Updated on March 17, 2023
“For years my wife and I followed the blueprint that so many of us were given,” Michael Sjogren said. “Go to school, get good grades, get a good job, go back to school, work really hard and save your money in a 401(k).”
But when their son, Caiden, was born with Childhood Interstitial Lung Disease, Michael and his wife, Krysten, found a major flaw in that traditional career path. The rare disease causes damage to the lungs and makes it difficult to breathe, among other symptoms. Any time Caiden went to sleep, he needed oxygen and constant monitoring.
Over his first 18 months, Caiden and his parents spent a lot of time at Boston Children’s Hospital about half an hour south of their hometown of Middleton, Mass. One day, after having been at the hospital for over three weeks, Michael realized he had burned through all of his vacation and sick time, but the hospital bills were continuing to pile up.
“At a time when my son and my wife needed me the most, I had to leave them and go back to my cubicle so I could earn a paycheck to support them,” he said. “That pain as a man and a dad and a husband was the worst pain I’ve ever felt. That day I made a declaration that I would find a way to build a business that would give my family the income that we needed without sacrificing our most precious asset: our time.”
At the time, Michael was working as a CPA in corporate America, but over the next nine months, he threw himself into researching options that would allow him and Krysten to stop trading their time for a paycheck. His search led him into real estate investing and passive income where he met a man managing short-term rentals. He showed him how his business worked and how he was able to generate meaningful profit per month per property without having to own a single house.
Rewriting Their Story
By this time, Caiden had begun outgrowing the lung disease, and the Sjogrens could finally begin planning their next chapter. Michael suggested buying a vacation rental. He told Krysten, “We need a vacation. We need time to unwind and spend time together.”
“When Mike initially told me he was interested in investing in real estate, my first thought was ‘Yikes, how are we going to afford this?’” Krysten said. “Mike is a numbers guy, so naturally he assured me that we would be ‘making money on our money.’” She trusted his instinct, and they agreed, on one condition: They promised each other they would spend at least three days there every month as a family.
So in January of 2018, they bought and renovated Chalet in the Sky, a two-bedroom cabin in Bartlett, New Hampshire with panoramic views of Mt. Washington. The home caters to couples and families like theirs with kid-friendly amenities and a pool.
Within months, the home was generating a profit, so he began offering management services to landlords with vacant properties. By November, he had signed his first management client.
Those services are now known as Occupied, a tech-enabled property management company overseeing 24 properties in five different destinations from New Hampshire to Florida. Occupied partners with local housekeeping and maintenance teams for property care. Everything else is automated with software and smart technology, leaving Michael to spend just two hours a day on property management tasks.
Their new freedom opened another door of opportunity late last year: the purchase of a 13-bedroom beachfront boutique inn on Boston’s north shore. The Sjogrens and their partners renovated the inn throughout the Covid-19 shutdown and will be reopening this June as The Cove at Rockport.
Paying It Forward
Their rapid success hasn’t gone unnoticed. After several people reached out to him for advice, Michael decided to launch Short Term Rental Secrets, an education and financial coaching program that teaches others how to generate income through short-term rentals. He now has more than 150 students across the world who actively work in the space.
“I love teaching,” Michael said. “It’s just something that really lights me up.” Occupied gives him the time and freedom to pursue it and help others chase their passions. “I love how this industry has lowered the barrier to entry to becoming an entrepreneur,” he added. “It really opened up so many opportunities for people to take back control of their time and finances and really focus on what they want to do.”
Michael lives what he teaches. In August 2019, he reached financial independence with Occupied, fulfilling the vow he made that day in the hospital. In November, he quit his CPA job and now runs Occupied and STR Secrets fulltime.
Quality Over Quantity
Krysten was also able to leave her full-time job in residential property management. Previously, she oversaw design and furnishing for their clients’ properties in her spare time. Now, she is Occupied’s Head of Marketing and Design.
“Mike and I were both working 50- to 60-hour weeks, consistently,” she said. “We had to heavily rely on our family to watch our baby and it broke my heart. I would be on a plane traveling for work and would silently sit there with tears in my eyes as I scrolled through pictures of my son. I missed out on bedtimes, bath times, bike rides around the neighborhood, and snuggle time.”
She now has the flexibility to work on her own time and can focus on quality time with Caiden. “Being a mom is the most fulfilling job in the world and am so blessed for the life we have created,” she said.
The Sjogrens have kept up their promise to each other to visit their vacation rental at least once a month. Michael’s parents joined in on the fun, too. They purchased the home next to their New Hampshire chalet, and the rental income allowed his mom to retire.
And this fall, they’ll celebrate the three-year anniversary of Caiden no longer needing oxygen. The four-year-old now runs back and forth through the yard from his “mountain house” to “Grammy and Grampy’s mountain house,” as he calls them.
Krysten said it’s his favorite place to go. “Seeing the pure joy on his face as we create these amazing memories is something we will always remember.”
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