Sam Penny (00:00)
Most agency owners don't own a business. own a high pressure 80 hour a week job with their name on the invoice. They chase more clients, they chase more revenue, they chase the next milestone. But more clients without systems isn't growth, it's acceleration towards burnout. Jesse Gilmore saw this trap from both sides. He built a business.
That pretty much became a cage. He then spent five years inside a $4 billion corporation, eliminating single points of failure. Now he helps agency founders do something radical, fire themselves from the daily grind, from the bottlenecks, from being the hero. Today, we're talking about leverage, ego, identity, and why your business cannot outgrow you. This is Jesse Gilmore. Jesse, welcome to the show.
Jesse P. Gilmore (00:44)
Sam, thank you so much for an awesome intro. Excited for our conversation.
Sam Penny (00:48)
Mate, I'm looking forward to this. You know, when you're talking about firing the founder, it's always a very difficult subject for entrepreneurs, but it's always so important. ⁓ Now, I wanna go back to the start though, because you worked inside a $4 billion blueprint, I think is probably the best way to describe it, where you were eliminating single points of failure. Tell me about that.
Jesse P. Gilmore (01:10)
Yeah, so the time in corporate America was actually in between my third and fourth business. And my first businesses were all based around my skills. I didn't know about processes and systems. And when I joined corporate America, was pretty funny. My mentor at the time, was like, she's like, all right, well, here's three months worth of projects. You know, here you go. And it took me three weeks to get it done. And she was like, all right, well, you're a little different than the usual. I'm going to give you a project that you can't complete really quick.
And she started talking about how a lot of the people that were working within the corporation were getting close to retirement. And the things that were kind of in their head were tribal knowledge of that the business basically could not function as it has or the customer not being impacted if they ended up going on retirement. So ⁓ she set me on this kind of journey as you develop and remove what's called single points of failure.
by developing the processes, the systems, the training to build it in. And during that time in corporate America, I started realizing that the thing that I was learning in corporate America was actually a thing that was missing in my previous businesses. And so I started understanding a lot more about processes and systems and duplication and good delegation. And I started understanding that, holy cow, I think I'm finding something that's extremely valuable. And that was a skill that kind of started Niche Control because
That $4 billion global corporation, the business unit that I was working in got sold for $180 million. And I started realizing that the acquisition would have never happened if the systems and processes would have never been created. And so that kind of sparked the desire to launch Niche and Control, which is our company. And it was all really based around kind of helping founders that might've been in the same spot that I was to remove single points of failure, which ultimately for a lot of them is the actual founder.
Sam Penny (03:05)
Let's talk about those businesses you had before, Jesse, because from what I understand, from my research, they are quite creative. What were they?
Jesse P. Gilmore (03:12)
Mm-hmm.
Yeah. So the first one was called the North Coast Collective. We basically were promoting the arts and culture of Minnesota and developing like ⁓ band pages and visual artists pages and everything based around Minnesota. And so as more kind of like artists kind of came in, we'd promote their show on our website and ⁓ we're basically doing what people do on like written publications, but we started doing it with social media and. ⁓
and it was kind of like a web information services business. That business in itself took a long time to get a proof of concept out. This was back in 2006 and MySpace was really popular and like Facebook was just starting, you know, and during that time we were kind of a little bit more innovative with what we were doing. So that proof of concept took about three years to actually get out, which is way longer than I ever suggest anybody has a proof of concept out.
But what happened was that because I didn't really understand processes, systems, duplication, and every time I tried to delegate, it just didn't work. I was starting to work 60, 80-hour weeks for years, and I started losing the vision of the business. And as the business finally was starting to become more successful, I was kind dying on the inside. And I joined entrepreneurship because I wanted freedom.
Sam Penny (04:32)
Yeah
Jesse P. Gilmore (04:36)
I had created something that was more like a monster. It took more than what it gave. And so I actually dissolved the business as it was becoming successful. And on the outside, people were like, ⁓ it's just, you know, it's amazing. know, why did it end? And I had to go through this kind of like understanding that what they saw was not how I felt. anyway, I could go longer into that. That's part of the book that I wrote.
