How Sean Kelly turned a dumpster dive into a TV dynasty

Plus, do this, and you'll never ever worry about money again


Right when his feet slid down the inside wall of the second dumpster, he saw them.

Sean Kelly’s face lit up because he’d just hit the jackpot. He and his Army buddy would eat tonight after all.

The whole thing started with a long weekend pass. 19-year-old Sean had no plans. When his buddy said, “Hey, you wanna play an entrepreneur game with me this weekend?” First, Sean asked, “What does entrepreneur mean?” Then, “Um, what’s involved?”

The rules were simple.

  1. We leave the barracks at Ft. Devens with nothing but our IDs and the clothes on our backs on Friday morning.

  2. We come back Monday night.

Sean had questions. Good questions. Questions like: How are we gonna eat? Where are we gonna sleep? That’s when his buddy knew Sean was getting the picture.

“We’ll go out and see how much money we can make, starting from scratch,” his buddy said. He seemed so excited. Plus, this was a Special Forces guy. It sounded fun.

And so, they went. 

As Sean slid feet-first into the first dumpster, the adrenaline kicked in when he saw exactly what he’d hoped to find.

This week, wildlings, I’m delighted to introduce you to Sean Kelly (you might remember him from Storage Hunters, which ran in a few iterations for a decade between its stints in the US and the UK.

From newspapers to stand-up to raising half a BILLION in charity auctions and helping people reach their biggest, baddest, most ambitious dreams, Sean can point to one particular conversation that changed his entire outlook and made it all possible.

You’ll hear all about it in this edition of Entrepreneurs Gone Wild. That, and you’ll learn how to use some very specific outdoor time to give your brain undeniable proof that YOU never have to worry about money again.

But first…

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OK. Where were we?

Oh yes. Sliding into a dumpster. In Massachusetts. 

In Massachusetts, you can get 10 cents for every can and bottle you take to a recycling center. It’s not a particularly sweet-smelling way to make money, but it was perfect for our soldiers that long weekend.

They redeemed what they found, got some money, then hired a guy from their unit who had a VW bus to drive them around to find more. 

That’s when they found their next little pile of money. Someone had thrown out their CD collection. Someone else, a bunch of uniforms. A trip to the record store (yeah) and the Army Navy store gave them more cash. 

They bought a Polaroid camera, film, and train tickets to Boston, where they camped out in front of the Cheers sign. All night long, they sold Polaroids to a steady stream of tourists. No cell phones back then - this was the OG way to get your picture in front of a famous landmark… for $5 each.

Now they could rent a hotel room for the night and sleep in a comfy bed. They could but they didn’t. Instead, they went to Dunkin’ and bought coffee. They chatted with the lady behind the counter, told her what they were doing, and asked if they could sleep in a booth. Good deal for her - way safer to have a couple of buff Army guys sleeping there than to be alone overnight.

The next day, they awoke with sore backs and a bunch of cash. The guys looked for a way to reinvest and found a guy selling  I ❤️ Boston shirts cheap. Like, $1 each - enough to stuff a taxi cab full of them… which they sold by the Cheers bar, an upsell to the Polaroids.

By the time they went back to the barracks, their pockets were $3,500 heavier than when they left. Even more glorious, Sean now KNEW he’d always be able to make enough money to live on. He could lose it all, and make it all back.


Growing up, Sean probably dreamt of Zig Zigler’s voice. His dad was selling insurance and often took Sean along to collect lead cards. Riding in the car, they’d listen to Zig on cassette tapes. On repeat.

It stuck. Soon, his winning mindset got a major tweak.

Sean was a competitive skier in high school. Swooshing down the slopes one day, he had no idea he was being watched. 

You see, there’d been a misunderstanding, as Sean was about to discover. The guy watching him was a little worried. Sean was fearless and fast. This guy wasn’t sure he could beat Sean. So he started chatting him up. They hopped on the chairlift together to continue their conversation. When the guy figured out Sean was a high school kid who was not, in fact, there to kick his butt in a race, he asked Sean the question that would change his life.

“So, you’re on the ski team. Do you win races?” When Sean said no and started explaining why (his family couldn’t afford… much, so he was using rented equipment and wore sweats and a big floppy coat), the guy shushed him. 

That’s where this got GOOD. 

“You need to quit making excuses for all the reasons why you can't win. You need to start telling yourself all the reasons why you can't lose and why you have nothing to lose. Because here's what you need to understand… 

What you sell to yourself is what you will buy.

And what you buy is what you will sell to the world - and they will buy that from you. What you sell and what you buy, you buy, you actually believe it, you buy it. So if you believe that you're a winner, if you believe you can't lose, everyone else is going to believe you're a winner and that you can't lose.

That guy on the ski lift? Kinda famous. Billy the Kid. The Olympic skier.

His words hit. Sean lived those words. It was those words that led him to make a major announcement at his birthday party years later… an announcement that changed his path forever.


When you turn 40, sometimes you start being much more aware of time passing. You start remembering dreams you’ve shelved for later. Start taking some of them off the shelf “before it’s too late.”

