Hunter S Thompson

Gonzo Strategy – Business Advice from the Sports Desk

A tribute to Hunter S. Thompson*

In a series of six blogs, I will draw some strategic planning advice from an unusual source: the Gonzo journalism of the late American author, Hunter S. Thompson. Enjoy!

The third.

Chance and synergy. Despite being a big believer in the necessity of structure and planning for a successful strategy, you must seize those random chances that come your way. In the case of Hunter S. Thompson, it was meeting Ralph Steadman. Steadman was a UK illustrator, whose savage caricature matched Thompson’s insightful yet off-beat writing style perfectly. He was first sent to join Hunter on the now infamous coverage of the Kentucky Derby horse race. Despite the shock of the initial meeting, it would become an alliance that would last decades and annoyingly stick in the throat of the establishment. It is highly doubtful if Hunter planned the next day let alone this alliance, but his keen mind knew what would work.

Very few organisations—except maybe some in the creative arts with deep pockets—can freewheel like this. For most of us, the risks outweigh the rewards. So how do you not let such opportunities fly by? Well, there is a pretty basic business theory that can assist you. Form a separate entity. The main part of the organisation continues business as usual, while the new arm takes on the business of the future. Unlike Thompson and Steadman, they do have to be constrained to reality a little – no point in coming up with bold yet unachievable aspirations.

Maybe Hunter S. did understand it: ‘When the going gets weird, the weird turn pro’.

Jason Thomas is the Founder of de Montaigne Strategic Planning, which provides robust strategic planning and training services to small to medium-sized enterprises, not-for-profit organisations and government departments.

He has over 30 years’ experience in senior leadership, operational and planning roles across the military, public and private sectors. In addition, Jason holds numerous degrees and qualifications including Gold Mastery Certification with the Haines Centre for Strategic Management.

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Gonzo Strategy – Business Advice from the Sports Desk – Post 1
Gonzo Strategy – Business Advice from the Sports Desk – Post 2