How Two Finance Pros Actually Invest Their Own Money

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.

Nina O’Neal: From Financial Stress to Stability

I’ve had a complicated relationship with money for as long as I can remember. Growing up in North Carolina, money was a constant source of stress, especially after my parents divorced. My family was full of small business owners, so cash flow problems were a regular part of our lives. My childhood felt like a constant swing between having enough and not having enough.

By high school, I was working multiple jobs just to have my own money—it represented freedom. I made a promise to myself that I would never be financially dependent on anyone. Despite the instability at home, I was drawn to the stock market. I’d sit with my grandfather, poring over the stock pages in the newspaper. Once the internet came along, I started helping him and a local business owner buy stocks on E*Trade. For me, trading stocks in my mock Yahoo! portfolio felt like a fun game, completely separate from the real-world money struggles I knew. I had no idea how much that perspective would change.

After college, I moved to New York City with a dream of living there since a high school field trip. I landed a PR job in fashion for $33,000 a year. In Manhattan, my rent alone ate up more than two weeks of my pay after taxes. I loved the city, but over the next year and a half, I racked up serious credit card debt. I was 22 and living for the moment, figuring I’d deal with the consequences later. My answer to any social invitation was always “yes.”

Inspired by friends in finance, I decided to pivot my career to Wall Street. I got a job at an institutional money manager and learned an incredible amount about corporate finance and disciplined investing. It was here that I finally started to get my own finances in order. It wasn't just about making more money; I was finally understanding the fundamentals. Watching my savings grow and my debt shrink felt empowering. This experience lit a fire in me for helping others understand personal finance, which is what I still do today.

My journey from North Carolina to New York and back shaped everything about how I see . It’s no longer a game; it’s a powerful tool for reaching long-term goals. When the financial crisis hit, my training program at Merrill Lynch was cut, which felt like a career-ending disaster. But it turned out to be an opportunity. I ran into my now-business partner, who encouraged me to join him in starting our own firm. Today, we co-own a boutique financial planning and investment management company.

My husband is also an entrepreneur, so our income can be unpredictable. With two young sons, my biggest financial concerns are managing cash flow, taxes, private school tuition, and saving for college and retirement. This is where a solid grasp of becomes essential.

To manage it all, I use multiple Capital One 360 accounts labeled for specific purposes like “taxes” and “tuition.” This visual separation helps me track big expenses. For our mid-term and long-term goals—like college and retirement—we invest. We have an automated draft that moves money from our checking to our joint brokerage account each month. Because I prefer not to manage my own accounts, I use third-party money managers who handle the strategy. My approach to is pretty aggressive, and I rely on dollar-cost averaging through these monthly contributions, mostly in mutual funds and ETFs.

For my kids, I opened 529 College Savings Accounts right after they were born, with automatic monthly contributions. As a small business owner, I use a SIMPLE IRA for my retirement savings, which is also managed by a third-party firm. But my single biggest investment has been my business. For 11 years, we’ve reinvested in our company, and the return—not just in profit but in personal fulfillment—has been worth every penny.

Debbie Freeman: Using Debt and Discipline as Tools

I grew up 2,035 miles from Wall Street. My parents were among the 45% of Americans who don’t own stocks. Watching them struggle taught me the importance of having options. It’s hard to plan for the future when you’re worried about today, and that lesson became the cornerstone of my relationship with money.

I’ve never been afraid of using debt wisely. A $5,500 bank loan got me my first car, and student loans paid for my education. For me, debt was a ticket to independence. I still use it responsibly today. My student loan interest rate is just 1.74%, so I have no desire to pay it off early; that education was the best investment I ever made in myself. My mortgage is less than I’d pay in rent and has allowed me to build equity in Denver’s real estate market.

My first brush with happened when I was 15, working at a coffee shop. A regular customer named Roy would have me pick a stock from the newspaper each weekend, research the company, and report back. It felt like a game, but he nurtured my interest in finance and inspired my career as a financial planner.

Today, I channel that early curiosity into my Roth IRA, where I buy individual stocks of companies I understand and use in my own life. I also contribute to a SIMPLE IRA through my firm, which is invested in a mix of ETFs and mutual funds. It’s not flashy, but it’s a privilege to have a company plan, and it gives me a sense of gratitude and security. For anyone wondering , a workplace plan is a fantastic entry point.

This whole journey is a , and a big part of it involves investing in myself. About 10% of my pay goes into an online savings account to fund my annual equity purchase in my firm. As a divorced mom, it’s not always easy, but writing that check each year is a source of pride. It shows my daughters that women can thrive in finance.

My approach to and personal goals was deeply changed when I lost my brother to suicide in 2014. I realized I’d spent my life doing what I was “supposed to do” but hadn’t taken time for travel and adventure. That loss was an awakening. Now, I make saving for experiences a priority—whether it’s a family vacation or a trip to Paris. This disciplined saving is part of my overall philosophy on and pros alike: don’t get so fixated on the future that you forget to enjoy today.

We all have a different roadmap. Mine is built on accepting risk, acting on opportunities, and staying consistent with long-term goals. This is more than just ; it’s about building a life with options.