My real education in finance came from two people: my father and my first boss, David Swensen. My dad lost his parents young and had to put himself through college and medical school with very little. When some family friends passed, they told him about stocks, and he bought IBM in 1959. Even when life felt like it was taking everything from him, he held onto those shares. He still has them.
It’s a bit surreal to be asked how I invest my money. I grew up poor in rural Maine with my step-grandfather, and from ages 11 to 14, I was homeless, bouncing between neighbors' houses. So, at 43, being in a position to share my financial strategy is something I don’t take for granted.
I grew up in a house where financial literacy just wasn't a thing. We faced some tough lessons because of it, sometimes having no bank account at all, other times relying on check-cashing spots. I can’t bring myself to speak ill of the lottery, because scratch-off tickets were what got us through more than a few tight spots. The truth is, I was 26 years old before I even knew the stock market was a real thing.
My wife’s grandmother, Mimi, was in a drab hospital room in North Jersey, caught somewhere between her 89th birthday and the end of her life. It was a cold January day, and it didn’t really matter which one came first—the outcome felt the same. She had already lived two decades without her husband, Pop, much of it with failing health and vision. Mimi was ready. Her family stood by her, a testament to the life she’d built. The room was packed with her four children, ten grandchildren, and eight great-grandchildren.
As someone who co-founded a wealth management firm overseeing more than a billion dollars, runs a financial blog, and regularly appears on CNBC, I get asked one question all the time: how do I invest my own money? The short answer is that my approach is a blend of different strategies. I use a mix of active and passive investments, holding everything from mutual funds and ETFs to individual stocks and even private assets. But if there’s one consistent theme, it’s that I’m in it for the long haul. You won’t find me day trading or swing trading—frankly, I’m not good at it, and I believe those activities demand a full-time commitment I’m not willing to give. My priority is building and running my company for my clients and employees. So, when I decide on into something, I plan on staying there.
In a rare moment of unity, American politicians seem to agree on one thing: big tech is bad. From Senator Josh Hawley on the right to Senator Elizabeth Warren on the left, the calls to rein in or break up major tech companies are getting louder. They’re tapping into a classic David-and-Goliath story that plays well with the public.
I’ve spent a lot of time making the case for technology stocks, so it’s a bit ironic that my whole investment journey started with HEICO, a company that’s anything but digital. It was HEICO’s combination of a low-cost advantage and a tiny slice of a massive market that really opened my eyes. It taught me to hunt for businesses with both a competitive moat and the potential for exponential growth. As it turned out, when I applied this lens to the market in the early 2000s, about 90% of the companies that fit were in tech. But that other 10% was fascinating.
To be successful with , you have to know what a business is worth. But what if the old rulebook for valuing companies is broken?
If you look at Alphabet (Google's parent company) and Amazon, you might assume Alphabet is the better business. It's mostly software-based and doesn't require a lot of physical assets to run—a model of a modern, efficient company. Amazon, on the other hand, has old-school bones. It has poured billions into building out a massive physical network for its e-commerce business and has done the same for its cloud computing arm, Amazon Web Services.