Start Small and Prove the Model
Casey spent five years building Sprocket Security with his own money before taking outside investment. He focused on acquiring customers and proving he could run a profitable business rather than chasing early-stage funding. This approach let him make mistakes with his own capital and demonstrate real traction to investors.
Scale Through Automation, Not Just People
Rather than simply hiring more penetration testers (an already scarce talent pool), Casey built software to amplify existing expertise. His attack surface management platform allows one expert to monitor multiple companies continuously, solving the capacity problem that limited his solo consulting practice.
Hire for What You Can't Do Well
Casey's advice: understand your weaknesses enough to know what to look for when hiring help, then delegate. His first external hires were bookkeeping and marketing, followed by a sales rep—roles that freed him to focus on product development where he added the most value.
Local Network Beats Cold Outreach
Casey's early customers came from relationships he'd built during his consulting years, mostly within Wisconsin. Having a reputation and local connections made customer acquisition significantly easier than starting from scratch with strangers.
Continuous Beats Periodic
The core insight behind Sprocket Security is that annual security testing is insufficient when technology changes daily. By monitoring and testing continuously as systems evolve, companies can identify risks in real-time rather than discovering them months later during scheduled assessments.
Community Investment Pays Dividends
Casey has been organizing the Madison security meetup (MadSec), creating a local talent pipeline and establishing himself as a thought leader. This community building effort has been invaluable for both hiring and business development.
Casey Cammilleri: We do social engineering, which is, you know, everyone's got phishing emails before and they've seen that, right? We work like real world attackers and we'll send out these phishing campaigns to all of our customers. Well over the past five years. That is probably where we improve the most in cybersecurity overall is because all these tool sets can now detect what is fake messaging or some sort of phishing email really well.
They're still not perfect, but
Jacob Miller: they lot better. Welcome back to the Startup Wisconsin Podcast. In today's episode, we're talking with Casey Camilleri, CEO, and founder of Sprocket Security, a company that's been doing continuous penetration testing for about eight years now, and they're based in Madison, Wisconsin.
Casey started as a penetration test. Basically getting paid to legally hack into companies to find vulnerabilities. But he realized that he was just one person with limited capacity, so he built sprocket security to scale that expertise through software and automation. Instead of testing once a year, like a traditional security firm, they monitor continuously.
Testing whenever there are changes or new threats. So companies always know their risks. We talk about skilling from a solo consultant to leading a team and his approach for hiring locally versus remotely, and even his thoughts on building a tech business in Madison, Wisconsin. We even get into his practical advice for founders about when to focus on building versus pitching to investors and what someone interested in cybersecurity should know.
About getting started. So let's jump into my conversation with Casey Camilleri from Sprocket Security.
Casey Cammilleri: Uh, we do continuous penetration testing, um, but the way that we do it is, is different. We're the good guy hackers. We break into companies, we tell them how we did it so they can fix it. For the bad guys, take advantage of it.
Instead of doing that just once a year, we do that all year round. Mm-hmm. And we pair the technologies and the infrastructure that the company has. We monitor those for change. So if there's change in a way that impacts security, we're there to test it. If a new threat comes out, new vulnerability, we're there to test it so that way the companies can.
Always know what the risks are and they can identify them as soon as possible.
Jacob Miller: Awesome. Awesome. That's cool. So now I'm like curious like how this all started. So how long has it been now since you've been in business? Oh, geez. About seven, eight years. Yeah. Yeah. That's awesome. Uh, congrats by the way. I think that's, that's like, you know, not, it's, it's not easy to get that far.
And also like I was just kind of browsing like your, uh, just your website. And your kinda, your LinkedIn profile is like how many people work there and it's like over 40 it sounds like. Yeah. We're about almost at 40, right? Yeah, we're like 38, 39. Yeah. I know. Sometimes in the LinkedIn, uh, it's like, oh, someone will say they work with them and they don't really like, it changes every week.
Yeah, that too. Yeah. Yeah. Um, so yeah, I'm curious like how, how this all got started. Like what was kind of like the early stages or the, the moments, you know, in your life where like, this is a thing that I think I can solve. Like, or, or do better than what's currently up there. Yeah.
Casey Cammilleri: Well, I was. I was a penetration tester for the majority of my career.
