From 100 rejections to a $42Bn business

It’s hard not to admire Canva as a business and Cliff Obrecht, Cameron Adams and of course Melanie Perkins as founders. They’re an absolute success story, and a blueprint of what’s possible with the right market, right product and the right team.

And of course, vision, determination and 💩 ton of grit.

Melanie made a very rare podcast appearance recently in an episode of Lenny’s podcast, if you’re remotely interested in Product, you’re probably already subscribed; if not, you will be soon. Melanie spoke about the origins of Canva and how the business came to be.

There were multiple lessons that pretty much any business can learn from. Hopefully, you’ll find something in them that inspires you or your team.

If you’re of a Product inclination, you should also check out Lenny’s Newsletter


The founders got rejected by over 100 investors when they started Canva. Today, the company is worth $42 billion, generates $3.3 billion in annual revenue, and has been profitable for 8 consecutive years. The single biggest factor in Canva’s success, according to her, wasn’t execution or product-market fit or hiring.

It was something she calls “Column B thinking,” and most of us have never heard of it.


The problem with stacking bricks.

Melanie says that most founders plan their companies backwards. They look at what they’ve got right now, their skills, their budget, their network, and they ask, “What can I build with this?” It’s sensible. It’s also limiting.

Melanie describes how there are two ways to plan a company.

Column A thinking is what most founders do. You look at the resources around you and ask, “What can I build with these bricks? How high can I stack them?” It’s pragmatic, it’s safe, and it keeps you small.

Column B thinking works backwards from an impossible future. You start by imagining the world you actually want to exist in, not the one you can feasibly create today. For Canva, that meant envisioning a future where design was collaborative, online, and accessible to everyone, not just the 1% with Adobe Creative Suite skills and unlimited time.

When Melanie was a university student with no company, no product, and zero software experience, Column A would have produced exactly nothing. She had no bricks to stack. But Column B gave her something more valuable: a north star worth spending a decade chasing.

The trick seems to be pairing that impossible vision with microscopic first steps. You need “a ladder that goes all the way up to the moon” with rungs that work step by step. The first step might be embarrassingly small, literally just writing down the idea. Then you create a pitch deck.

Then some rough designs.

Each tiny step adds clarity.

She describes the gap between your moonshot vision and that first microscopic step as feeling humiliating. You’re essentially saying, “I want to revolutionise an entire industry”, while your first action is opening a Google Doc.

Most people either skip the big vision (too intimidating) or skip the small steps (too boring). Melanie says that having both is important.

How to start: Set aside an hour this week to write down your Column B. What would wild success look like in 10 years? What would a terrible failure look like? Don’t think about feasibility. Don’t think about your current constraints. Just imagine the future you actually want. Then ask yourself: What’s the smallest, most embarrassing first step I could take toward that future this week?


Every bold idea starts ugly

Every bold idea starts as what Pixar calls an “ugly baby,” fragile and unformed.

Canva has a framework for this: “Chaos to Clarity.” Every project, every feature, every new initiative starts on the chaos side. It might be an idea, a problem, or just a vague philosophy. Your job is to systematically move it to the clarity side through incremental steps.

The first step at the far end of chaos? Melanie admits it’s “quite embarrassing” because you don’t have mastery yet. You don’t have answers. You just have a belief that something could be cool. But you externalise it anyway.

For Canva, this means creating vision decks for every significant project. Not strategy documents. Not PRDs. Vision decks that articulate what wild success looks like for this specific initiative. It forces you to clarify your thinking, and it lets other people see inside your head. Visual communication turns abstract chaos into something concrete that others can react to, critique, and help build.

The process compounds. Melanie looked back at a 2021 vision deck (made in 2021, about what 2026 would look like) and found that most of those “crazy” predictions had actually come true, just not on the timeline they expected. Things they thought would take six months took two years. But they still happened because the vision was clear and persistent.

This isn’t about being precious with ideas. It’s about giving them structure so they can survive contact with reality. Canva spent two years rewriting its entire codebase, work they thought would take six months. They couldn’t ship any new features during that time. It was necessary for everything they wanted to build (cross-platform support, right-to-left languages, massive collaboration), but it was brutal. They made it into a game with rubber ducky markers on a progress board to keep morale up. That’s chaos to clarity in the hardest mode: when the tunnel is so dark you can barely see the end.

How to start: For your next project or initiative, resist the urge to jump straight to execution. Create a one-page vision document first. Write down: (1) What problem exists today, (2) What the future looks like if you solve it perfectly, (3) What the very first step is, no matter how small. Share it with three people. Use their confusion as data to add clarity.


Turn rejection into free product development

Over 100 investors said no to Canva. That’s not hyperbole; Melanie pitched over a hundred investors before getting a yes.

What’s interesting is that she didn’t think the investors were right. She thought they were wrong. But she listened anyway because rejection came with feedback she could actually use.

An investor would say, “Your market’s not big enough.” Instead of getting defensive, she’d add a slide to her pitch deck showing the market size. Another would say, “You’re the same as this other company.” She’d create a competitive landscape slide showing exactly where Canva fit in the gap others weren’t filling. Another would point out that they didn’t understand design or the industry. She’d add context slides explaining the problem landscape.

