The Vision Architect

Cybersecurity leaders face a paradox: the pace of technological change accelerates daily, yet teams need stable direction to perform. In this episode, Trent Hein, three-time founder and co-author of the Unix and Linux System Administration Handbook, explains how organizations can set a clear vision without constantly pivoting toward every new trend.

The core framework Hein advocates is design thinking applied to strategy. Rather than chasing technical minutiae, leaders should start by mapping the experience they want to create—whether for clients, employees, or end users. This approach grounds every decision in a higher purpose: for Hein's cybersecurity firm, Rule Four, that means helping clients "sleep at night" by achieving a tolerable risk level. He warns against what he calls "audit theater," where organizations become skilled at showing auditors what they want to see rather than genuinely fixing vulnerabilities before attackers find them.

Hein introduces the "Crazy Eights" exercise from Google Ventures as a practical tool for gaining strategic clarity. By asking team members to sketch eight different visions of success in just five minutes, leaders can surface diverse perspectives and build consensus quickly. He also shares how Rule Four operationalizes its "life first" value through coverage processes that allow employees to step away for personal emergencies without guilt—a practice that has led to "employee boomerangs," where former team members return because they couldn't find better culture elsewhere.

The conversation also tackles AI's accelerating threat landscape. Hein reveals that vulnerability exploitation time is projected to drop from years to just one minute by 2028, fundamentally changing how both defenders and attackers operate. His advice: ask the same integrity questions of AI platforms that you would of a human partner—does it share your values and mission?

Highlights
  • Set vision by defining the experience you want to create, not the technical specifications.
  • Use the "Crazy Eights" exercise to surface eight different perspectives on success in five minutes.
  • Build coverage processes so employees can step away for life events without guilt.
  • Avoid "audit theater"—welcome auditors who find problems before attackers do.
  • Keep teams small (under 45 people) to avoid politics and maintain family-like cohesion.
  • Ask every AI platform the same integrity questions you would ask a human partner.

Important Concepts and Frameworks
  • Design Thinking (Stanford) — A human-centered approach to strategy that starts with mapping the desired experience or outcome rather than technical requirements.
  • Crazy Eights — A Google Ventures exercise where participants fold paper into eight rectangles and sketch eight different ideas in five minutes to force multi-perspective thinking.
  • Audit Theater — A phenomenon where organizations become skilled at presenting what auditors want to see without genuinely fixing underlying security gaps.
  • Employee Boomerang — When former team members return because they couldn't find better culture elsewhere; a metric of healthy organizational values.

Tools & Resources Mentioned
  • Rule4 — Cybersecurity firm founded as a public benefit corporation focused on applying technology to improve the world. | https://www.rule4.com
  • Unix and Linux System Administration Handbook — Reference book co-authored by Trent Hein, used worldwide.
  • Anthropic — AI safety and research company; recent data on how AI will impact cybersecurity.

Calls to Action
  1. Run the Crazy Eights exercise with your team to surface multiple perspectives on what success looks like for your next strategic initiative.
  2. Evaluate whether your organization is practicing "audit theater"—and shift to inviting genuine auditing that finds problems before attackers do.
  3. Ask your team: "How does this make the world a better place?" Use the answer as a filter for which clients, projects, or technologies to pursue.
  4. For any AI platform you adopt, assess whether the provider's mission and values align with your organization's integrity standards.
  5. Curate a set of mentors outside your current work environment who can provide honest perspective during both good and challenging times.

Key Quotes
  • "I want them to sleep at night." — "Trent Hein"
  • "The best way to secure something is to not have it." — "Trent Hein"
  • "Anything is possible if you take the reins and build the business you want." — "Trent Hein"
  • "We always have to focus on what we know today and be willing to reevaluate." — "Trent Hein"
  • "If you have a good set of mentors, they'll be by your side in good times and bad." — "Trent Hein"

Chapters

00:00 — Why Higher Purpose Matters More Than Technical Details
03:07 — Building a Public Benefit Corporation That Does Good in the World
04:51 — "Life First": Operationalizing a Culture That Supports People
10:20 — Design Thinking as a Framework for Strategic Clarity
12:20 — Helping Clients Sleep at Night: The Real Goal of Cybersecurity
17:53 — AI's Double-Edged Sword: Vulnerabilities Found in One Minute by 2028
23:51 — Crazy Eights: A Five-Minute Exercise for Strategic Consensus
27:50 — The Skillset Needed to Build a Thriving Tech Company
33:07 — Communicating Vision When the Future Is Uncertain
38:15 — Looking Backward from Three Years Out to Define Your Path

This Episode's Guest:

Trent Hein
LinkedIn: https://www.linkedin.com/in/trenthein/
Website: https://www.rule4.com

About the Host

Simon Vetter
Website: https://simonvetter.com/
LinkedIn: https://www.linkedin.com/in/thevisionarchitect/


Creators and Guests

Host
Simon Vetter
Simon Vetter, known as The Vision Architect, is an international executive coach, professional speaker and author of "Leading with Vision". He helps leaders create crystal-clear vision and practical execution, aligning teams and accelerating performance. His work is trusted by organizations including AbbVie, Cisco, Lennar, Microsoft, Qualcomm, and Siemens. Born in Switzerland and shaped by 27+ years in San Diego, Simon blends Swiss precision with Californian innovation: pragmatic, energizing and actionable for real-world leadership pressure.

