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.

Later that evening, it hit me: my first memory of money was the offering plate being passed around at church. Week after week, I watched people willingly give their money away to support their community. I often wonder how that image shaped my own financial decisions. It certainly didn't stop me from pursuing a career in finance after falling in love with the markets in college.

From Stock Picker to Index Believer

Like a lot of people just getting into , I started out as a stock picker who looked up to Warren Buffett. Following his advice to “buy what you know,” the first stock I ever bought was Nordstrom. A few years later, I broke his other rule about holding “forever” when I sold it for a deposit on a tiny studio apartment in Manhattan. This was my first lesson in understanding for real-life goals.

My entire investment philosophy changed when my boss gave me a book called by Charles Ellis. The book’s core message was a revelation: trying to beat the market is, for most people, a losing proposition. Ellis argues that avoiding major mistakes is far more important than chasing huge wins. The market’s return is actually a great return, and with low-cost index funds, it’s available to anyone who is willing to accept it. I haven’t bought a single individual stock since.

The Leap to My Own Business

I’ve always made it a priority to save, starting with small contributions to my 401(k) just to get the employer match. Ten years ago, I took those savings and made the biggest investment of my life. I moved to New Orleans and decided to start my own financial planning and investment advisory firm.

To fund the and cover my living expenses with no salary, I used most of the retirement funds I’d built up over the first decade of my career. It was a terrifying leap, but it was the best financial decision I've ever made. While I wasn’t great at finding new clients at first, I started an through my blog and website to build my profile. That effort ended up being the most expensive but effective job interview of my life, getting me noticed on a national level. It was the ultimate transition from a professional job to a journey.

How I Invest My Money Today

Life has changed since then. I’m married with two young kids, so our financial priorities have shifted to saving for their education, a bigger house, and a future where we have the freedom to not work if we choose.

My strategy is built on the simple principle of paying myself first. A portion of every paycheck is automatically sent to my 401(k), 529 college savings accounts for both kids, and a cash reserve. My goal is to invest these funds for our long-term goals without ever really “seeing” the money in my checking account.

Here’s a look at the specifics:

• My portfolio is based on my long time horizon and high tolerance for risk. I keep 80% in stocks and 20% in bonds. The bonds are there to reduce volatility and give me cash to rebalance and buy more stocks during market downturns.
• The portfolio mirrors what I recommend to clients—a globally diversified mix of stocks and bonds using low-cost mutual funds and ETFs. We make tactical adjustments, like tilting toward international stocks if they seem cheaper than US stocks.
• Our kids’ 529 plans are in age-based Vanguard funds. These automatically become more conservative as they get closer to college age.
• Most years, I contribute to a Health Savings Account (HSA). It offers a rare triple-tax advantage, but you need a high-deductible health plan. With a new baby this year, we opted for a lower-deductible plan, but I hope to resume HSA contributions soon.

I make one small exception to my index-fund-only rule. I’ve invested a small amount in an ETF created by Perth Tolle called Life + Liberty Indexes. It invests in emerging market countries based on their human and economic freedom. I admire Perth and her thesis, so I made room for it.

My experience has taught me that is ultimately about funding your life goals. The “why” you’re investing is so much more important than the specific numbers. As long as I keep paying myself first and avoid making big mistakes, I’m confident my portfolio will get me where I need to go.