He got rejected by 60 VCs, burned all his savings—then grew to $100M ARR & a $2B valuation. | Kyle Hanslovan, Founder of Huntress

Kyle left his job as a hacker at the NSA to launch Huntress. He bootstrapped for 3 years and burned all his savings. One of his co-founders quit. He got into an accelerator program, but had to sleep in his car for 16 weeks because he couldn't afford a hotel.

Finally, 3 years in he'd hit $1.5M ARR. So he pitched 60 VCs for a Series A—and got 60 'no's. He was forced to raise a small, $1M inside round. 

But then things changed:

2018: $1.5M ARR
2019: $5M ARR
2020: $10M ARR
2021: $20M ARR
2022: $40M ARR
2023: $70M ARR
2024: $100M+ ARR

Huntress is valued at $2B.

The investors who backed his $1M bridge are up 140x. 

Now every VC wants to invest—and Kyle's the one saying 'no'.

Why you should listen: 

• How to know whether you should keep going or quit.
• What it takes to get through the first few years at a bootstrapped startup.
• Why revenue expansion is a huge lever for fast-growth (Huntress has 140% net revenue retention).
• How starting a startup can impact your personal life and relationships.
• How to work with partners to sell to long tail SMB customers.

Keywords
entrepreneurship, cybersecurity, product market fit, startup journey, military experience, SMB market, funding challenges, automation, human expertise, business growth

Timestamps:
(00:00:00) Intro
(00:2:01) Working at the NSA
(00:6:14) A big win in counter cyber terrorism
(00:10:00) What gave way to Huntress
(00:14:22) Pitching to a startup accelerator
(00:16:29) Adopting curiosity
(00:21:04) Getting ahead of cyber criminals
(00:26:00) Starting to grow
(00:32:50) Cult or conviction
(00:35:00) It takes grit
(00:39:50) Learning from people's lessons
(00:42:20) Cockroaches and underdogs
(00:46:10) Three strikes, I'm out
(00:52:56) Having a military background
(00:56:17) One piece of advice

Chapters

• 2:01 Working at the NSA
• 10:00 Huntress origin story
• 14:22 Pitching to a startup accelerator
• 26:00 Starting to grow
• 32:50 Cult or conviction
• 35:00 It takes grit
• 39:50 Learning from people's lessons
• 42:20 Cockroaches and underdogs
• 46:10 Three strikes, I'm out
• 52:56 Having a military background
• 56:17 One piece of advice

Transcript

Kyle Hanslovan (0:0)

three years of hustle, bootstrap, taking every dime, side jobs. We largely had to burn all of our savings. It got so bad that at our 16 weeks, I slept in the back of my car in this secure facility. And thankfully they had a gym so I could shower. I was told no by everybody. 60 plus no's and sometimes you're an idiot no. We were just so small, nobody knew who we were. They didn't believe that the numbers went from 1.5 to 5.3, 5 to 10, 10 to 20, 20 to 40, 40 to 70 and change 73, I think. And this year we've just sailed past a hundred. It's nuts. 

Pablo Srugo (0:40)

Welcome to the product market fit show brought to you by Mistral, a SeatStage firm based in Canada. I'm Pablo. I'm a founder turned VC. My goal is to help early stage founders like you find product market fit. Kyle, welcome to the show. 

Kyle Hanslovan (00:57) 

Dude, thanks for having me.

Pablo Srugo (0:59) 

Man, so you just had some pretty big milestones happen. I mean, you raised $150 million a few months ago, which is always huge. But I think bigger than that, you crossed the magic hundred million dollar ARR milestones. So first off, congratulations. That's for me, the biggest kind of startup milestone and most important one you can hit.

Kyle Hanslovan (1:16)

 Yeah, the right valuations come and go. Sometimes the market super inflates these, but you can't usually lie about revenue unless you're preparing to go to jail. So I'm pretty pumped. A hundred million was a huge kind of both validation mark, but also, you know, it puts wind back in your sails, right? You're doing something that matters that people care about, you know, that money didn't come free. So I'm feeling pretty, pretty stoked.

Pablo Srugo (1:40)

 We'll jump into kind of, know, you've been at this for nine years at Huntress. So we'll go to the beginning, the origin story and all that. But before that, I want to go nine years before that, cause you spent nine years in the NSA, right? doing cyber warfare stuff, which is intrinsically just cool shit. you're good. If you could just tell us a little bit like, what is that world like? What were you doing back then? 

Kyle Hanslovan (2:01)

Yeah, so I was a punk kid that was looking for opportunity and I listed in the military into the Air Force at 17. And at that time, I was already pretty good, pretty scrappy, you know, doing shady stuff on AOL and writing software. What was nice is even though my first three years were pure Air Force, I got to start doing a lot more intelligence work after that. so between my active duty time and national guard time, I did 13 years with NSA. And that time was all one thing most people don't talk about, even though it's not classified, just some folks get uncomfortable is, NSA is an intelligence unit charged with protecting national security through signals intelligence. That means somebody out there is collecting sexy signals. And even though, like, if you look at my resume, you'll see the words like, I created implants. It's just a fancy word for I was creating the software gathering tools to be able to gather that intelligence when we did earn our way into a network. Or I guess if you were on the other end, you would say hacked the way into the network. So it was pretty cool. And what a lot of people don't realize is these teams that do clandestine operations. You watch movies, it feels like instant gratification, but they're actually these very small, compartmented teams, usually your coworkers don't know what each other's working on. And maybe the sexiest part about it is how small of a team can go after maybe a target that's equally small, needle in a haystack. Think of a counter -terrorist threat, or maybe just the right data you need to know about another country's foreign nuke policy or whatever you're targeting. And how can you use tons of automation despite being a very small team? So that's where things like AI wasn't very hot when I was in it, but it was all about statistical analysis, frequency analysis, core math principles. And so we got to use that combination of shady hacking skills plus massive amounts of data science. And it kind of kept me really stoked. 

Pablo Srugo (3:54) I know you can't talk about the specifics you did. So almost like talk about something else, but just give us a sense,  from somebody that's totally not in that world,  what sort of things are you doing to find what kind of information?

