I’m Retiring a Multimillionaire: Here Are the 3 Best Real Estate Decisions I Made in My Life
Written by
Martin Dasko
Edited by
Zuri Anderson
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According to the monthly housing report for December released by Realtor.com, the median house price was $399,950, marking the first time since March 2022 that the median listing price was below $400,000. If you’ve been waiting to get into the real estate market, this may be the right time for you to make a move.
On another note, a Schroders report found that only 40% of retirees believe they have enough money for their golden years, and 62% said they had no idea how long their savings would last. With living costs rising, it’s clear Americans will need to be more aggressive with their retirement savings.
If you’re looking to build a real estate portfolio to provide financial security in your retirement, you may be thinking about starting now, with interest rates expected to drop in 2026. GOBankingRates spoke with a multimillionaire who’s close to retiring to learn about the best real estate decisions they made to stack their income and ensure their retirement security.
The Best Decisions When Building a Real Estate Portfolio
Ryan Dossey, a real estate investor and the founder of Ballpoint Marketing, noted that he has built a portfolio of over 100 homes, flipped properties nationwide and owns a franchise flipping and brokerage company. While he’s not retiring just yet, he has lessons to share about the best decisions that led to becoming a multimillionaire through real estate.
Getting Into House Hacking
Dossey noted that he’s a strong believer in house hacking to get into real estate. He recommends owning a property and renting out a section of it.
“This could be a basement apartment or an ADU (accessory dwelling unit),” he explained. “My current home in San Diego has a ‘junior adu,’ which is smaller than 500 square feet, and we lease it to help offset our living expenses.”
If you’re not ready to invest in a rental property, you can start by turning your spare room or basement into an additional income stream. By getting started with house hacking, you can keep a close eye on your tenants and care for your property since you’ll be around. By getting started through this method, you can test the waters.
Finding Clients Through Direct Mail
Dossey credits his success to always finding his own real estate deals with direct mail. He added, “When I started out in real estate, I was either running into bidding wars or looking at other folks’ leftovers. By sending letters directly to property owners, I can pick what area I’m in, how old the property is, and make an offer that makes sense for me.”
Dossey shared that on many of these properties, he’s usually the only person the seller speaks with. He believes in full transparency, with no haggling or pressure. The success of his system led him to launch his own real estate marketing business, where he sends mailings for other investors nationwide to diversify his income. Working directly with sellers helped him secure better deals and the ball rolling with his real estate portfolio.
He Stopped Taking the Fast Cash
Dossey admitted that for house flippers, it can be tempting to remodel and sell everything to chase the quick money. However, he notes that he built a real estate portfolio by keeping the best and flipping the rest. He elaborated, “We converted a lot of properties into long-term rentals and benefited greatly from the appreciation and tax benefits (depreciation).” By holding on to properties and keeping them as passive income streams, he has built a portfolio that can cover his expenses in retirement.
How Feasible Is This for Everyday People?
Dossey believes real estate is the best vehicle for the average person to become wealthy, as you can leverage your savings and potentially achieve better returns than with any other asset. However, he warned that marketing directly to owners isn’t for everyone, as he’s had campaigns flop.
Dossey shared his best advice for the average investor: “You don’t have to do it full-time or as a career. Buying nice properties located in high-demand areas that pay for themselves is the cheat code. My first year, I wholesaled a few houses and rolled those profits into down payments on my first two rentals.”
If you’re looking to get started in real estate, you’ll want to focus on closing your first property so that you can get into the game. You can begin by making an offer on a property in a community that you’re familiar with, so that it’s not that big of a risk for you. As your property appreciates in value, you can start to look into making bigger deals and trying to move up so that you can land a property with more units.
The goal is to ensure your real estate portfolio generates positive cash flow, providing an additional stream of income and an asset you can potentially sell in the future to secure your retirement.
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