How '4-Hour Workweek' author Tim Ferriss went from a struggling entrepreneur to a bestselling author and podcast host with millions of fans

"I'm very comfortable being 40," Ferriss said. "But as a thought exercise, you know, I asked myself, if this is the halfway point, if we're just looking at the actuarial tables, it's like, all right, if I'm at 50%, right, I'm halfway through this race called life, and when I hit the finish line, you're dead at 80, how might I want to rethink trajectory?"

"How might I want to rethink over-planning versus under-planning? Even though I'm trying to improve my relationships with others, are they dependent on my relationship with myself?" he said. "If so, how should I even conceptualize improving that, right? If it's never been part of my repertoire?"

As he figures out answers to these questions, he explained, he's going to take his audience along for the ride.

The podcast is a perfect encapsulation of Ferriss' brand.

As he puts it: "I specialize in pattern recognition and accelerated learning. So taking a subject that seems very complex or that can be presented in a very complex way, and distilling it down into the fewest number of moving pieces that really matter."

Ferriss was devastated when the show ended, but eventually decided he would find a way to get his product out there, the same way he did with his last book.

In 2015, he finally won the digital rights to all 13 episodes of the show and distributed them on iTunes, where they topped the most-downloaded chart.

Ferriss said that the energy he put into the book — it's a giant one, and is loaded with photos and graphics — combined with the unexpected distribution challenges burned him out. He decided to take a break from writing, aside from publishing posts on his popular blog.

This book helped establish Ferriss as a "human guinea pig" and began a pattern he would continue to apply to other fields.

He would talk to experts to create a weight loss diet, for example, and then try it himself, sharing his results along the way. He would encourage his readers to share their stories as well, and to offer suggestions for improvements if they noticed any.

Ferriss was an adept student and had a very successful run as an early stage investor and adviser, but he decided in 2015 to refrain from making more investments so that he could focus on his own businesses.

Ferriss had been deemed Silicon Valley's new productivity guru, becoming something of a Tony Robbins-esque figure.

It was then that Ferriss discovered the ancient Roman philosopher Seneca, whose Stoic ideals have since helped him move through low points.

In his 2017 TED Talk, he said that he especially focused on Seneca's line, "We suffer more in imagination than in reality.

When he took time off, he realized that his business was actually performing better without his micromanaging, and he extended his trip to Spain.

During this sabbatical, Ferriss compiled lessons around efficiency and planning he had learned from both his professional and personal struggles, and these would later form the basis for his 2007 career-defining book, "The 4-Hour Workweek."

Ferriss told us he created his own athletic supplement company because it was an area he was obsessed with in his own life. He decided to combine supplements he was already taking while working with college athletes to determine where the biggest demand was.

"BrainQuicken was a real learning on the job MBA," he said.

One of his Princeton professors would later invite Ferriss to speak to students about what he learned as an entrepreneur. It culminated in a lecture Ferriss cheekily called "Drug Dealing for Fun and Profit."

Ferriss said that he was in a "very, very dark" time as a college senior and even contemplated suicide.

He took a year off, teaching Japanese and working odd jobs in China. When he returned to finish his degree, he was certain that he would not take a traditional Ivy League path into finance.

"I saw my classmates competing, because that's what they were good at!" he said. "I mean, you take kids who go to a school like Princeton, they're used to competing, and they are used to being number one, so if something seems coveted, they will compete for it, whether or not they really want that thing."

Ferriss' trip to Japan was his first time traveling abroad, and he said it was "a huge formative experience in my life."

He considers this part of his life to be an awakening to the realization that there was a huge world beyond where he grew up, and it fostered his passion for exploring other cultures.

Ferriss was small for his age as a child, and he said kids would pick on him because of his size. When he was around eight years old, his mom signed him up for wrestling classes, a sport that laid the foundation for his love of experimenting with workouts and diets that he would develop as a teenager.