What Teaching Taught Me: Lessons From 22 Years At Stanford GSB

Earlier this spring, I was honored with the Stanford Graduate Business School’s 2024 MBA Distinguished Teaching Award. The message below is adapted from the message I shared at the award ceremony, which you can watch in its entirety here.

In 2002, Stanford professor Irv Grousbeck and researcher Janet Feldstein wrote a case study about me. Now that I teach at the Graduate Business School myself, I know that each quarter-long course typically includes one “failure case.” And I think, back then, that was likely my role in their curriculum. 

I’d started my company a few years earlier in my dorm room as a student at the GSB — and by the time Irv and Janet wrote their case, absolutely everything was going wrong. I had made management mistakes. I’d hired the wrong leaders. I’d lost money on many of my investments. Often, the subject of a failure case is looking back on their mistakes and stumbles decades later, with plenty of successes since. But me? I was 29, so my career was mostly just my failures.

Supporting Life’s Journey

When I taught the case to students myself for the first time, I bombed. That’s not false humility — it was crickets. But after class, I went to lunch with the students and realized all the details of company-building that I’d tried to share weren’t really what interested them. They wanted to hear what it was like to live through the worst-case scenario: failure. (The answer: Not as bad as I’d thought.) And they wanted to understand how I’d overcome my fear of failure to start a company in the first place — and to keep going when things looked dire.

“I bombed. That’s not false humility - it was crickets.”

From then on, overcoming one’s fear of failure became a cornerstone of my teaching.  

When I teach Managing Growing Enterprises today, we dig into the specifics of hiring and firing, fundraising, and having difficult conversations. But I’ve found that students are most hungry for support on the journey of life — and fortunately, that’s an area where I have a lot of energy to give. Helping them grow as people, in and out of the classroom, keeps me going as an instructor.

Tony Robbins, the godfather of executive coaching, says that while people hire him to teach them success, they actually need fulfillment. I see my work as a teacher the same way. Students sign up for my class to learn the specific skills to become a leader and build a company, but my real purpose is to help students figure out who they are; what their dreams really are, deep down; and what fears, doubts, and limiting beliefs are getting in their way. Then, we work together to overcome those challenges and chart a path to help them live the lives they want to live. 

Standing on the Shoulders of Giants 

Isaac Newton once wrote, “If I have seen further, it is by standing on the shoulders of giants,” and I have stood on some absolute giants’ shoulders at Stanford. 

Along with Irv and Janet, Dick Allen, Joel Peterson, Kevin Taweel, Jim Ellis, and Peter Kelly have all invited me to share my story as a case guest — years before the success part of it had been written.

David Dodson did, too, and I also had the pleasure of co-teaching with him for several years. I will never forget the first time we met to discuss that partnership. When I greeted him, I said something about being excited to give back to the students. His response was the first of many lessons I’d learn from him: First and foremost, the opportunity to teach isn’t a gift you give — it’s a gift you receive.

Irv Groesbeck didn’t just co-write the first case on me; he taught me to be a teacher. And for me (and hundreds of others), he has been the voice saying, “You can.”

“For me (and hundreds of others), he has been the voice saying, ‘You can.’”

The Gift of Teaching

Of course, my fellow teachers aren’t the only ones who made my career at Stanford possible. The day I told my partners at Alpine that I’d been invited to become a lecturer, I warned them it would be a distraction, but they supported me without hesitating for even a moment. Every year, when I’m commuting to campus 20 times in a quarter and spending hours with my students, they pick up the slack. I could never do it without them. 

Meanwhile, my family has patiently put up with the many nights and weekends of work that come with my having two jobs. They’ve also been the guinea pigs for every exercise I put my students through — they know all about dreams, “Genie goals,” and limiting beliefs. I am incredibly grateful for their love and support.

Most of all, it’s my students who have made being a teacher so rewarding — and who make the Distinguished Teaching Award perhaps the most meaningful honor I’ve ever received. They throw themselves into our work together with so much energy and vulnerability. They put themselves out there. It is abundantly clear to me how much they want to make a difference in this world. 

“It is abundantly clear to me how much my students want to make a difference in this world.”

To play a small part in that journey is a privilege, and it means more to me than I can ever fully express. What I can say is that David was absolutely right: Teaching is a gift, and I am eternally grateful to be a recipient.