Before I tell you how I flopped forty-one times, lemme introduce you to the villain of this story. This is Chapter 2 of The Silver Scrolls, where the Dark Lord lays out his plan: raise the price of bread until folks work so long they stop looking up, and forget they ever had a dream. Sound like your Monday morning? Give it a few minutes, then come on down and I'll tell you how I walked right into that trap.

I once spent a year and about ten grand becoming a world-class expert at picking online businesses that don't work. Forty-one of them, if we're counting. And oh, I was counting.

Here's the embarrassing part: I'm not lazy, and I'm not dumb. I taught five-year-olds to read, write, and tie their shoes for twenty years — I can figure things out. So why did every “make easy money online!” thing leave me broker and grumpier than the one before?

Took me way too long to figure out. And the thing that finally cracked it open was… a villain I made up for a fantasy book. Stick with me. This'll make sense, I promise.

For twenty years I taught kindergarten. Finger paints, the ABC song over and over, roughly a dozen shoelaces a week and cute smiles to see every morning. I loved it. I figured I'd retire with an award plaque and a shoebox full of crayon drawings.

Then 2012 happened and our school lost its funding. Poof — two decades of “secure” gone overnight.

Now, I could've just gone and gotten another job. That part didn't scare me. But somewhere in there I'd dug my heels in. I was done working for other people. I wanted to be free — work for myself, travel, work from a beach or my kitchen table instead of being chained to one spot and up before sunrise every weekday whether I liked it or not. (Nothing against work, mind you. I love work. I just wanted to be the one who picks it.)

I went hunting for that freedom online. And I didn't try one thing, or two. I tried forty.

I bought the shiny software. I sat through the webinars that started at 9pm and somehow never, ever ended. I watched fellows lean on rented Lamborghinis and promise the whole thing came down to “one simple button.” (Spoiler: there is no button. There's never a button.)

Every so often I'd scrape together a sale — just enough hope to keep me hooked, like a guy who catches one tiny fish after eight hours in the rain and decides he's basically a professional fisherman now. But steady income? Nope. Not once.

By flop number forty-one, I wasn't tired. I was mad. I felt like a complete sucker. And that, my friend, is when the armor shows up.

Nobody hands it to you. You just wake up one morning with your arms crossed, squinting at every new idea, muttering “nobody's fooling ME again.” You tell yourself that wall keeps the scammers out. Took me ages to notice it was also keeping out every good thing — and keeping me parked exactly where I was.

Around then, I was writing a fantasy story — Silver & Scrolls. It's got a traveler named Robin, a long dusty road, and a proper villain: the Dark Lord, perched up on his big black horse, scheming to crush every dreamer in the land.

And there's this companion who travels with Robin. Good guy. Loves sailing. Just wants a decent life for his family. But the road keeps roughing him up — an arrow here, a smooth-talking con artist there, people he trusted making off with his silver. And with every hit, he gets a little quieter. A little harder. A little more certain that everybody's out to rob him blind. Until one day all that bitterness has hollowed him right out, and he walks himself straight into the Dark Lord's trap.

I wrote that character over a few weeks. Then one afternoon I set my pen down, read it back, and went, “…oh. That's me. I'm literally writing me.”

(I also made a short little film about the six roads I wandered down chasing this whole “freedom” thing. If you'd rather watch than read for a few minutes, here it is:)

Okay. So what's a cloak-wearing fantasy villain got to do with you, me, and a laptop at 11pm? Here's the whole point, and I promise it's not a riddle: the Dark Lord isn't real — but what he does is extremely real. He just doesn't look scary. No flaming sword. In real life he's quiet, and he gets you with three embarrassingly ordinary things:

He gets you alone. Convinces you you're the only one flailing, so you shut your door and quit asking anybody for help.

He makes it look complicated. Piles on so much techy, confusing nonsense that your brain just quietly powers off, and you go scroll your phone instead of doing the one small thing in front of you.

He makes you cynical. Whispers that anybody who actually pulled this off must be a crook — so why even bother trying.

That's it. That's the big bad. Alone, overwhelmed, and sure the whole thing's a scam. No dragon required. And honestly? That little trio has killed more good dreams than any actual con artist ever dreamed of.

Now, here's where I'd love to tell you I outsmarted all of it with some genius seven-step system. Nope. I just got lucky and met somebody further down the road who turned around and showed me two things. Brace yourself, because people build entire $2,000 courses to avoid admitting how simple they are:

One: you move forward by talking to a few new people every day, like a normal human being, and pointing them toward something that actually helps them. Not five hours. Thirty minutes. That's the part that's yours to do.

Two: you do NOT lug the heavy stuff around yourself. You let a system handle the grunt work — the answering, the explaining, the reminding, around the clock — so you're not personally typing the same answer for the ninetieth time at midnight.

That's the whole thing. You do the light part; the machine does the heavy part. I know. After forty tries, I was almost offended by how simple it turned out to be.

And once I quit trying to be the whole machine, the money finally made sense. The setup I landed on pays back 80% — about $128 a month per customer, on stuff folks actually use and keep paying for. Which means it stacks up like this:

Two customers and you've already covered your own costs. Twenty-four of them — not twenty-four thousand, not an army, just two dozen people — and you're looking at around $3,000 a month that keeps showing up whether you had a great week or spent it on the couch with the flu.

I'm not going to lean on a rented sports car and tell you to quit your job Monday morning. You've heard that song. So had I.

Here's all I've really got: forty flops behind you doesn't make you broken. It makes you a person with forty very specific examples of what not to do — which, honestly, is worth more than most folks' startup cash.

If you ever want to peek at the setup that finally worked for me, the door's open. No armor required.