The Startup Roller Coaster

In 2010, I heard a talk by angel investor and entrepreneur Howard Anderson about the emotional roller coaster that comes comes with launching a new technology venture. He explained how the highs are so high, while the lows feel really low.

For those of us in the room who had never been in the position of launching a company, it didn’t sound surprising. Of course the pressure will be intense, and incredibly risky. But how extreme could the highs and lows be?

Extremely extreme, as it turns out.

I worked in large organizations for more than a decade. A bad day at an established company might entail sharp-elbowed office politics, hurt feelings, and worry about career advancement or a raise. Worst cases involved the loss of a job. But in most situations at a large company, problems will eventually be worked out. Everyone knows the organization will endure.

Startup Roller CoasterNot so at a startup. Before you’re funded or generate revenue, the venture is fragile. Things move fast, there is too much to do, and the sense of responsibility is huge. Even minor problems feel big, and failure of the business can take many forms.

Conversely, the accomplishments feel huge. Hard work, a new product out the door, positive feedback from customers (or, in the case of my company, readers), and lucky breaks can really boost your spirits. When a bunch of things are working well at the same time, the feeling is spectacular.

Then the crash: reality checks, unforeseen problems, pushback, lack of alignment, and the flat-out “no” when you were hoping for a “yes.” These and other issues can really throw a wrench in the works.

There are ways out of the funk, though. Keep on executing. Work through or around the problems. Reach out to your partners or customers or mentors or anyone who might be able to help with a new approach or pivot. The wins begin to trickle back, and the cycle starts again.

A few years ago, I met an experienced startup founder at the Cambridge Innovation Center. She was very familiar with the entrepreneurial roller coaster, and offered some advice on how to handle it.

Highs and lows on the startup roller coaster

“For the highs and lows, be careful of what you do on those days,” she said. For instance, on a good day when you get a big win like recruiting a customer, call your investors and tell them about it.

She also alluded to things founders should not do on the bad days. She didn’t have enough time to explain what they were (it was at the end of a late-night meeting) but one of them I have been able to deduce from multiple sources (including Y Combinator founder Paul Graham), as well as Howard Anderson’s reminder at the end of his talk: “It’s always darkest before the dawn,” he said.

In other words, keep pressing ahead, even when the world seems to be working against you. And don’t give up.

The above image is a creative commons licensed image from Tanki on Flickr.

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