
Brian Skowron | Lullabot
The Inflection Podcast · 2025-12-10 · 33 min
Substance score
39 / 100
Five dimensions, 20 points each
What our scoring noted
Our reviewer’s read on each dimension, with quotes from the episode.
Insight Density
The episode is predominantly biographical narrative and mutual rapport-building, with only a handful of substantive ideas surfacing—the egg-timer reset technique and the 'humanity as scarce commodity' observation. Most of the runtime is personal anecdote and platitude with very little a B2B operator couldn't already articulate themselves.
be authentic, right? In the world of AI and so many distractions, I think authenticity as humans, I think goes a long way
Embrace knowing what you don't know. Embrace collaboration. Make intentional space.
Originality
The father's reframing—that people, not companies, are the permanent institutions—is a genuinely interesting inversion and the episode's sole standout idea. Everything else (AI threatening human connection, be authentic, mentorship matters) is well-worn territory circulating widely across business media.
I used to always kind of think of companies as these, like big permanent institutions...as I look back on my career...I realized that I had that totally backwards. And it's actually the people that are the permanent institutions and the companies come and go.
get yourself a physical, like an egg timer...whenever it goes off, reset, reset the call
Guest Caliber
Brian Skowron is a legitimate practitioner who grew from cold-calling managed hosting into president of a real digital agency executing state-government-scale platform work; he has genuine operational depth. However, he is not a widely influential operator and the conversation never extracts the institutional knowledge his tenure should contain.
We were the company that, you know, built Georgia's web infrastructure, which platform called GovHub. We built Iowa's DX platform which runs all of the Iowa.gov sites.
That was in 2011. And you know, over time, over the years, it's been really, really amazing to see Lullabot grow and evolve.
Specificity & Evidence
The episode is strong on biographical specifics—named mentors, named clients, salary figures, years, and a memorable first-sale story—but almost entirely absent of operational or business metrics (revenue, growth rates, deal sizes, conversion rates) that would make it useful to a B2B practitioner.
I sold a single dedicated server to the Apollo Theater. And Ron Dixon was the guy I worked with.
I think it was like 23,000 a year or gosh...may have gotten a raise, like negotiator raise to 26,000
Conversational Craft
The host is warm but routinely pivots away from the guest to narrate their own career story at length, never asks a sharp follow-up, never challenges a claim, and closes with a bullet-point summary rather than deeper excavation. The result is a collegial chat rather than an interview that extracts genuine insight.
I remember Demetrius, he's gonna Get a shout out here, Barnes. He was at Colony American Hubs at the time...I had put out so many applications, applied so many places
It's been phenomenal to have you on Brian. Thank you so much. What a fitting way to end that with such a powerful quote.
Conversation analysis
Computed from the transcript - who did the talking, and the verbal tics along the way.
Share of words spoken
- Speaker A67%
- Speaker B33%
Filler words
Episode notes
Brian Skowron, President of the digital agency Lullabot, takes us on a candid journey from his dreams of sports broadcasting to navigating the cutthroat world of New York media sales on a non-living wage. He shares the intense "crushing anxiety" of his first tech sales job—cold-calling to sell complex server hosting to clients who knew more than he did. This pivotal moment of feeling "so far over my head" became the engine for his future success. Discover the unexpected lessons he took from a college professor that still drive his high-level business meetings today, the importance of mentorship, and the career leap that led him to cold-call Lullabot's co-founder and eventually become its President. Brian also shares an incredible insight from his father that redefined his perspective on business and career longevity: "The people are the permanent institutions, and the companies come and go" . Tune in to learn how to turn your greatest professional anxieties into your biggest inflection points.
Full transcript
33 minTranscribed and scored by The B2B Podcast Index.
