Tiny Revolutions No.5: Interview with Ryan Williams, writer of The Influencer Economy

This is an edited and condensed transcript of a conversation I had with author, podcaster, marketer and sometime comedian Ryan Williams in July of 2018. Highlights from it appear in the fifth issue of Tiny Revolutions, my newsletter for high-functioning crazy people.

Sara: When did it become clear to you that you were dealing with depression?

Ryan: I think the first time I experienced depression was in college. I was going to go to travel abroad in Australia — this is a very first world problem, I’m aware of that — and I got sick before my trip. I wasn’t able to go. I was technically diagnosed with mono and it went from like, “I’m leaving in a month to go on an epic adventure that could help define my college experience,” to “I’m going back to live in a dorm room at Vanderbilt University with roommates I don’t want to live with, in a dorm I didn’t pick.” Looking back further, I probably slept a lot more than normal. The traits were there. But I had that experience in college, and then I did a summer on Wall Street as an intern, and I got really depressed.

Sara: Yeah. You don’t say? Wall Street.

Ryan: Yeah, it’s just an abusive environment. Have you worked on Wall Street?

Sara: I have not, but I have lots of good friends who have.

Ryan: The mental balance isn’t really there for people.

Sara: At all. One of the reasons I try to write about depression is because early on, I just wanted keep a very good facade up. Like, “I’m not really dealing with this, I’m just like everyone else. I don’t want this.” And I’m just curious — when you realized you were dealing with depression, what did you do to address it? What’s been your MO?

Ryan: Well, I sought therapy while I was in college. Senior Year. I didn’t tell anyone. I snuck over and walked to this place and had an excuse in my mind if someone saw me like, “Ah, I’m going to the drug store. I’ve got some things to pick up.” I had the whole routine down. I went to college in Nashville, Tennessee, and there was a therapist a couple blocks from campus. And she thought that I just needed to “charge up.” Like my batteries were low and I needed to recharge. She even thought that I was doing really well. And then I got chronically depressed after college. Deeply. Like, I stayed in a room for probably three months and didn’t really know what to do.

Sara: Wow. You weren’t working?

Ryan: I didn’t have a job, no. All my college peers were moving on. And I was in a fraternity and that environment is very…you know, there’s bullying and people one upping each other, and…

Sara: Not a lot of sensitivity?

Ryan: No. I once talked about depression on my podcast, and I got an email from a friend from college, and he was like, “Wow, I’m sorry. I had no idea.”

Sara: Wow.

Ryan: And that was all he did.

Sara: Interesting.

Ryan: And he was someone who was mad at me in college because I wasn’t getting up and doing stuff. He would challenge me. Which was not helpful.

Sara: You’ve talked publicly about depression. What led you to start doing that? Was there a moment? Or was it more like, “this is a story I have to tell?”

Ryan: Oh yeah. Well, I had to tell it because I was ashamed that I was depressed. Which is very common. I did stand up comedy while I was depressed, and that would help me get out to connect with people. I later realized I was not as great on stage as I could be behind the scenes, so it helped me define my career path. But it was a very extreme measure to take at the time, and looking back now, I can’t believe I did it. It’s almost like it wasn’t me.

Sara: Doing standup?

Ryan: Yeah. And just being depressed. Because I wasn’t myself. It’s hard to explain to people.

Sara: I’ve never written stand up, but that’s kind of what you had to work with, right? Material that you knew to some extent.

Ryan: Oh yeah. You’re writing jokes, but you’re also around a bunch of people who drink obsessively, and if you do well in comedy someone buys you a beer, most likely. They want to be your friend. The culture itself really attracts people that are often mentally, like, sorting themselves out through the comedy. In some ways it was lucky because I realized my problems didn’t seem to be as deep. I’d had different types of traumatic experiences, but because a lot of comedians talk about being an outsider, I realized I wasn’t as much of an outsider as I thought. So, it was helpful in that sense.

Sara: It’s funny you say that, because I feel like on the spectrum of different people and their levels of fucked up-ness, the ranking would be something like the most fucked up are the comedians, followed by the artists, followed by the musicians (laughs).

Ryan: Yeah.

Sara: Comedians are definitely the most, like, “Whoa. Okay. That’s pretty out there.” But, since we’re on that topic, you’ve worked in startups a lot, right? I feel like that is also a profession that attracts a lot of not very well-balanced people.

Ryan: Yeah. There’s so much anger at startups.

Sara: Well there’s so much hubris and so–

Ryan: Well, it’s arrogance.

Sara: There’s that grandiosity, combined with the wild swings at the company. I hadn’t really thought about it before, but it’s almost like you put entrepreneurs in that same category as artist.

Ryan: Oh yeah.

Sara: Where you probably have a little bit of a screw loose to get in to get into the whole thing.

Ryan: Oh yeah. And there’s this sense of entitlement a lot of people who are startup founders have. They feel like they deserve everything and if they don’t get what they want, there’s a lot of tantrums and anger.

