What No One Knows the Podcast / Vodcast featuring The Tampa Bay Wave and Jon Schipp

Hello, you're listening to the podcast called What No One Knows. I'm your host, Lisa Marie Garcia. Please join us as I talk with some of the most important influencers, from entrepreneurs to C-suites to founders to venture capitalists. You will want to know their answer to the question, what no one knows. Thank you for joining. Okay, this is Lisa Marie Garcia, and welcome to a new episode of What No One Knows. I am very happy to be here on kind of a chilly day in Tampa. I don't get to say that too often, but on a chilly day, I'm excited to be here with our guest, Jon Schipp.

Hello, Eliza.

Hello. Thank you for being here in studio. We're at the Tampa Bay Wave offices. I think you— well, we— the reception wasn't last night, but you were around this crowd just within 24 hours, right? I mean, it was last night. I mean, it wasn't here. Sorry, that's what I meant to say. Thank you. So, so you're around everything Wave and let's— I'm excited for us to dig into the conversation.

Absolutely.

So thank you. All right. Well, why don't we talk about, since it was only hours ago that you were around the latest cohort for the Tampa Bay Wave and what I'm most excited about is how you are part of this particular cohort's advisory council and share with what that means and what that looks like and what's to come there.

Yeah, absolutely. So I've been an advisor just in general in the industry for a couple years now. I've advised a number of junior founders, some early stage, pre-revenue. And then when my family and I moved to Tampa around 3 years ago, I started to get involved in the community here. And so I joined the Tampa Bay Wave as a mentor and been doing that for about a little over a year now. And then just recently last night, I got inducted, if you will, or promoted into the advisory council now for the Cyber Tech Accelerator, which is an 8-week program. And I'm really happy to get to meet all the founders last night. We'll be continuing to help them on go-to-market, product development, strategy, and things like that going forward.

So you then, so you're really gonna be able to deepen the relationship with these founders, right? And I'm sure you found some rockstar ones there. They always blow my mind. Yeah. You know, when you talk to, even for a second sometimes I'll talk to them and they tell me their big idea and I'm just like, how did you even think about that? You know, there's—

Yeah, there's some interesting stuff. And also I think that What we saw last night, 4 weeks are going to go by. We're going to hear them pitch again. Yes. And you're going to see the polish and how they actually have made significant improvements, which is a testament to the actual program they're in. And they'll have 4 more weeks after that, and they'll probably sound like a whole different company. And I think that's just amazing to watch.

It's so fun to go from what you went to, like you said, last night to pitch. Yep. And so very cool. And then I understand as, as part of the advisory council, you're really pouring in the hours on your— from your busy, amazing work, professional life, right, into them and pouring in what your depth of experience is in the real life. Like you talked about pre-revenue, right? Past which— which when I was in startup mode, there was no such word or phrase, right, as pre-revenue. What do you think is something that you will probably circle around with them in terms of knowledge that you're sharing?

Yeah, I think, you know, I've only, the first interactions we had was with that pitch night, or not pitch night, excuse me, the welcome reception where they do their 1-minute pitches, right? Sorry, to be clear, this is separate from a pitch night they do later. But you get the glimpse of kind of how they're talking about their product, or their offering, and I think a lot of the times, this is one of the first instincts I have is like, okay, if I can't understand, 'cause I've been in the cybersecurity industry for a while, if I cannot understand in the first 30 to 45 seconds like what you actually do, this is something I wanna go work on with you.. And so some pitches were a little more polished than others because we had some more seasoned founders in there that this is their second or third that they've done. And there's some more relatively new founders. And I think those are the great ones to kind of key in on and help develop that. And so I think the messaging portion of go-to-market is the first thing I'm gonna help several with. And I already got a few LinkedIn messages and phone numbers. Great. That's gonna be one of the things that we're gonna talk about as we get into the next week.

