Welcome to Daring To, a podcast that finds out how CEOs and entrepreneurs navigate today’s business world – the conventions they’re breaking, the challenges they’ve faced and the decisions that they’ve made, and lastly, just what makes them different.
Bob Tinker is a 3-time entrepreneur. Most recently, Bob was founding CEO of mobile security company, MobileIron, from 2008 to 2016. He led MobileIron from 3 people and initial idea to over 12,000 enterprise customers and $150M of revenue, and an IPO in 2014. During the five-year period from 2009-2013 MobileIron was named the fastest growing technology company in the world and ranked #1 in Deloitte’s Fast 500 Index.
Inspired by the question, “What do you wish you could tell yourself 15 years ago as a newbie entrepreneur?”, Bob recently co-authored the book series, Survival to Thrival: The Enterprise Startup Guide. The book is #1 on Google search for “Enterprise Startup Book”. Bob’s 2nd book — Change or Be Changed — was just released in late 2019.
[Personal trivia: Bob grew up in the midwest, and lived in Silicon Valley for over 20 yrs. He collects Onomatopoeias from different languages, is obsessed with fruit trees, and has an oddly good muppet voice.]
Connect with Bob on LinkedIn and follow Survival to Thrival on LinkedIn.
Show Transcript
Intro: [00:00:02] Welcome to Daring To, a podcast that finds out how CEOs and entrepreneurs navigate today’s business world, the conventions they’re breaking, the challenges they faced, and the decisions that they’ve made. And lastly, just what makes them different?
Rita Tehran: [00:00:19] Well, hi, listeners, and welcome to Daring To. And today, joining me on the podcast, I’ve got really interesting guests, I can’t wait to get started talking to Bob Tinker. He is a serial entrepreneur, three-time entrepreneur, had one of the fastest growing technology companies in the world, believe it or not, which was ranked number one by Deloitte in their Fast 500 index. It was a company that was focused on mobile security called MobileIron.
Rita Tehran: [00:00:45] That was the last of one of his ventures, which eventually was IPO, which started with like three people. Can you imagine, three people? And then, it became $150 million company revenue, right? So, I mean, that’s pretty amazing. But that’s not just the first venture that he’s had. He’s been very successful as an entrepreneur. So, we’re going to have lots of questions. He’s had written two books, both of which I have found riveting. One is called Survival to Thrival, and the other is Change or Be Changed. Now, Bob, welcome to the podcast.
Bob Tinker: [00:01:20] Thank you, Rita. Great to be here.
Rita Tehran: [00:01:22] So, listen, let’s dive into it, right? Because I did read-
Bob Tinker: [00:01:26] Yes.
Rita Tehran: [00:01:26] … the book, Changed or Be Changed. And I’m like, “Here’s a guy that is like a serial entrepreneur, a successful entrepreneur, but he describes the entrepreneurial journey in a really interesting way.” You talked about aging the soul that it’s like it can be lonely; that when you first start out, the first thing that you’re really focusing on is making sure that you don’t die as a business. But yet, within that, you also conjure up this amazing view of what it feels like when you grow a company to success and talk about just the amount of self-awareness and personal growth that you get as an entrepreneur.
Rita Tehran: [00:02:13] And that while the journey might be hard, it sounds absolutely exhilarating. So, I kind of juxtaposed all of those emotions and feelings and go, “Wow!” Tell me what it’s like that made you … I mean, it’s probably why you decided to write the book, right? But did you start out as a young kid going, “I’m going to be an entrepreneur. That’s what I’m going to be. I can tell that. Even I think it’s gonna be painful, I’m going to do it anyway.” How did you start?
Bob Tinker: [00:02:44] I love that you used the word juxtaposition because that’s exactly what it’s like to sort of try and get a company off the ground, and build it, and the highs and lows, things that go great, things that go terrible. I would even go as far as to say that sometimes, it feels actually a little more schizophrenic than that. It really does feel very split personality. And in many ways, like starting a company is kind of irrational.
Rita Tehran: [00:03:14] Tell me more. How could it be irrational? All these entrepreneurs that are listening right now going like, “You think? Bob is telling me I’m going to be irrational.”
