Meet the Entrepreneur Whose Thirst For Life Has Brought Him to It’s Edge

The first time Zeb Evans nearly died, he was 10.

He was Jet-Skiing with his family near a friend’s lakeside home in North Carolina, when he went to dock the craft and came in too fast. Young Zeb hit the dock and flew off the Jet Ski and somersaulted in the air, landing on the side of his stomach on an adjacent dock’s hard metal ramp. The impact sliced open his obliques, and Evans blacked out. His parents rushed him to a nearby hospital, where doctors stitched him up and kept him for observation. On his second night in the hospital, “I had crazy pain,” Evans says today, “like a knife going through my whole body.” The doctors thought the pain stemmed from the newly formed scar tissue on his abdomen. Then he started vomiting. He couldn’t eat anything. Within days, Evans couldn’t summon the strength to walk.

By the time a pediatric specialist realized Evans was suffering not just from the stomach injury but also a ruptured appendix, which was draining pus into his body and blood, his condition had deteriorated so much that doctors feared he would die if they waited even a day to operate. After the appendectomy, the doctors refused to sew Evans back up. The poison pus had to seep out first, through his exposed gut.

For two months, he lived with two tubes stuffed into his midsection. Every few hours, nurses would rip the gauze from his sticky wound, clean the site with alcohol, and press a new layer of gauze down. The pain of that, the indignity of the catheter, the unceasing hunger from his inability to eat–he couldn’t help but feel angry, couldn’t help wallowing in self-pity. But he also learned something he’d never forget about the fragility of life, how even a healthy 10-year-old kid could nearly die and then take two months to struggle to live again.

It was a precocious notion for a 10-year-old, but Evans decided something around the time of his release from the hospital: He decided that he would not waste this life. He would live it on his terms. We know this because before he went home he began to write notes to himself, a form of journaling. His father, Chuck, saw one entry:

I want to have a successful, big company that’s as big as McDonald’s.

Today, Evans is 33 years old and the founder and CEO of San Diego-based ClickUp, a maker of productivity software. The company currently employs nearly 1,000 people and has raised $535 million in venture capital, valuing the firm at $4 billion.

Those might not be McDonald’s numbers, but they are undeniably big numbers. Evans has achieved a lot. Still, to him, the number that matters most is a smaller number: three. Because that’s the number of times he has nearly died. And Evans–like many others with similar experiences–would tell you that what happened the three times he almost died gave him something more valuable than the billions his company is worth.

In fact, he’ll tell you his company is worth those billions because of them.

He had always been entrepreneurial. Even before the ruptured appendix, Evans had set up his own account with the Oriental Trading Company, a direct-marketing retailer, and then sold its party supplies to neighborhood kids and parents. He would even roll out a selection of products one week while teasing the release of new ones the next. This floored his parents, both doctors, who hadn’t encouraged his business thinking at all, let alone helped him devise strategies for creating demand with staggered release dates.

“He came out like this,” his mother, Lisa, says all these years later. Unlike his two younger brothers, who wanted toys for Christmas, Evans would ask for a checkbook or a functional cash register. And in the years after his hospital stay, he let his curiosities drive his life all the more–because why, after all, live any other way?

He got into DJing in high school and sweet-talked his way into an on-air spot in the evenings on 102 JAMZ, the only hip-hop station in Greensboro. He named himself DJ Curfew, because his sets would sometimes abruptly end on school nights when he had to get home to bed.

But he was good. The public wanted more DJ Curfew–so Evans set up a mobile DJ company called Curfew Entertainment. He did Sweet 16 parties and corporate events. Shortly after enrolling at Virginia Tech in 2008, he moved into producing the songs of Blacksburg acts and ultimately managing the artists. He did all of this while carrying a full load of business courses, even though he was always more interested in creating companies than in discussing them in stale auditoriums.

“There was never a time in which he wasn’t trying to be an entrepreneur,” says a friend from those years, Chris Cunningham, the self-described “hype man” for Curfew Entertainment. One of Curfew’s acts was Killa J, a Blacksburg rapper who started getting wider attention after Evans began promoting him. Eventually, agents for two major national acts, Wiz Khalifa and Macklemore, contacted Curfew Entertainment wanting to know if Killa J could tour.

