What to do after your first million? Enjoy it and take pride in it, but don’t spend much of it. Invest carefully, stay humble because the market will humble you, keep cash ready for real opportunities, and never let your net worth become your self-worth. That’s how Timothy Sykes put it when I sat down with him in Bali.
Tim is the one and only. He’s a penny stock trader, a multi-millionaire, a world traveler who’s been to over 117 countries, and the founder of a charity community called Karmagawa. He’s also one of the most generous people I know.
He’s been on the Addicted2Success podcast before. That first time, we talked about how he turned $12,415 into more than $4 million trading penny stocks. This time I wanted to know what you do once the money is real.
He also teaches. When we spoke, he said he had about 9,000 paying students and a handful of millionaire students, and he was quick to add that not everyone is going to be a millionaire. “Don’t make crazy promises,” he said. He uses those students as examples of what’s possible, not as a guarantee. I respect that.
Tim and I first met over Skype. He was a big fan of Addicted2Success. The next time we met, we were hanging out in Laos in Southeast Asia. We’d both built schools with Pencils of Promise, and we had nothing but laughs on that trip. There was a whole lot of giving back there. Our community wrote up what we learned from raising $50k and building a school for children in Laos, and Tim went big. I think he donated about a million dollars for twenty schools.
So when we sat down again, I wanted to talk about money. It’s a big conversation for so many people. Most of us think about how to make the first million. Very few think about what to do with it once it shows up.
What to do after your first million: enjoy it, but don’t blow it
I asked Tim straight out: if someone made their first million, what would he tell them to do?
“I mean, enjoy it. That’s the dream, right?” he said. “I would not spend a lot of it, but definitely take pride in it and treat yourself.”
I love that answer because it’s balanced. He’s not telling you to live like a monk. You earned it. Celebrate it. But a celebration is a moment, not a new monthly lifestyle.
That lines up with what regulators tell people who come into big money. FINRA’s guide to managing a financial windfall suggests holding off on big moves for the first six to 12 months, getting organized, and remembering that a “$1 million” headline number can shrink a lot after taxes and fees. Your first million in business works the same way. Know what you’ll actually keep before you decide what to do with it.
Stay humble, because the market will humble you
Tim’s next point was about ego. “It doesn’t matter how much you make. If you get too cocky, the market will humble you,” he told me.
He said he tells people the same thing whether they’ve made a million, a hundred thousand or even a thousand dollars: only put a small portion of it into any investment, because any investment can turn bad. Anything can happen in life.
He said he’s seen enough in the stock market and in teaching to know not to get cocky. The danger is the beginning. “You make money, it’s like, oh, it’s so easy,” he said. “All it takes is that one time where you’re so cocky, then you lose everything.”
That’s the trap after a first big win. You start to believe it was all skill. Some of it was. Some of it was timing. The first million can make you feel bulletproof right when you have the most to lose.
Why fast money tends to disappear
When I asked Tim for his mindsets for up-and-coming entrepreneurs, number two was patience. “Nothing happens in a day, in a week, in a month, in a year,” he said. “And if it does, you don’t appreciate it.”
He compared people who get successful too fast to a Hollywood star or a lotto winner. They usually screw it up, he said, because they didn’t go through the ups and the downs. They didn’t really earn it. “Most likely, even maybe subconsciously, you’re gonna lose it.”
“Like sabotage, right?” I asked him.
“100%,” he said.
That’s worth sitting with if your first million came quickly. It doesn’t mean you didn’t deserve it. It means the skills that keep money are different from the skills that made it, and you have to learn them on purpose.
Sometimes the best investment is no investment
This was the part that surprised me most. I asked Tim what he invests in, and he named a few things. There was a quirky food startup he’d backed, and some real estate, starting with a house he bought for his parents. Then he said he stays in cash a lot.
“Sometimes the best investment is no investment.”
His reasoning: when you have money, you feel pressure to put it somewhere. So you put it somewhere just because you feel forced. Then it tanks, the best opportunity shows up, and you’re stuck in a bad position you can’t get out of. He likes keeping a lot liquid. When we spoke, Tim said he didn’t own a single stock and had more than $10 million in cash.
To be clear, that’s Tim’s choice for Tim’s situation, and it’s not a recommendation for yours. Cash has its own costs, like inflation, and everyone’s goals and taxes are different. What I take from it is the mindset. You don’t have to deploy every dollar the moment it lands. Talk to a fee-only fiduciary advisor and a CPA before you make big moves with a big number.
Your net worth isn’t your self-worth
Here’s the thing. A lot of people tie their sense of worth to their money, which is actually really dangerous.
I shared a story with Tim that has always stuck with me. As I remember it, there was a Russian billionaire, one of the wealthiest people in the country. A financial crisis hit and he lost billions, and his whole worth was so tied to that number that he took his own life. Then, a couple of years later, his money would have recovered past where it was before. He never got to see it.
So I asked Tim, how do you dance between having your worth in what you’ve created and stepping outside of it, having your identity in something greater than yourself?
He brought up Jesse Livermore, who’s often called one of the greatest traders who ever lived. Livermore made and lost huge fortunes, went bankrupt more than once, and eventually took his own life. Tim said if he lost everything, he wouldn’t go that way. “I would get, like, motivated,” he said. He joked he’d eat ramen noodles and livestream the whole comeback.
Then he said the line I’d underline. “It’s a game. It’s a challenge. That’s how money should be viewed. It’s nice to have freedom, it’s nice to have these luxuries, but it’s not your net worth. You’re alive as long as you’re alive, and you have ideas and you can think and you can execute and you can try new stuff.”
