I Spent My Life Building It. Now What?

The other night, my wife Tracey and I were having dinner with a friend who happens to be the superintendent of our local school system. At some point, Tracy asked him a simple question: “Where is the biggest need?” His answer hit me harder than I expected.

He told us there are hundreds of kids in our community who are technically homeless. Then he started talking about food insecurity—kids who might get breakfast or lunch at school but go home without knowing what they’re eating for dinner. I’ve lived in this community most of my life, and suddenly I found myself thinking about something in a completely different way: What am I actually going to do with everything I’ve worked so hard to build?

Here’s the weird situation I find myself in at 50 years old. My wife and I chose not to have children. We love kids, but having our own simply wasn’t the life we wanted, and I have absolutely no regrets about that decision. But when you get older, not having children creates some interesting questions you probably weren’t thinking about when you were 25. Who takes care of us when we’re old? How much money do we need to make sure we can afford whatever care we might eventually need? And then there’s the really big question: when Tracey and I are both gone, where does everything go?

I’ve spent most of my adult life working, building businesses, investing, saving, and trying to create financial security. I’ve got businesses, investments, and property. I’ve worked incredibly hard for everything I have, and somewhere along the way I realized something kind of crazy: accumulating money is actually the easy part of this equation.

Figuring out what the hell to do with it when you’re gone is much more complicated. If you have children, the answer might seem obvious—you leave it to your kids. But when you don’t have kids, suddenly you start looking down the family tree thinking, “Wait… some third cousin I barely know is eventually going to end up with this stuff?” 

This is why I’ve become a huge believer in planning. I have a trust that spells out what happens to my assets, property, investments, and even the care of my cats. And regardless of how much money you have, I believe everybody should at least have a will. You don’t need to be wealthy. You could own three pairs of sneakers and a Matchbox car collection—it doesn’t matter. Clearly documenting your wishes is one of the most loving things you can do for the people you leave behind. Death makes people emotional, and money can make people crazy. Removing uncertainty removes an incredible amount of potential stress and conflict.

But lately, I’ve realized that simply deciding who gets what isn’t enough for me. I’ve started thinking more about impact. Tracey and I have already established an endowment through our local school system that helps kids who are struggling with things like food, housing, and basic necessities. Tracey also adopts families during Christmas and buys presents for kids who otherwise might not have much of a Christmas at all. These aren’t things we do for attention. They’re things we do because helping somebody—especially a kid who had absolutely no control over the circumstances they were born into—feels meaningful.

That dinner conversation about homeless kids and hunger pushed us even further. We started asking ourselves: What if we could create something bigger and more permanent? We met with people in the school system, we talked to my accountant, and now Tracey and I are in the process of establishing a nonprofit foundation that will allow us to direct money toward causes and needs that we genuinely care about—not just today, but hopefully long after we’re gone.

This whole experience has made me think differently about the word ‘legacy’. When I was younger, legacy probably would have sounded like some ego-driven concept—how many businesses did you build? How much money did you make? How many followers did you have? Did people know your name? But the older I get, the less I think any of that matters once you’re gone. Nobody cares what your revenue was in 2019, and nobody gives a crap how many views your YouTube channel had. The question that matters more to me now is: Did anything you built actually make somebody else’s life better?

I also don’t necessarily believe that handing somebody millions of dollars simply because they happen to be related to you is always an act of kindness. I’ve seen people inherit huge amounts of money, and sometimes it screws them up. When everything is handed to you, you can lose the hunger, drive, confidence, and satisfaction that come from building something yourself. I know that might sound harsh, but struggle—within reason—is incredibly valuable. Some of the most important lessons in my life came from failing, going bankrupt, being scared, and figuring out how to get back up. If somebody had simply dropped a giant bag of cash in my lap, I’m not convinced I would have become the person I am today.

And that realization connects to something else I’ve learned about success: more isn’t always better. There was a time when I was constantly thinking about growth. How do I make more money? How do I grow this business? What’s the next opportunity? But eventually you reach a point where another dollar doesn’t dramatically change your life. At that point, continuing to chase money simply for the sake of having more starts to feel a little ridiculous. I’m much more interested now in protecting what I’ve built, minimizing unnecessary risk, enjoying my life, and figuring out how my resources can actually accomplish something worthwhile.

This is also why my approach to business has always been more conservative than some entrepreneurs. I don’t believe in growth at any cost. I want businesses with healthy margins, manageable expenses, sustainable customer acquisition costs, and actual profit. I learned some brutal financial lessons earlier in my life, including going through bankruptcy, and afterward I made myself a promise: I never wanted money to control my life like that again, I don’t want to leverage myself to the eyeballs just because somebody tells me I could grow faster, and I want to sleep well at night.

The funny thing is that success creates problems nobody really talks about. When you’re broke, the question is, “How do I make money?” When you finally have enough, the question becomes, “What do I do with it?” And I’m realizing that the second question might actually be harder. Money is a tool: you can spend it, save it, invest it, give it away, use it to create opportunities, and/or use it to solve problems. But eventually, whether you have $10,000 or $10 million, somebody is going to have to decide where it goes.

So right now, I’m trying to figure out how to give away my money. Not tomorrow—I’m still planning on sticking around for a while. But someday, I want the things I worked for to continue doing something positive after I’m gone. Maybe that means feeding a kid who doesn’t know where dinner is coming from. Maybe it means helping a family keep a roof over their head. Maybe it means giving a young person an opportunity they otherwise never would have had. I spent the first half of my life figuring out how to build something. I think the next chapter is going to be about figuring out how to make what I built actually matter.