What is The Vision Architect?

The Vision Architect is the podcast about crafting bold, aspiring futures that inspires lasting change. It is for leaders facing pivotal moments or crucial challenges - those crucible experiences where big decisions shape the future. Each episode is filled with stories, ideas and tools to intentionally design a meaningful path forward, gain clarity amid uncertainty, and ignite the courage needed for enduring change. It's a powerful conversation about what's next - for your life, career, team, and organization.

[video] VISION 210 Trent Hein
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[00:00:23] Simon Vetter: I am excited about today's guest, Trent Hein. He is a three time founder of tech companies also. He is, um, and co-author of the Unix and Linux system handbook that is used worldwide as a reference book, and he has received a lifetime achievement award from the Unix. Niks Association. So Trent is a very reputable and well-recognized voice when it comes to cybersecurity and information technology engineering.

I am happy to welcome you, Trent. Welcome to the show.

[00:01:08] Trent Hein: I'm happy to.

[00:01:10] Simon Vetter: We will talk about vision. We talk about how to prepare and how to set direction in a very fast paced, ever changing technological environment. How do we bring people along? How do we distinguish between staying agile and stable at the same time? And of course, we'll talk about AI and how this impacts the world and how do we react, respond to it.

Let's talk about. Vision so in a technological environment, how do we set the direction without always adapting and changing and rewriting it? How do you balance between setting a clear direction where we are going and not always kind of shifting and turn looking for the shiny objects?

[00:01:58] Trent Hein: Yeah, that's a really great question. And I, I think the most important thing, at least in our business, is to always understand what our higher purpose is. Like what, what does it mean to do the right thing? And, you know, where are we headed long term? We can spend a lot of time on a. On a, on a given project or a given topic, debating various technical nets.

But I always try to encourage folks to pull up to, um, you know, what's the goal here? What does the, the business need? Or what does the organization actually need, and how does that make the world a better place? Um, this is a, uh, an interesting thing to say as a, a cybersecurity practitioner is like, oh, cybersecurity.

How does that work, make the world a better place? Well, we could always be able to articulate that, and I, I, I always challenge, uh, clients that I work with and, and team members that I work with to ask that question. Um, WW why are we doing this? How does this make the world a better place? And if we can answer that question, then the technical nets, uh, in a lot of cases just don't matter as much, right?

Because it gives us that guiding light.

[00:03:07] Simon Vetter: What is that for your current company? Rule four.

[00:03:12] Trent Hein: So, I'll tell you a little bit about rule four. So we were founded in, uh, 2018 and we incorporated as a public benefit corporation, which is, uh, special, uh, type of corporate structure that allows us to have multiple purposes as a corporation. It's not just about, uh, doing business and making money, um, but we have a.

Public benefit goal and our public benefit goal, uh, is specifically focused on how do we apply technology in a way that I improves the world? And, you know, that that could have a variety of meanings depending on the exact context. Um, maybe it makes it easier for folks to access healthcare. Or, um, maybe it makes it easier for folks to, uh, go skiing and, uh, uh, use a, a past product securely and so they get to recreate, uh, without having to, to worry about the security of their credit card or, um, some other financial instrument.

Um, or, uh, maybe it's, it's even about, uh, uh, life sciences, like, uh, developing technologies and treatments, um, that. Help people live a healthier, longer life, um, in a way that continues to protect their privacy.

[00:04:31] Simon Vetter: One of the things that stand out on the website is the values, and I love your first value life first. Can you write that and, and how did you come up with this, this value to really make sure that people enjoy life as much as they enjoy work.

[00:04:51] Trent Hein: Yeah, this is a great question. Well, um, this is not, uh, my first rodeo as, as you mentioned, and, and one of the things that I've had the opportunity to do is, is work in much larger, much larger corporations. And for folks who, um, let's just say their mission was all about money, right? How, how did they make money?

How do they make more money? Help their buddies make money. If that is your goal, uh, oftentimes that leads to cutting some corners around quality of life, right? Um, having people work 80 hour weeks or have people work, you know, a 20 hour shift because there's some type of security incident or it incident that has to be fixed.

Or not letting people take vacation. And once you work in an organization like that, um, you, you realize, A, how small you feel and b, how demotivating it is to do anything. You know, you, after, you know, working a 20 hour shift, you come back in the next day. And at least in my personal experience. You just don't care about what the company is doing or what your supervisor wants you to do.

You're like, Hey, I just put in all this time. You guys go, go do whatever you want. I I, I'm not gonna be told what to do going forward. And that's, that's terrible. It's terrible for culture. It's terrible for team cohesion. and so after having lived a few of those experiences, uh, when we founded Rule Four, or one of the things we said is.