Bob Tinker: [00:03:22] Usually, what happens is you’ve got a good job somewhere, you’ve been successful, and you’re like, “I’m going to quit that, go start a company that most likely will fail, and I’m going to work my tail off, and it’s going to be awesome and miserable at the same time.” It is kind of an irrational thing to go do. But when you have an idea or just believe that something needs to exist, and you want to go try and build it, you just got to take the leap and go do it.
Bob Tinker: [00:03:58] When Ajay and Suresh, my two co-founders of MobileIron, approached me to join them as CEO in 2007, I was at Cisco. My last company had been bought by Cisco. And I had a great job there, actually. But when I saw the idea that Suresh and Ajay were working on, I had this, “Oh, crap. I got to go do that,” reaction. And I left, vested stock on the table. My Midwestern father executive thought I was crazy leaving. But sometimes, you just gotta go do it. And it’s an irrational act in some ways, but like many great things in life, they often start with somewhat of an irrational act.
Rita Tehran: [00:04:46] What were you most scared about? I mean, obviously, you like leaving all the stock options and the security. So, moving into that role as CEO in a startup is different to being part of a big enterprise organization like Cisco. What was the thing that you’d say, “That kept me up at night”? If there was one thing that was really, “Yeah,” and then you’re like, “Oh, crap,” what was it?
Bob Tinker: [00:05:09] Yeah, the thing I was most scared, I was to rewind back to 2007 when I was jumping into the chair with Suresh and Ajay. The I was most scared of is failing as a first time CEO, failing Ajay and Suresh as my co-founders if I were not to be a good first-time CEO. I’d never been a CEO before. It’s sort of a big job, and it was a big compliment that they’re willing to bring me on board, but I was scared that my biggest fear was actually don’t do a good job as first-time CEO and actually screw up a perfectly good startup opportunity for these guys.
Bob Tinker: [00:05:47] And I actually spent some time trying to figure out how to answer that question. So, I’m actually not sure I’ve ever told this story before, but I’m like probably 40 or something like that. And-
Rita Tehran: [00:06:05] Young. I like that, young.
Bob Tinker: [00:06:07] Yeah, yeah.
Rita Tehran: [00:06:08] Yeah.
Bob Tinker: [00:06:08] I think, it depends on your point of view. Okay.
Rita Tehran: [00:06:09] It’s definitely young in my books.
Bob Tinker: [00:06:13] So, at 40, I’ve been an executive, never been a CEO. And I wanted to figure out, like, if I thought I could do a good job at this and not screw it up. And so, one of the questions I asked myself was, would I be able to actually hire people – more experienced, smarter, better at their jobs than I was? Because I couldn’t. Like then, I actually wouldn’t be a very good CEO, and I would actually be a roadblock for the team. So-
Rita Tehran: [00:06:47] Is that hard though, Bob? Isn’t that hard though, Bob? Don’t you think that people find that hard? As much as they want to, maybe that’s one of the things that leaders find difficult to be in that position where you actually trying to hire and have talent that is better than you, potentially? Do you think CEOs generally find that hard?
Bob Tinker: [00:07:08] Oh, yeah. And look, it’s actually one of the key criteria of the job, right? Because in the beginning, it’s just sort of you and a small team. But eventually, the job shifts to be more like you sort of do the analogy of like superhero analogy. The first CEO job is kind of like Captain America was put in the woods or Wonder Woman was put into the woods. It’s like you in a small team like back in a tree getting punched and getting dirty. But then, the CEO job turns into more like Captain America, The Avengers, where it’s like you and a band of superheroes. And you have to be able to hire grade A superheros who all have better superpowers than you. You need a marketing superhero, product superhero, engineering superhero, a finance superhero. And they better be better at their jobs than you are. Otherwise, you’re not hiring the right person.
Bob Tinker: [00:07:57] So, I think one of the most important criteria for an early and mid-stage CEO is, can they hire people better than them? And candidly, I was worried that I wasn’t far enough along my career that I’d be able to do that. So, I called one of my old colleagues. So, my previous company, he was one of my peer executives. He’s the CFO, and I was the VP of Business Development. His name is Jim Buckley. I called Jim, and I said, “Hey, Jim.” We didn’t talk in like a year. “I have an important question for you. And please be honest because it affects other people.”
