CEO Rapidfire: What Zeb Evans’ 4 Near-Death Experiences Taught Him About Leadership

Welcome to CEO Rapidfire, fast-paced questions with today’s most successful founders and CEOs. Be sure to look for these special Q&A editions of my newsletter, where I’ll share insights from the amazing leaders in my network.

My guest this week is Zeb Evans , the only CEO I know who used to be a monorail driver at Disney World.?

Zeb now leads ClickUp , the all-in-one productivity platform he co-founded in 2017. ClickUp aims to save people time by making the world more productive. The cloud-based platform lets teams brainstorm, plan and collaborate .

With some 10 million users across 2 million teams, ClickUp was named one of Fast Company’s Most Innovative Companies for 2024. Last year, it released more than 100 AI tools to boost efficiency at work. As of 2023, ClickUp had raised almost $540 million from investors including Andreessen Horowitz and Tiger Global.?

Zeb, who calls himself a product-obsessed founder, has found a way to balance that passion with his other duties as CEO. “There’s an element of deep work that has to happen,” he says . To that end, he has a rule: All meetings before noon. “Then my afternoon is more catching up, doing the CEO job,” Zeb explains. “And then the evenings become deep product work, where it’s less distraction, much more mindful.”

Known for his colorful shirts , Zeb has had four near-death experiences , including a boating accident and a home invasion. “I’ve learned a lot about living by almost dying,” he says. His takeaway: “Figure out where you want to go, set goals for yourself, and build towards what fulfills your passions. Life is too short, and time is too precious, to be wasted.”

Here’s what Zeb shared in our CEO Rapidfire interview:

The one secret to succeeding as an entrepreneur, in 5 words or less: Work hard; iterate with urgency.

What was the most exciting “minute” of your entrepreneurial journey? Early on, there was a time when we only had one month of money left to continue operating. (We were bootstrapped at the time.) We ran a promotion, something like 30% off, to upgrade to a paid plan, and we sent it to all of our users, and it worked! We were cashflow-positive, and we had enough money to continue building ClickUp. Seeing users actually pay for the product was that aha moment for us—people paying is the true meaning of value.?

One truth you wish you knew about entrepreneurship before starting? Everyone is just figuring it out. Even the biggest-name entrepreneurs are just figuring it out as they go. Experience is overrated in most scenarios; intuition matters supremely.?

If you had to do battle with a giant, what weapon would you use? Iteration. When you’re smaller, you can iterate faster. Iterate as fast as humanly possible, faster than any giant you battle.?

Your worst mistake as an entrepreneur (and what you learned from it): Hiring super experienced leaders from big companies to take on huge orgs. Instead, look to develop and promote from within, based on merit. Find hungry people who aren’t yet proven, and give them opportunities to grow fast.?

Top 3 websites, blogs, or podcasts you can’t imagine your day without: Tony Robbins , Michael Singer , and the All-In Podcast .?

What popular entrepreneurial advice do you disagree with?

1. ? Hire adults with experience. This is commonly advised to startups: bring in the adults. I think some adults are necessary, but they shouldn't be too far away from a startup. Be careful with big-company adults.?

2. ? Do one thing and do it well. I hate this one. This applies to the product you build but also to strategies.?

3. ? Go enterprise, it’s a better business. If you build for enterprise from day zero, of course, go enterprise. Otherwise, do it iteratively. Over-rotating to “go enterprise” can lead to disaster and to building for a specific customer.?

One life hack you can’t live without: A morning routine that blends physical practices (exercise, cold plunge) with mental practices (journaling). Do not pick up your phone or computer until completing this.?

One soft skill that you’ve realized is supremely important: Optimistic problem-solving. Every business is going to encounter problems, and there’s a night-and-day difference in working to solve those problems alongside someone who’s an optimistic problem solver (i.e., believes there’s always a solution to be found for every problem) vs. someone who has a more pessimistic/negative approach to problems (i.e., over-focuses on the problem and what caused it, instead of being solution-oriented).?

The one thing that makes a good leader great is: Being in the details. Leaders who are figureheads or middlemen are useless. Every leader must be in the details of their org and know every single thing that's going on.??

Your secret to building a great team is: Hire for culture and trust your gut when someone doesn’t feel like a good culture fit but checks off every other box.?

The key to navigating hypergrowth is: The right team that can iterate with urgency, and always does what’s best for the company. This also means avoiding hiring a bunch of people, especially from the outside. When your company is going through hypergrowth, be careful to avoid the trap of hiring at hypergrowth. Hiring fast will only create more problems.?

Every entrepreneur must read… Conscious Capitalism: Liberating the Heroic Spirit of Business by John Mackey and Raj Sisodia, and The Surrender Experiment: My Journey Into Life’s Perfection by Michael Singer.

What are you most excited about at work right now? Internal AI advancements (support, product, engineering, sales) as well as external (product-facing) ones. We’re seeing huge leverage from developing AI internally.??

Your one “non-negotiable” in business (or life) is… Never become complacent. Complacency blocks innovation 100% of the time. The moment you get complacent with anything in your life, whether it’s related to work or personal, you block your brain from being able to discover something better and more innovative. I don't think this means you need to always be “unsatisfied” with the present. You can definitely be happy and satisfied, but also, always be asking yourself, “How can this be even 1% better?”?

Thank you, Zeb, for sharing your leadership thoughts this week. To learn more, follow Zeb on LinkedIn .??

Thank you for reading! I'm interested in hearing your thoughts in the comments below. For more insights from my experience as a serial entrepreneur and how we can harness the power of software to change the world, be sure to subscribe to Entrepreneurship and Leadership.