52: FIve9 CEO Rowan Trollope- don’t be a bad copy of someone else

What we all crave as humans is authenticity, is the uniqueness and the richness that makes us what we are. We don't want to talk to robots. And it is the unusual parts of other human beings that are so interesting to us and that sort of draw us in.

Hello, hello. What I got to say is the episode today that we have is absolute fire. It's really fun when you you meet somebody that was completely not on your radar, yet after the conversation you feel like you've known this person your whole life and you have so many similar passions and ideas and philosophies that you both share. And so today we have, uh, someone that meets that exact description, uh, Rowan Trollope, the CEO of Five9, which is completely transforming the customer service experience. And surprise, surprise, the tagline on the website is making customer service more human. So I could not think of a better fit for the Business Is Human show. But, uh, we get into a lot of interesting topics. We talk about what is that— what does being human actually mean as a leader in today's world, and how is that different than the past? Rowan shares some incredible stories just about his life, about taking 8,000 calls as a customer service rep at age 18 while I was probably trying to sneak beers in my parents' basement. Um, so just, you know, a really, really fun episode, and I walked away from this conversation jacked up, and I think you will too.

I totally agree. I feel the exact same way. It's like, from the moment that Rowan jumped on the call, you could just tell that he was a guy that was going to tell it like it is. And because of that, like, mantra in the entire, you know, push to be super authentic, it feels like you're joining a basement conversation.

Well, let's get this basement conversation going then. And so enjoy today's episode and we'll, we'll talk soon. Rowan, what's going on, man?

Hey Scott, nice to see you.

Nice to see you, man. I'm fired up for this conversation because I think a lot of times people see the name of the show and it resonates for them for one way or another, but I think The idea of business being human can mean a lot of things for different people. We were talking a little bit about before the show, what does it mean today for leaders in the modern work environment? I thought it would be great if you could tell your story of how you started to think about what it means for you and just your career and how that's evolved as you become a leader of some great companies.

Ian Formigle Yeah, it's interesting because I got my first job, well, basically my first job in tech anyways, when I was 18. It was then a startup and we became a large security software company, Fortune 500 tech company over the years. Eventually, I got promoted up the ranks and I ended up as the number 2 at the company. I had a chief of staff who went to law school at NYU and She started editing my emails and she looked at one of my emails and she said, "Gosh, this doesn't sound very presidential. We need to rewrite it." I was like, what did I know? I was still in my mid-30s and was very impressionable, frankly. I thought, well, then let me hear what you think it should sound like. She sent me a draft and it sounded like from the desk of, from the office of the the president of the blah, blah, blah, blah, blah. It was so unrelatable. It reminded me back, my grandfather, whose name was Peter, he fought in World War II. One of the stories that he told and that I remember the most about him is that the officers didn't used to eat with the enlisted men in the Royal Navy. It was a clear separation in those days. He would always be the one to basically say, "Screw that. I'm going to go sit with the enlisted folks. We're all part of the same team." This whole separation of officers and troops just didn't make any sense to him. He was kind of outcast a little bit by the rest of the officers who just viewed this as a kind of a clear breach in protocol and norms. But as I started to work in business and build my own career, this whole idea of there's some sort of strange separation between management and leadership and the employees, That was clearly an idea that had carried forward all the way from my grandfather's days up into modern times. It just didn't make any sense to me. And it was like one reflection of that was my chief of staff wanting to send this very formalized email. So I ended up basically saying no, and I would peck out my own emails and, "Hey team," very casual language, not a lot of pomp and circumstance. That just felt natural to me. But I will say that, you know, there was other aspects of my leadership style that were influenced in a way that were unnatural by the leaders who I looked up to. And so that's something that I think about a lot is how can I really be authentic as a leader and be myself? And when we try to emulate other folks that we've looked up to in our careers, it's always going to be essentially a bad copy of someone else. I think it's best to just start from scratch and say, "Who am I? What do I stand for?" and really just show up as your authentic self, and that's the best way to lead companies.

Trey Lockerbie We're just so conditioned as humans from our experiences, from the people around us, and I think just a lot of our natural behavior comes out of self-preservation and fear avoidance. You know, when you get to the root cause of why people need to stand in a single file line and, uh, type an email a certain way and all these things.

Yeah.

That kind of intellectual curiosity around, am I doing this because it makes me feel good or it makes those around me feel good, or it's true to me, or is this because of what somebody once told me that I should do? And I don't want to be, I don't want to get in trouble. Um, is a really interesting thought exercise.

