Our Loss When Founders Sunset

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Sundown, yellow moon, I replay the past
I know every scene by heart, they all went by so fast

Bob Dylan

Our world has a natural ebb and flow to it. The tides come in and retreat, rhythmically, predictably. The seasons come and they go, moving us with them as change comes to everything we know. Our moon waxes and wanes in its celestial orbit, marking those same seasons with the strength of its presence. The sun rises and sets, marking minutes, hours, and days, in its infinite march toward new horizons.

Our lives mirror those changes as we begin, progress, and transition. From our first faltering steps through the last ones, we move through the tides, the seasons, the waxings and the wanings, the sunrises and the sunsets. My time at a recent trade show reminded me of this acutely when I ran across a founder in our industry who had recently sold his company.

After nearly twenty years of building a massively successful business, he sold to one of the private equity investment groups now consolidating high value companies in our space. Though we had never actually done business, his greeting was warm, familiar. I suppose that’s one of the benefits of standing beyond the day-to-day struggle of competing, posturing, and maneuvering. In our first encounter, we exchanged pleasantries, talked a bit about the trade show, and shared a story or two about the comings and goings in the general marketplace.

Later that day, I ran across him again. This time, the slightly guarded mask came off and he proceeded to give me a very entertaining collection of stories about various characters and companies in our industry. I learned of backroom deals, irate competitors, funny encounters, opinions on various players and their positioning, as well as sincere perspectives on the direction of the industry, its challenges, and its opportunities. Mostly, i encountered a veteran warrior who had traded his weapons and armor for something else, now looking toward a new season with hope and trepidation.

Considering my encounters with him over those two days, I was reminded of other recent conversations and transitions. Our industry is seeing major consolidation now that it has matured, demonstrating significant value for employers and employees, and now investors. I’ve had the chance to speak with numerous founders who have sold over the last 12 months. Powerful people who have spent 10-15 years building high value businesses and then exited. That’s the dream, right? With millions in hand, they can now do whatever they want.


The stories are always told wistfully. The memories, even the tough ones, are held with special reverence and, perhaps, a newly found lightness. The struggles blend into a different of tapestry, now fully justified at the end of the race. And the sadness, the loss of something, sits right alongside all of the gratitude for a journey completed. There is a hesitation and a relief to beat the blunted weapons and dented armor into plowshares for new purposes.

I’m struck by what is lost as these founders fade into the sunset. The amazing stories. The brilliant strategies. The dumb luck. The funny encounters, The quirky perspectives. The arrogance or the humility. The boldness. The insights and wisdom. The dogged perseverance over extended periods, through repeated setbacks, chasing dreams that were so very unlikely, while living constantly, and simultaneously, with the fear of failure and the hope of victory. I shake my head at all the memories of things that will be lost so very quickly.

Progress demands the waxings and the wanings, the ebbs and the flows. Life requires us to move through the seasons, struggling one day, thriving the next, and then beginning again. Our industry will move on, new players will emerge, others will exit, and new stories will be told. However, there is only one beginning. There is only one start to any undertaking and those moments are unique, special, and momentous. Those who build such things are also unique, special, and larger-than-life in their own ways.

Today, I pause for a moment to recognize and appreciate the changing of the guard. No, it’s not unique to the industry I live within, but few of us get to experience the creation and transition of a new universe. Rarely do we get inside glimpses into the forming of new planets and stars, the implosions of galaxies, and the supernovas that sometimes happen when all of the above line up perfectly. The evolutionary process of a company and industry is complex, erratic, uncertain, explosive, uncontrollable, and ultimately, beautiful for those who can appreciate such things.

Looking closely, we might appreciate the brilliance, and wonderfully imperfect natures, of the people driving these new universes as we see glimpses of ourselves in their struggles and victories. Yes, we lose much when our founders sunset.

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