How a $725M VC Judges Your Engineering Team w/ Redpoint Ventures' Jason Warner

**Jason Warner** (0:00)
Do you understand why you've made technological choices and the trade-offs that you've had to do to get those? So, you know, if you're an app company and you're struggling to get people to sign up and use your app, and you're talking about a fully distributed systems back end using Kubernetes and ultimately scalable to tens of millions of people, you've lost the plot. You're not getting enough people. Focus on keeping your costs down and your infrastructure simple and get more people to use your app on a regular basis.

**Conor Bronsdon** (0:27)
Hey everyone, it's Conor Bronsdon, Dev Interrupted executive producer. So you might have heard that back in September, we held our first ever live virtual engineering leadership conference, Interact. With over 600 engineers and engineering leaders in attendance, Interact was a big hit with our audience and produced some amazing interviews, like Maria Gutierrez's talk on scaling engineering processes, which has become our biggest episode of all time.
So I'm incredibly excited to announce that Interact will be making its return on April 7th. You can register or learn more on our website, which is provided in links. We hope to see you there. Now, on with today's episode.

**Dan Lines** (1:01)
Hey everyone, welcome to Dev Interrupted. I'm your host, Dan Lines, and today I'm joined by Jason Warner, Managing Director of Repoint Ventures and former CTO of GitHub. Jason, thanks for joining us.

**Jason Warner** (1:15)
Thanks for having me.

**Dan Lines** (1:17)
Yeah, awesome, man. So a little background on you that I've written up. So you spent four years as a CTO at GitHub.
You've been an angel investor. You've been a VP of engineering for Heroku, these small companies that nobody knows.
Just kidding. You've done a little bit of everything. Most of our audience are engineering leaders themselves, and I know they would love to hear the story of your journey from being an engineer to an engineering leader, investor, and now a VC. So what's your background? How did this all happen?

**Jason Warner** (1:49)
So how I got into engineering is serendipity, basically. Grew up in Connecticut, in the States, didn't have a computer in the house for a long time. I wasn't one of those kids that started coding at eight. Essentially, what happened is, in the town where I was going to high school, IBM was there and they would hire high school kids to basically carry printers and computers around high school co-op kids.
They got a tax break for that. When I applied because my auto shop teacher said I should apply because that's a way for kids to break out of circumstance. I was the only kid that applied that didn't have a computer or a car that they got on their 16th birthday. So this is exactly why these types of internships exist.
So I literally got my start in computers by carrying them around IBM's building for a tax break. Then I started asking people, what the hell do you do with these things all day?

**Dan Lines** (2:48)
Life is interesting how that stuff happens and now look where it's led to you. You did the four years or so at GitHub. Tell us about that because that's just an unbelievable company, and there's a $7.5 billion acquisition by Microsoft.
What was that like for you?

**Jason Warner** (3:09)
Obviously, it was a ride in all the good and bad senses, but in the good senses, it was a ride. It was fun.
GitHub, there's not a developer on the planet who doesn't know what GitHub is. Yeah. When you think about the ability to influence or impact the entire field of software, there's very few places in the world that could have had as large an impact. Not in terms of maybe dollars, in terms of that we were making at the time, we were making quite a bit of money, but there are only four entities in the world when I joined GitHub that could fundamentally change software, it was Microsoft, Amazon, Google, and GitHub, and that was it.

**Dan Lines** (3:46)
Yeah.
At a planetary level, everyone on the planet. What were some of those ups and downs that you could share with us?

**Jason Warner** (3:53)
Well, obviously, a bunch of the ups were the acquisition and feeling of that, and releasing some of the features that we did after we joined. GitHub Action is still one of the highlights of my career. The last thing that we incubated in the office of the CTO, which I ran towards the end of my tenure at GitHub, we incubated Co-Pilot, which you might know as the artificial intelligence code editor. That was a lot of fun. Those are always some amazing highlights.