Yeah, yeah. And it's something that I try to impart to my leaders is, hey, this is probably the hardest thing you're gonna ever do because it's hard, because it's scary. You know, for me, it was scary because I worried, what will people think if they see the real me? You know, will I— will they see that I'm like faking it? Or will they see that, um, I don't really know everything? Or, you know, will this be exposing me in some way? And sort of opening me up to weakness and to attack. And it's taken me a kind of a long time to kind of break through some of those internal inhibitions to be able to be as authentic as I can be in those situations. And so, you know, it is a— it takes courage, you know, it's hard to do.

Yeah. And the irony is, at least I've seen in my life, is like in those scenarios where you are more vulnerable, you know, you're not just showing your best and hiding the rest, you have increased intimacy with people around you.

Absolutely.

People feel more connected and more trustworthy, and when you create an environment of trust, people can do great things.

Absolutely. People always ask me for book recommendations, and one of the books that I recommend, and I got this, I'll give credit where credit is due, I heard about this book from Guy Kawasaki. It's a book called If You Want to Write by Brenda Ueland, and the subhead is A Book About Art, Independence, and Spirit. And this always takes people off guard when I recommend this book because they're expecting me to give some sort of a management or leadership book or Michael Porter's Competitive Strategy, great book. But I say, this is a book to read, and frankly, it's in the first few chapters that I was really inspired because what she talks about, ostensibly it's about writing, but the lessons apply to life. That's why the subheading is what it is. And basically what she said is like, if you're bad writing, and I think this applies to bad leadership, bad management, whatever, is when you are trying to be someone else who you aren't. And humans have this very unique ability to pick up on inauthenticity. If you're trying to emulate someone else, what you are is a bad copy of someone else. What we all crave as humans is authenticity, is the uniqueness and the richness that makes us what we are. We don't want to talk to robots. It is the unusual parts of other human beings that are so interesting to us and that draw us in. And I remember very clearly, I was backstage about to get up and talk in front of 7,000 people. And I had done this quite a number of times. So it wasn't like the first time I talked in front of a large audience, but for some reason I was super nervous backstage. I was sweating. I had shortness of breath and I closed my eyes and I thought, I started like the little meditation to calm myself down. And I thought to myself, What are you so afraid of? What's the worst-case scenario here? I thought to myself, okay, there's one person in the audience, actually he was sitting right in the front row, and he had done all of the speeches for and presentations, or many of the speeches and presentations for Steve Jobs in the past. There was a bunch of other Apple executives there, but this guy in particular. Casual.

Yeah.

I was like, what my fear is that they're going to be judging me. They're going to be looking at me with this critical eye of like, This guy, who does he think he is? Look, he's trying to be flashy or this or that or whatever I was thinking. Then I thought to myself, okay, what's the worst-case scenario? What if they saw the real you? What if you fumble your words and you mess up your slides and you trip when you get on stage? What if it's not perfect? What would happen? And the light bulb went off, was like, oh my God, they will totally connect with you because nobody connects with the robotic, you know, welcome everyone to the 2010, like that just doesn't work. So I said, in fact, the more truthful and honest you are about who you are, the better the connection is going to be. Instantly my heart rate went down, my sweating stopped. I walked out and I was just like, it was like being in my living room chatting with 5 of my best friends. It just was one of the best presentations I'd ever done. Again, it's like, so think about that lesson. We're now obviously not talking to 7,000 people on stage every day, but we're interacting with individuals and we're not always being ourselves. There always is going to be some fear or some insecurity that's affecting your behavior in a way that's not ideal. Seeing what that is and being able to identify it will make you a more authentic leader.

100%, Rowan. And something that I was just thinking about when you were saying that is like greatness, right? Like the polished executive that'll go on and give the best speech of all time, assuming it's like very prepared and what you're expecting in that situation. People can admire that, right? They can admire it, but they won't connect to it. Like you were saying, they will truly connect to your mistakes. And also, if you have that little sleight of hand or you're you're basically making that mistake up front. People also become more interested because they're like, oh wait, this guy just kind of messed up. What is he about to do? How is he about to handle himself? He must be so nervous. So now they're more invested in the situation as well. So yeah, it's just, it's fascinating for sure.

