How Jonathan Closed $92K In Deals For His Agency

Jonathan reactivated old government and healthcare clients with a new retainer offer, landing two $30k deals and $92k total in revenue. He credits direct outreach, Meta ads, and sales training for breaking his agency's feast-or-famine cycle after 20 years of one-off projects.
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What's going on, guys? I'm here with one of our clients, Jonathan, from Owl House Agency and Owl House Creative, who closed $92,000 just from reactivations working with us so far. Jonathan, how are you?
I'm good. I'm good, Eric.
How are you? I'm good. Do you mind giving us a little bit of backstory on kind of like your agency, how you got into this? Like, I know you had old contacts before. Like, give us a little bit of a rundown if you don't mind.
Yeah, I'll try to give you the quick and dirty version. I started an agency with, with two partners in 2005, so a little over 20 years ago. You know, we had a lot of national clients, we had a lot of healthcare clients, a lot of, you know, we did a lot of documentary work that was sort of socially aware and for good causes and things like that. But, you know, we never really sort of were able to crack having a sort of a retainer model or, you know, we had repeat clients, but it was always just big one-off projects. And sometimes it was 18 or 24 months in between projects and there was nothing really we could do to influence that. It was, you know, these are big national companies with huge marketing teams and they move really slowly. So we were happy to take, take those big jobs, but they aren't, they aren't really a thing that you can bank on every month.
So, yeah. So it was more of like you'd have a big feast or a famine and then it would kind of be, it would be hit or miss like that is what you're saying?
Definitely feast and famine and like over years as well. So some years were, you know, really great. And, and my partner and I were taking home, you know, really nice money. And then other years we were putting money back into the company and, you know, paying, obviously paying our employees before ourselves and things. But yeah, and then I think in the, just in the last 3 years, my business partner's had some success on YouTube outside of our agency together. And, and that's kind of taken his interest. And so he, you know, we're sort of working out a way for him to exit the business in a kind of a graceful way. And so he, with his blessing, you know, any clients that I want to reactivate from our 20 years of client list, he's happy for me to take them and run with them with my new agency. So I'm currently running both businesses. I figure the legacy clients that I've got, you know, with my other business, there's no reason to cut that off. If they want to keep coming back every 18 months, that's great. I'm happy to do those big projects, but I would like to, with this new venture that I'm just starting this year, you know, build something that's a little more scalable and a little more that I can ramp it up and down as I need to, you know, with retainers and repeat clients like that.
So totally. How many, at your peak, how many employees did you guys have in the agency when you guys were running it?
We had, at one point we had 10, 10 or 11 full-time people coming into the office when we were all in an office together. Um, plus then a sort of a roster of freelance camera guys and sound people and color correctors and all sorts of things like that. So, but yeah, you know, like morning team meetings at 10 generally. Yeah. Nice.
Very nice. And I guess like, what was kind of, I know you said it was a lot of the feast and famine, I guess what was kind of the biggest thing you were looking to get solved with us coming in with us? Was it more more of like having a repeatable system to get leads? Was it, you know, also kind of tacking on the retainer side as well so you had more of a stability? Like, what was kind of that main thing, do you feel like?
Yeah, I mean, I think it, it's definitely those two things, you know. More stability from a retainer model I think is very attractive. And then, you know, for the, the 20-odd years that I've had a partner in, in my other business, you know, he managed sales. That was sort of how we divvied it up. He was sales, I was operations. So, you know, getting, getting the projects done is not a problem for me, but learning how to sell. And I think, you know, without disparaging my former business partner, you know, he was very set in his ways and had certain things that he thought would work and certain things that he absolutely refused to try. And I think, you know, with this new business, I want to try some of those things. And, and, and some of that is this sort of, like, you know, more direct marketing to business owners and sort of, you know, getting people to respond through DMs and things like that. So. Yeah.
So I know you closed $92,000 from reactivations. Do you mind going into maybe what types of businesses those were? Like what that looked like? What was that process like? Like how did that kind of come about?
Yeah, it was interesting because it didn't really work the way I thought it was going to, you know, like I developed a new offer after working with you guys over the first couple of months there and sort of had a pretty looking offer sheet to show people. And so I started reaching out to just my entire old client list and, you know, a lot of them were in government or healthcare or worked with a lot of First Nations clients over, over the last decade. And so, you know, not really the client base that I'm now targeting with my new business, but I just reached out to everybody basically saying, hey, I got an exciting new offer and I'd love to chat to you about it. And, you know, I, I'd say maybe 10% of people got back saying they were interested in at least hearing more. And absolutely nobody has taken me up on the actual offer that I got them on the phone to talk about. But, you know, of the ones that I did speak to, now a handful, 5 or 6, I guess, have said, you know, like, I'm not too sure if that will work for us, or, you know, our buying cycle, our marketing buying cycle is 18 months or whatever. So we'll talk to, you know, my boss about this the next time around. But while I've got you on the phone, I've got this project that we really want to get off the ground this month or whatever. Are you interested in bidding on it? And So, you know, I'm not never going to turn that away. So yeah, I've closed, you know, a couple of $30,000 deals and then a couple of smaller, you know, just a single day of shooting and a couple of—
It's not bad at all. I mean, I think just the act of having that conversation with them is great. It's like, even if it didn't work out on the retainers, that's fine because maybe they're not the perfect target market for it anyways. But like we talked about on one of the calls we had too, it's like just talking to them and saying, hey, I have this new thing, would love to talk to you about it. Gets that ball kind of rolling too, I think, which is, which is great. You know, I think a lot of people even just watching this, that, that's what they should be doing is like, if you have past clients, go back, talk to them, see if you can rekindle something because you never know, you know.
