Keith Grossman on Failure and Resilience
TIME President Keith Grossman rose to media prominence from his start as an intern at Condé Nast to critical roles at WIRED, Portfolio and Bloomberg. Now, he’s focused on evolving the storied TIME brand for the next decade. In this conversation with Daniella, Keith talks about what he learned early in his career about layoffs, how he navigated a challenging boss, why he thinks business is always personal, and more.
Daniella Pierson: Keith Grossman, you are one of the most successful leaders in the media world. You are the president of TIME. Could you explain more about what you do every day, then also the numerous jobs that you had before this prestigious job at such a young age?
Keith Grossman: So I interned in college at Condé Nast, at first in consumer marketing and then at WIRED. My first job out of college was at WIRED as an assistant and I rose through Condé Nast and spent most of my time at WIRED. I spent a little bit of my time working on the launch of a brand called Portfolio. Then I went over to Bloomberg and from there I ended up ultimately at TIME. The reason that I came to TIME was—TIME has been under many different owners over the past few years. First it was Time Inc., then it went to Meredith, and then Marc and Lynne Benioff bought the brand. And TIME exists as a private asset. When I was brought in the challenge that they were faced with was, “How do we take this brand, this storied brand that everyone knows, that's been around for 100 years and how do we preserve that red border, the objectivity of TIME, the trust of TIME for the 100 years? For a very long time we were looking at the technology perspective, we were looking at the marketing, we were looking at the products and we were starting to just build out a lot of muscle on the brand. And you know, it was neglected. It was really just this beautiful treasure of a brand that was neglected for probably about 10 years.
2020 came around and we had to evolve very quickly. I always joke that the philosopher Mike Tyson has this quote, “Everyone has a plan until they get punched in the mouth,” right? The original plan was pre-2020 on how to evolve the TIME brand but then in 2020 we realized we had to evolve it slightly differently. We focused on things like TIME for Kids to make sure that we could get TIME for Kids into everyone's hands at home. We worked on things like personal finance and health initiatives. But then coming out of 2020 I started to get really personally fascinated with Web3 and it took me down a rabbit hole that I have not yet escaped from nor do I want to escape from that I absolutely love, which is the next evolution of where the internet is going. Over the course of this past year I've been transitioning out of my responsibilities of overseeing all of TIME’s businesses into a focus on TIME’s Web3 strategy and evolution.
DP: That's amazing. I was going to ask you about Web3 because you are very vocal about your interests there and it is very exciting that such an established brand is doing this instead of a newer media company. How old were you, by the way, when you became the president of TIME?
KG: I was 39 when I became the president of TIME.
DP: That's very young. We were just talking before we hit record and you said that you've always been the youngest person in the room. I can definitely identify with that. What were your first few jobs? How did you make yourself so valuable that you were able to become a president of an organization like TIME? Can you walk us through that journey and any feelings that you had along the way?
KG: I've been very blessed in that I've worked very hard and I've gotten a lot of opportunities throughout my career to take advantage and be able to move up. I've never actually told this story publicly but for the topic of this I think it is fair, so… When I started at WIRED, it was 2002. I was ignorant enough that I didn't realize I was entering into a brand post the dot-com crash and that everyone was super vulnerable.
I had three bosses and I really loved two of them, I'll get to the third one in a second. I had a day on January 7 (I think it was 2003) where I got a call from one of my bosses that I loved, hysterical crying. He said, “Can you come down to the office and help me? I need to see you.” It was like 10 at night. And I said, “OK.” I thought, in my sort of ignorance, that we were going to go out and celebrate my birthday. Here I am, 22 turning 23, and I'm super selfish and thinking about only myself and it hasn't hit me that going from college to the real world is setting yet. I got down to the office and I saw him in the office hysterical crying—what he needed help with was packing his desk up. I didn't understand why he was let go. He should not have been let go in my opinion. To this day I still speak to the managers there, who are amazing individuals. But like I said, I just still can't understand.