Yeah. Yeah, no, definitely. So I think about these lessons because, you know, look, in my world, you know, I focus on customer service. That's what my business is. And, you know, our mission here at Five9 is to end bad customer service. I actually used to work in customer service and technical support. It's my very first job that I mentioned earlier when I was 18. I have this very clear memory, like the first desk, the first chair, and the first computer that I had. I'll date myself, but it was like a 286. You guys don't even know what that is, but it was an old computer, let's just say. I sat next to— On my left was this guy named Ken Baker. On the right was this guy named Dave Hicks. Ken and Dave were like polar opposites of each other, but they were also best friends. Ken was Mr. Personable. He was like a UCLA football player, I think ex-football player from UCLA. He was gregarious, he was warm, he was funny, he was engaging, he was totally being himself. Then Dave on the right was like looked like me, like a computer nerd, but he knew everything. He knew all the answers to all the questions, but he did not have very good bedside manner. Let's just say that. He was essentially annoyed by all of these telephone calls from customers, and you could tell. So I sat between them and I was like, "Wow, if I could blend both of these people into one human being, that would be the perfect representative." warm, engaging, funny, witting human, but also having all the answers right at hand. What I recognized in that first year of dealing with customer calls, I took 8,000 phone calls from customers, is that the system and the business, because of the margin pressure and everything else, was creating an environment where you couldn't treat people like human beings. You had to treat them like a number. You had to crank through all these phone calls. We've all had this experience. I mean, André, you mentioned a bad customer service experience. I was on the phone yesterday with my cable provider, That's never a good experience. It was a total nightmare. You don't feel like you're treated like a human being. My mission became, make customer service more human, just very simple. Everyone can relate to what that would mean for them. If you're going to have a conversation, I'm not talking to a company, I'm talking to a human being and treat me like a human being. That takes not just nice people, which is certainly part of the equation, but it also takes a ton of technology because no matter how nice you are, if I call up my cable company and they're fumbling around and they can't find my account records or the information is bad, it doesn't matter how good that person is, I'm going to be upset. You need to enable them with technology to provide them all the right information at the right time, give them all the channels where they can communicate with the customer. One of the things that I think about all the time is, think about how we communicate as friends. We typically start with a text message, "Hey, are you around? I was thinking about dinner tonight." Maybe you have a few texts back and forth and you maybe jump on a quick phone call. Maybe you fire off an email. You use all of these channels in a very seamless and natural way. Why can't I talk to a business that way? Why can't I text a business who I'm engaged with, "Hey, you just sent me this product. I don't like it." "Oh, what's the problem?" "Da da da." "Hey, can you jump on a call so we can talk more about it?" "Sure, jump on the call, same person." There's a lot to be learned from how we interact just as human beings. Think about companies should be behaving like human beings too, and I should be able to engage with them like a nice human being and have a great experience. Today, some companies do it really well, many don't, and that's the mission that our company has is to bring that humanity back to customer service.

Trey Lockerbie I love that. I want to dig in here because there is contending forces. And I think about this a lot with technology where a perfect example is, is, hey, we're going to use something that asks you a bunch of questions that's a robot, um, and make you jump through 27 hoops to limit the amount of conversation or actual human resources to fulfill a request. And it's a goddamn nightmare for the consumer. But the business has an incentive of, hey, we don't want to just throw bodies at the problem. We want to make it smarter. We want to kind of allow automation and teleprompters to take care of a lot of these kind of highly mundane things that can be redirected. And so my question for you is like, how should businesses think about balancing that? Because I, I understand both sides and Unfortunately, from the outside perspective, I don't see an amazingly clear way that both people can win in that scenario.

Yeah, well, I will say that historically, that's been true. You essentially, as a business, were forced to trade off customer experience for cost. The biggest expense historically, and even today, in dealing with customer service is people. Businesses globally spend 10 times as much on labor as they do on technology. For every dollar in technology, they spend $10 on labor. We are now at the cusp, however, of a revolution using AI to bring really human experiences through automated systems, ones that I think we would all enjoy using. This is the ultimate acid test is like, If I'm going to talk to your bot on your website, is it a pleasant— would I rather do that in the scenarios where you ask me to do that than talk to a human being? If you can get that equation right, then you can actually deliver a great experience. That hasn't really been possible until just recently. It wasn't until essentially deep learning, the deep learning revolution, which has driven automatic speech recognition, natural language processing and understanding, conversation and dialogue management, all those technologies have actually gotten to the point now, or we're on the cusp of this now, where you can have a pretty good conversation with a computer, get the answers to your routine rote questions out of the way, and not have that be a terrible experience. As long as you marry that with a very, very easy way to get to a human being should you need it, Well, then I think you have the best possible answer. I'll give you a simple example of this. I transferred— I was buying Bitcoin. We were talking about Bitcoin earlier. I was buying some Bitcoin a few years ago, and I transferred some money, and I was transferring money into my— this was with Coinbase, I'll say the name— transferring money into my Coinbase account. It was all fine while I was buying Bitcoin until I decided I was going to buy more Bitcoin. I transferred like I was going to take the original investments, add a couple zeros to it. I was like, I'm going to really make a big investment here, and it didn't show up in my account. Well, all of a sudden, this is a scenario where I'm no longer comfortable talking to a bot about my missing money. I want a human being. Guess what? No can do. Couldn't talk to a human being. Now, I hope they've fixed this by now. Brian Armstrong, if you're listening, I hope you've fixed your problem with when you can't actually talk to someone at your company. I eventually did get a hold of someone. They weren't able to help me, so then even that was even more frustrating. I was totally comfortable. If I was able to talk to a bot and it was able to tell me, "Oh, your money is going to— we see that it's in transit. It's going to show up in your account. There's a 4-hour delay," or whatever, I would have been perfectly fine not talking to a human being. In fact, I would have preferred it. I don't want to have to get on a phone in some situations and have chitchat and blah-de-blah and have the real-timeness of telephones. I would love to be able to have a text experience with a bot if it gives me the answer really quickly. But in some scenarios, I wanna be able to say, that's not the answer I want. And by the way, I'm really nervous and pissed off right now. Please connect me to a human being. And you wanna have that seamless transition. So I think it's possible, but it's only become possible recently.