That this is not that we're building a family. We're building a family that cares about what we do and cares about what each other of cares about each other, and we're gonna support each other when those life events come up. Whether it's, Hey, I need a root canal and I've gotta leave this afternoon suddenly.

Or, um, maybe I have a sick parent or a sick uh, kid, or I just need a mental health day. I just need to get away from a keyboard for a while. And, uh. Get refreshed and rejuvenated. Um, all of those things are important life decisions, and we have to support each other in that. And it has to come first. That's the, that's absolutely the only way to build that feeling of, um, Hey, I matter here.

My work matters. Um, but most importantly, I as a person, matter to the company and to my other teammates.

[00:07:14] Simon Vetter: What's the impact of that value and how does that show up in terms of the cohesion, in terms of performance, in terms of the, the culture?

[00:07:24] Trent Hein: Yeah. Uh, it, that, it, that is a great question. Uh, you know, we, we've recently had a couple of folks that had gone off to do other things, right? And, you know, life happens. People leave for a variety of reasons, right? Like, you know, my brother's moving the west coast and I've always wanted to, to hang out with him.

So I, I, I move there with him or, or whatever, right? I, I, I'm, I'm, I need to. A move back east to take care of a sick parent. Um, but we've had a couple people come back, um, after being gone for a while. And, you know, the, the thing that they have consistently said is, as I reflected on my time at rule four, um, when.

Uh, you know, I think about all of the things that we did to make life better, to make me better as a person. And that's what I want and that's what I don't have elsewhere. And so, you know, in terms of, you know, we normally frame it as a metric, uh, as employee retention, but really this is, uh, in this particular case, this is like employee boomerang, like folks that come back.

Because we're like, this is a better place to work. And so, uh, that's a super positive impact. You know, the thing I will note though, is that we try to operationalize this in a real way, in that we build processes around coverage, right? Because if you step away for a life of life first event, right? Like whether it's a dentist appointment or I, I, I need to go support a, a, a sick or aging loved one.

Um. You don't want that guilty conscience of, Hey, I'm stepping away from work that needed to be done, work that needed to be done, uh, for another teammate or for a client. And so we build in coverage processes where, um, we're always documenting, Hey, um, what did I do today? What am I gonna do next? Um, and what do I need to know so that if someone has to step in in my place tomorrow, that, that, that data's already there and the person who is stepping away can step away with a clear conscience.

[00:09:23] Simon Vetter: Nice. Nice. I like this concept of the. The boomer on that, people come back and again, it's, it keeps people loyal to the company. It's a way to retain good talent. And when people are well balanced in their life, they show up differently at work and it creates a different environment. Absolutely.

[00:09:45] Trent Hein: hundred percent. Right? And it's, you know, I always tell folks is you should love your job no matter what you do, right? Whatever it is you do, you should love your job. And, uh, we're, we're all about creating that environment where folks really love it here.

[00:09:59] Simon Vetter: You work in a space of, of cybersecurity and tech technology, and there's a lot of innovation. There's a lot of new technological advancement. From your experience, how do you set the vision, the strategy, the direction for the, for the organization, knowing there's a lot of different, uh, elements and, impacts, what's your approach to that?

[00:10:20] Trent Hein: Yeah, so I'm a big fan of this work that came outta Stanford focused on design thinking, right? And it, it really started in the space of, human interaction, you know, human computer interaction. Um, but you know, it's been broadened by a whole bunch of, uh, different folks in. Into designing what you want the experience to be, whether it's a technical experience or whether it's an employee experience or a client experience is. Take all of the data that you know about, what are the, the, the barriers to success? What are, um, the, uh, inputs, right? What are those things that affect how folks perceive the interaction, whether it's human or technical or whatever. And, uh, uh, actually map out a, a, a design, like a storyboard of what does this look like, um, going forward.

From that, if we, if we apply design thinking to, you know, corporate strategy or technical strategy, um, we can end up with again, um, some roadmap or blueprint of what are we supposed to do that's grounded in why are we doing this right? Like that, that we, we actually thought through like these are the reasons why, and this is how we want.

People to feel or experience or this system to work. And so here's the blueprint to get there. And, and I think doing that, um, often we do that in a workshop format in front of a whiteboard. I know that sounds terribly old school. It's like, oh my gosh, they're gonna get in front of a whiteboard. But the quality of collaboration that you get by in-person experience and, and, and being able to scribble, uh, on a whiteboard next to folks, uh, I think just exceeds anything we can do even with the, the most amazing online collaboration tools.

[00:12:09] Simon Vetter: What is the experience you want your clients to have as a result of, of strong cybersecurity measures?

[00:12:20] Trent Hein: Uh, I want them to sleep at night. Like, that's the, that's the, that's the number one thing, right? Is, is like, if we have people, uh, who, who, who, who are, uh, concerned about, uh, taking an inordinate amount of risk, um, in their organization regardless of what they do, um, uh, to the point where they're uncomfortable or, you know, they're literally not sleeping at night.

That's unacceptable, right? We, we, we are in a space where. There's no zero risk position if you're handling information electronically. There is some amount of risk, but we need to make sure that we, well understand that and that we're, we're mitigating that. Like how, how do we get to a, uh, a, a tolerable risk level?