Well, and there's so many different skills involved with being a business owner, being an entrepreneur. And I know you're, you know, two-time founder, entrepreneur. As well. There's so many different types of skills and talents you need. How can anyone have all of them, right? And so one of them, like you said, I mean, if you don't know, if you haven't heard in those first 45 seconds, I almost even say in that first 15 seconds to really get your arms around it, you've lost it, you know, you've lost that. So that's so great that you can share that talent and skill because it is one.

Yeah, 100%.

Very cool. So actually, let's talk about you being, um, your your role and your time in your professional career as an entrepreneur. There was two different companies that you were a part of and then how that kind of led to your reason that you're here in Tampa Bay, please share.

Yeah, so I like to use a Taylor Swift reference. I like to break up my career into eras. There you go. So the first era was my cybersecurity practitioner era. And so I spent, you know, I went to school, went to college, I got a degree in information security and I had a number of starter jobs. Technical support is a very common job you do in IT as your first job. Then I worked my way into Unix system administration, administered Linux and BSD servers. Then I got into cybersecurity shortly after that and ended up being a practitioner for a number of years and eventually being head of security at a couple of small companies. And that gave me a lot of the skill set I needed to talk to leadership and bring the technical skills to the business outcomes we were looking for. Okay. And so I did that for, you know, say, I'll say 6 years at this point. And then I decided at some point that, hey, I wanted to start my own company. So now we're in the second era. And so I started a consulting company It's called Draconix. It was a specialized information security training firm, and I actually developed software using my technical background to make training easier, and I would deploy that in a customer environment. So some of my customers were universities. I even actually got to be on site at some of the FAANG companies and teach them cybersecurity, which was really cool. Wow. But I did that for a little bit, and I had a few partners. They left. I ended up buying them out and ran it for a little bit longer, and then I realized, hey, this consulting thing, I like it, but I want to do something a little bit different. Right? It wasn't my true calling. And so we kind of closed that down. I could have continued to live off the money, but it wasn't— it was, it was a good living, but it wasn't amazing, right? And so I could have continued to do that. But then I decided, hey, I want to try myself at developing my own cybersecurity product. Now, I was already toying around with that with my training service. I told you, told you about— I built that software. But let's build a real product that actually can go be deployed mass across mid-market and enterprise customers. And so I joined a startup as one of the founding members of a company called Command. It was a Boston-based startup, and we developed one of the early security orchestration automation response solutions. And the idea was, like, you know, security teams are overrun with alerts, vulnerabilities, and exposures. How do you help them triage, prioritize, and respond to those in an automated or semi-audited way to save them time? And so that's what we developed. We developed it on-premise, and From there, you know, I had, you know, I was flying out to San Francisco all the time to meet with customers. I had some really cool engagements with some customers that I really admire to today. Meeting up with VCs, went out to dinner with a number of them, and then we actually got a term sheet. We thought we were gonna get our closer Series A, okay, at this time. And lo and behold, life never goes the way you want, but we actually had a new thing come in. So they gave us a term sheet. We could have signed actually, waited a little bit. We were trying to negotiate as the company, as the founding team. But then fast forward a week, we had started deciding what we wanted to finally do. Rapid7 enters the chat.

Okay.

And they said, hey, we actually want to acquire you. So we flew out to Boston, we pitched ourselves, and they were really interested. And we wrapped up a deal in less than 3 weeks, which is actually a pretty fast acquisition.

It's very fast.

So that was another trajectory that was kind of like, I wasn't planning on that. I was planning on, hey, we're going to continue to grow this company on our own, right, for the next several, you know, year, 2 years for Series A until we get to Series B and move on. But it ended up being a really good partnership with Rapid7. And so that's where I end my second era and I go into my third era, which is now I'm an executive at a publicly traded company, Rapid7. Rapid7. And I've done a lot of different things there. I moved beyond the software engineering management and cybersecurity practitioner phase that I was doing over there. And now I moved into product leadership. And so I'm one of the top product strategists at Rapid7. I report to the chief product officer. I get on the phone with Corey Thomas, our CEO, almost every day. He was calling me last night at 8 PM. I was like, damn it.

