From Failure to Growth: How a 5-Time Entrepreneur Applied Startup Lessons to Corporate Success

On today's episode of Curve Ahead, Kirk Fackre, VP of Sales at iCorps Technologies and self-proclaimed "recovering entrepreneur," shares how his five startup experiences shaped his approach to growing established businesses. Discover why hyper-personalization beats automation in sales outreach, how AI serves as both opportunity and threat in the security landscape, and why internal mentorship and employee retention create compounding value for both clients and companies. If you're balancing growth ambitions with security concerns or trying to cut through the noise in digital marketing, this episode delivers actionable insights from someone who's seen both sides of the business spectrum.

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On today's episode of Curve Ahead, I'm joined by Kurt, the Vice President of sales of I and self proclaimed recovering entrepreneur. With five startups under his belt, Kurt brings a unique perspective on how lessons from entrepreneurship can drive growth in more established organizations. In our discussion, we covered why hyper personalization beats automation in today's sales outreach and how AI is reshaping both security and selling. We also talked about how mentorship and internal retention helps businesses scale smarter and avoid costly missteps. If you're trying to balance growth with security or wondering how to stand out in a noisy digital world, this episode delivers thoughtful and actionable insights you won't want to miss. Hey Kirk, welcome to the podcast. Do you mind introducing yourself? Thanks for having me, Brian. Yes, yes. I'm the Vice President of Sales at I Cor Technologies, which is a security and IT consultancy. Do you mind telling me a little bit about your background and how that landed you at I core? Sure. Most of my earlier career was in smaller companies, startups, tech startups. I did that for really, as I'm going to say 20 years and then ultimately it became exhausting. So I went back to the corporate world and this is my second sort of back to reality gig. I learned at startups what not to do and I've been trying to apply those lessons to the last couple of companies I've been involved with helping to grow. Tell me about that transition. Right. Like I know a lot of people focus on transitioning out of the corporate world to become an entrepreneur, but what is it like to transition the other way? That's a great question. And obviously there's a curve there because I did transition out of the corporate world first, had 20 wonderful years of exciting times. Getting back is an adjustment. I don't think entrepreneurs choose it necessarily. It's more that circumstances change. So for me, ultimately my initial idea was to ride the rocket ship to the moon. And I tried that five times. And then when the rocket ship never left Earth's orbit, I thought, well, let's get back into it. And I think what was useful to me to make that not just less painful but actually enjoyable was taking the lessons learned. And with this, with a young company, it's about growing it. That's the same thing that any company wants to do. So I think the lessons I learned in attempting to get off the ground were equally relevant to helping a kind of a mid to late stage company find their next ride upwards. Yeah, I spend so much time doing outreach trying to get in front of other people and focusing on sales that like if I were to transition back to another corporate role, like all of the things that I've done work there also it's just having organizations realize that you've busted it to like get to where you were and it just sometimes doesn't work out for one reason or another. More often than not, I think the failure rate even, well, certainly at the time was high. It's probably only gotten. Although the barriers to entry are lower. Like there's so much enabling technology you can use to get off the ground quickly. You don't need all the stuff. But the same problems persist in terms of making your brand known and having. Developing a successful product that people actually want. So those are the things that remain challenges for young companies face those. Challenges every single day. I bet. So tell me a little bit more about I Corp. Sure. So it's a 30 years old company that began serving really kind of on premise IT infrastructure which makes me want to go to sleep by saying that. But really when I joined at a good time I think. So that was about seven years ago. And a lot of I core's longtime clients had at least begun the journey towards the cloud. So it was no longer about hardware as much and more about strategizing how to best move legacy systems into the cloud, which ones to keep, which ones to replace and then later. And it's always been an issue, but it's certainly more of an issue now how to secure your company against the multitude of. Multitude of threats that are coming out all the time. And that's been the more interesting part the last couple of years. Is the, is the threat level changing because of the same tools that are available to help organizations get off the ground more quickly? Say like a cursor AI. These, these AI tools that allow you to create programs really quickly. Is that part of the reason you're seeing security needing to be more robust? That's very true. I see it on two sides on the security side and equally on the sales side. So it's the same kind of drivers in both in terms of the sales side. There's just so much automated messaging going out now that people are simply overwhelmed. And if you want to move that back to what I CORE