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.
It’s one thing to give financial advice, but it’s another to live by it. The way we handle our own money is often a reflection of our earliest experiences, biggest lessons, and personal values. Here’s a look at how two financial professionals, Nina O’Neal and Debbie Freeman, manage their own investments, shaped by their unique life stories.
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.
Money was a constant source of conflict in my house growing up. My dad made a good living, and my mom was skilled at spending it, but their relationship was strained for many reasons. Money just became the language they used for conflict and control. After they divorced, the arguments over alimony and child support dragged on for years.
It’s just after 4 a.m., and I’m already up. Today is shaping up to be a big one in the markets, with some serious volatility expected around 8:30 a.m., and I don't want to be late to the party. A strong cup of Earl Grey tea is helping me get dialed in as I get ready to scan the charts, maybe to make up for getting a late start yesterday.
Some mornings, the market is quiet. With little major economic news on the docket, you get a chance to focus purely on price action, which is a welcome change of pace. On days like this, the most important part of isn't finding a setup, but having the discipline to wait for one.