Episode 1: Alexis Ohanian, co-founder of Reddit and Managing Partner at Initialized Capital

Front co-founder and CEO Mathilde Collin is on a quest to understand how companies can help their teams find meaning in their work. In this episode, Mathilde sat down with Alexis Ohanian, co-founder of Reddit & Managing Partner at Initialized Capital, to discuss how leaders need to prioritize their own health and wellness and be role models for their teams in order to see business success.


MATHILDE COLLIN: Hi everyone. I'm Mathilde Collin. I'm the CEO and co-founder of a company called Front. I started this company because I wanted more people to come to work everyday and be happy. And so earlier this year I started dedicating more time trying to understand what companies can do to provide more meaning and happiness to their employees.

And as part of this journey I've been meeting with interesting people that have some perspectives on how companies can bring purpose and happiness to their employees' lives. So today I'm very excited to be with Alexis Ohanian. He was the co-founder of Reddit. He was a partner at Y Combinator, that's where I met him. And then he started a VC firm called Initialized that actually was one of the first investors in Front.

And the reason I'm excited to have Alexis is because he has spent more and more time recently talking about wellbeing at work. And one of the things that he has been talking about is the obsession that we have with hustling, and how it can prevent entrepreneurs from doing their best work. And how it just reinforces the stereotype that in order to win in business you just have to devote your life to it. So, Alexis, thanks so much for being here.

ALEXIS OHANIAN: My pleasure.

MATHILDE COLLIN: One of the thing that I've realized is, now people when they think about their job, they're not happy anymore with just a regular job, or just building a carrier. What they want is meaning, they want to be happy, they want a calling. So my first question would be very personal, which is, do you find your job meaningful today?

ALEXIS OHANIAN: Yes. I would not be doing it if I didn't. Actually I was on a paternity leave welcoming the birth of our first and only child. And, thank you. She's two now. So time flies. But I was there really with a lot of time to think about what was giving me purpose and what was fulfilling me. And the litmus test that I used was the quality of the dinner table story that I had at the end of the day.


ALEXIS OHANIAN: Now my wife has a very interesting job, and she has a lot of great stories at the dinner table. And I wanted to think about the stories that my daughter would hear as she got older. Because dinner a really important time for us because we are so busy, we really try to make that time sacred. So no phones, etc, etc. And I wanted to have stories (I'm very competitive) that would compete with my wife's. And what I found, certainly, and I'm very proud of the work that the team did. You know, I came back to Reddit in 2014 when it was probably at its lowest. And the turnaround has been very successful. And I'm proud of the work everyone did. But in the process of getting there, Reddit went from like 40 demoralized employees, to I think 400 really active and excited and driven people.

But the size of the org meant the nature of the work that I did most of the time was drastically different. And this was something I had never experienced before. I had never been at the top of a company that big. And I just found most of my days were spent doing some version of executive therapy. And I knew that while, I mean there's real value there. There are people who definitely have super powers around organizational structure and management, especially that size. But I, when I was being honest with myself, realized where I really found my joy was working much closer with founders still in the earliest days of the creation process. Really going from zero to one. And my partner Gary Tan, who's a co-founder at Initialized, also was a partner at Y Combinator. And you know him well.

You know, Gary came to me and said, look, he's very convincing, he's like, you know, it's great. It's amazing that you've created $1 billion company. But with Initialized we have the chance to help create dozens. And really be able to scale that expertise, and really be able to scale that impact. And I mean, he made a very good point. And so now I get this amazing job where I get to talk to founders, and even though the vast majority of the time we don't invest, I'm still learning something new. I'm every day learning something new from my partners, or from founders that we meet who are obsessing, focusing their entire lives on solving a problem. And I'm learning something.

And the stories that I get to bring home are ones that I hope entertain. I don't know. I don't know, they might be more boring than I think. But for me at least, are very meaningful, very purposeful. And then when we do get to invest in great founders and get to help them as best we can, but really also concede the point that there's only so much we need to do. Great founders are the ones actually running the businesses and growing the businesses. But to be able to be privy to that, it's like the best professorial job there is, because there's always a new incoming class of founders. And you get to take such pride in seeing these, like super early stage founders who just have a dream, able to bring it to fruition. And it's deeply satisfying. And so I optimized for the dinner story. And I think it's been totally worth it.

