Nov 2, 2025 · 1h 6m · lennys-podcast
She turned 100+ rejections into a $42B company | Melanie Perkins
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
Canva CEO Melanie Perkins joins Lenny Rachitsky to discuss how she navigated over 100 investor rejections to build a profitable $42 billion visual communication platform. She shares actionable frameworks on 'Column B' visionary planning, authentic organizational culture, community-driven product expansion, and Canva's mission-driven 'two-step plan' for global philanthropy.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Lenny holds 28% of the talking time here. How this is scored →
Lenny as informed peer 4.4 Guest teaching 5.6 Guest disagreement 1.0 Lenny pushing back 1.1
speaking balance: gold is Lenny, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 27:06 Melanie dismisses early investor skepticism
Melanie frankly states that early investors rejecting Canva were simply wrong about the future of design and market size.
Hardest push from Lenny ▶ 18:51 Lenny challenges the risk of missing audacious targetsLenny pushes back on how to set extreme goals without burning out or demoralizing teams when delivery dates continually slip.
Biggest teaching moment ▶ 27:30 Reframing investor rejections into deck iterationMelanie educates Lenny on how she systematically weaponized over 100 investor rejections to pre-emptively answer every objection in her deck.
Lenny holds their own ▶ 6:37 Lenny synthesizes Column B with Airbnb's product designLenny demonstrates deep product expertise by linking Melanie's abstract framework directly to Brian Chesky's reverse-engineering methodology at Airbnb.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Lenny as informed peer | Guest teaching | Guest disagreement | Lenny pushing back | Why |
|---|---|---|---|---|---|---|
| The Core Philosophy of Column A vs. Column B Thinking | 6 | 5 | 1 | 1 | Lenny connects Melanie's Column B philosophy directly to Brian Chesky's backwards-planning product framework at Airbnb. Melanie articulates how traditional planning gets trapped stacking existing bricks instead of imagining an improbable ideal future. | |
| Framework for Building a Column B Company | 5 | 6 | 1 | 2 | Lenny challenges the premise by asking why most founders fail to think big enough when they believe they already have a vision. Melanie explains that founders get paralyzed by the awkward gap between a vast 10-year moonshot and microscopic daily tasks. | |
| From Chaos to Clarity: Operationalizing Vision Through Decks | 6 | 5 | 1 | 1 | Lenny references Ed Catmull's 'ugly baby' concept from Creativity Inc. to frame the vulnerability of early-stage ideas. Melanie expands on this by explaining how pitch decks operationalize chaos into clarity. | |
| Embracing Crazy Big Goals and Expanding Mission Pillars | 4 | 6 | 1 | 1 | Lenny probes into Canva's core value of 'crazy big goals.' Melanie details how breaking down massive goals into explicit mission pillars enables sustained decade-long compound execution across languages and devices. | |
| Managing Goal Timelines and Building Celebration Rituals | 5 | 5 | 1 | 3 | Lenny pushes on how to prevent team demoralization when audacious targets inevitably slip, comparing it to Elon Musk's timeline slips. Melanie admits they are rarely accurate on deadlines but maintain morale via eccentric celebration rituals like smashing plates. | |
| Scaling Pains and the Grueling Two-Year Codebase Rewrite | 4 | 6 | 1 | 1 | Lenny inquires about Canva's major existential crisis points during hypergrowth. Melanie shares the painful two-year period where shipping froze entirely for a full codebase rewrite, using rubber duck gamification to maintain team spirits. | |
| Transforming 100+ Investor Rejections into Pitch Deck Clarity | 4 | 7 | 3 | 1 | Melanie explains her mindset facing over 100 investor rejections, stating plainly that she believed the investors were wrong. She details how every rejection critique was systematically converted into a new slide in her pitch deck. | |
| Fundraising Advice: Problem Articulation and Finding Your Tribe | 4 | 6 | 2 | 1 | Melanie offers advice on fundraising and leadership authenticity, rejecting the notion of copying playbooks from other companies. She recounts how dogmatic Silicon Valley models like Lean Startup were fundamentally misaligned with Canva's vision. | |
