Well, THAT escalated quickly.
The first 30 days of my “99 Products Challenge” have officially wrapped—and what a whirlwind it’s been. I laughed. I cried. I pivoted. Twice. Maybe three times if you count that brief moment I considered selling artisanal AI-powered paperweights.
But let’s start at the beginning.
Ideation: My Superpower (and Possibly My Downfall)
Coming up with product ideas? Easy-peasy lemon squeezy. Honestly, I could do it all day. In fact, I did. I’ve always lived with one foot in dreamland, so the ideation phase was a delight. Turns out the “99” part wasn’t the hard bit. If anything, I had to restrain myself from going full Oprah: You get a product! And you get a product!
But here’s the thing about ideas: they’re like puppies. Adorable at first. Then they start peeing on the carpet and demanding food.
Brand? What Brand?
Pretty soon, the reality set in: having a hundred ideas doesn’t mean a thing if you can’t explain why anyone should care. Who are you? What do you do? How does it help me?
I realized that if I couldn’t answer those questions clearly, confidently, and without a flowchart… nobody was going to buy what I was selling. And so began the existential crisis portion of the challenge, also known as: The Branding Phase.
The First Pivot: New Me?
About two weeks in, I executed Pivot #1. New website. New product descriptions. A renewed sense of hope and vigor.
And then I started talking to potential customers.
And then… silence.
Not the good kind of contemplative silence. The “staring blankly while slowly backing away” kind of silence. I realized that testing ideas in the real world comes with an uncomfortable truth: many of your ideas aren’t nearly as clever as you thought.
A Crash Course in Product-Market Fit (aka Humility)
Here’s a not-so-fun discovery: finding product-market fit is a lot harder than coming up with a snappy tagline.
Worse yet, some of the markets I thought I was targeting didn’t actually exist. I had dreamt up whole ecosystems—customers, use cases, even pricing tiers—for audiences that were basically imaginary.
This wasn’t just ideation. It was full-blown hallucination. Oops.
Pivots Two and Three: The Reckoning
So back to the drawing board I went. With each pivot, I adjusted my product line, reshaped my business concept, and started to sniff out real problems that real people might actually pay to solve.
Turns out, you can build 100 products, but if there’s no viable market or business model behind them… congratulations! You’ve just completed the world’s most ambitious hobby.
The Realization: It’s Not About Products—It’s About People
Here’s the big insight from 30 days of hustle: products are easy. Customers are hard.
You can spin up a product in an afternoon. But building trust, offering something truly useful, and solving a problem that makes someone pull out their wallet? That’s the real magic.
Which brings me to…
The Next Challenge: 99 Customers in 30 Days
That’s right. I’m shifting gears.
Starting today, I’m launching The 99 Customers Challenge—a quest to find 99 real, live, willing-to-pay customers in the next 30 days.
This is the part that’s always been hardest for me. But it’s also the part that turns a bunch of ideas into an actual business. And that, my friends, is where the real adventure begins.
So stay tuned.
Because the product part was just the warm-up. Now it’s time to connect, serve, and build something real.
Let’s see if I can go from dreaming up ideas… to delivering real value.
—Tom
The 99 Product Challenge 
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