Whitney Elkins-Hutten transitioned from live-in flips to long-term rentals for better cash flow. She built a 36-property portfolio that generated enough cash flow for her to quit her job. Eventually, she shifted her strategy again: from rentals to partnerships on bigger deals.
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You can opt-out at any time by visiting our Preferences page or by clicking "unsubscribe" at the bottom of the email. Advertisement Whitney Elkins-Hutten bought her first property, a single-family home that was "a little rundown" and needed some elbow grease, in Fort Collins in 2002. "I paid my friends in beer, sushi, and pizza and rehabbed the property," the Colorado-based investor told Business Insider.
"We took it from it being 1960s, green shag carpet, psychedelic daisies painted all over the walls to a really beautiful property." This story is available exclusively to Business Insider subscribers. Become an Insider and start reading now.
Have an account? Log in . About a year later Elkins-Hutten sold the property, walked away with "a $52,000 check in my pocket," she said, and started thinking about her next deal. Nearly two decades later, she invests in real estate full time and considers herself financially free.
She's also a financial educator and the author of " Money for Tomorrow ." Advertisement Financial independence, which she describes as having "enough passive income coming in to cover your current lifestyle," is distinct from financial freedom. She considers the latter a step up, and defines it as having "enough passive income coming in to cover the lifestyle that you want.
" Her investment strategy has evolved over the years. After her initial flip, she and her husband did a few "live-in flips," a strategy that involves living in the property while rehabbing it. It can help you save on living expenses and avoid capital gains tax on the sale of the property (if you live in it for at least two years), thanks to an IRS rule known as the Section 121 Exclusion .
Related stories While live-in flipping helped her build equity, it didn't produce cash flow. "After doing a couple of live-in flips, I was like, how are people retiring off of this? I don't quite understand because you're just getting buckets of money periodically," she said. Advertisement That realization prompted her first strategy shift: from live-in flips to long-term rentals.
It was an idea planted by one of Elkins-Hutten's friends, who suggested she keep one of her investment properties and find a long-term tenant, rather than sell it for profit. It was a good reminder that there are multiple ways to invest in real estate. Elkins-Hutten used real estate investing as a vehicle to achieve financial freedom and gain back time.
Courtesy of Whitney Elkins-Hutten "Here's where I see a lot of investors get in trouble: They borrow somebody else's investing plan and don't really think through if that plan actually works for their goals," said Elkins-Hutten, who admitted to making the same mistake and mirroring the plan of a friend who had a different timeline. After thinking about her goal — to have enough income coming in to leave her day job — Elkins-Hutten realized it required cash flow. She and her husband started buying single-family homes in 2016 in Colorado, where they lived, and eventually in Indianapolis and Kansas City, where they found they could get even better cash flow.
Advertisement They scaled to 36 single-family homes primarily using the BRRRR (buy, rehab, rent, refinance, and repeat) model. The long-term rental strategy ultimately helped her achieve financial independence and allowed her to leave her tech job in 2019, but it was labor intensive. "The 36 single-family rentals are a lot of management, even if you have a property manager," she said, adding that she probably bought too many.
"I argue I probably shouldn't have gotten the 36. I should have recognized earlier that I wanted my time back, my attention back, because I have a daughter at home that I really wanted to spend time with." The question became, "How do I scale a real estate portfolio that's going to serve me — not me serve it?" she said.
That led to her next major strategy shift: long-term rentals to partnerships on bigger deals, in which she could put up her money and take on a more passive role. Her first partnership was on a 52-unit apartment building, which she calls "the transition investment," as she still owned her single-family homes. Advertisement "I was like, wait a second, I've got 52 units over here, the cash flow is just about like my 36 single-family rental portfolio and far less overhead," she said.
"I thought, I need to go bigger to go faster — and to save my sanity. That's when I got into partnership." At that point in her investing career, she had the capital required to go in on big deals.
"I had so much money coming back at me, which is a great problem to have, so I needed a place to put it," said Elkins-Hutten, who eventually sold all of her long-term rentals. Plus, "I wanted to diversify my portfolio outside of my own investing business and in other markets and other asset strategies. I wanted to have exposure to debt.
I wanted to have exposure to self-storage. I wanted to have exposure to mobile home parks." As of 2024, she said she is a partner in $800 million of real estate, including over 6,500 residential units and 2,200 self-storage units across 11 states.
Elkins-Hutten walked Business Insider through a substantial part of her passive portfolio via screenshare. Advertisement While she's financially free and technically doesn't have to work another day in her life, she chooses to: "I left my job to be a full-time investor. I work harder than ever right now, but I don't have to work.
I get to work. It's a very different mentality.".
