Accidentally Running a Firm: A Journey from Freelancer to Boutique Firm with Miles Kailburn | Episode 177

Greg Alexander:

Hey, there, everybody. This is Greg Alexander, Founder of Collective 54. You’re listening to the Pro Serve podcast to show dedication to helping founders of thriving boutique professional services firms to grow, scale, and maybe some day exit their firms. And on today’s episode, we’ve got an interesting story and I think this story is going to resonate with everybody and that is some of us have started our firms kind of accidentally. We accidentally acted like a, for a number of years. And then the business grew and grew. And then we wake up one day and we say, jeez maybe I got something and I wanna go from this kind of freelance business model and try to build a real firm. We call that a boutique and try to scale it to something substantial that might be a wealth creation asset for the founder. So that’s what we’re going to explore today. And with us to help us explore, this is somebody who lived that very journey. He’s a longstanding well respected Collective 54 member. His name is Miles Kailburn, and Miles, would you please introduce yourself to the audience?

Miles Kailburn:

Certainly. Thanks, Greg. My name is Miles Kailburn, I’m one of the Co-Founders and CEO, at Old Town Media. We’re located here in Fort Collins, Colorado. And we’re a marketing firm that focuses on high lifetime value segments. So, medical automotive, housing, B2B pro serve those types of industries. And really behind all that is our customer journey work. So that’s the segment we’ve found ourselves in after 17 years.

Greg Alexander:

Okay. So speaking of 17 years, when you and I were speaking last, you said something to me that really stuck. And there was the reason why I asked you to be on the show and you said, listen, I accidentally ran my firm for years. So let’s hit the rewind button and go all the way back to that time period and tell everybody how the firm started, why you feel you accidentally ran it for that long? How long did that last kind of put some color around that for us?

Miles Kailburn:

Yeah, certainly it’s something that’s made us feel a little awkward. So, I think a lot of excuse me, a lot of businesses start out, you know, have this perception. They start out with this grand vision and they set out business plan to execute it and it’s just linear path. And, and our path was definitely not that at all. You know, my wife and I moved out from new York. We moved to Colorado, and she was finishing her college undergrad in design and she decided that she would do some freelance work and my background was in it. So we kinda looked at the numbers and said, hey, you could do a couple of freelance projects. While you’re going through college, you’ll make the same amount of money that you would be making work on a college job and get some experience. And so we kind of started down that path. I moonlight Ed for her writing some code, you know, she’s really just kind of a small boutique little, I shouldn’t even say boutique freelancer building web projects. And so that started to five to six ish and it slowly just kind of built on itself. I left my it consulting gig and joined her fulltime probably around 2007. And we reincorporated as otm at that point and started to just run that model. We didn’t know what the model was. We didn’t know what we’re doing. We were focused on the craft and… excuse me, couple of years into that process, you find yourself with an employee and then you find yourself looking for office space, you know, a massive 600 square foot office and you sign that lease and… you know, every year or so probably about every year we’d added a team member. So probably around 2009. Well, you know, we’ll skip right over 2008. We grew through 2008. You know, we were a small company growing through that. We didn’t know what a recession was. So, so we fared pretty well through that kept growing. And I think around 2009 or so, we had four or five people. And, and that was probably around the first time that we kind of looked around the office, and there is this moment of it’s no longer this side gig, freelance model. You know, we have stable recurring revenue. We have team members who have mortgages and there is a strong co dependence and there is this just kind of moment of we actually, I think we have a company here. I think that’s what this is now.

Greg Alexander:

It’s such a great story and you shouldn’t feel awkward about it because I will tell you, I’ve heard that story dozens of times inside collected 54. I think that is a common way that professional services firms get founded. Many of us might not have the courage to admit it like you were doing here publicly, so, thank you for that, but I think that’s, a very common way. I wanna hone in on the moment that you said, jeez there’s a co dependency here. We’ve got employees, they got mortgages, you had this sense of obligation, continue to provide employment to these people and of course, you were dependent on them because they were doing the work and, you know, helping you pay the bills and all that. When did you decide to go for it? To say we’re going to really try to scale this thing and like, and what was the motivation? Because it sounded like you and your wife had a heck of a nice lifestyle. There wasn’t a lot of stress, happy clients. You, you blew right through the greatest recession, you’ll ever see in your life and didn’t realize what happened. So, like why I screw that up and go for it?

Miles Kailburn:

You know, when we started the business, I don’t know, we were 20 and 21, maybe we had no idea what we were doing. You know, we’ll say business but, you know, freelancer then incorporating as a business and all that. It kind of hit in two stages. The first stage was recognizing that co-dependence and then realizing, shoot, there’s a whole lot to this that we don’t know. We need to go figure out HR. We need to figure out payroll. We need to figure out all these other systems that really were not part of the vision to date of the company. But we love the team. We love the people that we’re working with. And so I would say that was kind of the first toe in the water around building that and it was just out of, you know, obvious necessity. I would say the crazy part is, I think, you know, that aha moment was really closer to 2016 to 2018 for us, which is kind of wild, you know, it’s nine to 11 years into our journey. But, you know, when we talk about how we started it, you know, we started the business and we accidentally kept going. It was really around that 2016 time when we had probably closer to nine or 10 team members. We actually started to understand systems and processes and start to look at a sales engine and how do we actually build this? And that really was the start of we have to, we have to run this as a mature organization. And that’s really where we started to look everywhere. Ironically, the last place we looked at were agencies, you know, in my opinion, and I think you would probably share, the traditional agency model doesn’t really scale that well. Ironically, I just read a research paper in my inbox maybe a week ago and I kid you not the actual title of it was digital agencies don’t scale and let us help you grow. And I was like, no, no, we’re actually doing the other thing and it works very well and you actually need to scale. And so 2016 is, you know, that’s when we started it and,