Um, that's well understood and that we've also put controls around, um, that if something should go, uh, not as we would want it to, um, that we can always recover from it.

[00:13:12] Simon Vetter: So it's about peace of mind and feeling safe and secure. Now, I come from Europe, and when you go to Europe 500 years ago, they had those big. Hassles and they built a big with, with deep, uh, deep water, um, um, around it to protect themselves to be safe. Now we are in this digital space and we can get attacked anywhere.

What are the biggest threats that we have to pay attention, um, around dealing with our data and, and digital information?

[00:13:51] Trent Hein: Well, that's a really broad question. I mean, I guess I'll start with, the best way to secure something is to not have it right? So if, uh, we have data maybe that we use as part of our business, um, as let's say for a transaction that maybe once the transaction completes, um, the data is no longer.

Directly useful to us. Um, we, we should get rid of it. We should expunge it. Um, because any data that we have sitting around presents some risk to the organization regardless of what data it is. And so. First and foremost, let's get rid of data that we don't absolutely have to keep or keep it for the, the minimum retention period.

Um, you know, the, uh, the, the, the next thing I'll point out and, you know, straight out of the cybersecurity textbook is user behavior. Um, so a very large percentage of the incidents that we encounter today, um, are the result of a user that. That didn't do the right thing. And my experience is that in most of those cases it's 'cause they didn't know what the right thing was.

Like. If we can educate and train users on, Hey, this is, this is what you need to do, this is how you need to protect data, or how you need to follow a process that. More often than not, they'll try to do the right thing, but if we don't communicate what the right thing is to them, for sure, we're gonna get just random results and we're gonna end up with some security mess at the end.

[00:15:12] Simon Vetter: yeah. Because we get attacked everywhere from all angles. And so, so it's also a, a cultural thing because you, you teach good, safe behaviors from the users. How do you establish that culture for your clients? How do you make sure that you minimized and mitigate that risk?

[00:15:32] Trent Hein: we have to look at both sides of it, right? We have to look at the administrative controls, which includes user, uh, uh, awareness, as well as, um, behavior management. Um, but then we have to look at the technical controls, like how is the environment architected? Um, how are we monitoring it? How are we making sure that it's recoverable and that full set of things Right, which we would typically call a cybersecurity program.

Um, you know, it is this combination of administrative and technical and operational controls and, um, unfortunately, I think one of the things that has happened in the last couple years, maybe more than a couple years, is that the. Protection around, uh, validating that all of those controls in place has fallen to, um, the audit realm.

And there's a lot of what I call audit theater going on where, uh, folks know they're supposed to be audited. Maybe on an annual basis. And they have a whole team that manages that audit. And the team gets very, very good at showing the auditor what the auditor wants to see and making them go away. And then the auditor produces a report that says, thumbs up.

You guys are doing a great job. But the reality is what that auditor should have been doing, um, is really digging in and being that that. That person that tells you, Hey, uh, I know you're about to go out on the town tonight and you've got spinach in your teeth. Um, you're gonna have a much better night if, if you fix that first.

And, and, and that's really what we should be doing with that audit cycle is we should be welcome welcoming them into the environment, um, to really dig for those things that. Aren't present or aren't operating appropriately, so that then we can fix them before the attackers find them. And unfortunately, um, the, the whole cybersecurity industry has gotten kind of wrapped around the axle with a whole bunch of audit theater.

[00:17:25] Simon Vetter: Yeah. Now AI is changing, the world's changing our work. And you, you said at the beginning, we all start with what kind of experience do we want the users or the the clients to have? What do you see from what you know? How will AI change our experience, how we use it, how we work together, and what, what's your perspective?

[00:17:53] Trent Hein: Yeah, it's, uh, it's interesting 'cause in the cybersecurity space, it cuts both ways. Um, it's a fantastic power tool for us to be able to, uh, find vulnerabilities or perform audits or, um, model particular scenarios in an environment like, you know, the, the, uh. Force multiplier that we get from AI is, you know, something like fivefold or tenfold in terms of our ability to, to really understand the security of an environment.

Um, but the flip side of that is that the attackers who are also using ai, um, uh, can find those same v vulnerabilities and they can exploit them much faster. So, uh, you know, there's this, this, this clock, you know, of a theoretical clock that's ticking in terms of. How fast can a new vulnerability once it's discovered, be exploited by an external party?

And if you turn the clock back to, you know, six, seven years ago, it was like two or three years from the time of, uh, typical vulnerability was discovered to the time it was exploited by a hacker. Um, the current projection is that that will be down to one minute by 2028. So. One minute. Right now, we expect that to be about an hour in 20 26, 1 minute in 2028.

And so that's gonna change our world. Um, all of our worlds, not just corporations, but as individuals. Um, the need for us to be vigilant about updating devices, patching devices, handling devices securely and handling data securely. Um, it's just a whole new world. The pace that we're operating at in cybersecurity is, completely different than we were even three years ago because of ai.

