Most CEOs get fired for missing numbers. Bob Tinker did something different—he fired himself.
After taking MobileIron from zero to $150M ARR and going public on NASDAQ, Tinker faced every CEO's nightmare in 2016: missing numbers and losing half the company's market cap. In that painful board meeting, he made a decision that would surprise everyone—including himself. "Hey, one of the things we should talk about is whether I should be the CEO of MobileIron going forward," he told his board. Sixty days later, they took him up on it.
What happens when a successful founder-CEO steps down? In this candid conversation with StormVentures' TaeHea Nahm, Tinker reveals the brutal lessons about **when to change people who were once great, how to unlearn what made you successful, and why the hardest CEO decisions aren't about strategy—they're about loyalty**.
Watch the full interview now on EO's YouTube channel! Below is the complete transcription of the interview. Minor edits have been made for clarity and readability.
Key Highlights:

"The one thing that allowed us to really unlock growth was building a repeatable go to market playbook from how we find customers, engage customers, get them on board, make them successful. That one go-to-market playbook got us from probably 0 to $20 million."
"Interestingly, what I found is the way you know is you feel it, you feel the momentum. It's a blast."
"In 2016, we missed our numbers. We lost like half of our market capitalization. It was really painful. And as CEO that responsibility was on me in that board meeting. I said, hey, one of the things we should talk about is whether I should be the CEO of MobileIron going forward."
"What was hard for Bob is changing great people. What I mean by that is if you have someone who just struggles, it's easy to say, you know that person's struggling, we gotta make a change. But what happens if you have someone who did a fantastic job but because the company grew, the job changed and that person's not changing."
"If the people aren't willing to change, you have to change the people. So as a result, some of your leaders and execs will make the leap. The other thing that happens is sometimes your execs or leaders either won't or can't make that leap, and you have to let them go, and that's hard."
The Hardest Thing About Being CEO: Changing Great People
Can you tell us about your experience building MobileIron from startup to IPO?
Bob Tinker: My name is Bob Tinker. I am a multi-time entrepreneur. Probably the one I'm most well known for is being the founding CEO of a company called MobileIron, which we started in 2008 and grew from 0 to $150 million of ARR over the course of 5 years and took it public on NASDAQ.
So in 2014 we went public. In 2016, we missed our numbers. We lost like half of our market capitalization. It was really painful. And as CEO that responsibility was on me in that board meeting. I said, hey, one of the things we should talk about is whether I should be the CEO of MobileIron going forward. And then probably 60 days later, Tahi came back to me and said, you know, remember that conversation we had in the board meeting? We're going to take you up on that.
From your perspective as board member, what made that CEO transition necessary?
TaeHea Nahm: Bob is so gifted, he can compensate for a lot of people, and he was doing a lot himself, but what was really needed was to replace some of his executives, and that was a hard decision for him. There are a lot of things that Bob, because he's so talented, can change easily. So if it's anything related to him personally, he can internalize it and knows how to change.
For example, how you manage someone in the beginning of a company, you have to micromanage every detail as CEO of the company and so he's very good at that because he's smart. But at the same time as the company grows, then he's good at delegating and just managing, setting goals and metrics. So he made that transition very easily, which many founder CEOs have a hard time transitioning, you know, how to give up control.
What was hard for Bob is changing great people. What I mean by that is if you have someone who just struggles, it's easy to say, you know that person's struggling, we gotta make a change. But what happens if you have someone who did a fantastic job but because the company grew, the job changed and that person's not changing, so the person was a superhero yesterday but is struggling today and there it's hard to change because you feel so much loyalty for that person and so that is an emotionally tough decision to do is to change people that were great that are struggling today.
From Burnout to Teaching: Why Entrepreneurs Write Books
What did you do after stepping down from MobileIron?
Bob Tinker: After I stepped aside from running MobileIron, like a lot of entrepreneurs, after a run like that, I was tired. I took some time off. That helped. But interestingly, I also wanted to teach. Like there was a lot of things I learned in my time at MobileIron that I wanted to share, and there was also some things about sort of my experience in being an early stage CEO that were frustrating that inspired me and Tahi to write two books.
