Connor Sears, founder and CEO of Rewatch, joins Adam to share the journey of creating Rewatch. What began inside of GitHub to help them thrive and connect is now available to every product team on the planet. Rewatch lets teams save, manage, and search all their video content so they can collaborate async and with greater flexibility. We talk about where the tool’s inspiration came from (spoiler alert, inside GitHub it was called GitHub TV which you’ll hear during the show), how teams leverage video to reduce the constraints of communication, how Connor and his co-founder knew they had product-fit and how they grew the team and product, and of course the flip side of that — we talk about some of Connor’s failures along the way, and knowing when it’s the right time to take a big swing.
Matched from the episode's transcript 👇
Connor Sears: That’s really interesting, I didn’t know he said that. I don’t know if I would use those words, but making sure you’re focused on the right thing is what keeps me up at night. Or when I feel like we’re not focused on the right thing, and I’m at fault for that, because I sent us all down this path, and maybe we’ve learned a little bit more. Oftentimes – again, this goes back to the… At the end of the day, it’s pride and an inflated sense of self when you feel, especially a CEO, whatever that title is, is inflated enough itself. But you’re taking all the responsibility of a decision, and if at any point you feel like, “Oh, I can’t change my mind,” or “With new information, we can’t shift”, that’s when you’re just in your own head. And honestly, it is pride that like, “Oh well, everybody’s expecting me to have known it before.” No, they don’t. They don’t expect that of you. I’ve always respected leaders, and what I hope the people that I work with see in me from time to time is, “Hey, there’s new information. We’ve learned a little bit more, and we need to change things.”
[01:27:43.23] So yeah, the things that keep me up at night is usually the things that feel out of your control, but actually are, and so you just sort of have to walk yourself back from that. But I do think there’s some merit into the sequencing thing. I don’t know what his answer exactly was, but when I think about it, you’re lining up dominos; you’re hopeful that this is compounding value and impact on the business as you go. So you’re afraid you’ve made the wrong bet. And there’s ways of de-risking that. I think the way you do it is talking to customers, talking to your team, walking through, and playing out the expected story in the future.
It’s one of the things - I know that’s played out now, but Amazon always writes the press release, for instance, for a feature. Well, I think you can do that and project it out into the future and say, “What are all the things that this is expected to do?” but also, do like a premortem. I know people do post mortems all the time, but like “How’s this going to fail? What are we going to run into? What are all the different ways that you think we could fail going forward and how can we mitigate that?”
I think honestly, planning… And when I say planning, I don’t mean like a six-month process to plan, or a business plan necessarily, but just talking through that… It helps. Again, we have open, transparent conversation, and I try to record my raw thoughts sometimes, and make it clear when they’re wrong. “I don’t have a high level of conviction around this idea yet, but here it is. What if we did X, Y, and Z?” I think those are the sorts of things that help with that quite a bit.