After almost 25 years working for Silicon Valley startups, had about 150 reasons to want to get out of the rat race — the 150 or so days the various startups he worked for had him in cars and on planes, almost half a year on the road pitching software solutions in person.
If he needed more reasons, there were another three to consider.
“I have two daughters who I absolutely adore,” Matthews, founder of Clark Street Capital, told Michael Duncan of The Road to Financial Freedom. “And a wife who I adore. It turns out the three of them actually like me as well.”
He began flipping houses in New England … and discovered a new passion.
“I joke that I don’t drink, I don’t do drugs, so I guess flipping is my cocaine, right?” he said. “So that’s my vice.”
But there was a problem — once the flips were sold, he was back to square one, looking for the next flip. He was working just as hard, no closer to freeing up time to spend with his wife and daughter.
Matthews began to think bigger — buying and renovating C-class apartment complexes from negligent landlords. This time, when he renovated the property, the plan wasn’t to sell it to a family, but rather rent the units to families. Instead of being left with cash profit at the end of the deal, instead he had an appreciating, cash-flowing asset.
In 2018, Matthews and his wife quit their jobs to do real estate full-time. Their current goal is 1,000 units by 2025 … but in saying sayonara to Silicon Valley, Matthews has already achieved his most important goal.
“I get to go to every softball game and every swim meet,” Matthews said, “and every choral concert and every play. And I actually get to go out with my wife every once in a while and have a dinner date and catch up and see how things are going.”
“I got 150 nights back with my kids and my wife,” he said, “and that was the ultimate freedom.”