What I thought was is I thought it was just that business. So then I started a second one, which was a fine arts photography business. I was traveling all around the world and taking pictures and then selling it that way. But again, that was all based around my skills. And if I wasn't there, work didn't get done. And then the third one was a nonprofit organization. And it was helping volunteers, like basically like event promotion, kind of like fundraising for volunteers to do conservation work around the world. And when
I was doing each one of those, I just kept on creating myself a job. And I didn't really understand how to break out of that. So those were those first companies. But all three of them, I just realized that it wasn't creating that freedom and I needed to kind of learn some things. ⁓
Sam Penny (05:45)
those three businesses and also with your photography, you're obviously quite a creative and you've been immersed in a world where you're dealing with a lot of creatives, where systems and creativity don't necessarily come together. When you look inside a six figure agency today, what are the most obvious single points of failure to you?
Jesse P. Gilmore (06:08)
The founder, the founder that is constantly like the central place. So everything running through the founder, like they're, queuing on things, they're developing the strategy, they're being a project manager for the execution. And a lot of it actually has to do with not getting everything that's in their head into something that could do the same type of work, the same kind of like QA. Like for an example, I was working with a creative agency earlier this morning.
on a one-on-one call and a lot of it was based around just understanding what is the 80 % of a website design and development project that's the same. And then let's streamline and systemize as much as we can and then that way you can focus on the 20%. And that was kind of like a light bulb moment for her where she started realizing that if we did that with the website project, we could do that with other services which means that she can kind of elevate. And the QA.
process of like checking to make sure it's at the same quality as she was trying to create. That's all kind of like in her head and like you know if you just took that and made it into a QA checklist and then gave it to the developer. Holy cow, it just changes like everything you know. ⁓ So that's pretty pretty typical. Everything is kind of in their head and they don't. They don't really ⁓ view systems as a way of actually being more creative.
And it takes a couple of times of talking through that the majority of your work actually for a client is the same. And if we can just systemize and process that amount, then you can actually focus more on the differences between the clients.
Sam Penny (07:46)
So then if we look at corporate America, know, corporate America and, you know, big corporations right around the world, it's all about leverage. What is it do you think that founders are completely blind to that haven't had the benefit like you of working inside that big corporation?
Jesse P. Gilmore (08:04)
They have the ability of being able to control the quality of work and train people on the quality of work where the person that does the work can change, but the customer is not impacted. And that ultimately changes the game. The moment that you remove dependence upon an individual, like a single person within an organization, the ability of the organization to kind of adapt and evolve and change and ⁓ grow,
kind of just greatly increases. And that wasn't something that I fully understood until I was in corporate America. And then I was like, ⁓ this kind of makes sense. And then when we started actually working with founders and then removing the dependence upon the founder, was like, holy crap. It like really, really works, especially when ⁓ marketing agencies just go, okay, well, if I have 20 hours per week to work on marketing and I already do it for my clients, but I start doing it for myself, it's like kind of crazy.
Sam Penny (08:49)
Ha ha ha.
Jesse P. Gilmore (09:02)
how much of a change that is. I would say just they don't understand, I think the majority of founders don't understand leverage. And leverage is like an easy way of describing leverage, because that's like my favorite word. actually like trademarks leverage for growth or LFG before LFG became like in style, I guess. leverage is really based around what's called asymmetric return. if you take
Sam Penny (09:21)
Hahaha
Jesse P. Gilmore (09:30)
one hour to create an SOP that saves you 10 hours a week, that is leverage. You're spending one hour, one unit of input to create 10 units of output. The more that a founder focuses on leverage and that asymmetric return type of work, the value of what's being created is better. And I know you're probably going to get me into some practical application at some point.
Here's a real quick one for anybody that's listening to me and Sam right now. Just if you are trying to figure out the best way of creating leverage, if you just look at all the things that you're kind of doing throughout the week and you just create a standard for yourself. So an easy way of doing that is just do a loom video and start talking yourself through the task that you're already doing and then use the transcript and AI to create an SOP. It's like.