[00:19:37] Simon Vetter: That's amazing. One minute. Yeah. We gotta really, yeah, it's scary and so we really need to be prepared and, and putting the, the right measures. Otherwise the damage can be. Yeah, very damaging. Um, so going back to a vision, um, you have a vision for your organization, uh, what is it, and then how do you ensure that you use it as a filter for important decisions?

[00:20:08] Trent Hein: Yeah, I would say there's two, uh, foundational components. Um, one is doing good in the world, and so, uh, that means that for every client we take on, uh, we actually do an internal assessment of how does that client do good in the world. Uh. Um, and you know, there's a lot of businesses, and I'm not gonna name them here, but there's a lot of businesses that I'm sure we can all identify as like, yeah, I get that.

That's a business. It's not a business that I really wanna be associated with. I don't think that that's a good thing or that it makes the world a better place. Um, we won't take on those clients. And we've, we've made some hard decisions. We've had some pretty, um. What would've been large and profitable deals, uh, in front of us.

And, uh, we made the decision solely on of, yeah, I, I don't, I don't wanna do that. That, that makes me feel dirty, that that makes me feel like I'm not doing good work. Um, and so, so we do use that as a filter. And the other thing I'll note is team size. Um, uh, as I mentioned earlier, I've had the opportunity to work in some pretty large organizations, um, uh, hundreds or thousands of people, and.

One of the things that I've noticed is that when you get team sizes above, I don't know, somewhere around 40 or 45 people, it becomes a completely different animal. It's not a family, it's like a political system, and so. I don't, and I don't wanna play that game, right? I wanna do good work. I wanna be focused on what we do technically and be the best at what we do technically.

Um, I don't have time to play politics and I don't want to play politics. And so we're very intentionally size constrained in terms of our staff, is that we wanna be in that, you know, 40 to 45 person, uh, range, max, uh, so that we don't end up in that state.

[00:21:47] Simon Vetter: Yeah. Now having worked in big companies and, and I often work and coach executives in, in large organizations, thousands or multiple thousands of people, what do you recommend based on what works for you? Would you recommend those executives? How do use clear intentions? To create a high performing, high function culture and make sure people wanna be there and do good and deliver results and good profits.

What do you recommend? I.

[00:22:20] Trent Hein: I, I think it's always fair to challenge people with the question, um, you know, how does that make us better? And whether us is the company or our, our, our executive team or, uh, you know, the. The space that we're in, you know, how does this make us better? Whatever decision we're trying to make, whatever initiative we're trying to push forward.

Um, if folks can't answer that question, A, we have a pretty big problem. Um, and b, we're gonna end up with the wrong result every single time. Right? Um, because you can micromanage folks and be like, oh, do this task, or this task and this task, and if they don't understand the bigger picture. Why it matters, you're gonna end up with a mess.

And so, uh, I, I think in any size of organization, that is a fair question.

[00:23:06] Simon Vetter: Yeah. And then better is also a matter of interpretation, and it's good to have a discussion. What does better look like? What is it? What's the impact of better? And then who do we wanna better? It's. Our own team, our own people. It's the client, it's the stakeholders, it's the environment. So I think that itself creates a lot of questions to determine what that ultimate purpose and direction is.

[00:23:36] Trent Hein: Hundred percent. Yep. I agree.

[00:23:38] Simon Vetter: From your experience, what has worked best to gain clarity around those questions? And what are some things that you found that, They were made mistakes that you wanna avoid.

[00:23:51] Trent Hein: there's an exercise you can do and, and I think this actually comes from the, the Google Ventures folks, um, uh, called Crazy Eights. And so, uh, often what I'll do with the team is, is you take just a regular piece of paper, eight and a half by 11 piece of paper, and you fold it so that you have 8, 8, 8 rectangles as a result.

Um, and, and ask folks to spend a couple minutes, um. Filling out each of the eight squares, rectangles, whatever they are, um, filling out each of the rectangles, um, with an idea of, uh, what, what does this look like? Like what does this look like in, as you said, when it's better or when it's good, you know, depends on, uh, what you're actually trying to solve.

Um, and, and do that in a very time box format, right? So you've got five minutes to fill out these eight squares. Ready, set, go. And it forces people A, to focus and b, to think about the problem from more than just one side. Right? In fact, it makes them think about it from eight sides. Um, and usually that forces this discussion of, oh, okay, there are other ways to look at this and understand what are the various impacts, um, uh, or, uh, what are the various results we wanna get?

And so that. That crazy exercise, which you can do with any size of team in five minutes, um, always produces fantastic discussion.

[00:25:12] Simon Vetter: I like the question, what does better look like? Or what does good look like? Or what does success look like? And people create different ideas and perspectives. Once they create all those ideas. How do you facilitate the conversations to create the consensus?

[00:25:28] Trent Hein: Yeah. So, uh, it, it depends on the size of the team and of course the personalities. But, um, what I typically do is I ask people to present them, right? Tell me, tell me about the things that you put in your eight boxes. And, uh, you know, most folks, as they do that presentation, we'll start to tell a story, right?

Why it matters to them or why they think box three is the most important one to think about. Um, and. To do that in a group setting. And again, I'm a big fan of trying to do it in person. Um, uh, really helps that cross pollination of ideas across team members.

