Chronicles of a Struggling (Succeeding) Entrepreneur: The Underworld of Startup Entrepreneurs

I am on a blogging marathon promoting of my upcoming 3rd book (28 October 2015), The Anxious Entrepreneur. Pre-order it at up to 40% discount.

The fridge was empty. I swore to myself that the following day I would hustle like I never did before. I don’t know why but the implication of an empty fridge hurts more than not eating the actual food. This can’t be 3rd world problems, can it? Things got better as they always do. Months later I was back in a similar situation of having a horribly empty refrigerator. My life has seen a rollercoaster of these episodes.

I must do some shit to rid my life of such constant low points, forever. This is what makes none believers not understand why folks like me sacrifice to push what is called a “dream”. Can I get an ‘Amen’?

On the other hand, like the rest of society, I don’t like to keep it real. It is like I paint a champagne life with a cheap BIC pen.

You know what kind of society we are?  We are a people who when given directions, dish out driving directions. We know very well not everyone has or can have a car. For goodness’ sake we are labelled a developing world, a 3rd world country.  Poverty is rife. Our unemployment can drown Noah’s Ark.

Anyway, we don’t care. Driving directions are the order of the day. Even job interviews, conferences and other event shapes events give driving directions. I guess keeping out public transport directions assumes and maintains prestige.

I wanted to co-write this article with a friend but he refused as he doesn’t want to be construed as a “loser”. He is doing very well. But I understand his position.

Like the rest of society, him – me – you – us – everyone, are bias in projecting success. Only winning strokes make it publicly.

I heard someone say “why does ‘X’ put himself through this shitty hustling lifestyle even though he has a degree?”

Entrepreneurship is tough. It takes you through several moments of insanity. The things entrepreneurs sacrifice to achieve their uncertain ambitions are UNBELIEVABLE. But this article isn’t about why people choose entrepreneurship.

There is a good article published by The Economist titled “Instead of romanticising entrepreneurs people should understand how hard their lives can be”. You should check it.

What will follow is the truth. If you are an entrepreneur this is the gospel. It is the underworld of startup entrepreneurship.

Aspiring entrepreneurs, ahead you will (probably) encounter what is to follow:

Obviously some of these happened to be me, but not all unfortunately. I borrowed some. At least I have struggle credentials. I am writing this stuff because I hope it will firstly humour you. Secondly, this sh*t happens, to get to point B – sometimes ideals have to be skipped. When such is forewarned and when it actually occurs, it humours. And when it is told, it is humour. “Comedy is tragedy plus time”, even google is unsure who said this, but it must have been some comedian as the legend goes.

  • I saw a guy at a restaurant in Pretoria wearing a green suit. The following day I saw him at a conference in Sandton with the same suit. In my head I gave him a nod and said “right on brother, do your thing. Only respect”. And the following week I saw him again with the same suit. I am kidding, I never saw him again – maybe because he changed.
  • Thanks to Lesiba for sponsoring over 70% of that day’s lunch at Fish and Chips. Lunch for 3.
  • Killing time by playing with kids, because you can’t afford to go anyway or borrow the acquaintance of a lady.
  • Walking for 2.5 km to a meeting. Or 4 km. Or more.
  • Waking up to do best with the R10 airtime you have to push progress.
    Luckily, no, by God’s Grace a friend buys you R20 airtime.
  • A quote from that friend mine. I stole it from our group chats: “I wake up today Monday 28 June very broke, haven’t been this broke in a long time, though in a life on an entrepreneur one has been through these moments a lot of times but one should never get used to it. Nonetheless I woke up with one plan in mind: chase as many people as I can for appointments with the R20 airtime that I put on this phone. You know to keep every call to 2 minutes at least and get that person’s email address. That is what we call maximising resources, Hustlers Verse 1. To all entrepreneurs know one thing: some days will be hard than others, but always be persistent on your journey.Hustle hard”.
  • Abusing your Blackberry keyboard to send multiple emails because you are out of data bundles on your laptop.
  • Computer hijacking because you don’t have one, i.e. using someone’s laptop when they are on a break.
  • Walking distances, again. And again.
  • The easy part is moving back home because you cannot afford yourself anymore. If you are currently going through this, tears won’t help you.
  • The harder one is moving in with friends. Especially if you are a ‘caring’ person who wholly respects other people’s space. I don’t understand how some people who borrow someone’s space and not keep it clean like their hosts.
  • Revisiting old deodorant bottles as you’ve just totally exhausted the latest. No money for news roll-on.
  • Calling your mom as a last option and asking for money to get to your meeting. It is a potential meeting; but you know it could go either way.
  • Cancelling a meeting as you don’t have funds.
  • Walking distances in the sun. You need lots of sunglass pairs if you are an entrepreneur. I am left with 1 pair, maybe it means I finally making it.
  • Walking 2.9 km from Sunninghill to Woodmead as you took the wrong taxi. Misdirection boss.
  • Wanting to lick someone for giving you R10 for airtime.

Hang in there, don’t worry. You are going to win.

Chris Gardner as we saw in that movie “The Pursuit of Happiness” went through some testing times. One of my favourite scenes was when he gladly, but reluctantly, lent his boss his last dollar bill to pay off a taxi. The boss assumed a dollar bill isn’t much for a guy in a nice suit like Chris.

Chris Gardner faked it.

The number one enemy in South Africa for the youth (and I am only saying this to stress a point; I am not a doctored social scientist whatsoever) is maintaining an assumed class. Twitter is one of the barometers for this fallacious class. The solution lies with the individual. Know the world likes to pretend ideals, know your situation and do venture into your goals – even if it upsets class ideals. Sometimes, don’t be afraid to fake it.