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A few years ago, my brother Oleg and I were both back in Arad for our parents' wedding anniversary.
Arad is a small town in Israel, right by the salty shores of the Dead Sea. It was the place we landed when our family packed up everything in Ukraine and started over. Neither of us had much when we arrived.
We went to the same schools, served in the Air Force together, clocked in at the same facility for a stretch. Same roof. Same start. Same dreams of something better somewhere down the road.
I flew in from Toronto. Business class. I had bought our parents a three-bedroom apartment — mortgage-free — so they would never have to worry about rent again.
I was in no rush to get back. I had Italy planned for after.
Oleg drove in from a small town near Tel Aviv. He brought a bottle of wine. He couldn't stay long because his boss had refused to give him the day off.
I have thought about that afternoon many times since.
Not because I was proud of the contrast — I wasn't, at least not in the way that word usually means. I thought about it because that afternoon made something abstract feel completely concrete.
Two people. Same beginning. Same intelligence, same work ethic, same family. And yet sitting at the same table, we were living in entirely different worlds.
Before we go any further…
THE INSIDER DEAL
So you want to be original?
The path to success is littered with corpses of people who tried to be first…
The people who thought they had discovered something nobody else had ever thought of.
They are the ones who macheted their way through the jungle, only to step on a trap, get bitten by a snake, or fall off a cliff they didn't see coming.
Meanwhile, the people who came after them, the ones who waited, watched, and learned…
They walked down a cleared path, avoided the traps, wore snake-proof boots, and made it to the other side with limbs attached to their torsos.
My neighbor, Charley, used to run an eCommerce business selling indoor jungle gyms for kids.
At peak, he was moving decent volume. He grew his store to be the second in size in that niche market.
Then the market shifted, and his business collapsed. He had built something original in a market that was too fragile.
You can have the most delicious hamburger in the world, but if your hamburger stand is on the moon, you are going to sell exactly zero hamburgers.
I wrote my brand new book, Zero To Online, about how to enter markets where money is already changing hands instead of trying to be first.
It goes live this Thursday, April 16th at 12pm EST.
When the book drops, I'm releasing a set of limited launch bonuses, including the audio version of the book and a few live experiences with me that have never been seen before.
Sign up on the early bird list to get notified first and get access to the bonus packages before they fill up.
Now, as I was saying…
Several years earlier, we had each made a decision. Oleg's was the sensible one. He found a stable job with benefits and built his life around it. Mine was the uncomfortable one.
I started a business while working whatever I could find — waiting tables, security shifts, cleaning. Jobs I took to survive while I figured out something that could eventually replace all of them. There was nothing glamorous about that period. There was a lot of uncertainty, a lot of months where the math barely worked, and a family that thought I was making a serious mistake.
What kept me going was not confidence. It was the alternative.
On the day of that anniversary, Oleg was choosing between saving for a vacation or buying used tyres for his car. I was choosing between a month in Thailand or renting an S63 Mercedes across Europe.
There was another contrast that stayed with me. Oleg was deciding whether to buy winter clothes for his kids or a new set of tyres. I was deciding between investing in a property or buying stocks.
The difference is not just the dollar amounts. It is the entire frame of the decision — one person choosing between two forms of scarcity, and another choosing between two forms of growth.
The gap between those two realities did not come from luck or talent or connections. It came from one decision, made years earlier, that neither of us fully understood the weight of at the time.
That decision was which ladder to climb.
Before the online business, I worked at a pesticide production facility. I filled plastic jugs with green liquid so toxic that workers were mandated to take outside breaks every thirty minutes to avoid lung damage. The smell followed you home.
The work left you feeling hollowed out in a way that had nothing to do with physical tiredness. I hated that job in a way that is difficult to explain to someone who has never done work that makes them feel like they are disappearing.
Every shift felt like proof that I had chosen wrong — that something had to change or this was simply going to be my life.
What I eventually understood is that the job was not the problem. The ladder was.
Most people approach financial security the way Oleg did — the way almost everyone does. They find the most stable-looking structure nearby and start climbing. They do not stop to ask whether the ladder is leaning against the right wall.
They assume that if they climb hard enough for long enough, they will eventually arrive somewhere worth being. Years pass. They are higher up the same ladder.
The view is slightly better. They are still trading time for money, still dependent on a boss's mood and a company's fortunes, still one bad quarter away from a conversation that ends with "we're letting you go."
Oleg is not lazy. He is not stupid. He is one of the most capable people I know.
The problem was never effort. The problem was that the ladder he chose had a ceiling built into it, and nobody told him that before he started climbing.
The internet changed something fundamental about this equation, and most people still have not absorbed what it actually means. You no longer need capital, or an MBA, or a warehouse, or a prime retail location. You need a laptop and a connection.
The barriers that once kept ordinary people out of business ownership have been removed, and yet most people are still standing in line for jobs that could disappear tomorrow, building security on a foundation that belongs to someone else. They are waiting for permission that is never going to come.
I think about the waiter at the cafe near my place. Every morning I arrive, order my espresso, open my laptop, spend an hour doing the work. He brings the coffee, clears the cups, moves between tables with the kind of practiced efficiency that comes from doing something a thousand times.
He has no idea what I do. (He has no idea that in the time it takes him to serve the morning rush, I have made more than he will make all week.)
That is not a brag. It is a description of two different systems producing two different results for two people who are both working hard and both showing up every day.
One of us built something. One of us is serving it.
I am writing this because Oleg's story is not unusual. It is the default. It is what happens when intelligent, capable people make the conventional choice because nobody showed them that another one existed. And the longer they stay on that ladder, the harder it becomes to imagine stepping off it — even when the ceiling is right there above their heads.
Most people do not need more motivation. They need a clearer picture of what the two paths actually produce when you follow them long enough. Oleg is that picture. So am I.
The safe path produces safe outcomes. And safe outcomes, examined honestly, are not actually safe. They are just familiar.
You can't turn back the clock. You can choose a different ladder starting today.

P.S. If you enjoy these ideas, you’ll love the deeper conversations we have on the List Building Lifestyle podcast.