does for a living, the same is true on the security side. The tools to attempt to penetrate a business and we focus more on small to medium businesses are profoundly more powerful than they were and they become more powerful every day led by AI advances. So on our side we now have to and ourselves and our partners have to implement more and more AI just as a kind of an outer barrier. It doesn't replace the need to have security analysts and things like that. But we've been using AI technology as kind of a first look at all the many things coming at ourselves and our companies as a way to kind of understand what to focus on. So let's talk about the AI piece from two different parts. Right. You mentioned from the technical side, but also the sales side, which I mean, being the VP of sales, are you guys leaning into AI and sales automations to help with those early touch points, or are you saying that in order to be successful and to differentiate yourself, it needs a human touch? I think I've come to the latter point of view. I was early interested in AI for all sorts of reasons and did experiment back when it was really more machine learning. And I think it's been called AI for longer than it actually has been. And I'm not sure we're quite there yet, but. But the initial machine learning stuff was kind of interesting in terms of personalizing at scale, which obviously is a oxymoron. You can't personalize at scale. And at this point now I've totally become very disillusioned with automation. So we use it very in a limited way and not to blast out millions of messages. So I think that's the challenge. How do you then get your message through when you have to contend with all the noise out there? And I think going back to basics has helped. I mean, the telephone is still there. LinkedIn outreach, when done in a genuine way, not at scale, can be very good. And if you put all this together, and I think omnichannel is the marketing term for you put all that together but don't just unleash it. You need to really be focused on who you want to talk to and why they might want to listen to you. So knowing that you're working with an established business and like, what would you do if you put yourself in my shoes in an early startup who you know is still trying to establish themselves as a brand and getting themselves in front of people, would you still continue to lean into some of those automation channels or would you spend a lot more time hyper personalizing and actually spending the time to engage with that as a prospect and, you know, building that trust and rapport over time? The latter for sure. I think it's the same. I don't think it's very different. I think it's just harder if you're not broadly known. So we have the advantage of, you know, a certain brand, but there's lots of companies in our space that have that. To your, to your point, if I was you, and I have been you in the past five times, I do some mentoring on the side with people kind of in your world. And it's the same advice. You know, you need to talk to a lot of people, but you can't start with a pitch. So yeah, you need to figure out all the stuff. Who's your ideal customer? And then the most important next thing is not how to get to them, but figuring out, first of all, are they really ideal? And if so, why should they care? It's less about what you're going to get from that interaction and more about what they're going to get. Which may sound kind of corny, but if you think about it, why would anybody talk to you if you don't have something relevant to their interests? Yeah, I think it goes back to driving value. Right. Because I have the title of founder in my LinkedIn. I get messages constantly. That kind of goes back to the. A lot of automation, not enough personalization. There's been a couple of times where I've been so blown away by like an email that I responded right away because it was so hyper personalized to me that I'm like, they took the time to understand who I was to start asking the right questions from the beginning and now like they have that little bit of an edge. So. Yeah, I mean, I get it. Yeah. I think for founders and you might be unique because you like. A lot of founders that I work with in mentoring were technology founders, which you are at some level, but you also have kind of your sales minded and you have a charisma and an approach. A lot of pure tech founders are first of all terrified of that outreach. It's just simply a blocker for them. And when they do force themselves, they're not very good at it. So it can be a challenge. I don't think that's probably your issue. It might be more that there's simply too many people saying too many things too many people all the time. That's the biggest challenge I think we all face. On a personal note there, I am incredibly introverted. Right. These, I love doing this because it gives me an opportunity to connect with people and that's something that I'm passionate about, is building rapport, building relationships with others and seeing how I can tie everybody together. But I am incredibly introverted. And the first few calls that I Had like this were so incredible painful for me and the person I was talking to. So if you're in that boat, like, don't give up. Just keep putting in the reps. And it really does make a huge difference. I think it's a superpower. I too am an introvert, and it's weird that we both ended up in this profession when we have to do so much outreach, but I think it's actually a superpower. I think introverts are much better at listening and kind of understanding where someone is coming from because they're not focused necessarily