Selling What They Think Is Free with Eric Appel

Hey, real quick before we get into the conversation. Look, if you've been listening to this podcast for a while now, you know I don't have sponsors. And it's mainly because I know most people, including myself, skip right through them and I just don't want to annoy my audience with 10 minutes of sponsor spots every single week. However, it also means I don't get paid to do this. So the way I help fund my ability to provide free content and really interesting conversations like the one you're about to hear is through my sales training and coaching services. So if you've gotten value out of some of these conversations on this podcast and you're looking to level up your sales game, do me a favor and go to jbarrows.com and check out the training tab on the top nav bar.

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Now let's get on with the show. There is so much happening so fast. If there's something I like about though, the speed right now, what is requiring of organization is to not just move fast, but move fast in a disciplined way. And it is forcing innovation. If you are not innovating every day, you will get left behind. And if you were just following, you will also get left behind. As companies in technology, what we're finding is you can't just follow, you have to find ways to be unique and lead. Hey everyone, welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between. And guess what? I truly respect and I think make a positive impact on the world around us.

Now this week, I'm sitting down with Eric Apple. He's the worldwide head of sales at Island, the company that literally invented the enterprise browser category. He grew up in Waco, Texas, listening to his dad make cold calls on the couch at 730 at night, which is where he caught his first sales bug. And I think it's hysterical. Then went to Texas A&M, started his career at Arthur Anderson right before the Enron disaster. It brought the whole firm down and which, man, talk about dodging a bullet there. And then landed at Yahoo during the dot-com era, where he was part of the team that Mark Cuban built with broadcast.com. And then a happy hour conversation led him to cybersecurity, where he's been for the last 22 years of his career.

Now here's why I think this conversation is so important right now. When Eric started at Island, again, enterprise browser, every single CIO and CISO he walked into said the same thing. We already have Chrome. It's free. Why would I pay for it? Or why would I pay for a browser? And he figured it out. He actually took Island from zero revenue in stealth mode to over 100 million in ARR, and now a $4.8 billion valuation. Now, if that objection sounds familiar, it should. Because right now, the number one thing I'm hearing from almost every sales team I train is, hey, we can do that with AI. Or we can build that ourselves with Claude or GPT. Why would we pay for your software? It's the exact same problem.

The default alternative looks free, and your job is to prove why it's not. So we get into exactly how Eric reframed free into a real budget line item, why he's only hired people he had personally sold with in the early days, and how they built an advisor network to create pipeline, and why showing up to a C-suite meeting without a hypothesis is basically career suicide at this point. Hope you enjoy the conversation as much as I did. Let's make it happen. Eric Apple, welcome to the Make It Happen Monday podcast, my friend. How are you doing today? Fantastic. Thanks for spending time with me. Yeah, thanks for coming on. I was saying this is a really timely conversation, I think, for a lot of the people listening here, because what we're going to ultimately talk about is how to position your solution that a lot of people all see is, well, I can do that, you know, for free or with this other tool or whatever it is, especially now with AI and how creative people are getting with it.

So a lot of the clients I'm working with are struggling trying to sell their product service solution when the perception is that AI can do it so easy. So that's what we're going to ultimately get to. But Eric, as always on these shows, I always like to kind of see where you came from, right? Like what made you you from an entrepreneur standpoint and all that other stuff. So what I couldn't figure out in my prep was like kind of where you grew up, kind of your parents' influence and that type of stuff. And then we'll get into Texas A&M. And then I am very curious about the whole Arthur Anderson Enron thing as your first job, my friend. But let's let's start with the let's start with growing up as a kid, man.

Well, yeah, glad to do it. Born and raised Texan, which used to kind of be the standard in Texas. But now we've welcomed people from all parts of the world that have moved to Texas. But born and raised down in Waco, Texas, very blessed that I had an awesome upbringing. Two amazing parents. One, my dad, I used to lay on the couch at night and listen to him cold call. No way. Back in the day, you know, you called somebody at 730 at night. They answered. Yeah. And so I would sit on this green couch he had in my study and or in his study and I would just listen to him cold call. And that's where I got a knack for for selling. And I just had an awesome upbringing. My mom couldn't couldn't have asked for a better mother.

And then my brother's also an entrepreneur. So he actually developed a company called Big Hat in the spirits industry. And he's doing quite well, made it out of Waco, although I still love to go back and visit and ended up at Texas A&M. So fun. Oh, man. Proud good. Great parents, great brother. Great friendships made along the way. Love that, man. You know, what's funny is I just watched Glenn Gary, Glenn Ross again recently because, right, because I had to remind myself. And, you know, I remember the main scenes and stuff, but I hadn't seen it in a long time. And it opens with them literally making cold calls in a phone booth at a Chinese restaurant at like eight o'clock at night. And the receptionist of the of the Chinese restaurant is their receptionist.

Basically, they go back over to their office. They're like, yeah, tell me if anybody. So like back in the day of making cold calls at seven o'clock at night is just absolutely awesome. And the fact that you were exposed to that is fantastic. So, right. So you got to Texas A&M. And I'm sorry, what was your degree again? What did you end up getting? Business management. Business management. Perfect. So and so then your first real job was was Arthur Anderson. And that was right around the Enron kind of disaster. And so, A, what drove you to go to Arthur Anderson right out of school? Because that's a that's a kind of a big like, OK, cool. I'm in that world. And then what was it like going through the Enron stuff at 20 X years old for you?