Um, security consultant, whatever you want to call it. I was basically breaking into companies and then, you know, it, it, it's a really awesome job. Yeah, yeah. Actually getting paid
Jacob Miller: to hack in. Yeah. Getting
Casey Cammilleri: paid to hack and, you know, do illegal activity is awesome. Um, but I was like, I'm just one person and I'm like, how can I do this for more companies?
How can I help protect more companies? And I knew that. I have a certain capacity and the only way you can do that is just, you know, get more humans to do this type of testing. And the experiences was difficult to, to get that experience takes time. And I was like, I think what I can do is change the way that we do this in the industry.
Number one, why are we even testing it once a year? You should always be testing for your security, uh, to identify these things. But how can I also take myself and scale myself up so I can test multiple companies at the same time? That was really kind of the, the idea behind it is like, how can I just help more people?
Um, but I just don't wanna have a bunch of bodies, you know, we're already, we're already, uh, starving for, you know, penetration testers and, you know, in the industry. And so I was like, let's just maximize the ones that we have and let's also build the automation to, to scale this out, to help as many businesses possible.
So
Jacob Miller: like, so there's a software aspect to it now? There is. So like, what? Yeah. So like, obviously you were. In your past role, like before you started the business you were using like other software. I'm assuming that you did not build to do the hack. I'm just curious like how Yeah, explain like how that kind of works and then how did you, like when you built your software, like what did you want it to be different about it so you could scale yourself, so to speak?
Yeah. I'm just kind of curious how that all kind of played out.
Casey Cammilleri: Yeah. I'll take you back to like, you know, as a tester you develop code, but it's usually in just enough to get your job done. Right. Just enough to do that exploit or break in. Um, but really over the years I started building larger and larger pieces of software, like distributed password cracking systems, uh, and report writing, uh, tools.
And immediately I kind of started to become a developer and understand that. And I thought, well, if I want to do this continuous thing, I'm gonna need to build the tools and the software that tells me where all the technologies are for an organization. My targets. How they change. Uh, and so if you fast forward to today, that's called attack surface management in the industry and that it didn't have a name back then, but that's what I was building.
And I was like, I need this in order to do testing continuously. Because if you think about it, if I'm going to look at, uh, uh, all these companies, I need to find where all this, let's say web servers or WordPress websites are at any given second. And so. That was the a SM tool that I probably spent the first year just developing really.
So Sprocket opened their doors. I was developing that tool set that really enabled me, the tester to scale.
Jacob Miller: Okay. When, when you were starting out, like who. Who did you, um, sell to? Like were you like anybody, whoever I can work with? Or was there like kind of a specific industry or business size? I guess I'm kind of curious like your go-to market strategy back in the day when you started it.
Casey Cammilleri: You know, after working, and, and this is the benefit of working in the industry for some time, is that I built up, um, a reputation as a tester. I built up my network of the companies I was helping serve. So that way when I did. Start Sprocket. Um, the, I was targeting those networks, people I've worked with before and it was always easier for me to capture business, you know, within my network, which happens to be local to Wisconsin.
Jacob Miller: Yeah. Yeah. Uh, I'm curious, like, it sounds like you had the experience, the skills and like the knowledge, the connections, all that stuff. What was like, or were there, I guess, any challenges in the beginning? Like was it like your first hire, like, wow, like working with this person and like, when I'm not doing the work anymore, I kind of was like, oh crap.
Like they aren't doing it the way I would want to do it. Or what? I'm like curious, like what were the early challenges for you? Ev every,
Casey Cammilleri: every founder has that problem. It's like, I have this vision. I I do it this way, you know? And then, um, you bring more people in, right? And, and you want them to build in, in the vision that you have, right?
In the way that you want, right. Really, you have to trust the people, get the right people in and do that. So there is a number of struggles, number one, um, I, I knew it was an extremely hard problem that I was gonna tackle. And it's like, yeah, if I'm gonna build a business, let's, let's tackle a hard problem, right?
Sure. I enjoy that. Make it extra difficult, right? Extra difficult, right? I mean, if you think about it, like just following all the technology and how it changes, you know, within each organization is, is just a tremendous challenge. Uh, so, uh. In the early years, you know, like I understood how that worked as a tester and I had this vision, but, um, that r and d to development and then bringing additional people in to build in that vision, uh, takes a lot of communication essentially, you know, it just to make sure that we're building the right direction.
