Coping with startups.

Pranshu Maheshwari
How to Start a Startup @ Penn
4 min readSep 23, 2014

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On the emotional challenges of starting a company

Startups aren’t easy for a whole variety of reasons, but the emotional challenges of starting one might just be the hardest part.

One of the major causes of this is the constant uncertainty around success and failure. The questions we face can all be potentially life or death. The next round of funding, a key piece of tech, the next few clients; there are challenges that we face every week at Prayas that we know will set us back considerably if we fail at them. While the destructive power of these challenges goes down with time, it never quite goes away — even more mature tech startups face the uncertainty. Foursquare recently pivoted away from their check-in and gamification based social network (even if they don’t quite admit it was a pivot). This is a startup that’s onto its series D, with over 100 employees, and they are still facing the uncertainty. As founders, the bulk of the uncertainty rests on our shoulders, and it can be hard to deal with.

What makes the uncertainty worse is how invested we are as founders in our own companies. We want our startups to succeed more than anything else. This involves sacrifices. Hobbies are left along the wayside, there’s little time for friends and relationships anymore; student founders no longer study for midterms, and parent founders miss their kids’ birthdays. Indeed, many compare starting a company to having children; lacking a couple of young’uns running around myself I can’t confirm this, although I empathise with the feeling (and hope my children grow at a normal pace, rather than in a startup’s entrepreneurial exponential bursts.).

Growth becomes our primary success metric. Good weeks take us to the moon and back, and bad weeks drop us off on the way. Founder emotional volatility spikes so much that John Merriweather could run a hedge fund off it if it was indexed. The day we signed our first client at Prayas was one of the happiest days of my life, and it made us believe that we were well on our way to success. However client number two took a long time to come around, much longer than the first client did. It was hard to get in touch with people on the phone. Micro failures more than made up for our single macro success. Each day that passed until we finally got in touch with the right client made us question whether we had created a company that actually has a viable product.

More than our own, other people’s success plays havoc with our emotions. I remember a phase when every time I heard of a new competitor my heart would sink a little bit because I felt that we didn’t have a chance. Client and investor feedback was particularly painful. We had several bad pitches to retailers and VCs – some of whom thought we were crazy, and most of who thought (and probably still think, for good reason) we were stupid. Eventually entrepreneurs develop a bit of a thick skin to emotions in general, but until the crocodile callouses emerge to protect you from criticism, each comment stings.

But developing the emotional resilience to keep going is the key to success. Not quitting is so much of the startup’s struggle, because if you can survive, you can make it. Paul Graham has a great essay on this, where he says:

When startups die, the official cause of death is always either running out of money or a critical founder bailing. Often the two occur simultaneously. But I think the underlying cause is usually that they’ve become demoralized. You rarely hear of a startup that’s working around the clock doing deals and pumping out new features, and dies because they can’t pay their bills and their ISP unplugs their server.

Intuitively it makes plenty of sense – if you do it for long enough, you’ll eventually learn from all your mistakes and get good at it. But just like Paul Graham mentions, persistence is hard, because dealing with failure isn’t pleasant. It’s demoralizing. It is harder still if you have kids to feed, because then success isn’t just a matter of pride, but also a matter of putting food on the table. For some of us, failing consistently is just not an option.

This side of startups is not what people first think of when they imagine the highflying, diamond studded sweatshirt wearing, Silicon Valley techie, but it is the harsh reality of an entrepreneur’s life. It’s what we sign up for when we take on the challenge of creating something, that one day will affect the world at large through our efforts. We dream of changing the way the world communicates like Facebook did, or transforming how we find information like Google did, or forcing internet providers to give everyone faster speeds like Netflix did. Or on a smaller level — of pioneering a whole new kind of swipe based interface like Tinder is, or requiring that every smartphone comes with a front facing camera like Snapchat is. Those days when it seems like our vision will escape from our hazy hallucinogenic dreams to disrupt society’s reality are what keep us going, despite everything. All the long nights, missed occasions and lost relationships make sense when things work out.

But when things don’t, it’s time to get back to dreaming, to start all over again.

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