The Propeller – I need your help with something… – 10-19-2025

I was listening to Peter Thiel on the Rick Rubin podcast the other day…

And he said something that’s been rattling around in my head ever since:

“Hard doesn’t always mean useful.”

In other words:
Just because something is difficult doesn’t mean it’s the right thing to be doing.

Difficulty isn’t a reliable indicator that you’re on the right path or creating something valuable.

And I couldn’t help but think about my own life.

There were times I chased hard things just because they were hard.

For example, early in my career, I spent months trying to master a programming language that was “hot” at the time. It was brutal with late nights, endless tutorials, but in the end, the language fell out of favor, and all that effort didn’t move the needle for me. Hard? Yes. Useful? Not really.

Same with investing. I once dove deep into complex options strategies because they seemed sophisticated. It felt like the “hard stuff” would give me an edge. Instead, I burned time and money learning lessons I could have avoided by sticking to simple, proven principles like index investing. The hard path wasn’t the valuable one.

Even outside work: I remember obsessing over a personal project that required insane logistics and thinking the difficulty made it meaningful. Looking back, the stress wasn’t worth it. The project didn’t change my life. It was just… hard.

The pattern is clear:
Hard things can feel virtuous, but they’re not automatically important. In tech, the temptation is huge, chasing complexity for its own sake. In investing, it’s easy to think the most complicated strategy is the smartest (Investment advisors portray and convince people that investing is difficult and you need to pay them to handle your money). But often, the real wins come from clarity, simplicity, and focus, not from grinding through unnecessary difficulty.

So now, when something feels hard, I ask:

Is this hard because it’s valuable, or just hard because it’s hard?

Imagine walking into a room where five of the world’s most successful investors are waiting to judge your idea. You’ve built something you believe in. You’ve poured sweat and late nights into it. And then, one by one, they all say no.

That’s exactly what happened to Jamie Siminoff, the founder of Ring.

The Problem That Sparked a Revolution
Jamie was tinkering in his garage, inventing things, when he kept missing package deliveries. A simple problem. But no simple solution existed.

So, he built one: a doorbell with a camera, letting you see who’s at your door from your phone. He called it DoorBot. Sold a few hundred units. Then a few thousand. But scaling required serious capital.
 

The Shark Tank Rejection
Jamie applied to Shark Tank, thinking this was his big break. He pitched. The sharks listened. They tested the product. Then came the verdict:

Kevin O’Leary: “One of the worst products I’ve ever seen.”
Mark Cuban: “Market’s too small.”

All five sharks passed. Zero dollars. Zero deals. Millions watched him fail on national TV.

Most people would have quit. Jamie didn’t.

What He Knew That They Didn’t
The product wasn’t bad. The timing was early. People weren’t ready, yet.

So, Jamie kept building. He renamed DoorBot to Ring (branding matters!). Improved the tech. Made it cheaper, easier, smarter. Sold direct to consumers. Slowly built a loyal base.

Then the world changed: crime rose, package theft spiked. Suddenly, Ring wasn’t a luxury—it was a necessity.

The Tech Behind the Triumph
Ring wasn’t just a camera. It was IoT meets security. It leveraged cloud storage, mobile connectivity, and later AI-driven motion detection. It turned a doorbell into a smart home hub.

This wasn’t just a gadget; it was the start of the connected home revolution.

The Billion-Dollar Payoff
Sales exploded. Investors lined up. By 2018, Ring was pulling in hundreds of millions in revenue. Then Amazon came calling—and bought Ring for over $1 billion.

The same product Kevin O’Leary called “the worst ever” became a household name.

Today, Ring is in millions of homes, redefining home security.

The Lesson Every Innovator Needs
Jamie’s story proves:

Being too early looks like being wrong.
Expert opinion is just opinion, not fact.
The market decides, not the critics.

What idea have you abandoned because someone said no? What product is sitting in your garage because an “expert” didn’t believe?  Reach out to me and let’s talk about it!

Jamie turned five rejections into one of the biggest wins in tech history. Why? Because he understood:

No doesn’t mean never. It means not yet.

Stop letting experts define your future.

Build. Test. Iterate.

Work through the rejections until the world catches up.

Because sometimes, the worst pitch on Shark Tank becomes the billion-dollar exit.

Think big. Build bigger. And when the sharks say no, remember—the market might say yes.

I’m sure all drug dealers and thieves report their income!  

Stay bold, stay curious, and never stop shaping what’s next.