In October, the company I co-founded pitched on the main stage as a top 20 finalist at TechCrunch Disrupt, drawn from thousands of applicants. I was not in the audience or in the wings, because four days earlier the Navy had sent me mobilization orders. While Matt Chase, our senior vice president of global sales, delivered the most important pitch in our company’s history, I was in Norfolk, Virginia preparing to deploy. The mobilization was eventually canceled before I deployed, but, by that time, Matt was already being mic’ed up to get onstage.
I have thought about that week every day since, and I have come to believe the orders were the most honest test a CEO can face: proof, on a date I did not choose, of whether I had built a durable company or a team that could not function without me. The startup world quietly treats reserve service as a liability, but my experience that week convinced me the industry has it backwards.
There’s not much I can say about the mobilization itself, so this is a story about what the orders demanded of the company rather than where they were sending me.
Orders arrive via phone call with a report date and no room to negotiate. Questions a leader would normally settle over several quarters had to be settled in days. Investor relationships I had managed personally moved to Jonathan Sperber, my cofounder and our chief strategy officer. Decisions that existed only in my head had to be written down and handed to people I trust to make them without me. The handoff that nearly broke was signature authority on our accounts, which existed in exactly one name until that week.
Matt took over the pitch I had expected to give and tried to make the script his own. He delivered it well: the sales and investor conversations the pitch opened are still running today. The biggest moment in our history ended up in the hands of our head of sales rather than one of my co-founders. None of it resembled the continuity plan that sits untouched on our Google drive, because it happened on a clock, with Disrupt approaching and the real possibility that I would be unreachable for six months.
Every CEO assures investors that the company would survive without them, but almost none of us are required to prove it. The succession conversation is the one that slides to next quarter because the founder is healthy and nothing forces the issue, and mobilization orders are the rare event that forces it on a schedule the founder does not set. The test showed me precisely which parts of the company had real owners and which parts had been held together by my personal attention, and that knowledge has outlasted the orders themselves.
Every founder eventually gets pulled away, whether by a health crisis, a family emergency or another distraction. And usually with less warning than the Navy gave me. A reservist is simply a founder who receives the test in writing and is obligated to prepare for it in advance.
My civilian work involves identifying foreign influence campaigns as they move through American online conversation, so I have never thought of military service and company building as entirely separate worlds. The numbers say people who hold both roles are becoming rare.
Fewer than 1% of Americans serve in uniform today, across the more than 1.2 million on active duty and the roughly 800,000 of us in the reserve components. The veteran share of new entrepreneurs fell from 12.3% in 1996 to about 6% by 2011. Research from the Federal Reserve Bank of New York has found that veteran-owned businesses have a harder time accessing capital than comparable companies. In my own fundraising conversations my reserve commitment has come up, politely and more than once, as a key-person risk. We announced a $7 million seed round in October, and we are not raising now.
I understand the instinct, since the investors asking are stewards of other people’s money, but I believe they are mispricing what they see. A founder who maintains a reserve commitment practices the one discipline most companies pay consultants to simulate, which is the readiness to hand the operation to someone else on short notice.
There is an obvious objection here, and it deserves a straight answer: a chief executive who can be ordered away at any time is a genuine operational risk, and no board should pretend otherwise. My own orders proved as much, because the company absorbed real disruption in those weeks. But the risk of losing a CEO exists at every company in some form.
The reservist is the only leader required to prepare for it before it arrives, and that preparation is the difference between a disruption and a collapse. The cancellation, when it came, was a change in the Navy’s needs that I controlled no more than I had controlled the original orders. It changed nothing about the test, because by the time word came, the handover was complete and the company had already stood on that stage without me.
The company came out of October stronger than it went in, because the delegation we built under pressure has stayed in place. Other founders should run this drill before circumstances run it for them, starting with hiring leaders whose judgment they trust. Investors can help by changing what they read into a founder’s service record.
Veterans Day is approaching, and the tributes it brings are welcome, but the more useful form of gratitude would be to treat reserve service as evidence of operational discipline rather than a liability to be priced in.
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