I had two big frustrations in being an entrepreneur. The first frustration was I felt like companies go through stages where things change. I was always struggling to sort of understand what's next because as CEO you're always working on what's happening right now, but you also have to be looking over the hill to figure out what's next and how do you make sure you get to that next stage, and I didn't really feel like there's any good content out there or investors are really good at helping me on that.
The second thing that was a big frustration was this gap between product market fit and unlocking growth. I was mad that nobody told me about how do you solve for that. They're like, get the product market fit and hire salespeople and go. I was like, that didn't work, and I was mad being able to use that frustration. And what we learned from that about repeatable go to market playbook to unlock growth and finding go to market fit, that was sort of the second frustration.
The third frustration, which is that as the company changes, your job changes, so the people have to change. The thing that surprised me on that was how hard it is to unlearn. We spend most of our time learning, learning, learning, learning, learning, learning. It's really important, but one of the things we don't talk about is what do we need to unlearn. That was a big lesson for me.

The VP of Sales Evolution: From Explorer to Eisenhower
Can you give us a specific example of how roles need to change as companies grow?
Bob Tinker: I'll give you a specific example. Let's take VP of sales. So in the beginning, ideal VP of sales that you need is someone who's like a pioneer or an explorer, someone that can find a path through the wilderness, you know, to the promised land. The person that can survive with no map, doesn't need a lot of supplies, is not worried about Indians, hostile. But we'll find that path through the wilderness. So as an explorer type person, and usually that person's good at managing a couple of sales reps and so forth.
As soon as you find that path through the wilderness, you don't want someone that's a pioneer type leader. Instead, what you want is you want someone like Mel Gibson in Braveheart. You want a warrior leader. You want now to go down this path like 50 warriors that will go and fight against the bigger enemy, the bigger competitors, and win deals.
But once you have like 50, 100 warriors and you're growing, the kind of VP of sales you want is not a warrior leader, but someone who is good at managing warrior leaders. That kind of profile is someone like Dwight Eisenhower. Dwight Eisenhower was the commander of the Allied forces in World War II on the Western Front, so he commanded the US Army, the British Army, Canadian Army, French Army, on the Western Front. But it turns out he never fought in battle. He was never a warrior, but he was very good at managing warrior leaders.
And so if you hired a Dwight Eisenhower at the beginning with two sales reps, it would be a total disaster because that person's trying to build structure, process think like a big company when you don't even have a path through the wilderness. And so this is what I mean by at the company is at different stages you need different skill sets. It's about how to prevent someone from being a superstar today and being fired tomorrow.

The 90-Day Rule: When to Let Great People Go
How do you help teams navigate through these change points?
Bob Tinker: Yeah, some tips for sort of unlearning and helping teams navigate through these change points. The first thing is recognizing when one of your leaders is going through one of these change points where they have to unlearn their old role and learn their new role. The second thing, and this is really hard, is sometimes people don't want to unlearn. They're actually just really good at their job and they want to keep doing their old job. And the problem is you as the leader, you're like, well, actually I need you to do the next job, but they're not willing to unlearn, you know, as the company changes, their job changes. So the people have to change to adapt to their job, and if not, you have to change the people, and that's hard. If the people aren't willing to change, you have to change the people.
So as a result, some of your leaders and execs will make the leap. The other thing that happens is sometimes your execs or leaders either won't or can't make that leap, and you have to let them go, and that's hard. Because you have these leaders that have been a big part of your company in helping make it become the company it's become, so you feel super loyal to them, and you want to give them a chance to make it to the next level. But at some point if they're not able to, you have to let them go, and that's hard.
The trick on this is how much time do you give them, and this is tricky for a CEO because a CEO. There's sort of a damned if you do, damned if you don't, because if you take action too quickly and let them go too quickly, you're not willing to work with them, not willing to let them learn, and you're kind of a jerk. If you take too long to let them figure it out, you're weak and you don't make decisions. So there's sort of a damned if you do, damned if you don't. My experience on this is you have about 90 days to give a leader a chance to step up and unlearn their old role and learn their new role, otherwise you have to make the change.
