Once you have the keys to your home, a new set of financial questions often emerges. You might be thinking about refinancing your mortgage to lower your payments, pay for a big home improvement project, or consolidate other debts. Maybe you’re wondering when the right time to refinance is, how to pay your mortgage off faster, or even what to do if you’re facing the possibility of foreclosure.
Buying a home is easily the biggest purchase you'll ever make. For most of us, it’s also an incredibly emotional and stressful journey. There’s a mountain of information to digest to make smart decisions, from figuring out if ownership is right for you to understanding the fine print on a mortgage. Think of it as the ultimate ; it requires careful planning and a clear understanding of how you're for the long term.
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?
Before I became the Founder and CIO of Capital Innovations, before my work was featured in , and long before I wrote , I was the youngest of five kids growing up south of Pittsburgh. My worldview wasn't shaped in a classroom; it was forged at the family dinner table.
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.
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.
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.