As a builder and unconventional entrepreneur, I’ve learned that one key to success is adding value to others. Join the community that understands the power of giving first, learning from our mistakes, and always asking, “How can I help?” Explore building side hustles and successful businesses that lead to living an uncommon life.
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Unconventional Entrepreneur
Shannon Jean
I am a paid professional Surfer.
Kind of.
I’ve made millions surfing trends and opportunities for the past 25 years.
Here are the waves I’ve surfed:
Youth –
When I was a college kid, older people were impressed with my hustle and ambition. “Look at that kid go!” It opened doors and thrust me into roles that put me years ahead of my competition.
The Long Game –
While I was hiring my college buddies to work for my landscape construction business, I realized they were focused on weekly cash so they could live large on the weekend.
I was focused on how much cash I could make over the 3-month summer break so I wouldn’t have to work the rest of the year. I would take $30-$50K back to school by not spending anything during the summer.
This Long Game thinking helped me when I started other companies. By fighting lifestyle creep, I was able to invest in more companies and in my family's education and experiences.
Over 20 years, I pulled back this slingshot of frugality so far that when big deals hit in my 40s, it exponentially upgraded our lives beyond anything I had imagined.
The Dot Com Boom
I owned technology companies as the world first embraced the Internet and e-commerce. We rode this wave to the peak as companies like Pets.com and Webvan reached new heights.
The Dot Com Crash
As companies like Pets dot com and Webvan imploded, I learned how to buy liquidation assets.
The amount of inventory available for pennies on the dollar was staggering.
This was about the time I caught the auction fever that would impact my life and my businesses for decades ahead.
Apple Almost Dying
I started my first tech company because I fell in love with the Mac. I was too young to understand what was wrong with Apple, but old enough to take advantage of their massive inefficiencies and failures to build a very tall Revenue Stack.
I’ve told the stories here before about poorly designed laser printers making us millions and over-stuffed inventory channels creating unbelievable opportunities.
SPONSOR POSHMARK UNLOCKED
Most people see Poshmark as a side hustle—I saw it as an opportunity.
I am handing you the exact playbook that took me from casual seller to four-figure months. No fluff, no guesswork—just proven strategies to help you:
Find profitable items (even if you don’t have inventory yet!)
Create listings that sell fast
Price your items for max profit
Automate the process so you can make sales in your sleep
Don’t waste time figuring it out alone—get the blueprint and start making real money today. ~ Shannon
Apple Rising from the Dead
When Steve returned and launched the iMac, then the iPod, iPhone, and iPad – we were seasoned and credible enough to enter those markets quickly.
We surfed higher than ever before as Apple took the world by surprise and created products everyone had to have.
The Trade-in Cycle
We started BuyBack+ when the phone upgrade cycle was a yearly flywheel.
It flooded our warehouse with profits disguised as smartphones.
The Airbnb Boom
I always wanted to own homes in places I enjoyed visiting. Being able to rent out to guests while we weren’t there allowed us to cover the bills and create six-figure profit businesses in the process.
The Airbnb Bust
Because we paid cash for each of the homes we purchased, we just rode the wave back down to a lower level when the inevitable oversaturation and municipal backlash occurred.
But we kept on surfing.
Age
I’m no longer the “go kid go” guy. But now that I get to tell my stories in reverse, it attracts an entire new generation of Entrepreneurs who want to learn from my mistakes and successes.
My gray hair also helps.
I know more waves helped us create the fantastic and uncommon life we lead, but I think you get the idea. Need help finding your next wave? Hit the “How I can help you” section below.
As a builder and unconventional entrepreneur, I’ve learned that one key to success is adding value to others. Join the community that understands the power of giving first, learning from our mistakes, and always asking, “How can I help?” Explore building side hustles and successful businesses that lead to living an uncommon life.