Before the jester's cap, the multi-baggers, and the series of investing books ... there were:

Two middle school boys.

These two -- after being tucked in to bed by their parents -- would quietly bust out a radio. If the weather was clear, they would catch the broadcast of the Minnesota Twins game from a station 1,000 miles from their Washington, D.C., home.

Believe it or not, this scene -- played out successfully over countless summer nights in D.C. -- represents the beginning of The Motley Fool.

A series with our chief rule breaker
Recently, I sat down with David Gardner, co-founder of The Motley Fool, to discuss his background and his investing philosophy. Whether he's the kooky-looking guy on CNBC wearing his jester's cap or the lead advisor of the newsletter you subscribe to -- David Gardner is one of the most respected names in investing.

And while he freely volunteers biographical information about himself, it's been awhile since we've taken a comprehensive look at one of our founding Fools. Over the coming weeks, I'll be publishing the content of our discussions.

Half of these articles -- the biographical ones -- will be published for all to view on this site. The other half -- dealing with his investing philosophy -- will be available to our paying members of Stock Advisor and Rule Breakers. But because we offer 30-day trials to these services, anyone can access this information for free.

Ever higher
Before diving in, though, I want to comment on the title. Here at Fool HQ, every employee has his or her own motley value. David's is "excelsior," which in Latin means "ever higher." As you will see, the unending push to strive higher is at the center of David's universe. It is the thread that connects the dots in his life.

But before he could ever dare to push higher, he needed the confidence to do so. Understanding where he got that confidence brings us back to the Minnesota Twins.

An enchanting experience
At first blush, it seems odd that the brothers listened to Twins games. Baseball aficionados, however, know that before they were the Twins, the team was known as the Washington (D.C.) Senators.

Back in the '50s, David and Tom's grandfather had purchased a minority stake in the Senators. Though the team moved to Minnesota, the family retained their stake. This created lifelong fans out of the Gardner brothers.

When he was 15, David fulfilled every young fan's dream: He served as batboy for the Twins. "With a nucleus of young players not much older than myself at the time, I found it easy to relate to the players in the clubhouse." David learned a lot from seeing how professionals like Kent Hrbek and Frank Viola conducted themselves. But it was the confidence he gained from feeling accepted by the team that left a lasting impression on David.

"It was from this experience that I became hooked," he says.

Learning at a young age that the sky's the limit is powerful; it gave David the right to dream big.

High school days
"No year," David says, "was more important in my life than my 18th." A senior in high school with a laundry list of accomplishments (e.g., class president, starter on the football team), David actually had his sights set on Yale -- with the possibility of a career in drama.

But then, with the arrival of a package indicating that he was a finalist for the prestigious Morehead-Cain scholarship, plans changed. The scholarship is a highly competitive nationwide offering, modeled after the Rhodes scholarship. Those who receive the distinction are rewarded with four years of tuition, room, and board at the University of North Carolina at no cost.

When all was said and done, David was crowned a Morehead-Cain scholar. "It made me feel special, singled out, and accepted." Once again, David was rewarded for reaching ever higher, further fueling the passion inside of him. That passion, though, would soon be tested.

Humbling Tar Heel days
We could excuse David for thinking he was hot stuff entering college.

He would soon find out this wasn't the case. "I didn't realize at the time that I was just a big fish in a small pond before UNC. As soon as I got to college, things changed. The pond was much bigger, and I ... was much smaller."

First, he met Glenn Etter. "He beat me in everything: physical contests, intellectual contests, board games. You name it, he beat me in it. It was very humbling." But Glenn would be only the first of many formidable classmates.

Confronting these humbling experiences, David had two choices. "Essentially, I could keep trying to beat them, or I could join them and learn from them." In the end, David says he just got sick of losing and decided to ask his friends for the tricks to their success.

This willingness to swallow his pride and ask for help on his quest to reach ever higher was crucial to David's future success.

This played out one day while playing friend Jim Surowiecki in a dice baseball game called Pursue the Pennant. Incidentally, Surowiecki is now a staff writer at The New Yorker, and author of the critically acclaimed The Wisdom of Crowds.

While playing the game, David got smacked around once again. "Jim beat me eight games in a row. Finally, I threw my hands up and just asked him what his secret was."

Jim's answer to that question guided David to a baseball guru that would eventually shape how David thinks about investing. This shift in thinking is -- in large part -- responsible for David's remarkable run in the stock market, beating the S&P 500 by an average of 11.2% per year over the past 17 years as of June 30.

Next in this series will be a look at the biography of The Motley Fool as a company, including the trying times surrounding the dot-com bubble, and where the company stands in today's investment community.

For those who want to dive deeper and find out who this then-obscure guru was and what David learned from him, I encourage you to sign up for a free trial of Stock Advisor or Rule Breakers -- David's two services -- today.

Want to see how David repaid his Morehead-Cain friends? Check out this speech by him in 2009, and then look at the results of the advice he gave his audience.