And you're, and you're talking about, uh, you know, a situation with finances where it's super sensitive and any small little thing can really, really give you a ton of anxiety. Um, and what's crazy about that is that if you're a customer and you need support and it's become such a burden in your mind that getting that support is going to be just such a bad experience, you're, you're very likely to push it off for months at a time. So maybe, maybe not with financial stuff, but with all the other stuff. And guess what? When it comes time to renew, when it comes time to continue the business, it's already been severed. And so I kind of want to like segue this into something else that I've been thinking about a ton. And it's this— it's kind of similar to raising children and the way our society views that, right? It's so important for that to be incredibly valued from a father and a mother perspective. And that's the same thing with customer support, right? Because keep me honest here, but I'm a younger, I'm a younger guy. And, and when I was coming out of college, honestly, I mean, I just wouldn't have considered being a customer support specialist. I'm just being completely frank here. I probably, you know, I relate them to the people that I call when I need help at Amazon, or, or whatever. And I didn't think it was a high, you know, an intellectually stimulating job. I now look at it and I think I'm completely wrong. These are the people that need to be the best problem solvers in your organization. They need to understand the product as well as be human, like you were saying. So curious, like, how are you thinking through this? Um, yeah, idea.

Yeah, that's a great point, Andre. So, and I did this job when I was 18. It was my first job out of high school, actually. I did it for 8 months. I took 8,000 phone calls and I was ready to shoot myself. I was like, "Get me out of here," because every week you would take hundreds of calls and 90% to 95% of them were the same calls you took the week before and the week before and the week before. That leads people to— You can't be a human being and a robot at the same time. You can't be a robot, which is much better at dealing with that kind of stuff, Human beings get bored. I was so fucking bored. I was bored out of my mind answering the same questions over and over again. You become distracted, you become irritable, blahdy blahdy blah. What I recognized at the time was like, if you could just take these problems off of my plate, take the 95% of the repeated boring stuff away and just let me deal with the 5%, it was actually a pretty fascinating job. We were debugging people's computers and doing all kinds of really fascinating troubleshooting, and it was really intellectually stimulating for an 18-year-old kid. So that is the solution here, is you have to have a technology that can handle all of the routine rote stuff in a really human way so that your customers will actually deal with it and not just insist on talking to a human being, and then save the 5% or 10% for the human beings who are going to be much better at these edge cases. In those cases, you can then afford to pay people more because you can save a lot of money by taking all that routine road stuff off the table. Then you can pay people more, you can make it a really nice career advancement in customer service. And so I think that is definitely in our future. At this point, we just recently made an acquisition at Five9 of a company called Inference, which is the market-leading intelligent virtual agent. It's a voicebot that you talk to. It can handle, in a very pleasing way, a lot of routine, common calls. We think most companies could probably identify 5% to 10% of the calls that they can automate. Now, we're not up to 90% yet, but over a decade or two, you could see us getting to that ability to automate everything that's common and routine. That puts human beings into where they really should be. Which is dealing with the edge cases and the messiness and the handholding. One of the examples that I like to give, this actually happened to me, context is extremely important for customers. I had a situation where my TV went out, the internet cable service went out. Every morning, I'm down in my kitchen and I have CNBC on before I go to work. Well, this is when I would go to work. So I've got it in the mornings. Well, one day it stops working. I'm like, "Hey, no big deal." I'm not going to jump on a phone call right away and wait for 20 minutes to get an answer to my question. I just want to fire off a quick text and say like, "Hey, the TV is out. Is it going to be on later?" And if I get an answer within a couple hours, it's fine because I'm going to be at work, blah, blah, blah. If they're like, "Sorry you had this problem, Rowan, but it'll be on later today when you get home and we're very apologetic," that would be totally fine in the context of that scenario. Now, take the exact same problem, which is my cable service is out, but now put it in the context of 2 weekends ago, the Super Bowl. 10 minutes into the scenario, it wasn't that exciting, the Super Bowl, let's be honest. But if I've got friends over and the TV goes out, I am not going to be okay with a text message and 2-hour response time. I want someone on the horn now. I want someone who understands Mr. Trollope loves the Super Bowl. And he's going to be pissed and I'm going to have to calm him down right out of the gate and assure him that his TV is— that we're working as hard as we can to get it on as soon as possible. Think about that, context of the same problem totally transforms the kind of service that you want to deliver. In one case, it's totally fine to be an automated system. In the other case, you absolutely need to have a human being and you need to be way more proactive. That's something that businesses have to think about.

