I built a business with a $4B founder - here’s what I learned

If you could spend one day shadowing a mega-successful founder, someone whose company IPOd on the NASDAQ, would that be cool? What if you could do it for six months?

I didn't realise it at the time, but October 7, 2019 was one of the luckiest days of my business life, because I got this email: "Hey Matt, I'm Gagan, co-founder of Udemy... I've heard your name a few times now and thought I'd reach out." I took the meeting!

Gagan Biyani did found Udemy (NASDAQ:UDEMY), and he was spending the year in Oxford where his girlfriend (now wife) was in business school. One call led to another, and we decided to collaborate on a project to explore and validate our next business ideas.

It was part amazing, part awful.

The amazing part.

We decided to launch a 10-week cohort-based course together, and that experiment led each of us to our next ventures. I now run my cohort-based programme, and he founded Maven, an A16Z-backed marketplace for cohort-based courses. But you probably want to hear about the awful part.

The awful part.

I like Gagan very much, but he was tough to work with. If you follow him on Twitter, you might have noticed that he’s very open about his challenging style. And, while I appreciate our time together, it was sometimes painful. But suffering brings many lessons, and I'm going to share the biggest one.

I’ve worked with hundreds of founders, and none of them are anything like Gagan, because he has no comfort zone. He’s bold and impatient. He wants to do everything, and quick. We had to develop the programme, promote it, and create and deliver the content.

To run this programme well, we'd need to be good at teaching, writing, and coaching, and, to be honest, he just wasn't. But that didn’t stop him!

I'm pretty good at writing and teaching, so I jumped in to do as much as I could, but he kept racing ahead, making every mistake. It was uncomfortable watching him make mistakes. But in hindsight, I realise they were small mistakes, and I was probably wrong to fixate on them. But I'm getting ahead of myself.

My mental shift

It's hard to watch somebody sprint ahead like a bull in a china shop, and I instinctively judged him harshly. But I'd cool off and remind myself, "This guy co-founded Udemy, and you did not." I'd bring myself around to the starting premise that he was probably right, and I needed to understand why.

With time, I figured out that he does the important work. He thinks about his goal, lines up the likely next steps, and jumps in, regardless of whether he knows how to do them or not. As far as I can tell, his comfort zone is discomfort. He does whatever needs to happen next. Sometimes he makes a mess of it, but one way or another, things move forward.

The big lesson: To succeed as an entrepreneur, you need to do the stuff that needs to get done, and it's almost never familiar or comfortable. Great entrepreneurs don’t hesitate to push into unfamiliar territory.

So I watched as he made mistake after mistake, and bear harsh feedback. It didn’t bounce off of him, he took it the way any of us would... It hurt, sometimes he'd get defensive and annoyed, and other times he was humble and contrite. But the thing is, he didn't dwell on it, he kept pushing forward.

Eventually, he moved back to the US and founded Maven, but we've stayed in touch. And looking back here's the thing that blows my mind...

The thing I never expected

All those things Gagan was trying to do, things he was bad at, he's now mastered them. He hired a writing coach and drafted some incredible Tweetstorms. He worked on his teaching skills and he’s quite compelling. I saw him achieve a level of skill in one year that took me decades. He's always uncomfortable, which means he's always learning.

Simple Next Step

Look at your to-do list. There's something on there that makes you uncomfortable, either because you don’t know how to do it, or because you might screw it up. Go do that thing.

I hope this helps.