It was cold calling. It was prospecting, it was make business happen. And it was that, I can tell you, was a defining point in my career, in my life, because that was the first time in my life where I felt completely without options. I had to make that, that job successful. And I was in so far over my head. I was cold calling to try to sell something that is incredibly complex and technical, that I didn't understand. And I was selling it to people who knew it way more than I did. Gosh, it was jumping the deep end. It was incredibly intimidating. And, you know, I wasn't successful at it for, for a while. I just remember having this, like, crushing anxiety of, like every day. I felt like I was going to get fired because I hadn't sold a single thing. Yellow. Welcome to another episode of the podcast with me, your host today, Anabi. Exciting to have Brian Scar on with me from Lullabot. He's the president over at Lullabot. And happy to have you on, Brian. Yeah, happy to be here. Thanks for inviting me in. Yeah. It's been a minute. Thank you. Is it a minute of us chatting to come on board? And I'm so stoked. Schedules worked out to get into it. Your background is very fascinating to me with your start in radio, sports broadcasting leading up to this moment. So if you will, let's chart a course, a whirlwind tour of your experience leading up to this moment and an inflection point along the way. Yeah, yeah, for sure. Gosh, I don't know if my story is very exciting, but yeah, it definitely started in the world of radio, tv, film, or at least thought that's where I was going to go. I remember when we. One of the first times we met in person, I was at your office space where your podcast studio was. And I remember I was like, ah, like that brings back warm feelings, like seeing the studio with the microphones and everything else. So this is exciting to be here, but yeah, to, I guess to tell the story. So I went to school and got my degree in radio, tv, film at the University of North Texas. And in my young naive days, I thought I wanted to be a sports broadcaster and do sports talk radio and, you know, ended up maybe against better judgment, trying to pursue that, not knowing what career prospects were going to be like in that world. And one of the things that was super cool about the University of North Texas is it's a major radio market. You know, it's one of the top five radio markets. And the campus radio station, there's another Huge radio station. As far as radio stations go, it was a, they had like a, I think a hundred thousand watt signal or something like that. I don't know what that means, but it sounds like a lot. Yeah, yeah, I covered the whole metroplex, which was, you know, intimidating, but also really cool as a college student. So I volunteered for the campus radio station. And what was really neat about that, being in such a big media market, that radio station had standing press passes with some professional sports teams like the Dallas Stars, the Dallas Mavericks, Texas Rangers, and so got to kind of participate in that and go, you know, be in the, in the press box and those sorts of things, which was really, really cool for, you know, a kid in his, in his early 20s. Right. But, but yeah, one of the things that I remember fondly from that time was I was in a class with that was taught by an adjunct professor named Bill Mercer, who used to be the play by play announcer for the Dallas Cowboys way back in the day. And this class, he would just flat out like, send us to, to high school football games in the area and have us sit there with a microphone and do the play by play of a, of a game. It occurred live. Right. Oh my gosh. And first of all, that is so difficult. I have much respect for the people that can do that because I learned very quickly that I could absolutely not do that. And secondly, this, this guy, he was incredible because he had this amazing career. But what he did in the class was he would take all of our painful sports audio and listen to all of it and then write handwritten notes and suggestions. Dedication right there. Yeah. So it was just a really cool experience. And you know, the thing that like impacted that, that still sticks with me today and impacts, you know, my career in technology was when you're calling a game like they have, you know, one of the things that he, he recommended was he said, you know, get yourself a physical, like an egg timer. You know, like the little thing you turn that goes like. He was like, do that, set it for a minute at a time and just like whenever that goes off, have it next to you. And whenever it goes off, reset, reset the call. And what that means is like, basically, you know, you do the thing that sportscasters do, which is they say like it's, you know, third quarter, fourth down and this team is up by 12. Just sort of sets the, like resets, gets everybody on the same page and you don't really realize that it kind of fades into the background. But when you watch a, a sports broadcast like, that's what they do, and they do it just about every minute. And, you know, that ended up being a really useful device that I still use today, like when I'm in meetings and calls or conversations, one on ones to just kind of occasionally, not every minute, but occasionally, like, reset, remind, and, you know, get everybody aligned on, like, why we here? Why are we having this conversation? What are we hoping to get out of it? And that's really good. You know, it ends up just kind of being a thing. So, yeah, that was the start. And then eventually I graduated with a radio, tv, film degree, had very few job prospects, worked