on the outcome that they're going to get from something. And more about, let me understand this person or this business and how can. How can I be relevant to them? So I think it's actually an advantage once you get past the difficulty of doing it. I would agree. And I think the other advantage is that a lot of us are very analytical, so we come prepared with questions or ideas or just not preconceived notions to have, like our own personal agenda served where, like, some people who are in sales and are extroverted may do. And that used to be more effective. I don't think it's been effective for a long time. And getting back to business briefly, like, the most important conversation we have with a prospective client is the first one. And there's all kinds of, you know, rules of thumb. You got two ears, one mouth. You should be talking half as much as you're listening. I would argue maybe less. Even you want to ask good questions and wait for the answer and respond to the answer rather than be thinking ahead. What's the next thing I'm going to say? To look smart. Yeah. That drives me back to a book that I read last year. The name of it is escaping me, but basically the guy was a former FBI agent and he always did negotiations and he kind of teaches his techniques, which, I mean, for me, I thought was super impactful to kind of listen to how he does it. Taking time, active listening, making sure that you're understanding and able to continue the conversation, even if it's just putting another question out there that kind of hangs to allow the other person to answer it. I think I've not read this book, but it might be thinking fast and slow. And I think that's a fantastic. If it is the same book, it might be something I better end up reading. I will find it for you. Cool, Cool. So let's get back to I corp a little bit. How are you as an organization? Kind of differentiating yourself in the marketplace. Yeah, well, thanks for that question. It's always, to me, it's preferential to be the high cost, high value provider. Like it can be considered to be a commodity, a thing you do because you must. And the same is certainly also can be said of security. So being differentiated in the world of cybersecurity and IT consulting. And we think of ourselves more of a consultancy than an IT company. So the people that work here, we call them consultants. It's more like a firm than an IT shop. So the difference there is simply expertise and how we kind of differentiate. How we do differentiate is on that side we bring in people sometimes right from tech school, sometimes late career people, but if they come in early, they tend to stay because there's really seven different levels of expertise that you can navigate through from the IT side to security. So there's a path. So I know this is a longer answer than you asked for, but essentially we have fantastic retention of employees. They stick around because they can grow. And when you stick around in the same industry at the same place, this is not maybe great career advice that I'm giving. But we've been able to retain people and take advantage of their journey of growth and their passion for being at a company that supports them so well. So people end up very becoming, very expert. And we have folks that are now virtual CIOs that began as help desk engineers. And that's absolutely a differentiator when you're talking to small business owners who want not just expertise, but continuity. So that's actually quite a big differentiator, not just the expertise, but the fact that we've retained people sometimes for 25 years in one case. So you had mentioned the seven levels. Do you know what those are? I do. So there's intern, IT associate and that moves to what we call level one, which is more of a help desk role. And we have a help desk, seven people, and they're always moving up. So if you move off the help desk, if you have that interest, you can become what's called a tier 2 or mid level consultant is what we call them. And that's more of a generalist, someone that does the work of it. The next stop there would be a senior IT engineer or consultant as we call them. Those are like IT manager slash director type people. Then we would move up to a strategic technology advisor, which is quite close to a virtual cio. In fact, it's fairly interchangeable. So that's one path. And then we have actually more than Seven because there's three different skill sets on the security side. So we, and I'm going on about I Corps here, so I apologize. But we've always done security but now it's a discrete practice area. So we have people there that are more executing on security, doing repeatable backend security projects. We've got people that are more on the strategy side and then we have what we call Virtual CISO's Chief Information Security Officer which actually are very necessary to like a regulated company. So there's a lot of places to move around here if you stick around. Back to the previous conversation about the retention. One of the points that I wanted to make is that especially in a smaller organizations, tribal knowledge is huge. And if people are always coming and going, like every time you lose somebody or you lose a little bit of that. Being able to retain people for years and years and allow them the space and opportunities to grow and learn into being the next level I think is a huge differentiator. Especially in the day and age where there's millennial and Gen Z workforces who change jobs quite frequently. That's true and that's why it might not be career advice that offer broadly, but for here it works and it's a huge advantage to the company. In