MATHILDE COLLIN: Well that's fascinating. One of the things that I can't help thinking is you've been successful with Reddit, and so then you were able to afford thinking, okay, now what's next and what will bring more meaning to my professional life? Do you think that every single person should think about it so that, or do you think everyone should try to prioritize work-life balance and try to find meaning in their life? Or do you feel like you have meaning and you have this balance because of your success before?

ALEXIS OHANIAN: Yeah. So this came up a lot, especially in light of my hustle porn comments. Because really the only criticism folks had, and it's not really criticism of hustle porn, but their criticism of me around it was, okay, well it's easy for you to say that now. And I know how lucky I was. I mean, we sold Reddit very early the first time. Thankfully I got a second chance. But we sold it very early, it was 16 months worth of work for what was life changing money for me. And that, I don't regret. And it did give me the peace of mind to be able to really optimize for the decisions I wanted to make in my life. And I know how fortunate that is. I also know that if I had been investing more in my mental health, my physical health, coaching during that time of Reddit, which was not just founding a company and all the normal stresses, but also a difficult time for me personally with my mother getting sick and some other personal stuff happening, that I know we would've had a better outcome.

And I can't re-live that. I can't replay that. But what I can do is now in my role as a mentor and an investor, be able to start to change the narrative about how a founder should be optimizing selfishly for their business by investing in themselves, and taking time for themselves. Because, especially in the earliest days, you really are so much of your business, you and your co-founders. The team is so small and so reliant on you, that yes, you obviously have to work hard. There is no one I hope on this planet who'd think that you can find that success without a tremendous amount of work. But what I have found is that the most successful founders are one not posting hustle porn quotes on their Instagram. Most of them aren't even on Instagram. But more importantly, they know that the time they have to reflect, to exercise away from work, to recover, the time that they invest in themselves not working actually helps their bottom line. Actually helps them be better when they are at work.

MATHILDE COLLIN: Yeah. One thing I'm curious about is one of the reasons why I became more passionate about being more healthy, spending more time not connected to work, meditation, therapy, etc. My co-funder got sick like two and a half years ago. Which was the worst period of my life. And it seems like you had a very similar story where you had to get to a point where you were maybe so unhappy that you started thinking about prioritizing it. And then you saw how much happier you could be. So my question would be for all these people that don't have these very, very tough experiences that they use as a turning point to prioritize their mental health and their wellbeing, what have you found being most compelling in order for them to still prioritize this? And since you're working with so many entrepreneurs, I'm sure that there are some where it resonates and some where it doesn't.

ALEXIS OHANIAN: Yeah. I really do think modeling the behavior goes a really long way towards just giving founders the clearance or the comfort to be able to say, okay, I hear you and I can actually do this. And specifically, right, we are... Specifically we run Initialized to be the... We want to be the first and largest check in a company. So we have a lot of influence over the founders, and we do that because we know we want to do the work to support them. And part of that is being able to role model this behavior where we carve out very specific times. Like I've literally, I have paused meetings because it's tricky with time zones when your family's traveling everywhere. And so I've had meetings here on the West Coast, actually fairly regularly with founders during working hours when it is bedtime back for Olympia. And it is blocked in my calendar.

And I apologize to the founders and say, look, I'm really sorry I have to step out. I've got to do prayers, we have bedtime story. I've got to do this with my wife and daughter. And it's probably a weird thing for most founders to have to do. I mean, there's other people in the room usually we have, like the meeting does not just stop and everyone's kind of just twiddling their thumbs waiting for Alexis. But the reality is, I have to draw hard lines around important things in my life that nourish me personally in order for me to do the exceptional things in my work life. And I expect founders to be able to do the same. And I would not want any of them have to go through some kind of big trauma to have to realize that.

