My grandpa was a realtor and my favorite uncle was a mortgage broker. Growing up, I was surrounded by people who made money through real estate — and I absorbed every bit of it.

So when I got out of school and started working, I had one financial plan: buy rental properties. Lots of them.

I never opened a 401(k), didn’t even know what a Roth IRA was or anything about index funds. Every spare dollar I had I socked away for my next down payment.

By my early 30s, I was the proud owner of seven rental properties — which from the outside sounds like a massive success story. But the truth is every new property I bought added more weight to my responsibilities and stress.

Owning seven rental properties is like running seven small businesses. Each comes with its own headaches, tenant issues, and liabilities to worry about.

Speaking of tenant issues… The breaking point for me was when I found out that one of my tenants was a “lady of the night” — and was running her business out of the apartment she rented from me.

That was the straw that broke the camel’s back. It forced me to step back and ask myself a question I’d never seriously considered before: is real estate actually the best way to build wealth? Or is it just the only way I’d ever known?

Real estate was all I knew — and that was the problem

This is probably more common than most investors realize. When you find success in one way to make money, that strategy starts to become the only path you can see.

I had serious tunnel vision on real estate, and it took me years to recognize my own bias. What finally cracked it open was meeting people in the FIRE (financial independence, retire early) community. These folks had built completely different portfolios than mine — with similar returns, great tax advantages, growing net worths — but none of the landlord headaches I was drowning in.

That’s when I started exploring tax-advantaged and brokerage accounts for the first time. I opened a Roth IRA and started maxing it out every year. I actually paid attention to my 401(k) at work. And instead of stock picking and timing the market I dumped all my money into low-cost index funds.

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When I ran the numbers, I was humbled

I went back and looked at my very first investment property — a little place I bought with my parents when I was 18. I compared its performance over 15 years of ownership against how the S&P 500 performed over that same period.

The result was nearly identical returns, around 9.5% average return per year.

That really stung. Instead of all the hustle and grind that went into that rental property, I could have earned the exact same return by just sticking my money into an index fund.

The tax advantages I’d been completely ignoring

I was a fool for brushing off tax-advantaged retirement accounts when I was younger.

A Roth IRA lets your investments grow completely tax-free. A 401(k) lowers your taxable income today while your money compounds for decades. These are tools I didn’t really understand the long-term power of because nobody in my real estate circle ever talked about them.

To be fair, real estate can have real tax advantages too — if you know how to play the game right. But for someone starting from scratch with a normal income and no real estate network, simple tax-advantaged retirement accounts are a way more accessible starting point.

What I’d do if I were starting from scratch

I’ve now sold six of my seven rental properties. I’m keeping one — partly for cash flow, partly for sentimental reasons. The majority of my net worth is now in index funds, and honestly, I’ve never felt more financially free in my life.

Here’s what I’d tell my 18-year-old self if I was starting again:

  • Max out your Roth IRA every year (2026 limit: $7,500, or $8,600 if you’re 50+). It can grow to over $1 million before your 50th birthday.
  • Contribute to a 401(k) if your employer offers it. And at minimum enough to capture any employer match — that’s free money.
  • For any additional savings, stick them in a regular brokerage account.
  • Invest in broad market index funds like a total market or S&P 500 fund.
  • Reinvest dividends and don’t touch it.

That’s it. No tenants. No toilets. No 2 a.m. phone calls.

If I’d done this from age 18 instead of chasing rental properties, I’d likely be in a stronger financial position today — with a lot less stress along the way.

Real estate isn’t bad and plenty of people build serious wealth with it. But it’s not the only path. And it might not even be the best path — especially if you’re starting out, working a regular job, and just want your money to grow over time.

The stock market lets me be a purely passive investor. I wish I’d given myself permission to take the easier route a lot sooner.

I personally use Fidelity and Charles Schwab for all my accounts. Both are beginner-friendly, charge no monthly fees, and give you access to low-cost index funds that track the entire U.S. market. If you’re just getting started, check out our list of the best brokers in 2026 to find the right fit for you.

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