Kyle Hanslovan (4:06)

Yeah. Yeah. So I'll give you just a good example of what we see in the current landscape and you can kind of put two and two together. So right now, you know, almost everybody said you need to have a complex password. You must have this, that, and the other. It turns out it is so easy now for hackers to gather your password. They dump this data in mass. So a good example,  I would create tools to be able to gather, for instance, credentials. And  nowadays, when we type into a website, we save it into the browser and it says, yeah, I'll save it here stored for you. The problem is if your malware is also running on that same browser, it's not hard to say, please give me all those usernames and all those credentials and anything else that's stored. And even though it's encrypted, since I'm running as you and you have to be able to insert into websites, I can decrypt it. And so what happens is when you end up with that type of data,  you see nowadays, even figuring out the signal and the noise, right? There's a lot of garbage passwords. I don't care about your kids Roblox account, right? I don't care about your silly, I don't know, maybe you're a subscriber to Vogue magazine. What I want are the keys to the castle, right? And that's usually like credentials that maybe log into your multifactor. Maybe that stuff that logs into , I always love Microsoft 365 and G Suite, right? Cause so many of those, when you log in, you can log into multiple other websites. And so even how do you find out when you have so much data, how do you truly figure out what's the signal and noise means you can't just collect it. Like the job isn't done until you actually, you know, protect national security. So half the problem is getting it. The other half is what can you do with the information that you have? And then also you don't want to collect information you shouldn't be gathering, right? That's a huge part of it too. So, it was wild. It was a good time and you can imagine most people go to jail for doing shady stuff like that. I was really fortunate to not only -, I loved my time in the service. I learned a whole lot from it, but it really helped me bootstrap the ideas for Huntress too. So it was, you something I'm  kind of eternally grateful for. 

Pablo Srugo (6:10)

You know, big win in the startup world is like landing a big customer, closing around.  what's a big win in that world? 

Kyle Hanslovan (6:15)

Ooh. So I'll tell you , stuff that people don't talk about in modern,  cyber warfare is when you're doing your job, especially on counter -terrorism,  the most exciting part of your job might be, Hey, you gathered intelligence that for instance, could preemptively save life. But I will tell you, for every one of those moments that you have those, you have moments that you're late, or you gather only a fraction of the one side of the story. And I will tell you, they come with some really rough moments on your soul too, where you're like, whoa, life was lost because we didn't do it well enough. Or maybe the real morbid side is like, if you're going after people,  especially terrorism is such a closer to black and white instead of like nuances of espionage. And imagine that world where it's black and white and you're like, okay, I gotta gather this intelligence on this person, but by you gathering that intelligence on that person, the kinetic side of the military does what they call a kinetic uninstall. That means usually they dropped a bomb on a bad guy and then you have to kind of live too. Like you're doing your job in cyber warfare. And so I'll tell you the best days where the days lives were, you know, saved but it also might've meant like somebody else lost their life that day. And I'll tell you , that didn't dawn on me. Like I started out a little bit more on  forward intelligence and then I got to support counter -terrorism and that was a pretty big shift in mindset of knowing like, whoa, I'm making a difference. it was part of what led me to , you know, after, you know, 15 years or so, 13 years at NSA, I started asking, how could I use my skills for good? I was just always hacking things. I didn't really have a huge challenge of getting into things. And I thought, maybe I should be using these skills to help defend instead of just break into things. 

Pablo Srugo (7:58) 

That's a good segue. Like how do those thoughts end up with you actually moving out of there and then starting Huntress? 

Kyle Hanslovan (8:05)

So they always start with cute ideas. So they were stepping stones. So I actually loved my work at NSA, but part of the mission change that I was supporting, I decided I was going to leave as a, we call it a blue badger. That's somebody who is a government employee. And I started becoming a contractor for a little while. And during my time as a contractor, I managed to get good pay, but it really was me filling like butts in seats, you know, supporting the mission, making good money, but it wasn't like that personal itch that I need scratched. And so I started thinking through, , if my job was  lurking in these networks undetected for so much time, how could I catch other people who were trying to do my job? Right? And even more importantly,  people forget when you're gathering intelligence, sometimes many countries are trying to gather intelligence on the same target. So we sometimes might know that other adversaries could be on the same exact computer and we would see them and we’re going, “we know they're there, but they probably don't know we're here.” Right. And some of that's hubris too, right? You don't ever want to get caught. But, I will tell you that started making me realize  even some of the best hackers in the world can make mistakes. And so what if I took this idea of finding people that dwell in networks, finding their footholds that they just kind of lurk undetected, could I make a product that complimented preventive technology, right? That's that whole  ounce of prevention is worth a pound of cure. But if you think about  in medicine, preventive medicine is like early detection, right? It didn't mean it stopped you from getting sick. They found it before it became  terminal and killed you. So that whole like idea was like, okay, man, can I go? and lurk on these computers and find somebody, even though they made it past prevention, could I find it before it escalated, before it got terminal? And that was an idea that most people thought I was crazy. These companies were all  funded multiple billions of dollars in revenue. Valuations were definitely over a billion dollars. Even for the startups they had raised, know, like, Silance had raised a hundred million dollars or so. And I'll tell you, that moment for me was a really good moment because it made me get really focused on who I was going to protect. Cause if I was just going to be another enterprise vendor,  there wasn't enough green space in that world, right? It wasn't a niche market that I could make my own. And it was kind of the moment that made me realize I had to switch up my plan. So that's what gave way to Huntress. 

Pablo Srugo (10:28)

You know, this is one of the interesting things and I'm sure I'm not the only one, but  for somebody that's not an expert in cyber, a lot of these cyber solutions and  competitors that you would have mentioned  at the time, frankly sound the same. It's like threat prevention. you know, you know, it's just  cybersecurity,  secure your network, you're like, what's the difference, right? So , when you're looking at it, as an insider, what gap do you see you talked about prevention versus cure kind of maybe at a high level, but like, maybe if could drill down a little bit, like, what gap did you see in that cyberspace that you felt like wasn't properly being addressed? 

Kyle Hanslovan (10:59)

Yeah, so just like, you know, a COVID was a good example, we all thought we could, you know, and Not getting political at all, but we thought we could get vaxxed and ideally it would stay the same. But the reality is like the virus mutated, right? It had different versions and some vaccines were more effective. Some people were more susceptible. It's just a complex problem. And it turns out hackers and malware are also complex. What most people forget is that unlike the natural world, like if I tried to shoot a rocket right now, oftentimes we slingshot it around the moon. The gravity picks it up and sends it back and you know, predict where it's going to land. That's how we get folks back and forth between like the space station. The difference is the moon isn't trying to move. The space station is moving, but it's constant. It's not just like jumping here, there, everywhere. Most people forget cybersecurity has another human on the other end that their whole job is to mutate just like that, you know, COVID virus. And so every time you see something, it might be slightly different. And if it was just different and enough to be able to slip past all those like really well done patterns that it was looking to find bad stuff. And even if it was bad and could slip by, the idea was, well, they still have to get inside, figure out just an immune system. Let's attack the heart, right? Let's attack the lungs. It's got to figure out the stuff, for instance, to deliver the damage. Well, in these businesses, you got to find the data. You got to understand how the system, you might have to go from a normal user privilege to an admin and all those like, even though like the mantra In 2015, when we started the company, was like, hackers only have to be right once, defenders have to be right always. And I thought about that inverse and I was like, wait, hackers only have to be wrong once for a defender to succeed. And so my whole idea was I was going to find what slipped past the behaviors, these footholds, things that I used to do when I slipped in. And my idea was not only do I do it, at a level, for instance, that was technically superior, because that's a little bit hubris. There's a lot of smart people out there. You can't assume you're the only one. I realized that there was a whole segment of the market that was being ignored. And it was these companies like my mom was a single mom that was an accountant and she had her own business and she could never afford talent like me. No matter how good her business did, she couldn't compete with a Google, with the big banks, et cetera, trying to offer me and lure me away. So I thought, what if I took my skills and built a product, finding this thing that nobody else kind of thought like it was still valuable to find things after somebody gets in? And what if I could deliver that enterprise quality with a human doing the actual hunting and the algorithms, both the automation and a human expert for the price that the small businesses and mid -market enterprises of the world could afford? You know, not the Fortune 500, but all the people that fall below the Fortune 500. And it turns out not only does that market, it was the perfect time because hackers started going after small and mid -sized businesses. It was the right product at the right place at the right time. So there is a little bit of luck in there that people like sometimes give me a lot of credit for predicting, but to be honest, you know, I had preparation, but the opportunity also found me.