We're building lean because I'm, you know, I'm obsessed about speed in, in, in building this thing. But yeah, there was a lot of like. There was a lot of times where you just need to over communicate
Jacob Miller: that in the
Casey Cammilleri: early
Jacob Miller: days when you kind of get past like basically five, 10 people, you know, obviously you have less time with each individual on your team.
Right. And then eventually you kinda have to have someone that's like managing with you and like getting, you know, having these communications with everybody or helping manage projects or efforts. So I'm curious like around how you approached, um, the scaling of your business and becoming a leader, uh, versus just being the person that's like.
Doing the work with customers or with clients? I'm curious, like did you leverage, um, any, uh, consultants on leadership and like growing an organization or did you go through any kind of programs? I'm just kind of curious on that, like how you kinda built yourself up to become a leader for a business?
Casey Cammilleri: Yeah, yeah. Um, so yeah, I'm a, I'm a typical first time founder, so, and I came from a practitioner side. Uh, and I'm a, I'm a builder, so it's not like I've done this over and over and over, right? So I didn't have some of that knowledge. So I, I leaned on resources that were available, um, and that, you know, was SOAR locally and they, they kind of help, uh, you know, provide some sort of mentorship because they've been there before.
Um, I'm actually not familiar with it, if you wanna, yeah, it's called, so r uh, it's called, so r and I probably should know what the acronym stands for. I absolutely don't remember. Um, but really it's a collective of, um, uh, basically leaders, founders, CEOs that have been through. Been through this and done it before.
Sure. Uh, a lot of them are, you know, either retired or exit it in some fashion and they just wanna get back to the community. That's amazing. That's cool. Which is awesome because, you know, it's like I have these challenges as I'm growing and they're like, oh yeah, I've been there, done that before. Here here's, here's a couple, uh, things to think about.
Yeah. So that was a resource, um, local community was a resource, but, um, my, my advice was. My advice would probably be to just self-reflect on what you're good at and what you're not good at, right. And then what you're not good at. Make sure you do it enough to understand what, what needs to be done, but then bring in outside help.
So, uh, to answer your question of like, who else did I lean on? You know, I ran the books, you know, financials and everything myself and just typical bookkeeping, you know, and I'm like. Dude, that's not where my time is best spent. Yeah. Yeah. Like
Jacob Miller: I hate this right now. Yeah.
Casey Cammilleri: I did it enough to understand it, you know, to, to figure out when I bring someone else in, like what am I looking for?
And that was, you know, that was probably the first thing I actually reached out. Marketing, uh, being second. 'cause I just need some, some help building things on the marketing side and then. I believe my first hire was actually a revenue generating, oh, actually that was my second hire was revenue generating sales rep.
'cause I, as a founder, you should be able to sell whatever you build and you should be the best salesman at that. But you gotta do all these other things too. Right. And so for me, I wasn't nurturing those deals, wasn't being in communication enough, you know, that. And I, and I realized I'm really not good at that.
Like, you know, or, or, uh, I, I better serve the business, you know, in the product and engineering side. So, um, so that's where it's like, just be self-reflective of like what you're not good at, and then bring help in or hire for, for those roles.
Jacob Miller: Yeah. Yeah. Uh, I'm also kinda looking at like, the makeup of your team and like, kind of where they live.
Like this is something that, you know, we experience even at Headway, uh, as an agency. It's like, okay, the talent, we try to have as much local talent as possible, but at some point. The pool kind of dries up. So I'm kind of curious if, um, like how that has been for you or, you know, thinking about company culture, right?
Like, hey, we wanna be able to get people together, we wanna, you know, have opportunities for people to hang off face-to-face and, and you know, hopefully increase employee retention, all that kind of stuff. So how have you kind of approached that, like finding the talent you need to kind of, because I saw, I think you have seven openings right now.
I saw, yeah. So it's like, say if everyone's looking for an opportunity, check out their Yes. Their, their postings. Uh, but yeah, so I think. I'm just curious like how that's kind of been for you and how you've kind of navigated that over time. Yeah,
Casey Cammilleri: yeah. We always look for local if we can. Yeah. Um, but we also understand that, you know, we want to hire the best as well too.
We want, you know, the team wants to work with the best as well, so we want to hire local if we can, and we prefer that. There's some, some positions that we just don't wave around. It's like Absolutely. Needs to be local, right? Sure. Um, so for our, our head of product for example, is like, we knew that, you know, that hire had to be here, right?
