One of the best CEOs I know is a Former Military Officer

Ben Horowitz of A16Z popularized the term “wartime CEO” and drew the analogy of leading a fast-growth company to the challenges of war. Many of my friends (and some of my extended family members) are active or retired members of the military. In business school, I even signed up for a weekend course at the Marine Corps Base Quantico to “play” Marine for a day and learn how the military first breaks down and then builds its leaders.

I have always felt that the Military is one of the best leadership schools in the world. As this HBR article from 2009 points out:

military leaders tend to hold high levels of responsibility and authority at low levels of our organizations… military leadership is based on a concept of duty, service, and self-sacrifice…We view our obligations to followers as a moral responsibility, defining leadership as placing follower needs before those of the leader, and we teach this value priority to junior leaders… Soldiers in [extreme crisis conditions] must be led in ways that inspire, rather than require, trust and confidence.

And so it comes as no surprise that one of the CEOs I respect the most is a former Army officer. Tommy Sowers is a veteran, amongst many other things. I’ll let his Wikipedia page list them all out. He is now the CEO of a PropertyTech startup, GoldenKey. As he has transitioned from military (to academia and government) to the startup world, I have seen him apply many of the same principles as he learnt and applied while deployed in Bosnia and Iraq. Success of his startup is a mission, and one he is determined to win. He truly believes this, and passionately shares it with whomever will listen:

Fundraising is a tactical operation. Building the supply and demand side of his marketplace is being executed with military precision (and with the support of a team of veterans). But what I enjoy the most are his regular updates to investors and advisors, and I wanted to share them for other to learn from him.

He calls the SITREPs (Army speak for “Situation Report”) and it reads like a military briefing: Short, crisp, right level of detail and immediately actionable. I won’t share his KPIs but below is what the bi-weekly emails contain:

Team,
Summary: Stratplan, [XXX] and rebrand complete
Last period:
KPIs: [5 KPIs tracked regularly. Same KPIs each time]
[Three bullets on updates. None more than 3 sentences long]
This period:
[Three bullets with upcoming major milestones from strategy to tactics (such as new office space or key new hire)]
The ask:
[He always ends with an ask. An intro, an advice on website or branding, a request for investors to hurry up and sign the pending legal documents. One short, crisp, actionable ask]
Onwards,
Tommy

I have known Tommy for 20 years. He always got what he wanted through hard work (and sometimes “social hacks”). He’s achieved things that someone at his age should not have. And he is applying the same work ethic, smarts and sense of purpose to his startup.

This post is not meant to “blow sunshine up his a**” (an expression Tommy, the good ol’ boy from Rolla, Missour’a taught me…). It’s meant to hold Tommy as an example of a great entrepreneurial founder, of a great wartime CEO and of a role model for other founders…even if that simply means just borrowing his SITREP template.

I have watched him succeed many times in the past and know he will succeed in this venture as well.

Onwards!

Disclosure: I am not an investor in GoldenKey. My friendship with Tommy meant too much to put it at risk for any potential financial gain. I am an informal advisor and have received no options or shares. I do what any friend would do. I share what I know the VC-founder relationship and about how to best get the best deal.

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