Pablo Srugo (14:19)

So you decide to kind of give this enterprise tooling to let's say the SMB market. Do you go at this alone? Do you have co -founders? what's the setup? 

Kyle Hanslovan (14:27)

Yeah, right. So I started thinking, how was I going to do this? And so I convinced two of my friends at NSA. I said, let's do this idea. And one of them, that was probably the most technically proficient, I'm good. literally me and my co -founders won the world series of hacking. Like we've got skills, but this guy's even better than me. And he's like, listen, Kyle, it can't be this easy, but I had this idea. had to be a product. And so we started testing. We started testing on real data. We actually got to go to a cybersecurity exercise where people were doing like offensive hackers versus defensive hackers. And we could prove we could find stuff that other people were missing. And with that validation, we ended up actually pitching as a small group of founders to this, they call it a startup accelerator. That's people, right? That help you grow your business and learn how to grow an actual software company instead of services that I was doing for the government. And they gave us a $50,000 check. And that was enough to convince my co -founder Chris that not only like let's go, he's my fellow board member. He's the CTO at Huntress and he's built a lot of the craziest technology that he used to focus on offense. And I think now we protect about 150 ,000 businesses with that tech. it's pretty crazy. Something that was just an idea, circling the right friends and enough kind of conviction to weather it all. And nine years later, here we are.

Pablo Srugo (15:53)

It is wild. Honestly, for me, that's the part about startups that is the most fulfilling, like is seeing your idea become reality. And in your case, in a big way, right? 150 ,000 companies relying on your product to stay safe effectively. So you have $50 ,000, you have a co -founder. I'm sure you guys are really good at product, but there's this whole other side, right? you actually have to go to market and SMB going to market, not easy, right? So how do you start approaching that and how does that pan out? And by the way, cyber SMB even harder because they probably don't even know what you're talking about. 

Kyle Hanslovan (16:28)

So you have just said all the things that I wish I would have known on day one. I, again, I might've been like a cyber big brain. I was not great at the business side. And so no joke, I just adopted like curiosity. I was going to ask, I was going to talk to people. I was going to listen though. More importantly, I wanted to hear what people had to say because I knew if I asked them, do you have this problem? They probably wouldn't know what I was talking about. So I would go and sometimes lean in through like education, doing presentations, calling local businesses. And I've told the story before, but I will tell it here just for this audience to, you know, it's nice to hear the vulnerable sides of it. My first five phone calls were to like local businesses of credibility, but they were still in the grand scheme of things, small, right? They're not, you know, doing billions of revenue. They're doing millions. And they no joke. My calls were always sounded something like this of like, Hey, I'm Kyle. I actually am a military member that just left. I'm notable for being very good at cybersecurity and I've got an idea that I'm hoping to protect businesses like yours. I'm not trying to sell you anything. I'm just looking to learn more about the problems you have. I think I can help find hackers that slip by your prevention. Does this even scare you? Are you bothered by hackers? Do hackers even cause downtime? And they're like, “I like your idea, sir, but like we don't even have an IT department”. It was so bad. I didn't even know, right? I didn't even realize these companies had nobody. There was nobody technical, right? I was talking to the paralegal at a law firm or, you know, somebody who was the most junior accountant in a firm of CPA. It was so bad. It was so embarrassing. And by the way, I didn't catch that even though like, I think it was five or six times in a row, I don't mean like, over two weeks, mean, five or six phone calls back to back to back. They were like, we outsource IT. And then all of a sudden I was like, why am I not calling these people, they outsource IT. And it turns out the investors and folks who are not a fan of this SMB go to market strategy, they were like, there's a reason everybody's in the enterprise. Good luck. know, usually the two biggest companies in the world are people who go B to C, right? Business to consumer who sell things like iPhones and apps like Spotify.

And then there's folks that sell to big enterprise and they're like, look, there's a reason people aren't successful this way.

Pablo Srugo (18:42)

 Yeah. And a lot of the SMB is kind of like bottoms up, but things that people are already looking for, right?

Kyle Hanslovan (18:51) 

I know the pain point, right? I got to file taxes.I got to buy quicksense. Obvious.

Pablo Srugo (18:56)

 Exactly.

Kyle Hanslovan (18:57)

Yeah. So, if you can't tell with my tone of voice, I didn't get this right. But when I started talking to the IT outsourcers, “Pablo: all called MSP’s right?”  Yeah, they call all kinds of different names. Some were MSPs, managed service providers. Some would add an extra S, meaning they did like the security side, managed security provider. And then the other ones that most people don't know of, but they're important to talk about because it shows how many different flavors support the small and mid -sized businesses of the world. A lot of people know VARs, value -added resellers, but some of these folks were printer copier dealers that they would sell you that big copy machine and then provide like outsourced IT. Other people were like small telcos and things that you wouldn't even think, but they are providing IT. And so I realized like, Whoa, these are my people. And when I talked to them, they were like, every time we have a security incident, we know that it's painful, but it actually costs us real money. costs us time because they're charging a flat fee. And some of these people, when they had a security incident, they would actually go negative on that client for the month. And then they have to have enough other clients to like amortize or average it out.

Pablo Srugo (20:03)

What would be a standard security incident that they might be doing?

Kyle Hanslovan (20:07)

So this might be somebody like, hey, you fell for the cute. What's going on, Pablo? I love listening into the podcast. I've got a couple ideas. I want you to check this out. I threw it together in this PDF, but if you can't reach it, here's the URL. Both of them doing shady stuff. You fall for the darn thing. You click it because you're interested. My favorite, by the way, is usually it's HR opening up resumes because I have to open those things. They open the attachment, the hacker gets in, and then you forget they're running as you. So they can do everything you can do, right? That means they can see every file, every share. That means they can go and see every keystroke. They can dump all the passwords like I made that example earlier, and then they just start spreading. And once they know your network, they use those credentials and they encrypt or they take down all the most critical systems. So like if you're a manufacturer, they don't actually go after the manufacturing facility. That's too complex. They go after the scheduling software. And then you can't schedule and deliver whatever you're manufacturing. And so you'll pay just about anything to get back up and running, right?