in media sales, met my now wife, and we both moved to New York in our early 20s. And in New York, that's really kind of where I started in technology. So she got a job, transferred, she got a promotion, which was great. And, you know, she's really the. She's the superstar in our household for sure. But, you know, I kind of tagged along and, you know, had to figure out how to make my career fit this new environment, this new city. That's applaudable. That's applaudable that she got the promotion. And you guys were like, yep, we're. We're doing it. And you went along. That's. That's great. You know, when you're young, that's the time for crazy swings, right? Yeah. Cool. It felt very. I remember it felt very scary and exhilarating at the time, but, yeah, and, you know, it's. No regrets at all. My life today is. Is hashtag, no regrets. Yeah. I think my life is what it is because I made that leap. Wow. And the net appeared. That's a fascinating thing with these leaps, inflection point, pivotal moments. Sometimes we don't notice them in the moment, and sometimes we can, but many times it's. In hindsight, you're like, whoa, that happened. So this could happen. So this could happen. And here I am right now. And then you're grateful that you made that leap. How long were you all in New York for after that move? We were there for three years. We were there from 2005 to 2008. We moved back right before the financial crash. Yeah, it was an interesting time to be in New York. It was a fun time to be in New York. And we go back. I go back for work somewhat frequently, and it's been fascinating to watch that city change because we lived in Astoria, and at the time, like, Long Island City, if you know the area, it was like nothing. And now there's, like, high Rise buildings for days. It's kind of where all the development's happening. It's pretty wild. Oh my gosh. Yes. So you got your start there in tech. Move, moved to New York, got a taste for tech. I know at some point you got into open source or you, you like open now. What's the, what's the connection there? Or was that where you got open source initial taste? Yeah, I think this is where I ended up getting into technology. Okay. Open source kind of came later. So in New York, you know, when, when you talk about, when we talk about it being a leap and really being an inflection point or a turning point in my life and in my career if I could paint a picture, basically we ended up moving to New York. I moved and got a sales assistant job with like Fox Sports or not Fox Sports, Fox Station sales, which was like a Fox owned company that represented, that sold advertising for like TV stations, basically did not enjoy that work environment at all and very quickly was like, I've just got to get out of there. And it paid nothing. It, it paid a non living living wage in New York. Basically. Yeah. I think it was like 23,000 a year or gosh, what we made was he that plus commission or just that that was, was like 23,500, something like that. Gosh, may have gotten a raise, like negotiator raise to 26,000. But it was, it was not a lot. And you know, it was teaching something though. So pay was crappy or maybe that was less. But what did you walk away from that with? You did that sales thing and you're like, nope, not for me. That could be the experience. But like, what would you say? That's a good question. I mean, I don't want to be unkind to anybody. Yeah. But I think really like when I think about that time, you know, I think the thing that that experience gave me was a real clear picture of the type of manager or the type of working environment I didn't want to create. Nice. You know, which I would say is, was one of, you know, aggressiveness, confrontation, you know, not a lot of, you know, shared morale or culture. I, I left with a really clear idea of like, that's not, that's not me, that's not who I am. I don't want to be in an environment like that, nor do I want to create one in the future. Makes sense. Yep. So, you know, I was really looking for any sort of escape valve out of that and I ended up interviewing and getting an introduction to A hosting company. Because this. Web hosting. Yeah, Web hosting. Okay. This is back in the day of dedicated server hosting, managed server hosting. If you remember those days, how far things have come. Yeah. So I. I got an opportunity to be a salesperson for a managed hosting company that's no longer around. It was called logicworks at the time. It was, if you can imagine, the role was like, basically, congratulations, you are now a salesperson for this managed hosting company. Oh, sell business. Like, I was, I don't know, four, maybe 23. I don't remember how old I was, but it was cold calling. It was prospecting. It was make business happen. And it was that, I can tell you, was a defining point in my career, in my life, because that was the first time in my life where I felt completely without options. I had to make that. That job successful. And I was in so far over my head. I was cold calling to try to sell something that is incredibly complex and technical, that I didn't understand. And I was selling it to people who knew it way more than I did. Gosh, yeah, it was jumping the deep end. It was incredibly intimidating. And, you know, I wasn't successful at it for. For a while. It was. I just remember having this, like, crushing anxiety of, like, every day. I felt like I was gonna get fired because I hadn't sold a single thing. I was there for several months, and I think it was like, month three or month around. About month three. I was just waiting for the other shoe to drop, but kept going. Had, you