[00:26:04] Simon Vetter: Do you have an example how you applied this exercise and have gotten some amazing outcomes?

[00:26:10] Trent Hein: Yeah. So, one of the things that we did three years ago is we moved from five day weeks to four day weeks. And, you know, you would think like, oh, that sounds amazing. I have three day weekends, uh, every, every, every weekend. And, um, uh, no problem. We'll just squish the week into four days. Um, you know, as it turns out, it is not nearly that easy and there's a number of, of, uh, great.

Research papers, um, and writing on this particular topic, other organizations that have done this. But the, the, the thing that wasn't immediately apparent to us is the operational impact of taking five days, putting them in four days and making people feel like they still have space to breathe. Right. And that is a weird thing to say, but that is consistently.

The feedback that we've gotten from this shift is that like, Hey, yeah, everybody loves three day weekends. No one will debate that with you, but the remaining four days, it's like, what does that feel like? And if it feels like you, uh, just tried to put, you know, 10 pounds of flour into a five pound sack, um, that is not a good feeling.

And so I'm doing that kind of brainstorming with a, with a. People across many roles and have them articulate like, well, why does it feel this way? Um, how can we make it better? What does this look like in the right state? Um, a gives everybody a. Input, but they also get the opportunity to see like, okay, I understand now why, you know, Steve feels this way.

Um, but Susan doesn't, um, that discussion is important. And so that type of facilitation for a problem like that, um, is really great with a group.

[00:27:50] Simon Vetter: Yeah. Now you founded a, a couple of tech companies, so from your experience, what is the skillset and or mindset necessary to successfully build a company in the technology field that kind of thrives and builds stability and builds momentum? What have you found are the, the, the key components of, of the mindset and skillset?

[00:28:15] Trent Hein: I think you have to be a little bit deaf to external feedback at the beginning. Um, yeah, I think back to, um, 1991, um, when, uh, I started my, my first company here in Boulder, um, at the time, you know, Boulder's a great. Place from a, you know, outdoorsy and, um, weather's great here and so on. Um, but back in 1991, there wasn't this, you know, data network focused, uh, sector here, right?

Like there was a lot of whole, um, um, natural foods and, uh, there was a lot of pharma. Um, but in terms of just. Pure, what we would call tech today. You know, this was before the commercial internet. Um, um, it wasn't here in Boulder. And, and I was like, well, I don't wanna leave Boulder, but I wanna start this company.

And so many people tried to talk me out of it, right? Like, uh, multiple mentors were like, oh, you'll never succeed that you have to move to the Bay Area if you wanna do something like that. Boulder's not the place for this, uh, the internet thing. It's away in a, um. I, I, I know that they were all well intended in their feedback.

Um, the, the reality is I'm really glad I didn't listen to it because, um, you know, there's opportunity to have that vision and say, no, there, there we can build a company, um, that's, that's focused on commercializing the internet and, and putting traditional brick and mortar companies, uh, into a digital space.

At the time that was. Completely unheard of. And you had to have the vision to get past that. And, and I think the true, the same is true in cybersecurity, right? When we look at, uh, even just 2018 when we founded Rule four, um, folks are like, well, you know, there's a, there's a lot of cybersecurity products out there.

And we're, we're quickly approaching the time. I actually had someone tell me this. We're quickly approaching the time where, where you'll just be able to buy a box, um, and plug it into the wall and that'll be your security and you're done. Nothing could be further from the truth, especially as we look at a world, um, that's very in AI enabled going forward.

Um, you have to not listen to those people who think you're gonna fail. You gotta just believe that this is where we're going. Have that vision and make sure you communicate it clearly.

[00:30:33] Simon Vetter: How did you develop that vision? Where did you get the insights and the right signals to create that path forward? where did you get those inputs?

[00:30:44] Trent Hein: Yeah, it's a good question. I, you know, I try in general to do in my work life the things that I personally love and I'm excited by. And so when I look back to 1991, um, you know, I'd been, uh, doing a lot of work with the internet in research environments and university environments. And I loved it. I was like, oh my gosh, there's so much potential here.

And, and it, it's, I, you know, certainly was, uh, amazing for the research and university community at the time, but I, you know, I wanted more. I, I wanted that, I wanted to be able to reserve rental cars online without having to sit on hold with an 800 number for. Uh, 30 minutes, right? And if you think back to the early nineties, that was the model.

If you had to reserve a car, you were gonna sit on hold with an A one 800 number. Um, no one would do that today, right? Folks use a internet browser to do that. Um, and so I was passionate about that. And the same thing comes to, to modern times with security and privacy. I am, uh, passionate about. Uh, individual privacy and, uh, protecting data and using data for good, and that naturally feeds into, okay, cool, if that's what I'm passionate about, what do I want to do as business, um, to, to spread that love of security and privacy.

[00:32:00] Simon Vetter: Yeah, and I think when, that personal passion, those personal interests align with. The business. I think that's where there's a level of motivation and energy that gets, uh, unleashed.