It was the kind of opportunity no self­­-respecting entrepreneur could pass up, and yet none of the Curfew guys were ready to bail on college altogether–so Evans devised a solution: Nascent online classes were limited and, besides, filled up almost instantly. So Evans created a bot that signed them all up for every online course they needed before the classes had time to fill up.

Which is how they came to spend that semester traveling up and down the East Coast, attending classes online. And they could see it, success in the music business unfolding before them: Killa J as a national act, Cunningham as manager, and Evans as the music mogul, running it all, expanding it all.

Others could see it too–including a young rapper named Davonte Mason, who went by Lil Fresh and whose promoter told Cunningham he wanted to meet Evans and maybe sign up as a client.

One day in 2011, Mason drove to Evans’s apartment from Petersburg, a suburb of Richmond, and brought along two friends who didn’t identify themselves. Evans brought the three of them upstairs to his room so they could listen to Mason’s CD together, and as everyone settled in, one of Mason’s friends excused himself to go to the bathroom. When he came back, he pointed a gun at Evans.

“Give me your money,” he said.

Evans thought he was joking.

After the three young men marched Evans and his roommate into a closet and put them on their knees–the man with the gun placing the barrel against Evans’s forehead–they began robbing the place. They didn’t find much. What money Curfew had was tied up in rent and studio and production expenses. Evans told them as much, and for that the gunman said he was going to kill them. Then he laughed.

I’m going to die, Evans thought. This is it.

He thought about a lot in that moment there in the closet. He thought about how much time he’d lost to the party scene that accompanied the music scene, that so often was the music scene. What did it contribute to his life? To anyone’s? The same went for college. He’d sat through too many pointless lectures and wasted these years. He’d started Curfew Entertainment, sure, but he wanted to create something that impacted the world.

He vowed in that closet that if he some­­how survived this robbery he would drop out of school. He would focus solely on creating a new business. A new life.

There is a clarity of purpose that comes to many founders who have near-death experiences. The examples are legion: Steve Jobs outlasted the pancreatic cancer that was supposed to kill him within six months and then told Stanford students in a commencement address two years later, “Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life.” The founder of the emoji app, Chad Mureta, credits his success to a near-fatal car crash that hospitalized him for six months, during which, he’s said, “I was sitting there, on all these IV drips, morphine, and I looked around and I finally saw the picture. I entertained a different destiny.”

There are others less famous, but no less profound. Melinda Richter, at age 26, was traveling the world for a telecom firm when a bug bite led to meningitis and a prognosis that she would very likely die. Going to bed each night wondering if she might not wake up led Richter, after she’d beaten meningitis, to ditch her job, secure an MBA, and launch an incubator in 2004 that ultimately begat the R&D venture called JLabs, which has today fostered more than 640 collaborations.

Jules Schroeder suffered a wakeboarding accident in 2015 that put her in the hospital, in and out of consciousness, during which she received a vision that inspired her to lay the groundwork for her podcast for entrepreneurs, Unconventional Life. As she said then: “Something happened to me in that hospital room that I can’t explain. Who I was before and who I am now are different. The things that used to matter now don’t.”

Tim Loney, founder of Houston-based IT-service company Solutions Information Systems, was resuscitated three times from what he described as a “widow-maker” heart attack in 2018, and then adopted what he calls a “new approach” that totally altered his entrepreneurial journey: “I’d put up with a lot of stuff I shouldn’t have,” he says today. Clients who demanded too much. Employees who didn’t show up on time. Not any longer. Loney says he speaks his mind now because time is limited. Tomorrow is not promised. His newfound honesty is not only edifying, but also profitable. “A consistent progression” in revenue, he says.

None of which surprises Bruce Greyson, an emeritus professor of psychiatry at the University of Virginia who has studied near­-death experiences for 50 years. “There is one thing about which I am certain, about which the evidence is overwhelming–and that is the effect of NDEs on people’s attitudes, beliefs, and values. … [These people] often talk about death as a gateway to another kind of life,” he writes in his book, After: A Doctor Explores What Near-Death Experiences Reveal About Life and Beyond. As he says: “The answers to questions that are so opaque in daily life are crystal clear in the NDE, because the answers are so simple.”

