise is overrated. That was a white lie. I want you to become an expert in STARTING, and I can’t wait to hear how it goes.

Here’s to a successful 2018, turning your hobbies into hustles!

Dan Pierson is the Founder of Bolt Collective, an experiential design consultant for companies like Airbnb and the Rockefeller Foundation, and the creator of Subway Sets, a concert series bringing the best musicians from the New York subway up to rooftops above the city. In past lives, he’s ridden a bicycle across the United States and New Zealand, walked across Cuba, and hiked 227 miles in the Sierra Nevada along the John Muir Trail.

Build a Lifestyle Business Giving You Freedom You've Always Wanted

Our 6-part course gives you a strategy to start right now. Put control of your life back in your hands. Sign up below and let’s do this together.

By entering your email address you agree to receive emails from Location Rebel. We'll respect your privacy and you can unsubscribe at any time.