After the wave You just left that.

So, but I've really loved working at Rapid7. They've been so good to us and our, my career as well as my fellow founding team. We had a lot of different roles in the company, help it grow. There's a lot of new innovation going on and really I think it's just something where now I'm in a very special role in that a product leader that focuses on M&A and partnership-related technologies that we want to bring to market. So when a customer or a segment of customers within the Rapid7 portfolio, which is over 11,000 customers today— this is publicly traded, I mean, there's public information out there, publicly traded company— we figure out, hey, what are the things or the needs that are going to be coming up that we cannot meet today that we don't necessarily want to build in-house because it's not our core competency? As a company that's trying to grow, we got to stay focused in our core markets, right? Which is vulnerability and exposure management, which we've done for 20+ years, and now managed detection and response, which is one of our fastest growing businesses now and that we've been involved about 10 years. And so these other innovation areas that kind of broaden or augment our portfolio to give more impact to customers, give them better economic leverage, as well as better use cases and user workflow experiences, they kind of fall under me. And so I meet with founders every week, sometimes every day, learn about their tech and team, what they're bringing to market, get— keep pulse on the trend, figure out, hey, what do we want to do? I see something, someone I'm really inspired about, or I see a big market opportunity, build that business case. Let me take it to our executive team and see this something that we're going to go pursue. And so like last year or not last year, 2024, I lose track of time. I love the acquisition of a company called Noetic. It was a cyber asset tax service management company. We acquired them and I think it was July, we signed the deal, I think it was July 8th. And then that became one of our fastest growing products going into 2025. And now we're in 2026. We already have over 700+ customers in that. Nice. And so now I'm working on my next initiative to kind of bring a new product to market, which I'm really excited about.

Well, it's exciting work. You know, obviously, if I was, if I had your job because of the change that's everywhere and evident and that you have to yield to it. And so I guess where I'm going with this is one of the things that you said that I wanted to unpack was you were talking about in your career how you've been adaptive to change and that you, you know, yes, your first business was okay, it was fine. You were good at it. You were making money. It was profitable, but you knew it wasn't what you 100% wanted. So you were be easily able to change. And I think that in tech, it's all about change. I mean, we're dead if we don't change and if we don't have that mindset. And that's not in every industry, and it's also not always the mindset of every founder and entrepreneur. So I do love that about you. And then as we talk about that, you know, I bet it's very interesting for you. Like you said, you meet with different founders in the role that you're in now. And so with that, I always like to hear what someone like you might think is like that X factor of different founders you meet where you, you know, someone is more adaptable or someone's easier to work with or someone, you know, that you can really see where they're going versus maybe not. What have you noticed in your experience of different clients you've worked with, different founders that you worked with that, you know, a quality or characteristic you appreciate?

Clarity of conviction probably comes to the top of the list. Obviously, everybody needs to be successful. You have to be able to be working with someone has some basic personal soft skills, right? They're agreeable, they can work with you, you can have an honest conversation. But when it comes to the top of the list, yeah, definitely conviction, being able to articulate their vision. They actually thought about it, not just 6 months, not just a year, but they thought about it longer term. And then I also really value authenticity. I don't think that actually happens enough. I meet with a lot of founders that dance around questions, and it's not necessarily because they're unsure, Sometimes you can kind of get a sense as they just don't want to go there because it might make them look bad, but we're not here to make you look bad. We're here to understand. We're here to really get our best assessment of you, and the more that you can be candid and authentic and transparent about what you do and the problems you're solving and some of the challenges you even have, the more that we can actually learn and see, here's the ways around corners we can work with you on those things, right?

Right. I mean, how can you solve their problem if you don't really know the real problem? You don't know their problem. On the other side, if they're, you know, none of us like to do the things we don't want to do. None of us want to talk about the bad things, the hard things. A lot of times it's because we're in kind of denial about it, right? But we can't fix it either if we can't embrace it. And trust me, I'm speaking to myself on that. So no, I— but it is important that, you know, and I think this is a good, you know, message for the startup cohorts that we work with and the young entrepreneurs and early people in the early stage of their business that you do have to, you know, deal with those things because they only become worse if you don't, and they have a life of their own, so just bite the bullet and deal with it.

