He grew his startup to $150M ARR & an IPO. Now he's back for the AI wave. | Bob Tinker, Founder of MobileIron & BlueRock

Bob Tinker (00:00:00) :
It turned out this is one of the more painful lessons I had in finding product market fit, is that finding product market fit does not necessarily mean you unlock growth. Founders have this magic pixie dust. They can get meetings that regular salespeople cannot get. They can say things in meetings that regular salespeople cannot say. They know everything about the products. They can pivot and be, what about this? What about that? What about this? What about this? What about that? Founders have that magic pixie dust, and it is totally not repeatable. Finding product market fit is surfing. You have to find a big wave first. Some sort of big wave of change that your surfboard is riding on and then your product is your surfboard on that wave, and you have to get it on the wave, and sort of time it right. And then you have to make a lot of course adjustments along the way to optimize your way. Otherwise, you are going to keep paddling until you die, or you are going to wipe out and die. Just to give you a sense, if you find product market fit and then nail go to market fit. That is when explosive growth unlocks. We went from winning ten, twenty customers a quarter, which was fine. To at our peak, we were adding four to five hundred.

Previous Guests (00:01:05) :
That's product market fit. Product market fit. Product market fit. I called it the product market fit question. Product market fit. Product market fit. Product market fit. Product market fit. I mean, the name of the show is Product Market Fit.

Pablo Srugo (00:01:18) :
Do you think the Product Market Fit Show, has product market fit? Because if you do, then there's something you just have to do. You have to take out your phone. You have to leave the show five stars. It lets us reach more founders, and it lets us get better guests, thank you. Bob, welcome to the show, man.

Bob Tinker (00:01:34) :
Thank you, glad to be here. Looking forward to it. Product market fit is one of my favorite topics.

Pablo Srugo (00:01:40) :
Well, yeah, we're going to go deep on it. I mean, you started several companies. I mean, the kind of big one, let's say, is MobileIron. Which grew to, I think you said, $120 million, went public, ultimately was kind of taken private. But we're talking about a kind of billion dollar type company. You were there from day one as founder and CEO. And then now you're working on your new venture. Started about three years ago or so, called Blue Rock. So we'll talk about the new thing. But let's go very deep on MobileIron, just because that was, you know, obviously a huge, huge success. When did MobileIron start, and kind of what was maybe just the origin story as a starting point?

Bob Tinker (00:02:21) :
Yeah, so MobileIron started in 2007, very end of 2007, early 2008, and if you remember back then smartphones were brand new, like the Palm Treo. People may not remember that one. The iPhone was brand new. Android was not even born yet. But what we saw was that smartphones were crashing into the enterprise, and it was driving sort of the IT and security organizations absolutely berserk.

Pablo Srugo (00:02:47) :
Is BlackBerry the one that would have been the one to start that?

Bob Tinker (00:02:50) :
BlackBerry is the one that started it and then it became about iPhone, and then about Android. So, yeah, exactly BlackBerry started it and then it just sort of went from there. The funny little part of the origin story on this is we basically teamed up with Apple to effectively kill BlackBerry.

Pablo Srugo (00:03:07) :
Interesting. Well, we'll get deeper on that, but maybe tell me a little bit more about. Okay, so it's like 2007, smartphones are happening. Where are you in this? What are you doing at that time?

Bob Tinker (00:03:17) :
My last company had been bought by Cisco, and I had spent a couple of years at Cisco. And one of my co-founders from Airspace, our previous company. Hopped out to go start looking at smartphones. His name was AJ. He ended up becoming one of my co-founders. One of the things that AJ was absolutely spectacular about, and this is sort of great advice generally for finding product market fit. Is before you write a line of code or raise a dollar of venture capital, go talk to customers. Just go talk to people to understand what the pains are, what's going on in their world that you can help on. AJ spent six months talking to customers before we wrote a line of code or raised a dollar of venture capital, and that allowed us to really point at a problem that was relevant. Point at a problem that wasn't solved, and it's a lot better to go that way than to come up with some cool technology, and then run around trying to figure out who to sell it to. So that would be sort of the first major lesson on product market fit. Start talking to customers.

Pablo Srugo (00:04:21) :
And which customers was he talking to, and about what?

Bob Tinker (00:04:25) :
Yeah, so this is a tricky thing. It's always easy to say, hey, go talk to customers. But how do you actually do that? How do you get people to talk to you? Especially if you're a first time founder. This is super overwhelming. You don't have a network. You don't know who to talk to. A couple of things can work here. One is just use LinkedIn. Just do reach outs on LinkedIn to people with relevant titles and relevant companies and just ask for advice. You'd be surprised. You call up and try and pitch somebody, they're like, oh, leave me alone. But if you're a young founder trying to start a company and you ask somebody, Hey, look, I'm trying to start a company. I'm looking at this space. I'd love to get your advice. You'd be surprised how many people say, sure, I'm happy to help. That was sort of the biggest thing we did then, just call and ask for advice. The other hack that we figured out was looking at other companies. At least in the mobile space then, and look at who are the customers on their press releases, who are the customers on their website, who are the people that are quoted, and just go call them. It just takes legwork, but people are willing to help, particularly if you're a founder just trying to get a company going.