In one way or another, facing death is terrifying–and then clarifying.

And so it was for Evans, for the second time. On that day in 2011, the robbers upturned everything in his apartment. Then they left–they just walked out. And though it took several minutes for Evans and his roommate to muster the courage to move out of the closet, the first thing they did was notify the police.

The next thing Evans did was drop out of Virginia Tech.

If the burst appendix had taught him about the fragility of his own life, surviving the armed robbery had infused him with a passion to do something more meaningful. How to do that, though, was very much an open question.

Social media was still a relatively new phenomenon in 2011, and Evans had gotten Killa J to appear on a national tour partly through the deftness with which he’d managed the rapper’s social accounts. He’d built Killa J’s audience by first following other hip-hop acts and talking about them in posts, which would compel those acts to follow Killa J back. That was standard practice already at the time, but then he built a bot to automate the process. Now, as he considered his future, he wondered: Could he scale these “hacky” automations into a real business and help everyday people capitalize on social media? He started a company called Fast Followerz to find out.

Evans didn’t know how to code, but he owns two qualities: a founder’s predis­position to action and a polymath’s intellect. So he parked himself every day in a local Starbucks and studied up on websites such as Treehouse. He stayed in that Starbucks for hours, learning, obsessing, at times until it closed at night.

In truth, he didn’t have anywhere else to be. Evans is preternaturally calm and tends to speak in an even manner. But in the weeks following the robbery, still jumpy from it, he refused to go back to his apartment, and was sleeping on the couches of the few friends he trusted. He didn’t talk about what happened, even with them. “Zeb keeps to himself a lot,” Cunningham says. Some nights, if no couch was open, Evans slept in his car. He eventually got his own apartment outside Blacksburg, but found himself constantly peeking out from the shutters.

He hadn’t sought therapy for the PTSD from which he was likely suffering. He didn’t know he should. So Fast Followerz became his therapy. He buried himself in work, attempting to perfect the app’s automation, a proprietary formula based on the follow-first method. Social media influencers were on the rise, and Fast Followerz could help them build followings in whatever industry they aimed to, well, influence. His bots would direct an influencer’s accounts to follow specific users in the target audience; many would follow back. From there, the influencer could sell products or services or just get famous enough that social media platforms themselves would strike up advertising deals with them.

It began to work well. One day, Cunningham visited the apartment outside Blacksburg and found his friend in front of eight computer monitors in a darkened room. Evans could hardly stop to chat, because the phone kept ringing with calls from customers.

Within a few years, by 2015, Fast Followerz had some 25 employees and thousands of clients. The influencers loved the personalized dashboard– revolutionary for the time–which tracked who their followers were and projected future growth of the influencer’s brand. Such ingenuity helped grow the company’s revenue to $2.5 million a year by 2015. Evans had quieted his anxiety and depression through action. He had moved the company to Charlotte, picked up a heavy running habit, adopted a vegetarian diet, and started journaling every day, hoping to understand himself.

But in those journal entries, he also began to write about a twinge, a lingering unhappiness. Customers wanted their follower counts to grow faster. He wanted to serve them better, build a new CRM system, expand his customer base, grow his company, grow his wealth.

“I want to do something more, think bigger,” he wrote in his journal.

One night he was persuaded by some friends to take a break to see The Martian, the Matt Damon sci-fi flick. Evans didn’t want to go; he was “on edge,” he says, from the thousand stresses of being a founder. Everyone sat in their seats in the theater while Evans obsessed over his “vocal” and “needy” customers, the endless ruminating leading to still more: the toxicity of social media and the sickness, too, of American culture, because it was not so long ago that someone had gone into a movie theater much like this one, in Aurora, Colorado, and shot up the place, and what would happen …

Evans slumped in his chair and flopped to the floor.

The next thing he could register was people staring at him, carrying him outside, a woman telling him to try to breathe. She’d had grand mal seizures, too. A seizure?