That was my wake up call very quickly that the real world was not college, that you were not guaranteed to continue to always move forward. I walked away that night so upset emotionally, personally weirdly deflated. I was disappointed in myself thinking that it was all about me, going out to a party and to celebrate my birthday. But I walked away saying, “I'm never going to put myself in a position where I could get fired, ever” What I realized was: to ensure that I had to always work the hardest, I had to always be the biggest team player that I could be, I had to always add value to the organization in every capacity. I also came to a big realization that the whole premise of work-life balance is a very individual, sort of emotional decision and that there's no one formula. If you want all the success and all that comes with it professionally, you have to give up life. If you want all the freedom and all that comes with that personally, you give up work. If you want that perfect balance, you only rise so far, right? Take you, for instance. People will look at you and they'll see the Forbes article and they'll think, She has it all. But what they don't see is—Saturdays, all your friends are out and you're working; Sundays, all your friends are out and you're working; Friday evening, you can't even think by 7 p.m. This is my life, right?
I had that moment and I had that realization like, Wow, I have to put myself in a situation that I can't be dismissed so easily. The other thing I learned… This is why I said that I had three bosses and one I did not personally care for. One day the one that I did not care for, who was really just mean to everyone, called me down to a room and decided that she was going to attack me both personally and professionally. She didn't like something and she was so mean that I stood up to quit because I was seething. I was 22 or 23 at the time. One of the other bosses that I really love heard through the grapevine that she did this to me. He wasn't in the office and he said, “Before you do anything rash, walk around the block three times and wait for me in the lobby and I'll be back there for you in a second.” And he came right back to the office and he met me in the lobby. I was about to quit, like leave media altogether. He met me down in the lobby and he calmed me down and he convinced me not to quit.
DP: That's so powerful. Thank you so much for sharing those stories that you haven't shared before because I feel that a lot of people, not just in media but in corporate structures, can identify with everything that you're saying. By being so young and having to stand up for yourself, I think what I really pulled out of the second story was that you were upset and you were going to make a decision (again, a lot of people think you can't have emotions in business) but the person that you looked up to, your boss, instead of him saying, “Put everything down” or whatever, his advice was, “Just walk around the block. Have your mind reset and get grounded. The feelings are OK and valid, but let's make sure that you're making the right decision for yourself.” That's so important. I feel that many people do not have somebody that would've said that. They probably would've said, “Oh, he's too emotional. Good riddance anyways.” Going back to the person who wasn't so kind to you, do you know why the person felt that they had to be a bully or be somebody that would affect other people's mental health in a negative way?
KG: I don't know why. I don't think that this person was a nice person at their core to begin with. The unfortunate reality that people have to come to grips with, when you all of a sudden move into the real world from college and then start to build your professional career, is that ultimately almost nobody cares about you or your success except for maybe a few family members, maybe a few friends, maybe a few people that you come across in your career. Other than that, most people (sadly enough) go through their professional careers thinking solely about themselves and think that it's a zero-sum game. I heard a quote from Warren Buffett that I loved more than anything else and I think is a really important quote, it shaped a lot of who I am today from hearing it. I would ask people to think about this. This is how I try to operate today and how I've tried to, for many years, operate. Everyone sees the world through the lens that they know, right? He says, “Love is the only commodity you can’t hoard. The more you hold onto it, the less you have. But the more you actually give away, the more you get in return.” If you operate your professional career with intelligence and focus and in a notion of giving away love, constantly pushing it out as opposed to trying to hoard it, it pays back in spades.
DP: I love that business analogy. Going off of that, how many people report to you?
KG: All of the different jobs have been so different. Bloomberg was a few hundred. TIME, as an organization, is about 325 or so. I think Bloomberg actually was a little bit bigger. WIRED was smaller. The one thing that you should never confuse is—once you get beyond 20 people or so it doesn't matter, because what really matters is making sure that your direct reports are incredible and you can trust them and that you can delegate to them. There's a level where you could do it all yourself. But once your company gets too big, there's no difference between 30 and 400.