Yeah. Had to work, had to collaborate in person. 'cause we know that's the best way to move that forward. Um, but other times it's like, you know, looking for penetration testers, it's like, well, you know. You're gonna dry up the pool locally so far. And so we know that, like, okay, we'll we'll go remote on those.
Um, but yeah, you just gotta, I mean, local's great, but doesn't need to be local.
Jacob Miller: Yeah. Yeah. Uh, and I, I'm also curious around how you just kinda approach your company's culture. Like what kind of activities do you do? Do you do any like company retreats? So I'm just kind of curious how you guys approach kind of that stuff.
Yes, yes.
Casey Cammilleri: So, uh, you have to kind of manage. Culture from, um, a couple different perspectives, right? You know, it's, it, it's really the people, uh, help develop the culture leaders and their behaviors, uh, morph that, and you have to provide an environment that is, is, is great to work for, right? And so all of that goes into culture.
And the way I think about it is you're gonna have local employees and you're gonna have remote employees, right? So you gotta, you gotta do things that work for the whole company, whether you're remote or local, which remote can be tricky, right? Like we, we've, we've all experienced that like, you know.
Virtual happy hours only go so far. Right. You know, but like, is there other ways that you can engage remote employees, you know, so, um, it's doing all hands, flying, everyone in or flying maybe just the teams in and getting them together in person is important. Um, we just did the Crazy Legs race, uh, here in Madison.
So like we have a lot of runners on the team, so it's like, let's, let's get together and let's run. I'm not a distance guy, but I survived. Nice. But, uh, you know, and we're just doing a, you know, um, just yesterday I, I sent out a message to a company picnic in the summer. So you just have to Yeah. You just always have to keep a pulse on.
Pulse on culture. Definitely over invests in people. Yeah.
Jacob Miller: Yeah, yeah. Today's episode is brought to you by Headway, a digital product agency based in Wisconsin. Do you need to design and build a world class user experience for your software, but feeling like you just can't get there on your own? That's where headway comes in.
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We're so confident that we'll be the right fit, that we offer a 50% money back guarantee. If you don't think we're working out within the first 45 days, ready to see how we can help you and your team, just head over to headway.io and book a free consultation today. You obviously had a vision in the earliest days of the business, and obviously over time that vision either.
Comes to fruition or evolves or matures. So I'm curious like how the vision of the business has changed from day one to like now we're looking forward to the next three to five years. You know, what, I guess how has that, how has that been for you to change the vision as it evolves and the, the team size changes and all that kind of stuff?
Yeah,
Casey Cammilleri: yeah, yeah. It, it, especially in, we, we often say this even in the hiring process, like, you know, it is like you ready to work at an extremely fast pace, you know, company because it changes rapidly. But it security even changes quicker, right? Like, you know, just today there's gonna be, you know, um, hundreds of different vulnerabilities that come out, right?
How do they affect our, our customers? But then the way you go about testing that is different, right? So like, it is just constantly changing and evolving. It's, um, my job to be looking into the future of the vision to make sure that, you know, we're staying ahead. Of things. So yes, there's, I'm gonna say the word ai, right?
Because everyone says that, you know, what can that do for us? How is that changing our industry? How does that impact our roadmap? All those things. As a founder and a builder, you need to, you need to be thinking about, right? Um, so from the beginning it used to be this is simple, you know, do X, Y, and Z. And then over the years things change.
And I think a greatest example of that is, you know, we do social engineering, which is, you know, everyone's got phishing emails before and they've seen that right? Um, we work like real world attackers and we'll send out these phishing campaigns to all of our customers well over the past five years. That is probably where we improve the most in cybersecurity overall is because all these tool sets can now detect what is fake messaging or some sort of phishing email really.
Well, they're still not perfect, but they lot better. So when we send it out to all of 'em, company A will basically say, Hey. This looks to be fake. I report that, but it shares it with the whole platform. So if you think of like these technologies that analyze email, um, a lot of these companies buy the same type of technologies, but the technology's sharing that threat intel information across all.
So we used to send that and everyone would click. We get, you know, either payloads or, you know, some sort of re remote command and control in the environment or their credentials, whatever we're, we're going for. Now it's, we send that one report says malicious, and then boom, it's dead everywhere. So like, that's a great example of like, when I started Sprocket, you know, it was, it was easy.