And what did you learn from it? Basically, ironically enough, I wanted to be a lawyer because of the movie. A few good men and Tom Cruise in the courtroom. And so I thought I'd be a lawyer, wanted to do it, and then got recruited by Arthur Anderson and came up to Dallas and took me to this bar called Lulu's Bait Shack, which isn't there anymore. We went out, had a blast, had a great time, surrounded by really cool people. And I thought, you know, I think this could be a really cool experience. And then kind of been an about face and did not go to law school, joined Arthur Anderson. And talk about amazing people, amazing culture. Like I remember our first three weeks, we go to this college campus in Chicago, learn more in about three weeks than I probably did in four years.

Nothing against Texas A&M. But man, you learn a lot about business and how to drive the word V value back in the day. In terms of Enron, I, man, I was, I actually had left right before. Good for you. And I will say, super sad. When you think about a company the size of Arthur Anderson at the time, had about 120,000 employees. And really, it was about six people that drove down a company the size of Arthur Anderson. But it lost its integrity at the end of the day. And if you're in audit, integrity is everything. And so it drove it down. So super, super sad. But man, I was blessed that I built some great relationships here. Hey, taking a quick break here to remind you to check out some of my sales training programs at jaybarrows.com and use discount code podcast for 20% off the individual packages.

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Thanks for your support. Now let's get back to the show. So good. So strong, glad you kind of got out of that. But then you jumped into Yahoo. And I mean, we're in the dot-com kind of boom-bust section. I look back at my career and like I graduated in 98, right? So I graduated in 98 and I got into, right? Right into 2000. And that was like the first like, huh, like what's happening here? And like, this is crazy. And then all of a sudden it comes crashing down. It's like, this is a nightmare. And then 2007 hit. That's when my second company started. You know, so like almost every downturn in a market is when I've started a company. And I quite frankly think that's one of the better times, but you were at Yahoo, which was kind of the darling child at the time of, of search and everything and email and all of it.

So what was that ride like? And again, going back to kind of your, your leadership or what you understand about selling value, building value with organizations, what were some of the takeaways from the Yahoo experience and that, that time? Cause it was just bananas and it, and it's very similar to what's going on now. It's just like, just on, you know, steroids now, but that back then it seemed like it was so crazy. I remember in, uh, in the year 2000 and I was standing in the Yahoo lobby for my interview. And I remember looking up and seeing the purple Yahoo letters and I was like, holy shit, I'm 24 years old and I feel like I have arrived. I'm at Yahoo. Um, the, the part of Yahoo that I was joining was actually part of the piece that Mark Cuban, who started broadcast.com, uh, Mark sold broadcast to Yahoo.

And so, uh, he had, you know, the, he invented broadcast.com because of the story goes in 1996, he wanted to listen to Indiana basketball on the internet and there was no way to do it. He couldn't get Indiana basketball and radio in Texas. So he, uh, he started this notion of streaming audio stream. And next thing, you know, he, they started streaming things like Victoria's secrets, uh, uh, launch for the year. And they would get millions of viewers and they started doing corporate communications. And then there's, they started building advertising around it, which is why Yahoo got really interested. and then Yahoo bought broadcast.com for $6 billion. I unfortunately joined after that acquisition.

So I was not, I didn't get to really reap much of the financial benefits, but I will tell you what I learned there was a couple of things. One, the intensity that Mark had brought to that, that culture was something that, that I, that I remember just about, Hey, you, you, when you're at work, you're there to do a purpose and you can do it and have fun, but you're there to drive a purpose but then also it was, it was engaging back with the core Yahoo team and, and, and the things that they were doing just around all the data and user experience that they were collecting. Yes, it was around advertising and things like that, but it was a blend of, of data analytics, user experience. And then that kind of fed into what we were doing at broadcast, but it was a, it was an awesome opportunity and learned a ton.

And then that ultimately actually got me me, you know, got me forward into relationships that he, in a weird way, ended up leading me to information security. Cause my boss at the time, a guy by the name of Jim Lewandowski ended up going to McAfee. And I remember we were doing a happy hour for him. And as he left, he was going to McAfee and I went to the happy hour and he's like, what do you know about security? This is in 2004. And I'm like antivirus. And he was like, yeah. He said, yeah, I think you should, you should meet some people. I think this should be a good ride. And so met some people. And then that started a journey in information security. It started in 2004. And fortunately for me, I'm still in it in That's an interesting ride.

And I think a lot of, I'm curious from your perspective with where we are right now. Right. Cause, cause there's this similar, people are still having the same argument. Well, you know, technology, yeah, it evolves and it displaces jobs, but it also creates jobs. And I keep looking back on it and saying, yeah. Okay. You know, and I was there, right. I was there 2000. I was there with the iPhone. I was, and all those were kind of gradual. They seemed like, Whoa. But I even remember, I mean, you know, I was there with the iPhone. You know, and I was there, right. I was there 2000. I was there with the iPhone. I was, and all those were kind of gradual. They seemed like, Whoa. But I even remember, I mean, you remember back in the internet, it was like, most people thought it was a fad.

Right. So it took a while to adopt and really evolve. And people are saying, well, the same thing here with AI, it's going to change things, but we're going to evolve. I'm having a hard time with that argument though, because it's, it's so much faster now. And it's, and it's evolving at a pace that is, is, is mind numbing in so many ways. So what are some of the things that you're seeing right now that are similar outside of speed, right? The speed of, of, of, of evolution, where we are, what are some of the similarities that you're seeing between the two kind of bubbles, if you will, if you consider us in a, maybe AI bubble, similar to the.com bubble. And what are some of the learning lessons you took from that, that you're applying to what's happening right now?

