My day job is all about taking risks. As a venture capitalist at my firm, Social Leverage, my partners and I invest in seed-stage software companies, with my personal focus being on financial technology. You might recognize some of our early investments, like Robinhood, eToro, and Ycharts. This background, along with co-founding StockTwits, probably makes it clear why I favor individual stocks over index funds when it comes to .
After spending my career in behavioral finance, I’ve learned that how I invest my own money is either incredibly straightforward or deeply complex, depending on how you look at it. But my entire approach starts with a single idea: money is always a servant, never a master. For anyone wondering , I believe the first step is to ask a more fundamental question: why are you even saving in the first place?
I’m a dividend income investor—personally and professionally. It’s a simple philosophy: what I buy for my clients, I buy for myself. My approach to is built entirely around this principle. Now, I’ll admit I have a rogue position in Facebook that I picked up back in 2012 and maybe a few shares of Twitter from 2015 after hearing a compelling case from Bill Miller. But that’s where my dalliance with growth stocks ends.
A few years ago at a conference, a speaker asked the audience, “What is your first memory of money?” I drew a blank. The question is important because our earliest experiences with money form deep-seated beliefs, or “money scripts,” that guide our financial lives without us even realizing it.
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.