7 Things Worth Buying Once You Have Money (Every Finance Guy Says Don’t)

I wrote a whole book about spending money to buy back your time. These seven are what I buy after that, and each one comes with the first move.

When I was 22 I was working 100 hours a week. I was a frenetic ball of energy and I was convinced that was my edge.

Then my body sent the invoice. I got sick, I got diagnosed with adrenal fatigue, and I got shingles on my back that my doctor caught just in time. I still could not turn it off. The whole time I thought those 100 hours were why I was winning, they were quietly costing me in the business, in my life, and in my relationships.

What pulled me out of it was a snowboard.

Most money advice is a list of things not to buy. These are the seven I do buy once the cash is there.

1. Buy something completely useless

It starts with a hobby.

Snowboarding came first. Then mountain biking. Now wake surfing. All they did was let me disconnect from the work, and the surprise was what happened when I came back to it. More energy. More output. Most people assume a hobby takes from the business. Mine started feeding it.

The science backs it. A study in Social Science and Medicine tracked 19,000 adults over 50 for eight years and found that people who picked up a weekly hobby saw their depression drop sharply over the following two years. Every guy I know at the top of his game has one. In the age of AI it matters more than ever.

One of my favorite books is Die With Zero by Bill Perkins. He treats money as a store of energy, worth nothing until you convert it into an actual experience. He calls the return on that conversion memory dividends. Money is useless until it buys memories.

Here’s the homework. Go back to who you were at 12 or 13, before “practical” existed in your vocabulary. What would that kid beg you for right now? If it was the ski hill, go buy a pass. Buy the small version and go do it this week.

Then run it through what I call the 3 Fs: something Fun, that you can do Frequently, with Friends. Wake surfing is mine. I do it every day, sometimes twice. And I put my team on the boat, plus people I barely know yet. That combination is what makes it stick.

2. Buy something that makes you lazy on purpose

There’s a study on parole judges that I think about constantly. Early in the day, a prisoner in front of that judge has a 65 to 70% chance of being approved for release. By the time lunch is close, the approval rate drops to nearly zero. The judge eats, comes back, and it shoots straight back up.

Same judge. Same kinds of cases. Wildly different outcomes, purely from decision fatigue.

I picture decisions as little battery packs in my brain. Every choice I make burns one. So the fewer choices I make on things that don’t matter, the more juice I have for the ones that do.

That’s why I wear the same blue shirt every day. It has nothing to do with being on camera. I just refuse to spend a battery pack on it.

The bigger one for me was food. My trainer looks at my numbers and decides what I should be eating. That goes into a spreadsheet, the spreadsheet goes to a local meal prep company, and they cook it and deliver it to my office twice a week. Every day at lunch I open the fridge and my meal is there. I have never once thought about it, I stay the same weight year round, and I am never hangry. Everything that would have gone into “what do I eat” goes into being more creative and being better for my team.

The most disciplined looking people I know aren’t actually the most disciplined. They automated the boring choices so discipline never has to show up.

Your move: pick one daily decision you’re willing to pay to eliminate. Meal prep is the one I’d start with. Cleaning works. Grocery ordering works. Wearing the same shirt costs nothing. And if you run a business, the biggest one of all is hiring an assistant.

3. Buy something that makes you not lazy

When I’m out in the world, the watch people ask about this watch. My favorite is when kids ask. They go, “Hey, is that a Richard Mille?” And I go, “Yeah, bro.” And they go, “How much is it worth?” And I say, “Do you really want to know?” They say yeah. I tell them half a million dollars, and they lose it a little. Then, unless I think they’re going to make a run for it, I take it off my wrist and hand it to them. Try it on. See how it fits.

I don’t wear it to tell anybody I own a half-million-dollar watch. I wear it to remind myself what I’m doing with my time.

I have a goal to build a billion dollars in enterprise value. Not for ego, not for the money, but to be an example of what’s possible, considering I started at zero and honestly worse than zero. I want a symbol on me that forces one question every single day: am I doing the thing that creates the probability of that outcome?

For you it might be the car. It might be the house or the cottage. When Jay on my team asked me if he should buy the Porsche, I knew his financials. He could afford it, barely. And that “barely” is exactly why buying it worked. That car made him show up for it every single day, and if you ask him now, his revenue is up.

It’s easy to get pulled into the day-to-day and lose sight of what you set out to build. That watch isn’t a flex. It’s a reminder I can’t look away from.

4. Buy yourself a new identity

At 22 I saved up everything I had, got on a plane, and went to Australia.

I expected to learn about other cultures, and I did. What I didn’t expect was the reset. In your day-to-day life, everyone around you already has a perception of who you are, and that perception quietly becomes your identity. I landed in Australia with none of that attached to me. So I got to choose.

I’d been the quieter guy. So I tried loud. You put it on like a jacket. If it fits, you keep it. If it doesn’t, you take it off.

That trip was the first time I ever got on a road bike, and I started riding 50 kilometers a day. I had never biked in my life. But nobody there said, “Dan, you’re not a biker, what are you doing?” They said, “It’s really cool that you’re a biker, you’re inspiring me.” I did a dozen things on that trip that my old identity had convinced me I’d be judged for.