Great, great question. And, and probably a lot to unpack there. Yeah, you're right. I'll try to leave speed out of it for now, because there is so much happening so fast. And if there's something I like about though, the speed right now, it's, it, what's, what is requiring of organization is to not just move fast, but move fast in a disciplined way. And it is forcing innovation. If you are not innovating every day, you will get left behind. Uh, and if you were just following, you will also get left behind as, as companies in technology, what we're finding is you can't just follow. You have to find ways to find ways to be unique and lead those that are following, um, and clinging on to legacy ways of doing, doing things are going to face a big time challenge.

You know, there's, I kind of look at it. There's a couple of things happening. There's obviously the, the wonderful things that are happening with AI and the companies that are innovating every single day. When you think about open AI, when you think about Anthropic, think about the things that, that others are doing. And then you think about the companies that are empowering that like Nvidia and they're in this kind of this, this area over here that are showing massive growth from a revenue perspective, from a stock performance and all that. Then if you look at the left, you've got traditional software companies and those traditional software companies are battling with how, how to, how to stay relevant, how to battle with, if I'm in a per user model, if users start to decline, how do I not decline?

So it forces them to rethink their equation, not just about users, but value. And if you can cling to value, you at least potentially can stay at hopefully steady state. That's, that's, that's what you're hoping to do is steady state. So if you're not leading, you will find behind and fall behind and where Island sits. And we'll get to that probably in a little bit is kind of right, my, my company or our company Island, not my company, our company Island that is pushing, pushing what was legacy software, trying to push that forward while being a massive enabler of AI. But it is a, it is a, a, a wild ride right now. But if you are leading, there are so many fruits to be gained. It's just not a world for followers right now.

So, and I agree with you and I, you know, my analogy of AI is it's kind of like, uh, you know, getting chased by a bear, right? You don't have to be the fastest person. I just gotta be faster than you. Right. And so the idea is like, it'll eat the people, the followers, um, which is, which is what worries me quite a bit because there's only a select few leaders in truly, you know, true innovators. And, you know, I'm looking at my industry, the SaaS industry that I grew up in and made the vast majority of my money, you know, as far as training and enabling the, the, the predictable revenue model of the segmentation of roles and sales and all that stuff. And so I, and the, and the, you know, per license thing, I, I'm looking at this industry going, I don't know how this industry survives, specifically the middle market section of this industry.

I think the, the, the young, the, the small ones who can adapt, you know, who can build from scratch AI are going to leapfrog. And I think obviously the, the big ones, you know, the Microsofts and those of the world are going to just eat up. So what's your, I guess, what's your advice to those middle market, uh, SaaS tech companies that are, you know, got a valuation of $2 billion, three or four years ago and are sitting there. You know, it's basically in a paperweight at this point, as far as software is concerned with a lot of legacy sales reps, a lot of legacy technology and trying to shoehorn in AI to say that they're AI enabled when they're fundamentally software that can be developed now with a prompt.

Yeah. Uh, yeah. You know, when you think about the, well, first of all, when you think about, in some cases, smaller companies that have a unique value proposition that is AI forward and is driving efficiencies. In some cases, I think they're going to be okay because they don't have as far to fall. When I think about some of the, the bellwethers in software, they're going to your point. They're going to survive because ultimately, you know, is, you think about Salesforce, Salesforce is an amazing company that has built a ton of value over time. Uh, are, are they experiencing turbulence in the marketplace or other SaaS companies, uh, experiencing turbulence? Yes. Are they going to, you know, be fully replaced?

Probably not. But are they experiencing a downturn? Yes. Will they rebound at some point? I think so. If, if, if they, if they get back into a leader's mentality, the smaller companies that don't have as, as far to fall, won't, won't, you know, they're, they won't experience the pain. Um, and so if, if they can build the build value equation in a different way, it's not just a per user model anymore. And if you can build without, in a, in a different mindset, you can actually see, I think, greater acceleration. I know we're, we're thinking through that, going through that, you know, we're, we're fortunate enough where I think we are innovating at a massive clip. So when we look at, you know, at that old per user model, we're not stuck in that declining per user model.

We've already progressed into that value and more of a value-based model. So, and so let's talk about Island, right? Cause let's, first of all, give some context of, of what you guys are so that the audience knows. And then let's dive into this whole, you know, when you started in stealth mode, right. And, and they had no revenue. And then, you know, you were going in these enterprises trying to sell something effectively that the perception was, I already have something like this. I got it for free. So why, why would I pay for this? And the, the connection tissue here for me is a lot of, you know, I talked to, um, Tableau and a lot of these BI companies where Google analytics, they fight that every day.

It's like, well, Google analytics is free. Why would I pay for Tableau? Why would I pay for Click? Why would I pay for these things? So first give some context of Island and then let's jump into that conversation of selling something in such a flux market right now where everybody's like, well, I can do that with AI. So why would I pay for it? Yeah. So I rerun the clock, uh, five years ago, five and a half years ago, which now seems like 15 years ago, it's crazy. Um, but, uh, Island saw a unique opportunity that if you think about how work gets done, work gets done typically in a browser, when you think about, Hey, how, how do I access applications like Salesforce? How do I get email done all the tasks, Slack teams, all the things that you do on a daily basis for the most part had moved to a web-based model, but traditional architectures were deployed to protect that data around the browser.

So you have things like virtual private networks, VDI, uh, legacy, SASE architectures, data loss prevention systems, web proxy systems, firewalls, all these things that exist around the browser. So organizations used to have to invest in all these solutions around sort of where work was happening, which is the browser. Island saw a unique opportunity to say, well, what if the browser was integrated into the architecture? What if the browser was integrated into your identity stack? What if you could take things like data protection and web security and put those at the point of inspection where work is happening? That was the value proposition on a PowerPoint slide in August of 2020. The vision was bold.