So simple, it adds probably 20 % more time to create whatever that loom video is, but then all of sudden you have an asset. That's an example of an asymmetric return type of thing. But I didn't want to go too down a rabbit hole with the assam.
Sam Penny (10:36)
No, look, you know, I work with a lot of founders and ⁓ being able to basically build the value of the valuation of the company. And one of the key things is to remove the founder from the day to day. And an integral part of that is exactly what you described building those SOPs. Why do you think it is that most founders are quite adverse to building something that they know is going to ⁓ buy them freedom, buy them time?
What is it?
Jesse P. Gilmore (11:08)
I think it's the identity. I think it's an identity ⁓ change or shift that needs to happen because if you think about a typical founder, and it could be a agency, it could be just a regular founder, where the founder's skills are what builds the business in the way of getting. They might be good at SEO, they might be good at paid ads, they might be good at whatever, and they start doing it for a period of time and they become like...
the person and the best value that they can give at that period of time is their own time and effort and energy, right? And eventually they start building a team, if they know how to do that. They start building a team and trying to figure out, if I assemble these types of people, am I able to deliver great work? And eventually they get to a place where in order for them to grow past a certain point, they're gonna have to start switching from the doer to a trainer, which is different.
Right? And then from a trainer to a manager, which is also different, like different skills, different mindsets, different ways of actually creating value to the company. And then from a manager to a leader and then a leader to a visionary. And I think that that's the five steps or five stages of a founder getting to a place where eventually as the visionary, you have the whole organization, like people running whole parts of the company so you can focus on growth. And until they kind of go through those changes,
every one of those kind of changes, I guess, or shifts of an identity from doer to trainer is literally just a mindset shift that is letting go of certain parts of the organization and letting go of perfectionism. That's a big one. ⁓ And to embrace like a new part of the value and getting to understand that you're giving more value to the company when you do ascend. So I think that that's really hard for people to wrap their head around sometimes.
Sam Penny (13:01)
this framework, it's fantastic. How often, and you must see it with ⁓ all the clients that you've worked with, ego is the biggest barrier to them stepping into what this framework is.
Jesse P. Gilmore (13:15)
Ego is a funny one. It's the clinging to the identity, right? And so I think that people holding onto an identity, holding onto the ego, not allowing themselves to be vulnerable enough to say, maybe somebody actually can do this work better than I can. That's like a hard thing to embrace sometimes.
Especially with marketing owners or marketing agency owners as well because a lot of what they're doing is they're promoting, you know, and they want to have always like the good face out there. But I've seen I've talked with so many of coached over 500 agencies over the last six years. And a majority of them maybe don't have the business background or don't understand the science of business. And so a lot of them are kind of like winging it, you know, and they get to a certain point where they're like, you know, what do I want to do with it? And I think that
to break the ego, which is probably like your next question, ⁓ but to break the ego, they have to have a stronger why than the resistance that they have staying where they are. And I think that if you're talking with somebody and you're trying to figure out, right now the business is completely dependent upon you and in order for you to sell it, you have to actually like go through the uncomfortable changes that we were talking about, there has to be a very strong why.
And so one of the first things I ask people is like, what's your end game with the business? Are you trying to build it to sell it? Are you trying to build it to scale it to the moon? Or are you trying to work in it whenever you want to? And the interesting thing is, that whether they choose any one of those three or they just want the choice of those three, the pathway is always the same. Remove the founder dependence. You do that and then everything else gives you the option.
Sam Penny (14:59)
Being a founder, being that entrepreneur, it is a 24-7 job. And do you find that many founders, they're stuck in the founder trap where they believe that entrepreneurship is all about working the eight hour, the 80 hour weeks, being on the treadmill. How often do you find ⁓ that they just don't wanna give up freedom?