| Sponsor Message: Justworks HR and Global Payroll Platform | 3 | 4 | 0 | 0 | Following a sponsor read, Lenny explores personal sustainability and avoiding burnout. Melanie discusses establishing strict digital boundaries, such as removing email from her phone to maintain clear cognitive focus. | |
| Community-Driven Product Iteration and User Testing Rigor | 4 | 6 | 0 | 1 | Lenny asks how Canva closes the loop on customer feedback. Melanie outlines their massive user request triage engine and her personal practice of running thousands of remote usability tests to detect subtle user friction. | |
| Canva's Two-Step Plan: Wealth Creation for Global Impact | 4 | 6 | 1 | 1 | Melanie details Canva's two-step plan to build one of the world's most valuable companies in order to do the most good possible. She explains their pledge of 30% company equity to charitable initiatives like GiveDirectly in Malawi. | |
| Canva's Major Workspace Expansion: Video, Email, Forms, and AI | 5 | 5 | 0 | 1 | Melanie reveals Canva's major workspace expansion into video, email, forms, and embedded AI collaboration tools. Lenny clarifies the exact scope of the email product and Canva's convergence across creativity and productivity suites. | |
| Finding Market Gaps and the Problem-Centered Approach | 4 | 6 | 2 | 1 | Lenny probes how Canva established its initial wedge against incumbents like Adobe. Melanie explains that they ignored competitors entirely, focusing exclusively on unaddressed user pain points starting with school yearbooks. | |
| AI Corner: Product Integration Philosophy and Personal AI Workflows | 4 | 5 | 0 | 0 | Melanie discusses practical AI product philosophy and her personal 'AI walks' where she dictates stream-of-consciousness ideas into Canva Docs for instant synthesis. | |
| The 2050 Vision Wall: Shaping Humanity's Future Through Imagination | 4 | 7 | 2 | 1 | Melanie describes her twenty-fifty vision board, expressing deep concern over the current trajectory of society and advocating for deliberate, collective imagination to solve basic human needs and pervasive loneliness. | |
| Lightning Round: Books, Daily Rituals, Core Mantras, and Grit | 4 | 5 | 0 | 1 | In the lightning round, Lenny asks about Melanie's competitive figure skating background. Melanie draws a direct parallel between repeatedly falling on the ice at 4:30 AM and building resilience as a technology founder. |
Statements from this episode (28)
Perkins: Transformative building requires working backward from an ideal future
“Most planning is often done by looking at the bricks and trying to stack them. And then you kind of, you know, you can create only so much. And so I guess the column B thinking is thinking about what is that magical, wonderful Future. That you then want to inv…”
Perkins maintains a vision wall in her home office targeting 2050
“Right now I have a wall in my house, in my office, which is my vision for what I'd like the world to look like in twenty-fifty.”
Perkins: Canva plans by defining wild success and failure over 10-year horizons
“An exercise we often do is like, what is wild success for X or what is wild success for Y? And then equally, what is terrible failure for those things? And you can apply that just to abstract thinking in different industries. You can do that, apply that for we…”
Perkins: Canva operates on a two-step plan to maximize value and philanthropy
“We've got this two-step plan, build one of the world's most valuable companies and do the most good we can do.”
Perkins: Realistic goals lead to giving up when roadblocks hit
“If you start with a Reasonable goal or a realistic goal, then you kind of get to get to when you're like, oh, cool, whatever. Or more importantly, if something happens, you know, all the problems and roadblocks come along as they always do, then you're like, o…”
Perkins: Canva achieves ambitious goals despite inaccurate delivery timing
“I think with a crazy big goal, the thing we have been really great at is achieving them. The timeframe that we achieve them on has not always been very reliable. We have certainly not been able to have pin dart. What's the, what's it? We have not been very acc…”
Perkins: Internal systems break every time a company doubles in size
“Like every time the company doubles in size, pretty much all your systems break, all the things that were working don't work.”
