Jan 27, 2023 · 58m · news
Canva's Cliff Obrecht: How We Turned Our Yearbook Company to $40B Business | 20VC #971 · 20VC with Harry Stebbings
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this in-depth interview with Harry Stebbings, Canva co-founder and COO Cliff Obrecht details the company's journey from a regional Australian yearbook publisher to a $40 billion global design platform, sharing core insights on overcoming extreme fundraising rejections, scaling unique recruitment cultures, and balancing a high-profile business partnership with a healthy personal life.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 17.6% of the talking time here. How this is scored →
Harry as informed peer 2.9 Guest teaching 3.9 Guest disagreement 2.4 Harry pushing back 2.8
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 37:38 Vehement rejection of 'good enough' software
Cliff forcefully rejects Harry's framing that bundled software suite products sacrifice depth for convenience, stating 'we hate good enough, like hate it.'
Hardest push from Harry ▶ 31:35 Direct pushback on non-technical foundersHarry directly challenges Cliff's founding structure, stating that backing two non-technical founders is a primary reason he personally would reject an investment.
Biggest teaching moment ▶ 26:30 Deconstructing Canva's smooth growth narrativeCliff educates Harry on the unseen technical realities behind Canva's upward trajectory, describing a grueling two-year feature freeze to rebuild frontend code.
Harry holds his own ▶ 43:45 Challenging the wealth custodian framingHarry challenges Cliff's view that self-made founders are merely custodians of equity, asserting as a VC that creating value from scratch is fundamentally different from inheriting wealth.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Navigating Silicon Valley and Early Fundraising | 2 | 4 | 1 | 1 | Harry brings up specific context from investor Doug Pepper regarding kite surfing in Maui with Bill Tai. Cliff explains the early fundraising grind and Maui backstory, detailing over 100 VC rejections before securing early backing. | |
| Advice on Rejection and the Power of Integrity | 2 | 3 | 2 | 2 | Harry prompts Cliff on maintaining motivation through rejection and defines business high performance. Cliff shares his long-game philosophy on integrity and banters playfully about physical fitness. | |
| The 'Distance Traveled' Concept in Talent and Hiring | 2 | 5 | 1 | 2 | Harry asks Cliff to unpack the concept of 'distance traveled' in talent hiring. Cliff draws from his experience teaching underprivileged child soldiers to explain why non-traditional backgrounds often yield the strongest performers once they learn the business 'game'. | |
| Hiring Strategy: Homegrown Talent vs. External Executives | 3 | 4 | 2 | 3 | Harry references discussions with Canva's team regarding Cliff's dealmaking strengths and asks how to detect posturing in M&A. Cliff details his transparent deal philosophy and calls out typical corporate development tactics as 'bullshit'. | |
| Building Sales and Marketing: Canva's 'Leg Day' | 2 | 4 | 1 | 2 | Harry asks about investor relations and past acquisition mistakes. Cliff describes Canva's early state using a bodybuilder missing 'leg day' metaphor, explaining how they systematically built up marketing and sales capabilities. | |
| The Darkest Times: Tech Debt, Frontend Rewrite, and Copycats | 2 | 6 | 2 | 2 | Harry notes Canva's smooth public trajectory, prompting Cliff to recount their hardest periods. Cliff details a complete two-year frontend rewrite where feature shipping froze completely despite aggressive copycat competition. | |
| The Non-Technical Founder Risk and Co-Founder Dynamics | 5 | 4 | 2 | 6 | Harry directly challenges Cliff, noting that two non-technical founders is a major red flag for VCs and asking why he shouldn't view it as a dealbreaker. Cliff agrees it was a massive risk, explaining how bringing on Cam Adams mitigated investor concern. | |
| Bundling vs. Unbundling: Canva's Unified Platform Strategy | 6 | 5 | 5 | 6 | Harry argues that bundled software usually yields inferior product quality compared to point solutions. Cliff vehemently rejects the 'good enough' premise, explaining Canva's single engine architecture before Harry challenges Cliff's view that founders are merely custodians of created wealth. | |
| Parenting, Frugality, and Experiential Investment | 3 | 4 | 6 | 3 | Cliff turns the conversation back onto Harry, questioning whether handing kids massive wealth corrupts them and teasing Harry about spoiled behavior. Harry explains his investment in personal trainers and meal prep to optimize operational output. | |
| The Dynamics of Co-Founding with Your Spouse | 2 | 3 | 1 | 2 | Harry asks about co-founding Canva with spouse Melanie Perkins and maintaining boundaries between personal life and business. Cliff candidly discusses the inevitability of work talk creeping into family time and the necessity of shared understanding. | |
| Fatherhood, Routine, and Parenting Advice | 3 | 3 | 2 | 3 | Harry strongly urges Cliff to hire a night nanny for sleep management. Cliff counters that establishing strict routine, guided by a sleep consultant, was what actually solved their infant sleep issues. | |
| Quick Fire: Books, Philosophy, and Dream Board Members | 2 | 2 | 2 | 2 | Harry runs through quick-fire questions on reading habits and personal growth. Cliff humorously admits to naively telling his pregnant wife that having a baby couldn't be that hard. | |
| Bob Iger's Value Philosophy & Evolving as a Leader | 3 | 4 | 4 | 2 | Cliff selects Bob Iger as a dream board member for his focus on core product value over internal corporate fluff. He calls out early Bay Area VCs who dismissed Canva because they couldn't ride a bike to the company's offices. |
Statements from this episode (24)
Canva was rejected by over 100 VCs before securing its first check
“We spent over a year there, like back and forth, still trying to run our other business. And we got rejected over a hundred times by VCs before we finally convinced some people to invest in us”
Obrecht: Treating rejected job candidates with integrity brings them back later
“If you leave a nice taste in those people's mouths, like, and you always be the good human, and be the honest Honorable person and speak truths. People come back, and they remember you, and when they are ready for that career change, or when an opportunity doe…”
Obrecht honors business commitments without term sheets or legal documents
“If I say something and make a commitment to something, then my word is my bond. I don't need a term sheet. I don't need a legal document.”