[00:32:13] Trent Hein: Oh yeah, right. I could talk about, as you can probably tell, I could talk about this stuff for hours. I just absolutely love it and I think it's fun. Like I have fun, you know, a, a any job you have a couple days once in a while that aren't fun. But I have fun 98% of the time here, and that's motivating I, that, that gets me out bed every day to go do fun things at work.

[00:32:35] Simon Vetter: Yeah. Now again, in in the, the current environment, everybody talks about ai, but there's so much uncertainty. We don't know exactly how it will evolve. What will be the ultimate impact when there is that unclear environment? How do you communicate the path forward? How do you communicate the vision that still inspires people and give them a sense of of confidence.

[00:33:07] Trent Hein: We always have to focus on, um, you know, what, what do we know today? Right? Here's, here's the, the good aspects and here's the maybe not as good aspects of a, of a particular situation today. Um, and then be willing to reevaluate that, uh, you know, on a. Weekly basis on a daily basis. Um, whenever information changes, you know, we've, in the cybersecurity space, I'm sure people have followed in the last couple weeks, um, uh, the, our friends at Anthropic have, uh, provided a lot of data about, uh, how AI might impact security cybersecurity, um, or how it will impact cybersecurity here in the, the coming months and years.

We all knew that that was coming around the corner sometime. Um, it's here now. And so it's, now that it's visible, um, we have to talk about it and talk about, well, what are the good parts of that and, and what are the things that are not as good? And just be completely transparent, um, and adapt, make changes to, uh, processes.

S is offering, um, uh, procedures, uh. Organizational structures, make those quickly. Um, you know, this is also where I think, um, big industry sometimes struggles, is that they're slow to adapt to change like that. And that's, that's why small business sometimes, um, uh, can be more successful in these cutting edge areas.

[00:34:31] Simon Vetter: What are the big important questions we need to ask around ai?

[00:34:37] Trent Hein: I think it really comes down to, um, what is the, uh, integrity and mission and vision of the organizations that are, um, providing these platforms to us. And, and, you know, we've, we've, we've certainly in 2026 this year, um, seen a, a, a pretty wide spectrum of that. Um, in that we've, we clearly have some organizations today that, um, have a value space.

Mission and are sticking to it in, in business decisions and technology decisions and deployment decisions, disclosure decisions. Um, and then, uh, we have other players in this space that, uh, seem to maybe a little more focused on, um, uh, the almighty dollar, um, rather than, uh, a particular, uh, mission or, or, uh, value set.

And, It's interesting because we can take what we know from humans, right? It is like if you grab a, a particular human and get to know them or you know, have, have a beer with them, you can pretty quickly pick up on, you know, what makes this person tick? What, what are their values? Um, uh, will they hold to them?

Are they, you know, or, or are they easily swayed by other influences? We can take that. Same model and apply to ai, right? Because what is ai? AI is uh, basically, uh, machines operating as humans. And so if we have this machine operating as a human, um, if I have a beer with it, does it share my values? Does it share my mission?

Um, does it share my integrity? And, and I think we have to continue to answer those, to ask those questions and seek those answers, especially as, These platforms, which are cool and useful, but become absolutely ubiquitous aqua across all of our daily lives.

[00:36:27] Simon Vetter: Yeah. Yeah. How do we say grave guards? And again, it goes back to what's the intention and what are the agreements that we are willing to support and, and what is okay and what's not okay.

[00:36:39] Trent Hein: Yep, that's exactly right. Yeah. And make those decisions. And then just like in real life, right, where you're someone like, Hey, you know, that, that person, uh, my daughter would say, uh, that person doesn't fill my cup. Um, uh, is is that, you know, if we find someone that just doesn't fit our view or our values, um, maybe it's time to, to be a little farther away from them.

And we need to make those same decisions with AI platforms.

[00:37:04] Simon Vetter: And be willing to walk away and sometimes. Walk away and knowing that we might not get the financial benefit and, and that's the trade off we have to make.

[00:37:13] Trent Hein: Hundred percent. Yep.

[00:37:15] Simon Vetter: Yeah. What did you learn as an entrepreneur and that impacted you in a positive way and what, what did you learn about being an entrepreneur leader?

[00:37:25] Trent Hein: yeah, that is a good question. Um, uh, you know, I. I, I guess that it's cliche, but the thing I would say is that anything is possible, right? Is that if you take the reins and say, I'm gonna go build my own business, you get to build it the way you want, and you get to hire a team that you love working with and you get to do the projects that you love.

Um, and. Uh, you know, I, I, I think that's just an in incredibly important lesson, and that's when, when folks come to me and they say they, they get that first sentence out that they're like, Hey, I'm thinking of starting a business right before they even explain what business it is. My, I immediately say, do it right?

Like that is the thing. Like, go be empowered. Um, go carve your own path. And I, I think that's probably the most important lesson.

[00:38:15] Simon Vetter: Yeah. And then how, what do you recommend in terms of developing that visionary skill to see ahead? That it's one is the, the energy and the motivation, passion we need, but then also the direction where we are going. How do you advise people to pick the right direction? To make the right decisions?