Jesse P. Gilmore (15:24)
I think the hustle that you're talking about, think it's the reason why they think that that is like the norm is because the people that are the hustle culture are like the best marketers. They're just the loudest in the market. And so when you think about, ⁓ if you're thinking about entrepreneurship, I'll take a step back. In the way beginning of a niche control, was trying to figure out like,
who's our enemy, know, who's our like, we throw rocks at us versus them kind of thing, you know, within marketing. And I realized pretty early when I was looking through Instagram, there was like this, there was this picture and it had like three check boxes right by the first one was like get married. And then second one was have kids. And then the third one was build an empire. And then like that one was checked while the other ones were crossed. And I was like, F that I was like, it's not a life. It's like,
Sam Penny (16:11)
Hahaha.
Ha
Jesse P. Gilmore (16:17)
totally the exact opposite of what I'm trying to create. And I have three young kids, eight years and younger. I have a puppy, I have a wife, and I actually really want the business to be able to fuel and provide ⁓ freedom for me to have the weekends off, take vacations, be able to do those kinds of things. And I think that the hustle culture is just really loud. Everybody follows like Alex Hermosy and...
thinks that that is like the ticket to success. And there's a lot to learn from Alex Hormozi, but it doesn't necessarily mean that his way is the right way or his way is the only way to grow and to be an entrepreneur and create that freedom. I actually, it kind of scares the shit out of me. Just like think about people that will later just wake up and then all they do is work nonstop. And then they're like, screw it. I don't want to have a marriage or a kids. And I'm like, oh, that's just not me.
with just different values, you
Sam Penny (17:17)
It's interesting, know, the big influences that come out of the US. You've got David Goggins, you've got Gary Vee, you've got Alex Hormozi. When you look back at the businesses that you built with your brother ⁓ and you're working 80 hours a week, what were the conversations you're having at that time with your brother?
Jesse P. Gilmore (17:36)
Mm-hmm.
Can we keep on doing this? It was like a for real question, like how long is it gonna take for us to figure out how to make this simpler? Those types of questions had us up a lot at night. And I remember when we were deciding to dissolve it, it was really close to one of my birthdays. It was like 2011. And it was November 2nd. I wrote it in my book. That's how I remember the date.
Sam Penny (17:39)
Yeah
Jesse P. Gilmore (18:05)
And I remember just sitting there and looking at the dissolution, articles of dissolution document. And I was like, where did we go wrong? You know, and it was like these really deep questions of like identity, right? I had built like a whole ego. I was the face of that business too. So I'm like, I'm pretty used to being apparently the face of businesses. But in that one, had it like, we had millions of visitors to our website.
Sam Penny (18:28)
Yeah
Jesse P. Gilmore (18:34)
Like Beyonce retweeted one of our tweets and at that time it was like everybody just flocked like crazy and like, so everybody knew my face and then I'd go to these events and, and, you know, promote the shows and everything. And so for me, it was a really big ego hit, identity shift and kind of looking at how can I rebuild it in a way and how can I rebuild my life in a way that kind of supports me.
⁓ And I thought that I knew what I was doing, but it took a couple more businesses in corporate America and then I finally figured it out. So yeah.
Sam Penny (19:10)
Jesse, you were clearly the man in those moments. Thinking about the 500 clients that you've worked with now, you've got these high performing founders and the problem is often them. How do you handle that moment of telling them the truth that the real bottleneck is gonna be them?
Jesse P. Gilmore (19:27)
Well, I may get a lot easier now because I just put it on my LinkedIn profile tagline. I help agency owners build businesses that don't need them. And that's like that's my like right from the get-go and it wasn't until I started well first up. I've been a trainer or coach or a mentor since I was like really young.
Sam Penny (19:33)
⁓ What's what is that tagline?
Perfect.
Jesse P. Gilmore (19:54)
Like I took on a lot of those types of roles, even in my teens and like leading groups and stuff like that. So it's pretty easy for me to understand how training works and how to like talk to people in a way that gets them to embrace whatever I'm about to say, as opposed to, you know, coming across too strong or whatever. So one of the easiest ways is just getting to understand kind of like where they are, like what's their current state, what problems is happening within their business. And then
being able to label that and it boils down to the three main things, non-scalable business, inconsistent lead flow in clients or micromanaging a team. And those are three main big problems that if I can identify those, then I can identify the root causes of those. But once I get them to understand that I have been there, I've experienced it before, whether it's the burnout side or if it's just like inconsistency within the business or having to look over people's shoulder all the time.