know, a mentor within the company named Ben Friedman, who I'm still friends with today, who, you know, kind of taught me a lot about sales and taught me a lot about, you know, technology and just sort of how to have the drive to keep going. And, you know, yes, it was. I had to make it work. And so I remember the first sale I ever made, it was with. I sold a single dedicated server to the Apollo Theater. And Ron Dixon was the guy I worked with. And a while, like a couple of years ago, I looked him up on LinkedIn, and I was just like, hey, man, thank you. Like, thank you for taking video on this poor young kid trying to sell things. But, yeah. Oh, my gosh, that is incredible. That is incredible. I remember my first tech gig in the US And I had done so many interviews trying to get a SQL database developer role. I did, like, an internship or apprenticeship to get into the space, so that was my kind of first experience. But I did, like, the first paying gig. And I remember Demetrius, he's gonna Get a shout out here, Barnes. He was at Colony American Hubs at the time, and I interviewed with him. I had put out so many applications, applied so many places, and I was falling into the conundrum of, you seem to know the stuff you've done, apprenticeship, you learned some things, but we need to have real experience, real work experience. I know Company wanted to be that first company to give me experience. And I interviewed with him, and he knew that, and he was like, you know, I like your aptitude. You know, you're excited, you're passionate, and, yeah, let's do it. I'll give you a chance. And I just. That was a defining moment for me because Dago Me started officially in tech in the US and after that, I was able to, you know, grow. And, you know, I've worked for companies like Microsoft, Zell and Dell, but I still look back and I'm like, wow, that was the start. So I thought about him, because few years ago, same thing. I was like, hey, man, thank you so much for that opportunity. Because that started a chain reaction for a lot more that he probably never even saw. He just gave me a chance and that was all I needed. Sometimes that's all it takes. Like, sometimes, you know, those. Those sweet people in life that see something and just take a. Take a chance and, you know, make a high risk bet on somebody. I. I had a similar thing at that same job. It was my manager, Greg Kitaev. Like, I remember, he was like, listen. Because I was like, I don't understand this technology. And he's like, well, you know, like, you, you. You're smart, like, you've done your homework. You can, like, I think you can figure out what you need to figure out here. And, you know, like, as I was continually freaking out, having not sold anything, and wondering when I was going to get fired, he was like, listen, you're doing the right things. Give it time. It'll work out. You know, try to remember that and give people grace that I work with today, because, you know, if somebody extended that kindness to you, like, you really ought to pay it back as much as possible in your career. Absolutely. Hard to remember to do that sometimes. Yeah. Especially in the moment when someone's getting unnerved. Come on. Oh, gosh. Yeah. But, yeah. So let's talk about Lulibut. So fast forward, you're president of Lulibut. I don't think you started off being president at Lilabot. What did that look like? And if you will talk a little bit more about what Lillabot does for those who are listening. Sure, yeah. Um, yeah. So, I mean, Lullabot is an amazing company. It's the best company I've ever worked at in my entire life and I hope to retire from Lullabot one day. Amazing. Yeah. So Lullabot is a digital agency that's kind of the short version, but we do strategy, design, development. We have expertise in, you know, large scale platforms and systems of sites. We have become very well known in the state government space. We were the company that, you know, built Georgia's web infrastructure, which platform called GovHub. We built Iowa's DX platform which runs all of the Iowa.gov sites. And we have done similar work with Massachusetts, we're working with Maryland and now Arizona. But you know, we, we sort of had our roots in Drupal, which is an open source technology, open source content management system over the years. Lullabot's been around since 2006. We've worked with so many different household names and you know, kind of large brands across lots and lots of different industries. And I've been blessed and fortunate to have some amazing experiences with those clients and with coworkers that I respect and admire and have worked with for years. So how did I end up there? Yeah, so the connective tissue between the managed hosting to here to Lullaby was, you know, I ended up, when we left New York, I ended up working for another managed hosting company and incidentally ended up cold calling the co founder of Lullabot at the time whose name was Matt Westgate and you know, basically tried to manage hosting services to Matt and you know, we ended up hitting it off and did a few projects together. And then, you know, the hosting company I was working with at the time, also out of business now is, was. Was kind of like the host of record for Lullaby and when that managed hosting company got acquired and started to, you know, go a different direction, I was in touch with, with Matt and he was like, hey listen, we love working with you, you're great. We need a sales manager. Would you be interested in working with us? And I was like, okay, sure. That was, that was another leap at the time, you know, because it was a, it was a different type