The 17-year-old’s hand shook as he raised the gun to Zeb Evans’ forehead. Adrenaline overwhelmed Evans’ body as the metal rubbed against his skin. Then, in that moment of extreme uncertainty, he gained clarity.

His identity didn’t need to be defined by a diploma.

“I had that realization when I had the gun pointed to my head—that this isn’t what I want to do with my life,” Evans says.

Evans was an undergraduate student when he was a victim of a home invasion robbery. Fortunately, he wasn’t harmed, but his future had a new outlook.

“[I realized,] I don’t want to go work for someone else. I don’t want to continue learning business, because you learn business by doing,” Evans says.

“[I realized,] I don’t want to go work for someone else. I don’t want to continue learning business, because you learn business by doing.”

The next day, Evans dropped out of school and started working as an entrepreneur. Twelve years after the home invasion, Evans is now CEO and co-founder of ClickUp, an all-in-one productivity management tool valued at $4 billion.

The robbery wasn’t the only near-death incident that shaped Evans’ journey. Since that fateful day, Evans has experienced a number of life-changing moments that have informed his entrepreneurial path and contributed to his current work: disrupting the project management industry with ClickUp.

A Bedridden Entrepreneur

When Evans was 10 years old, he suffered an accident that put him in the hospital for months. In a time without modern smartphones or tablets, Evans got his hands on the one public laptop at the hospital. While bedridden, he started playing around on eBay and Alibaba, looking at products and discovering what was selling.

“And that is where I started marrying my love for entrepreneurship with technology,” Evans says.

He began buying and selling Disney DVDs locked up in the notorious “Disney Vault,” with some discs valued up to $100. His business acumen continued into high school and college, where he started an entertainment company to manage local musicians.

Following his second life-threatening experience in college (the home invasion robbery), Evans faced the prospect of an incomplete degree, lingering side hustle, and no capital. He found his most valuable asset within his entertainment business: the custom social media tools that he’d built from scratch.

“Twelve years ago, that stuff didn’t exist,” Evans says. “I just always wanted to create things and give people experiences. It was just always inside of me.”

So he started the aptly named Fast Follwerz, a social media marketing firm which quickly became one of the largest firms of its type in the United States.

But something was missing, and it would take another meeting with death for Evans to discover what it was.

Fed Up With Fueling Ego

Four years after founding Fast Followerz, Evans had a seizure in a movie theater. After multiple tests, Evans anxiously waited for a prognosis. His father had a brain tumor while Evans was growing up, and Evans assumed the worst.

“During that week … I realized that we [Fast Follwerz] weren’t really adding much net positive to the world,” Evans says.

In his view, the social media industry was more about ego than community. And Fast Followerz was fueling that ego.

“I kind of wanted to right those wrongs, so to speak,” Evans says. “But I also wanted to create something that had a much larger impact.”

“I kind of wanted to right those wrongs, so to speak. But I also wanted to create something that had a much larger impact.”

His latest health scare turned out to be an anomaly, not a tumor, but it motivated Evans to sell his social marketing firm and move to where all bright-eyed entrepreneurs dream of: Silicon Valley.

Evans had imagined Silicon Valley as “Vegas with startup lights,” but he found the reality of Palo Alto had less glitz than the Sunset Strip. “Palo Alto is the sleepiest town in the world,” Evans says. But he wouldn’t get much sleep during his first year in the Valley, which he spent working on his next business idea.

Mimry was Evans’ first from-scratch tech startup. Alongside his business partners, he developed a video social network app to capture moments in users’ lives from a first-person point of view. The goal of Mimry was to remove the ego-focused aspect of social media that had irked Evans while he ran Fast Follwerz.

The problem was that many people are drawn to the ego-focused aspect of social media. Mimry folded within a year of Evans arriving in Silicon Valley.

Undeterred, Evans embraces the lessons he learned from that experience. “If I hadn’t done that one, I don’t think ClickUp would really exist today in the same way,” he says. “There are so many things that you learn doing your first tech business, regardless of how technical you are, that you just can’t learn unless you go through the process of it.”

After Mimry, he shifted his focus to battle another giant in the tech space.

