Should You Fight for Success in America or Go Back? My Advice to a Young Truck Driver

Ilya found me through one of my videos and asked for a conversation, and within a week we were talking. He’s about to turn 30. Back home in the Luhansk region he ran a passenger transport company and was launching two small startups. In 2022 he had to leave. He lived in Poland, then in England, where he worked in construction without knowing English or the trade. Then he came to America: first Miami, then near Tampa, and now South Carolina, where his wife was offered a job. That’s four moves in a year and a half.

Today he drives a truck that hauls nine cars at a time. He came with about $45,000, made $105,000 last year, and America ate up all of it: moves, lawyers, the papers he needs to stay. He told me he takes it calmly, because his father and other entrepreneurs he knows were wiped out back home three or four times and had to start from zero each time. He wants to build something that will stay with his children.

I told him he has his whole life ahead of him. I was almost 32 when I started at $4 an hour as a loader in a produce store outside Chicago, below the Mexican workers who didn’t speak English, and I didn’t understand English at all.

When to stop working for someone else

His first question was how to know when you’re ready to quit your job and start something. I can’t name a date. Everyone gets there at a different pace, and you’ll know when you’re ready. What I can say is this: never put your last money into a business. When I started, I had a small amount set aside to live on, and I didn’t risk it.

A viewer once wrote to me that she had been carrying an idea for years while working 18 years for an employer, and she didn’t think she was a businessperson. I told her she might well be one. If you never start, you’ll regret it all your life. But don’t risk everything. Put aside enough to live on, so that if the business doesn’t work, you know you can get back in the truck and earn again.

In every one of my businesses I assumed it might not work, and then I did everything to make it work. I believed in it 100%, but I was ready for failure. At the start, live as frugally as you can and don’t show off to anyone. You’ll show them later, when you have something to show, and by then you won’t want to.

Should you keep ties with the country you left?

Ilya asked whether to build a business around his connections back home or cut those ties so nothing pulls him back. Never cut ties. But my situation was different. We left the Soviet Union as refugees in August 1989, stripped of citizenship, and spent a month in Austria and five in Italy before reaching Des Moines, Iowa, and then Chicago. In June or July 1991 I went back to Belarus, still part of the Soviet Union, on a refugee travel document; I didn’t even have a green card. Co-ops had started in 1987, the country was falling apart, and there was nothing in the stores. I started in Minsk and then in Moscow, where I didn’t know a soul, and within a year I knew more people there than most Muscovites.

It wasn’t easy to buy the right goods. I once paid for a container of what I was shown as beautiful flight jackets at $20 apiece. When we opened it, it was full of work jackets with people’s names sewn on them, and nobody would buy them.

I did business in Ukraine once and decided never to again, because of the corruption I ran into in the system there. I’m talking about the state, not the people; every nation has thieves and decent people. I wouldn’t do business in Russia or Belarus either, because the legal system doesn’t work. If Ilya can use his contacts to bring something here, sunflower seeds or olive oil, for example, that’s worth looking at. But if I were him, I would fight here. The market is enormous, competition is tough, and there is a lot of money. Look at what people need.

Don’t do everything for your children. Do it for yourself.

If you do well for yourself, your children will be fine. If you sacrifice everything for them and you’re miserable, it’s not clear they will be.

Margins, teams and the startup I closed

Ilya thought all my businesses had high margins. In fact my biggest business was cigarettes. In the ’90s I was a distributor for Philip Morris, British American Tobacco and RJ Reynolds. It’s a very low-margin business, but the volumes are huge: I shipped 40 to 100 forty-foot containers a month and made money on volume. I was also a partner in Centro Obuv, a shoe company; I left in 2011, and by 2013 it sold about 72 million pairs a year through 1,300 stores. I like businesses where you can do huge volume even on a small margin. Which is better, selling Toyotas and Hondas or Ferraris and Lamborghinis? Toyotas: you sell a thousand of them while you sell one Ferrari.

As for investors, margin isn’t the main thing. Startups often lose money for years, and Amazon lost money for a long time before it turned a profit. What investors look at is the team: honest, energetic, ambitious people with a track record, and at least one person who sees where things are going. They might even have the wrong idea, and a good investor will tell them so. Two years later you may be doing something completely different from what you planned. The main thing is to jump into the fight and see who comes out on top.