Yeah, I agree. I mean, you know, fundamentally what enables that, in my opinion, and I know you guys feel the same, is giving humans the right information at the right time to make better decisions. That is actually what our business does too, but it's more about the internal applications that drive the customer experience, like your CRM, your support tickets, your, you know, just kind of making all of that at your fingertips, by the way, in the interface that you're already living, which I think To me is another really important thing that businesses need to think about. It's context isn't enough. It's, can I give people context embedded inside of their existing workspace?

Absolutely.

And scenario, because I just, I feel like one of, with software, like the fundamental problem that most, many, many companies have is just adoption. Like people just don't want to learn new things.

It's hard.

I don't want to learn new interface. I don't want to go to another place. That's like, That is a real thing. And so I think, you know, the more and more companies think about like, and it sounds like this is very core to your guys' belief, like, how do I give people superpowers inside of the applications that they already are, that they're familiar with? That's actually kind of where the magic happens.

I couldn't agree more. You know, the thing is, Scott, if a CEO wants to understand their business, go sit with one of your customer service reps and watch what they do and watch what tooling they have. And I guarantee you most people who try this will be horrified, number one, because they're gonna be looking at a, often more than one screen filled with different windows and different interfaces like that came from different decades where they're cut and pasting and driving all kinds of additional cost and complexity for their agents. There's the one thing of, well, what does that do for your customer in terms of creating a poor experience because they're having to wait or the information isn't up to date or current? But also think about what happens for the customer service agent when they experience this. You don't care about this because you're giving me this experience and I'm a proxy for the customer. It's really important if that's what they see subconsciously. As an agent, you're going to be like, "I don't think this business really cares too much about delivering great customer service because you can see it in my screen every day and all the bullshit I have to put up with." Then subconsciously, it's like, "Maybe I don't need to care that much about delivering great customer service to the customers that are calling me because I'm dealing with this stuff." It's really important that the interface you put in front of the agents is just as beautiful as what you would put in front of your customers, right? Because if you don't do that, they're going to get the idea that they're not important. And if you, by the way, stuff them in the basement or offshore them here or there, or you, you know, try and jam their schedules in a way that is unnatural, you're going to have the same effect. So you have to think about the end-to-end effect of all of these things.

Hey, André from Troops here. Are you using Slack or Microsoft Teams? Top teams at your organization? If you are, then you have to be delivering the right information to the right people at the right time from your CRM, marketing automation, support, sales engagement, and customer success systems in an actionable way with Troops.ai. But don't just take my word for it. Listen to what our customers are saying about their experience using Troops.

It's a huge coaching tool because most of the time the deals push or stages go in the wrong direction, we can kind of do a postmortem and see where our process wasn't followed adequately. But most of the time, it's a coaching opportunity for the individual and in turn the team.

One of the things that I've been thinking a lot about, so as you know, you know, we actually survey a lot of the executives that we have on here. And one of the questions that we ask is, is what's your competitive advantage? And the number 2 thing that has been cited by a landslide, it's kind of product features and then brand. And when we talk about brand, I think another thing I've been thinking a lot about, like your brand, yeah, it's what's on your website, but it's also every single person at the company and how they present themselves to the market. Like you have all these people, they're out there, they're talking to customers, they're talking to their fielding tickets, doing all of that. They're talking to prospective hires. Like that's arguably more of a force multiplier for your brand than anything else. And so, you know, a marketing funnel that I just don't think a lot of people talk as much about is the internal marketing and the internal employee experience. Because as you said, like if the work experience for your employees is a shit show and they're frustrated and they feel like crap because they're not empowered to do great work, work with the tools or training or whatever it is, then they're going to just show up in a way that you're not excited about to the people that you're trying to impress.