If money stress ever has you in a dark place, please talk to someone. In the US, you can call or text 988 to reach the Suicide and Crisis Lifeline. No number on a screen is worth your life.
Money buys you freedom from what people think
Tim gets a lot of hate online, and he doesn’t hide from it. Some people, he said, will watch him and think he’s just a millionaire saying whatever he wants. His answer: “I don’t care. That’s the beauty of money. It’s freedom.”
He told me his biggest growth spikes came from negative stories, not positive ones. When a rapper used one of Tim’s cash photos and Tim called him out, the fight trended, and Tim said he picked up about 300,000 followers in 48 hours. Meanwhile, when he donated a million dollars, he said there wasn’t one article about it.
His lesson was about honesty. “If you’re real, the negative turns into a positive bigger than you could possibly imagine,” he said. If you’re a scam, you should be afraid of exposure. If you’re real, “try to expose me. What do you got?” After a first million, people will judge you either way. Being transparent is what keeps that judgment from hurting you.
Why the Lamborghini stopped doing anything for him
Tim is famous for posting cars and stacks of cash. He owns that. “I’ve been known to post stacks of a million dollars on social media,” he said. “I get it. I’ve been on the other side.”
But listen to how he describes it now. “I have a few Lamborghinis. I’m very blessed. They mean [nothing] to me. I drive fast, I feel nothing anymore. It’s sad. When I open a new school, I feel a whole bunch of stuff.”
He said he grew up middle class and just wanted to be rich: the cars, the lifestyle. “But once I got it, it’s like, okay, that’s cool, but what else is there?” He said a lot of rich people aren’t happy because they thought the money and the stuff would make them happy, and it didn’t.
What he appreciates most now is freedom. He moved his parents to Miami and bought them a nice place. He can take care of loved ones, friends and whole communities.
I asked him why giving back seems to hurt engagement online. For some reason, whenever you share something about giving back, it doesn’t travel like a flashy post does. Tim said it’s simple. Post a Lamborghini and people go crazy. Post a new school and it’s “good job,” golf clap. He’s trying to change that by bringing filmmakers and influencers along to the school openings so their audiences see what giving looks like.
That’s also why Karmagawa isn’t named after him. It used to be the Timothy Sykes Foundation, he said, “but it shouldn’t just be about me. I have enough [stuff] named after myself. My ego needs less these days.”
Learn what actually makes you happy
Tim said you learn what makes you happy over time, and too many people don’t adapt. If you’d asked him a decade earlier whether he’d be building schools, he joked, he’d have told you to come for a ride in his Lambo so he could show you what really matters.
That honesty is why I trust him on this. He’s not saying money doesn’t matter. He chased it hard and got it. He’s saying the stuff stopped delivering, and the freedom and the giving didn’t.
Near the end, Tim talked about the families he’s met in Indonesia. “They have nothing, and they’re just so happy to be alive,” he said. Then there are millionaires and billionaires with everything at their fingertips who don’t appreciate it. “Perspective matters.”
So once you hit the number, try things. Fund something you care about. Take care of your people. Notice what actually makes you feel something, and do more of that.
Before the first million: an extra hour on what you love
For anyone still working toward it, Tim’s last 30 seconds were gold. He said this time we’re living in is an opportunity, and too many people waste their potential because they’re afraid to focus on what they love.
If you have money issues and a normal job, he said, study at night and on weekends. Set your alarm an hour earlier. Give what you love an extra hour or a few hours a week, and “you’ll be shocked at what you can do” over one, two, three or five years.
I shared a quote with him that I’d come across: you’re not tired because you’re actually tired. You’re tired because you’re not focusing on the thing that lights you up from within.
A simple checklist for your first million
- Celebrate once. Treat yourself and take pride in it. Then go back to normal spending.
- Know your real number. Work out what’s left after taxes and fees before you plan anything.
- Slow down. FINRA suggests waiting six to 12 months before big moves with a windfall.
- Get a team. A fee-only fiduciary advisor and a CPA, not a hot tip from a friend.
- Stay humble. Don’t let one win convince you you can’t lose. Any investment can turn bad.
- Don’t invest just to feel busy. As Tim put it, sometimes the best investment is no investment.
- Separate your worth from your net worth. Your ideas and your ability to execute are the real asset.
- Find what makes you feel something. For Tim, it’s opening schools, not driving Lamborghinis.
FAQ
What should you do after your first million?
Celebrate it, but don’t spend most of it. Work out what you keep after taxes, slow down before big moves, get a fiduciary advisor and a CPA, and invest carefully. Timothy Sykes warns that if you get too cocky, the market will humble you.
Should you invest your first million right away?
Not necessarily. FINRA suggests holding off on big moves for six to 12 months after a windfall. Timothy Sykes says sometimes the best investment is no investment, because forcing money into something can leave you stuck when a better opportunity appears.
Does making a million dollars make you happy?
Not on its own. Timothy Sykes says his Lamborghinis make him feel nothing now, while opening a new school makes him feel a whole bunch of stuff. He says what he values most is the freedom money gives him.
Why shouldn’t you tie your self-worth to your net worth?
Because money goes up and down, and you’re more than a number. Timothy Sykes calls money a game and a challenge. As long as you can think, execute and try new things, you can build it again.
How much of your money should you risk on one investment?
Timothy Sykes says he only puts a small portion into any investment, because any investment can turn bad. The right amount depends on your goals, taxes and situation, so get advice from a fee-only fiduciary advisor.