Change or Die: Lessons from Billion-Dollar Entrepreneur Josh Chodnowitz
“Everybody is missing something in life. I felt prisoner to my own success. Change is hard. Change is hard. I get it. Change or die.”
I said those words because I believe them to my core. Change isn’t optional—it’s the price of admission if you want to play the game of entrepreneurship. And nobody embodies that truth quite like my friend Josh Chodnowitz.
If you’ve ever wondered whether you’re “too ordinary” to build something extraordinary, Josh’s story is proof that the best entrepreneurs often start out sweeping construction sites for 25 cents an hour.
Let me tell you about the man who sold $2.8 billion worth of art online—and who’s now helping everyday people invest like the wealthy.
From Trash Collector to Billion-Dollar Business
Josh didn’t roll out of Harvard with a trust fund. He grew up in New Jersey as the oldest of seven kids in a family of Argentine immigrants. His first job? Cleaning up trash on his dad’s construction site for a quarter an hour. He learned early that if you want something, nobody’s handing it to you.
When the Internet was still just a rumor on college campuses, Josh’s buddy Mike Marston called him up and said, “Hey, there’s this thing called the Internet. People are gonna buy stuff there someday.”
So Josh did what real entrepreneurs do: he bet on uncertainty.
He and Mike scraped together $35,000—mostly borrowed from family—and launched a business selling art online. They had no business degrees. No fancy investors. Just grit and an instinct that the world was about to change.
They pitched dozens of investors who all said the same thing:
“What’s the Internet—and why would anyone ever use it?”
But Josh kept pushing. He and Mike sold their first poster…then their second…and eventually, they built AllPosters.com and Art.com into companies that shipped truckloads of products every 45 minutes.
The Danger of Perfection
Here’s the lesson most entrepreneurs miss: if you wait until your product is perfect, you’ve already lost.
Josh shared one of my favorite stories: the pottery class analogy. Half the class was told to make one perfect pot. The other half was graded only on how many pots they made, quality be damned.
Guess which group produced the best work? The one churning out hundreds of imperfect pots. Because repetition beats perfection every time.
At Art.com, Josh tried launching a “perfect” custom framing service designed entirely by professional designers. Guess what? Nobody bought it.
But when they pivoted and let customers design their own frames, sales exploded.
“People say they want things…but you don’t really know until they’re willing to open their wallets.”
Amen, brother.
Success Doesn’t Mean Easy
Fast forward. Art.com grew to over 23 million customers and almost $3 billion in sales. You’d think it’d be smooth sailing from there.
Nope.
Success brought new headaches. Layers of management. Hundreds of employees Josh barely knew by name. Investors who wanted their own vision realized instead of his.
Eventually, Josh knew it was time to leave his own company—a decision every founder dreads. Because once you build your dream, walking away feels like amputating a limb.
He took some time off. But entrepreneurs never stay idle for long.
Democratizing Startup Investing
After investing in dozens of startups himself, Josh faced a new question from his sister:
“How do I get in on these opportunities?”
She wasn’t a billionaire or a venture capitalist. She was just someone who wanted a shot at the same 27% returns the ultra-wealthy were earning in private markets.
And that lit a fire under Josh.
Why should regular people be shut out of the asset class that creates so much wealth?
So Josh built Fundify, an investing platform that lets anyone—yes, even with just a dollar—to invest in startups vetted by experts.
Fundify does all the heavy lifting:
Screening thousands of startups
Negotiating the best terms
Pooling investor money so you can get in for as little as $1 a month
Instead of waiting for billionaires to scoop up the next unicorn, you get a seat at the table.
Keep Sticking Your Neck Out
Josh’s journey is a masterclass for entrepreneurs:
✅ Start even if it’s not perfect.
✅ Don’t wait for certainty—bet on where the world is going.
✅ Be ready to evolve, pivot, and reinvent yourself.
✅ Think bigger than your own story.
So if you’re feeling stuck, or waiting for “the right time,” remember Josh’s words:
“If you launch a perfect product, you probably launched it too late.”
Be bold. Be curious. Be patient.
Keep sticking your neck out—and you’ll see paths others can’t.
Interested in investing alongside Josh? Check out Fundify.com or find the app in your favorite store.
Until next time, keep reaching higher.
— Chris Jarvis
P.S. If this episode resonated with you, you’ll love my Be the Giraffe book.