And my feedback to you, if you're a founder listening to this call, is like, if you don't know, just say you don't know. Right. Right, and there's nothing wrong with that, 'cause we're here to help you find out answers, right? And it's okay to say, hey, I haven't figured that out yet, I haven't thought about that yet. That's completely okay, right? And we'll work through it together. And that's kinda how I've lived my life too at the companies I work. I don't know everything. Right? I've been in the industry for 15 years, which to some people that's a short amount of time, to some that's longer, especially if you're earlier in your career. But there's a lot of times where, hey, this is a whole new market. I've never— I don't know anything about it. But guess what? It's up to me to go figure it out. And that's where you leverage your network, your ecosystem, the advisors, you know, your peers, your friends, your colleagues. There's so much around us in this community, like just in Tampa Bay itself, that you can rely upon, like in the Tampa Bay Wave as an example, to help you through some of these new areas.

Or you ask AI like I do.

Yes, that'll give you some good guidance to start with.

Yeah, no, it's good. I wanted to unpack another thing you said when you were talking about your professional career. You know, it is so important. It sounds easy, but it is so important. You were talking about staying in your lane, you know, knowing what— first of all, knowing what you're good at, staying in that lane, but then also knowing what is profitable for you, right, in that lane. And then knowing what drives you, what you're passionate about, you know, and those elements. And I think what makes people unhappy or unprofitable or they're like, how did I get here with a business that I hardly even like to do and I don't recognize is because they think it's so easy to get out of your lane and to take on more and to think that more is better. And it's really not. I mean, just kind of address that a little bit in your professional opinion.

Yeah, I think, you know, whatever makes a good product leader, whatever makes a good CEO and founder or just any executive is having an understanding of your business, the core business drivers that you need— growth, retention, things like that, right? And then also understanding what your role is and where you can make the biggest impact to affect those business drivers. And so I think having clarity there is where you're going to spend— it influences how you spend the most of your time and get the most bang for your buck, essentially.. And I'm a person, I'm an ideas guy, right? And, but I'm also an execution person. This is where I do really well. And I've done a lot of number of different roles. So it, it's easy for me just personally to be like, oh, shiny thing over here. Right. Mm-hmm. I'm so interested in that. I wanna go explore it. But it also takes a bit of self-reflection and you have to be in tune with you as a human, yourself as a human being and your personality. This happens to a lot of people. It happens to founders everywhere. But as long as you have the ability to reel yourself in. Yeah. Be like, hey, this is awesome. I'm not ready for this right now. I'm gonna come back, you know, in 6 months and maybe, maybe that's an opportunity for us. Maybe it's not the right time. But the thing I will say, don't stay in your lane so much. It could be, it could be a double-edged sword. Don't stay in your lane so much so you're not innovating. Right. There's a point where your lane, you have to know when your lane should veer or your lane should change.

That's a good quote.

Yeah. And so I think at that point, long as you have this enough self-awareness, you're able to navigate those challenges and the pivots that you need to make as a startup or as founder.

Team. I love that. That's great. So just to switch gears, get completely out of our lane to a whole new freeway going somewhere else, tell us about your experience from where did you come from to Tampa. How do you like Tampa Bay? How do you like the culture, the business ecosystem, the weather? And how long have you been here now?