Once we identify what that issue is, then we start talking a lot more about their desired state. So like, let's just say you didn't have to have that issue anymore. Like, what would you want the business to be like? Like, can you envision it? And if they can envision it, we now have two different states of being, right? We have a current state and a desired future. And once we understand that, that if we have a very strong why, it makes it lot easier to go, okay, what you're doing right now is actually just...
perpetuating this cycle and until we do X, Y and Z, that's gonna, you're gonna just stay there. You do you want to stay there or do you not want to stay there? Okay. Are you willing to do the uncomfortable stuff? Okay. Now, and then here's step by one, step two, step three. And one of the best ways of being able to do it is actually just getting a, a ⁓ log of their time. So Sam, if I was working with you, the first thing I would do as a one-on-one, ⁓ like assignment is I'd be like, all right, for the next week,
You're just going to log your time for seven days every half an hour, both personal and professional. And if you want bonus points include like the energy that you feel. Is it draining or is it uplifting based around whatever you're doing? That one single seven day thing basically maps out what we're going to be working on because we can look at eliminate, automate, delegate time block. We can look at systemizing. We can do a bunch of different things from the use of time and pretty early I can find out.
some key kind of levers to be able to start moving them in that direction where they actually feel different. And once they feel different, they start feeling the freedom, it becomes a lot easier for them to make bigger changes.
Sam Penny (22:30)
Let's talk about this freedom because you say that time freedom has to happen before financial freedom. And that really does run counter to the whole hustle culture that we have as entrepreneurs. Explain why chasing revenue, first, it really does lock someone into permanent complexity.
Jesse P. Gilmore (22:50)
I can tell you've done your research, ⁓ Time freedom always comes before financial. And here's why. When you think about financial, ⁓ if you were constantly on a hunt for, if I make enough money, then I can eventually have the time to pay somebody else to do whatever. And then I can become the person that sits on a beach or.
Sam Penny (22:55)
Hahaha!
Jesse P. Gilmore (23:18)
whatever their desire is on the hustle culture side. What happens is that they make these choices of sacrifice, ⁓ where they just sacrifice too much time, they're not spending with their wife, they're not spending with their kids, they're dedicating so much, and what ends up happening when you start working 68-hour weeks is you're not utilizing the law of diminishing returns.
So not every hour that you put towards something means that you're getting the same level of output based around it. so once you start to realize that the best thing that a founder can do is start to have time to work on the business, or they're separated away from the business and being able to kind of direct where that business is going to go. Once we start freeing up time, everything changes.
And one of the easiest things you can do is if you don't have a start and an end time for your work, just implement it. Start at nine and end at five. Like even if you just had that, it immediately changes what you do in that time. Without some type of boundary, you don't have prioritization. Everything kind of just comes at you and then you focus more on what's urgent as opposed to what's more important. And time freedom, once you start putting boundaries on it,
you start to think differently and you prioritize differently. You empower the team differently because you start understanding constraints. That time freedom allows you to basically have the priorities in the right order so that when you start to focus on the most important thing for your business, which actually is sustainability, then you can play the longer game, which allows you to focus more on things with exponential demand and the rest of the leverage or growth method.
Sam Penny (25:08)
So then that founder who's stuck on that real hustle treadmill, what breaks first? Is it their energy? Is it the culture of the business? Is it the client experience? What is it that breaks first?
Jesse P. Gilmore (25:18)
⁓ I think everybody experiences it differently because each client is going to be a little bit different. Some of them experience burnout, ⁓ which that's usually like when you have a really, really, really small team. ⁓ People would associate with burnout where if you have a larger team or like 500 K per year to 5 million or so, they would just say that they're the bottleneck. ⁓ But regardless, there is a certain
where they start realizing that the use of time is not being allocated according to what's valuable. ⁓ Or they have some type of life event that kind of shapes them and shakes them up and goes, all right, you need to do something a little bit different. ⁓ So, and then other times it's based around just the quality of the work that starts to suffer. So it could be like a defect or something from the client. It kind of happens from a lot of different angles, ⁓ but regardless, there's always kind of like, this is the root cause.