this case I core technologies and the institutional knowledge is huge because they get to the point when they get along. I say they a lot of guys, some women, when they get to a certain level, when they're more into the strategy side then they become resources internally to other people. It's not just mentoring, although there's some of that. But if you're like a mid level engineer and you come across something you don't know, there's GS in our company, about 12 people they could talk to get instant information about what their situation is. I think that's one of the hard things about being an entreprene is that the road that you're taking isn't necessarily so clearly defined. And if you're looking for that knowledge, it's on you to either find mentorship to help deliver that back to you or derive it from experience. And both. I mean the experiential part takes so much time and money and effort that it's not necessarily the best approach. So if you can find a mentor who knows or has been there before that you can learn from. And mentors are often, I mean, I'm going to say generous, but in a way it's a two way street there's nothing better. There's no better feeling than talking to someone that's just starting out on their journey. I'm talking personally again and being able to share lessons learned as well as accountability. So part of it is, okay, I've got domain knowledge in it now. Before that it was enterprise software and before that mobility and blah, blah. So I have these skill sets in terms of industries, sort of. But more importantly, I've lived that journey and I know what not to do as well sometimes as what to do. But then the other piece is accountability. Right. Because I think the hardest thing in the world for a founder, after you do find your niche and you are convinced this is going to be useful to society or from a commercial standpoint, just having the discipline to stay with it is really hard. So having a mentor that actually doesn't just have good ideas, but can give you homework and make sure you do it between the sessions, I think is actually almost as valuable. Yes. Because I mean there's, there are days and weeks where things just kind of trudge on and you don't see a lot of growth or progress and you wonder, am I doing the right thing? And it's really about trying to stay as hyper focused as you can on solving this single problem that you're doing. Well, it's. Entrepreneurship isn't unlike any other job. It's about executing the small things incredibly well and just being forefront with everything that's going on. Be and to have a mentor, you have to step outside of yourself and give a moment of vulnerability. Because now you're acknowledging, I can't do this all on my own, I need somebody else's help or advice in order for me to progress to where I want to be. I agree. And I think if you're like a bright young thing from mit, which is mostly who I was coaching recently, you may not necessarily see that. Right? You may, because you've been very successful in your academic career. You've beaten out 99.9% of other aspiring college students to get into this elite university and you're going to walk out of that place, chances are, with an option to move over to Google or Facebook or Meta. And so the ones that actually decide to do their own thing, those are the most focused, driven people that are not necessarily coin operated but they have this burning idea. So then you bring in a mentor that hasn't had that success and man, are you sure you want to listen to them? I get some of that, yeah. I mean I love to knowledge share with other People that I meet on what it is that I do and how I leverage my platform for success for others. But I wouldn't necessarily say that right now. I'm at a point where I could be a successful mentor for other entrepreneurs. I could give them advice on what to do and what not to do, but not necessarily be a full fledged mentor, if that makes sense. It does. And you mentioned earlier about the reps putting in the reps. I'm older than you and I've had. Five reps. Well, let's get back on to talking about I core and some of the things that you guys have probably seen recently. We talked about AI a little bit earlier on, but how has the demand for AI impacted the solutions, the tech solutions that businesses are needing right now? Yeah, so this might be a bit of a journey into the weeds, but we're doing it. So there's a technology layer that used to be called a security operations center or soc. They still exist. The more modern approach is something called mdr, which is managed detection and response. So those things are heavy technology solutions that are looking at all the inputs from your iPhone to your desktop, to the switches to all the stuff inside the business, and it's picking up all these signals whenever you have a corporate device or if you have you bring your own iPhone. You know, most companies will stick some software on there to kind of monitor the business side of it. All that stuff generates tons of data. So back in the old days, you had a SOC and you had a bunch of people sitting behind desks, you know, looking at this massive feed of information. So where AI has actually been extraordinarily helpful because the information has exponentially multiplied as we've gotten more sophisticated in terms of security procedures. There's too much to look at having AI that can actually ingest these security logs, which can be many, many gigabytes of information per day in even a medium sized company. So basically AI will actually lift out things that might be a concern. It'll, you know, maybe take the 1% of all this stuff and say