No, well, that's exactly what I realized is, you know, just reaching out and saying like, hey, I'd love to chat or whatever. It doesn't, doesn't really open any doors. But this idea of like, hey, I got this exciting new thing I want to show you or that might work for you, even though it it maybe wasn't appropriate.
It was the thing that opened the door to be like, hey, yeah, for sure.
That's all it is. You know, it's just like get a conversation going.
Yeah, yeah, exactly. You're just trying to have a conversation and kind of keep that relationship going so then you can continue to just, you know, rekindle that and see if there is, there is a need or a project or something there at the end of the day.
Yeah, exactly.
I guess, how did you— shifting gears a little bit— how did you come across us and like what kind of made you decide to say, hey, I'm going to pull the trigger with this weird guy in the hat in all these ads, like versus maybe anybody else out there? Like what was kind of the main thing?
Yeah, I remember exactly when it was. I was sitting in my car, I was waiting for my daughter to be done her, uh, her dance class or whatever. And I was just scrolling on Instagram and I was right at the, you know, it was 4 or 5 months ago. So I had just launched the business in January. I was a couple months in and, and really like felt really scattered about what I should be doing and where I should be putting my energy and how do I, you know, build a client base in a new market and an entirely new type of client that I was targeting. And it was one of your, your videos popped up and it, you know, was one of the sort of like, hey, drop a, whatever the word was in the comments below and I'll get back to you. And it was like 7:30 at night. And so I was like, you know, I never do this, but I put the word into the comments and got right back to me. Conversation that I now know was like mostly automated or entirely automated, but got me hooked enough to learn more. And then once I realized that, you know, basically what he could help me do with that exact thing, you know, was to target the business owner who has like concerns, whatever those concerns are, and is sitting in their truck or their car waiting for their kid to be done at baseball and sees my ad and goes, actually, this guy might have the solution, you know. I mean, it doesn't have to work too many times for it to actually pay off either. Like it just has to work a few, few times.
So yeah, absolutely. That's funny. That's good. I love that. I love hearing everybody's stories of like how they found us and how they came across us. And there's everybody's story is so unique, which is awesome. I guess, cause we're still only about 3, 4 months in with you. Like, has there been anything we've talked about so far in the program that you feel like has been particularly helpful for you? Or like has really, you've been like, oh wow, that's super helpful. Like, is there anything specifically? You feel like leads you there?
Yeah, so, so many things. I mean, I think, you know, like, like I was saying before, the sales side of the business wasn't where my knowledge base was and wasn't, I don't think, where my strengths lie. Although I am pretty comfortable talking to clients and stuff, so that, that doesn't sort of scare me, you know. But it's the mechanics of sales, I think, that I, I don't have a basis in. And I think just talking with, you know, you and everybody else, the guys that, that are, you know, running the, the daily sessions and things, and And some of the book recommendations, you know, like I love to read. And so I've just been soaking up these books by people and, you know, some of that is like mind-blowing how, how simple and how kind of driven humans are to always act in the same ways and things, you know, but it's just kind of tapping into those psychological things that humans are prone to do and catching people in the right way, you know? And so that's kind of interesting. Like it's a, it's been a really interesting learning experience and a sort of social experience. Like I'm looking forward to kind of over time testing different ways of getting in front of people and things. And even, you know, I'm part of like a kind of a local entrepreneur group and we were talking about that and nobody is doing this sort of like, you know, Meta ad type of strategy. And people were still talking about putting ads in the newspaper or whatever. And I was like, man, okay, like there's a real, real way to kind of get ahead of a lot of people here, I think, by harnessing some of this, you know, and even some of the AI stuff that's built into the systems. And that you can kind of bolt on or access through, you know, through the automations and the workflows and everything. Yeah, it's a real, real eye-opener. And I'm not like a spring chicken, obviously. Like, I'm—
No, you're very— Yeah, yeah. I mean, you've had a very successful agency for a very long time. It's like this is just kind of a branch off of that. I think it's just like doing things a little bit differently. And like you said, with human psychology, it is super interesting because like once you start to see it, you can't really unsee it and you're like, oh, this is how people think, this is how they operate. And it's like, if you can have your process set up in a way that makes sense for that, then it's like you can get to a great outcome within a conversation with somebody. I think a lot of times people think creative, like creatives think that sales is like this pushy or weird thing, but really it's just like aligning expectations and then helping them get to where they want to go. And if you happen to be that solution, great. If not, then maybe that's a different path. You know, I think that's just really what it comes down to.