I couldn't agree more. It's not only that, but it kind of brings us back to the title of the show, Business Is Human. That's going to show up in how leadership treats the employees. Go back to the example I used earlier of the formalized email and the impersonal nature of it. Well, it's like if that's their experience with their company, what do you think your employees are going to emulate? To your customers, impersonalness, lack of humanity. Some of the tools that I use to drive this throughout the organization, because I totally agree with you on all of your employees are your best, essentially live and are your brand, is I have an Ask Me Anything channel on Slack, for example, 24/7. If somebody wants to ask me a question, I will answer it instantly. If you're a frontline employee, dealing with our customers and customer service, the idea that, oh, wow, the CEO is actually listening. I could ask a question and he's going to answer me. We're all on one team. There's no weird hierarchy or bullshit. That sets the right emotional tone for them to then deal with customers. That it's like, hey, this place is really human. It's really likable. I can be likable to the customers that are calling me.

I love that. It's a great parallel to the story. I mean, frankly, I think about the way that we're doing that exercise, which is we have like a form submission and then we kind of do the AMAs like in a town hall on a monthly basis. But if I think about the parallel story to your grandfather in the army, really kind of like leading from the front and being in the trenches at lunch or whatever, you know, that kind of more real-time dialogue and availability and transparency is much more akin to the personal, like, we are in it together vibe and feeling and texture of a culture that I think we both espouse and want to be. So that's an awesome tip, man. I love that you guys do that.

Yeah, you know, it's another one that I heard recently, and it's something that I used to do, but Elon Musk was recently talking on, I think it was on Clubhouse, and he basically said like, He would sleep on the factory floor, but the reason he would sleep on the factory floor is so that the employees would see he was there with them. Whether he was up all night or not was less relevant. It was more important that, hey, they actually need to see you at the frontline with the employees and dealing with the stuff that they're dealing with. I think it's really critical that you, as you think about from a leadership perspective, you're not just thinking about doing the right thing, you're making sure that people can see that you're doing the right thing. Otherwise, how are they going to know? You know, the people don't know and they're not used to it, by the way. You know, they're used to a lack of transparency. So when you're radically transparent and you make sure that you're visible in front of employees, it makes a real, makes a real difference.

Not, not to mention something that's kind of underrated. And maybe, you know, maybe this is just my perspective, but I do think it is a big problem if the majority of your organization has no idea what the CEO is doing. And it goes back to what you were saying, right? It's like, maybe, you know, traditionally, it's none of your business, right? Like, don't ask. But at this point, right, especially if you're joining a startup, and you're buying into a big vision, you know, it makes a humongous difference to just get little breadcrumbs.

I couldn't agree more. Every week, I do an email to my employees. And it's, again, straight from the heart. It's not written by a lawyer. It often has typos. It's done fairly quickly because I do it every week on Sunday night, Monday morning, usually. Some weeks I miss, but almost always I do it. And I include personal details. My weekend update, I'll always include how I'm feeling, what happened in my life. And just yesterday— No, 2 days ago, I walked out of my door. I live in San Francisco. I walked out of my door and someone was walking by and they said, "Hi, Rowan." I was like, "Oh, hello." I was uncomfortable because I didn't recognize them. I had actually never met them. Well, it turns out it was a Five9 employee. My dog comes running out and she's like, "Oh, that must be Molly," because I've written about my dog Molly on my email and about my kids and about my life. She actually told me this. She said, "The fact that you share these details about your personal life make a really big difference to my life here and working at Five9. She was a little bit older and she was like, "It's the best experience I've ever had because everyone is down to earth." I'll tell you, there are some downsides. It's not easy to do, but employees really like seeing that managers and leaders, again, it's back to that same theme, are human beings. Why not share that information if it if it makes a difference for employees to see that the leaders are human beings. Nick Mehta does this. I think he was on your show also. Nick and I are long-term friends, and we've talked about this a lot, about sharing more personal details and being very accessible to employees is really, really critical.

Yeah, I love how Nick isn't shy about his calendar. If he has a go for a jog in the middle of the day or whatever, like it's on there. Um, you know, there's not, there's, there's not the hiding. Um, the other, the other CEO that we've had on here that I think does something similar is Goedert Abel from G2, um, who, who does actually a video weekly where he, he, he does a video to the company about kind of like updates and what's going on and I think it's a very, very powerful practice. And so I love hearing these kind of like tactical tips and you're right. I even think about, I mean, I even think about podcasting and marketing and like the people, the authors and stuff that I look up to. And I think one of the marketing lessons that I've learned, and me and André, we like love geeking out about marketing and sales and all that kind of stuff. But like people come for the content, they stay for the person. And so like a great example is like, I, you know, for a long time really liked Tim Ferriss and I love like the Tax and Tips. But what I really was like, it was like, like, what's this dude's morning routine? You know, like, what's his love life like? Like, you want to kind of get those like juicy details. Yeah. And I think it's very easy for us to look at pop culture and understand that dynamic and concept, but we don't really think about it for like, hey, we are actually, as a leader of a company, kind of a similar spotlight visibility. And we actually have an op— you know, people want to know this stuff, people are curious, and we actually have an opportunity to kind of just further be vulnerable and develop, um, give people windows into the world and things that they're curious about.