Pablo Srugo (00:05:28) :
Were you specifically asking about security in mobile? Was that a thesis already that you were trying to prove out, or how general was the questioning?

Bob Tinker (00:05:37) :
The questioning started off a little more general than that, which is we had this thesis that smartphones are going to be a big deal. But what was going to be the problem that had the most urgency that needed to be solved first? Was it a management thing? Was it a security thing? An application thing? What was it? And that's where we just spent time asking customers, what's bothering you? What's troubling you? What's in your way with smartphones? One of the themes that came out was, hey, my users are bringing these things into work and hooking them up without me even knowing about it. That became bring your own device, which became a thing that we just all do now, just take it for granted. But in 2007, 2008, that was a new thing. That was something we discovered through talking to these early prospects. Bring your own device was going to be a big trend. The second big trend we found through talking to them was that people wanted to choose their own device. They didn't want to be told, here's your corporate issue, like ThinkPad. People were like, mobile's much more personal. If I want a BlackBerry, I want to choose a BlackBerry. If I want to use an iPhone, I want to choose an iPhone. If I want a Symbian, I want to choose Symbian. That was the other thing we figured out, user choice really mattered.

Pablo Srugo (00:06:45) :
Was that even true in 2000? You could see it in 2010, 2012, but even 2007? You were seeing that people wanted to choose.

Bob Tinker (00:06:52) :
Yeah, think about back then. Even people had personal mobile phones, right? You had a mobile phone in your pocket, might have been a little crappy StarTAC or something.

Pablo Srugo (00:07:00) :
Yeah, it was a Motorola Razr or something like that.

Bob Tinker (00:07:02) :
I used to have a little mobile museum with all the old pre-mobile smartphones and an original G1 in it. But, because mobile was always personal. Smartphones were more an extension of your phone and so I think people just wanted to be able to choose the one they preferred. That was a very hard thing for IT. IT was like, here's your ThinkPad X one. You get the choice of black or black or black. Henry Ford was like, you get a Model T. You get the color you want, as long as it's black, and smartphones just didn't work that way. You could just tell people were thinking about it differently. It wasn't a corporate issue thing. People kept pictures on it. People had music on it. It was different. It was a much more personal thing. We discovered choice was going to matter. The other thing we discovered was that this was just a giant headache for customers. One of our very early customers was a large pharmaceutical firm in Switzerland. We were talking to the IT guy, AJ was talking to him. He said, hey, my executive team wants to use iPhones at work. I told them, no, they're not approved by security. The executive team told me, this is the guy who runs executive IT, "figure out a way to make it happen, or we'll find somebody else to run our executive IT team". That's motivation. That's urgency and so, these conversations with customers, you start to distill out patterns, and these patterns help inform what product you want to build. Who you think the early customers are going to be.

Pablo Srugo (00:08:33) :
Yeah, so maybe pulling on that thread. Because it's true. As you talk to customers, you get a lot of context. You get a lot of trends and kind of high level problems. And then at some point you start to figure out, like you start to hear a certain problem. You're like, Oh, that I could actually solve, right? What was that for you guys?

Bob Tinker (00:08:49) :
So there were a couple of candidates that we came up with and actually, one important point to talk about here is to take really good notes when you're having these meetings. Because it's amazing how they all sort of blur together in your head after a little while. Have your list of ten questions you ask and make sure you take really good notes on it.

Pablo Srugo (00:09:09) :
Fortunately now it's all just AI. Like transcripts, everything.

Bob Tinker (00:09:13) :
We actually had take notes back then.

Pablo Srugo (00:09:15) :
I know, me too. I used to take notes on every single call with founders. Now I get to just talk to them and know that it's all there for reference. But it's crazy how much that's changed.

Bob Tinker (00:09:24) :
Just use Granola and it'll be great.

Pablo Srugo (00:09:25) :
That's right.

Bob Tinker (00:09:26) :
So, you know, we picked out this concept of bring your own device. We thought it was going to be a big deal. Another one is people were going to want to be able to choose different smartphones. There's another thing that sort of popped out, which was cost control. Depending on the age of your audience here. If you remember, when international roaming was a really big deal. People would take smartphones to go to Europe and come home with a $10 thousand data roaming bill. It was freaking people out. That was another thing we discovered, that cost control and international roaming control was a big deal. All of these things were sort of input into trying to figure out what to start with and prioritize. Then you just start asking people to try it, saying, hey, look, if we had a product that could help you on this, would you be willing to try it? Some people are like, no, you're a little crappy startup, we're not going to use your stuff. Other people had enough pain or were willing to try early stuff. That they said yes and those became our teaching customers. We ended up with about fifteen to twenty teaching customers that were just giving us feedback. Of those teaching customers, about fifteen became betas and seven of them became paid customers. Not all of them converted, which is normal but just asking if we had something that could help you with this, would you be willing to try it, was the magic question.