Yeah. Yeah. And I think if, if, you know, I, cause I sort of felt the same way that that sales was this sort of, I don't know, whatever, like the dirty underbelly of business or whatever. Yeah. Yeah. But I found like, you know, all you, or what I have kind of enjoyed is finding this like authentic voice or at least something that I believe in that I'm saying, you know, like I'm not just spouting off saying words. You're like, yeah, exactly. I actually have, I think I can help these people with their businesses through what I'm offering. And like, it's not just look at the group you're in.
It's like everyone's still thinking about newspapers and it's like, if you could implement a strategy like what we're doing with you for them, it's like you can truly help these businesses grow at the end.
Exactly. Exactly. Yeah. Yeah. Yeah.
Totally.
Yep.
I love it. I guess kind of a weird question, but like, where do you feel like you might've been if you hadn't taken that kind of leap on yourself and like made an investment into the program, into yourself and your business? Like, where do you feel like you might've been if you hadn't done that?
Yeah, I've, I've thought a bit about that. You know, like I was saying, I, I was, I think there was a lot of flux happening at the time, you know, where I had this sort of established business that had been going steadily for 18 years and then had a couple of really rocky years and my business partner wanted out and all these other things were happening. And, you know, it can be like tumultuous, you know, when you're wondering about like, where's my next paycheck coming from? I wasn't quite at that stage, but, you know, when you're like, I've had a steady salary for all these years now off this business and now I can't actually see that that will continue on necessarily. Um, and so I was, uh, yeah, I was really in a, in a headspace where I needed like a, a line to follow or I needed somebody to kind of give me some structure to, to spend 6 months building something, you know? And, uh, I think, yeah, like your ad came along right at the right time where I was like, this looks like it has exactly the bits and pieces that I need. You know, I'm not knowledgeable on sales and this is very focused on how that mechanically will work as well as kind of, uh, psychologically how it works and and just all the other bits and pieces that go along with it, including right down to like just being on Slack with everybody else going through the same thing is eye-opening, you know, like just hearing everybody else's questions and concerns and yeah, occasionally being able to help or send somebody an example of something I'm working on or whatever is, yeah, it's nice, especially like coming from a place where you have people in an office and you're always working as a team on something to being a kind of solopreneur or whatever. Yeah, it's lonely sometimes.
It is.
It can be. Yeah.
I love being in Slack because I'm like, man, I love seeing everybody and talking with them and having these calls every week because it's like, it's a good source of community of just like, oh, you're struggling with that too. Or like, oh, you're seeing this too. It's like, oh, okay. That's how you did that. That's how you close this deal. And it is, it is nice. I mean, we, we are as, as humans, it's like we need community. We need other people building similar things and being around them because they understand at the end of the day.
Yeah. Yeah, exactly. And that's it. It's sort of, I can talk to my, my wife about it and I do, but yeah, she's not kind of in the in the same, you know, business space or in the same career or whatever. And, and yeah, I think it's different listening to other people who, who are in the exact same problems and same, same world that you're in is really good for sure.
Well, we're pumped you're with us, man. Last question, I guess, if anyone's maybe just on the fence about like they've been seeing our ads, they've been watching some of these case studies, like what would— what advice would you give them around like booking a call or even just speaking with us to see if it's a fit, kind of knowing what you know now, being on the other side of it?
Yeah, I mean, I think I can, I can say sort of like what my biggest hesitations were. Yeah. Kind of when I got to that stage and, and, you know, it was this sort of like, I have X amount of money saved up that I can utilize for, for whatever, you know, that, that isn't untouchable or whatever. And, and not knowing exactly where my income was coming from, you know, as I started this new business, money was the biggest kind of concern, you know, like, do I carve out a big, chunk of the money that I've got sitting here to like run this business for the first year and give it to somebody else to tell me how to run the business for the first year, um, is a bit of a leap of faith, you know, but, uh, yeah, I mean, it, it obviously like has paid off, uh, fourfold or whatever so far. And it's only, I'm only 3 months in. No doubt that once the ads and things start converting that, you know, that'll be a second kind of stream of things as well as like you know, I'm just kind of getting into the cold calling stuff that I had. I'd watched those lessons early on and kind of not done it right away, but I'm just starting that and I'm sure something will come from that. And it's just kind of—
you just did reactivation at this point to get to this, which is great. It's like that was just free money that came in and now it's like, okay, great, let's use that to then launch the ads, get the system set up, get everything going.
Yeah.
And like just bringing in new fresh people who will get on retainer from there, which is huge.
Yeah.
Yeah.
So I think that's probably my advice there is if you're, you know, if you have a business and you know enough, have had a successful enough business to get a couple of years in or whatever, and you're looking to take it to the next level, this investment will pay off right away. Like it, it almost has to, if you kind of follow all the different channels.
If you do the work, right? That's what I was going to say.
Exactly. Yeah.
Like you just have to put the work in.
Yeah. Yeah. Yeah. Yeah.
Love it.
Yeah.
Well, Jonathan, we'll do another one of these once we got ads up and running and we're cranking deals from that. And I appreciate your time as always. And we're excited you're with us. Let's keep going.
Awesome. Thanks, Eric. Yeah.
Yes, sir.