It was like shooting fish in, in a barrel. But now, now it's not easy. Now it takes a lot of time to set it up. A lot more time and effort to evade those controls to get it in. And then once you do get it in, if it gets burned, it's burned across all of our clients. You need to be thinking, okay, what is the next, um, what is the next era of, of things, you know, like, how do I bypass that?
How does this affect the thing I'm building? And so now that's kind of changed our strategy of, of how we deliver that type of testing. So that's kind of on the product side as on the team side, you know, and, and, and building a company. Uh, you, you become scrappy and then you, you know, and, and you don't, you know, you.
You have multiple people doing multiple roles, but as you grow, right, those roles narrow. Um, you, you put in more frameworks, you know, heck, we have, we have training, you know, manuals now for, for exactly. You know, it's, it's, HR isn't just meeting with Casey and like doing some things anymore. It's a actual more formalized structured process.
So, um, that's just typical company
Jacob Miller: growth. Yeah. Yeah. Um, I am curious around, uh, 'cause last night you mentioned, uh, the meetups, mad Security is what it's called, or Mad sec. I'm not sure. Yeah, we call it Mads Sec, but yeah,
Casey Cammilleri: it's the Madison, uh, information Security Group. Yeah. Yeah. How did that get started? How long have you been doing that for?
I think almost 20 years. I, I took it over. I'm not the original founder. Um, okay. But, but I, I took that over, I think 20 years ago and just kind of, um. Kept that moving. Right. Um, um, Madison has a, a really great information security, uh, uh, community and, and just having events and getting people together and having other people speak and share information is just, is awesome.
So it's like no matter if you're like. Into the weeds and information security, or you're like, Hey, I'm running a business and I'm like, I, I gotta do something in security. Where do I start? Like, that's a group. Yeah, that's a group to check out.
Jacob Miller: Okay. Yeah. How did you get involved originally? So I'm assuming, uh, you went to school for like, it, and then it was like, I guess like where did you kinda run across it?
How did that happen? So.
Casey Cammilleri: If you go all the way back to like, when I was a kid, you know, like, what are you gonna be when you grow up? Sure. Yeah. I was either gonna be a welder or I was gonna work with computers. Yeah. Yeah. And I was like, um, all right, I'm, I'm gonna work with computers. Mm-hmm. It just seems like a, a, the better approach long term.
And uh, you know, if you ask my brother, he would probably tell you, you know, that I'm a really annoying younger sibling because I always took apart the toys to figure out how they work, right? Mm-hmm. So, like, kind of naturally. The curiosity, the creativity, the computers aspect morphed me kind of towards the route of like, okay, I could do it, but like, how can I break these systems ing?
How do they work? Right? Yeah. And that led me closer to the, the offensive penetration testing side. And, and then I did a couple collegiate cyber defense competitions, which is a great program. Interesting. I didn't even know that was a thing. It's, it's, it's basically a giant game of blue team defenders.
Red team pen testers, essentially. Okay. And, and then they give you our business injects. And so as a college student, you're in there and you are competing with others, other schools and teams, essentially to get the most points and defend against the, the, the pen testers essentially, and keep your network secure.
Um, so I started on the blue team and I did that. I was like, this is awesome. I love it. Yeah. Now, fast forward today, now that I'm in the industry, I'm, you know, I, I, I don't do it anymore, but I used to do some of the red, the red team, you know, the pen testing side. Yeah. Yeah. So, um, being involved with things like that really helps solidify, like, yeah, this is what I wanna do.
Jacob Miller: Yeah. If today, like if someone was maybe like in it, in an IT program or going to a start one, uh, and then they're hearing about this like, oh, actually that like security seems like really fun and interesting and challenging. Like where, like how, what would you recommend them to, to do? Like, oh, join those challenges?
Or like, I'm just kind of curious what, yeah. If they're like, Hey, maybe someday I could work at a place like sprocket security or something like that. Yeah.
Casey Cammilleri: The very first thing to, to ask yourself is, am I a life learner? Like, do I like learning new things like every day? Yeah. And you need to have that discipline in order to succeed because it, it changes so quickly and you need to learn those new things.
So if you go to school for it. You're gonna learn some fundamentals, but you know, as soon as you get outta school, that's dated information. Right? Sure. Because it, it's constantly moving. And so it's up to you as part of your job to constantly be learning these new things and engaging. So number one, you better like that.