DP: Yes. Because you just have the key stakeholders and leaders reporting directly to you and trust that all of the organizational structure beneath them is perfect and people are getting feedback. I asked that question because I want to know, based on that experience and any other experiences that happened to you in the business world before you had the opportunity to lead an organization, what have you implemented in your leadership style based off of those feelings that you had when you were 22 years old?
KG: People like to say business isn't personal. Like, “This is not personal, it's business.” I actually think business is extraordinarily personal. Pre-COVID I thought it was really important that you always wanted to be present. When you think about the workplace environment pre-COVID, there were really three ways in which an individual existed amongst the other individuals. There was “visible” which is what we are right now. There was “invisible” which is like, I'm not in your mind or in your line of sight, we're not meeting. And there was “present” like—we would be in the same office, I would see you, I'd say hi. That would be it. We'd have a small talk, we'd move on. I think people dismiss how powerful and how important “present” was. What you got post-COVID was the loss of “present” and the emergence of just “visible” or “invisible” and that actually changes people's stylistic approaches quite a bit. Because you can't just smile at someone. You can't just say hi to somebody. You can't just go over and sit down and have an impromptu conversation. It also means that things that are really good that happen in people's lives are good for less time and things that are really bad are stewed on for much longer because emotionally they have no outlets. They are by themselves, isolated.
I think that that reality is something that we are all struggling with to understand how to navigate through and to manage through. And I think that that reality is why you're seeing the great resignation take place. I think that reality is why you're seeing quiet quitting take place. I think that reality is why you're seeing things like the loss of ambition in the workplace emerge. What I try to do is to be as accessible as I can. I try to celebrate, where I can, everyone's victories. I try to model the success where I can. But I'd be lying if I didn't say that it's hard. It's not the same because if you managed through a very human touch, you don't have that as much.
DP: For sure. The human connection piece is so important in business and in mental health, so the fact that that's been lost… You talked before we started recording about how people might see someone like myself or yourself and think, Wow, they have the world at their fingertips. That's why I'm very vocal on social media showing the other side, the realistic side, of what it takes to be successful and how much it really takes from you. Can you speak more on the realities of wanting to be the best in your field or wanting to achieve success and what that has been like with your mental health journey?
KG: Sure. What people see on social media is a pittance of reality. The best or the worst part is that it's only the reality that you want to present or that the individual wants to present. You had a post the other day where you were exhausted, you were hopping on another plane, you had gone through meeting after meeting and you're like, “I could post this picture that showed how great the meeting was but this is a picture of how utterly bone-tired I am.” I joke that one of my best qualities is my impatience. At the same time, the problem with impatience is that it causes you to be extraordinarily anxious when the outcome that you want is not delivered as fast as you know it can be delivered. It opens up a few questions, which is, Can I do it faster? In that case you then worry about, Do I undermine the team and just do it? In that case people start to resent. Or, Do I just sit there and wait and let it happen? That is another sort of scary vulnerability to have.
The other thing I learned—I think that what people don't realize is people see outcome but they don't see intention sometimes. I've launched many things: I launched the WIRED tablet edition, I launched Quicktape at Bloomberg with a few others, and I launched TIMEPieces at TIME. When we launched the WIRED tablet edition, there was a moment where after spending a good portion of the year making sure that everyone was educated on what was going on in the media landscape as it relates to the iPad’s emergence, Steve Jobs passed a rule which said you couldn't use cross compilers to upload your program to the iPad. That meant that the entire digital publishing suite that we were working on with Adobe no longer was valid. I was called into the office and I was told that the WIRED tablet edition was canceled. I had to figure out how we were going to return millions of dollars in advertising sponsorships and I was going to have to inform an entire sales team that the millions of dollars in advertising partnerships that they had sold and that they were all expecting to get paid on, they weren't going to get paid on because we technically never launched the product. So imagine I'm sitting there and I'm like, “Oh my God.” It was the worst feeling on the planet. Then I got a call, luckily, that Adobe could code the entire application in Objective-C and Cocoa and we could be on time. It went on to be one of the most successful launches on the iPad. But those 10 minutes… those 10 minutes were extraordinarily scary to me. That was an emotional rollercoaster that I dealt with by myself.