Pablo Srugo (21:08) 

That’s the way it is? It's like a ransom kind of that's the playbook?

Kyle Hanslovan (21:10)

Yeah, nowadays that is definitely the best way to make money is to extort. And sometimes, by the way, they don't even have to steal the data from you. They can extort your reputation. Like if they find out you're regulated. Yo Pablo, I found out that you have report to the government or whatever. And part of that means you have to safely protect information. So I'm going to let you know you're going to pay me $150 ,000 and you've got three days to do it. You're going to pay me in Bitcoin. You're going to have to figure out how to even do that. I'm not going to help you. And if you don't do that, that's fine. but I'm going to send all the data that I just stole of yours straight to your regulator and your fine is actually going to be way bigger than the $150 ,000 fee you're going to pay me. 

Pablo Srugo (21:49)

Crazy.

Kyle Hanslovan (21:49)

 It's ruthless. It is absolutely ruthless of how well they get to know your business. And so if you could imagine any of those scenarios that you could get ahead of a cyber criminal before they could learn the network, before they could fully extort you, before they could encrypt or take away or deny you access to payroll or scheduling, that's a win. That's finding stage zero cancer. It sucks that it happened. It sucks you got sick. But more importantly, you found it before it was terminal. And that's when I realized I was solving not just a cybersecurity problem that geeks love, I was solving a business problem that had real financial, you know, benefit. And it turned out these partners, I didn't realize it, but by not coming in there and promising them like magic, but coming in there and saying, look, I'm really good at this, but I'm looking to make you the hero. You're the IT expert. I'm the security expert, but those are your customers. I'm going to help you whether you have 20 or you have 200 customers. I'm going to make you look like a rock star. And on top of it, I'm going to help you make better margins by both protecting the amount of service delivery, right? So your number of hours are under what you're charging. But more importantly, when you offer additional things cybersecurity, you can make margin on it. And so I was winning with these service providers. They could not only help me get over that big objection. that they were like, how are you going to go out? know, investors saying, how are you going to reach the long tail of the market? You know, all of these, mean, people estimate like in the U S based on census data, 30 plus or 30, 30 million plus SMBs in the US alone worldwide. estimate, you know, somewhere between 300 and 400 million. And I was like, wow, this is bigger than the fortune 500 companies. If I could really crack this and find a partner that I can make them win, but stay in the background, make them again into the hero. That could be a real partnership where they don't just treat me like a vendor, but they treat me as a real partner that we're in this to win -win. And then the end customer is also winning. They're safe, they're protected, they're resilient. So the CPAs that I was mistakenly calling directly, they could file taxes on April 15th here in the U S right. That's the most important tax day. They want to be able to do that. Right. When it comes to lawyers, the most important thing they want to do is when they're promising Pablo, I'm going to keep your proprietary sensitive, you know, confidentiality, you know, information. They want to keep it private. so hackers will actually go after law firms and say, you have this under client confidentiality, but I got it now. What are you going to pay me? So I don't go to the opposing council and share the stuff that's most damning. And that's wild. That's the stuff that people don't even think about cyber crime. So if you can't tell by this time, I've now gone from 2015 building tech had an idea that took me all the way into 2018 to figure that out. Three years of hustle bootstrap. taking every dime, side jobs.

Pablo Srugo (24:29)

So in the meantime, you were calling, direct SMBs those three years? I wasn't even really making money. was like, I was building the software with my co -founders. We were kind of going to trade shows. We were measuring revenue and monthly recurring revenue. You know, we're talking about every single month we had a board and it said, hey, if we don't hit this number, we're going to have to lay off interns. We're going to have to not take salary. And it was a long time.

Pablo Srugo (24:52)

What are we talking about? If you don't mind sharing those, 2015, it takes a while to build even the MVP of this because it's a pretty sophisticated product. Then once you go to market, what's that ramp like? You're one, you're two, you're three. 

Kyle Hanslovan (25:03)

So we're talking about, we didn't even have a first real-. So if we founded at the end of 2015, First reall customers started showing up at the very end of 2016. And by real, mean they were paying, but they weren't large. but they were influential. They had people on the staff that could help me build better product and help me overcome. 

Pablo Srugo (25:22) 

Sold direct by the way? That was like direct SMB

Kyle Hanslovan (25:24)

Still, I was working with the MSPs, but again, the MSPs people forget when you go to a managed service provider, you might only land one of their 200 customers. I see. You don't guarantee to get all of them. And so you can imagine they would help me as a partnership and we'd take down one or two at a time. So it felt direct. The revenue looked direct because it was so small. I, we weren't killing 200 businesses at a time, but they were giving me feedback. I was working for free in their office, learning their life. And what's crazy is if you just, again, zip your lips and listen, not to the answers of like, what products do you need, but listen to the problems that they have. Then you can start imagining things instead of falling for the faster horse scenario, cause that's what you'd get if you asked them what products you need, but listen to their problems and imagine what would life be if they didn't have it and then build what is needed to deliver that. Man, things started growing gangbusters so by 2016 we started going from thousands of dollars per month which was not enough to even cover our insurance let alone like a place to work and live. We started getting it into tens of thousands per month and by 2018 we had enough capital to be able to convince an angel group to write us our first $750,000 check so it took-

Pablo Srugo (26:39)

And you're doing what, a million in revenue, annual revenue at that?

Kyle Hanslovan (26:41)

Not even that. No, I think by this time we were probably a couple hundred thousand in revenue. Enough that we could stay default alive, but we couldn't even invest in sales staff. We couldn't invest in better marketing. We couldn't reach clients better. And more importantly, we needed to hire more folks for R&D. We also learned a really rough problem, which is finding the sickness. Right? Finding the virus, finding the hacker was only one step of the problem. What we learned was they don't have great IT people standing around to be able to do the cybersecurity stuff. They have really motivated junior IT people. So we ended up realizing the real answer to Huntress wasn't just building a product. It was how do I build that enterprise quality tech? And then the problem we learned in 2016 and 2017 was it needed to be fully managed. A human had to be delivering the value. So if you just tell somebody an alert. you're creating them work. But if you deliver them the whole playbook, the whole recipe, and you take care of it for them or for what we had at the time was a little button, you click the button and it took care of all of it for you.

Pablo Srugo (27:45)

And that's automated or that's a human on huntress payroll.

Kyle Hanslovan (27:47)

It started out as a very, very manual and then it moved into more and more automation. So that's that bootstrapping. we literally like we're still improving this even in 2024. 

Pablo Srugo (27:57)

I mean, if you actually think about it like an SMB is paying what in general, like a few hundred bucks a month.

