A few weeks ago I was VERY fortunate to visit Silicon Valley to pitch Empty Trips at the Startup World Cup in San Francisco (trying to do my team justice). The winning pitch would earn a million-dollar investment. But let me back up a bit …

What is DAS?

I call it “Dark Ambition Syndrome” or DAS: an anxious state of mind that never allows you to be satisfied with where you are, recognize what you have achieved, be truly present, let go of insecurities, or simply stop and smell the beautiful roses. Maybe I’ll write a book on it one day; in front of a fireplace in the Canadian Rockies, wearing sheepskin slippers whilst sipping on red wine, delving into retrospect (#goals). See – I did it again.

Whether you are considering a career move, a business pivot, a change of city, a relationship break-up, or simply choosing a new car, you’re facing infliction points of whether to stay where you are, or jump to the other side of the fence… The other side: where the grass looks greener, and the roses more red. But is it? Before you make any catapulting leaps, check you are not falling victim to DAS.

Firstly, life is exciting and ever-changing. It will bring different options to your side of the fence over the years and through the seasons… Life never stagnates – remember that, regardless of your situation!

I’m sure at times you may find yourself proud of your home-grown turf, especially in summer when it’s green, lush, well-manicured and you’ve selected just the right amount of fertilizer.

However, in winter we feel our grass is dull; we get depressed, restless or unconvinced to reinvest in more fertilizer. Even if it’s only one small patch in our garden that has not stayed green, we tend to focus on that one brown patch, and ignore all the green grass or roses around it…

It’s during these winter times that we look to the other side of the fence, and we explore other options. “Maybe a different type of grass would stay green forever? Maybe it was the fertilizer, should I water more, work more?”

Unfortunately, winter brews irrational decisions, focus is lost and we no longer like the kind of “Gulf Green” grass below our feet. We convince ourselves, “It requires too much maintenance”, so we take a leap over the fence or uproot the old grass, hopeful that the new place or new seeds we sow will reap greener grass throughout the seasons.

I’ve had it. 

I’ve been fascinated by my own inherent Dark Ambition Syndrome, jumping over fences and ripping up lawns since leaving school 14 years ago. Let’s get one thing out of the way, I’m an insecure overachiever, and my ambition far exceeded my talent. Fortunately, I’ve learnt how to hustle – from the best, my mother. This matters, because hustle beats talent when talent doesn’t hustle, and hustle doesn’t bustle when ambition has no muscle (quote me on that rhyme – #copyright).

I grew up in a middle-class family in Benoni (same city as Oscar-winning actress Charlize Theron, and Princess Charlene of Monaco). My mom personifies the word “hustler.” Not only did she sell raffle tickets for a big-screen TV contest to raise school fees so that I could attend a private school (Treverton), but she also had to “discuss” a few things with my school principal over the years.

One particular event stands out: when I brought a copy of “Hustler” magazine to my Afrikaans conservative primary school. I promise you, this was with innocent intent… Inside the issue, my local horse-riding instructor had posed with Michelle Pfeiffer for some perfume advertisement. I think (I can’t even remember). He was holding/covering her breasts – so no naked boobs.

I obviously did not take notice of the other crude pictures in the magazine. I simply wanted to show off to my (then very limited) group of friends that I knew someone famous… Needless to say, I didn’t become Head Girl or Captain of the drum-majorettes, but my mom did handle the situation like the queen she is and averted my expulsion. I think she bartered with my supernova grades (#nerd – did I mention that?), and pretty fast sprinting capability for the athletics’ relay team.

So what? Similar to many individuals with thriving Linkedin profiles, impressive track-records or trophies on their dust-collecting shelves, some of us are chasing the approval of others as opposed to affirming ourselves and, in so doing, we miss the present. We share dark ambition syndrome, the hungry lion that simply can never satisfy its hunger. If you have converted your carnivorous lion into a vegetarian—good for you. You can stop reading now.

My DAS can be traced back to younger years, for sure—not being pretty enough, rich enough or cool enough.

My parents did a great job (I love you ma & pa), but society raised a hungry lion in captivity anxious to prove strength and resilience in the pack.

So, when graduating from varsity, it was like I was let free to fend for myself in the wild. Ever since, my personal struggle with dark ambition syndrome has been a tireless, anxious race to impress fortune 500 company boards, roll-out a list of qualifications, smile at a portfolio of personal good investments, take my family on a magical around-the-world trips, wear expensive name brands, look picture perfect, be charming and have many followers / friends.

See I’ve chased the approval of others in many ways, examples (non-exhaustive) include:

• I brought a crude magazine to school to show my friends that I was cool—FAIL.
• I spent textbook money at the bar to impress varsity friends.
• I risked my parents’ house as surety on a huge student loan to study my second masters’ in Germany, to prove to others I am smarter (regardless, I still started at the bottom as a services intern with 2 masters degrees-  cum laude).
• I broke up with my first love (and original co-founder of Emptytrips) multiple times, because I thought he was holding me back (millennial bullshit).
• I emotionally (hastily) resigned from a promising career, at a great firm (BCG), to prove they made a mistake in not promoting me fast enough.
• I risk my savings, health and stability to “pioneer” a tech company against legacy giants to call myself a “visionary entrepreneur,” “uberising a white space” which simply increases dopamine hits via my social media following.
• I bootstrap and burn both-ends of my energy candle by consulting (seedpitch) to fund my flagship (empty trips) and to still pay for drinks (some of them the same varsity friends mentioned at above).