Canva's Obrecht: Melanie Perkins and I take opposite approaches to building trust
“Mel and I are completely, so Mel is my wife and the CEO of Canva. So my boss which is and definitely the worthy boss. But we have totally opposite ends of the spectrum when it comes to trust. So I trust by default and you can lose that trust. Mel, it takes a l…”
Canva co-founder Cliff Obrecht hated and couldn't use computers before starting up
“I couldn't use computers before we started our first, I hated computers to be honest, before we started our first business.”
Obrecht: Candidates From Obscure, Self-Taught Backgrounds Become Canva's Best Performers
“If you have come from a obscure background, like non-traditional tech or whatever and have taught yourself the tools, I find those people, once they figure out the game, cause this all is just one big game. Once they figure out how to play the game, they are S…”
Early Canva made terrible hiring decisions by deferring to big tech titles
“And I guess that came across and we made a bunch of really, really poor hiring decisions because We just assumed these people were smarter than us, and then like, they're in the company like a year, and we're like, Fucking hell. Like you're not really smart at…”
Canva's Head of People Started as Co-Founder Cliff Obrecht's Executive Assistant
“Our, my EA is now our head of people.”
Canva CMO Zach Kitschke Joined as a 19-Year-Old Contract Content Writer
“Zach, our CMO joined Canva as like Content writer, a contract content writer. He was like, 19 at the time. He's been with the company about 10 years now. He's now a CMO.”
Cliff Obrecht claims Canva has never made a bad company acquisition
“Not really. Not really. Not really. No, I'm saying no.”
Obrecht: Canva still uses generous equity grants to compensate advisors
“Even in the earliest days, we used to pay people with generous equity grants, and we still do to this day to get them on as an advisor.”
Canva had zero formal sales and marketing teams until 2020
“Canva until three years ago, we were like a big bodybuilder that had not done a single leg day in their life. So we had a huge upper body, and that was our user acquisition, that was our product, and that was our organic growth. But our two weak little legs we…”
Obrecht's team manually recreated 100,000 pages in Photoshop after software failed
“So we had to, I think, recreate over a 100,000 pages with like Photoshop and InDesign where we had to hire a team of designers on Upwork yet again. To essentially like eyeball these pages and redesign them in Photoshop and InDesign, and then we had to convert …”
Canva halted new feature releases for two years to fix tech debt
“So we had to down tools and ship no features for a full two years. It was supposed to be one year, but it took two years in the middle of Canva's growth journey, call it from year four to six, about year 10 now.”
Obrecht: Canva succeeded by consolidating a fragmented graphic design ecosystem
“So Canva was created because before Canva, the design ecosystem was incredibly fragmented. You had to go to a stock photo site to get your stock photos. You had to Go to Vistaprint to print your stuff. You had to use three different softwares to create your de…”
Obrecht: AI adds value through workflow integration, not standalone tools
“There's all these cool tools, but it's really how those tools show up in a workflow where people get their job to be done done. That really adds the most value, and that's why we're investing so heavily into AI as really the co-pilot to help people achieve the…”
Canva disrupts enterprise SaaS by charging only for active quarterly seats
“We don't try and sell an organization a thousand seats. We only charge you based on the number of active seats in a particular quarter.”
Obrecht: I do not angel invest to make money
“I actively don't angel invest. I do do some just because it's like a great person that I know, or it's like, I really like, I don't do anything to make money. I do, I back ideas that I think the world needs to see.”
Canva co-founders pledged 99 percent of their equity to charity
“Mel and I, we own 31% of Canva, and we put 30%, so like 99% of what we own in, into a charity that we can't spend on our own stuff”
Billionaire Canva co-founder Cliff Obrecht still flies economy class
“I still fly economy, unless I can get a points upgrade, because I can't, like, I'm like, you want 10 grand for, like, a five-hour trip? I'm like, I'll tough out that 10 grand, and I'll spend that 10 grand on something else.”
Obrecht: Global philanthropy lacks efficient systems connecting capital to world problems
“I think the world has enough good intentions and capital to solve the world's problem. I think what we need to solve and not just us, but the bridge we need to, the gap we need to bridge is connecting those good intentions and that capital with the problems. A…”
Obrecht: Canva co-founder will not build another commercial startup
“Well, I don't think so. It's hard. Although, glance for punishment. Like, we will probably do, we'll run projects, philanthropic projects that are built like a startup based on technology.”
Shorts cut from this episode
▶ This BILLIONAIRE Gave Away 99% of His Money 💸😲 · 20VC with (@41:53)
▶ Why this BILLIONAIRE is giving away $3B 😲🤑 · 20VC with Har (@44:12)
▶ Australian's Coolest Billionaire 🍷💰 #shorts · 20VC with Ha (@40:10)
▶ Billionaire's Imposter Syndrome #shorts · 20VC with Harry St (@15:31)
▶ How Canva founders raised money for Billion $$$ business 😲� (@0:00)