Each rejection made the pitch deck stronger. By the time she found investors who were willing to spend hours understanding the vision, she had a deck that could communicate it in minutes. When she looks back at her 2012 pitch deck now, it’s “so valid and really still captures what we’re doing today.” That’s because it was stress tested through a hundred failures.

This applies beyond fundraising.

Canva receives over 1 million feature requests from users every year.

They don’t ignore them; they have a team that tallies and categorises them, then closes the loop by actually building what people ask for. This year alone, they’ve “closed” over 200 loops. Some were small (gradient text). Some were huge (their entire spreadsheet product). Their education product wasn’t released to teachers initially because they anticipated hesitancy around AI in classrooms. Teachers flooded them with requests to access the AI features anyway, so Canva added safety controls and opened it up.

The pattern: Use negative feedback (rejection, criticism, feature requests) as free product development. Every “no” is someone telling you what’s missing from your story or your solution. Most founders either ignore feedback (too painful) or get paralysed by it (too overwhelming). Canva systematises it: collect it, categorise it, integrate what makes sense, iterate.

How to start: If you’re fundraising or selling, track every objection you hear in a simple spreadsheet. After 10 conversations, look for patterns. What’s the most common objection? Add a section to your pitch that pre-emptively addresses it. If you have a product, identify your three most common user complaints this month. Pick one and ship a fix next week. Close the loop.


What this actually means

The through line in all of this is ambition plus systematisation.

Most companies have one or the other. They have a big vision but no process to get there (they stay stuck in inspiration mode). Or they have great execution processes but no compelling destination (they build incrementally to nowhere in particular).

Canva’s approach is doing both simultaneously. The mission, “empower the world to design,” breaks down into specific pillars (design anything, in every language, on every device, with every ingredient). Those pillars break into yearly goals. Those goals get celebrated when achieved (they’ve literally smashed Greek plates and released doves). The “crazy big goals” create motivation because they make you “feel completely inadequate before them,” which makes you work harder.

But their timing is terrible. They consistently miss their own deadlines. Six-month projects take two years. Some goals take their “entire lifetime” and might never be achieved. And that’s fine, because the vision is clear enough and compelling enough that being late doesn’t matter, forward progress does.

This requires unusual confidence. You have to believe your impossible vision is correct even when everyone with money tells you you’re wrong. You have to be comfortable looking foolish as you take embarrassingly small first steps toward something massive. You have to systematise feedback loops without losing sight of where you’re going.


This week, try this:

  1. Create your Column B document. Block one hour. Write down what wild success looks like for your company in 10 years. Be specific, not generic. Don’t write “be a unicorn,” write what problem you’ve solved and for whom. Then write what terrible failure looks like. The contrast will clarify what actually matters to you. Pin it somewhere visible.
  2. Start a rejection/feedback log. Whether it’s investor conversations, sales calls, or user feedback, create a simple document where you record objections and complaints. Review it weekly. After 10 entries, look for the pattern. What’s the most common concern? Make addressing that your top priority for the next sprint.
  3. Launch your own “chaos to clarity” process. For your most important current initiative, create a one-page vision doc before you write any more code or strategy documents. Include: the problem, the perfect future state, and the first concrete step. Share it with your team. Use their questions to add clarity. Treat it as a living document, not a one-time exercise.

The competitive landscape is shifting. AI is making execution cheaper and faster for everyone. Soon, coding ability won’t be the bottleneck; imagination will be. The companies that win won’t be the ones with the best engineers or the most funding. They’ll be the ones who can envision a genuinely different future and build systematic pathways to get there.

Column B thinking isn’t about being unrealistic. It’s about being honest about what actually drives enduring value: a clear, compelling destination that makes the brutal middle miles worth it.

Watch Melanie on the Lenny’s Podcast for yourself.


Before you go, can you help me out?

Nearly 1300 people have now subscribed to this newsletter in ~15 weeks, which makes me feel that it’s resonating. So thank you to all of you 🙏🏻

If you found this issue useful, here are three ways you could support me:

  • Share it – Forward this to a founder, hiring manager, or job seeker who you think might find it useful and/or interesting.
  • Follow StartUpHiring on LinkedIn if you’re not already – https://www.linkedin.com/company/startuphiringaustralia
  • Send feedback – What topics would help you most? What’s working? What isn’t? Just hit reply.

I’m building this into the go-to resource for startup hiring. Whether you’re hiring your first employee or looking for your next role, I want this to be genuinely useful for you.

These small actions make a massive difference in helping me reach more people who need this content.

Thanks for being here. Have a brilliant week ahead.


Weekly newsletter drop: Wednesday 1:30pm


Need hiring help?

If you’re struggling with a specific hiring challenge, I still offer 1:1 strategy calls through my consultancy, Crew. Book a 15-minute clarity call here.

Simon

Recruiting Trends 2024 Shaping the Future of Tech Talent in Australia
Level Up Your Hiring Game with our Podcast & Newsletter