We were able to raise a good amount of money, uh, to go, to go prove this out. And then as it kind of builds into, into your question of, of, uh, you know, being for free, yes, nobody paid for a browser since the mid nineties. And we were coming to organization. I remember telling my dad what I was going to do. And he's like, God, Eric, I can tell you're excited, but you know, they're free, right? And, uh, I was like, yes, but I think we can bring something really compelling. And so what we decided to do was create this category known back then as the enterprise browser. And we thought if this brown, if this category is going to have staying power, we need to be able to prove it in the global 1000, not in our minds, go to small organizations and hope that we could go up.

We needed to go establish it at the large organizations to ensure not only that they would validate that there's product market fit, but we could deploy at scale. And so we were very, very fortunate that we hired salespeople. We built a value proposition that worked up market. And so if you fast forward just probably three years into our journey, we were able to get eight of the top 10 U S financial institutions as customers, but because of how, what Island does, we were able to tackle so many different use cases. We were able to, you know, uh, enable a deal room for financial institutions trying to broker a transaction because if you use our browser, you can ensure that data stays resident in a central repository and doesn't leak out to other organizations.

We're able to enable things like a merger or an acquisition, uh, third party contractor access. And you think about organizations, take like a, uh, an, uh, an Eli Lilly organization like that, which has a large workforce, let's say in China. It's doing great work for them, but how do they ensure that data stays, uh, resident in China and doesn't bleed back, back and forth. And so Island provides an easy way to get access to the application while, while ensuring that that data stays, stays resident. So those use cases really went across all verticals, all segments of the market. And we were able to start to, to kind of, to, to, to grow across all segments, all verticals, while being able to reference that we can do it with the largest companies in the world.

I love that. So I want to talk about how you positioned it, right. The free versus, but, but let me back up a little bit to the, to the hiring. Um, what were the, what was the profile of the rep you looked for to do that? Really good question. And the profile that we look for today is actually a little bit different. Uh, as you've met now that well, cause I, cause that's kind of where I want to get to that stages of a business, right? There are certain people that are great at certain stages and then they kind of grow out of it. But I want to understand when you were at this stage, the stealth stage, knowing that you had to go there, what kind of people were you looking for? And, and, and we're so Mike, Mike Fay, our, our CEO, um, had a, had somebody's like, Hey, in our first five to 10, 15 hires, I, I want to make sure we are hiring known killers.

We are hiring people that we have worked with in the past that we know are the best and they have it. They have a network, uh, they know how to run an effective sales process. They know how to drive value. And so the first 15, 20 reps, I all knew, you know, were, I knew personally, I'd sold with them before. The reason that was so important for us is as we were coming to market, we needed to be able, if there was a problem, we needed to be able to isolate the problem. If, if we weren't having success, we can tell you for sure. It wasn't a sales process issue. It wasn't a prospecting issue because these are people that we know are unbelievably successful. If we're having a challenge, we get isolated to the product.

And when you, when you end up coming and I, you know, this is the first time I'd ever brought a company from a go to market perspective, I spell, but what I'm learning, I'm talking to others is in some cases, there's a lack of trust between a technical founder and a go to market team. Oh God, in some phases, all of them, my friends, almost every company I've had that started with an engineer, like they, they almost look at sales as a second class citizen, a lot of ways, because they can't stand it. We were very fortunate. And then you look at our co-founders, Mike Fay is a very, very customer focused, go to market leaning CEO. Dan Abiga is one of the most brilliant technical minds I've ever met, but there was an agreement that Dan, you're going to build the most amazing product and platform the industry has ever seen.

Mike, Eric, you guys are going to build the best go to market engine that you guys can build. And when we're never, we're always, we're going to trust each other that we're doing, we're doing a great job. And that, that trust. And we were just fortunate initially that it just happened. Dan, Dan's team built an amazing product and platform that started to drive value. We built what we said we would. And so we had trust, which allows us to go fast. There wasn't, if we, if the sales cycle wasn't progressing, it wasn't, well, shit, we didn't, we didn't call it the right level. We weren't doing the appropriate discovery. We weren't delivering the right PowerPoint. It was, hey, let's go back and assess.

It's most likely that we need to be tweaking our, tweaking a certain feature. We need to add these features or whatever it was. We could, we could isolate the problem. How did you set that feedback loop up? Because I think that's one of the biggest misses in organizations is that when there is the engineering and the sales, the sales is like, there's your market intelligence. If you, if you leverage it, right, like they're collecting all this information and they're the feet on the street, seeing what clients are reacting to and whatnot. But I, I rarely see a genuine feedback loop when it comes to, hey, this is what we're seeing out in the market. We got to fix this. And that, you know, for me at a much smaller scale, when I was selling IT services, you know, I would constantly push our services and our IT team because I'd be like, look, this is what the client's asking for.

Like we just lost two or three deals because we couldn't do these things. Or in some cases, because I was the VP and one of the founders, you know, I'd be like, look, we're doing this. Like, I'm sorry. I just got a huge project. It's gnarly. It's gross, but it's going to lead to some revenue and it's going to lead to a bigger picture. So I'm sorry. I'm calling this one. We're going to, you know, I, and it would, with the other executives, like we're going to push this and kind of try to break some things and get out of the comfort zone here. But we never really had a feedback loop other than me coming back to them and be like, guys, like we're losing deals because of this. What was the structure that you put in place to align that and have that trust and feedback loop so it was so iterative as you went?