Pablo Srugo (00:10:40) :
But what was that thing that you decided to help them with?

Bob Tinker (00:10:43) :
Ah, where do we start? Yeah, yeah, yeah, sorry. So we decided to start with bring your own device. How do you enable people to choose their own device, get their email on it? Simple as that.

Pablo Srugo (00:10:53) :
What was the before and after, right? People were just kind of doing it, and then when you guys came in. What was the solution that you offered to that problem?

Bob Tinker (00:11:00) :
Yeah, so in the beginning, what happened is people would go into the email. This is early smartphones. Each one had a different crappy email app. Users had to go in and try to configure it. They had to try to figure out how to get their Exchange settings in there. How do you get permission from the IT guy to connect to your ActiveSync Exchange? There was a lot of sausage being made in this. What we did is we built a system that automated that. Users could download the MobileIron app, put their user ID and password in it, and we would automatically set up their email on their phone.

Pablo Srugo (00:11:31) :
It was mainly for Blackberry's, I would assume?

Bob Tinker (00:11:34) :
Actually, we started with Symbian and Windows Phone. Believe it or not.

Pablo Srugo (00:11:37) :
Okay, Windows Phone, man.

Bob Tinker (00:11:40) :
I know, I'm dating ourselves. I think the product market fit lessons here generally apply. Windows Phone.

Pablo Srugo (00:11:45) :
Yes, not so much.

Bob Tinker (00:11:46) :
Died a very quiet, unremarkable death.

Pablo Srugo (00:11:49) :
And the value was, though. I just want to understand, I mean, the end user had value because of lower friction but you're selling to IT. So I assume for IT was a combination of less manual work, or was it actually better security? What was the big value for them?

Bob Tinker (00:12:05) :
So for IT, the value proposition was it was easier because it automated the deployment. The second thing it did is we ensured security was properly set up. Being able to making sure encryption was turned on and that the device wasn't jailbroken. Basic nuts and bolts security stuff. In many ways, mobile was one of the very first intersections of consumer technology and enterprise technology. And trying to figure out how consumer preferences, consumer needs intersected with IT control and IT security. Mobile was really the first example of this. We had to live with one foot in, how to make it easy for users and the other foot in how to give IT and security what they needed.

Pablo Srugo (00:12:49) :
That's an interesting trend. I mean, you think about the consumerization of the enterprise as kind of this big theme in the last. I don't know, let's call it ten years or whatever.

Bob Tinker (00:12:56) :
Mobile was the first.

Pablo Srugo (00:12:57) :
It was the first, right? Yeah, it's interesting. Everything else was kind of bought top down. I mean, this idea that you could buy a credit card and get your team on Slack. As an example, or whatever sort of PLG type startup you could access these days, was just not really a thing back then. Mobile was kind of the first thing that started that.

Bob Tinker (00:13:12) :
It was. It really was. So it was honestly confusing for a lot of enterprise customers because they were used to just dictating what people did. Yeah, one of the recurring themes that I think has sprung out of the mobile wave is just the democratization of IT. That IT decisions are much more democratic, much more user driven. They care much more about users. They care much more about user experience. All the things that we sort of take for granted today of just building a good product. Came out of that rise of the mobile wave and we didn't know it at the time. We were just trying to figure out what problems to solve and make a bunch of customers happy.

Pablo Srugo (00:13:49) :
Tech has just become such a bigger part of work that it would be hard for IT to still be so deterministic and just maybe strong handed, heavy handed. Because I think at some point, an employee who is frustrated by the tools they're using all day might actually leave and work somewhere else.

Bob Tinker (00:14:06) :
Yeah, absolutely. User experience, the rise of user experience came out of the mobile wave, and user choice mattering to IT. Being able to say, what do people actually want to use? If you think about bottoms up sales models like PLG, it's all driven by individual user choice inside enterprises that then accumulate. Another interesting example of this, I would argue, is probably also Salesforce. If you remember the very early days of Salesforce, the way they got in was they effectively had a CRM that salespeople signed up for individually, downloaded their contacts into, and used it to just keep track of their personal pipeline as a salesperson.

Pablo Srugo (00:14:43) :
I didn't realize that. I knew they were the first cloud, but I didn't realize it was actually PLG at the beginning. Interesting.