With Quicktake, it was hard to build a social mobile video network at Bloomberg. I was running the sales for it and we had brought in 20 million dollars, I think it was, of revenue and sales. The product kept on getting delayed because what we were doing was never done before. We delayed it once, then we delayed it a second time. After the second time, all of the partners were like, “Enough!” That was another unbelievably humbling feeling of sitting there being like, “Oh my God, if we delay this one more time we're going to lose 20 million dollars in revenue.T his is really not good.” There's a pit in your stomach that I can't explain to somebody how humbling and vulnerable that feels. You've done everything you can and you're still left like, “Oh my God, because we're trying something great and we're trying something new, people are going to get frustrated.”
I would say the thing that humbled me the most and that probably crushed me the most was the launch of TIMEPieces. I had spent months studying the space and Web3 and asking questions. I had made a bunch of assumptions with the team about what was fair. When you look back, one of the things we wanted to do is we wanted to make sure that if we were selling 1/1 NFTs for hundreds of thousands of dollars, that TIMEPieces was a more affordable way to get into building a community. So we priced the Genesis launch at 0.10 ETH, a tiny amount compared to what the 1/1s were going for. We didn't know or think about gas and bots and all of that stuff. We did this drop. The drop, from a revenue perspective, was so successful—it did about 4.5 million dollars in 45 seconds or something like that. What it did was a complete fail from a consumer perspective. People paid tens of thousands of dollars if not more for pieces that should have only gone for a few hundred dollars. All of a sudden I found myself in a scenario where the organization was celebrating a financial success and I was looking at a community lambasting me online to the point where every day I probably had like 15,000 or 20,000 tweets that said to go kill myself. Things that were just awful.
I'm not a sensitive person at all, I've grown thick skin over the years. But I will tell you that I knew that this was a big miss on our end. There was one night that I was at dinner with my wife where I just said to her, “I'm not insinuating anything but if I have a heart attack or something happens, this is where my life insurance is.” We legitimately had that conversation. The navigation out of it was—ultimately I was very transparent in a very long Twitter thread that explained what went wrong and we did this drop called the Cat Mint Pass. I'm surprised it went away immediately on coming clean to say to people, “This was the intent. This is what happened. This was our mistake. We're sorry and this is how we're gonna do it.” It took four or five months of focus to make sure that the community saw how genuine we were through a commitment to the space. That was the most humbling experience I ever had because the first one with the tablet was individual, the second one was a handful of marketing partners (so it was only at the most 20 people), the third one, which was TIMEPieces, was like thousands of people screaming at the top of their lungs on Twitter. I couldn't even open up my phone without people jumping at me on every device you could imagine, including emails.
We had made a mistake. We had miscalculated demand. We had miscalculated all these things. We did not assume the market properly and it's not sympathetic but what it is a testament that people love to focus on the good, what they don't focus on is the sleepless nights, they don't focus on the stress, they don't focus on the wear, they don't focus on the human toll. I bring that up as an example because I tend to always try to stay positive on social media. I tend to never show emotional vulnerabilities.
DP: I really appreciate your vulnerability, Keith, in telling us those things because it really does seem like people in your position just have it all and they don't think about those sleepless nights where you are responsible for so many people. I hope people in your position are going to be more honest and vulnerable about what the reality is of their jobs and the stresses they go through so that people don't feel alone when they have those same feelings. Thank you so much for being on the podcast.
KG: It was a pleasure. Thank you, Daniella.
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