Kyle Hanslovan (28:02)

if that, yeah, yeah. Most of our MSPs even today, like we're talking, when we land an MSP today, the average sales price, you know, annually is $10 ,000 a year. So at this time it's hundreds of dollars.

Pablo Srugo (28:15)

So hundreds of dollars a month to have NSA level, like decade, best hackers in the world, literally to cybersecurity for them. That's just insane. Yeah, that's crazy. 

Kyle Hanslovan (28:26)

And so we had to adopt those NSA principles. How could we be this small elite team? going after needles in a haystack. And it turned out the answer was tons of automation. And so, you know what's crazy now? Like, Pablo , you nailed it. So at that time, three founders doing manual searching and reporting on these computers, super inefficient. Today, our automation is so good and we still need humans. Humans are key because without them, all the automation, like, I mean, I drive a Tesla. That thing tries to kill me at least once a day, even with the best AI. It's not perfect. Neither is cybersecurity AI. It is okay. But it is nowhere close to the quality of a top quartile 25 % or top decile human. They're just not, not a comparison. So, and today we're so good with that automation that even though the automation's got better with humans in the loop, one human can actually protect 300,000 computers at Huntress right now. Officially. That's not like, we can protect it with seeing through like, well, you know, one eye closed or whatever. That is we are wrecking hackers at scale.

one human 300 ,000 

Pablo Srugo (29:32)

And is a simple way to think about it that automation takes care of like X percent in the edge cases service up to that human or is it not really working? 

Kyle Hanslovan (29:39)

That's a great intro, right? Yeah, that's it. Automation trying to take care of the masses. So only the humans are going through the hardest problems, the things that only humans are good at. But the more important part is when humans find something the automation missed, we have a separate team. And this is why we had to raise a little bit of capital, a separate team that does what's called detection engineering. And they say, why did our automation miss that? Let's make this a perpetual loop. So every single day, that's what most people forget about hacking. No day is the same. It's just like how, again, sicknesses and colds, you know, they mutate and they become different. Viruses in humans and hackers change hourly. And so our team, no joke, every single day, every minute, every hour of the day is saying this new thing came by and slipped through the automation. Let's build new automation. It's a living machine powered by human expertise, delivered at the price that these mid -sized businesses and small businesses can afford. So that was the magic. was figuring out the delivery model, figuring out like the margins, because you could imagine we were losing a lot of money with three NSA experts hunting 20 person companies. Like that was not a good business model. And as a result, you could imagine most people were not interested in giving us capital at first.

Pablo Srugo (30:55)

 You got $50 ,000 from Accelerator. You are going for like two years making, you know, a thousand, 10 ,000 a month. How do you even keep the lights on? Like, what are you doing to make things work during that time?

Kyle Hanslovan (31:08)

I mean, we largely had to burn all of our savings. got so bad that at our, our make or break moment was November of 2016. So we had been going for a year at this point. We still had no customers. This is about the time we get our first customers. and we put all of our money, just like you'd go to Vegas and put it all on red, we see that there's this trade show focused on managed service providers. It's in Florida and supposedly 2 ,000 of these service providers. So we're doing the back of the napkin math and we're like, say the average service provider only has 20 times 2 ,000. Okay, that's enough. That's enough to take an investment. And so we took our last $25 ,000 and we sponsored the trade show. Tiny, the smallest booth in the place. We felt like a startup. And so there was four of us at the booth that worked it, gosh, I think nine, 10 hours straight, pitching, doing hacking demos, showing, laying it all on the line. And when I say like we're laying it all on the line, we didn't have the money to ship the trade show stuff. We drove it down and slept in the car. Like that's the type of like silly story. That's how close it got because all the credit cards, all the savings, we were done. We had been going to that long and it turned out all that listening we did made it. So when we talk to somebody we were resonating talking to the pain points they actually had and I will tell you that some people went out on a limb They were you're missing four of the five things I actually need but the most importantly is I can tell you guys are gonna quickly correct this and that little bit of traction those early adopters those people that wanted to be part of our journey to and that's why I use the word partner and they're not customers these are people that were in it and if I was winning, they would then win and they saw this could be a real partnership and it turned out that virality. I just did an event yesterday in San Francisco with my series D partner Kleiner Perkins, one of the biggest venture capital companies in the world. And they said on the podcast that we did together, it was that crazy partner conviction of people. And one comment that they saw was on Reddit. Someone said, if I have another kid, I'm naming it Huntress. And they said, when you have that level of conviction and we have partners and employees that actually have like tattoo of our logo. Now I say it out loud, that kind of sounds like a cult, but I promise it's just conviction. That's what they say, right? Right before you drink the kool-aid. But that conviction was came from listening to them and thank goodness that trade show ended up well. And that gave us our first customers that kept the lights on and it allowed us to slow bootstrap all the way into 2017 into, you know, kind of late 2017, early 2018. 

Pablo Srugo (33:40) 

Do you remember what that gave you? $25 ,000 investment and it gave you well -read, but also it gave you partners, right? Like they didn't actually sign for an MRR amount. They signed like, okay-

Kyle Hanslovan (33:50) 

They signed for like 1Z, 2Z, and then they would organically grow with us though. As I solved objections, they were like, hey, I just landed my second customer. I landed my third. And then we eventually started getting smart and we were like, how could we get so good to the point that we don't land with one, how do we land with 30 % of their clientele? Because we needed that money. The problem that most finance people forget is I had to pay $25,000 upfront for a trade show plus all the other things. Like we're talking about, we were so strapped. We bought TVs from Walmart and this is shameful. me a little grace audience, but we returned the TVs after the trade show, right? We had no other option. There was no other money. That was it. so. 

Pablo Srugo (34:37)

What about you personally? what were you doing with your own personal runway? how did you manage it? I mean, I was having to do side hustle. Like, I was doing training where I could ,incident response. was doing keynotes where like I could get a paid gig, but like most people don't know the Huntress story because again, we're representing companies that aren't Google, right? Companies that aren't meta Facebook. We're representing the backbone of the economy, which is important, but folks didn't know us and what a lot of people don't know of how like close it came.I had three kids at this time. My kids were five, nine, and 11 when I founded Huntress. And so you could imagine the whole family is tightening the belt. We at one time when we had interns, things were so tight, we had to have an intern drive four hours in a U -Haul to get dividers for the office when we had this very tiny small office for the interns on campus. And we no joke went to Joanne Fabric and hand like stapled new fabric onto these dirty, stained, disgusting dividers. And my kids, got pictures of my, you know, a 10 and 11 year old operating a stapling gun, putting this stuff together. that's the grit that most people, you know, they'll tell you the sexy parts of them winning revenue, but this wasn't great, right? I mean, we were all in it. We knew what we were doing was good. And it looks good now that we have a hundred million in revenue. Yeah. times that we're stressing and breaking relationships. You know, kids weren't seeing me. 