Bob Tinker (00:14:48) :
And then they went from there and said, hey, does your sales manager actually want to see what's going on across all your sales people's pipeline? And they're like, yeah, I totally want to see that. So that became sort of the top down upsell that layered onto the very beginning. Sales reps just downloaded Salesforce and they didn't download Salesforce. They signed up for Salesforce and user accounts to do a better job managing their pipeline.

Pablo Srugo (00:15:11) :
So you've got these seven customers that have converted to the full product to manage devices. You mentioned that ultimately you layer on other products. Do you start layering on other products, or do you go to market with that bring your own device solution first?

Bob Tinker (00:15:28) :
So I know there's no hard and fast rule for this. I could sort of share what we did. So once you find sort of the early vestiges of product market fit, it's go time. You're like, okay, we found a pain. We built a product for it. Customers seem to be interested in it. So at that point, we said, yeah, we found product market fit and we hired a bunch of salespeople. We said, it's go time. We did not go build a bunch of other products to try and sell that. We said, let's figure out how to make what we've built go, and it turned out this is one of the more painful lessons I had in finding product market fit. Is that finding product market fit does not necessarily mean you unlock growth. So we hired a bunch of salespeople. Our burn rate went up, but our growth actually didn't go up very fast. So as you can imagine, our board was kind of freaked out. Because our burn rate went up and this was a big lesson for me. Is that, it turned out we had not figured out go to market fit yet, which is what happens after product market fit. Go to market fit is how do you build that repeatable recipe to find and win customers over and over again. And make the transition from founder led selling to sales led selling. You have to build a repeatable go to market playbook, so when you hire a new salesperson, you're like, here's what you do. When you hire a new marketing person, you're like, hey, here's how you fit into the go to market playbook.

Pablo Srugo (00:16:42) :
This is kind of a stupid question I'm asking on purpose like this anyways. If you have insane value unlock, wouldn't that effectively sell itself? Yes, you can optimize the go to market over time and you should. But shouldn't you still be able to hire people, throw them in, and they'll still sell the thing? It's just instead of converting forty percent, they convert twenty-five percent, sort of thing. Or why does that break sometimes? In your case, why did it break?

Bob Tinker (00:17:06) :
I suppose sometimes you're lucky enough that you have an insane value unlock that if you have not figured out go to market fit. That happens more in consumer products. Like, you just sort of get zeitgeist in a bottle and it just goes. At least in my experience on enterprise products, that doesn't happen. You have to figure out who's the ICP, you have to figure out what the entry use case is. You have to figure out how to get them to try it. It's a lot of the early part of the sales cycle just to figure out who you're selling to, what's step one, what's step two, what's step three, what's step four.

Pablo Srugo (00:17:39) :
Maybe as a specific question, what were you doing right as a founder. Having closed the customers that you closed, that your first sales hires were not doing? Whether because of them or because you didn't train them. Whatever, but what was that difference?

Bob Tinker (00:17:51) :
So it's actually nothing that the sales team did wrong. It was actually something that I was taking for granted. Founders have this magic pixie dust. They can get meetings that regular salespeople can't get. They can say things in meetings that regular salespeople can't say. They know everything about the products. They can pivot and be like, what about this? What about that? What about this? What about this? What about that? Founders have that magic pixie dust and it's totally, totally not repeatable. That's sort of this big transition from founder led selling to a repeatable sales playbook that anybody can do. It's not anything that the salespeople are doing wrong. It was that I was taking for granted, oh, well, they just have to do what I do and they'll be successful. That's total BS. I've seen a lot of founders say, well, I'm going to fire my salesperson cause they're not just. They're not doing what I do and if I do it, you win deals. That's just not how it works. You have to have that repeatable playbook of what's step one, what's step two, what's step three. You have to have the supporting materials. You have to have the product.

Pablo Srugo (00:18:48) :
But is it just like, and I'm not disagreeing with it. It's just, there are parts of it that are just like, okay, the founder's going to have more passion. The founder's going to know the product better. Those are given, but couldn't a great salesperson learn the product and fake the path? You know what I mean? Why does it really have to break unless you put it into a formula? Do you remember, and we're going really far back. Specific things that you were like, oh, I just did this, and then you realize, oh wow, they actually can't. They just can't do that thing that I did. You know what I mean?

Bob Tinker (00:19:18) :
Yeah, I don't know. It's a fair question.

Pablo Srugo (00:19:22) :
By the way, I'm asking just for context. Building a repeatable sales pattern is a generally accepted thing you have to do. A lot of it, so then it's like, but why? You know what I mean?

