Father to Son: It’s Time to Make a Change

On this Father’s Day, I remember one of the last serious conversations I had with my father before I lost him to brain cancer, glioblastoma to be precise. The cancer is an aggressive, certain death sentence for the patient and an extended symposium on mortality for family and friends. I was in the fourth year of my fourth startup, an extremely successful cybersecurity company. I would often call my father on my drive into the office — he previously underwent surgery to remove the tumors and had a remarkable final year — and we would talk about life during the Bay Area’s enduing morning windshield season.

This conversation was different.

Right after my father’s operation, he asked me: “how is your job?” “You know,” I responded, “another startup, an amazing opportunity, but, as always, a lot of putting another brick in the wall.” He responded with the penetrating insight that must come to people running out life’s clock. “It seems like you have done this for a long time,” he began, “and you’ve done pretty well. Why are you still doing it?” Since candor was the theme of the day, I told him I was not 100% sure. He concluded: “then why do it, why kill yourself doing the same thing, again”?

It was a lot of think about. Eventually, I realized: he’s dying, and, on the bridge to eternity, he just mortally wounded my career, too.

“IN MY END IS MY BEGINNING” — T.S. Elliot, “East Coker, The Four Quartets”

In the earliest part of my career, I worked at two great tech companies at their peaks. I built eCommerce products for IBM in the 90s and had two successful runs as an executive at Cisco, including the acquisition of my company Airespace, an enterprise Wi-Fi company that took off in the mid-2000s. After Cisco, I was part of the executive team at Nicira, a revolutionary networking software company that was purchased by VMware, and then helped Illumio, a cybersecurity unicorn. I had a great run as an enterprise technology entrepreneur.

If I was really honest with myself, though, I was a little tired of the game. Enterprise tech is a never-ending march of “better, faster, cheaper” alternatives to legacy technologies: the cloud is replacing the data center, SaaS is replacing packaged software, smartphones are replacing personal computers, etc. My stuff is better than yours.

How Will You Measure Your Life?

It’s always good to look for guideposts or bridges to cross during career transitions. Contemplating my father’s mortality, I spoke with friends and mentors. I also read three books which had a huge impact on my thinking about the future:

  • How Will You Measure Your Life, Clayton Christensen. Understanding how you “tick” and building a career plan on what makes you happy;
  • Being Mortal, Atul Gawande. What happens to your body when you are dying and how to maintain and a dignified approach to your death;
  • Don’t Even Think About It, George Marshall. Why people’s brains are wired to ignore climate change.

It is also important to understand how you “show-up” when going through a big career change. One afternoon after we finished the quarter, my business partner and boss said: “you are not the same guy from 4 years ago, you are not into it the same way.” I responded, “you’re absolutely right, I’m not.” We worked out a smooth transition plan.

FINDING THE NEXT MISSION: ATOMS AND BITS

In the latter part of your career, many decisions are often tied to some view of long-term financial stability. Money aside, you really need to understand what will bring you satisfaction.

The trajectory of the planet and our society was weighing heavily on me, much more than material rewards or career accolades. If we leave our children a nice inheritance and a climate-ravaged, fractious planet, what do we really accomplish?

After leaving operating roles in enterprise technology, I became involved with companies that deal with some of society’s largest challenges. I became an advisor at Pivot Bio, a microbial answer to chemical fertilizer that has the potential to turn back the climate clock; I became a board member at Evolv Technologies, the best answer to removing the risk of mass shootings at a range of venues without turning them into prisons.

What I realized that after spending decades using atoms (building networks) to create and move around bits, I could now meet my personal goals of a better legacy by using bits to build better atoms (food, health care, physical security). And after 25 years as a builder, I could become an investor and joined the leading deep tech venture firm.

GETTING TO THE NEXT BRIDGE

Along the journey, I learned three things during the journey to a second career:

  1. Define your higher ground. I found my center around deep tech, attacking inefficient supply chains, reducing greenhouse gases, improving physical security, and combatting cancer much earlier. My higher ground would be leaving a better legacy for my children.
  2. Find your new tribe. After working in an industry for a long time, you build strong networks, strong friendships. To do something new, you have to leverage those networks and create new ones. You may need a new tribe. Mine is Data Collective
  3. Look for compelling economics, not just social causes. Who knew the cloud and AI would allow you to reinvent existing industries and supply chains — not just their information systems — to make the world cleaner, greener, safer, and more economically fairer to more people?

I think of my father every day. I never, though, expected his passing as a passport to my second act.