The Myth of Smooth Success

When most people see entrepreneurs succeeding, they often think or remark something along the lines of, “Wow, that guy [or girl] really has it figured out. They just keep rising.” 

While it may be true that the entrepreneur is doing a great job and operating at an advanced mental level, the mistake often made is that their rise has been smooth, either professionally or personally. Everybody knows that founders work incredibly hard, but so many are fooled that hard work and clever decision on their own are enough to succeed, over and over again.

In my limited experience, I’ve found that there’s a little more to this game than just smarts and laboriousness. After all, people need that to succeed at just about anything in life. In startup entrepreneurship however, there are a lot more unknown and difficult variables to contend with. These could include issues like market timing, tricky investor relations, co-founder politics, or managing a difficult cash runway. It may sound straightforward, but dealing with any of the above when pushed to extremes can feel like a life threatening situation, and raise a person’s stress levels to dizzying heights.

As such, “success” tends to show up when the founder has learned to continuously weather these variables and survive- while working hard and cleverly of course- until good things happen. That’s what people often refer to as “getting lucky”. Even founders, when speaking of their successes will make statements like, “I got lucky there”, or “That deal came out of nowhere”. Was it luck? Well, yes, to an extent. But in my view, if you stay in the game long enough you’re bound to get lucky at some point. That’s really what it’s all about- being tenacious enough to survive the difficult scenarios; again and again and again.

On the surface and to the outside world though, everything can seem hunky dory. Founders tend to hide their struggles, internalizing them and not wearing their hardships on their sleeves. When viewed in perspective, victories are unimaginably hard won at times, yet this is unseen by most. And therein lies the myth of smooth success.

Why International Flights Are Good for Mental Health


In recent months, I’ve been taking more and more trips between Cape Town and San Francisco. Now, this a long flight. It generally consists of two legs, one to the Middle East or Europe then the second to the USA. Total time in the air: around 24 hours.

When it hasn’t been done in a while, long distance travel is exciting, but it quickly becomes a chore. Crossing 12 time zones, sleeping in airports and sitting on planes forever certainly exact a wicked toll on the body. Lately however, I’ve grown to appreciate what all that lonely time in the air does for my mind.

Let me explain. If you’re reading this blog, you are probably a technophile who spends a ridiculous amount of time in front of their laptop and generally enjoys working more than the average person (just like me). In my case, I fell that The problem with this behaviour is that I rarely give myself the chance to unplug- I thrive on being hyper connected all the time- so constant email, task management, Twitter and RSS are what I thrive on. Even if you can live like this without experiencing fatigue or productivity losses, I find that a key element of mental balance can easily be crowded out and forgotten: introspection.

Introspection occurs when we spend long periods alone, and delve into our mind to remember what’s important to us, what kind of people we want to be, and ask ourselves how things are going. It’s a surprisingly elusive state if you have constant access to Wifi or an iPhone with 3G in your hand. I love it. It’s a form of meditation. A session of proper introspection leaves me feeling more centered, relaxed, motivated and in control. It is highly recommended.

Of course, I could do this at home (or in a hotel) once in a while, and I should. But somehow, I always manage to get busy and stay that way. I’ll work on improving. For now though, I’ll keep appreciating the silver linings of these long distance travel clouds. And why doesn’t this apply to domestic travel, you may ask? Because one can usually get onboard Wifi on local flights of course!

—This post written 11,500m somewhere above the Atlantic. Image credit: Shutterstock.

5 Lessons from Billionaires - Based on Real Life Interactions

My good friend Roger Norton recently wrote a thought provoking blog post describing some of the lessons he had learned from billionaires.
During years of working in the super yacht industry, Roger spent a large amount of one on one time with his various bosses (the yacht owners), all of whom were members of the richest club on Earth. I remember hearing a lot of inspiring, interesting, and sometimes downright wacky stories from him on this topic. 

In his post he shares some of the conclusions he made about the mega-wealthy, based on his observations. These include:
1. You can become a billionaire in any area. The professional range and disciplines of Roger’s bosses varied wildly, from financial traders to fishing tycoons.

2. Anyone can be a billionaire. The social circumstances from which the individuals came from mattered far less than their willingness to pursue to their ambitions. 3. It take a certain type of person. A certain mindset or way of thinking was common among them, exemplified by tenacity and critical thinking.

4. Having loads of money doesn’t change you, it just lets you be more you. Money is simply the ultimate enabler.
5. All rich people have enemies. I’m not convinced that this applies to everyone, but Roger did notice a certain paranoia among several of his bosses.

For more detail, I suggest reading Roger’s original post