I think there were two things I'll call out. One, we didn't limit the access that I would, you know, we didn't limit access to our customer engagements. If we were dealing with a Fortune 100 company and we were on a, on a, on a Zoom or in person, bring in the engineers, bring in product management. In addition to the sales engineer and the rep, let's, let's lean in, let's listen to the customer together. And then when they ask about a feature back then that perhaps we didn't have that made sense, we would immediately go build it. If we saw the feature and we thought this could have value to other customers, we would immediately go build it. Back then our feature turnaround time was about eight days.

We were fast. Now, still today on feature turnaround time, we're about 21, 22 days. So we still really, really lean into that. But the other thing that we did back then was, hey, we were years away from being a publicly traded company. We weren't, we weren't wanting to be acquired way back then. We made it very easy to transact with. So if a, if a customer needed us to write in that you will deliver this product feature and sign up contractually for it, you know, some organizations say, no, we can't do that because of, you know, it's a contingency in the contract and it defers the revenue. Who cares? We're, we're, we're early, write a contract that works for your customer. And so we were very, very customer leaning in terms of our, uh, what we did from a legal perspective and what we did from a product contingency perspective.

Cause remove the barriers to engage with a customer, especially back then. And that really, really helped. But I'm curious though, because I mean, you're dealing with some sensitive shit here, man. Like you're an enterprise browser that could go on and extract whatever information and leak it out there. So how are you able to do that from a, from a risk to like, how did you even assess risk as it related to that? Because I got to imagine your lawyers were out of their mind being like, uh, hold on a second. We can't just write that into the contract here because that opens us up to a major, so how, how did you balance the risk factor? But yeah, think about the key things around limitation of liability, confidentiality, private data privacy, all those things, uh, unbelievably important.

Yes. Were we giving unlimited liability and things like that? No. Um, because the challenge with doing something like that is let's say you're dealing with a fortune 20 and you've given unlimited liability that could preclude your opportunity for success in seven, eight years that you wouldn't think about. But because we were giving on other things like around deliverables, product requirements that we were leaning in more times than not the business side on their side would lean in and say, guys, they're really doing a lot for us here. Let's, let's lean in and help them what they need here. Um, and you know, what occasionally, you know, we, we, would, we have to give a slightly higher super cap five years ago for, for liability.

Yes. Then we would do today, of course. But when we would really lean in on what was important to them and more times than not, you know, we were, we recovered, but, but they wouldn't say, gosh, you're so easy to do business with. It's because we, we said yes to the things that we, and I wish we, you know, that more organizations can say yes to, but out of principle, they just don't. So with that, let's talk about the sales process now. Right. Because you said, you know, unfiltered, bring in engineers, bring in executives to the, but how, like, you know, traditional build your champion, you know, have your champion go work with you. Did you bring in procurement early? Did you bring in, like, how did you facilitate those, those upfront conversations so that you had everybody on the same page?

Because that, hey, they're so easy to, to work with sounds to me like an executive that you worked with going to procurement and going to legal being like, look, man, they're giving us a ton of shit here. Can we, can we be a little bit flexible with our terms on their ends? So walk me through kind of what the, what your approach was with these all-stars, with these killers that you hired, what was the kind of the, the, walk me through that intro and then how did they collaborate and get everybody together? So you didn't have to do that with the business owner and then go fight the battle with procurement and legal to get this done. So fortunately, we, we probably had an easier path here than some have, because when you think about selling four or five years ago, an enterprise browser, it, it's a new category and it changes so much about how, how an organization works.

It changes how you access applications. It changes how you deliver web security, data protection. It changes so much about, uh, end user computing. In some cases, you don't have to ship laptops, all that stuff. It changes so much because of that. We had to start at a C level. And when you start at a C level, and one of the things that, that we were very prescriptive about is you have to start high because what we're doing demands massive change. And it, and it demands that you work with a change agent. It also demands that in a lot of cases, it's not a siloed sale. Uh, you're not just selling a security widget to security. And so you go CISO down, we wouldn't, we might start with the CISO because we had a security anchored value proposition, but then we realized we also needed to go sell to the vice president of end user computing.

And now we even, you know, fast forward, we now sell to the AI's are, and so because we would sell in a way that was not just high, but high and wide, when it actually got time for procurement, we had sponsors at that level that would then push procurement. And so we're going to say, Hey, we're ready. We have alignment across the key, you know, the key levels of the organization. Okay. That kind of, that's what I guess, but I just want to make sure. So now, but now getting access to the C-suite at enterprise that, you know, everybody's crown jewel, right? So was that the networks of the people that you hired? Was that their prop, was that their kind of, what was, what was your strategy to get to those levels?

And was it connections or was it like traditional outbound prospecting, which I can't imagine, but if it is, I'd love to hear it. We did hire people with a net, a network early on when they were, you know, I don't like to think of myself as old. I think of myself as seasoned and mature. And so we weren't hiring the traditional startup reps that perhaps didn't have a network. They were quote unquote seasoned or mature. So they had a network. Yes. But then we did something else. You know, we wanted to lean into the channel five years ago, but the channel is not really an effective way to create a category because they have big numbers. They are there to help organizations scale. And so how did we start to get pipeline at scale was we created an advisor network.

This was very, and it was unique to me because I hadn't really leveraged advisors. Advisors could be back. It could be, Hey, this is a CISO that I have a relationship with that sees the value of Island and is willing to make introductions to me, to their network. It could be people that have retired and just want to lean in and help. It could be, Hey, this is what they do professionally. And as we started to meet these advisors, the program just started to grow. And if you fast forward today, we have about 70 advisors and it's not, you know, yes, we, we work with them to access their networks, but they also give us feedback about, uh, about the company, about the value proposition. And it was really, it was really unique because it was a two way street.