Bob Tinker: [00:08:36] And the question was, “Here’s what I’m thinking about doing. I’m worried about not being able to hire strong executives at this point in my career. If I were to go do this, Jim, like, would you ever come work for me someday?” And Jim’s a super seasoned and super senior CFO. And Jim was like, “Yeah, I would.” I was like,”Seriously, Jim. Please tell me because, look, there are people whose careers are on the line here.” He said, “No, yeah. I would.” So, that was one of the ways I went, at least, to try and figure out whether I thought I could hire people with more experience than [inaudible].
Rita Tehran: [00:09:11] It’s a great litmus test, right? Because if people are willing-
Bob Tinker: [00:09:13] Yeah.
Rita Tehran: [00:09:13] … to follow you, then that says, “Hey, look, you’ve got something that they want to be part of,” or “You’ve got some type booty’s that they really believe in,” and all those and more, right? So, that’s a great fellowship litmus test for leaders to ask. It’s a great question to go and actually solicit. It’s asking-
Bob Tinker: [00:09:34] Here’s the fun anecdote there is that six months later, Jim joined as our consulting CFO, and then actually became our full-time CFO. And he and I worked together to build the company from zero to a hundred million.
Rita Tehran: [00:09:48] He made a good decision. There’s a CFO that read that right. And look, it’s interesting as you talk about it. I mean, in Changed or Be Changed. I love that phrase. I use it myself. And it’s the fact that you actually bring to reality what happens with startups, right? That’s sort of when you start out as the three-person company, maybe a two-person company, to then suddenly growing. And with that growth, not only is it company growth that happens, but there’s also growth within the company itself, right, whether it’s the company culture, whether it’s the people, whether it’s-.
Bob Tinker: [00:10:28] Exactly.
Rita Tehran: [00:10:28] … the CEO role. And so, tell us about that because I think that there are some really interesting … I kind of likened it to it’s a plant that’s starting to grow, and you start like, “Look at what I can do. I can grow all these great leaves. And now, I’m growing all these flowers and just flourishing.” But actually, you need a lot around it as well as it grows because things change. So, when do you think the first sort of aha moment comes in for a new CEO where they go, “Actually, it’s not the same as it was when I first took this on. I need to think differently. I need to be different”? And from your own experience, when’s that first sort of, I don’t know, transition if you like?
Bob Tinker: [00:11:13] The first time that hits is at about 50 people in my experience. And the book, Changed or Be Changed, like many things, sort of the inspiration for that was born from a frustration like many things. And what frustrated me, having been a first-time CEO and being in the fortunate position to be part of a company that we grew from zero to a thousand people, is that I don’t feel like I was very well prepared for how the CEO job was going to change as the company changed, right? As we grew from zero to 50, 50 to 150, 150 to 450, 450 to a thousand, the company changed. And as a result, my job as CEO changed. It’s not like I woke up one day with a different title or anything. It’s like I’m still a CEO, but my job’s different. And I didn’t feel like anybody kinda sat me down and said, “Hey, Bob, as your job changes…” I’m sorry, “As your company changes, your job changes. So, therefore, you have to change.” And-
Rita Tehran: [00:12:26] And why would you, right? You are successful. What you were doing was bringing success. Why would you need to change?
Bob Tinker: [00:12:32] Exactly. That’s the irony of it is that what I discovered the hard way is that the very things that actually helped make me successful in sort of the first CEO stage become the very things that sort of hold me back, get my way, and screw things up at the next. And so, to answer your question, like what made me start to realize, “Uh-oh, this is not working,” was I started to fail at things, things stopped working that used to work. Like, it’s kind of weird when all the sudden, you’re like the things that used to work suddenly stopped working. And it’s kind of maddening, actually.
Rita Tehran: [00:13:13] And you go like, “It must be somebody else. It can’t be me, can it? Because, like, look, I started the company. I got it going. So, what else is going on in this environment that is causing this?”
