My Rules for Investing in Things I Actually Love

After two decades in wealth management, with a background that spans from Georgetown Law to co-inventing the tech behind Priceline.com, I’ve learned that the most profound insights often come in small packages. We tend to think serious wisdom requires a dense, systematic narrative. But I’ve found that the ideas that stick with me most—the ones I still remember 20 years later—are often short, sharp, and to the point, much like the aphorisms of old thinkers or, in today’s world, a well-crafted tweet.

Instead of a lecture, an aphorism is more like a shared experience. It’s a humble way of saying, “Here’s something I’ve observed.” So, consider these my musings on the question of and, more importantly, how to live well. You can take them or leave them.

Invest Where You Have an Edge

Thanks to technology, public markets have become incredibly efficient. It’s nearly impossible to gain a legal informational advantage there. That’s why my interest has shifted to less efficient markets where an edge can be legally and easily found. I’m talking about areas like real estate, private businesses, venture capital, fine art, collectible cars, wine, and even cryptocurrencies. These are some of the spaces where the thrive.

Warren Buffett’s famous advice is to “invest in what you know.” I’d take that a step further: invest in things you love to own and are obsessed with learning about. My portfolio is heavily weighted toward tangible, hard assets—especially if I can get some use or enjoyment out of them.

My biggest single investment? My own business. I’ve always preferred to be in control. I’d rather be the driver of the car than a passenger on a bus with millions of others, just hoping we don’t crash. If I lose money investing in my own business, the blame is on me. When you invest in public stocks, it’s easy to blame outside forces, which fosters a victim mentality. Reject that path. Turning that initial effort from a is the ultimate form of control.

After investing in yourself, your next move should be . In my experience, it’s the second most reliable way to build wealth over the long term. My own holdings are diverse, from residential properties and farmland to industrial centers and self-storage, and the tax-adjusted returns have been exceptional.

Finally, invest in assets you genuinely love. For me, that’s visual art. It beautifies my life, it’s a fascinating field of study, and it happens to be a highly inefficient market where information advantages are significant. You can’t exactly hang an ETF on your wall, drive it, or drink it.

The Psychology of Abundance

I’ve noticed that people who are obsessed with their portfolios—checking them 10 or 20 times a day—often self-destruct in the long run. They’re too close, too emotional, and too tight-fisted with their money.

I follow a principle from Deepak Chopra’s work called the Law of Giving. The idea is to keep wealth circulating. Money is like blood in the body; if you cut off the flow with fear, suspicion, or stinginess, the system dies. Instead, keep the money moving. Be generous, take calculated risks, and invest in people you trust. This approach creates an energy of abundance that leads to better returns, both financially and spiritually. Karma is not just a factor in accumulating wealth; it's essential for preserving it.

This mindset is crucial for anyone ; you have to be willing to invest time and resources to see a return.

The Unspoken Rules of Wealth

When it comes to building wealth, people focus on the wrong things. They obsess over fees when taxes are the real drag on your returns, often costing you 20-35%. The U.S. tax code overwhelmingly favors two things: owning your own business and direct . My philosophy is simple: don’t fight the IRS. Go with their flow.

On a personal note, one of the best investments you can make is a solid pre-nuptial agreement. Divorce is an incredibly expensive and destructive financial event.

As for financial advisors, there’s an old saying in the industry: many are like cobblers whose own children have no shoes. After years of analyzing public markets, I now find them joyless. However, everyone should have an advisor, if only to serve as an unemotional sounding board for their financial decisions.

A Winning Mentality

Over the years, I’ve learned that the more people passionately hate on an investment, the stronger the buy signal often is. It happened when I bought multi-family real estate in 2009 and again when I started buying Bitcoin three years ago. You also have to get good at moving on. Holding onto a losing investment, hoping it will come back, has a massive opportunity cost and drags down your entire mental state.

Don’t grip your investments too tightly. Have a sense of humor, relax, and accept that you will take losses sometimes. This is true for stock picks and for building a alike.

A wealthy cousin of mine once told me over cigars, “I started 10 businesses in my life. Six succeeded and four were total failures. I’m rich because of that one-venture swing.” That's the reality for those seeking one of the ; it's a numbers game you win by surviving the failures.

Ultimately, when it comes to or your primary focus, the one who cares the least often wins.