In the midst of the Covid lockdown, Bill Gurley at Benchmark Partners, reached out to me via direct message on Twitter after he saw some comments I made online.

I was flattered. Gurley is a legend. He has invested in Uber, Grubhub, Zillow, Nextdoor and many others. He could easily get any CEO he wants on the phone.

That Gurley would reach out to someone he didn’t know based on a slim hope he could learn something made more sense after I watched a speech he gave MBA students at his alma mater, the McCombs School of Business at the University of Texas.

Gurley told the class that one of the biggest predictors for success in life and business was relentlessly identifying and reaching out to people you could learn from.

Gurley illustrated his point with examples from the lives of musician Bob Dylan, basketball coach Bobby Knight and restaurateur Danny Meyer. All three went to extreme lengths to seek out mentors or people with deep experience in their fields.

Dylan hitchhiked 1,200 miles from Minneapolis to New York City with a guitar, a suitcase and $10 to meet his hero, Woody Guthrie. Bobby Knight identified the five best basketball coaches on the East Coast and tracked them all down. Danny Meyer made a list of the 12 top chefs and set about meeting them.

They all took extensive notes to incorporate lessons into their own work. In the case of Meyer, that meant creating a notebook for each chef and analyzing recipes and techniques that made them special.

“I can’t make you the smartest or the brightest, but it’s quite doable to be the most knowledgeable. It’s possible to gather more information than somebody else, especially today,” Gurley told the students. “Take every chance you can to find someone who can teach you.”

Gurley said he worked on his speech — called Runnin’ Down a Dream: How to Succeed and Thrive in a Career You Love — for more than a decade.

He gave the students five big pieces of life advice:

  1. Pick a career you are passionate about
  2. Be obsessive about learning about your field
  3. Develop mentors in your area
  4. Embrace peer relationships in your field
  5. Always be gracious and pay it forward

Finding mentors when you are just starting out can require substantial effort, as Gurley’s examples from Dylan, Knight and Meyer show.

Making that a lifelong habit requires a different mindset, one in which curiosity trumps the overwhelming social pressure to stay in your lane.

You can find Gurley’s video pinned to his Twitter feed or on YouTube:

Note: The photo is the iconic list of 33 New Year’s resolutions made by Dylan’s idol Woody Guthrie in 1943 that starts with Work More and Better and ends with Wake up and Fight.