Yeah, so I've been in Tampa for over 3 years. My wife and our dog, we moved down here when Rapid7 opened our office downtown on Water Street. So that was, that was kind of the impetus for kind of getting down here. But as I said, I've been at Rapid7 for 8 years. I was working remotely for a while. I came from central Illinois. We lived in a town called Bloomington. It was where State Farm headquarters was. My wife worked at State Farm in the law department. And so we were there for a number of years until Rapid7 opened the office. So we were mostly— she lived everywhere all over the world. She was a military brat. Hawaii, North Carolina, California, etc. So water bug, right? Okay. So now you're kind of getting sick. So when Rapid7 opened the office in Tampa, She was like, "Oh, we gotta move back to Florida." And on Water Street, no less. Yes, exactly, yes. So it was no-brainer for her. I had to do no convincing. And I always, my family's been vacationing in Florida since I was a child. And so we always loved coming down. We usually go to the East Coast, New Smyrna Beach. Yes. Which we love. We actually, I'm there all the time. I do a little bit of surfing. So I go over the catchways on the Atlantic. Anyways, and so we moved down here to Tampa. We love the weather, we love the culture, very warm. It reminds me of the Midwest quite a bit. And you can be outside all the time. And it's just that you have the, the ocean on the other side of the state. You have the Gulf on this side. You have all the natural springs. We're scuba divers. I picked up sailing since I moved down here, so I got a Hobie Cat 16 sailboat. And so we're on the bay. We got a powered boat. So we're just enjoying all the Tampa things.

This is the lifestyle for you. Why did you wait so long?

Oh my gosh.

You have all the water toys. You know all the language. You love the water. That's Tampa Bay.

It's Tampa Bay. Love Tampa Bay.

Yeah. Well, congratulations. You landed in a great place. And other than just today with the coat, yeah, it's always usually the same medium.

We have families flying in for the Gasparilla Pilot Fest. We talked about it a little bit earlier. So they're getting a cold visit, something that, you know, they were looking for a little bit warmer weather, but things happen. We're still going to have a good time.

But it's still warmer than the weather they're coming from.

It's still warmer than—

exactly right. So that's all that matters. Oh my gosh, our time is running fast here. I would like to ask you one thing before we get to our key question, but Can you just dig in one more time in terms of your professional experience as an entrepreneur, as, you know, professional that you've been? Can you share a lesson that you think that you've learned primarily through experience versus, you know, the MBA and the Business 101 business and all of that, that we know that, you know, you really, really sunk in because of experience that you went through?

Yeah, I mean, I think You know, there's, there's a lot to kind of unpack there, but I think one of the most important things that only experience can really provide is working with other people. Like there's no substitute for working with other people. And, you know, and that the fact that I meet so many founders, work with so many executive teams and, and operational teams and, and engineers and product managers of different caliber, right? Uh, juniors to very senior principal level, uh, product leaders and engineers, personality becomes one of the things that either helps you drive towards success or drive down to failure. 100%. And some of these people have the skill sets. They know their domain very well, right? But it's that part where they struggle. And so I think it's just, you know, kind of sharing. This is the thing that I think matters the most, even to executive teams. Like, I've worked with, you know, just founding companies. I've seen executives who I'm just like, I cannot believe the way that you're conducting yourself, right? And this is what's actually impacting your teams.

Yeah.

The culture at your organization. Yeah. And why they're not rallying behind you. And it all comes back from ourselves. And so things like executive coaching, therapy, psychologists, all these things are actually incredibly important. Yes. I used to think this was all very fluffy. I know there's gonna be listeners who think it's still fluffy. It only was about 5 years ago that I really learned how important these things are. Being comfortable with yourself as a human being, understanding your strengths and where you need help. Yes. And just being in, carrying a large basket with you that you can take things with you back home, right? And so I think that's actually incredibly important. And 2 of the best books I've ever read, I've read 100+ leadership books. I don't think a lot of 'em are that great. There's some good ones, but the 2 best I've ever read are one called The Motive. It's a fictional story, which is— it's a great way to approach some challenges this executive is having as a CEO of a company. And the other one is called Reboot: Leadership and the Art of Growing Up, which is the subtitle. And they really hit home on the challenges of neglecting your responsibilities as a leader when things are hard because you don't feel comfortable. And they really focus in on honing yourself as a human being that can drive change and drive inspiration onto others. I think those are some of the most important things you could do as a as a leader.