You know, one of the things that I did early on in my career— I actually worked at Cisco for a while I ran a multi-billion-dollar business, so we had hundreds of thousands of business customers. It was a $4 billion business at the time. In my first keynote address to our customers at one of our conferences, the last slide— I did my own slides— at the last slide, I put my cell number and I said, "If you're having a problem, text me." This was so out of bounds for the norm at that time, Like, oh my God. And I remember somebody was like, you are crazy. You are going to receive so many messages, so many calls. Like, it's going to be out there. And it's like, this is going to be a disaster. Totally the opposite. I didn't actually get that many phone calls or text messages. I did get some, and I got to connect with some incredible people who I never would have known, who, who, you know, were able to bring incredible perspectives that I as a leader was not hearing. You know, managers were Not telling me the full truth, turns out, shock. Just by being that open and transparent, obviously it sent a message to people like, "Wow, okay, this isn't just dealing with this giant Fortune 500 company. This is an individual. He just gave me his mobile phone number." Wow, so like, "Okay, if I buy that product, who am I? I'm just one small business, but now I can actually relate to that person because they're open to engaging." and so on. So I think all those kinds of things add up. That was obviously a marketing tactic, but it worked and it was genuine and authentic. So highly encourage that kind of stuff.

Yeah, and I love that story. And you're really hitting on a point that's super top of mind for me right now. And it's this idea that if you write, you're condensing and really understanding your own thoughts. You're clarifying your own thought loops. When you have that writing down and it's very authentic and you share it, what you're doing is you're slowly chipping away at that voice in your head that says, what if they judge me? So over time you're chipping away at that. So now you're kind of like self-confident and, and, and, you know, on your own path to authenticity and originality. Once you're there, what you find is that you have been cheating yourself out of fantastic conversations at scale. Because the minute you continue that cadence, the amount of people that you realize that are in your community that feel the exact same things that you're feeling, and because you just started and posed that question, are now interacting with you in ways you couldn't have imagined possible. You realize, whoa, there's so much more to life, right? You just have to set that frequency and wait for people to come.

The interesting thing, and I think this is the— like, because we're all violently agreeing, but one of the things that's hard about this is I found this hard to do earlier in my career. As you have more and more success, it becomes easier because you're no longer dependent on— you've made enough money or you're stable enough in your life, or you're less at the whim of others. It becomes easier to do this. So I think the trick is, and you want to create an organization where people can feel that level of psychological safety to truly be themselves. Because I remember back to, again, the first job I had, I was worried every year about getting laid off because every year they were doing layoffs. By the way, nobody ever knew why. It was just people are getting fired or that team was cut or this. By the way, at the time, I really needed the job. I needed the money. I had a baby and a wife at home. I was fucking 19 years old living in a shitty little apartment in Woodland Hills. I was like, "I really need this job and I got to keep my head down and not stand out because the last thing I want is to get my ass laid off and not have a paycheck anymore with a family to support." So in that environment where the company wasn't necessarily supportive of bringing your whole self to work, that wasn't demonstrated by the leadership. I wasn't going to stand out.

Yeah.

I wasn't going to be myself. What I now realize later in life is like, okay, it's one thing to give that advice to people, but they're not going to follow it if they're working in an oppressive environment. So you as a leader have to create the environment that promotes that sort of psychological safety where people can do that. And you have to be transparent about things. Like, for example, we never knew why people were getting laid off, probably because someone in HR or legal said, The company can't do that. We have to hide all those details and so on. I think what's been so great about so many companies in the last 10 years is they've been challenging those things. Like you mentioned, like a CEO publishing their schedule or what have you. I think it's really, really critical that we have that level of transparency. That's really important to creating psychological safety and that will create an environment, like that plus the leaders modeling the right behavior. Where people can actually take this advice and execute on it. The only thing I would say to anyone who's listening is if you're not working in a company where you feel that level of safety, where you feel like you can do that, go find another company. There's plenty of companies out there that will provide that kind of environment, A, and B, if you're in a leadership role, A, you probably don't even know what it's really like to work in your own company, so go sit down with the front lines and actually watch what their experiences are. And see if you can start to drive it in the direction of the kind of environment where you would want to work, where you could bring your full self to the office, you know, every day at an earlier point in your career before you had the sort of ability to, you know, be yourself all the time and blah, blah, blah.

I love the idea of, of like almost thinking about like, go do like a user experience, user experience project of your employee experience. Like go and sit in and see these people's day-to-day, what it looks like. You know, it's almost like, you know, effectively as a leader, you're the product manager of your company. And so treat it like that, like treat, you know, go do the user experience research.