Pablo Srugo (35:59)

 Was it you that you told me you had a co -founder that slept in a car or something like that or like used the, used the gym showers?

Kyle Hanslovan (36:04)

You can't go on record about this stuff. Yeah. Yeah, that was me actually. So at Mach 37, remember that 50K? Yeah. That 50K that they gave us, most of the other founders, if not all the other founders, put themselves up in a hotel or, you know, temporary lodging. We were like, we got to stretch this 50K as far as it goes. Cause who knows when there's going to be another dime. Everything else has to come out of our pockets. Right. And so, yeah, 16 weeks I slept in the back of my car in this secure facility. And thankfully they had a gym so I could shower because it would have been real gross. And then I came home on the weekends to see the family. 

Pablo Srugo (36:36)

You know, my biggest question is besides, I always ask because I think the details make the stories and just the stuff you have to go through is a huge part of the story. And everybody wants to hear the grind. But one of the big questions I have, especially for you guys, having, it's one thing when you're like, 20 years old and you're doing this stuff and it's kind of cool part of the culture. In your case, you had kids and not just that, you came from a place where I'm sure you're making like really solid income.

Kyle Hanslovan (37:05)

yeah, I had options to go at any big bank, any big tech company to hire our tech talent. 

Pablo Srugo (37:11) 

I'm sure that would have been a problem. So I guess my question is like, and your story’s one where obviously everything works out and now it's just like, you know, it's huge, probably beyond what you could have imagined, but like it took a long time during that time. Did you ever think, I have to imagine you did think this, what kept you from just being like, what am I doing? Like, let's go make half a million dollars or a million dollars or whatever it is,

Kyle Hanslovan (37:33)

 like at any of these moments. I know some founders are like, I never lost conviction. I mean, we had bad moments. had a founder, for instance, that just wasn't in it. He was a guy that actually worked with me at that defense contracting company we started, you know, doing the butts and seats contracting I mentioned back to NSA. He didn't make it 13 months in. He had to go back to that work and we decided as a group, it wasn't the right decision. that was rough. Like losing your ride or die, somebody you'd work with and even started another company with. Like that's still one of the moments that I hate the most about the company, but it was the right decision. So you can imagine if it wasn't for two things. The first one was like, I read a lot. I'm a huge, huge, consumer of podcast and knowledge. I really believe being curious and learning quick is one of the biggest differentiators you can have just as any person. And so as I was reading books and things along this lines, it was talking about the importance of a good mission. And it took me a while to figure out exactly what we were doing, but I knew what I was doing was keeping people's lights on. You know, when big enterprise gets hacked, they call in an expensive incident response team, insurance comes in, takes care of it. Small businesses, if you can't run payroll for two pay periods. people quit their jobs and go. They don't have that type of money in the bank, especially the average business. So that type of conviction of knowing like I was doing something good that mattered, it was the same type of like conviction that made me feel so good about like protecting U .S. national security and protecting Americans, you know, both local and abroad and just democracy. Like I believe that I've been in the military since 17. I truly believe we are here on earth to give back more than we take. And that mission kept me almost every time. That I thought I was ready to throw in the towel. But multiple times we actually said as founders, like, is this it? Do we do it? We even at one time had, you know, our friends at a bigger company. We considered acquisition to the point that we were actually flying to their office and decided, you know, all right, we were going to sell, but thank goodness it didn't turn out that way.

Pablo Srugo (39:35)

But it's crazy. This is what makes startups so hard and so interesting, right? It's like, first of all, you know, even the startups that get massive like you guys did sometimes go through very very close to death and the second thing is You know some people could look at this and be like, okay cool I should just never quit but sometimes the things really not gonna work and you should quit and you should take that acquisition off So it's just so case by case just hard to figure out and that's just that's just part of -

Kyle Hanslovan (39:59)

and you're right knowing when to say no and I'll tell you for anybody listening this is my favorite part about this podcast right is learning from people's lessons, I know everybody says fail fast, fail often, but no, learn, stand on the shoulders of other giants, learn from their failures, make your own unique ones. Knowing when to throw in the towel is so important and one of the best indicators is the flywheel. If you're doing one -off things, one -off detection, if it was one single human per one company, that would never scale. But when you're building that flywheel, that's perpetual, I can take this many and predictably, each month get a little bit more customers in the top of funnel. This month have a little bit better conversation. This month land a little bit more customers, right? When not just the number of logos, but remember the percentage of adoption. I was starting with like 2 % adoption or 5 % adoption. And then I got up to 30, 50. Now sometimes I have deals that we're just a hundred percent right off the bat. And it's still not perfect, but that's a good example of that flywheel is an indicator that you're onto something that's perpetual. What happens, unfortunately, is most founders, and I say most founders because most startups just unfortunately don't work and they definitely don't scale to the lucky size we've managed to be able to make it, but they don't look at those indicators and they mistake one -off things as recurring things. And I've seen this maybe two or three times where founders should have pivoted years before and just suffered, their families suffered the…. employees that weren't founders who had less equity, but were in it for the mission. They believed they didn't know the risks. They didn't know things were repeatable. And so I put a lot of blame and a lot of respect too on founders of like, you have to lead the team from the front. And that means knowing when to, what's that song? Know when to hold them, know when to fold them.

Pablo Srugo (41:47)

And I think from, my side looking in, like, think you had, besides the fact that had a product, you know, product that solved the problem and was differentiated to tailwinds, you had one of them, which we talked a lot about was this expansion, right? you consistently had expansion in your MSPs and that's like a huge tailwind that makes it easier and easier over time because it creates this kind of flywheel motion. You also, and I don't know to the extent that you were aware of it at the time or not, but you had a huge market tailwind, is like the MSP space as a whole has just exploded. like those two things were helping you kind of putting, I guess, this wind behind your sails where it just, you know, even though it was really hard at first, it only gets easier and easier and easier. And all of a sudden you start to really feel this, sort of.

Kyle Hanslovan (42:31)

Yeah. You, have headwinds just about everything. And so anything that you can find a tailwind that is there. And I will tell you, I took some of that for granted, especially it did not feel like I had a tailwind during COVID when all the SMBs got crushed. You know, think about all the smallest businesses closed up shop, right? The economy stood still for multiple quarters, even the you know, the big companies struggled. I didn't feel like I had a tailwind, but it turned out, and for any, you know, entrepreneur, anybody who's hearing these stories, even though it's still fairly unproven that you can make massive businesses on the small and mid -sized businesses, think about like Shopify, that's a good example, but it turns out those businesses are the most resilient. They're kind of like in the best way cockroaches, right? Really hard to kill them. And even though they might have to go into hiding or they might even have to like shrink in size, they'll get big again. And they will come back and that's one of the things that like, what can you not love about an underdog story? Like watching these businesses go through everything. And on that end, we offered tons. I think as a company who hardly had money, like we, when I say hardly, like we had runway that was measured in months. It wasn't even in quarters at sometimes, but we were given like hundreds of thousands of dollars of payment relief because it was the right thing to do. And if you have that type of empathy and that type of caring and get to know like, treat your partner, even though I don't know every customer, I don't know my 150,000 customers, but I do know my 5,000 plus partners and the direct side of business who won't work through partners. know them well. And what's nice is when you have empathy and you take care of each other, like people remember that. And I couldn't have got to a hundred million without them. And in a lot of ways, some of them couldn't have got their growth without me. And that's like, I don't know. That's the type of, you know, just tailwinds entrepreneurs have to look for. I was too, I don't know, oblivious. I'm going to use that word because I think it's the right word that I was even getting these benefits, but I'll be darned that expansion, you know, now that I've had to learn finances really well as a tech guy, net dollar retention or net revenue retention. If you don't have that land adopted, expand and naturally growing, which ours grows 140 % at 12 months. It's a huge. 

