From Above




Updated: Mar 3

Underpromise and Overdeliver. It’s a core tenet of the way I do business, a lesson handed down from my dad, and a fundamental part of my personal DNA. I don’t like to disappoint people, so I’m careful about only making promises I am confident I can keep.

The flipside of this, of course, is that you’re less likely to stretch. A lot of cool things happen in the world because of cowboys and BS artists – not because they deliver on their promises, but because they dare to promise things they don’t know they can deliver. They will inspire but also disappoint, take big leaps and suffer crushing falls.

As a tour guide, I’m not much of a cowboy.

We just enjoyed a wonderful week on the Otter Trail, a highlight of which is the Bloukrans River Crossing. At high tide, it can be treacherous and dangerous, and it is often the most anticipated and talked of event of the trip. Waves beat at you as you try to swim across a strong current with your bag hopefully not getting soaked in a dry bag. It’s quite something. At high tide. For us, it was low tide at 11 am, and with the full moon, spring lows at that. The crossing was a non-event, as we all walked through on mostly ankle-length water height.

My job, the whole week, was to moderate expectations. There is something disappointing in the lack of drama, given all the wild tales that are told of misadventures by other hikers on the crossing. But for us, my message was consistent: We don’t need to go looking for adventure. Let’s get up early, get there at the right time, and make things easy for ourselves.

For tour guides and business leaders, and parents even, I think the biggest challenge is to moderate expectations. Day by day, your charges will formulate a vision of to-be based on the various inputs they receive. And our job is to temper that messaging to what is possible and probable. And if improbable, communicate what would need to be done to make it happen. Get up at midnight. Train like a demon. Do the work.

I dislocated my shoulder when I was 19 (a few times) and my appetite for big leaps was diminished by the consequences of that first silly cliff jump. In the business world, I built my business slowly and methodically – using my own resources, and taking careful and measured risks as I built it. I follow the same approach when leading people on tour.

Cowboys start businesses with other people’s money. They promise to build technology, systems, or products that aren’t feasible, that no one wants (yet) and that require all-nighters, crazy committed teams, and incredible vision. We’ll all have an inferiority complex if we compared ourselves with Elon Musk, but there are versions of him out there that have done the same thing to various lesser degrees of success.

Those people often fail. And other people’s money goes bye-bye. They shake off the investor anger, restructure their finances, and walk away to go disappoint someone else. Until they don’t. And then the results are spectacular.

In the South African business context, Koos Bekker is a personal hero of mine. I mean, as a Naspers investor, you have to give him credit where credit is due. He built something incredible, admittedly through one particularly good swing of the bat (Tencent). But there were also numerous (horrible investor cash sucking) failures, most notably Mweb.

But I suppose you have to pick a lane. Either be a cowboy and be comfortable with the risks associated. Fail big. Dust off. Keep on going. Take on the high tide river crossing.

Or don’t. Take measured risks, bootstrap your business, don’t fly to Icarus levels but know that you value long-term relationships more than short-term glory. Get your team up early to take the easier road, and know that you might have missed something by not choosing adventure.

It’s like Stephen Covey’s Circle of Concern/Circle of Influence. A long time ago, I decided to work within my Circle of Influence, and my life has been incredibly rich for it. I know a lot of guys that have, at least on the face of it, achieved more by stretching out to the Circle of Concern. But I don’t think they sleep as well at night. This year, for my birthday, I’m going to give myself a few sleepless nights. We are putting together a trip to the Amatola Trail in Hogsback in September. It’s tough. Long. Brutal. But it will be worth it.

Get in touch if you want me to come talk to you about joining us.


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