The Challenges of running a Company | Steve Huffman

Because the users are already doing it for us.

Yeah. And I mean, as you're growing, you're encountering a bunch of challenges too. So is there a particular challenge in Reddit that has really stuck out to you?

You know, back in the early days, it was really our own incompetence. I'd never built a website before. I had never used databases. I was learning HTML and CSS and JavaScript pretty much on the fly. I'd done a tiny bit in college.

That is amazing.

I had never scaled anything before. So things, when I look back on it now, things that took me a year back then, I could do in a week now. But somehow we made it through that. But it's just funny. And I remember my buddy Emmett, the CEO of Twitch right now, he and I were basically on Instant Messenger all day. For basically 10 years. And back in those days, we would sit there and talk about how do you configure Postgres. And then later it was like, okay, how do you hire somebody? And then later it's like, how do you fire somebody? And it's just kind of like, how do you raise money? And the stakes of our conversations would increase, but it was pretty much like from the beginning, that early crew— Just constantly growing. Just learning how to do stuff together.

So how do you fire someone?

Well, there's a couple of ways. Quickly and with compassion is what I try to tell my team. When you've identified that somebody is not going to work out, you should move quickly. I have a couple, like, I only have 2 pieces of business advice, so I can't write a whole book. But one of the platitudes I repeat often is, I've never regretted firing somebody, but I've always regretted waiting to fire somebody. So you wanna move quickly when you've made that decision, 'cause it's the right thing to do for them. 'Cause once you've made up your mind that you're gonna fire somebody, or even worse, you've told other people you're gonna do this, then everybody starts treating that person differently. You start treating them differently, and that kinda creeps in. You don't trust them anymore, you don't give them big projects and this and that, and they can feel it. It doesn't feel good for you, it doesn't feel good for them. It's kind of disrespectful. And people really, I think more than anything else, just really want clarity so quickly. And then with compassion, it's like, don't be a jerk about it. And so for us, in a lot of cases that means like, what's the timing? Do you have something going on in your life that maybe we can work around? Do we maybe accelerate your vesting a little bit? Or do we figure out how to tell a different story? Like you wanna resign or you wanna take some time off or this or that. Assuming we have a good relationship, we try to make it feel good, right? 'Cause it doesn't feel good, but you can try to make it be humane at least.

And Reddit, you're a little bit transparent too, so the community gets involved whenever sometimes there's a fire.

Yeah, well, we've finally gotten away from that. I mean, we had the famous one that brought me back to work, 'cause I had left Reddit for 5 years, and then they, You know, I don't know, we could tell the story if you like. But basically they fired somebody, the community revolted, and then I came back.

The TL;DR is good.

So, and then, but we had this problem when I came back to Reddit in 2015. It was tough. And the team, like, we had to do a lot of turnover on the team. And at the time, you know, we had, call it like 70 employees or something. All of the employees were listed on an employee page with their name and their Reddit username. And so occasionally we'd let somebody go and we'd take down their SNU from the employee page. And so we were basically in public firing people. And so if the community liked that user, they'd get angry at us. Or TechCrunch would be like, oh, Reddit fired 3 people today, and this and that. And it'd be like a big news story. So we took that page down. 'Cause it's like, it was just like, I was like, they're reporters. And at the time, They were venomous. They really were out to get us. And I was like, we just can't give them any more ammunition.

I know you've gone through a lot of negativity on Reddit. How has that affected you personally and also professionally?

Well, I came back to Reddit when Reddit was in a— so just a brief timeline for everybody. We started in 2005. We sold early after 18 months in 2006. I stayed on Reddit for another 3 years as part of the acquisition. Acquisition contract. We got bought by Condé Nast, the magazine publisher. I left in 2009. I started a different company called Hipmunk, which does travel search. I was there as the CTO for 6 years. And then Reddit was going through some really tough times in 2015. At that point, they had actually spun out from Condé Nast to become an independent company again. And so I returned as CEO in 2015. And at the time Reddit was just getting killed. The users were in open revolt. We were getting crushed in the press. Morale at the company was very low. And yeah, that definitely took its toll on me. And we were fighting some really kind of ugly content on the site. It was just kind of nasty stuff that we just really did not want to be there. And it was not reflective of the vision of what we wanted Reddit to be. And so that was tough. That was mentally very tough and physically very tough.

Watching it from the outside happen to kind of your baby. Yeah.

It was unpleasant because—

Did it pull you back to it? Because you were at Hipmunk at the time.

Yeah. For a while, I really enjoyed my time at Hipmunk. We had a great team and great people. I can't say I ever loved travel. But my co-founder, the CEO, loved travel. And that's his job. But I love building things. And that was my job. Watching Reddit grow and kind of face these difficulties and watching the product not really evolve, the volume in my head started to increase around, I'd really like to go back. I've learned, Hipmunk was such a good experience. I developed a lot as both an engineer and a manager and a leader. And as a company, we got really disciplined about how to grow the product in a way that we never were at Reddit.

Yeah. Mm-hmm.

At that point. And so I was like, you know, I've developed all these new skills, and I have this perspective, and I'd really love to come back to Reddit. But it was just practically very difficult for me to leave Hipmunk. And so in fact, I was talking to Reddit in the months leading up to that summer about coming back, but we could just never quite figure it out. And it basically just hit this point where My desire to not see Reddit die outweighed my desire to stay at Hipmunk. But it was one of the most difficult decisions I've had to make in my life.

It sounds like it was a tough decision for you.

Well, 'cause I felt like I was breaking promises to everybody who worked at Hipmunk. 'Cause a lot of what I did at Hipmunk was recruiting and getting people, selling people on this vision that, hey, we're gonna take on travel together and we're gonna succeed together and we're gonna build these things together. And then to leave, especially as their leader, was very painful.

Do you still feel like that now that you're over?

We've hired a lot of Hipmunk away. So I've tried to do right by that team. And Hipmunk sold to Concur last year. And so there's a good landing for the employees who are still there. So the people who stayed at Hipmunk and were loyal to Hipmunk did well. And so I feel very good about that.