Pablo Srugo (44:47) 

Yeah. Massive tail-end. I mean, just the simplest way to think about that is almost like if you do nothing and I know it's awful, like if you do nothing, you grow 40% that year with 140 % net dollar retention. like, you just gotta add 60 % to get to 100. Like that makes things, that's the tailwind. Like that's clearly, you know, sailing your winds that just keeps you moving forward without much effort. No, just grows over time.

Kyle Hanslovan (45:09)

Yep. Yeah. And again, can't miss those. Even better if you can actually spot those and use them to your advantage.

Pablo Srugo (46:15)

 So let's go back to, you raised that $750 ,000 in 2017, still early days, you've got a few hundred thousand dollars in revenue. What starts happening then? Do you start feeling like things start to get easier at this point?

Kyle Hanslovan (45:26)

So we start feeling that we have it solved. We're like, we have a flywheel. It's a really big TAM. Customers are adopting more. Not just our partners, but the partners customers are adopting more. Our products are getting better. People are really happy. Retention now, we've had customers long enough and partners long enough that we're finding out people are renewing. Always over 90 % renewal. So we're like, that's good. You know, top decile, you know, metrics. And so we're like, it's time we think we can do a series A. Turns out, even though we had conviction and felt we had data, nobody else agreed. I was told no by everybody. 60 plus no's and sometimes you're an idiot no. And we were so odd. were a Maryland based company. So one, we weren't from Silicon Valley. That was actually a real thing. I wasn't the best at pitching this. We were headquartered in Maryland, but we were fully remote, which was also weird. So think about this 2018, fully remote. I actually had some people that were like, if I give you a term sheet, it's going to have the requirement. You're going to go headquarter together. And I was like, no, no, you don't understand. You want to be able to hire anybody. If you want the best talent, don't make them work around you. Don't make them move to you, support them where they are, you know, and we're not going to go around the world, but we're going to go to very specific geographies. That was a strike being from Maryland. And like, even though I had the tech savvy, I didn't really know how to speak the Silicon Valley savvy. That was a strike. And then going after the SMB again, three strikes, I'm out. It didn't matter. And I wasn't the best at pitching this by the way. And so what's really cool is I seized the opportunity. I am super competitive. And so I just took each one of these L's and was like, all right, I'll turn this into a W right. Enough of these L's like kind of dumb it up. So I, you know, I, I really was, I was like, I'm not going to fail at this. And we had some bad rounds. Like what I mean by bad rounds are times that people verbally committed, but fell out. Even had some investors in the first round that didn't follow in in the second round. That's not a good look. People do not like that. They like to see you want to stick on board. But they got it wrong. We…

Pablo Srugo (47:33)

But that was fuel to you? Like it kind of fueled you to get to have them?

Kyle Hanslovan (47:38)

It was a roller coaster. Some of this would take the wind completely out of my sails and make me feel like crap. I'll tell you, I've multiple times struggled on the emotional mental health side. Not to the point that it killed me, but the point that I doubted myself. I didn't realize that it was kind of you know, trial by fire was hardening me for what was going to come for the future. So even after I've been through that and you throw COVID, that's why some of the team asked me, they're like, you're at a hundred million of revenue. and I say “I stopped counting revenue.” I talk about how many companies I can protect. And I'm looking out there and going, I've got 150 ,000 of 30 million in the U S. I'm just getting started. I, know, and they ask like, how can you be so sure? And I'm like, I've gone through it. I've been through those. I can figure out these next problems. But going back to that investment story, I needed series A, I needed capital to keep doubling down on R&D. I wanted to grow, I needed to grow a better sales force. We were just so small, nobody knew who we were. And they didn't believe. And so I had to take a bridge round with some of my most trusted angels, the people that really believed the diehards. And for that reward, their investment, if you take a look at what the return is now from 2018 to 2024 to about 140x return. Wow. So that's, that's sometimes what conviction gets you, especially if you can find the right team. And what's wild is I went from at that point from 1.5 million in ARR. So annual and 12 months, I went to 5 .3 million in revenue. Boom. And then you could imagine I suddenly had term sheets instead of valuing me at $3 million. I had term sheets that were valuing me at 30, 40, $50 million. And that began. what started to become easy. Like last night I was at another, I told you, I consume a lot of like content. So the team, you know, I'll try to avoid the plug, but one of my favorite podcasts for learning from good entrepreneurs is acquired.

Pablo Srugo (49:37)

Yeah, of course. And that podcast is dope. They're absolute kings. 

Kyle Hanslovan (49:40)

So they had a physical event last night in San Francisco. you were there. sick. So I was there and they had literally the founder of Spotify. They had obviously Mark Zuckerberg was the main keynote. They had the founder who did a recorded video of Nvidia, right? Jamie Dimon from J .B. Morgan, like real players. And you know what's crazy is how many of those folks said, including Mark, some version of, if you could do it all over again, or if you knew what you knew then would you do it? No, if I knew what I knew how to go through, I would have been wise enough to know it was my foolishness, my, you know. Being oblivious that got me through that. Cause if I knew what I was gonna have to go through and my family was gonna have to go through, no sane person would have gone through.

Pablo Srugo (50:24)

Even Zuck? Even Zuck said that, that’s surprising. 

Kyle Hanslovan (50:27)

Yeah, no, he was definitely, I mean, he multiple times said like, I'm having fun now, but it was great. How many times he alluded to like, I mean, especially like most people forget like, Yahoo tried to offer them a billion dollars and his, you know, executive team and board tried to fire him. Like most people forget that story, but that happened. There wasn't, I mean, it was actually really reassuring to me almost like from a confirmation, maybe even confirmation bias, but to hear like multiple founders say, it was fun, I missed the early days, but I don't know if I would do that again. I just hope that gives both folks like the reassurance that sometimes the grit pays off and sometimes you gotta know when to fold them.