You know, there was compensation in it for them, assuming there was value being, being brought. Um, but, um, I mean, I remember going, um, to, uh, uh, the, the, the CISO of an X very, he was excess of a very, very large retailer and, um, out of time, respect for him. And I just called him up and I said, Hey, I want you to understand kind of what Island is doing and why I'm passionate about what we can do. He said, wow, that's really interesting, Eric. And I said, Hey, would you, would you like to help us initially, uh, with our growth and getting this value proposition in front of your peers? And he said, yeah, potentially. And so then I created a structure for him that he won and we won. And so that was unique that, that we kind of started this and then it's really grown over time, but it was, it was something that allowed our salespeople to get scale without their own direct prospecting.

And I think that's where, you know, I keep talking to sales reps right now, especially the, the ones who have grown up in the predictable revenue model and the, in the remote, you know, world of, of, of, of zoom and all that stuff, man, your network, right. It would go back to Mark Cuban even says that your network is your net net worth, right. The whole thing about building relationships and having access to people that can make your life a thousand times easier. And I think so many reps have gotten away from almost building their own ecosystem, regardless of what the company does. I mean, I remember I used to just call up the best sales reps of all the vendors that were even remotely associated with clients that I sold to.

And just said, Hey, you know, you and I focus on the same people. Sometimes my clients need your stuff and I'm guessing sometimes you need my stuff. You want to set up a little kind of weekly thing where we get together, right. I would just do that just proactively myself. And some of those relationships still to this day, you know, 30 years later is still bearing fruit because I developed those back when I was a kid. It is, it's actually easier said than done. You have to be very intentional. Yes. And you, and it's gotta be, it's gotta be a two-way street. It can't be a selfish investment. Um, uh, but those that have done it, I have massive respect for it. Um, because they've intentionally found ways to stay engaged and deliver value in a, in kind of a two-way scenario.

So, well, I mean, the easy way to do that, at least from my perspective is, is, you know, at the end of the day, as you know, and this is, we're going to get to the, how you solve these problems, but you know, sales reps are problem solvers. They should be right there. They're not about there to convince anybody of shit. It's like, I'm here to solve a problem. Right. And sometimes, unfortunately, that problem isn't something that your solution can deliver, but if you become a problem solver and you put your backpack full of a bunch of tools, resources, companies, partners that can solve problems around your problem, maybe root cause issues or whatever, and you bring those in, that's why you, that's where you start.

You start with, what does my client actually need? What are the questions I'm getting? And who can, who can I bring in to, to add value to that client? Then you go talk to those partners and say, Hey, I actually need you because I need your services. So would you be open to me giving you some business basically, right? Who's going to say no to that? And then you develop that. You start with the give, you start with the fix the problem. And then nine times out of 10, it, it evolves into a mutually beneficial relationship because you're given so much that they're coming back to me like, look, dude, like we got to, but to your point of being intentional is huge. Like you can't just be like, Hey, let's share some business together.

I'll talk to you next month. All right. So let's talk about positioning here, man. Cause this is what I was really curious about as we, as we unpacked this. It's, it's, you know, a weird world right now. I know for me, I, again, solo, you know, two person shop here. I've canceled a lot of contracts with a lot of vendors. I've turned down a lot of conversations. Cause I just look at their product or service and be like, look, I can do that now. And you were walking into a world where that was it. I mean, we got Chrome. Why the hell would I need this? So how did you position it? And was it, was it all based on discovery? Was it objection handling? I know it's a, it's a combination of everything, but what was the positioning walking in the door, knowing that that was your, probably your number one objection you were going to get.

And I think we became aware early on that there were certain use cases that Ion was a great fit for. And so we, if you think about the different sales methodologies, although we didn't call it at the time, it is probably more of a challenger type mindset because we knew certain organizations would have a large contingent work. So if we knew an organization, for instance, had a large contingent workforce, we could make certain assumptions. We could make assumptions that they're probably shipping laptops to third parties. We could make assumptions that on those laptops, it is expensive software that you've had to deploy on those laptops. We could make assumptions that you've had to stand up an expensive VDI infrastructure from an organization like Citrix or Omnisa.

That there was, so there was capital expenditure to set up this VDI infrastructure. There's variable costs in terms of shipping devices and putting software on those devices. What if you just needed a browser? What if you just needed a browser to authenticate via the IDP, Okta, Ping, Azure, Entra, and get access to the applications? And that's it. What if that time to value of bringing somebody on to an application or into an organization was 30 minutes instead of four weeks? What if you didn't have to ship a laptop only to find out that that contractor got a better offer and then realizing they're not going to work for you and you're never going to get that laptop back? So we could go in with some assumptions pre-baked that you're probably experiencing this.

The other thing is if we knew an organization was about to go through an M&A event, hey, you're about to make an acquisition of a 5,000 entity organization. You're not going to have to need to access each other's applications. You're probably going to have to run dual laptops, dual phones. What a pain in the ass. Users hate it. What if, again, if you needed to access the other companies' applications, you just needed a browser? And so when they started to hear the value proposition, there was immediate ROI. It's like, yeah, I know a browser's free, but you're now creating an alternative than what I used to have to do. So there was immediate ROI. There was better user experience. I've been in cyber since 2004 when I got to McAfee.