Bob Tinker: [00:13:23] Yes. Sometimes, that’s the reaction, “Okay. Maybe it’s the environment.” I think, one of the more important characteristics of a CEO that is particularly a first timer is a little bit of self-awareness because when something’s not going right, it’s sort of like a parent. Like if your kids are acting out, you can blame it on the kids or, often, you got to kind of look in the mirror and be like, “What am I doing that’s contributing to the situation?” It gets kind of the same thing when you’re a CEO. Something’s not going right with the company. Sometimes, it’s the situation or the team of the company. Sometimes, it’s you. So, you got to look in the mirror and be like, “What am I doing to contribute to this situation?”
Bob Tinker: [00:14:01] And I’ll give you a really specific example. So, when MobileIron got to about 50 people, two things changed that, suddenly, what used to work stopped working. So, the first thing was when we grew from like 45 to 55 people, I felt like we got worse. You think when you add people, you get better, but there’s this weird organizational break point where like 50 people, the human brain loses its ability to track one-to-one connections. And all of a sudden, what used to work sort of organically just started failing. Like, I remember my customer success team and my QA team, it used to organically be able to stay in touch on customer issues. Now, we’re like dropping balls between.
Bob Tinker: [00:14:48] I’m like, “What happened? We actually hired more people. We should be getting better.” The irony was, as we got bigger, like the way we used to behave, and that applied to the team, it also applied to me that that was about when … like, look, and like a lot of founding CEOs in tech, like I was sort of a product customer person. Like I like spending time on product and customers. And I was good at it. And that was what was important in the very beginning of the company is you work with few people because you’re just trying to survive. You’re just trying to find some customers and sort of prove that you have a business that’s worth getting more capital.
Bob Tinker: [00:15:26] But then, once we started winning some early customers and started to grow that I kept spending my time on product and customer stuff, which is fine. But my team – and I give them huge credit for this – basically sat me down and was like, “Hey, Bob, we are not getting from you what we need. Like, we need you to be the CEO of the whole company, not just product stuff and customer stuff.” And that was kind of a wake-up call for me, right that the things that I was gravitating towards because that’s what the company needed and I was good at, I had to change my behavior to be the CEO of the whole company. Like, “What are we doing on go-to market? What are you doing on team? What are we doing on finance?” Like, I needed to be thinking across all the different swim lanes of the business, not just spending time in sort of my comfort zone that I had gotten good at over the last year and a half as we were sort of getting the company off the ground.
Rita Tehran: [00:16:22] So, let me just ask about that. That’s quite brave of your organization to actually confront you with that. There are often sort of-
Bob Tinker: [00:16:30] Yes, it was.
Rita Tehran: [00:16:30] … situations that you wouldn’t find that, even in a small startup, even if they’ve known you for a long time. What do you think it was that-
Bob Tinker: [00:16:40] What enabled that?
Rita Tehran: [00:16:41] Yeah. What was your secret sauce that enabled people to sort of like stare you in the face and go, “Hey, take a look in the mirror. You might not like what you see, but you need to hear this”? What do you think it was?
Bob Tinker: [00:16:56] So, there are two things. One was culture that in the very beginning of getting MobileIron off the ground, we sat down as a team, which is actually the three core founders. The second meeting we had as a team was what type of culture do we want to have as a company? And one of the things that was important to us was a concept we called intellectual honesty, which is, “Hey, celebrate the good, but it’s okay to talk about the bad.” And we had sort of built that into the culture where it’s OK to sort of, you know, put a stinker on the table and say this isn’t working or something’s broken. This is not going well and it’s okay to do that. So, I think, culturally, the team was wired, and we had made it safe to sort of talk about the bad stuff.
Bob Tinker: [00:17:51] The second thing that enabled that conversation and that feedback from the team to me was that I regularly asked my team for feedback on me. I’d be like, “Hey, do you have any feedback for me? What can I be doing better than I’m not doing?” And at first, they’re like, “Yeah, yeah, yeah, whatever. We’re not going to really tell you what we really think.”
Rita Tehran: [00:18:16] They said, “We love you, Bob.”
Bob Tinker: [00:18:16] But, eventually, if you sort of keep asking the question, and they give you feedback, the key is how you react as a CEO and leader, like if you get defensive or trying to…