The above is Dark Ambition Syndrome at work, and it should seriously earn syndrome status! I believe that this is what leads to a pattern of “jumping over the fence” or searching for greener grass. A theory is that DAS (like many syndromes) are linked to your childhood: the years where you either form a healthy or competitive perception of happiness and success.

The big pitch. 

Fast-forward to the pitch competition at the Start-Up World Cup in San Francisco, which entailed also drinking vino in Napa Valley and touring through the Big Sur on a road-trip up to Los Angeles along the coast. How fortunate I was. I say fortunate, as many will not have the opportunity to do all of the above, especially if living in Africa:

1. It is very far away.
2. Our local currency doesn’t get far (albeit stronger of late).
3. We get homesick.

But during the trip, instead of feeling euphoria, I felt an ocean of frustration, exhaustion, anxiety, self-criticism, disappointment and regret. We did not win the Startup World Cup, or the $1m investment.

However, an MIT initiative technology that can diagnose leukemia non-invasively in 60 seconds took the WELL-DESERVED trophy. They rock, and considering a friend of mine passed away (younger than me) a few days prior to the event, their win was very relevant to me (#phundu). Well done Leuko.

But I had never been as prepared for anything in my life as I was for pitch day. I had presented to anyone who would listen (even my uber drivers), I ran it over in my head cooking, driving, peeing, sleeping—you get the gist.

As a participant, you are allowed two minutes ONLY to explain the idea, the market size of opportunity, the traction, the differentiation, the team, what you need the money for, and what the growth strategy is. Add some cool slides, personality, Calmette and you’re in. (You can watch a 2 min practice run of the pitch here). On the day, I ran out of time two slides from the end as I added too much personality and an unplanned joke, but I had fun on stage and, hey, people who save lives should win.

For the rest of the start-ups, I believe the organisers should have defined what “early-stage startup” meant, as some of the other companies competing had raised millions of dollars in funding, and have been around for 4+ years etc… It was like racing college track athletes against my crawling toddler (to be clear, Empty Trips is 13 months old and has raised <$500k. We are early-stage.). The playing field was not level, but then when is anything in life fair?

DAS just made the shadow of losing darker, one dull spot in my beautiful garden became the focus … I’m definitely not bitter and not bi-polar, it was just Dark Ambition Syndrome coming to play in my garden.

Coming home from San Francisco to Johannesburg, I was conscious of the turmoil of emotions … I felt the need to jump the fence again, escape, find new grass, oh the familiar feeling!

DAS would persuade my mind that a move to Silicon Valley, where cars drive themselves and venture capital funding flows freely, would help Emptytrips go to the next level. That I would be a better CEO if I was less stressed about cash burn, and more focused on product capability… That entrepreneurs have more support, and the ecosystem is more stable with corporates more willing to let go of legacy processes. Bla Bla Bla.

But not this time DAS, not this time… For the first time (in a long time), I want to stay right where I am.

To deal with DAS, always make a list of pros and cons for your personal scenario, e.g.:

• South African investors are more risk-averse than Silicon Valley hotshots—this has made me a prudent founder.
• South African investors want tangible traction—this ensured we proved use case with a solid team before wasting money.
• South African VC is your funder of last resort– this enabled us to build strong client relations to fund our journey, stay committed and at, thereby, mitigate risk.
• South Africa is not known as a “tech-hub,” but here you can find great talent for fair value. (You remember Elon Musk is South African right? #smartpeoplecomefromSA)
• We have crime in CBD (Hillbrow), but downtown San Francisco was filled with homeless people.
• Lastly, South Africa might not have a stable political situation—but hey, America also has their woes with Trump.

So, in essence: “Calm down DAS—I ain’t going nowhere!”

South Africa is a place where you can enjoy a bottle of great red wine and eat a 400 gram (perfectly chargrilled medium-rare) fillet-on-the-bone steak, for less than US$30 (instead of $120), whilst discussing weekend trips to safari lodges or vineyard weddings in Cape Town. We also have Uber, and Airbnb—same, same. The only difference between a tech founder in San Fran and myself, is that I get to go home to a warm home, with a large pool, adoring dogs, a loving fiancé and scented candles, all without needing Zuckerberg’s valuation.

The income disparity in South Africa is severe, a legacy problem, but I will leave politics and the lack of good education to the elected leaders to whom I pay my taxes. Those who have been able to get ahead or have been privileged are able to live great lives in South Africa, lifestyles that you simply will never afford in other countries. In the same breath, our great lives come with an obligation: we need to create great impact right here at home, in our own backyard, fertilizing our own lawn and supporting our own entrepreneurs.

We have some ongoing issues regarding crime, corruption and education, but any country does. Overall, however, we are on the right track. If we support our political leadership to rip out the “weeds of corruption,” our corporates strategically fund start-ups and even-out the playing field for all entrepreneurs (regardless of race or gender), then we can reap great benefit from our beautiful land and uplift millions that live impoverished—still.

What we often forget is that winter passes (most of the time) and that spring is on its way… In summary, to quote James Openheim, “the foolish man seeks happiness in the distance; the wise grows it under his feet.”

Hustle hard, play nice and tame your DAS beast.