Have you ever failed at anything? If you have, that failure may actually point you in the right direction and encourage you to take risks that payoff. After failing at college, Tom Cafarella thought about what he wanted to do – earn enough passive income to not have to work. He has built up a passive income portfolio to where he does not have to work much. However, it turns out that he loves to work and puts in 80-90 hours each week because he enjoys real estate so much.

Tom had strong mentors in his life to show him the way to make his dream of passive income come true. While growing up, the only person he knew who had a decent amount of money was his grandfather, who worked minimum wage jobs his whole life. But the one thing he did do was buy multifamily real estate in and around the Boston area. He was the only person Tom knew that really didn’t have to work that hard. Tom decided to follow in his grandfather’s footsteps. He decided to go after it because he always wanted to be a passive income investor and buy multifamily properties.

Topics on Today’s Episode:

  • When starting a business, you’ve got to be prepared to get your teeth kicked in – doesn’t matter who you are, how smart you are, or how hard you work
  • Find a mentor because you’ll get kicked in the teeth less, if you have somebody who’s already been through the fight
  • Tom has multiple streams of income, and every single one has been taught to him by somebody
  • Right now, there’s a ton of money being made on the fix-and-flip side of the real estate business; things change, so even out your cash flow and be nimble
  • When most successful entrepreneurs use a system that works, just follow it and model success; don’t try to recreate the wheel
  • To survive when things aren’t working, find a new plan and shift gears; what’s the fastest way to cash?
  • Prime capital to deploy, buy strategically based on cash flow and model, and have infrastructure in place to efficiently make money when change happens
  • People who are not seasoned operators overpay, and a tweak in the interest rates changes a whole paradigm for a lot of people
  • Everybody was buying with crazy loans, and nobody was renting, so rents decreased; prices are too high, but there’s no good alternative, if they start to fall
  • Tom is doing development because they’re brand new and easier to manage
  • Tom’s private money comes from a lot of different sources: Levering out personal assets, owning rental properties, refinancing, and utilizing average individuals
  • It’s harder to raise capital in the beginning because people want to see a track record; once you have one, it becomes much easier to point to your successes

Links and Resources Mentioned:


“I’m a pretty entrepreneurial person, very entrepreneurial. It (college) was kind of just like trying to fit a square peg in a round hole type of thing, and I wanted to get into real estate.” Tom Cafarella

“If you can model what other successful people do, it gets you there so much faster.” Corey Peterson

“I think that anybody who’s in real estate is very fortunate because most professions, people get up, they hate what they do, but real estate is truly fun.” Tom Cafarella

“You’ll get kicked in the teeth less, if you have somebody who’s already been through the fight themselves.” Tom Cafarella

Don’t forget to download my Free Workshop Quickstart Video Series, and if you like what you have heard please leave a review on iTunes.

Text the word MONEY to 408-500-1127 to get my free private money program and credibility kit for single family.