of company. It was a different, it was a pay cut at the time and you know, it kind of sent me down a different path. And then that was in 2011. And you know, over time, over the years, it's been really, really amazing to see Lullabot grow and evolve. It's been. The two co founders have since exited the Business. The business is now employee owned, which is amazing. Inspiring. It, you know, is something that I, like, feel genuinely good about being a part of. Yeah. And we're working with organizations to make their digital services better in a way that impacts humans. It's. It's pretty cool. You know, it also pays my bills, which is nice. Hey, that's. That's nice. Icing on the cake. It's. It's interesting because I was just having a conversation on another podcast recently, and we talked about technology, right? Digital analog technology in general is. Is made typically for humans. Like technology rarely. Often exists in a vacuum for the sake of this technology doing its thing. Like, usually has a funk. Funk could be humans, right. Or even animals, but usually that's humans orchestrating that. What we're seeing increasingly is, you know, many tech companies, right. And those who build technology, forgetting the humans in the first place. You optimize the heck out of the technology. You build it. But it's like the humans are like, this is not usable. I hate this. This doesn't solve my needs. So I think we're going to see increasingly a shift towards human centric design. And, you know, how can we build this for the humans in the first place? Focus on cx. My new role now with Colorado, Right, is the CX customer experience. And I think that's a shift we're beginning to see with the rise of frontier technology and cutting edge technology like AI. It's like, wait, what's the point of all of this? It's meant for human thriving in the first place. Let's not lose sight of that. So that's something that stood out to me with you and what Lullaby is doing. And you and I have had multiple conversations, singing in action, singing at conferences. I know that's something I really enjoy now. Y' all have grown since 2006. You've had some pretty significant projects and collaborators, but I think the one thread that I've seen is just that obsession, human centric aspect to what you do. So I applaud that and excited to see us and hopefully collaborate some more. Sweet. Yeah. As we go down the road. I'm glad you brought that up, actually, because one of our core values is. Is to be human. Like, be human is one of our core values. And it seems to be the one that resonates the most with our team. And, you know, people can kind of roll their eyes at, like, company values sometimes, you know. Yeah. A lot of times they can be kind of empty. But we try to walk the walk and what's really interesting. In the past few years, I feel like being human has kind of been under direct assault with a lot of the emerging AI and automation tool tooling and, you know, those sorts of things. And there was somebody who mentioned, I can't take credit for this, somebody, another digital agency friend in a conversation, I forget exactly who said it, but somebody was kind of prognosticating about AI and they made the point of like, you know, when, when artificial intelligence is ubiquitous and everybody has the same kind of abilities because AI grants those abilities, humanity is going to be the scarce commodity. And it really sort of made me think a bit. And it's like, yeah, you know, like that's going to be harder and harder to find, like really true, true human interactions and things that feel genuine, authentic. You know, just this week, yesterday I was trying to set up an appointment with an air conditioning company to do some maintenance in my house and I was surprised, like calling to make the appointment. I talked to an AI agent which was very seamless, seamless, polished, but clearly AI, right. And that kicked me into a scheduling queue. And they're actually supposed to arrive at some point today, I don't know what time, called their office line to try to figure out roughly what time eventually got to human, who said, okay, like I'll kick you to like, I'll leave a message for our scheduler and they'll try to contact you at some point today. And it's like, wow, all of that, all of those layers are designed to eliminate human interaction. And like here I am, the customer paying, and I don't have a basic answer as to like when these folks are coming to my house. And that's just like one service. Yeah, I feel like there are so many services and interactions and digital touchpoints that are going to have similar frustrations and similar opacity. And you know, I feel like there is a differentiator and an opportunity to really create smartly smart interactions that, you know, enhance human experience and like showcase it and bring it to the forefront rather than automated away. And that's what I feel more excited about. I could not agree more. I could not agree more. There's a promise of AI and cutting edge technology. I'll put it all together. But yes, I think increasingly coming back to why we're building those in the first place for human should be key. I mean, I've even been thinking about it for my daughters for now. I have two daughters. Right. One of the key things, as they get older, we want to teach them is it might Sound funny and cheesy, but it's like literally how to be human. Yeah. Like, you know, how can we teach them how to do that better? Right. Speaking. How do you pass a, a point across? How can you convince people? How can you make friends? I can get in a room. Right. And be able to read the