If you’ve ever wondered how to build wealth through both the stock market and real estate investing while keeping your financial strategy balanced, this conversation is for you. I sat down with Ali Swart, a Certified Financial Planner with nearly 16 years of experience and an investor for over 18 years. She grew up in a lower-income family and learned early on the importance of financial stability. Ali started her investing journey in the stock market and later expanded into private money lending, multifamily private equity, and even cryptocurrency. In this interview, she shares her insights on diversification, making passive income work for busy professionals, and the lessons she’s learned along the way.
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Hey everyone, I’m Adrienne Green, and today I’m here with Ali Swart. I’m so excited for this conversation because Ali brings a strong financial background to her real estate investing. She’s a Certified Financial Planner with years of experience in the industry, and she’s also an active investor in multiple asset classes. Ali, thank you so much for being here today!
Yeah, thank you so much for having me!
Ali, I’d love to start with your journey. How did you first get into real estate investing, and what inspired you to take that step?
It’s a great question. I grew up in a lower-income family. My parents both had stable jobs—my mom was a dental assistant, and my dad was a general contractor. You might think, “Oh, general contracting—great business!” but while my dad was incredibly skilled at his trade, he wasn’t as strong in business operations. So, the business was never wildly successful. I grew up seeing him work with real estate, whether it was roofing, siding, or home repairs, and I was exposed to the industry in a very hands-on way.
Another early exposure to real estate was through my grandfather, who flipped houses to help pay for my college. That was when I first started connecting real estate with financial growth.
I started my own investing journey in the stock market during my late teens and early twenties. I had some leftover student loan money and thought, “Why not invest this and try to make more than my loan interest?” That was my first real taste of investing. Later, I joined a company that offered an incredible 401(k) match and profit-sharing plan. With my contributions, employer matching, and profit-sharing, nearly 24% of my income was going into the stock market, which gave me a deep understanding of how investing worked.
Fast forward to my late twenties—my husband and I had built most of our wealth through the stock market, but one day, while reviewing our net worth statement, I realized it was time to diversify. Real estate was the natural next step, and we knew we needed exposure to it.
At first, I thought we would be long-term, multifamily residential investors. I started looking at duplexes, triplexes, and quads, focusing on the Pittsburgh market, where we live. Pittsburgh is relatively affordable compared to other markets, so it seemed like a great entry point. We did everything—due diligence, underwriting, submitting offers. But about six months in, my husband had a reality check moment and said, “Ali, how do you think we’re going to manage rental properties while working full-time and raising two kids?” At that point, our children were three and five.
It was a fair point! We were putting in a ton of hours analyzing deals but hadn’t closed on anything. That’s when we pivoted to private money lending and private equity investments. We realized we could still achieve our real estate goals but in a more passive way.
I love how you embraced diversification rather than the “stocks vs. real estate” debate. What are your thoughts on that?
Absolutely. As a Certified Financial Planner, I believe in diversification. Private markets have a valuable place alongside public markets. Growing up, my grandfather used to tell me stories about how my dad had so much potential and should have become a stockbroker, but he didn’t want to wear a suit and tie. Those stories stuck with me, and I think they shaped my interest in finance.
From my experience working with investors, I’ve seen that liquidity is key. The stock market offers liquidity, whereas real estate provides stability. I view them as complementary. Private money lending, for example, offers steady returns in the range of 11–15%, which can balance out the volatility of the stock market. That’s why we structured our portfolio to include both.
When you decided to go the passive route with real estate, how did you choose private money lending and private equity over other options?
It was all about using our wealth strategically. I wasn’t looking to replace my income—I love being a financial planner. Instead, I wanted to add stability to our portfolio. Around that time, I was reading The Hands-Off Investor (which dives deep into vetting syndications) and Who Not How. The latter book made me realize I didn’t need to be the one managing every aspect of my real estate investments—I needed the right people.
I started leveraging my network to find strong operators and solid deals. Our first private money lending deal was through a self-directed IRA. I had a significant amount of retirement savings from my old job, so I shifted part of it into a self-directed IRA to use for real estate. That allowed me to invest without worrying about the tax implications of private money lending, which is typically taxed as ordinary income.
How do you find your private money lending deals?
Networking! Every deal we’ve done has come from connections in investor groups. Our first deals were short-term—under 35 days—which helped us gain confidence in the process. I always ensure we’re in a first-lien position, have personal guarantees, and proper legal protections. Over time, we’ve expanded to longer-term loans with structured interest escalations to incentivize faster repayment.
You clearly have a well-organized approach. How do you track your financial progress?
I track our net worth quarterly using a simple Excel spreadsheet. It’s broken down into liquid assets (stocks, cash), illiquid assets (real estate, private money loans), and liabilities. I also use zero-based budgeting, where every dollar has a job. Our savings go into separate accounts for retirement, investments, vacation funds, and taxes, keeping everything clear and intentional.
What is a transformational system you’ve implemented in your real estate investing business?
Zero-based budgeting and net worth tracking have been game-changers. They help us make informed decisions about where to allocate funds rather than just “saving for the sake of saving.”
What’s your go-to tool for managing operations?
We consolidate most of our financial accounts with Fidelity for easy tracking. The only external account we use is a separate joint operating account for household expenses.
What book has been transformational in your investing journey?
The Hands-Off Investor by Brian Burke was crucial for learning about syndications. Who Not How helped shift my mindset on delegation. The Slight Edge taught me the power of small, consistent improvements, and The Lifestyle Investor by Justin Donald reinforced the importance of passive income.
Where can people connect with you if they want to learn more?
You can find me on LinkedIn or reach out through social media. I’m always happy to connect and share insights!
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