The Making of Desperate Entrepreneurs

Bet you’ve seen or worse, worked with one. These special breed of entrepreneurs, or for the lucky ones, is just a temporary phase, usually portray one or more of the symptoms below:

  • Change company direction every 3 days
  • Change team member’s and staff’s roles every 3.5 days
  • Quote Sir Richard Branson and his 500+ companies
  • Use the term pivot too often
  • Do the “pivot” lagi more often
  • Jack of all trades but master of none
  • 5 years later at the school reunion, he’s still working on that idea/startup with no apparent growth (his mom secretly texts you to help “advice” his son)

If entrepreneurship is a mix bag of many skills, traits and mojo, then the equation for desperate entrepreneurs are:

Desperate Entrepreneurs = Balls of Fire + Balls on Fire + Tons of Unpaid Bills + That One I Also Can Ao + Slap-Worthy Ego - FOCUS

Just like my favourite Add. Math teacher, Good Ol’ Mr. Cheng, would say, “Let’s breakdown the equation.”

Balls of Fire


Entrepreneurs are passionate creatures, and usually optimistic (or overly at times). They are risk takers too. Normally these two characteristics are good ingredients in the making of a good entrepreneur, but just like how too many bad spices can mess up your miso soup, they can totally work against the person.

Balls on Fire

Ever had someone bring a Bunsen Burner near your balls in the science lab? Entrepreneurs are grilled almost every day, and the chef in the BBQ apron comes in different shapes and sizes – investors, VCs, grant-givers, not-savvy financiers, banks, self-appointed/justified mentors. Unrealistic growth goals, lack of domain experience, constantly missing KPIs are some of the reasons why the financial backers fire up the BBQ pit in the first place, and the entrepreneur usually feels the heat the moment they are taken out to be defrosted.

Tons of Unpaid Bills

'This one's called 'unpaid electric bills'.'
‘This one’s called ‘unpaid electric bills’.’

Having a low monthly overhead (business and personal expenses) is key, and growing the war chest is advisable. The world of business is like a sandwich date with Lindsay Lohan and Paris Hilton; you just don’t know what’s in store around the corner. If you’re not prepared enough, your bills will start getting unpaid, you start paying interest, and thus begins a spiral downwards. Personally, I went through that too over the last four months, and let me tell you, aside from noisy neighbours and a broken fan, nothing keeps you up at night more than the thought that in every passing second, the interest on your debts grows. #truestory

That One I Also Can Do

Not sure if it’s a pro or con, but entrepreneurs are usually multi-talented and multi-skilled. If applied properly, that’s a huge pro. But sometimes when the entrepreneur is put in a hard and hot position, he will start looking around and realise there are many other ways where he can pay his bills. I’ve also fallen into this trap many times before (no, I’m hardly multi-talented, but just prone to itchy-backside and bad decisions), and after pulling myself out of the holes for too many times, I devised a simple process of three questions:

  1. Does this go into growing my business and brand?
  2. Can I close the deal within 3 email exchanges and get paid in less than a month?
  3. Will it take me longer than 4 hours to execute it myself, or 4 hours to manage someone else to do it?

Notice that I don’t add growth questions like “Will this develop my skills and knowledge?”, or “Will this make me a better person?”. Those are the questions that usually will fool you into thinking that the opportunity is worth pursuing, and one that you come to regret later.

Slap-worthy ego


Confidence is an interesting thing. Without it, you get pushed around, can’t decide what to wear or to ditch that asshole of a guy. Too much of it, you become overly-optimistic, cocky, and plainly just a dick. Add a dose of stubbornness inside, and you’ll come face-to-face with the crippling force of ego-land. Don’t get me wrong, nothing attracts me more than an individual who is sure of himself and his capabilities, but I also know stupid when I see one.

Lack of Focus

Keeping your eyes on the goal despite being thrown around, yanked aside and tombstone-piledriven into the floor, is hard work. Always flexible with the means taken but firm with the end goal, and knowing when it the best time to pull the plug are what separate the good entrepreneurs from the bad ones. It’s just funny how the moment entrepreneurs get desperate, they become short-sighted and develop tunnel vision. How would I know this? Same answer as the guy who sticks a bottle of Tabasco in his nose and have burning tears streaming out of his eyes. Been there, felt that (no, not that stupid Tabasco stunt) #overlygraphicmetaphor

In truth, we all have been a desperate entrepreneur before. Some, like me, still becomes that every season. My best advice? Find comfort in self-reflection and reaching out for help. I know. It’s hard too. 🙂


Co-Founder of KICKSTART by night, Talent Development Consultant, organising workshops and conferences by day, and full-time single dad in between, Maverick is pretty much a renegade. An ex-monk who's always first to ask "why not?", Mav enjoys hacking the way things are done, and pretty much happy with the success rate of 50% (coz sometimes mom is right after all...). When it comes to business, give him a million bucks and he'll most probably get a new set of gadgets, drive home an Audi R8 and reload his Starbucks card. But give him little to nothing, and see how he starts switching on the little brain-matter between his ears. Challenge ACCEPTED!

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