Investment

October 13, 2025

Making Sense of Retirement Investing for Beginners

It might sound strange, but you're never too young to start thinking about retirement. The power of compounding is so effective that if you start in your twenties, you can build a significant nest egg with surprisingly little effort by the time you’re in your sixties. All it takes is a basic grasp of retirement plans and the decision to start now. The sooner you begin, the less you'll have to put away, all thanks to compounding and a long time horizon. You can’t count on Social Security to be your only source of income, but thankfully, there are plenty of other options out there.

Investment

October 12, 2025

How a Venture Capitalist Invests His Own Money

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 .

Investment

October 12, 2025

Money Is a Tool. This Is How I Invest Mine.

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?

Investment

October 12, 2025

My First Business Taught Me Everything About Investing

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.

Investment

October 12, 2025

My Approach to Stock Investing for Steady Passive Income

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.

Investment

October 12, 2025

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.

Investment

October 12, 2025

My Best Investment Was Starting My Own Business

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.

Investment

October 12, 2025

My Personal Investing Playbook After a Financial Reset

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.

Investment

October 12, 2025

My Four-Bucket Approach to Personal Investing

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.

Investment