The story came to him. He had fallen from his seat minutes into the movie and had shaken violently on the floor.

Later, at a nearby hospital, doctors began a battery of tests that took several weeks. They ruled out epilepsy, and then a brain tumor, before one neuro­logical specialist suggested Evans had a condition called convulsive syncope, which causes one to lose consciousness and perhaps shake violently, and can lead to sudden cardiac death. Such a violent reaction was often caused by stress.

Doctors asked: Was Evans overly stressed? He scoffed yes. Later, a voice in his head posed a follow-up: Did he actually enjoy his life?

After the robbery, Evans had wanted to make an impact. Now he feared he had instead only helped people who were obsessed with their own egos. “Was I actually helping the world?” he wondered. “Was anything we were doing net-positive?”

So he quit. Didn’t sell Fast Followerz to anyone. Just up and dissolved the company.

He was in his mid-20s, a millionaire college dropout who had endured in that theater a third near-death experience, and was furiously seeking clarity on what it could teach him about the life still ahead of him.

The world was full of big problems. Could he solve one of them? Could that be his impact? He journaled his way to what he thought was his answer: The internet had too many liars and hucksters and fake filters that obscured reality. Evans decided to develop a tool that would clean up the scammy corners of online marketplaces such as Craigslist.

He began in 2016 to work on a social media platform that he would ultimately call Mimri. As Zeb imagined it, there would be no “liking”; there would be walled gardens of digital intimacy where you and your friends would talk about images from your past that you shared on Mimri. Chris Cunningham joined him again, along with a few people from the Fast Followerz team and an engineer from IBM named Alex Yurkowski, who agreed to come on as co-founder and CTO. They moved the venture to Silicon Valley, found a house they could live in and work out of, and set to work.

The first thing to get right was their own productivity. At Fast Followerz, they’d used at least 10 productivity applications, Evans says: Asana, Trello, Slack, and on and on. None of them made the team more productive. All of them gave the team more stuff to track and, therefore, added hours to their workdays. Yurkowski decided to build an in-house app to do the work of 15 other productivity tools all in one–and, lo and behold, it worked. So well, in fact, that friends and neighbors in the Valley started asking if they could use it too. It became a recurring joke, and then a refrain, and then it became the business, as Evans realized he had to pivot the company from Mimri to this productivity application.

There is a boring way to talk about ClickUp and a philosophical way. The boring way is to say the application makes companies’ workflows and processes more efficient. The philosophical way is to say the hours that companies don’t spend in soul-sucking project- management meetings are ones employees can spend away from work.

Spending time well had become Evans’s mission by 2017, the outcome of the clarity he’d gained from his third near-death experience. For him, work was no longer life. Life was the totality of your days. If this, these hours and days and years, are fleeting, then how do I persuade others to make the most of the precious time they have? he wondered. The answer: by returning time to them.

Until ClickUp entered the space, productivity applications had been, to Evans, “opinionated,” with “so many guardrails on how you should work.” As the writer Annie Dillard wrote: “How we spend our days is, of course, how we spend our lives.” And so ClickUp would refuse to pass judgment on how its users worked each day. It would be an all-in-one application in which people could add features they wanted, subtract ones they didn’t. It would work for solo­preneurs, mom-and-pop shops, multi­national corporations. It would fit the lives of its users, not rule them.

The growth that ensued came largely by word of mouth, leads arriving with such consistency that for three years, ClickUp had neither a marketing nor an advertising budget. Still, by the spring of 2020, the company had amassed 100,000 customers, including Nike and Netflix. To date, more than six million users across 800,000 teams use ClickUp’s services, and ClickUp itself employs almost 1,000 people across the world, with a base in San Diego and its own teams using the software to manage their many-time-zoned lives. Revenue hit $85 million in 2021, and is on track, Evans says, to reach $200 million this year.

And all that money, in its way, is the final lesson of Zeb Evans’s many brushes with death.

He would tell any entrepreneur that it takes courage to align your personal values with your professional ones, but when you do, when you “live and breathe it,” your values themselves become valuable, even profitable. Your values become the differentiation point between what you sell and what everyone else does.