Bob Tinker (00:19:30) :
I think it's because if you want to scale, you need to hire people and they need to know what to do. And as you add a salesperson or a marketing person, they need to know what to do, or if you're adding in channel partners, they have to know how to find and win deals. You can't have it just be this diffuse thing that the founder knows how to do this and it's not just about knowing the product. You have to actually have empathy for the customers. What's their situation, what's going on in their world? How do you help them understand your value? How do you deal with competition? There's a whole bunch of stuff in the sales process that, at least in my belief. You need to be able to distill down to one page and if you can't distill it down to one page. You haven't figured out your repeatable playbook. One head of sales I worked with, I asked him for his go to market playbook and he sent me a forty page brain dump of everything he'd ever learned, right? And that's not repeatable either. I think the key thing is how do you get the repeatability? And I don't know, I guess you're right. Maybe there are going to be some cases where you just find such viral usage and explosive growth that you don't need to have a go to market playbook and magic happens. And if that's your company, God bless. Go forth and take advantage of that if you are so fortunate to be that company.

Pablo Srugo (00:20:42) :
Well, I think, you know, and to be fair. I think that's probably true of, you know, especially these days. You're seeing the zero to a hundred million in two years stuff. You're like, as an outsider, did they figure some crazy go to market? That's just, if I just did that, I would sell, or do they have some insane value unlock that I can't. My guess is probably more the latter. They've just really found some crazy unlock that even if you sold the way they sold, you just wouldn't grow zero to a hundred million in two years.

Bob Tinker (00:21:07) :
Yeah, so that's the other thing that we didn't talk about. Is one of the really important things about finding product market fit. There's a great surfing analogy here. Finding product market fit is like surfing. You have to find a big wave first, like some sort of big wave of change that your surfboard is riding on. You know, the change to cloud, the change to mobile, the change to AI, some sort of wave you are riding and then your product is your surfboard on that wave. And you have to get it on the wave, and sort of time it right. Then you have to make a lot of course adjustments along the way to optimize your way. Otherwise, you're going to keep paddling until you die, or you're going to wipe out and die. But there's also an element of a wave that I think you're sort of characterizing as some insane value unlock. A lot of times it's just identifying a big wave and figuring out problems that wave created and solving that problem. Very rarely is it some massive insight of something that nobody else saw that can unlock massive hidden value. Usually it has to do with some wave.

Pablo Srugo (00:22:10) :
That makes sense. I mean, these days, frankly, AI is the wave that's impacting every single industry and a lot of things. If you're first to it and you have the right go to market. Maybe the right industry know-how to just put the thing there and go to market in a good way. You can see this kind of, not to say that it happens all the time, but you could see this insane growth.

Bob Tinker (00:22:28) :
Number one is the pain. You have to identify the pain that comes from the wave. Number two, you have to have a product to be able to solve that pain and then I believe that number three is you need to build a repeatable go to market to be able to capitalize on that.

Pablo Srugo (00:22:39) :
We have tens of thousands of people who have followed the show. Are you one of those people? You want to be a part of the group. You want to be a part of those tens of thousands of followers. So hit the follow button. So walk me through maybe on that third point. What did you do? You hired the people, burn went up, sales growth didn't really go up. What did you do to build a repeatable go to market? What did that look like for you at MobileIron?

Bob Tinker (00:23:01) :
I got lucky on this that I hired a really good VP of sales just after we found product market fit. He diagnosed the problem pretty much immediately. I was like, Bob, you do not have a repeatable playbook. Your team doesn't know how to find and win deals over and over again. And I'll tell you what, how I translated that in my head was, oh, we just need a better PowerPoint pitch. Turns out that was not it at all. It was about step one, who's the customer going after? Step two, how do we engage them? Step three, what do we do to get them to eval the product? Step four, how do we win? That whole step one, two, three, four. Once he built that and put it down on one page. The reps literally pinned it up on the wall over their computers in their cube. It was, what do they say? What do they do? What's the next step? What do they say? What do they do? What's the next step? And once we got that going, that's when the flywheel took off. Just to give you a sense, if you find product market fit and then nail go to market fit. That's when explosive growth unlocks. We went from winning ten, twenty customers a quarter. Which was fine, to at our peak. We were adding four to five hundred.

Pablo Srugo (00:24:11) :
Wow.

Bob Tinker (00:24:12) :
New enterprise customers a quarter.

Pablo Srugo (00:24:15) :
What's an ACV at that point?

Bob Tinker (00:24:17) :
20,000 bucks.

Pablo Srugo (00:24:19) :
Okay, yeah, so 400 will move the needle.

Bob Tinker (00:24:22) :
It was bonkers.

Pablo Srugo (00:24:24) :
Wow.

Bob Tinker (00:24:25) :
And that combination of finding a wave that's a pain, figuring out your product, and then building a repeatable go to market on the back of that. That's when magic happens and honestly, when you feel that kind of momentum. I still get chills thinking about it. It is so much fun when you're in a startup and you feel that kind of momentum start to happen. Your pipeline grows, the conversions go up, the salespeople are totally overwhelmed. Everybody's just losing their minds because they're totally overwhelmed. But it is some of the most fun you will ever have building a startup.