But I want them to see it being modeled by the people who are most financially invested in their success, walking the talk as well. And that's I think the thing that they start to see, which is, I hope no one would dare accuse me of not being competitive or successful as an entrepreneur. And I actually think, and I've had startup people at all ranks, from interns to founders, CEOs, at various points relay this feedback back to me. That it makes a difference. And whether it's talking about paid family leave or whether it's getting up for a really important scheduled session with my daughter, it signals a conviction that shows them, all right, this matters.

And so we do our best. I mean, I think even when we go through, I mean you remember the office, it's been a long time since you were a seed stage company. But those regular office hour sessions, I want those to be a chance for a founder not just to talk about the things that are going wrong with the business so that I can try to help, but also a chance for them to talk about the things that they're struggling with personally right now, so that I can help. Or so that I can just simply say, you really need to take this weekend and do whatever you need to do to recharge.

And it's not on me to prescribe what that is, it's on you to figure that out. But the prescription I'm giving you is, is take some time for yourself. And whether that is a camping trip or just locking yourself up in a cafe reading a book. Great. But find your ways to recharge and replenish. And we're luckier than ever now because of technology that our relationship to work is, it's a gift and a curse. It can be both ever present... And actually, I've been keeping up with the notification challenge that you issued me on. And it's been great. And so we have this technology that we can shut off and say, no, no, no, you are a tool. You don't run my life.

By shutting off notifications, we can make sure to do an even better job separating time and focus. And at the same time, it's the thing that lets me, when I know I need to get some shit done on a Saturday from, I don't know, an airport in Des Moines, I can actually get it done. And it is a blessing when that tool is actually working for you. And I think it's more important than ever that we have this behavior as something that is demonstrated. Because we have these things, we actually have these things. And that's why I loved your challenge.

MATHILDE COLLIN: Well, so just some context on the challenge is, I told Alexis that he should remove all the notifications on his phone for, I think, a week or a month. I can't remember. And people are scared initially to do this, but then they see the value. And so he did it. And since then I think he did not miss the notifications.

ALEXIS OHANIAN: I haven't gone back.

MATHILDE COLLIN: Yes. And I mean, I pushed it a little bit further where I deleted all my apps. So now I just have my communication apps. So meaning WhatsApp, text, Uber, Venmo. I don't have any other work apps, so I need to work out of my computer or a network. So you can try this challenge for a week if you want.

ALEXIS OHANIAN: That's expert mode.

MATHILDE COLLIN: Well I'll send you an email and you can try.


MATHILDE COLLIN: One question I have is, so we've talked a lot about how we can, and how specifically you can, help founders prioritize their happiness. What do you think founders can do in order to help their employees prioritize their happiness?

ALEXIS OHANIAN: You know, I have learned a lot from our VP of people and culture at Reddit, Katelin Holloway. She joined Reddit when there was literally no HR. She was the one who famously originally brought me the paid family leave program and was like, okay, this is one of a hundred things that we need to implement at Reddit. And she was right. But the thing that's impressed me most is, and she very quickly understood that what was right for encouraging this kind of happiness at work also needed to be right for the company culture itself. And so I think in many ways this has to, one, be something that starts with a founder being able to set a tone themselves in what they do and in many ways practice what they preach.

And in finding ways to build policies and programs into the office that are genuine. So I don't want to prescribe something because it may not work for your organization. But whatever they are should be things that are true from the founding core or the values core of the organization, and are actually policies. And I mean there's some sort of obvious easy ones that I don't think anyone argues with these days around flexibility at work. And this idea, at least in tech, of butts in seats is one, it was antiquated five years ago.

It is, whatever. It is ancient now because we all realize we don't have employees on an assembly line who need to put widgets together, right? These are employees who if they have a sick child, should be able to just take care of their kid and spend a day working from home. Right? It is shocking to me though how many of the, let's call it Fortune 500 companies that I've spoken to or met with, that don't really have nearly as flexible policy around this because they're still so traditionally rooted. And that's something that's going to go away very quickly because all of the talent that we get to work with here, that has created this amazing talent war, that's sort of given birth to a lot of these perks. If those talented engineers or product people or designers are ever going to be hired by the incumbents, those incumbents have got to adopt their policies.