Pablo Srugo (51:10)

Yes, no, 100%. So you get to. You go from one and half to five million, which is a stellar year. then kind of, yeah, how do things keep going from there? Like when, when would you say, I guess we'll ask that question now. Like when would you say you felt like you have like true product market fit?

Kyle Hanslovan (51:26)

I could see the signs of it. I didn't have it, but I could see the signs of it. Even at that 1 .5 million mark, the patterns were similar and everything I had built were these flywheels, the demand gen I could do. could do it repeatedly. The sales cycle. I could go and our sales cycle is fast when we meet folks. from the time we close folks, it's a 35 day sales cycle. My funnel is turning over every 30 to 45 days. And I was like, okay, this is a flywheel. I could do the sales cycle. Can we do service delivery? Yep. The product can scale the service delivery, like the threat hunting, the expert humans could scale. By that time we had built an engine that was beginning of our detection engine that could keep up with hackers. And we could like eventually get to a point where we were making money, not just burning money. So that was good. And so I could see all that. by again, 2019. if we take a look at this, this is before 2020 with somewhere between three and five million in revenue, but I'm at this point three and a half to four years in, you know, so this was not obvious. It wasn't overnight and no joke every year since then has been revisiting all these flywheels. How do we do it at bigger scale? How do we do it with better quality? How do we do it with more efficiency? How do we sometimes charge less because we can actually give more value to our end customer.

That's a crazy thing that most folks underestimate, but if you have to pinch every penny to hit your revenue, that's not scalable. But if you can actually go the opposite and help people grow more and help people like actually be better businesses and deliver more value, you can do that at scale. so for me, the numbers went 1.5 to 5.3, 5 to 10, 10 to 20, 20 to 40, 40 to 70 and change 73, I think. And this year we've just sailed past a hundred. It's nuts. 

Pablo Srugo (53:12)

Let me ask you this. I have two more questions. This one, and then another, the last one we always end on. We had one person earlier, Blake Hall, founder of IDME, who was in the military before. And you know, what they say, like startups are really hard, they're really emotionally taxing. He was the one person who, you know, because of what he'd been through was like, you know, obviously startups are hard and he went through a lot, but he was like, I was also in Iraq before I was, I was like responsible for people's lives and deaths. So like, in a sense, the stakes were much higher, like there than in startups. I wonder for you, I know you were not in the field, but like you said, the stakes were super high because you're saving lives. 

Kyle Hanslovan (53:47)

Yeah. I mean, I had a combat deployment attached to third special forces group in Afghanistan. So I can resonate with what he was saying though. There are some things that even though this was taxing, like when you put life, and that's something that we actually, don't run our company like a military organization, even though I've got a Navy founder, a co -founder. And the other guy who has been very much attached to national security, that's John. Sometimes we have to bring it back to folks of like, you think this is hard, but let me go and give you a real example of like, this is like what blood, sweat and pain feels like. And by the way, you're doing that in the military sometimes for $30 ,000, you know, and maybe they'll give you a housing allowance if you're married. Right. So I feel it. And I love the point. Did you have a follow -up question though, that you were thinking through there or is just alluding to like, yeah, sometimes it's hard. But is it crazy hard? Nah, the military helped set me up. 

Pablo Srugo (54:41) 

Yeah. Well, that was no, my question was really just like, you, did you feel like even with everything you went through at Huntress that it was harder and more emotionally taxing than what the stuff you were doing kind of an NSA or, less so because the stakes are more like business stakes instead of like, you know, life and death stakes. 

Kyle Hanslovan (54:47)

I'm going to say different. and that's not a cop out. be very specific. there are the physicality and that grind that military prepared me for. I'm not a fan of people that like worship the grind and worship like poor work -life balance. I did it. Almost six and a half, seven years of a hundred hour week straight. Military set me up for that. I was used to working, going on deployment, stuff along those lines. I always was a hard worker. That made it just table stakes. Because though I had younger kids at that time, right? My kids were, two of them were born in England when I was stationed there. And it was easier to go on deployment when they were smaller. When you have to like lose all that time with your family and you know you're not showing up well as a partner, you're not showing up well as a dad. And then one thing I forgot, like in the military, I used to hit the gym all the time. I'd had hobbies, I had friends, and I realized I stopped showing up for myself. That's why I say different because that part of the startup life was actually infinitely harder because I just, I was so lopsided. I was so prioritized on one thing, being the best CEO, being the best founder I could be. I lost all that other stuff and you know what? I didn't have that in the military. So while I can say that the physicality and everything, had moments that don't compare in the military, right? What I mean by that is the military was much harder, but I didn't have the same family distress. And so for me, I would say they were both hard. They were both real hard.

Pablo Srugo (56:27)

That's a fair answer. 

Kyle Hanslovan (56:28) 

Well, would I recommend it? That's one of those like, one out of five stars would not recommend. I love where I'm at now, but I'm probably in that same group. If I knew what I knew then, I… I wouldn't do it again. 

Pablo Srugo (56:39)

Well, last question. If you could go back in time and give yourself one piece of advice, kind of in that earlier at Huntress, what might that be? 

Kyle Hanslovan (56:47) 

That's so good. That's such a good question. I'm glad you end with this. One piece of advice, and assuming I can't say it's going to work out, it would just be believe in yourself and augment the story with hard data. What I mean by this is nobody ever believed, by the way, my SMB vision. That never changed. Nobody believed the security story, delivering humans at the price of a product. That didn't change. What changed was I had all the KPIs. I had the top of funnel, the bottom of funnel, conversion, retention. I had the net dollar retention, the expansion that came with it. In addition to that, I had cash. And when you have financial dollar signs and you can show you can separate a dollar from somebody's pocket, people will listen when you get enough of those dollars. And so the part that I would give as much as conviction matters, the data and if you can put a dollar on the table and say this came from somebody paying for something that cost me maybe, you know, 20 cents, 80 % margin, something along those lines, man, people will listen. And as a result, a lot of the biggest funding that now happens in the managed service provider world is a result of people who actually told Huntress pound sand. And now they realize they missed that 140 X opportunity to return capital. So, you know, I won't say it's not for everybody. It's a lot better to go where the, you know, the road is already paved. But if you got the data, go pave it. There is huge benefits of being first.

Pablo Srugo (58:15)

 Awesome. Love it, Kyle. This has been absolutely amazing. Thank you for jumping on the show. 

Kyle Hanslovan (58:20)

Dude, Pablo, thanks for having me, bro.

Pablo Srugo (58:22)

 I just gave you content that you liked so much. You actually listened to the end and guess what? You didn't pay a single dollar. Not only that, I didn't even put any ads in your face. So you just got a bunch of content for free. And now that I've delivered that value, I'm asking for something in return. Open your app, open Apple podcasts, open Spotify, open whatever app you use to listen to this and hit that follow button. It's actually going to help you because it's going to help you make sure you don't miss out on the next episode, which you liked so much that you listened to the whole thing.