LESSONS FROM A SERIAL ENTREPRENEUR -----ANSHUMAN BAPNA
There are No Obvious Patterns in Entrepreneurship.
You Must find Unique Solutions for Yourself
Serial entrepreneur is a funny term. To the curious mind, the obvious next question is if there is a ‘parallel entrepreneur’ too? Perhaps someone who’s running multiple companies at the same time? Before you laugh, though, remember that Jack Dorsey (Twitter and Square) and Elon Musk (SpaceX and Tesla) would probably qualify as parallel entrepreneurs. And from the quality of these entrepreneurs it should be evident that you need to be made of supernatural stuff to pull off startups in parallel. So for the rest of us mortals, let’s stick to serial entrepreneurship for now. There’s also the rather unfortunate association with serial killers (or ‘repeat offenders’, if your term of art is repeat entrepreneur). Now how many murders does it take before you ascend from being a common criminal to the pantheons of serial killers? I’d say definitely more than two. And yet, we often label our second-time entrepreneurs serial entrepreneurs (myself included). To me, that suggests we believe there’s something truly pathological about starting a company twice. The first time perhaps you got carried away—your annoying boss, your overbearing peers or just the seduction of ‘if-he-can-do-it-so-can-I’. But to do it all over again? My God, you must be crazy! To some extent, I would agree. I started my first company (righthalf.com) while I was in my final year in undergrad at IITBombay. A bruising 12 months later, I had sold the company but also resolved to never go near a startup again with a 10-foot pole. A decade later, here I am, running a new startup (mygola.com). It’s a bit like pregnancy—after the interminable wait, a painful labour, you resolve that this is it. And a year or two down the line, you’re back staring at the same hospital walls wondering what happened. But starting your second company comes with some perks. One of them is supposed to be enhanced powers of pattern recognition. You’re supposed to now know what works, and what doesn’t. As a result, the startup world is awash with self-professed gurus spouting amazing stuff learnt from experiences. Polite society would call them wisdom, truths or axioms. I prefer to call them clichés. The trouble with clichés is that they have a kernel of truth but they also give you absolutely no insight into your specific situation. Here are my favourites.
Pivot or Stick to It?
Listen to your customers carefully, they’ll say, keep iterating and if your success metrics don’t match up, change the model—sometimes, even the business you’re in. That’s a “pivot”. That sounds completely legit, until you hear some other icons talk differently. Mark Zuckerberg, who says that nothing that’s worth building is easy to build. Or Peter Thiel (the founder of PayPal), who keeps lamenting how entrepreneurs are so focused on incremental things that one of the biggest innovations of the last decade was 140 characters, and not flying cars. In my own startup, we’re trying to fundamentally change how travel planning is done worldwide—so far with limited success. And yet here we are, slogging away on the same problem. So is there a line between inspirational determination and sheer stupidity? Or does success rationalise whichever worked? You know what my hunch is.
Work-Life Balance?
As a young father, this one vexes me no end. Travel is a hyper-competitive category, particularly when we’re trying to beat better-funded companies globally. Clearly, the company needs a remarkable sense of urgency, even paranoia. In my first startup, there was a simple translation for that: work 20 hours a day. But if you’re building for the long term, can you really afford to burn the candle at both ends? How do you build for the long term by neglecting things that let you keep your sanity—whether it’s family or your pastimes? “Startups are an intense dash to beat others to the finish line”. “No, they’re a marathon where you’re competing against yourself”. OK, can someone let me know which Olympic event I’m running in when they press the trigger?
And the answer is…
As a serial entrepreneur, the most obvious pattern I’ve recognised is that there isn’t one. Every single one of these ideas has worked for some entrepreneur or another. But they need not apply to you for one of a million possible reasons. So you learn a new trick—hold every possible cliché and the anti-cliché in your head at the same time, ready to accept either or reject both. You’re not wedded to one approach over another anymore and everything seems more clinical, more impulsive and even, umm, coldhearted. Funnily enough, if you did that to people, your behaviour would be pretty close to the accepted definition of psychopath. So there was something to that serial killer analogy after all!
Listen to your customers carefully, they’ll say, keep iterating and if your success metrics don’t match up, change the model—sometimes, even the business you’re in. That’s a “pivot”. That sounds completely legit, until you hear some other icons talk differently. Mark Zuckerberg, who says that nothing that’s worth building is easy to build. Or Peter Thiel (the founder of PayPal), who keeps lamenting how entrepreneurs are so focused on incremental things that one of the biggest innovations of the last decade was 140 characters, and not flying cars. In my own startup, we’re trying to fundamentally change how travel planning is done worldwide—so far with limited success. And yet here we are, slogging away on the same problem. So is there a line between inspirational determination and sheer stupidity? Or does success rationalise whichever worked? You know what my hunch is.
Work-Life Balance?
As a young father, this one vexes me no end. Travel is a hyper-competitive category, particularly when we’re trying to beat better-funded companies globally. Clearly, the company needs a remarkable sense of urgency, even paranoia. In my first startup, there was a simple translation for that: work 20 hours a day. But if you’re building for the long term, can you really afford to burn the candle at both ends? How do you build for the long term by neglecting things that let you keep your sanity—whether it’s family or your pastimes? “Startups are an intense dash to beat others to the finish line”. “No, they’re a marathon where you’re competing against yourself”. OK, can someone let me know which Olympic event I’m running in when they press the trigger?
And the answer is…
As a serial entrepreneur, the most obvious pattern I’ve recognised is that there isn’t one. Every single one of these ideas has worked for some entrepreneur or another. But they need not apply to you for one of a million possible reasons. So you learn a new trick—hold every possible cliché and the anti-cliché in your head at the same time, ready to accept either or reject both. You’re not wedded to one approach over another anymore and everything seems more clinical, more impulsive and even, umm, coldhearted. Funnily enough, if you did that to people, your behaviour would be pretty close to the accepted definition of psychopath. So there was something to that serial killer analogy after all!
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