At the age of 27, Kent Clothier was on top of the world. He was running an 800-million-dollar company, working 15-hour days, and living with all the trappings you might expect a 27-year-old millionaire to indulge in.

Less than five years later, he was bankrupt, unemployed, and grappling with the fact that for the past few years he'd been, in his own words, "about as big a douchebag as you can be."

Today, Clothier and his family run a total of six separate multi-million-dollar companies, several of which have landed on the Inc. 5000 at the same time. Two of their most notable ventures include a real estate investment company and a real estate investment education company, Real Estate Worldwide, that has served upwards of 50,000 students over the past 10 years.

A self-proclaimed "anti-guru," Clothier focuses on delivering business tactics, software, and other tools that are grounded in real-world business experiences and empower his students to craft their own legacy.

Along the way, he's learned a lot about overcoming failure and charting a course for sustained success in both the personal and professional realms.

From Riches to Rags and Back to Riches Again

Clothier got his start at the age of 17 in the arbitrage business. Along with his father, he would purchase truckloads of groceries in discounted regions and re-sell them to regions where the goods sold for a significantly higher price.

"We found inefficiencies in the market, and we addressed it. That's all we did," says Clothier.

Simple as the premise might have been, it was also lucrative: When Clothier reached age 30, the company was raking in $1.8 billion a year. By that point, he says, "I was full of crap. I thought the entire business was a success all on my own. I had never failed. I had the cars, the house on the water in Boca Raton, all of it."

And then Clothier was all but run out of the business. "I quit in a huff," he says. "I walked away from it. Over the next 22 months, I lost everything. I burned every bridge all the way down."

That's how, at the age of 32, Clothier found himself bankrupt and watching a late-night infomercial espousing how people could get rich buying and selling real estate. "I was just beat up enough and broke enough and motivated enough that I got involved," he says. He signed up for a real estate seminar and started learning about property flipping. "It was what I had just been doing in groceries," he says. "It made sense to me."

His ability to translate the lessons he'd learned in the grocery arbitrage business to the real estate industry paid off quickly. Eighteen months after enrolling in his first real estate seminar, Clothier had flipped around 90 houses and made a million dollars. Inside of three years, he and his father and brothers used the same methodology they'd applied in the grocery business to grow a thriving real estate company. "I was back," he says.

Seismic Attitude Shift

The business tactics may be similar, but the way Clothier has approached his current ventures is dramatically different from his old, "douchebag" ways.

"I'm not that guy anymore," he says. "It was very humbling for me to figure out that after I worked my ass off, how fast it can all disappear." As it turns out, business success is not akin to a built-in security system for life. It's merely a piece of it, and it can disappear at any moment. So it's important not to invest all of your eggs in your company's basket. "It taught me the importance of balance," says Clothier. "Family and collecting moments--not collecting shit--is much more important."

As he's better prioritized his own well-being, Clothier has also committed himself to improving the wellbeing of others. Part of this emphasis rests on philanthropic initiatives via his The Time Is Now Project, which supports initiatives such as educating children and building villages in Haiti.

"This is what it's really about," says Clothier. "All that other stuff? Nobody cares. Nobody's gonna talk about me or my family in 50 years and say 'Wow, they helped me flip more houses.' But somebody absolutely may remember us for the impact we left on the world helping to educate kids [and] build villages in Haiti."

This groundedness has served Clothier well in his business. "It comes from understanding clearly what matters to you the most and then building the organization around it and setting healthy boundaries," he says. "That contrarian attitude in my business is so desirable that it's attracted business to me. I thought it would cost me the business. It's done exactly the opposite."

Thus, Clothier's latest successes have had a lot to teach him about the value of authenticity. "It's an ocean of mediocrity out there in business," he says. "I've definitely learned that [when you're] clear, relentless, and unapologetic for who you are--and you market from that place--it's pretty shocking how effective that is. People want to belong. If they know what you actually stand for and who you really are and they actually get to see the real you versus the polished-up version of you... it's shocking what that can do to your business. It's pretty amazing how an authentic message can cut through all the crap to your target customers."

Just what message is Clothier looking to share with his clients? Fittingly, it's that the time is now.

"The greatest gift that I can give to somebody is the knowledge that they are going to die," he says. "We've just got a very, very limited amount of time here.... There is zero point in living those days on somebody else's terms."

For Clothier, the best vehicle he's found for living life on his own terms is real estate, which is why his educational initiatives center around empowering students to craft lifestyles they love via strategic participation in the real estate market.

Ultimately, however, Clothier is less of a real estate evangelist than he is a self-empowerment evangelist. "Whether they do it in real estate or otherwise, I don't care," he says. "Really what I care about is waking up two million people and helping them understand that 'this can happen for you.' The dream is right there, and it's very real."

All people have to do, says Clothier, is commit to being the best version of themselves and going after their dreams with everything they've got. "Mediocrity is the enemy," he says. "It takes just as much effort to go through the day being great than to sit around and half-ass. You've got one shot at this thing."