Sara: Yeah. And at this point, if you are an artist or a musician or a comedian or someone like that, a performer, it’s sort of acknowledged that that is an “anything goes” kind of atmosphere. But I don’t know if it’s quite the same in the professional world.

Ryan: No.

Sara: So I guess the question for us is what are we doing about it? Since you’ve been talking about depression, I’m wondering what your intent has been. To normalize it? I’m also curious about what kind of feedback you get.

Ryan: Well, if I talk about it, I talk about it at the very beginning. It makes people pay attention, and it’s a good way to get people to listen to you, right? I used to be self conscious about it. Where I would say, “Oh I don’t want to tell my story and try to make a big deal about it.” And a friend gave me advice. He was like, “You lived through this. Why would you hide it? You’re not trying to like cash in on this.” My bigger ambition is to actually give dedicated talks to wellness, mental wellness, and burnout, and developing more of a playbook for people, because that’s something I didn’t have. That’s something that no one talked about. My family didn’t get it. People from all over my life. I stopped being friends with people because of it. I had to fire my friends. There are people I don’t see anymore who I’ve spent a lot of time with, because they weren’t there for me. Some of them were intentionally not there, because their assumption was that if you’re depressed, you’re weak, right? And you can’t talk about it because you’re weak. Like with the guys that I was friends with, and often in business with, there’s a bravado that comes with masculinity. But I feel like leadership is changing. Where empathy, which is a word that gets thrown out a lot, is a prerequisite for leading. But we still have, I think, a huge portion of people, maybe 20–30%, who lead organizations that firmly disagree with that. And they think it’s weakness to admit fault, or to apologize, or to understand what the other person is going through. However, I feel like a lot of the success that I’ve had recently is processing all that and understanding that that’s where your strength lies.

Sara: Absolutely. I want to get back to the playbook you mentioned. Part of the reason I write and think about this stuff a lot is because I had to figure everything out on my own. I think a lot of people that suffer from mental health issues are in the same boat. Where you just grabbed a thread somewhere and started pulling yourself in the right direction, but there was not a lot of help along the way. So, I’m curious to know a little bit more about what’s in your playbook that you talk about.

Ryan: Yeah. You make it up as you go, right? There are always big books about how to build a company and make a lot of money, which is a lot of bullshit, because wealth doesn’t make you happy, and depression often catches up with people in their 40s or 50s. The only positive I had is that I started dealing with it in my 20s. That was the only positive I could muster from it. And my therapists reiterated it. So, I feel like one of the first things that helped me was realizing that’s it’s never too late, and it’s better to deal with it now, and putting it off is the worst thing you can do. And the second thing was firing my friends. Just getting rid of negative people that you know in your heart are not helping you, but that you feel loyal to. You’ve been through a lot of shit together, you’ve had fun at some point, you think you can get it back. But you can’t always, and you have to move on. And then the third is that I think you have to find some sort of meditative practice. I don’t mean you necessarily have to do yoga. But having a routine around your physical health. And it’s hard. You’re lethargic. You don’t want to leave the house. We’re not talking about a bad mood, we’re talking like chronic depression. Yoga was helpful for me. The routine of stand up comedy, knowing I was gonna get out of my house on Wednesdays to do an open mic. Setting up routines and habits and adding structure and order to what feels like extreme disorder, is another thing that I recall. Professionally you’re gonna be not at your full capacity, so if you can take care of your body hopefully you can correct some of that.

Ryan: So I ended up doing a talk at Google. I realized I needed to get my story out there for myself, because I needed to make sense of it. I didn’t know how to professionally talk about it. I was depressed, I was a comedian, and there was a gap in my resume. Like what do you say to people? And so, I just told a bunch of strangers at Google. I created this vivid image of a time I remember so clearly. I had comedy notecards all over my desk and I had dishes stacked for weeks in the kitchen. My linens were on the floor. I didn’t make my bed for months at a time. And when I say that to people, it’s all I need to do. It’s like I can get it out of the way. I feel like making sense of ourselves is so important because you trick yourself into thinking how terrible things were. But now you look at me, years later, and I’m married and have two wonderful children. I do public speaking. That stand up comedy experience was incredibly helpful. I deal with a lot of crazy business people and so being able to help myself get through depression was helpful. And I’m finally able to share the message now.

Sara: On that note, I was just talking to a much younger associate who’s also dealt with depression. I was telling her that I wish I’d heard more people talking about depression when I was her age, because it would have made me feel less alone.

And you know, you and I are about the same age, and have had pretty successful careers, so I think there’s a certain amount of confidence to talk about it. Like, “OK, I might get some blowback from coming out of the closet, or maybe some people may not want to work with me,” but that’s a little bit of a risk I personally am willing to take because I’m far enough along in my career. Have you sensed any results from talking about it?

Ryan: I’ve had bad results and good results. The good results are from the people who reach out to me. I’ve done Skypes before with people. Like, “Oh that meant a lot to me when you did that episode about depression.” I interviewed this guy Brad Feld who’s a big investor at Techstars, and he talked about his mental health issues, and I got a lot of feedback from that. I wrote about it in my book. People will come up to me and say, “Hey, I was divorced two years ago and I totally get it. It was awful.” And so that’s good. Conversation is good. It’s a start. And you know, really it’s listening. Like that’s the next phase and I think that’s harder.