The Solution That Became ClickUp

ClickUp started as a means to an end. Evans wanted to create a competitor to Craigslist by making buyer and seller communications safer. But before tackling his next startup project, Evans wanted to solve a productivity problem that had bothered him since his first business.

“It was just this clusterf**k of productivity tools. And they were supposed to make you more productive, but I couldn’t help but think that we were less productive by using all of these different tools.”

He started studying heavy-hitter productivity platforms like Asana and Trello to see if there were ways to unify their solutions. As he and his team began building their custom tool, they discovered they weren’t the only ones frustrated with the costly and complicated tech stack necessary for many businesses to get up and running.

“We thought it was just going to be an internal tool at first, aimed at saving ourselves time. And then we shifted that to saving the world time once we realized that there’s a huge need for this,” Evans says.

“We thought it was just going to be an internal tool at first, aimed at saving ourselves time. And then we shifted that to saving the world time once we realized that there’s a huge need for this.”

In 2017, Evans stopped battling Craigslist and started building an all-in-one solution for productivity, ClickUp. He set up the business in signature Silicon Valley fashion: a two-story house where the small team worked on the first floor and slept on the second.

Evans still misses the speed at which the team worked on their product in those early days. If they decided on a feature to build on Monday, they’d ship it by Sunday.

“It’s all about the product in the early days,” Evans says. “We were 100 percent community-led, 100 percent community-driven, and I was the product person—the only product person.”

The first version of ClickUp was built in six months using $2.5 million from the sale of Evans’s previous business. To compete with the productivity industry establishment, the team used an organic SEO strategy by targeting search terms associated with Trello, Asana, and productivity software.

Evans attributes ClickUp’s fast growth to the community of users and their active involvement in the product’s development.

“You have to use your users,” Evans says. “You can’t take action on everything, but you can take action on the trends, the common patterns that people continuously bring up.”

Scaling to Billions

ClickUp proved successful right out of the gate, and the team quickly outgrew its original house/office space. In 2020, ClickUp was named the best project management product by Proddys, the gold standard award for the product management community.

That’s when Evans started reaching out to investors for the first time. Investors were shocked that ClickUp wasn’t burning money and even more surprised that the company was profitable.

“If you can create a profitable business at first, you know you have a business,” Evans says. “Too many companies go and get funded, and they don’t have a real business.”

“If you can create a profitable business at first, you know you have a business.”

ClickUp raised capital through a high-net retention model—meaning they expected to expand their customer base, and then those customers would pay back tenfold.

“When you raise a lot of capital, it’s OK to grow inefficiently. But you have to understand how to [move] toward efficiency,” Evans says.

With a profitable model, investors, and active users, ClickUp has exploded in growth over the past two years and now has offices in San Diego, Salt Lake City, and Dublin.

Evans says the main challenge of ClickUp’s swift rise has been managing culture. The team is 40 percent remote, but Evans says remote communication can only go so far in building a cultural connection. That’s why the company brings the team together in person multiple times a year and encourages local workers to be in the office twice a week.

Evans’ other culture preserver is using the company’s core values to coach employees. “I think, as the founder, you assume everyone sees the vision,” Evans says. “But the reality is people need to be reinforced with this stuff very frequently.”

Evans says it’s also important for core values to evolve alongside the company.

“You’ve got to be OK with it being dynamic,” he says. For example, one of ClickUp’s early values was “progress over perfection.” As the company scaled and its systems became more robust, the value was adapted to “progress toward perfection.”

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Tech Startup Tips From Zeb Evans of ClickUp

• Choose Data Wisely: Be careful with the database structure you choose. Selecting the proper structure can make or break your business down the road.
• Be Fast and Furious: Once you have a strong product idea, don’t wait. Speed is your greatest ally in making a concept into an actual technology business.
• Product > Architecture: Don’t get caught up in making your architecture perfect. Spend your energy making your product as valuable as possible to your target audience.
• Use What’s Available: Cross-platform technologies make building a tech business easier. Don’t build a feature from scratch unless it’s unique to your product offering.
• Recruit for Culture: Hire contractors who fit your culture and encourage them to recruit new talent.