While Ken Friedman (MBA 1983) was at HBS, he and a group of about a dozen friends would get together regularly to play cards. The group vowed to continue to do so after graduation, and would hold annual weekend get-togethers to catch up. It became a brotherhood, Friedman says. But almost fifteen years ago, one of the members of that group was diagnosed with cancer, ultimately passing away after a 15-month battle.

It was a wakeup call for Friedman. He’d had a successful career in investment banking and venture capital, which included being the founder and former president of the investment banking operation of Houlihan Lokey at the age of 28. Houlihan Lokey would go on to become a New York Stock Exchange public company.  

But his friend’s death made the next big VC deal or M&A transaction seem much less important. Instead, Friedman reoriented his  life, focusing more on philanthropy—and also getting back into one of his favorite childhood pursuits: motorcycle riding. Ultimately, this renewed passion for riding would become an historic mission to ride a motorcycle on all seven continents.

 Friedman completed his mission in December of 2019, and in this episode of Skydeck, he and I talk about the challenges he faced during his epic journey—and why he believes that getting out of one’s comfort zone and tenacity are the keys to personal growth.