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How entrepreneurs navigate the difficult moments they’ll inevitably face

Tips for surviving the not-so-glamorous side of entrepreneurship.

How entrepreneurs navigate the difficult moments they’ll inevitably face
[Image: Jakob Petersen/Wikimedia Commons]

The media often portrays the startup founder’s journey as a glamorous one. Here’s how the story usually goes: entrepreneur comes up with a brilliant idea, finds investors to fund it, builds a perfect initial product, nails down his or her first customers, and uses that momentum to grow the business at a fast pace.

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But while the news may emphasize the positives, an entrepreneur’s journey often takes a few dark twists and turns. If you talk to enough founders, you’ll find that for every up, there’s usually a down just around the corner–whether that be a missed forecast, a product shipped without a critical feature, or a principal engineer who decides to quit. Even uncontrollable circumstances like natural disasters, catastrophic events, or just bad timing can send entrepreneurs into a downward spiral. And when these dark moments occur, an entrepreneur has two options: throw in the towel or persevere.

I won’t sugarcoat it: Digging deep can be hard. But pushing through the lowest of lows and working until you hit a mental or physical limit helps you come out the other side stronger, and makes you more resilient to future roadblocks.

This week on Zero to IPO, we talked to three entrepreneurs about career-defining low points. Here’s what their stories taught us.

You need to be obsessed with your idea

To turn a major hurdle into an opportunity, have so much passion for your vision that giving up isn’t even on your radar. Amy Pressman, cofounder of Medallia, and her husband (and founding partner) had a grand idea to disrupt customer experience technology, starting with the hospitality industry. However, their first big opportunity came at an unfortunate time–they pitched Hilton on September 10th, 2001–the day before the devastating events of 9/11. Their funding was halted.

When it comes to timing, it doesn’t get any worse. Even when faced with the bleakest of outlooks, Amy knew they were onto something. It was this unwavering faith in the idea that led to Hilton’s initial interest in a trial and enabled them to build momentum.

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You can combat sheer terror with focus

For entrepreneurs, the feeling of panic is all too familiar. During the early days of building LoudCloud, Ben Horowitz, also the cofounder of Andreessen Horowitz, found that restful nights were few and far between. For the six months of good times he experienced, he endured seven and a half years of sheer terror.

Out of money and on his roadshow to IPO in 2001 (coined “the IPO from hell” by journalist Ben Elgin of BusinessWeek), he faced constant stress as he watched the Nasdaq fall like clockwork each day. On top of that, he saw their “comps”–the comparable companies that LoudCloud was being evaluated against–get cut in half. Just as he thought it couldn’t get worse, he received a phone call from his father-in-law that his wife had collapsed. He knew he should return home, but she told him to stay–they both knew that bailing during that critical time would have led to bankruptcy.

For Horowitz, the rest of the roadshow was a blur, but he managed to cut out the noise and zero in on his plan. He even showed up to one meeting with a mismatched suit jacket and pants, epitomizing his level of focus on his idea–and not on his wardrobe, or anything else–during such a difficult period. For entrepreneurs facing uncertainty, zoning in and letting go of everything circumstantial can make room for focusing instead on the elements you can control.

Don’t go it alone

When you see a hundred reasons to walk away, there are often just as many to keep going. But you don’t have to do it alone. Turning inward and practicing self-coaching can help you become your own most prominent advocate, but you shouldn’t be afraid to pull in others. Jawbone founder Alex Asseily discussed how leaning on support from mentors and friends enables entrepreneurs to see their idea in a new light, question their assumptions on the business, or even challenge the entire concept itself.

And aside from providing a sounding board for ideas, teaming up with a friend or colleague often leads to higher success rates than building a company solo. Cowboy Ventures statistics show that a supermajority of venture-backed, U.S. based tech companies (86%) have cofounders, and 85% of those cofounders have a history of either going to school together, rooming together, or working with each other. Plus, as Asseily can attest to, having a go-to couch to crash on when someone kicks you out of your office space isn’t necessarily a bad thing, either.

Relying on others can also mean staying open to the idea of relinquishing some level of control. When Todd and I started at Okta in 2009, we faced our fair share of “oh, shit” moments–falling short of revenue targets, low customer count, missed projections–partly due to our unwillingness to part ways with responsibilities we took on in the early days. As we brought on seasoned experts to fill the leadership positions that Todd and I had previously split, we were able to change the course of the company. We did it as a team. And we learned nobody builds something worth keeping without going through hell and back first.

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Frederic Kerrest is the COO and cofounder of Okta. You can listen to the full episode, “The Oh Shit Moment” wherever you get your podcasts. Tune into Zero to IPO every Tuesday and check back here each week to read more about the insights on each episode.

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