Over the 18 years I ran Tatango, we were fortunate enough to sell some of our shares a few times before we sold the company outright in October 2025. So our money arrived in a few big lumps, every couple of years, rather than building up steadily the way it does for most people. However it shows up for you, whether it's a sale, an inheritance, a settlement, or a lottery ticket, the experience is the same once it lands. You get presented with an overwhelming number of investment options, and a lot of confident people telling you which one is right.
We knew the advice. Don't do anything for a year, get used to the money, don't rush. But like everyone who comes into money, we looked at it sitting there and thought, what a waste. It could be working for us. Every month we waited, our money was losing money to opportunity cost. Or so we told ourselves.
So we asked around. We reached out to every friend we had who'd come into money and asked where they put theirs. Single stocks, index funds, government bonds, corporate bonds, multifamily real estate, real estate debt funds, triple-net, value-add, REITs, bitcoin, ethereum, alt coins, crypto funds, angel deals, VC, private equity, hedge funds, private credit, art. The list went on. There was no consensus, not even close. So we landed on what felt like the smart move. Diversify. Put a little into each, see how they performed and how we felt holding them, then consolidate over time into the ones we liked best.
If I could go back and tell myself one thing, it would be this. Don't put your money into anything you can't get out of quickly and cheaply.
The reason isn't that the opportunities are bad. The reason is that you are about to change. Your goals will change. Your risk tolerance will change. Your education about money will accelerate faster in the next year than in your whole life before it. The version of you twelve months from now will understand things this version can't. The entire point of the first year is to stay liquid enough to act on what that person learns, and locking yourself in is exactly how you take that away from them.
Here's what that looked like for us.
The investments we couldn't get out of
Real estate is just one example of many, but it seemed so obvious at the time. Cash flow, appreciation, an asset class we were familiar with. My parents had invested in real estate successfully, so I felt qualified to judge it. I ended up in dozens of syndications and funds before I really understood what I'd signed up for. The high returns came with high risk, which I didn't fully grasp going in, and I found out the hard way that I wasn't comfortable with that risk. The K-1s piled up every spring and became a tax headache of their own. The capital calls kept coming, on the fund's schedule, not mine. And there's no quick exit from a real estate fund. That mattered more than I expected, because we learned much later that we valued staying liquid over chasing the higher returns. Fast forward five-plus years and we're still stuck in positions we wish we'd never entered, with no way out in sight.
And here's the part that took me longest to see. It wasn't only the bad picks that hurt. Even the deals that performed fine had quietly taken something from me, which was the option to change my mind. By the time my goals shifted, I couldn't move that capital to where I now wanted it. The money was doing okay. It just wasn't free. The problem was never only whether I picked right. The problem was the lock.
Sidebar: purchases, commitments, and lifestyle
This goes well beyond investments, and it's the part I most wish someone had hammered into me. The same rule applies to commitments and lifestyle, and those can trap you harder than any fund, because there's no secondary market for them at all.
Don't take the board seat. It locks up your time and attaches your name to other people's decisions. Don't commit to the enormous family trip you're funding eighteen months out. It becomes an obligation you'll honor long after your life has moved on. Don't start building a house, but more on that below. And don't start a charity and begin hiring people and raising money. That last one is the cruelest trap of all. The moment you have employees and donors, other people's livelihoods and expectations depend on you not stopping, and you can't quietly walk it back. Every one of these feels like putting your good fortune to work, and every one of them quietly removes a door.
The charity one deserves a caveat, because I'm not telling you not to be generous. I'm telling you that building an organization is an irreversible commitment dressed up as a good deed. The you of next year might want to give in a completely different way, like a donor-advised fund, a few large gifts, or a check to someone who already runs the thing well. Same generous impulse, totally different reversibility. Give through something you can redirect, not something you've made yourself the load-bearing wall of.
Purchases run on the same logic, and they're the clearest illustration of the whole rule. We bought a sports car, and after a while it was all friction. The insurance, the maintenance, the cleaning, the low-grade anxiety every time I parked it near another car. So we sold it, took a small loss, and the headache was gone in a weekend. That clean exit is the whole point. We made the wrong call and it barely cost us, because the door was never locked. A house is the opposite. In the US the sale takes 65 to 100 days, if you're lucky, from the day you start interviewing agents to the day you hand over the keys, and the work involved is in a different universe from dropping a car at the dealership. Building one from scratch is that several times over, with your time and attention tied up the entire way through.
The decisions we could walk back
Now compare all of that to the money we kept somewhere liquid.
We bought public stock positions that turned out to be more volatile than we had the stomach for, and I eventually realized I wasn't the expert stock picker I thought I was. We decided they weren't for us, and we were out the next morning. And yes, I know the obvious objection, because I had it too. Aren't the liquid things liquid precisely because they're volatile? You can sell the stock tomorrow, and the reason you'd want to is the same reason it dropped overnight. True. But that's exactly the point. Volatility you can exit is recoverable. A bad day in a liquid position costs you a small, known amount and hands you the right to change your mind. Illiquidity you regret just compounds, quietly, for years. The stock that dips is a paper cut. The fund you can't leave is the thing still bleeding in spring number five.
That's the whole difference. The real estate funds were wrong calls we're still paying for. The stocks were wrong calls that cost us almost nothing, because we could undo them. Same mistakes, completely different price. The only variable was whether we could get out.
The one rule
For anyone who's come into money they didn't have before, here it is.
For the first stretch, make no investment decisions at all. And if you absolutely must do something, only do things you can easily undo. Liquid over locked. Reversible over permanent. Before you commit to anything, whether it's a fund, a house, a board seat, or a foundation, ask two questions. How fast can I get out, and what will it cost me to leave?
Leave the irreversible decisions for the version of you who's had time to learn what you actually want. That person is coming.
Don't trap them.