Perkins: Canva spent two years without shipping product during codebase rewrite
“We were doing a front-end rewrite, and we thought it would take about six months. It was really important because it was critical for cross-platform, it was critical for right to left, it was Critical because we could only have five people working in our edito…”
Perkins: Canva employs 2,500 engineers
“We've now got, you know, two and a half thousand engineers, and we're able to deliver amazing things that would have just, like, been completely infeasible.”
Perkins: Most early investors knew nothing about design or Canva's market
“Most investors knew absolutely nothing about design or the industry that we're in.”
Perkins: Canva's 2012 pitch deck still captures its current work
“When I look back at our 2012 pitch deck, it's so valid and really still captures what we're doing today.”
Perkins: Copying organizational playbooks from other companies rarely fits your company's foundation
“And it's kind of like building a house that you want every brick in the house to match. And if you go and try and take some bricks from someone else's house and stick it in your house, it's probably going to not look very matched. And so trying to find things …”
Perkins: Most companies' daily execution diverges from their stated mission
“Often people have a mission that's kind of on the wall somewhere, and then what they're actually doing and the way they actually make money And the way that, you know, the way people actually spend their time is in a very, very different direction from that or…”
Perkins printed early yearbooks on presses in her mom's house
“In our very first company, we actually had printing presses because we were printing the yearbooks in my mom's house. And then delivering them to schools around Australia.”
Perkins does not keep work email on her phone
“I don't have emails like on my phone, and so when I shut my laptop, I actually tune out, and then I, if there's a real issue, I'll get an emergency call or page.”
Perkins: Canva receives over one million community requests per year
“We get more than a million requests from our community every year, and we then, we've got a whole incredible team that then tallies them breaks them down, And then deliver them to all of our product teams, and then those actually get closed. So this year we've…”
Perkins: Testing 10 random online users yields representative product feedback
“It's amazing to me how you can find 10 random people on the internet and they can give such astute feedback. That then is so representative for such a large number of people.”
Perkins has personally run hundreds or thousands of user tests
“I've personally run hundreds, if not thousands of user tests myself, and it's been deeply embedded in our product teams also.”
Perkins: Co-founders pledged 30% Canva equity to philanthropy
“Cliff and I owned a little over 30% of Canva, and so we decided we were going to take 30% of Canva and use it to do the most good we can do.”
Perkins: Canva Foundation donated $50M to GiveDirectly in Malawi
“Over the last few years, we've donated fifty million dollars to give directly, where they give money directly to people in Malawi who are in extreme poverty, and then they can use that money on their family to go to school, to get healthcare, to start small bu…”
Perkins: Canva pledges $100M over four years to fight extreme poverty
“Announce that we're going to be giving another hundred million dollars over the next four years to people in extreme poverty.”
Perkins: Canva's free education product reaches 100M monthly users
“Education product is now used by a hundred million people each month.”
Perkins: Canva donates $1.5B worth of software annually
“Between our education product and our nonprofit program, where we also give away our paid product for free, We've, we're giving away 1.5 billion dollars of product a year now”
Perkins: Canva Elements tab sees 900 million monthly uses
“Inside the Design tab which is used by a 170 million, it's used a hundred and seventy million times a month. And then on our Elements tab, which is used nine hundred million times a month”
Perkins: 100 million people design presentations in Canva monthly
“Like a hundred million people, I design a presentation in Canva for each month now.”
Perkins: Canva sits directly between creativity and productivity suites
“From a macro perspective, there was creativity tools and productivity tools, and what Canva really does is we're literally smack bang in the middle of that Venn diagram of creativity and productivity rather than making a Customers have to make a choice between…”
Perkins gave over-the-phone tutorials to early Fusion Books customers
“We spoke to every single customer. We gave them an over the phone tutorial. We understood. All of their pain points, we got continuous customer feedback, and then we tried to iterate and improve.”
Perkins: AI shouldn't be front-and-center just for investor hype
“Just because AI is all the rage and investors really like AI, doesn't necessarily mean it should be front and center
in, but if it can genuinely help your customers to achieve their goals, so, you know, the thing that I was mentioning before, enabling people…”