room and make connections. How do you, you know, not to put on events like the, the human things, Shake hands like someone in the eyes and be direct like things like that. Right. Where I think for our kids growing up with a lot of technology, though some of those human esque interactions might be harder. I mean, as a pro. Covid, when Covid happened and many kids were not in school, even for adults, a lot of us were not in office where like we laughed about it because you meet someone and you're like, do I shake? Do I fist bump? Do I? And it was kind of, you know, like kind of awkward. So we need practice point I'm trying to make and to the degree we can. Right. We want to provide those opportunities as much as possible for practicing being human. Well, your, your kids have the best teacher as far as, I mean, I have to say I've always been impressed at people who both naturally and genuinely connect with people. And I, I've seen that with you, like from the jump. Um, I don't know that I've ever seen someone just be like, hey, have you met this person? Have you met this person, like, and know everybody, like on a personal human level, not just like, these are professional colleagues. And I always admire that does not come naturally for me after working. Hey, you do, you do great, man. You hold your own. But there is a quote you had that I don't want to forget that you had shared like a dad quote. And do you, do you want to share it? I have it written right here. Yeah. So I mean, talking about the human element, right. I admire my dad in a lot of ways and I look up to him. He's retired now. He was a manufacturing engineer for most of his career and worked at a lot of interesting companies. But he retired a few years ago and I can't remember how we got on the topic, but you know, one of the things that he said that just really like shifted my way of thinking about things was, you know, he was saying that as he was toward the end of his career, reflecting back on it, he said, you know, listen, I used to always kind of think of companies as these, like big permanent institutions. You know, I worked, you know, he worked with companies like Ingersoll Rand and you know, Lockheed Martin, like all of these kind of like big recognizable, long standing companies, right? And he said, I used to think of these companies as, as permanent institutions and you know, we as people get jobs within those companies. Like, you know, the people come and go and IBM continues on, right? But he was like, as I look back on my career and kind of the twists and turns it's gone through, I realized that I had that totally backwards. And it's actually the people that are the permanent institutions and the companies come and go. Companies change ownership, companies go in and out of business. With any particular industry niche or vertical or space that you operate in, it's relatively, it's a community, right? Like it's a small community of people. And those people are, if you stay in the same career, they tend to be there for most of your career. And so really as much as you try to do right by your employer or your company, you gotta always do right by your people and the people around you, whether or not they're like co workers, employees, competitors, you know, this is like we're all humans. Yeah, I don't know. That's a great quote. That quote just really resonated with me and I try to remind myself of it all the time. Especially when, you know, like businesses is taking us down, funny twists and turns. It's like, yeah, you know what, we're on this roller coaster together, man, that is striking. Thank you so much for sharing that. It's been phenomenal to have you on Brian. Thank you so much. What a fitting way to end that with such a powerful quote. I'll make sure I add that to show notes, but there's something you sent to me and I thought was super cool. I love the way your mind worked. You sort of put, you know, the lessons learned in the different chapters and I'm going to read them out. I also add these to show notes, right? So from the radio, tv, film, background you had one key lesson. That was the egg timer, the reset. Learning how to reset, pause, reset and get things going. And kind of like time boxing, I call that a pomodoro. There's a pomodoro timers like a tomato. So I literally use that right now in my life sometimes and I need to do deep work, right? 15 minutes prints, 25 minute, whatever it is so I can go deep and you come up for air and then you, you know, reset it again and go in. So there is that. So the reset. And then with your move to New York, two things. Say what you need to quickly and shut up. I didn't want to be the first on this podcast. No, no, that sounds good. This was good. Then be authentic, right? In the world of AI and so many distractions, I think authenticity as humans, I think goes a long way. And then for digital and open source, three things. Embrace knowing what you don't know. Embrace collaboration. Make intentional space. And there is a fourth lesson that I add, and I think this applies all across, is mentorship. The importance of mentorship, that has been a recurring theme through this. But a lot of people, like I had this mentor and this person that took a chance on me, so that's another one that really stands up. Then it's obviously your dad's quote, which I will summarize. As you know, humans, people are the permanent institutions and companies come and go. So thank you, sir, for the words of wisdom. Was awesome to have you on today. Thank you. Yeah, this was fun. I wish we could do. Do it longer. It's always fun talking with you. Let's do more. Yeah, definitely.