Notion in Motion: The 2+1 Cofounder Combo

INTRO

Hey, I’m Tim! ☕

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Read on if you want to know why Notion and its cofounders are so special — and what you can learn from them if you want to build a company like theirs.

DEEP DIVE

“If we want to build the new, we must be willing to let the old burn.” — Glennon Doyle, author, founder of Momaster (community) and Together Rising (nonprofit).

Notion’s Nucleus

I started using Notion back in 2020, when I was building my last startup.

My cofounder suggested we use it to organize our projects, and to be honest, I thought it was a bit overkill at first. I literally draft these newsletter editions with pen and paper.

Over time though, as our projects became more complex and our team became larger, our reliance on Notion grew. Since then, I’ve used Notion at pretty much every job I’ve had.

But I didn’t know a thing about their cofounders.

A couple weeks ago, they reached out to sponsor Cherrytree. They reached out. To me. That blew my mind.

I’d been a fan and advocate for years now, and let’s be real, they’re a huge success story in the startup world.

So I did some digging. It turns out, their cofounding story is just as impressive as their product.

In 2013, Ivan Zhao and Simon Last set out to build the “LEGO of productivity tools” so non-technical users could make their own tools without writing code.

Over the next two years, they hired four employees and raised about $2 million from angels. The tool, however, was built on a suboptimal tech stack, which made it crash constantly.

In 2015, they were faced with a choice: run out of money or start all over.

They decided to lay off their employees, leave San Francisco, and move to Kyoto, Japan where they would rebuild Notion from scratch.

I was faced with the same decision 3 years into my last startup, and I decided to shut it down, so I have mad respect for them.

While in Kyoto, Ivan and Simon spent up to 18 hours a day coding and designing. They rebuilt Notion 4 times in the next 3 years before moving back to SF.

Years before this, in 2011, Ivan had posted a message on Hacker News looking for a job as a product designer.

Akshay Kothari, CEO and cofounder of Pulse, wanted to hire him. Although this didn’t happen, the two kept in touch.

In 2013, Akshay sold Pulse to LinkedIn for $90 million. After a five-year stint at LinkedIn, he left in 2018 to join Notion as its COO and third cofounder. (More on him next time).

While at the time it probably felt uncertain, it’s safe to say now that it paid off. In 2019, they hit a million users; in 2023, 30 million; and today they have over 100 million.

First Block

To borrow Notion’s LEGO analogy, the cofounders are the first building blocks of the company. Akshay even hosts a video series called First Block where he interviews other cofounders.

One of the episodes naturally features his own cofounders, Ivan and Simon.

It’s about an hour long — I pulled out some gems for you.

In reference to Akshay coming on 5 years later and still being a cofounder, Ivan says "a cofounder isn’t defined by being there on the first day but by being there for all the ups and downs.”

They also agreed that, looking back over the highs and lows of the past decade, it always came down to the people by their side. I’m sure you feel the same.

One comment really summed it up: “I can almost see their closeness like a married couple…they look at each other, knowing that they’re both thinking the same thing, but trying to decide who will be the one to say it.”

Here are 3 key takeaways you can apply to your own cofoundership.

1. Embrace Intentional Naivety in the Early Days

   Ivan and Simon’s goal to build a “LEGO for productivity” was bold, even naive. But by embracing flexibility over rigid plans, they let Notion’s potential unfold through trial and error.

2. Invest in Recommitment at Key Stages

   Building a reset mechanism in your cofoundership allows you to pivot without eroding trust. As your company and product go through shifts, your cofounder relationship needs a clean slate too.

3. Trust Your Gut

   There’s no risk-reward analysis that justifies moving to Japan and starting over, yet that’s exactly what they did. I often get calls from cofounders facing tough dilemmas asking me what to do. By the end of the call, though, they realize they already knew the answer — they just needed a little clarity.

Be a pace-setter and a truth-seeker in your cofoundership, which are two of Notion’s core values.

LAST LOOK

If you want more personalized advice, book time with me here.

Missed a Cherrytree edition? Grab a coffee and hit the archive to get all caught up.

Thanks!

Tim He