David Pupo did not set out to become a coach and mentor to real estate investors. Junior or novice investors simply noticed his runaway success — over 300 transactions and a big portfolio of rental properties, accumulated using his signature “Triple Offer Method,”  — and asked him for advice. 

He started charging for his time when he realized that these early students were asking a lot of him, but it wasn’t entirely about the money. Pupo had enough money.

“One of the biggest [reasons students pay me] is accountability,” Pupo, founder of tripleoffer.com, told Michael Duncan of The Road To Financial Freedom.  “If you want to pay for my time to teach you something, you gotta hold yourself accountable.”

Unfortunately, from his perch as a teacher and mentor, Pupo had to watch many students never get their investment careers off the launch pad, despite having everything it took to succeed in the business. The culprit — fear of failure.

“What holds a lot of people back is thinking that they’re gonna get it right the first time,” Pupo said. “I don’t know where that got instilled in our society where somebody had to be perfect … but somehow it’s there. And it’s very sad, because you’re seeing a lot of people that are very talented, but they’re afraid.”

Pupo has certainly made his share of mistakes — from mismanaging a property to trusting the wrong partner. And he still managed to come out of it financially free at a young age. 

“I’m a big basketball person,” he said. “You didn’t just wake up and go ten for ten from the free throw line. That’s a skillset. You have to develop it.”

The ADHD Investor

Out of college, Pupo found himself working sixty hours a week as a recruiter for defense contractors in his home base of Orlando. Burnt out at the end of the day, he became a self-described “couch potato,” until his soon-to-be-wife urged him to make a change.

Raised in Florida in a family of wall-to-wall real estate professionals, Pupo had had front-row seats for the housing crash of the Great Recession of 2008. Desperate for an exit ramp from his soul-killing day job, he became an obsessive listener of the Bigger Pockets podcast. He networked with real estate investors.

Their accomplishments floored him. “Sometimes they’d be making like $20-30,000 on deals and they would only have to put in a few hours of work,” Pupo said. 

In 2016, having saved up three months’ worth of expenses, he quit his day job and devoted himself full-time to real estate.

It wasn’t easy going at first. “One of my biggest hurdles, in the beginning, is that I do suffer from ADHD,” Pupo said, “and real estate, I realized, was ‘Alice In Wonderland.’ You go into this hole and you open out and there’s a whole different world that you never knew.”

Eventually, though, Pupo found his footing. “I think the realization was when you cash your first check, or you get that first wire hit,” he said. “You’re working in fog right now. You’re spinning, you’re putting a lot of hustle into something, and then suddenly … when you cash a check, something happens in your head … and your mind is showing you ‘This can work.’”

Three Offers are Better Than One

Pupo didn’t invent the Triple Offer Method, but it has become his secret weapon. It’s a strategy whereby you present a motivated seller with not one offer, but three offers, each one structured differently.

The point isn’t even the fact that you’re more likely to get a “Yes” with more offers on the table. The Triple Offer Method also elicits valuable information from the seller as to why they want to sell, and what it will take to close the deal. 

“We remove ourselves from just pushing one offer on a seller,” Pupo said. “I want to be able to understand what is [the] real motivation of a seller. So what we do is we provide three offers. Sometimes, heck, I’ll even go four, but ‘Quadruple Offer’ doesn’t sound as cool, right?”

So what would a “triple offer” look like? It might be:

  • A low “all-cash” offer.
  • A middle-of-the-road offer with financing.
  • A high offer with the stipulation of seller-financing.

Pupo sees seller financing becoming a bigger deal now that banks are crashing and credit markets tighten even more.

“We are now seeing, literally, banks collapse on themselves,” Pupo said. “Why not be able to use the seller as the bank as opposed to [going] to Silicon Valley Bank?”

Listen to the full podcast with David Pupo