That's great advice. I like that one.

You know, I hate to be the bearer of bad news, but this is sounding a lot like Undercover Boss.

I can see the one-way glass of the employees.

Sally, I know you and your husband haven't been on a vacation in 20 years. That's why I bought you a ticket to the Bahamas. But anyway, Rowan, it's time to find out the things that make us stay. Uh, and by that I mean your morning routine.

Uh, I usually wake up way too early. This morning I woke up at 4, uh, 4 or 5. Um, first I try and get myself to go back to sleep. Uh, and then when that doesn't work, I get up. First thing I do is I make coffee. Well, actually, the very first thing before I even get out of bed is I get my phone. I know this is bad, but I do. And I check things like Twitter and email and this and that. But then later, I make my coffee, and I will do 15 to 30 minutes of meditation. This is in the morning. I have 2 little kids at home. So once they get up, everything's like— and the dog is awake— everything is impossible. In those early hours, I do meditation. That's why I do 15 or 30 minutes, depending on how much my head is in it. And then I will— this morning, I watched YouTube videos on little hobbies that I have that I'm doing. I like to play piano, but I don't do that in the morning because it'll wake everyone up. But yeah, I'll pursue my own little things. I don't typically get right into work. And then by 8 o'clock, 7:30, my kids get up, I take them to school. School, and then I come back and I start my day.

Awesome. And I'm glad that this is segueing nicely. I could tell that you're a guy that has a couple of various amounts of hobbies. What is the hobby right now that's kind of been the white elephant, right? It's one that you've always wanted to do, but you're trying to find the right amount of time to pursue.

Well, my sort of biggest hobby over the last, I'd say, 10 years has been mountaineering. And so I've been training So right now, mostly it's training. Like, I'm just doing endurance training. But high-altitude mountaineering has been something that I— this year I wanted to climb Denali, Mount McKinley in Alaska, but, you know, because of COVID it's not going to happen. So next year I'll do it. I was also supposed to do a big ski tour in Austria. So that's my thing, is ski mountaineering. I like it because it's got skiing, which I love. It's got going uphill, which I don't love, but it keeps me in shape. Uh, and it's got gear, which I also love. I'm a big nerd. So like any gear-heavy sports, I— that get me out of my office and outside, I really, really like.

And to end the show here, this is the last one on my side. Um, before we started the recording, you mentioned, uh, a story about a bet you made with a friend about Bitcoin. And I, you know, I just want you guys— if you feel comfortable, I want you to share with the audience because I love Bitcoin and all things cryptocurrency.

So Yeah. I was fishing in Alaska with my buddy, Rob Lloyd, and Rob and I, I was explaining Bitcoin to him. This was about 8 years ago, 7 years ago. I mean, it was less than $10 or $50. I don't know what it was, but it wasn't very expensive. I think it was $3 actually at the time. I explained the whole thing and he was like, "This is never going to go anywhere. The government's going to step in. It's all bullshit." I said, "No, no, no, it is." He goes, "Well, let's make a wager. I bet you 1 Bitcoin that it won't go anywhere. It'll be gone in 3 years." I said, "I'll take your bet." Sometime later, it was worth $18,000. Now, it's $51,000 today, but $18,000, I called in the bet, and he was surprised to hear from me. He said, "All right. Well, I'll tell you what, let's donate it to charity," which we did. That was my bet. It was a terrible bet on his point to bet me 1 Bitcoin. I was, it was a win-win for me, but he really didn't think it was going to go anywhere. And all I can say is I wish I would have bought more.

Join the club. Uh, who doesn't feel like that, but it's all good.

Um, I wish I bought more at $30,000, which was just like 3 weeks ago. I was going to do it too. I was like, I was talking to my financial advisor. I was like, let's buy some more. And now here it is at $50,000.

So you got to just do the auto, auto buy monthly and just not even think about it. That's what I do. Um, but anyways, uh, Rowan, this was, this was fun, man. This was really, really fun. I had a blast on this conversation and so many, I think so many important topics for, for leaders. Uh, and so thank you so much for coming on. We, we really had a blast and, you know, I think a lot of people out here, they probably want to just keep up with you. And are you big on Twitter? You mentioned Twitter. Are you, you a tweeter or are you a LinkedIn guy?

No, I'm not on LinkedIn really that much. I'm on Twitter @RowanTrollope.

Love it.

Awesome.

Well, thanks everybody for listening to the show today. We're, we're super grateful. If you liked it, share it with a friend, give us a 5-star, all the things. And, uh, we look forward to seeing everybody on the next show.

Awesome. Thanks, Scott. Thanks, Andre.