Recently I had lunch with Chris Michel, an entrepreneur, investor and Silicon Valley’s one true renaissance man, at one of his favorite San Francisco restaurants, the Cavalier. The food is British-inspired. The conversation, however, was inspired by a friendship that spans over a decade. I was introduced to him by Abigail Johnson, one of the finest people in the “communications” business. She is a connector who eschews attention, and she is the polar opposite of today’s fly-by-night public relations carpetbaggers. “You and Chris will love each other,” she said.

She was right. Chris founded Military.com and had a lot of stories to share when I started Gigaom. We got to know each other better a few years later through my ex-Forbes colleague Carleen Hawn. She was editing one of my new ideas at that time, WriteRead, a founder community that was a mishmash of Medium, Quora and Hacker News. It was about giving founders a place to share their wisdom. Like a lot of things we did, it was too early and the software wasn’t really there. But the outcome of that effort was a deeper friendship with Chris. For me, that is a win.

Chris has become a close friend and a constant source of encouragement when it comes to my amateurish attempts at photography. He is an amazing photographer. His landscapes are sublime, but his portraits are what make him exceptional: He looks into the soul of a person and somehow captures it on film. He does this all the time. “You give us the gift of time, Chris,” I told him. “I hope you realize that.” With his photos of people in Silicon Valley, he is writing a beautiful story and giving us back these special moments to re-live.

At lunch we talked about my trip to Iceland. We talked about the role of a board member. We talked about Chris Anderson and his drone company, 3D Robotics, where Chris is a board member along with my True Ventures partner Jon Callaghan. We talked about the deep and continued sense of mourning I am experiencing for Gigaom. In the end, we talked about Silicon Valley, the idea of success and the cult of “winning.” We talked about winning in terms of money. We talked about a (faux) sense of winning or losing we get when startups “exit.”

And then he asked me, “What is winning to you?” Hard question, but without thinking too much, I pointed out that if I can have a day that starts with more questions than answers, is spent doing things I love and I go to sleep early, tired, smiling and thinking of new questions — that to me is #winning. And if I can have one in five days like that, it amounts to a winning life. In his own sweet way, Chris was doing what I have tried to do in my writing: holding up a mirror so I see myself better and move forward.

P.S.: What is your definition of winning? Let me know on Twitter or Facebook, or email me.

June 2, 2015, San Francisco

Photo of Chris Michel by Chris Michel, courtesy of Chris Michel