Pablo Srugo (00:24:57) :
Walk me through this. The go to market repeatable playbook to me has always sounded like more science than art and the opposite of finding product market fit. Which is very much more art than science. I could not tell you right now, here's how you find product market fit. I could tell you, hey, here's what others have done. Maybe it'll work for you, maybe it won't and I'm not a VP of sales. So I couldn't tell, but I feel like some solid VP of sales could take any product market fit company and be like, okay, cool. I'm going to do a three month analysis and we'll tell you, this is probably the best playbook given your CV, given your customer type, given your conversion rates, given whatever. Is that true or is there a mystery to it as well?

Bob Tinker (00:25:34) :
It's a little more mechanical in terms of building it, but I will tell you the key thing to get it right is good pattern recognition. Because you have to be able to distill all these signals and noise you're hearing from all these different people, and all these different customers into what is it you do in step one, what is it you do in step two, and what is it you do in step three. And so you really have to be able to distill the essence down to this is what you say and this is what you do, this is what you say and this is what you do. It is a little more mechanical, but the pattern recognition part of it turns out is really hard. I'll tell you one of the things that is often a real challenge at that stage is you get into this kind of battle of the anecdotes. I've got this anecdote for how a customer made a decision over here. I've got this other anecdote for how a customer made a decision over here. You've got all these anecdotes and everybody's sort of battling these anecdotes. What we ended up doing, which we just sort of did by dumb luck, is we did a deal grind. Where we literally locked everybody in a room and went through twenty deals that we had won and twenty deals that we had lost. And we looked at who is the ICP, what was the thing that got them in the door, how far did they get, who is the decision maker, what made them say yes, and then we did that for the ones we lost. And we literally just ground through it. It was a giant pain in the butt. And on one hand, everybody hated it. But on the other hand, once we got to the end, we're like, oh, the pattern started to pop out both on the wins and the losses. And that became sort of the essence of what we distilled into the go to market playbook. Because otherwise you end up in this anecdote competition, which.

Pablo Srugo (00:27:08) :
I love that story and that approach. What were? Do you remember, and again, I know I'm taking you a long time ago, but do you remember some outcomes of that? Okay, as before, or ICP was any of these but now it was that, or before we might do any one of these three things. But then we decided, no, this is the one thing that we need, or this is, we need to have a decision maker, whatever. Some kind of outcome of that deal grind exercise, kind of before and after having a repeatable process.

Bob Tinker (00:27:33) :
So the very first use case that customers were under a lot of pressure to deploy was get secure email onto the smartphones and one of the things we realized is that for customers that believed in device choice, we would win every deal. Because bring your own device was a really big deal, really good at it. If it was a scenario where customers could dictate their users, you would use this device. We didn't win those deals as much because they would be like, "What? Well fine we just going to dictate everybody use BlackBerrys". And so what we realized out of that is one of the things we had to set the table on at the beginning is a device choice is important for your culture, for your employees, for retention. IT just can't dictate and say, "You must use this device." And so that came out as one of the patterns that we needed to work in. The importance of device choice as a strategic and sort of cultural thing for you as an organization. That was an insight that came out of that.

Pablo Srugo (00:28:34) :
That's a good one, and was that more you putting it out front in order to start that and ultimately convince them, or to qualify them out? Very quickly get them to say, "Yeah, yeah, but I don't care about that." And you're like, "Okay, cool. Then this is not, it's not a kind of SQL as far as we're concerned."

Bob Tinker (00:28:52) :
That's a great question. I don't think we decided that it was either a qualifying or call out question. I think we used it as setting the table up front. If you want to be considered a modern IT leader, you wouldn't do it any other way, would you, right? But I don't know, maybe some of the reps did actually qualify out using that. That's fair, they might have actually. The second thing we figured out is that we had to make it about more than email. Because any sort of early product market fit, you need to have what's the problem you're solving right now, but you also need to take them on a journey to some sort of strategic destination that matters to them. Otherwise, they're not going to buy from some small startup that's got a brand new product. I call it the bullhorn. You basically have to give them what's the urgent pain right now, and then you have to take them to a destination that they want to go to. And so, being able to say, "Hey, we can help you get secure email right now. That's the thing you get right now. But hey, if you adopt MobileIron, we enable device choice so your users can choose any device they want. And we can give you an enterprise app store that allows you to deliver a private, curated set of mobile applications to your users. That might not be something you're interested in right now, but trust me, you will be. That's why you need to go with MobileIron." That was sort of the second thing we figured out of that. Is that we needed to have more than just the what's the problem right now. We needed to have the story for what's next.