Yeah. And, and, and then, um, and then, yeah, it's, there's a bunch of like free challenges out there that you could do and start today. So, um, there's, there's something called Hack the Box where you can sign up for that and it's basically like capture the flag challenges. Oh, cool. And other challenges. It's like, how would you break into this computer or this system?
Or how would you abuse this technology? And this is all
Jacob Miller: virtual, like online, all virtual. Yep.
Casey Cammilleri: Yep. And, and that's not the only one. There's a bunch of other ones out there like it, but that is a place to be like, okay, I'm interested.
Jacob Miller: Mm-hmm.
Casey Cammilleri: Um. You might wanna do some reading, you know, and start to get the fundamentals down before you just start go hacking.
Mm-hmm. Otherwise, you may not have the greatest experience. But, um, a a lot of those have walkthroughs and, I mean, there's YouTube
Jacob Miller: nowadays. Sure, sure. Yeah. Is there, uh, um, so a lot of this what I'm hearing, it's like, oh, it sounds like it's all systems and like, you know, company data and stuff. What about, do you work on anything, uh, related to like hardware security?
Like for example, you know. Buildings have hardware that's connected to the security of the door, things like that, or just machines and stuff like that? Like is that also a space that you work in? We don't. Okay.
Casey Cammilleri: Specifically, um, do we have the capabilities of, of doing that type of security testing? Yeah.
'cause we have the, the talented team that, that could do it.
Jacob Miller: Sure.
Casey Cammilleri: So, um, we have done it before, but where we're really focused on is the continuous aspect. Like how can we look at, you know, the infrastructure and web applications. Over and over and over to really minimize that gap. Yeah. And when you, when you look at hardware, it's doesn't have fall into that realm, um, as well.
Sure. So we're kind of focused on that continuous side of things, but there is a need for that. Yeah. Everything's connected.
Jacob Miller: Yeah. Because it's like, um. Just like all the wireless data interchanges you can have with phones and everything too. It's just, you know, it's kind of crazy. Like so many things are, credit cards are wireless now.
It's just, there's so much. Yeah, yeah. Yeah. Um, that's cool. Yeah. So I'm actually curious around, uh, just, you know, being a founder in, in Madison or in Wisconsin, you know, overall it sounded like your experience has been pretty positive, but I'm just kind of curious, like, what, what do you really like the most about, uh, being a founder, uh, and growing a business in Madison?
Casey Cammilleri: Uh, the people you get to work with. Yeah. Like, I mean, um, we're in the Midwest. The Midwest values just come through so strong. Right? Great work ethic. Um, there's a lot of resources here. As a founder, you should be resourceful. Um, so like, even if you, you know, they're not right in front of your face. If you go digging, you'll find them.
If you go talking to people, you'll find them. Mm-hmm. Um, but what I like about building here is, um. It doesn't, you know, especially in tech, it's not the typical coast or valley style. You know, the, there's a lot of good talent here in tech. Um, and pair that with the good working, hardworking values and, and, and great people.
You can build awesome companies here. Yeah.
Jacob Miller: Yeah. Uh, is there something that you feel like throughout the last, like eight years, um. That you wish you know, was better or could be improved? I guess whether it's Madison or Wisconsin as a whole, I'm just kind of curious, like, oh, I wish there was more of this for the community.
Um,
Casey Cammilleri: probably the thing I wish for is, I guess it's a little selfish, it's all good, is the fact that, you know, there, there was there if there could be a larger pool of that technology talent, like that deep technology, I mean. We have health, health tech, you know, locked down pretty good from all the spin outs of, of Epic and everything.
Sure. Uh, so we have good engineers. Right. But, um, a, a lot of it is either kind of that manufacturing side or that health tech. Like let's get just some more other types of industries in here. Mm-hmm. Related to tech. Right. Wouldn't it be cool if there are some AI startups that are happening? Mm-hmm. You know.
Wisconsin and there are, but you know, if there was more of them right, we would um, have probably a larger talent pool Yeah. Of individuals deep in that type of tech space.
Jacob Miller: Yeah. What do you think that could look like? Like a solution to making that a thing? Ah, I'm just curious. You don't have to have an answer.
I don't think I have an answer.
Casey Cammilleri: Yeah. But if I had to take a guess at what would actually fuel that the most is probably more investment. Um. More capital being pumped into these startups that, um, are building. Right? Hmm. Um, so, and you know, we are fortunate enough to have investors here from the Midwest, uh, invest in us and, and make some connections and we just need more of that, I think, to really fuel
Jacob Miller: that growth.