This is the first time we've ever, and if I look at, and we're approaching almost 1,000 customers now, if you went and polled those customers, almost every single one would say user experience is better. Go ask another cybersecurity company, and cybersecurity companies don't talk about user experience. They talk about protection, locking down. We're somewhat liberated because now, all of a sudden, if I'm a financial institution, I don't have to carry two phones. I can actually just use my own phone to access corporate applications because I know it's secure. And so we were able to bring forth value propositions that we thought could work for that organization based on what we knew about that organization and based on the value we were already starting to deliver.

And then once we would win a financial institution or we would win a pharma or we would win a life science or retail, we started to realize, okay, it probably is the case for others. And so then it slowly started to build. And so the notion of, hey, I'm paying for something that is free went away because now it's like, holy cow, I only can get rid of 12 or 13 pieces of my IT stack today. So, and pardon my ignorance here, but if I think of Claude Cowork, right, it can go through the browsers for me. I mean, I watched it clean up my instance of Salesforce the other day. It deleted 15,000 records that had no information in them. It tagged every client in my, you know, as a client versus a prospect.

I mean, it enriched all that. And I watched it as it did it, and I gave it approval, you know, to go through and connect to Salesforce. So, you know, help again, ignorance on my end, comparing the two solutions here. But a layman says, I don't know, cowork, man, I just lit this up two weeks ago, and it looks like I can go between applications and give it access to this stuff and have it do all that shit that you just said. So, like, is it because of the level of the conversation and the understanding of what it was? Or was it genuinely, you know, you coming with a hypothesis and confirming that hypothesis and then digging into the details of the actual problems? Yeah, it was a hypothesis. Let me show you how we do it and then discovery.

And it was interesting. Now we do discovery much earlier in the process. But because we were brand new and we would set up a meeting, most organizations didn't have tolerance for us to come in and do a massive amount of discovery. They needed to be educated. Why should I even share data with you? And this was even before that, you know, AI has really allowed, it has really changed discovery. And this was, I think about five and a half years ago, you weren't just going into Claude or Gemini or whatever it is. But we kind of had to earn the right to discover. And so, we would give them our hypothesis of why we thought we could be successful for that organization. We would then show them the product, which they were like, holy cow.

We had a tagline that said, sometimes changing one thing changes everything. And they would see it and be like, oh, wow. If now it's not using a consumer browser, I'm using an enterprise browser. Well, that changes so much. And so, then after they would glom on to that, we'd say, okay, great. Can we now carve out time to do a deeper discovery and discover how you're enabling access for your own employees and third-party employees to your critical applications? Can we discover how you're doing data protection? And then, you know, in most cases, they would say yes. But back then, they might say, yeah, we'll get back to it. And it was crazy. And this was the hardest thing, was that that first meeting would always go awesome, every single time.

And they'd say, well, let us come back to you. But the reality is, in some cases, sometimes they wouldn't. Because we, and it took us a while to realize that what we were doing was changing so much, and they may not have been ready for that change. What's encouraging is that as I fast forward, you know, from that point to three years later, now even five and a half years later, the number of organizations that have come back, you're like, oh, thank God. What we did, it wasn't for not. They actually got it. They've now come back, or they've tried an alternative or something, and they've come back. So it was, I don't know, maybe we should have done more discovery at the time. But we felt like we had to earn the right to discover.

And so now, you know, we, of course, discover early on. But anyway, it was a lot of learning. But that shift is real, right? Because I think, to your point, like, no executive specifically right now wants to be discovered or qualified, right? Like, if you're not coming to the table with something I don't know, I got no time for you. So that's why I've shifted a lot of my training towards hypothesis selling. Because especially now, with all the AI tools, I can come up with a pretty damn good hypothesis right out of the gate and then confirm it and say to them, look, here's my hypothesis. If this is your issue, we should talk. If it's not, we shouldn't, as a matter of fact, because you're not the best suited for what I can solve here.

And disqualifying almost out of the gate with your hypothesis. If you, yeah, I love that, actually. I think that is a wonderful way that you're training. Because if you're not doing that, you're lazy. If you're showing up to a call and saying, what's keeping you up at night? Are you kidding? Shut up. Like, I will literally hang up on somebody. I say my daughter and I hang up the phone when somebody asks me that stupid question. Yeah, don't ask me what my challenges are. You can find out my challenges in about three minutes. In about three seconds. Like I said, the three most insulting things you can say to anybody right now, in my opinion, what keeps you up at night? Tell me about your business and what are your priorities?

Those are the three most insulting things. Because I could easily go in and say, what would keep somebody like Eric up at night? What would be somebody like Eric's priorities? Tell me about their business. How do they make money? And you could do that now in like 30 seconds. Whereas maybe in the past, I could give you a little bit of a pass because, you know, you had to read through a 10K. You had to spend an hour or two really thinking through the business. And most people aren't patient enough to do that. Now, you're out of your mind if you don't do that prep before a conversation. And you are with my most valuable asset, by the way, which is time. You're going to waste it by asking me some dumb dipshit questions, like for the first 30 minutes of our conversation and then, you know, flip to your dumb demo.

Like I have no interest. Like this is sales is changing so drastically right now. If you don't have that mentality, you won't even be invited to the table. Or if you are, you'll be canceled within five minutes of the conversation. That time is so important in what you invest up front to make sure that time is spent with the client matters massively, massively. Awesome, man. Well, look, a lot going on right now. What are you excited about? Like, let's wrap this up with what are you really, what's getting you fired up right now to keep going, you know, with this duality of where we're at right now, which is, holy shit, this is super cool and fun. And then, oh, my God, like what, how fast is this going and what, where are we headed, right?