Pablo Srugo (00:30:09) :
I love that, and especially because it ties into what you were saying earlier. I think founders naturally do that, and they don't even realize that they're doing that. They're so invested in what they're building and the vision of where things are going. That they might increase their conversion by, and I'm not saying you say this is your product, but really it's half of that. I'm saying you tell the whole story about where the world is going, they buy into it and then you say, "Okay, today, we're just solving this piece, but that's where we're going." And as you said, especially with the enterprise, it's like, if I'm going to partner with you, I'm not trying to churn in a year or two, that's just annoying. I want to know that this is going to be worth it for many years to come. And I don't think most reps would do that. Most reps would probably take the product at face value, the pain point at face value, and try to get the close on this product today.

Bob Tinker (00:30:50) :
Yeah, totally. I think you're right. I think that's a really good point and, you know, look. I mean, the path to product market and go to market fit . Go to market fit is a little bit more of a straight line because you're far enough along that you've sort of figured out where you're going. But, you know, it always sounds easy in retrospect, like how you find product market fit. Because you're looking through the rearview mirror. But I can tell you it is not a straight line. We probably had three or four major course adjustments through that period of time and some people call it pivoting. I call them course adjustments. Finding product market fit is more like sailing. You have to sort of tack and jibe your way to the destination.

Pablo Srugo (00:31:27) :
Perfect. So maybe just as a closing piece on the MobileIron story. How fast, once you figured that out? You mentioned growth at a high level, you went from ten to five hundred a quarter but that, I'm sure, was over some period. How fast did you get to a million? How fast did you get to ten? What was that kind of trajectory like?

Bob Tinker (00:31:43) :
Yeah, so we released our very first product in late 2009. We closed our very first customers in early 2010. Our first year, we did a million bucks of ARR. Our second year, we did $5 million. Our third year, we did $25 million. Our fourth year, we did $80 million. And then, yeah, it was nuts. It was honestly a combination of riding on the back of a big tidal wave, which was mobile crashing into the enterprise, and having built a good surfboard and sort of adjusted course a couple of times along the way to be able to figure it out. You know, in many ways, like I said, the path to find product market fit isn't a straight line, but when you get product market fit and nail go to market fit, magic can happen. We were the number one fastest growing company in the Deloitte Fast 500, I think in 2013.

Pablo Srugo (00:32:39) :
Crazy and so then, you know, we'll fast forward to all that. Ultimately, the company goes public and then a few years ago, you started this latest company, Blue Rock. Tell me a little bit about maybe what Blue Rock is and, again, the origin story for that. Why you decided to jump in again?

Bob Tinker (00:32:54) :
Ah, you know, I think if you're a builder, you're always a builder and I just like building stuff. This is now actually my fourth startup. It's called Blue Rock and in many ways, we started very similar. We thought we sensed a big problem and a big pain in the market. And we went to go start a company to go solve it. So Blue Rock is solving for visibility and security for agentic AI workloads. It's a big tidal wave that's forming, that's crashing into the enterprise. It creates a whole set of new problems and solutions that need to be delivered. And if you can build a good surfboard and get on the back of that, you can build a great company.

Pablo Srugo (00:33:33) :
Very similar at a high level from MobileIron. Mobile goes into the enterprise, then MobileIron. Now AI agents go into the enterprise and Blue Rock comes in.

Bob Tinker (00:33:42) :
Yeah, and there's a little bit of a prologue to that story that's useful to mention. Is like a lot of startups, the path to product market fit is never a straight line. At MobileIron, we had a couple course adjustments along the way. We started focusing on selling smartphone security management for Symbian and Windows Phone. Which turned out to be dumb, it really was about the iPhone. So once we figured that out, magic happened. With Blue Rock, the initial focus we had was solving runtime security, because runtime security has just never really been well solved. Well, it turns out that the biggest runtime security problem there is agentic AI workloads. By focusing on that, the course adjustment to go after that has been a game changer for us. Agentic workloads need agentic sandboxes, agentic workloads need visibility and security. Boards are putting a ton of pressure on companies. Developers are adopting agentic workflows. It is just an absolute tidal wave. I think in GitHub there are twenty thousand new MCP servers posted in the last six months. Twenty thousand in six months. It's a big wave.

Pablo Srugo (00:34:54) :
How have you found building in security for AI, given the rate of change, right? Obviously, with mobile, there was a lot of change, but it takes a longer time to put out a new smartphone and build a following like, the iPhone did and Android. This is like all the time things are changing. How has that impacted maybe your road to product market fit?

Bob Tinker (00:35:13) :
That's a good question. It's definitely faster than mobile. It's definitely faster than cloud, but I think once you develop the muscles to be constantly listening. There's the joke in sales, always be closing. The joke as a founder is you need to always be listening. I think that applies just as apropos in building a startup that's trying to solve problems for agentic AI. You just always need to be listening. Probably the hardest part about building a startup in agentic AI land, is there are a lot of elephants lumbering around in this space. You've got the large cloud players, you've got OpenAI and Anthropic, and making sure you're picking a space that is not going to get featured out by one of the big platform guys has been one of the things we've been really paying attention to. Which is how do you solve a problem that is across all the different models? How do you solve a problem that is across all the different clouds? And that's where we came up with the genetic visibility and security solution. Because customers are going to be deploying in multiple clouds and deploying in with multiple models, and there's not going to be any one size fits all type customer out there when it comes to AI. I think it's going to be kind of oddly similar to mobile. That choice is going to matter and so if choice matters, they're going to need an independent platform to do this, and that's where we come in.

