Unicorn Builders How ClickUp survived the 2021 growth at all costs era and came out stronger ($300M ARR)
Oct 31, 2025
43:25
ClickUp is redefining workplace productivity by converging multiple software categories into one flexible platform. With over $400 million raised and a valuation exceeding $4 billion, ClickUp has grown from a bootstrapped internal tool to serving millions of users globally. In this episode of Unicorn Builders, I sat down with Zeb Evans, Founder & CEO of ClickUp, to explore the company's unconventional journey from ignoring Silicon Valley's conventional wisdom to building one of the fastest-growing productivity platforms in the world.
Topics Discussed:
- ClickUp's origin as an internal productivity tool solving tool fragmentation
- The decision to ignore venture capital advice about niching down and avoiding competitive markets
- Building natural product-market fit through bootstrapping versus artificial growth through funding
- The intense fundraising period of 2020-2021 that raised over $500 million in 18 months
- The cultural challenges of hypergrowth and the return to "founder mode"
- Transitioning from growth-at-all-costs to profitable, efficient operations
- ClickUp's unique approach to performance marketing by hiring consumer-focused talent
- The strategic decision to build headquarters in San Diego versus Silicon Valley
- AI integration strategy focused on human productivity enhancement rather than replacement
GTM Lessons For B2B Founders:
- Build for your own pain, but pivot quickly to market needs: Zeb emphasized that ClickUp started as an internal tool to solve their team's productivity fragmentation across 15 different tools. However, the key was recognizing within weeks that this was a broader market opportunity. B2B founders should solve their own problems first, but be ready to quickly assess whether their solution has wider market appeal and pivot accordingly.
- Ignore conventional wisdom when you have conviction: Despite universal advice to "niche down" and avoid competitive markets, ClickUp deliberately built flexible software for teams of "two or more people" across all verticals. Zeb noted that everyone said "do not go into this category, this is so stupid," but their conviction about building flexible, customizable software that molds to how teams work proved correct. B2B founders should listen to advice but trust their instincts when they have deep conviction about their approach.
- Bootstrap to natural product-market fit before raising: ClickUp remained profitable and bootstrapped until reaching $10 million ARR, which Zeb calls "natural product market fit rather than artificial product market fit." This approach forced them to build a truly valuable product without using dollars to mask product deficiencies. B2B founders should consider bootstrapping as long as possible to ensure genuine market demand before accelerating with external capital.
- Hire performance marketers from consumer, not B2B: One of ClickUp's most counterintuitive moves was hiring their head of performance acquisition from the consumer side. Zeb explained, "the only people that figure out performance marketing at scale is in the consumer side... you can't even name them on a full hand if people had to figure it out on the B2B side." B2B founders should look beyond traditional B2B backgrounds when building growth teams, especially for performance marketing roles.
- Focus on existing engaged users over new logo acquisition: ClickUp discovered that chasing big company signups was less effective than building relationships with users who were already actively using and paying for the product. Zeb noted, "it was really more about looking at the users that are already active users... go build relationships with those people. And then that's your foot in the door." B2B founders should prioritize expanding relationships with engaged users rather than constantly chasing new prospects.
- Culture preservation requires intentional hiring alignment: During hypergrowth, ClickUp hired leaders with impressive backgrounds who weren't culturally aligned, leading to significant culture erosion. Zeb learned that "people just don't change" and that mixing people with fundamentally different work philosophies destroys culture. B2B founders must be explicit about cultural expectations during hiring and prioritize cultural fit over impressive resumes, especially during rapid scaling phases.
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