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 toolâs inspiration came from (spoiler alert, inside GitHub it was called GitHub TV which youâll 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 â we talk about some of Connorâs failures along the way, and knowing when itâs the right time to take a big swing.
Connor Sears: And they looked at it, and they just, âHey, are you serious? Did you forget to fill this part out?â We were like, âNo, weâre doing everythingâ, and the whole deal fell apart. [laughs] And that was the reason why. It wasnât that they didnât believe us. I think even from that standpoint, it was evident that we werenât scaling ourselves, and that there are natural consequences of that, like whether or not things slip through the cracks. Or in my case, I canât do all the design, it turns out. It turns out that I need a lot of help with that.
[01:12:09.23] Or that Scott being the only person who can fix the website if a bug pops up, and having to wake up in the middle of the night all the time, and not being able to distribute that burden. I think those are all just very small examples. But I think this is something that we constantly deal with as a team.
Now, thereâs this fine balance between being lean - and we do, we try to run a lean, efficient startup that is focused on building a business. Weâre not trying to spend a bunch of money just because you have it. I thnk that story is played out, and itâs not one that I want to sort of participate in. So when we spend money, we do it very intentionally, and sometimes what that means is that we hold off hiring a role until it is absolutely painful to not have a person doing this.
But to your point, I think the other thing that needs to balance that out is getting too comfortable just hiring and then saying, âWell, that problemâs solved. Somebody does that now. I donât have to worry about it.â
For me, personally - as a founder, you sometimes err towards focusing on what you like doing, even if thatâs not whatâs best for the company. So thereâs been times when my focus really needs to be on go-to-market, it needed to be on sales. All this stuff that, before starting a company, I really donât have that much experience with. I have zero experience, letâs just be clear. But thatâs the beauty of startups, is that youâre learning constantly. And itâs not just enough to learn, but like you said, you have to do the job, you have to do founder-led sales, you have to learn everything you can about things that youâre not comfortable with. If anything, a startup puts you in very uncomfortable situations, where you have to sink or swim, you have to learn how to do something. And it could be sales, it could be marketing, it could be a little bit of engineering, it could be anything. Support, customer success - all these things, you canât outsource it.
Every time I talk to a founder and theyâre like, âOh, I hired a contracting firm that will just handle this for meâ, or âI just hired this person now. I donât have to think about that.â On one hand, more power to you; thatâs great. If youâve found somebody who can do this at a high level, that is great at the job, and that you can put a lot of trust into - fantastic. Itâs what everyone is looking for. But I would still say, especially early on, you just canât outsource core parts of your business.
Finding that balance, itâs a daily â I wouldnât call it a struggle, but itâs a daily challenge. Itâs like understanding, youâve got to scale yourself, you can only do so much, and you have to focus as a founder on where you can provide the most value for your company. At the same time, youâve got to understand the different components of your company, and youâve got to know enough to jump into any conversation and at least have some sort of understanding of whatâs going on, while building a team around you that can educate you.
I like being able to get into a room and saying, âHey, everybody. You know Iâm an idiot when it comes to X. So treat me like an ignorant fool, but hereâs some questions I have.â And then that age-old question thatâs like, âWhat are the unknown-unknowns for me that you all know I should be asking about, but Iâm not asking about?â That helps level you up, and definitely, itâs one of the things Iâm most proud of is the team that we are building, that can bring that expertise to the table, and feel comfortable to talk to me when Iâm not thinking through something deeply enough. Because oftentimes, I look at something and itâs a bunch of arrogant people do like myself, I say âThis is simple. It isnât that complicatedâ, and actually it is. âOkay, cool. Letâs talk through it and letâs figure this out together.â