EP 404: Hawaii’s Hopeful House Flipper Recovers From Homelessness & Drug-Addiction w/ Greg Gaudet (Part 1)


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Sometimes I need to hear a good comeback story — someone who’s been through the thick of it and persevered despite the odds being stacked against them. Greg Gaudet is that person. Not all of us struggle with addiction as Greg did.

But all of us wrestle with our mindset in some capacity. And today, we have a candid conversation about what helped him get through some of his struggles with the aim that it will provide hope for others who are struggling, too.

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About Greg Gaudet:

Being the son of a real estate developer, investing is in Greg’s blood. But his world was shattered after his dad died from pancreatic cancer when he was 14 years old. Unable to cope with the pain, Greg spiraled into addiction and got into serious trouble. After a lot of partying and using substances to numb the pain, he became addicted to Percocet, which eventually led to oxycontin and, ultimately, even injecting heroin which took him to lows he would never have imagined.

Some rock bottom experiences include being homeless, spending a short time in jail, overdosing, and even coming close to suicide – there was no light at the end of the tunnel.

Eventually, fighting to recover paid off, and after turning his life around with the unwavering support of his mom, Greg returned to a career in real estate, dabbling in appraisal, escrow, property management, and restoration.

Although he was earning below the median income and barely making ends meet, his discipline and desire to improve his life and get out of the rat race drove him to live below his mean so he could save between 30-50% of his income all along.

All of his roles helped prepare him for when the time came to realize his dream of being an investor. As the saying goes, “Luck is what happens when preparation meets opportunity” (-Seneca).

Today Greg owns and manages 17 rental units on the island of Maui with an average LTV of around just 30%, which produces well over solid six figures of cash flow. At the same time, he works on doing flips and wholesales that create the capital he uses to continue acquiring rentals to increase cash flow.

Greg’s Carrot site: Maui Home Buyers

Brady Winder

Host of the CarrotCast Podcast & Carrot's Content Strategist. Loves family, music, good conversation and all things Volvo.

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