And I actually think that's where something like paid family leave too, is going to spread even faster. Because once you set a standard for the very best, and frankly, arguably some of the most valuable employees in the nation's workforce, you set that standard now that eventually has to bleed through every other industry. Happiness, it is something that I think has started with benefits, and now I hear even more so. I mean, we backed a company called Torch because it provides executive coaching as a service. I think we're going to see more and more mental health resources that are paired as a part of company perks, childcare and things around family are, again, kind of no brainers. But even, look, for pet parents. We have a cash policy that Katelin brought that gives you some time and resources to spoil your furry child.

I know. I can only imagine. I have these conversations with my dad, who's obviously from a different generation, about this stuff. And it often gets seen or reported on through a lens of like millennial entitlement. And I think what we're actually seeing is a generation that has both been promised a lot of things that didn't come to fruition, like at least here in America, right? Go to college, don't worry about the student loan debt, you'll have a great job waiting for you. Not true. Real estate, it's a great investment. You're going to have a home. It's part of the American dream. Not true. We've seen a generation that was born through a lot of false promises that feels, yes, entitled to something that's actually true. Because they feel like they did the work. At the same time though, also got so empowered by a technology, the internet, that has enabled far more flexibility. And the ability to act on this feeling of all right, well if the system is broken, fine, I'm going to hack my own way.

Whether I'm going to become a founder or I'm going to become a full-time artist on Patreon, Initialized company, or even just find a way to creatively build the life that I want for myself. I want to travel two thirds of the year, like God bless, do your work freelance. And I think that all feeds into what is going to be a much bigger culture shift at work. That is the future. That doesn't get dialed back, and nor should it.

MATHILDE COLLIN: So since we're past our time, but I enjoy this conversation so much I have two last questions. The first one is, when you invest in a company today, is that criteria that you use? Like the fact that the founders will prioritize the happiness of their employees and their own happiness?

ALEXIS OHANIAN: It is. The adjective I use and that I'm trying to teach other partners, because it's sort of a je ne sais quoi. Excuse my French there. It's like a, okay I'm learning. I need a founder to be compelling. And what that means is not charismatic, it's not outgoing, it's not extroverted. It is compelling. It is, they deeply understand the problem they're trying to solve, the market they're trying to solve it for, and the people they need to bring on board to do it. And so I think part of that, because it all at the end of the day is going to come down to the team that they can build is exactly that. And so part of being able to have and retain those people is understanding what they want, how to give them fulfillment, how to give them a sense of mission and purpose.

And yeah, it's an unfair advantage when you know that a founder can crystallize why someone should want to work there beyond just, hey, you're going to have a great job and you're going to hopefully make a lot of money. And hopefully lots of people will love what you build. But something else that fills this other need. And great founders can do it with companies that are not ostensibly mission-driven. And Front is a great example of that, because on the surface you'd be like, emails? And you can see even among the earliest days in this sort of compellingness of a founder, this ability to realize what is going to delight not just users but the people who are going to join the mission.

MATHILDE COLLIN: Yeah. Any last words of wisdom for people watching us?

ALEXIS OHANIAN: I only want better things in this world. And I do believe that startups are one of the highest leverage, fastest, most amazing ways to create better things in this world. And so that's why I love what I get to do with Initialize. That's why I love being able to watch these companies grow and do wonderful work. And I'm grateful for the fact that this is, what you're identifying here is not something that comes from us. I really do think there is a changing trend now, and it is especially a generational one where more and more people are now realizing how important this is.

And we as leaders, at the end of the day, are just responding to those trends because we know we need to see where the puck is going, or where the soccer ball is going. And we need to be able to anticipate and build the organizations toward the kind of talent we want to be able to attract and retain. And so the thing that excites me and the thing that I hope people take away from this is that this is not a fad. This is where everything is headed. And it's one of the best things you can do for your organization is to invest in the happiness of yourself and the people on your team. And I'm feeling really self conscious now, like I should go back to Initialize to be like, is everyone happy? But that's what I'm going to do.

MATHILDE COLLIN: Please do it. Thank you so much. This was amazing.

ALEXIS OHANIAN: Thank you, thank you.