Pablo Srugo (00:36:38) :
Perfect. Well, let's stop it there, and I'll ask the three questions we always end on. For MobileIron, when was the point when you felt like you had found true product market fit?

Bob Tinker (00:36:45) :
When we found true product market fit was when my head of sales at the time came in and said, "Bob, we can't keep up with all the leads that are coming in."

Pablo Srugo (00:36:57) :
That's beautiful.

Bob Tinker (00:36:58) :
Yeah, it was. I'll tell you, so I'm going to follow on to that question with, "Hey Bob, how did you know you found go to market fit?" And so, the second part of that story is probably nine months later, my head of sales came in and said, "Bob, my reps can't get to all the deals they see. I am willing to take up my quota as high as it'll go if you let me hire more people." 

Pablo Srugo (00:37:20) :
God.

Bob Tinker (00:37:21) :
And so those are the two formative moments in knowing when I found product market fit and go to market fit.

Pablo Srugo (00:37:27) :
That's beautiful and then, on the opposite front. Was there ever a point, whether it's Blue Rock or MobileIron, where you actually thought things wouldn't work out and maybe the startup would completely fail?

Bob Tinker (00:37:38) :
So in MobileIron, it was actually, ironically, in the beginning. We raised our first round of capital in March 2008. That date, people may recall, was the month that Lehman blew up, the '08 financial crisis happened. So, three weeks after we closed our first round of capital, the market just imploded. Customers froze. Nobody was willing to do anything and so it was actually terrifying to be an early stage company at that time. In many ways, we just got lucky because we had raised our first round of capital right before things blew up and we didn't have anything to build or sell yet. So we spent the downturn talking to customers and building a really good product. Ironically, if you look at where a lot of really great companies get built, they get built on the backs of downturns. That was sort of the MobileIron one. Do you ever hear about the Sequoia Tombstone meeting?

Pablo Srugo (00:38:30) :
I think, yes, I do. I do kind of remember that, but I don't remember exactly what it was. I just remember hearing about it.

Bob Tinker (00:38:36) :
Yeah. So, I don't know. I'd been in the job like three months, four months. We just raised our Series A from Sequoia, and they have a CEO all hands meeting, and they're like, "Show up at Quadras. All CEOs must attend." And I'm like, "Okay, sure. No problem." I go, and everybody else totally freaked out. Because apparently Sequoia never had one of these before and I show up, and Michael Moritz is up there. And there's a big tombstone that says, "RIP Good Times."

Pablo Srugo (00:39:00) :
Crazy.

Bob Tinker (00:39:01) :
Yeah, it became kind of an apocryphal story in Silicon Valley.

Pablo Srugo (00:39:05) :
And so just that last question, what would be your number one piece of advice for an early stage founder looking for product market fit?

Bob Tinker (00:39:13) :
A, B, L. Always be listening. Just always be listening. Founders usually go start companies because they're passionate and they really believe in what they're doing. One of the failure modes that sometimes happens, is you end up spending most of your time pitching and not enough of your time or my time listening. And so, it's the listening, which actually is going to tell you where to zero in, where to focus, where you might be wrong. I'll leave you with the magic question that turned out to be the way we found product market fit at MobileIron and the magic question that led us to find product market fit at Blue Rock. Which is, what else is bothering you? When you're in a meeting with an early customer prospect looking for feedback and you're trying to pitch them on your idea and get feedback. Ask a very open ended question at the end of the meeting. Which is what else is bothering you? That question is what turned us on to go focus into AI at Blue Rock, and that question is what caused us to go focus on iPhone at MobileIron. And the only way we would have got there is if we stopped talking and asked questions and listened. So always be listening.

Pablo Srugo (00:40:17) :
I love that question, because you have to go into these customer conversations with some context and some kind of opinion. But then you risk missing out on a much bigger hill that you didn't explore. So this kind of opens that up, which is awesome. So Bob, thanks so much for jumping on the show, man. It's been awesome to have you here.

Bob Tinker (00:40:34) :
Pablo, pleasure. Thank you.

Pablo Srugo (00:40:36) :
Wow, what an episode. You're probably in awe. You're in absolute shock. You're like, that helped me so much. So guess what? Now it's your turn to help someone else. Share the episode in the WhatsApp group you have with founders. Share it on that Slack channel. Send it to your founder friends and help them out. Trust me, they will love you for it.