You know, something I've thought about, which, um, obviously there's a handful of like public pitch contests that happen across the state where. The prize is, you know, more, a little more substantial than a thousand dollars or 2000. You know, like I'm, I'm always curious, like, how would you feel like if there was like, hey, every quarter or twice a year, or there's more than what?
More than what there is now? There's like, for example, tell on tech just at the million dollar. Yeah. Like, that's like, oh, we're gonna get some applications, you know, and then like the, you know, after you get this, like, you then now have to work out of Wisconsin for the first year or whatever, to really pull in people.
Like, yeah. What if we had like more pitch contests like that where it was like, Hey, we're gonna pull people in. And when you get into that pitch contest, it's not only, hey, you can win a hundred K or 50 K or whatever it may be, you're also going through the starting block program. Yeah. At the same time. So we're not only like giving them the capital, we're also helping them like carve out like their market, carve out their solution and everything.
'cause they could be pitching from just like, you know, whatever ideas they had. But what if we could like really hone those pitches in. And then they're like, oh. The more they realize like, oh, I love the Madison startup community. Yeah. Like, I love the support I'm getting. Once I get this capital, I kind of wanna stay here.
Yeah. Like, that's kind of an interesting thought. I was like, I mean, do you feel like that could be an interesting approach? I think so. Um, I mean, share my thoughts on Yeah, go ahead. I'm just curious. Again, we're just speaking our lot. Yeah. As a founder,
Casey Cammilleri: I'll, I'll share what my thought process was on, on all this.
And first time founder too. Right. So like, yeah. Um. I would look at a lot of those, you know, like, hey, do this thing, go pitch, you know, win 5,000, even 20,000. Yeah. Something like that. Um, I started spra security with like 40,000 in cash and I bootstrapped it right for five years before I took outside investment.
Um, the way I looked at that was like. You're right, it needs to be a larger dollar amount to get my attention to do it. 'cause for me, I always kept asking myself, I could do that. I would probably learn something, um, from it. But really what I need from my business right now is I need. Sales. And so a part of me is like I could spend the time and effort acquiring a customer that gives me $20,000 of revenue.
Jacob Miller: Mm.
Casey Cammilleri: Way easier and quicker. So I always devoted my time to doing that. Now that was my business. Um, and so I didn't really participate in a lot of those should, maybe I should have, you know, sure, maybe I could learn some things in, in retrospect and move faster in the business. So I'm not saying don't do those things, I'm just saying.
Analyze where your time is best spent, you know, and, and also assess where you have gaps in knowledge as, as a founder too. And then does it make sense to do those things? But if more of 'em had a, a price tag of a million dollars, I would devote more of my time. Yeah. To some of those things. Right. Learn some things, you know, get some capital to, to build.
Sure. But for me it was like, just sell. Just sell the thing you're
Jacob Miller: building. Yeah. I think, you know, it's, 'cause there's obviously two paths. There's like the, you know. I just need to pitch the idea and show there's market opportunity and show the business model and like get an investor excited enough to be like, yeah, I'm willing to bet on you.
Yeah. Otherwise there's the other path where it's like, which again, there are also VCs that are like, we need evidence of revenue already before we even think about, 'cause they're a little more risk averse and they investments. Um, but like, yeah, like how do you convince somebody or like, you know, really change someone's mind on like.
Build, then sell or, you know, it's like, because I think that's a lot, most people think like, well, I need something to sell. Versus like, no. Like if you just have the concept and you can pitch it to them and say, Hey, this'll be ready in three months, would you be willing to be my first customer? But then, but show them like, what, they're really, really outta this thing.
Like how did you, so for you it was like kind of service based. It, it was service based, but it, uh, TE tech enabled with software? Yes. So like, you're obviously doing. Um, like you're taking your skills and your time and your energy to execute. In the early days, the software has become a bigger part of that.
Um, but for someone that doesn't have software and they're trying to sell and they don't have expertise, they're just like, oh, I need to build this platform and then, you know, I'm providing value. So like how do you think about that with somebody, like with a founder? Like how, I guess, how do you, how would, how would you explain that to them?