this is stuff you might want to look at. And then you can go back to your security desk, if you will, and they're not looking at everything now. They're looking at the most significant things and making human judgments about that. So AI in that case is enabling technology, not something you can just turn on and be safe with. I'm still hearing from everybody that I'm talking to that AI is a great tool, but still requires A human layer. Not necessarily that AI isn't capable of making the decisions quite yet, it's just that I think most people feel most comfortable if it doesn't. Yeah. And it may be we get to AGI and we could talk about that too, but right now it's not and it does still hallucinate. So if you, I mean, if you think about the stakes, so you're a small to medium business, which is our client base, and you're like, maybe you're regulated, you're a bank or you're a biotech startup or whatever it might be. The cost of a breach isn't just financial, it's life threatening to the business. Right. So if you lose personal information as an example, you can be sued, but you can also have the government come after you. So I think the idea that you want to trust all that to AI, I don't know if that's going to happen in my lifetime because the stakes are simply too high. Even if, even if it gets really good, there's still going to be a chance that it makes a mistake. Yeah. I mean, working in an industry, me personally working in an industry that is far less regulated than, you know, a bank or something that has to do with health care. If I were to build something or leverage an AI platform to foster decisions or drive decisions on my behalf, assuming it's trained well enough, my implications aren't nearly as high. Like I could feel comfortable from a marketing perspective saying, yeah, I feel comfortable just letting it go and having it learn along the way. Whereas if we're talking about higher regulated industries, it obviously needs a human touch. And the other thing I'll toss out is also reputational risk. If you're like a law firm or, you know, we have a lot of like real estate clients, I mean, that sounds like, okay, we're gonna sell the house. No, we're talking about like big office towers or like infrastructure, real estate, you know, so if you screw that up, you know your clients aren't gonna come back and you're not gonna get new ones. So I think the scale increases with not just the regulatory, but like the impact to your business. If you have an event that it's going to make other people that you. Work with sad, I would agree. So one of the questions that I had written out that I, I'm really curious about your perspective on it is how does having the right tech partner help drive organizational growth from someone who works at a tech agency now, but also someone who's Done five startups, how can you kind of put on both hats and yeah, answer that question. Sure. And it took me a while to have a good answer because I didn't come from IT or security. But I've done it long enough now that I think I know. So what we do for a small business is typically done in a much larger one by full time people. So you're going to have a chief Information Security officer, you're going to have a cio, you're going to have IT people that do stuff with computers. You know, you're going to have all these things for a small to medium business, you simply can't afford that. So having essentially a fractional IT security group that scales with the size of your business is huge. Digging into that, I think the most valuable things are going to be occurring around strategy and security. On the strategy side, which vendors do I choose to support my growth? Assuming I'm in a growth phase, things can go to the cloud. What's what things must not on the security side, how do I keep protecting my edge when the sophistication of bad actors increases almost daily? It feels like. So those things are pretty hard to hire in until you're maybe a couple hundred people. So for us, I think those two particular of the seven skill sets, those two are really important. And we make them available fractionally. So you can sort of come in, have us as a trusted advisor and focus on your core business and let us worry about strategy and security on the IT side. Quite there. But when I am, I will definitely look you up. Thank you. So Kirk, you've been great. I give all of my guests 90 seconds at the end of my podcast to plug anything that they're passionate about. So without further ado, the next 90 seconds are yours. Awesome, thanks. So I thought about that because you warned me. So I'm writing, not a full on memoir, but I'm writing up my different startup experiences. So I don't have anything to show yet, but I plan to. And I'll put this out via LinkedIn, maybe a chapter at a time, but I intend to take each of the five startups and just write up a few pages about my experience, my mistakes, the learnings, trying to focus on not just the information, but look at it with humility and humor. Because if you didn't start a company that you can still see on the nasdaq, you know, then you didn't, it didn't work. So for me, I'm going to write those up. This, there'll be five chapters and I'll stick them out there. So that's a passion project now that I'm just starting. Very cool. I can't wait to see progress being made there. Maybe some lessons learned for myself. Thank you. I'd be delighted to share that with you when chapter one is ready. Awesome. Kirk, thank you again for your time today. Ben, it's been a pleasure. Thank you for connecting with me and I've really enjoyed this conversation. Have a great day. Great weekend. Thanks.