It's hard. You have to be respectful of the executive. Thank them for what they did, be really appreciative, give them an honorable exit, but the reality is sometimes, the best thing for them is to go do their role again somewhere else, and it's one of the great things about Silicon Valley and entrepreneurial communities is sometimes there are people that are really great VPs of sales from 0 to 50 million, and having them try and be the VP of sales from 50 to 150 million, they just don't want to do that job. It's a different job. So the best thing for them to do is to leave and go be the VP sales somewhere else from 0 to 50 million.
What about the leaders who are willing to make the transition?
Bob Tinker: Now the second category is people who are willing to unlearn and learn, and it's spectacular if you have a leader that's willing to do that. Some of the most fun you'll ever have as an exec is working with one of your leaders that's able to make this leap. The first piece of advice on it is let them know this change is happening. Your job is going through a change, and therefore you have to change. The second thing is get them a good mentor because having them talk with other leaders like themselves that have been through this change is super helpful to them to be able to get feedback from the outside to kind of know what to look for and how to change and how to think about it.
The third piece of advice on this is help them know what the new job looks like and what the things are that they need to do and to have a conversation with them about what are the things are that need to change and being explicit about that helps them understand what needs to change, but also so it helps create a really nice powerful relationship between you and that leader who's making the leap because being able to make those step functions for your unlearning and learning is typically a step function in somebody's career. By being able to do that, they've earned the right to play at the next level. That's really fun when you see somebody able to do that. It doesn't mean they're always capable of doing it, but it's really fun when you get a chance to see them do that.

From Captain America to Professor Xavier: The CEO Evolution
How does the CEO role itself need to evolve as the company grows?
Bob Tinker: So in the beginning of the company when the company's up to like 20-25 people, the best founder CEO is like Captain America, someone who goes out there, leads by example, fights everything, so the ideal founder CEO in the morning is talking to customers, in the afternoon is telling engineers what code to write, and the evening is writing code himself or herself. So it's just right there with the people. It's great inspirational leadership, fast decision making, everything is aligned and it just works very well. So the ideal CEO profile is Captain America.
As the company gets bigger, you can't maintain that structure because the founder has too much control. Soon we will grow beyond the founder. And so the next type of profile is you want a founder who's good at leading a band of Avengers. So you want each VP to have superpower that's even more powerful than the CEO. And so you want the VP of marketing to be a better marketer than the CEO. You want the VP of sales to be a better salesperson than the CEO. And so you want a CEO then to lead a band of Avengers rather than being Captain America. And so to do that, it's about how you delegate but still maintain control. In the first phase it's about managing tasks. That's what a Captain America will do. The next phase is about setting the right goals, watching the right metrics to make sure that you can empower people, but you can still have accountability and visibility.
Then as the company gets even bigger, what you want as the CEO who's like Professor Xavier in X-Men and you're building a school of superheroes so that you know it's not just your executives but a broader team of emerging superheroes throughout the organization and do that vision and culture become very important because for the CEO to set goals for everyone means you undercut the hierarchy. The CEO then can take leadership with the vision and culture and to make it grow even bigger. So this is what we talk about how the CEO role changes and if you try to have it be Professor Xavier on day one, then the company will struggle.

The Saturday Morning Problem: CEO Mental Health
What did you learn about the personal challenges of being a CEO?
Bob Tinker: So being a CEO is a tough job. The CEO is always making decisions. Some decisions are easy. Some decisions are hard. Some decisions you have no idea what the right answer is, and you just have to pick something. The other thing about being CEO is it's exhausting. I learned a couple of interesting things about just being a CEO and what it means for you personally.
The first thing is that it's a fascinating exercise in self-awareness to be able to look at yourself in the mirror and be like, what am I doing well? What am I not doing well? Like. It's a fascinating exercise in that. The second thing is that it's really hard to draw boundaries in your life because I call it the Saturday morning problem. You have 4 hours on a Saturday morning. How do you spend it? Do you spend it hanging out with your family, hanging out with friends, doing the things you want to do personally, or do you spend it on helping make the company better because there's 900 families that are depending on the company. That creates a low grade stress for you as a CEO.