I learned that with my own startup. I was the CEO, but I knew I’m a poor manager, so I looked for an operating executive. Candidates came in wanting $350,000 a year, telling me how outstanding they were and asking me to step aside and let them run everything. I asked each of them whether they had ever built a company worth $100 million, or even $10 million. None had. I was putting in the money; why would I hand them the reins? I never found the right person.

When do you close a company instead of pushing on? When it stops being a pleasure. My daughter, who has her own investment business, helped me at my request, carried a lot on her shoulders and got very tired. I didn’t want to wear her out, and without a strong team I closed it. The company had reached break-even, but I had put in $2.5 million of my own money and lost it. We had 30 programmers, contracts with Quest Diagnostics and Labcorp, the two biggest lab-testing companies in the country, close to 1,000 imaging centers on the platform, and we were starting on pharmacies. Every price was shown up front, before you went to the doctor.

The idea started with my own MRI. The hospital billed my insurance $18,339 three months after the scan, and I had to pay $5,413 myself. On my platform the same scan cost $350. A blood test cost $20 with us. Pay a doctor cash for it and he’ll ask $90 or $100, yet he would bill insurance $1,400 for the same test. People need that kind of transparency. Hospitals and insurers don’t. Healthcare is the biggest industry in America, about $4 trillion a year, and I got another big dose of life experience.

Which business to start, and how to learn it

What should a first business look like to have a better chance? It depends on you. Without a lot of money it’s hard to start in artificial intelligence or robotics, even though that’s where the future is. I know a man named Denis in Chicago who is also 30, started from scratch and now has well over a hundred trucks. Do what you love. I didn’t become a loader because I liked hauling crates and mopping floors; I had no choice. Once you have at least a little money, choose what you like, and then look at the market.

Around 2004 I saw breath strips at a trade show, the thin film you put on your tongue. They told me pills would soon dissolve on the tongue like that. I created my own brand in Russia, and because I was a cigarette distributor, I got it into about 80,000 stores and kiosks, ahead of Listerine and Wrigley. I lost a million dollars on it. People at the register looked at the strips and didn’t understand what they were. Building a new category would have taken maybe $500 million in marketing, and no company decided it was worth it. You have to understand which segment you’re entering, how big the market is and what the competition is.

Ilya listed the businesses he was looking at: selling and servicing cars, a trucking company, pizzerias, a dumpling franchise, flipping houses. In every one of them I know someone I could call and ask what the problem is. Friends of mine had about 50 Sarpino’s pizzerias ten years ago as franchisees, mostly takeout. A man I know named Dima had eight cafés and restaurants in Kyiv, came here and got behind the wheel of a truck, because he wants to understand the mentality before he opens anything. There is risk everywhere; nothing is risk-free. And you may start with pizzerias and end up selling fish.

Courses, college and finding a mentor

Ilya was thinking about paid courses in online real estate deals. When I hear pay us and we’ll teach you, I feel sick. I don’t trust any of them. If a course gives you a license you need, pay for it. Otherwise find someone who actually does the business and ask to spend three days with him. Three days next to that person will teach you more than three months of courses. I watched people play preferans, a card game, from sixth grade to tenth and never really got the rules. Then I played for money for the first time, lost, and understood almost all of them. Offering to work for a professional for free for a couple of weeks to learn is a good idea; whether he wants to teach you is another question.

He also asked whether to invest in his own education, a master’s degree, say. In my opinion, that’s lost time and lost money. The best experience is your own, and you get it in real life. If you’re smart, you’ll learn and fix your mistakes as you go; if you’re not, no university will help. While he’s driving, he can keep a little money working: my wife trades options, and our family rule is never to use margin, never to borrow. I’ve seen people lose everything that way.

Ilya listens to podcasts behind the wheel and wants to start a YouTube channel to make connections. I told him to talk on camera himself instead of only watching other people. He knows car hauling, which is full of details nobody writes down, so a course of his own on getting into the profession could be a good product. And where to find a mentor? I’d look in the Russian-speaking community, at least while his English is still limited; even after all my years here I can’t explain every nuance in English the way I’d like. I never had a mentor myself. People who don’t charge will answer once or twice as a favor and then stop picking up. I’ve been offered money to coach people one on one and in groups and turned it down so far. Maybe one day.

Originally published as a video on my YouTube channel on 11 July 2025. Watch on YouTube