But to your point, I think there’s a general awareness [of mental health issues], or lack thereof, and that’s where the conversation starters are. But really it’s listening. Because I think if you can’t listen and then have some sort of meaningful conversation about it, then just putting it on someone’s radar doesn’t matter. Because people just move on. We’re so inundated with news, or social media, or texting, or other distractions. Being present is so hard. So yeah, awareness is important and then listening and having some sort of meaningful conversation is the next step. And I think that’s where putting it out there matters to people.

Ryan: When Anthony Bourdain and Kate Spade passed away I was just like, “fuck.” I cried when Robin Williams died. I was so sad for some reason. I missed a call. I was supposed to have a call with someone and I forgot. I was like, “Oh.” And then I told them that a friend had passed away, because I didn’t want to tell them I was crying about Robin Williams. But it felt like he was a friend.

But again, awareness that this is an issue that is affecting a lot of people is just not enough. And so it’s really about listening. I haven’t really told my in depth story, because it’s hard. There’s not a place for it yet. Because people aren’t there, and also, if you hire me to talk at your event, I’m there for a business purpose. But I weave it in to my work. I talk about how you need to tell stories and help advocate for yourself and that everyone needs an underdog story or a tearjerker so they can form an emotional connection with the audience. That’s really how I was able to make sense of it even more professionally. I did a talk last week in Oregon, and I showed a friend in my office here my talk. And I was said, “oh, I can tell the depression story or this other story.” And she was like, “no, this is completely timely. You’ve got to tell the stand up comedy and depression one.”

Sara: Yeah. I had been working on the concept of Tiny Revolutions for about a month when Kate Spade and Anthony Bourdain died. When that happened, I was like, “Alright. It’s time.” I sent out the first edition right after that. I was going through a really bad period of depression and doing all the things to pull myself out of it. And I thought that the project itself might help me pull out of it. But I also was just having a moment of recognition that this is something I’m gonna deal with forever. So maybe committing to something where I am talking about it regularly will keep me engaged in the work of keeping myself healthy in way that I might otherwise not do.

Ryan: Does it do that?

Sara: Yeah. I think so. So far. It’s funny how a project like this will just start evolving even after only a couple months. I’m already like, “What if I start to feel better and I don’t feel like blogging about mental health? Or talking about it.” And like, “What if people that are readers don’t want to hear all the time about this kind of stuff and I’m bringing them down?” In the end I figure it will end up being whatever. But as a starting point, I was just like, “No one is talking about this and it’s bullshit.” Take Anthony Bourdain. He was completely out there in so many ways, and I don’t think people knew at all what he was struggling with.

Ryan: Do you watch the show?

Sara: I have in the past, but I haven’t in a while. Had he talked about it?

Ryan: No, but if you watch the show now. I watched it last night actually, he–

Sara: Can you see signs of it?

Ryan: He drinks excessively.

Sara: Yeah, I was going to see if you wanted to talk about drinking.

Ryan: Yeah, he drinks so much. And it’s like that’s part of the gig. Like he would go out to these cities and drink. He drank with this guy in South Carolina at a restaurant called Husk, and my friend in Charleston was saying that this guy went to rehab and gave away his bourbon collection that was very expensive. And Bourdain drank with him for like three days. That’s stressful to hear.

Sara: Do you drink?

Ryan: I do. I have cut back recently. Mostly because my body and I had acid reflux. And it was an eye opening experience because I realized, “Oh my god.” Alcohol on weeknights I’ve completely eliminated. But then I’ll go out to a work event and I’ll have four drinks, so I’ll have to even it out. It’s a new thing, but I’m finding that the clarity you get from not drinking has been so insightful. I feel so much more in control.

Sara: Yeah, I pretty much stopped drinking a few months ago. And I’ve had a couple here and there, but it really is shocking how much better you feel.

Ryan: It’s amazing. My doctor friend really helped me put it all together. Drinking is a great way to mask pain.

Sara: Exactly. When I was younger I used to drink a ton. But in the last few years, I’ve found I just can’t. Even stopping just the cumulative five-or-so drinks a week recently has been really helpful, depression wise. I used to think that if I get back to 100% then I will drink a little bit more, but I don’t know anymore. You do look at someone like Anthony Bourdain and you’re like how much was that completely just like completely fucking with him? Just the amount. The level. Alcohol is a depressant.

Ryan: Oh yeah. And it was mostly my body was telling me it was bad.

Sara: Yeah. Me too. My body was just like, “Stop.”

Ryan: It was just like not even my mind or my hangovers didn’t bother me if I had them. It was just– and so what’s interesting about that problem was that it was a habit. It was almost like a ritual. I went home, I have like a kid screaming at me, won’t go to bed. Its nine o’clock. I’ll have a second beer. I had to stop the habit of wanting to get the beer. And now I just don’t buy it. If it’s not there, you don’t drink it.