[00:38:39] Trent Hein: Yeah, the, the thing I always say is, um, do the thought exercise of, you know, imagine you are three years down the road from today, and you look back, right? You look back and, and you want to describe like, what does that three year journey look like and what did I accomplish in that three years and. That is the exercise.

I think that helps form that vision skill. 'cause then you're like, okay, if three years down the road I want it to look like this, then I can start to build that sequence of steps is how do I get there? And, you know, I think, I think that's good in entrepreneurship. I think it's good in life, um, to do that exercise once in a while.

Be like, okay, I, I'm three years down the road, I'm three years older now. I wanna look backwards at today. And, and what do I see?

[00:39:28] Simon Vetter: Yeah. Uh, Stephen Coving, his book, uh, has seven Habits of Highly Effective People. One of them is called Start With the End in Mind. And it's really around three years from now, or even one year from now, or if we have a, a meeting coming up or we have a decision coming up, what is it? Looking backwards?

What's the outcome look like? Call it case scenario, that we create a best case scenario of the future and sometimes when we are not intentional, the mind automatically creates a worst case scenario.

[00:40:07] Trent Hein: Yes, yes, totally. Yep. Yep. And so it's like, let, let's, let's, let's pick, let's make that path that we want, and then all the other paths fall away.

[00:40:15] Simon Vetter: Yeah, yeah, exactly. Fantastic. any tips or recommendations for the listeners from your experience around creating companies, creating a vision, creating a culture that, you like to give, uh, to the listeners?

[00:40:31] Trent Hein: You know, the, the thing I think that's helped me, um, that I often share with folks is you should always curate a good set of mentors, right? And it, uh, whether it's mentors in your business life or your personal life, um, have that set of people that when you look at them, you admire. A particular skillset or aspect of them and get to know them and, and have them help you.

Right? Folks like to be asked for help and if you have a good set of mentors, you, you can really get through anything, right? They'll be by your side in the good times and by your side in the not as good times. Um, and I think it's just incredibly important to have that and have that set of mentors that's, that's outside of your current work environment, right?

It's like, of course we. All have great, um, relationships and friendships, um, in our work environment, but having those folks with outside perspective, uh, I, I think that's key to, to personal growth and to, to be able to take that next leap.

[00:41:26] Simon Vetter: Who was your most influential mentor in your career at.

[00:41:31] Trent Hein: You know, I'm gonna, I'm gonna, I'm gonna, I'm gonna name two people. So, um, uh, uh, uh, one person, uh, is, uh, Dr. Evie Nema. So she, uh, uh, is computer scientist. Um, uh, taught at a number of universities, but most recently at, uh, the University of Colorado. And, um, you know, the thing I would say about Evie, uh, is that. Even though she is, you know, 30 some years older, she could always run circles around all of us at anything, right? Like whether it's cooking chicken or drinking wine or solving a hard encryption problem, um, uh, she really, uh, demonstrated that age doesn't matter, right? That, that no matter what. Calendar problem you had in front of you.

Um, uh, she absolutely, uh, would kick everybody's butt at doing it. Um, and you know, unfortunately, uh, uh, as Evie retired, she, uh, was living her dream, uh, sailing around the world, um, and, and was lost, uh, in the Tasman sea, uh, on a sailboat, uh, back in 20. 13 or so. So that, uh, tragic loss for Evie, but I know that she was living her dream.

Um, my other mentor, um, uh, that I'll name, uh, uh, is actually I, I, I think Simon, how you and I connected, um, Albert Orle. And, um, you know, I, I've had the, the pledge of working with Albert over a couple decades, um, in a number of different environments. But, um. Albert really taught me how to inspire others through education, um, and how to always communicate transparently that, that, uh, he has a special way about him of even in the most difficult situation of being able to explain something in a way that, um, uh.

Is transparent and honest, and, and folks see it as, Hey, you are helping me by explaining this particular problem or situation. he's just really inspiring individual to get to hang out with.

[00:43:33] Simon Vetter: What I like about Albert and he introduced us, um, he's calm. Confident demeanor. just feel comfortable in his presence. It makes you feel like you can drop your shoulders, you can be transparent with him. So there's something about his energy that is very inviting.

[00:43:52] Trent Hein: Yes, yes. And, and he always, he always has a, has a solution. Uh, when you present him with a challenge, he, he always has a solution of, you know what, let's do this. And it's just dead on. Just, uh, amazing skill to do that.

[00:44:08] Simon Vetter: I totally agree. I think mentors are so important. Uh, we have people who a perspective and a caring about growth and reaching out and ask them to support us. I think that's a, it's a important aspect. Thank you so much, Trent. It's been amazing. Uh, where can we find you?

[00:44:27] Trent Hein: Uh, you can always, uh, uh, find me on the, the internet via email Trent at rule four. That's RULE and then number four.com. Uh, drop me a line. Uh, I love to chat with people and as you can tell, I love to talk about this stuff. So thanks Simon. This has been amazing.

[00:44:41] Simon Vetter: Thank you so much. I appreciate your time and your insights. Have a good one.