A couple of years ago I did a smaller version. Five days alone in a van. My friends called it the Dan Vanposa. No device, no internet, no phone, no plan. I walked around and I talked to myself a lot. Have you ever been alone in the woods going, “Hey Dan, why are we here? Why am I saying we?” I didn’t have to be Dan in any of those moments. I could have handed myself a brand new name.

Sometimes you have to go find out who you are again. It teaches you humility, and it buys you the room to ask how you actually want to show up.

Your move: open your calendar, go out 6 to 12 months, and put the trip in. It doesn’t have to be Australia or a multi-month drive through Europe. Get in your car and go to a different city by yourself. Just remember why you’re there. You’re trying on behaviors to find out which ones you want to keep.

5. Buy yourself some friends

I know how that sounds. Nobody tells their kids to go buy friends.

A long time ago I read Never Eat Alone by Keith Ferrazzi and it rewired how I think about relationships. His argument, simply put: you are the byproduct of the people you spend time with. Your network is your net worth.

At the time his advice genuinely freaked me out. He says to invite business relationships to do things like work out with you. I’m reading this as an introverted programmer thinking, who on earth wants to go sweat in a spin class with me? He literally suggests Jazzercise. I’d never been. I didn’t want to go. The idea that a stranger would want to come along was laughable to me.

What I eventually learned is that with the right conversation, people say yes. A workout, a walk, a run. So I started organizing dinners and paying for them, with people I wanted in my life. I got on planes and paid for hotels to go to seminars on the chance of meeting one person who’d matter to me forever. My rule at any event was simple: find one or two people I could be friends with for the rest of my life.

Now look at what came out of that. My peer group, the couples we do date nights with, the families we vacation with, all met at events. I met my wife at an event. Getting to spend time at Richard Branson’s house came through a friend I met hosting one of those dinners. Mark Cuban investing in my company was a byproduct of inviting one guy to dinner.

These days I host a founders hike every Tuesday in Kelowna, BC. Thousands of people have come through it, people run their own versions all over the world now, and you’re invited.

Here’s my process, the 5×5 rule. Reach out to five people every day, and give five times more value than you’re asking for. Then host something. A dinner, a hike, a gathering. Pay for it if you can, because paying for the room is how you create the room. And when someone asks what the occasion is, tell them the truth: “I’m getting people like you together so you can meet each other. No agenda. I’ve got nothing to sell you.” I’ve been running that five times a week for years.

6. Buy yourself some money

When I exited my first company, Spheric, I had a real amount of cash in the bank for the first time. A mentor of mine told me to split it: half into the next big company, half invested. Learn how to make the money make you money.

So I put it into low-fee index funds, and I put some into other founders’ companies. Those angel investments became worth tens of millions.

Most people won’t do this. They leave it in a savings account or park it in a GIC because that feels safe. Money sitting still is losing value every single day to inflation. Your money today is worth less than it was yesterday, that will always be true, and right now it’s accelerating.

You don’t need to learn to trade. No puts, no options. Just be in the market, through a low-fee index fund, your primary residence, or stock in companies you’re already a customer of.

And if you’re early, the highest-return investment available to you is skills. Ask what you could learn that raises your earning potential, because that return can run 50 to 100% a year, compounded. Nothing in a brokerage account touches that.

Don’t leave your money in a pile. Send it out to work. Think of every dollar as a little soldier out in the world earning on your behalf, and understand that the interest your bank pays you is not what I’m talking about.

7. Buy yourself some love

This one sounds illegal. People say you can’t buy love. You can, and here’s how I found out.

When I was 11 I got put on ADHD medication, because somebody decided my energy was a problem for the classroom and therefore something was wrong with me. That decision started a slide. Depression, a string of bad decisions, hanging around people twice my age, drugs, and eventually coming very close to taking my own life.

At 17, a man named Brian sat me down and invested in me with his time and his words. I have never forgotten what that felt like. It became everything.

It’s the reason the Kings Club program exists, where I mentor young men. It’s the reason for the Martell Legacy Foundation, and it’s why I stop at detention centers when I travel. I was recently back at Portage, the rehab center that saved my life, sitting with 15, 16, and 17 year olds. One kid came up and told me the only reason he was there was that his mom had been showing him my videos.

I don’t know how to describe what that feels like other than love.

Most people tell me they’d give to charity, but it doesn’t feel like they get anything back. I’d argue the opposite happens. Every year my wife and I hold a giving day where we fund organizations working with troubled youth. When I hand over a check and the people running it are in tears, the love in that room makes every dollar worth it. That’s my why. Nietzsche put it better than I can: he who has a why to live can bear almost any how.

When you help somebody, it’s worth asking who’s really being helped. It takes both people, which is why I show up with time and not only a check.

Your move: ask who you needed in your darkest days. Ask what pain you went through that you’d spare somebody else. Then go be the resourceful person you needed, for one person, with a small donation at a hard moment. And don’t wait until you can afford it. If you won’t give when you have a little, you won’t give when you have a lot. The giving muscle has to get built.

The actual point

Freedom isn’t in your bank account, and it isn’t in your calendar either. It’s in what you invest in to bring more life into your life.

Most people who struggle to win are struggling because they made life hard. Put money into these seven and life gets full, which is what you were chasing when you started making it.

-DM