I just want to stand up and say amen, hallelujah, and agree with everything you say. That the human element is the most important, and it starts with you. It starts with you, 1,000%. And thank you for the book suggestions. I'm, I'm a, I'm a— what is it— book junkie. I'm just a reader, and I have a new goal now. I mean, I'd love to read as much as I can. I'm always reading anyway because I'm in the business, but those are our client books and client manuscripts. But I have a new thing. I heard someone say it, so I stole it from them. So I'm making sure I finish one book a month, which I should probably do more. But yeah, so I just— my January book is almost done, and so I'm gonna put this— these on the list. So thank you for sharing that, and, uh, very good. Uh, and agree with you too. I had the mindset that, uh, you know, mentor, coach, and all of that— oh, come on, what do they know that I don't know? No, that was when I was much younger, but I agree there's huge value in that. All right, we're at our last question already. I knew this would go fast, and I appreciate you so much with what you've given us so far to listen to. So the question is, Jon, what is someone— what is something you can share that no one knows about you?

Okay, so this is kind of— I'm gonna tell you a little bit of a story. So unconventional path, but I used to play in a touring metal band. So, oh my gosh, yeah. And so I did this like late college until a couple years after, whenever I was in my first cyber security practitioner role. I think things like that does not have to be hard rock music. It could be a lot of other passionate things that involve some element of do-it-yourself, the punk rock attitude, if you will, where it's like, hey, we had to go— we didn't— we weren't a big band. We played gigs all over the Midwest— Louisville, St. Louis, Indianapolis, towns in Michigan, whatever. We were traveling all the time on weekends. We even went on tour, bought a van, but these were all things that we funded ourselves, right? We didn't have a label, we're just a bunch of kids at the time essentially, right? We're early 20s, right? Late teens, early 20s. And we had to go figure out how to make our own merchandise, how to make our own CD covers, start with a printer and make your own graphic design and print that out, right? Slot those into an empty blank CD cases, right? All these things. And eventually over time you figure, okay, Okay, now how do I present this whenever I'm playing on stage? What's my booth gonna look like? How do I attract people out of the audience to come to my booth to purchase these things? And we started to figure out lighting, little desk lamps we wanna use to highlight pieces, a rack, we went to a clothing store, we actually ended up asking if we could have one of their clothing racks that was not used. So we kinda folded our shirts, put them on display. We developed, we bought some electronics and you know, those garage, so automobile workers use garage lamps, these very, like they're usually orange, very bright.

Yeah, yeah, yeah.

You know, working late at night, right? Work lamps, work lamps. Work lamps, yeah. And so we bought those and just ingenuity at the time, like how can we have a better stage performance? We cut the wires and we rigged in a switch that we could stomp on when we're on stage. And so we could do synchronized flashing with the rhythm of the music. Oh, that's great.

Manual light show.

Manual light show, exactly. So these are all the kind of things that like really that helped me in my startup because you're figuring it out. You don't have outside of your ecosystem, the accountability and responsibility for your success falls upon you as the leader of a company. And so you have to be creative. You have to be, you know, bring some ingenuity. And so I think a lot of that taught me hard work, determination, and just the creative aspect. And then I carried that forward. It was the first time that, you know, as a kid, I really decided to go deep into something before I got really into cybersecurity, right? And it was music.

And so that was just one one of the lessons I have.

It doesn't matter if it's— it could be art, it could be anything else that you have in life, but the getting up, getting out there, pursuing something, and learning from failures and trying to have your own goals and trying to reach them— I think that journey, not the destination, but the journey itself is so important.

1,000%. The mindset.

The mindset. The growth mindset.

Yeah. Thank you so much, Jon Schipp. It's been such a great conversation. I can't wait for everyone to to hear it and watch it. And I thank you so much for being part of What No One Knows, the podcast.

Thank you, Liza. I appreciate it. Thanks for having me.

Thank you for listening to our show, What No One Knows. If you'd like more information regarding our guests, it's in the description below, as well as if you'd like to work with our publishing and promotion team, that you can also find in the links. Thank you.