Canva's Cliff Obrecht: How We Turned Our Yearbook Company to $40B Business | 20VC #971

Canva began by solving a very specific problem—school yearbooks—before generalizing the same core concept to broader visual communication. Obrecht frames this as “start niche and go wide,” solving one group’s pain deeply, then moving to adjacent segments.

Obrecht and Perkins were rejected by over 100 VCs, yet persisted while running Fusion Books and couch-surfing in the US. He stresses that playing the “marathon, not a sprint,” combined with always keeping your word, eventually draws talent, partners, and investors back to you.

He looks for candidates who’ve overcome significant disadvantages or non-traditional paths, arguing that once they “figure out the game,” they can outperform stereotypically polished résumés. Many of Canva’s top leaders (e.g., CMO, Head of People) were promoted from junior or unconventional roles.

Obrecht’s deal-making approach is to quickly surface whether an acquisition or partnership can align both sides’ goals, be clear about what is valuable and what is not, and avoid drawn-out, vague corp-dev courtship. He prefers a fast no to a slow no and emphasizes character and founder motivation.

Canva halted feature shipping for nearly two years to rewrite its front-end and repay crippling tech debt. In the short term this was a “death march,” but it enabled far greater product velocity and defensibility later, illustrating the payoff of painful, foundational work.