I would probably just focus on
Casey Cammilleri: the numbers don't need to be big. Right. You can do small experience experiments and learn. Right? And so, and, and number one, everything is gonna take much longer to, to build and do than you think. Right? Acquire, you know, for me, I want to acquire 10 customers in year one. I, I, that didn't happen for me.
Right? Like, I, I just want to build these features and hit this roadmap. Right? Well, that took longer than expected. Right. But, um, the, the way I was thinking about things is like, if I just. Think small, fast iterations, lean even on the business financial side of things, right? Can I get that first customer with the MVP that I put out, right?
Okay, now I can, now I have, um, some revenue. How do I deploy that? And to con, continue to build that way, no matter where you're at, if, if, you know, you can basically say, this is how I'm running the business, this is how I'm thinking about the spend. So you have something to show. Um. Sometimes an idea is just not enough for an investor, you know?
And, and it kind of depends, you know, on what you're building. For me it was software as product, you know, it is, it is easy to just start building, right? Yeah. It didn't, it didn't cost me things. I didn't need a warehouse and a bunch of inventory and, you know, a hundred thousand dollars machinery, you know?
Yeah. So, like different business, you know, so take it with a grain of salt. But, um, I often, I often think like, let me show you that I can build something, sell something to a market, fill a need. Let me show you how I can run a business and run the numbers to make this profitable because, um, you know, what investors are really good at is doing their due diligence and saying, let me, let me expand on this.
Let me, let me do my due diligence and, you know, what does this look like in a model if I blow this business up? You know? Yeah. And so, and then it's easier for them to be like, I'm going to invest in you Yeah. And your business. Um, and that's kind of approach I took, you know, I ran Spra for five years. Um, I.
You know, was, uh, you know, I, I ran it, it was profitable since day one. Uh, those are interesting things. Um, you can do 'em with shorter timeframes, you know, and smaller numbers definitely. And then capture that investment to grow quicker. I just wanna make all the mistakes with my own money first.
Jacob Miller: Yeah, yeah, for sure.
So now that you're a more mature business, but obviously you're in an industry that's always evolving and changing, uh, like how do you kind of like, um, you know, innovate or like. Like, you know, when you already have like commitments to customers in your current product and your current service offering, how are you finding time to like say, maybe add a new feature or to add a new service or, I'm just, how do you kind of make time for that?
Yeah. Uh, it's so
Casey Cammilleri: important what you say no to, right? Like that's, that's kind of like a product 1 0 1 thing, right? You, you spend a lot of time saying no to, to, to make sure that you do, uh, build the things that you want to in the roadmap. Um, but then also the roadmap, uh, doesn't necessarily need to be fixed.
And I think that's a, a, um, a hard, hard thing for cybersecurity. At the, at the rate it changes is that, you know, I believe that this is what the roadmap's gonna look like, 12 to 20, 12 to 24 months out. However, like for example, what is AI doing in this space and how it's changing, right? You can try to get ahead of that, but like, will you be right?
So you need to be flexible a little bit. You need to understand where you're going to say no, where you're gonna focus on product. So that, and then you need to talk to customers, right? Like you need to understand what, what, what do they want? 'cause they're, they're paying you for the thing, thing you're.
Thing you're building. Right? Um, and then that's your job as, as the, as the founder, the builder, the visionary is, is to what are we gonna do next? How are we gonna stay ahead, um, invest in r and d and innovation as well to, to help make those answers a little bit more clear and keep your business
Jacob Miller: Yeah.
Yeah. Um, awesome. Well, I think we can wrap things up. Uh, thanks again. How can people learn more about Spra security if they're, if they're curious for their own business or if someone wants to apply to one of the openings? Yeah, just kind of whatever
Casey Cammilleri: you wanna share.
Jacob Miller: Uh,
Casey Cammilleri: uh, dub dub dub, uh, spra security.com.
We have everything from careers out there to learn more about our platform and what we're building and how we can help companies. Um, I'm on LinkedIn, Casey Ka. Um, I'm pretty accessible there, so if you have, uh, some founder building specific questions, uh, definitely happy to to answer those. Awesome. Well, thanks again
Jacob Miller: man.
It was like, it was a great convo. Loved it. Hey, thanks Jacob. Cool. Thanks for joining us on the Startup Wisconsin Podcast. Wanna support the show. Don't forget to subscribe and get updates. If you're feeling generous, you can share, rate and review our podcast to help others find us. Alright folks, until next time.
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