The third thing I learned is that being a good CEO requires a level of sort of schizophrenia because on one hand, you need to be super optimistic and be an inspiring leader to point people at the mountain and be like, let's climb that mountain together, but on the other hand, you also need to be kind of paranoid, looking over your shoulder at all the things that could go wrong and solving issues that are happening every day.
When I add it all up and sort of look at it, the ability to be part of building a company that makes a difference for customers, that creates value for shareholders, you get to bring a great team together, you get to see them grow and learn, like there's a lot of crap that happens and a lot of hard stuff. My advice for CEOs is be able to zoom out because I found like when I was in the soup bowl, sort of just dealing with all the day to day stuff, it always seemed like there's all sorts of issues and stuff like that going on. But when I zoomed out and looked at where were we a year ago and where are we now, and I'm like, oh my God, look at all the progress we've made, like that filled up my gas tank and gave me energy.
Everybody will have their own sort of personal things they do to stay mentally healthy. Some people exercise, some people sleep, some people socialize, you know, everybody's gonna have sort of their own routines for it. So I don't have a specific recommendation on that, but have a routine, whatever it is. The thing for me that helped, I guess, give me balance was spending time with family and friends. I'm an extrovert. I'm wired as an extrovert, so I get energy from that. So being able to spend time with my wife and kids and be able to spend time with my family is how I recharged myself.
You know, I look back on sort of my journey as a first-time CEO. It was crazy. It was hard, it was exhausting, but it was also a blast. Got to be part of building a great business, got to learn a ton about myself, and I don't know this for sure or not, but I think what I learned on the journey actually made me a better person.

Writing Together: When Founder and Investor See Different Movies
Tell us about the experience of writing books together as founder and investor.
TaeHea Nahm: So when we started writing the books, Bob and I, we thought it was going to take 6 months, not 4 years. It took us that long to reconcile our view of working on MobileIron and airspace. So even though we worked closely together on those two companies, it looked like we were watching two different movies. And so reconciling our two views, took 4 years. At the same time, we felt that the reconciliation would help.
And what I mean by that is that one view is like the founder CEO is like the surfer who's like in the water riding the wave and the surfer's number one goal is don't wipe out versus the investor board member, me who's like in a helicopter above this surfer and maybe 20 surfers but not in the water and sort of watching and saying this is where the wave is going and trying to give direction and so reconciling the founder I mean the board member, investor and the founder CEO took 4 years.
Three Core Pieces of Advice for Future Entrepreneurs
What are your key pieces of advice for future entrepreneurs?
Bob Tinker: I think I have sort of 3 core pieces of advice for future entrepreneurs. The first one is start with a pain or problem, not a technology, because customers buy because of pain and problems or gain. The second big thing is figure out your own personal way to unlearn. Everybody sort of can figure out their own way to unlearn, but in order for you to be successful, you're gonna have to figure out how to unlearn what made you successful and learn what's next. You're just gonna have to figure that out for yourself.
Third thing is do your best to surround yourself with good people, both in your work life that you want to spend time with and in your personal life, because at the end of the day, the thing I am most proud of and the thing that I look back on and I remember the most is sort of the people that I worked with and the customers we made a difference with and the relationships I built. Now I'm now, how old am I now? 53. Yeah, I think you've, at least how I'm sort of evaluating my success in life is not my balance sheet or my checkbook. It's actually the relationships I have that mean something to me.
What are your plans for the future?
Bob Tinker: So plans for the future, on the work side, I started a small private equity shop called Metamorph where we buy small software companies and help make them better. So on that point we're looking to buy one or two companies and help make them better, and we're looking to make the companies we already bought even better.
On the personal side, my wife and I are recent empty nesters, which is sort of an English term for when your kids leave home to go to university. I'm looking forward to visiting my kids at university and, being able to spend some time with my wife and my friends because, it's kind of wild to feel like you're just don't have kids anymore and, you get a chance to spend time with your friends and wife in a way that I haven't in 20 years. So that's my plan. Not super exciting, but for me, very satisfying.