About six years ago I was at a family funeral. During the luncheon I found myself in a conversation with my wife’s uncle’s father-in-law. A great man. We only ever had two conversations, and I am so grateful for both of them.
He told me about his career. He had tremendous success in his mid-forties, but it came from his tenth or eleventh company. The first nine or ten either failed or went nowhere. For years he thought he just didn’t “get it”. He figured he was slower than other entrepreneurs. That something was wrong with him.
Then he became an early stage investor.
He started backing other founders, expecting to watch them do what he couldn’t. Instead he discovered that only about one in eight to eleven of his investments returned anything. The rest failed or flatlined.
That was when he realized he wasn’t broken. He was normal. He was right in the pocket the whole time.
His counsel to me was simple. Keep going. Don’t stop. If one doesn’t work, set it aside and start again.
A few years later I was catching up with a friend who’s part of a VC fund. Different world, same math. He told me their returns come from about one in eight to eleven companies. The rest either die or turn into zombies.
I have not been able to shake either conversation since.
Not the math. The asymmetry.
VCs get to play a portfolio. They spread capital across founders and accept that most will fail. They can afford to be wrong eight or nine times out of ten because the winners cover the losses.
Founders don’t get that luxury. We pick one idea and bet everything on it. If it doesn’t work, we start over from zero if we’re lucky. Usually we start over from a position of serious loss.
That math has never favored this learning process.
What Changed
For years, solo founders couldn’t compete. VCs had capital, networks, and teams. One person alone couldn’t move fast enough or cover enough ground.
VCs have three advantages over regular founders.
Capital, which buys time. We call this runway.
Expertise, which allows you to hire expert employees and consultants. Helps avoid the dumbest mistakes.
And a Portfolio, which means they can afford to be wrong nine times out of ten.
Then AI showed up. And suddenly solopreneurship became real.
Allow me to introduce you to Claude, ChatGPT, Gemini, and Grok. Four different flavors of “I can help you build that.”
All jokes aside, these are real change-makers in a solopreneur’s life.
They’re not perfect. Not magic. But fast enough and capable enough to change the math.
Time? Stop watching Netflix and boom, you’ve got time again.
Expertise? These things have read more than any human ever will. They won’t replace a great advisor, but they’ll fill gaps you didn’t even know you had.
Capital? Still a problem IF you’re using the wrong playbook. But if you can move faster and test cheaper, you need less of it… millions less.
Which leaves the last piece. A diversified portfolio of startup “bets.”
The Experiment
What if a solopreneur could run a portfolio like a VC does? Not capital spread across founders. Effort spread across startups.
Ten startups. One hundred days.
That is what I am testing. Starting tomorrow.
Each startup gets ten days.
But the plan must have built-in guidelines designed to overcome the most common startup blockers just about every founder has been trapped by.
- not knowing the target audience before starting
- analysis paralysis and second-guessing yourself
- building the wrong product because you’re building it for a potentially wrong audience
- feature creep… the “just one more feature and it’s done” trap is real
- perfectionism… waiting for “ready” when “good enough to test” is what actually works
- confusing interest with intent… signups, friends saying “that’s cool” and “everyone I talk to gets excited about what I’m offering” are not sales
- sunk cost paralysis… can’t kill the idea because you already put three months and money into it
- avoiding the hard part… staying busy building because selling feels uncomfortable
- premature optimization… worrying about scale before you have ten customers
- falling in love with your solution instead of the problem
So, here’s my starting plan… (I reserve the right to make it better as I progress and learn):
Days 1-2: Research & Pitch. Know your customer. Write the pitch before the code. If you can’t articulate why someone should buy, building it won’t help.
Days 3-5: Build MVP. The Minimum Viable Product (MVP) only needs to prove the concept. Core functionality only. Three days, no feature creep.
Day 6: Launch. Go live. Real people, real money.
Days 7-9: Iterate. Read the market. Three pivots max to find the right angle.
Day 10: Verdict. 5 sales = continue. Else, move on.
Saturdays count. Sundays off. This is a marathon, not a burnout speedrun.
If something gets five sales, it passes. If it doesn’t, I move on.
If something takes off early and starts showing real traction, the experiment ends. I chase that one.
The Real Game
This is not about building ten companies. It is about finding one that hits.
Most founders fail because they fall in love with their idea instead of hunting for the market. They spend months building something nobody wants. Then they spend more months trying to convince people to want it.
I know because I have done this many more times than I really want to admit to.
I have watched this pattern destroy more startups than bad code ever has.
The real game is Product Market Fit (PMF). Everything else is noise until you find it.
I spent four and a half years studying direct response copywriting. Not because I wanted to write ads. Because I wanted to understand why people buy.
Eugene Schwartz, one of the great direct marketers of times past, taught me something that changed how I see every product launch.
Markets move through stages of awareness.
Most founders write website and sales copy for buyers who already know they need the solution. But most markets are full of people who don’t even know they have the problem yet.
Talking to the wrong awareness stage is the fastest way to kill an offer.
This experiment is built on that foundation.
Ten shots at finding the right message for the right audience at the right time. Each one a fresh attempt to catch the market where it actually lives.
The Rules
I am giving myself constraints to keep this honest.
Each startup gets ten days maximum. No exceptions. No “just one more week.”
If it doesn’t show signs of life in ten days, I let it go.
Five sales minimum to consider something worth continuing. Not signups. Not interest. Sales.
Three messaging pivots allowed per product. If the offer doesn’t land after three rewrites, the problem isn’t the copy. It’s the idea.
All of this happens in public on X, here on my blog and if I get brave enough, on YouTube. I will document the decisions, the pivots, the failures, and whatever wins show up.
Why Public
There are two reasons.
First, accountability. It is easy to cheat when nobody is watching. Easy to extend a timeline. Easy to count a maybe as a yes. Doing this in front of people keeps me honest.
Second, I think the model matters.
If this works, it changes the math for every solopreneur who has ever felt stuck picking one idea and betting everything on it. If it fails, at least I’ll know why and I’ll do my best to share that.
Either way, the data is worth capturing.
What’s Next
The first product launches tomorrow.
Ten days. Then the next one.
If you want to follow along, I’ll be posting updates here and on X. If something hits, you’ll know. If everything fails, you’ll know that too.
Let’s see if one person plus AI can be their own VC.
Want to Do This Yourself?
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Start Your 100-Day ChallengeIf you want a front-row seat to my journey, follow me on X. That’s where the real-time updates will land.