Sean’s friends got that. So they were super enthusiastic in their response. “Wow! What channel? What’s the show? What’s it about?”

Sean’s answer: I dunno. Yet.

But he also knew that everything… EVERYTHING… begins with an idea. And before long, he had a doozy of an idea. The story of how he got his first show on TV is one of sheer tenacity. He called people he “shouldn’t” have called, pitched over the transom like it was his job. His wife, bless her, was all-in. She’d seen Sean pull off some epic stuff and had no doubt he’d do it again.

That’s when it all started coming together. 

For years, Sean ran a newspaper in San Diego. Within 36 months, he’d taken it from $3M a year to $26M a year. On the side, he’d started doing stand-up comedy at a club he started off-hours at a Greek restaurant. He got good.

So, when a buddy who owned a storage facility invited Sean to give auctioneering a shot - you can see the potential, right? - Sean did, filling in to cover a charity auction. Soon, he hired a world-famous auctioneer to teach him his fast-talking ways. (Turns out an auctioneer coach just teaches his craft at a normal rate of speech… you have to practice to get Jim Dickens of Letterkenny-fast.)

Now he had a real concept to pitch. truTV bought Storage Hunters and ran it for six years. When they were done with it, Sean was not. So, he pitched the British channel, Dave, and the UK version of Storage Hunters began its run there. Then it morphed into Charity Storage Hunters, and then Celebrity Storage Hunters. From zero experience and zero contacts in a cutthroat industry, to a total run of 12 years on TV… that’s a big freaking deal.

To date, Sean has raised half a BILLION for charity. 

But he’s not done.


If there’s one single question Sean gets asked, it’s this: How did you do that?!

So, he’s started “Do the Big Dream” to help people who’ve got a big, lifelong dream. Maybe they don’t know how to get started. Maybe they’d just about given up on it - and now they’re realizing they’ve GOT to go for it so they don’t forever regret not going for it.

Looking back at his life, all the hours of listening to Zig Zigler, becoming impervious to rejection while helping his dad sell insurance, the Billy Kidd encounter, the whole amazing Storage Hunters experience… now Sean had something POWERFUL.

He’s distilled his experience and wisdom into 15 steps, which he’s sharing via Do the Big Dream. And you’re invited! The Facebook group is free, and Sean’s kicking it all off in early February. (I couldn’t join fast enough… building an entrepreneur starting at age 56? Sounds like the perfect Big Dream to DO!)

Of course, I had to ask Sean how his time outdoors has impacted his life. There was all that door-to-door sales as a kid, his time on the ski slopes, his time playing the Entrepreneur Game in the streets of Boston… but how about now? 

Sean’s a walking man. He and his wife love to travel, and when they do, they walk and walk and walk and walk. It’s one of the best ways to explore a new place - you see stuff you’d miss on wheels. 

“When you're out walking and you're breathing, getting that fresh air, your mind gets going,” he says. Clearly, based on results, this guy does a LOT of walking. He’s got a standing invite to come do some of that at Idyllwild Woods. (And so do you!)


(Shout-out to some of you, who went through a certain personal development program with me… I know you just had some flashbacks with that question.)

Imagine never worrying about money again. 

Sounds too good to be true, right? But what if a simple game could unlock that confidence in you? 

Yup. The Entrepreneur Game, just like Sean played. It’s a DIY real-world challenge that could revolutionize how you think about money, business, and survival. 

The Game: Start from Scratch

The rules are simple yet daring. You leave your home with nothing but your ID and the clothes on your back. No money, no credit cards – nothing. Your mission is to see how much money you can generate from absolute zero. You can’t return home until the set period is over – be it a weekend or a week.

Rules and Guidelines:

  • Survival is Key: Your first goal is to secure basic necessities – food and a safe place to sleep.

  • Be Resourceful: Look for opportunities in everyday situations. Dumpster diving? Selling found items? All fair game.

  • Stay Legal: All money must be earned legally and ethically.

  • Innovation is Your Friend: Constantly think of new ways to generate income.

  • Safety First: Always consider your safety and well-being.

This game isn’t for the faint-hearted. It’s a raw test of your entrepreneurial skills, creativity, and resilience. It's about making something out of nothing, relying solely on your wits and resourcefulness.

Sean’s story is a testament to what’s possible. Starting with dumpster diving, evolving to selling Polaroids and T-shirts, he turned zero into $3,500 in just a weekend. His journey is proof of the untapped potential within each of us.

Now, it’s your turn. Are you ready to take on the Entrepreneur Game? 

This could be the beginning of a new understanding of your abilities and potential. Remember, it’s not just about making money; it’s about discovering that you can survive and thrive, no matter what.

Take the challenge. Step out of your comfort zone. You might just surprise yourself.

You guys, this time tomorrow, hubby and I should be the proud owners of a brand-spankin-new metal pole barn. On a brand-spankin-new barn pad, at the end of Idyllwild Woods’ brand-spankin-new gravel driveway.

I’ll have visions of alpacas and highland cows dancing in my head tonight.

Thanks for being here from the start of this journey. Every page I read of this book makes me think of you and all the cool stuff I want to build for you.


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