08/10/2011 03:28 pm ET Updated Oct 10, 2011

The Life Out Loud: One Man's Journey From Baseball Champ to Rock Star to Entrepreneur

It was a Wednesday afternoon around 2pm. I'd just bought a big screen TV and was watching some stupid show. I sat there looking around at my stuff. I had it all: a nice apartment, a brand new BMW, a hot girlfriend -- everything. But I'd gotten fat. I hadn't read a book in months. I hadn't done any personal development. So I started thinking, 'What happened to you, Jeff?'

That was a defining moment in my life. I reconnected emotionally with what's important: following your sense of purpose, making a difference, and connecting to other people. There's something about having money when you're not mature enough to handle it -- it can really take over your life. I'd turned into this jerk with no self-awareness, and I hated it.


Photo by Sara France

So said Jeff Riddle with a sheepish grin, shaking his sandy blond hair from side to side in disbelief. In his 30 years on this planet, Jeff has been an all-star baseball player, rock star, real estate magnate, spiritual seeker with a vow of celibacy, motivational speaker and, now, entrepreneur. With his daring approach to career and life choices, warm and enthusiastic persona, and fearlessness in taking on challenges, he personifies the Life Out Loud.

Jeff Riddle was born and raised in Burlingame, just south of San Francisco. He grew up playing baseball and the flute. "Half of the year, I was the popular jock. The other half of the year, as a member of the marching band, I was an outcast," he laughed. "My family taught me that life is about living every day to the fullest. So I grew up willing to take chances."

In college at UC San Diego, Jeff walked onto the baseball team. His outstanding performance on the field secured his position on the team. Then his mother passed away. Inspired by her death, Jeff committed to taking himself to the next level with his chosen sport. He worked out five hours and consumed 10,000 calories every day, and by the end of the summer had gained 30 pounds of muscle mass. While he returned to the baseball field an unheard of sophomore that fall, he quickly became a top prospect.

Tragically, Jeff suffered major injuries both his junior and senior years right before the draft. He knew the second one meant the end of his baseball career. "It was pretty rough going," he recalled. "For 20 years, being a pro ball player was my number one desire. But I lost it, two years in a row, right before achieving my dream."

That's when Jeff had a most atypical, but very Life Out Loud response to his situation. "I decided, to hell with it. If I can't be a ball player, then I'll be a rock star."

So Jeff teamed up with his buddies Jakob Martin and Ian MacManus, two talented young musicians, and started a group called The Storrow Band. Thanks to his years of flute playing as a kid, Jeff was able to pick up the guitar quickly. The band started touring college towns and took off.

Here's another point at which Jeff's path diverged from the norm, however. Rather than boozing it up and taking advantage of their female fans, Jeff, Jakob and Ian made two pledges:
1. No drinking for 24 hours prior to a show. (And they were playing six shows a week, so that meant not much drinking at all.)
2. They wouldn't be intimate with anyone unless she had a prior contextual relationship to the band. So, for example, they might connect with a friend of a friend, but not a groupie.

Jeff explained why. "We realized that most people and their fans are just enamored with the idea of celebrity. But we wanted to live with integrity. We genuinely cared about our fans as human beings. So we said, 'Hey, we're not going to take advantage of this."

After two years on the road, Jeff grew tired of the lifestyle. He left the band and went into real estate. Within months, he became a top producer in Northern California. By the age of 24, he was making tons of money. Then one Wednesday afternoon, he woke up. "On that day when I became so disgusted with myself, I sold everything I had. I quit the real estate business and committed to starting over."

As he developed his business ideas, Jeff took another remarkable step: He made a vow of celibacy. "I realized that, having lost my mom at 19, women had become my security net. I had to learn how to deal with the stuff going on in my head without any feminine energy to support me. It proved to be the hardest thing to deal with in my entire life, but it also changed my life in just six months. I became far more compassionate to others. I learned a great deal about myself. And everything just took off after that because my lens on the world had changed."

Jeff determined that his life purpose and innate skill set lay in figuring out how to connect with people in a meaningful way. He formed Riddle & Co., a sales company whose primary approach "the givegive" is about selling through deepening relationships.

Jeff explained, "Every business out there is selling something. As the world gets noisier, most companies are just getting louder and more aggressive, which is only turning people off. I believe we have to move beyond the transaction and focus on developing deeper, more authentic connections with customers. Everyone should get something meaningful out of the relationship."

I asked Jeff what it means to him to live the Life Out Loud. He replied, "It's about a relentless commitment to self-growth. A lot of people have looked at me in the past said, 'Wow, you were so successful in 'fill in the blank.' How could you quit?' But I'd stagnated. I'd become just another unfulfilled person. I was growing horizontally, not internally. So in each case, I left to do something bigger. Everyone can and should do that -- commit to figuring out their life purpose and going after it."

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