Because I'm, I'm faced with every morning, every minute I'm switching gears here being like, I'm terrified. I'm super excited. I'm terrified. I'm so excited. So let's leave the terrified stuff for another conversation. What are you super excited about? Yeah, I mean, you're right. The second you feel like you have the tiger, the tiger by the tail, the tail whips you in the ass. This is not a time for complacency. No doubt. And it, you know, one of the awesome things that I've loved about Island is, you know, we, there's two main cultural values that, that have been super important to us. And some, and most of the time they don't work well together. You know, one is speed, but the other is intentionality.

Sometimes when you're intentional or deliberate, it, it slows you down. And you, you, you, you, you try to make decisions by committee because you want to make sure you're so deliberate and intentional, but when you can't effectively combine those to where you're intentional and deliberate, but once you make a decision, you go. Um, it, it can enable value creation, uh, and, and delivery in a, in a very meaningful way. And there are certain things about Island that even though you're having to move super fast, we're never going to change. Like when I think about it, I love, I love this, this model where when we do deployments, it's not just a customer successful deployment. It is a Island deployment.

Our SEs are responsible and lean in. We have customer success. We have technical leaders. Everybody's responsible for the success of that, of that customer. That piece will not change. We have to continue to do that. It's an expensive model for us, but we think it's the right model to ensure success. But why I get excited about Island is you think about our presence right now in the fortune 500 fortune 100 global 1000, et cetera. And I think about that. We're still relying on speed and, and you mentioned co-work. And I think about just the Island isn't thinking about, okay, how do I, how do I catch up and how do I just enable co-work? How do I provide a better experience within it? How do I realize that organizations are maybe not just going to be dependent on co-work?

They're going to be dependent on so many different facets of AI. And how does Island not just enable it from a security perspective, but how do we make the experience better? How do we help organizations create, you know, the promise that started with robotic process automation six, seven years ago? How do you make that relevant and meaningful with the browser? How do you, how do you enable application publishing? There are so many things that, that we are doing to bridge the gap between true information security and AI enabled application and access. And that is such a cool position to sit in because typically on the, on the infosec side, you're, you're just about protection. Yes, no, but you don't blend both sides.

And I think it's hard to think more than a couple of months out now. Really, you know, it, it really is. It's like, I was interviewing somebody the other day and they're like, gosh, tell me what you think about Island in 24 months. And I'm like, well, I hope 24 days I might be able to give you that answer, but, but what's exciting is I think we've, we've built the right formula for making our customers successful at speed and scale. But then what excites me is the speed at which we're leaning in to blend security with enablement of the business. And, uh, I know that's kind of a broad answer, but there's a lot underneath that, that, uh, make me, I made me super excited. Yeah. I tell you, man, this is, I, I keep saying for creators, um, this is, this is the golden age right now.

Like if you have ideas, if you have, but my fear is for workers, like people who are not like creative people who aren't innovators, people who aren't don't push. And to your point, our status quo, because it's comfortable for them. They don't like rocking the boat like those are the ones I'm worried for right now, because they're not, they're, unfortunately, it's just a matter of time at this point. And so we got, that's why I'm trying to wake everybody up. Who's not paying attention to what's going. I think you and I are in a very beneficial scenario where we live in the tech world and we see what the, what it it's doing. And it kind of can see what it can do as a vast majority of our population that has no exposure to this other than what they see on the news.

And, you know, I think this is coming faster than most expect. So one of the things that we talk about, and this is CEO led is we have to live in it. We can't just talk about it. He pushes all of us to do as many things that we can using modern thinking and modern AI tools. Things that we used to just have would have said, yeah, we'll just go buy that or, yeah, somebody asked for data. Yeah. You know, give me a week. No, somebody asked for data. You should have it back in 30 seconds. Like you need to go create a dashboard. No, that's there for you. And so I think that that has to be embedded into organizations too. You can't just be a company that talks about it. You have to actually do it. And I credit our CEO for really creating a mentality and a discipline around that as well.

Love it. Awesome, Eric. Well, I think I share your optimism. And like I said, we'll leave the terrified conversation Terminator stuff for another call. So let's let people know where they can find out more about you, about what you guys are doing over there and everything where you want to point some people. Yeah. Well, you know, when you think about accessing and getting, working with Island, we've got a pretty large network that you can engage with from coming right to our website at Island.io. We've got an amazing network of channel partners. Now, I mentioned five years ago, hey, it was tough to get the channel behind creating a category. Now we're so blessed that they're in it. They get our value proposition.

They're really leading from the front with us. So I'd love for you to engage with traditional channel partners, niche channel partners. But that's a great way to get in touch with us. And I promise if you get in touch with us through a channel partner or it could be through something like AWS. We've launched as we kind of create scale through something called AWS Security Hub. You can now experience Island at a large volume or start with a smaller volume. We're quick to turn that around and enable you through that as well. So many ways to get in touch with us. I promise, as I talked about, speed will drive the day and we'll be back in touch with you ASAP if we can help you out. Love it. And for those of you listening, it's Eric with a C and it's Apple, A-P-P-E-L, if you want to look him up on LinkedIn and see what he's doing there as well.

Eric, thank you very much for coming on. It's been a fun conversation. I really, John, really enjoyed the chat. You engage in a very unique way. I think we share some similar philosophies. And it was a great, great hour spent with you. Thank you so much. Appreciate that, my friend. And hopefully everybody enjoyed the conversation as much as I did. And like I said at the end of all these podcasts, go out there and make somebody smile today. Because no matter how bad your day is going or how bad you think it went, if you make somebody smile, you know you had a good day. And the world needs a lot more of that right now. So thank you all very much. And I will see you on the other side. Hey, thanks again for listening to the show and for all your support throughout the years.

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