Milo and Juni Discussion: Melanie Perkins

Okay, let's start with the framework that stuck with me the most. Column A vs. Column B thinking. Column A is what most people do. You look at where you are, figure out the next logical step, stack the bricks. Column B is different. You dream of the castle first, then work backward from there. That reframe changes every decision downstream.

What I love about that is how simple it sounds, but think about every planning framework you've ever read. Almost all of them are Column A. Start where you are, make incremental progress, measure the gap. Melanie's reframe is: don't start from the bricks. Start from the castle. That inversion is what makes it genuinely powerful and not just another goal-setting exercise.

Here's the part that would break most people. Over 100 investor rejections. A hundred. I keep wondering, what does that feel like on rejection number 74? What keeps you going back?

She actually answered that directly. She said, "I thought the investors were wrong, frankly." That's not just persistence. Persistence is gritting your teeth and pushing through. This is conviction. She genuinely believed the market was there and the investors were the ones missing it. That distinction matters.

There's a Canva value called Crazy Big Goals. And Melanie has this great line about what qualifies: "You feel completely inadequate before it." That is the test. If you feel ready, the goal isn't big enough.

And then, when they hit those goals, they don't just send a Slack message about it. They celebrate with plates and doves. Actual plates to smash, actual doves. They even did La Tomatina once. I think that tells you a lot about the culture. The goals are audacious, but reaching them is a shared event, not a private metric.

Let me bring up the Two-Step Plan, because this is the part I keep coming back to. Step one: build one of the most valuable companies in the world. Step two: do the most good you can. She gave 30% of her equity to the Canva Foundation. For a company valued at $42 billion with $3.3 billion in revenue. That is not a typical CEO move.

What's interesting is that it sounds sequential, step one then step two, but in practice she runs them in parallel. Building value and doing good at the same time. The $50 million to GiveDirectly, the Foundation work, all happening while Canva is still scaling to 240 million monthly active users. She said it directly: "Getting really rich is not a goal unto itself whatsoever. It's a means to an end."

I have to flag one of my favorite moments. Lenny asks her how you go from chaos to clarity. And she says, with this dry, self-deprecating delivery: "How do you go from chaos to clarity? You add clarity." It's so deadpan. But it's also kind of true? Each step is just adding a little more clarity to the mess.

Right. And the real insight underneath the humor is that the first step is supposed to be embarrassing. That is by design, not a mistake. If your first version of anything isn't awkward and rough, you waited too long. She took the chaos-to-clarity path from a student yearbook company to a $42 billion design platform. The starting point was intentionally small. That's Column B thinking in action.