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.”
The Purple Bible
A chance encounter with — you guessed it — the “Purple Bible,” Rich Dad, Poor Dad by Robert Kiyosaki, changed everything for him. Matthews was determined to go into real estate … despite the fact that he had barely a clue of what he was doing.
“I had all the classic excuses,” he said. “‘I don’t know where to find the deals.’ ‘The world economically is cratering.’ And I was the one that didn’t have enough courage in myself to be able to hunker down and find the deals.”
But Matthews eventually found the courage. He began flipping houses in New England … and discovered a passion he had almost forgotten he had.
“I had an affinity for real estate,” Matthew said. “My dad was a master carpenter, although he never did it as a vocation … Some of my earliest memories are handing him a hammer at a porch that we were building for a friend of his.”
A chip off the old block, Matthews found that he loved taking worse-for-wear New England houses for a song, making them beautiful again, and selling them to a happy family for a profit.
“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.”
From Flipping to Building a Portfolio
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.
Best of all, it still had the appeal of doing good in the community — in this case, doing such a good job with renovation and tenant services that a long-standing tenant who was going to vacate instead decides to renew their lease.
“One of the things that really fires me up is when somebody lets us know that they wanna stay for another year,” Matthews said. “It’s awesome. That has to be a good feeling. It’s a high five in our office.”
Short-Term Pain, Long-Term Pleasure
Sometimes it’s a sales job — at which point, Matthews finds himself unexpectedly drawing on his background as a Silicon Valley software salesman.
“A resident who has lived in a C-minus class building,” Matthew said, “[the landlords] disrespect and don’t serve their residents … and the pain of that is, is palpable. And so when you come into that kind of situation, you’re looking to reset the relationship.”
“What I’m looking to do is say, ‘Yes, I understand and I hear you, and you’re right that this was a painful process.”
“However, if you just stick with us for the next 60 to 90 days, you’re gonna see the pleasure part of this, which is we’re gonna make everything brand spanking new. We’re gonna fix everything. And you know, in very short order, you’re gonna be really happy where you live and we’re actually gonna return your phone call.”
Winning The Game
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.”