It's the founder.
Sam Penny (26:19)
Yeah, right. Let's get a little bit practical. The EADT audit, eliminate, automate, delegate, time blocking. If someone listening today, they're doing $20,000 a month, but they're really drowning in, you know, might be Slack notifications, client fires. What's the first ruthless thing that you always get your clients to do and what should they start doing this week?
Jesse P. Gilmore (26:42)
Absolutely. So if you haven't done a time log before, I would say do it. For many people, it's like pulling teeth, but it just gives you raw data. it's the same thing as if you're taking over a marketing campaign, you'd want to look at past campaigns before you do something new, right? And when you look at your time, the first thing you want to do is you want to look at all the things that you do. Is there something that you're doing right now that you could eliminate? Okay. If you got rid of it, would you still have the same kind of out?
outcome. ⁓ Steven Covey created like the time management matrix, which is kind of like a quad based around important and urgent, not important, ⁓ or not important, important, not urgent, urgent. And if you just focus on elimination, you're eliminating what's called quad three and quad four time. And then if you can't eliminate it, can you automate it? ⁓ Data transfers are pretty simple. So if you're doing anything where you're copying data over,
You can pretty much automate that, especially these days. ⁓ And then if you can't eliminate, automate, can you delegate it? Now, Dan Martel talks about the buyback period of finding somebody that can basically do some of those tasks for about a fourth of what you pay yourself. That's a good kind of model to be able to use for delegation. So if you're a solo person, could you find somebody that would be able to handle your inbox or those Slack notifications and be able to prioritize those for you?
And then lastly, that time blocking has a lot more to do with condensing similar types of work together. So if it's a technical stuff, bunch those together. If it's a sales stuff or being on a podcast with Sam, know, bunch those together. That gives you less ⁓ decision fatigue, which allows you to feel better about the work. That's what I would suggest for that. The automation part is really, really key. And if you're trying to like,
figure out the best way of handling a lot of notifications. Just time block, time for 15 minutes in the morning, right after lunch, and then right before the end of the day, just to focus on those notifications. In between times, go into your deep order.
Sam Penny (28:55)
Yeah, absolutely love it. What's the, you must see it across all the founders that you work with. There's tasks that they think that only they can do, but they, you know, from your perspective, they really shouldn't be doing it. What do you see most founders doing those tasks that you just go, no, that's bullshit. You need to stop doing that straight away.
Jesse P. Gilmore (29:17)
One of the biggest unlocks that I had was hiring an executive assistant that helps with my inbox and calendar. And I think that that was a big, big one as we continue to impact more people and set up systems to help tens of thousands of founders. I knew that raw inputs were going to be the thing very similar to what you're talking about with the Slack notifications. I knew that was going to be the thing that was going to throw me off from whatever I was focused on. So.
Hiring Leo was one of the greatest things that happened last year. And ⁓ I would highly suggest that if you're starting to increase the demand, having somebody be able to help you kind of do that initial filter is huge. I would not rely solely on AI, even though AI could probably do this. ⁓ It's way more important to actually have a human that you can talk to because...
I think that we all are human and we want to experience humans even in the midst of everything. ⁓ But that was huge. That was a big unlock. And I would actually suggest most founders shouldn't take in so many raw inputs. They need to be organized and kind of like, all right, here's the things that you need to focus on. Here's a couple of decisions that need to be happening. These are the things I took care of and the other ones I just eliminated. And that's so helpful, by the way.
Sam Penny (30:40)
Now, one of the things that you've said is that the business can't outgrow the leader. Let's talk about niching control because what's the most uncomfortable upgrade that you personally have had to make to scale? Is it hiring? Is it letting go, raising prices, is trust? What has really nearly broken you through this whole process of building niching control?
Jesse P. Gilmore (31:02)
I've had so many times where it almost broke me. I wrote a lot about those in the book. Yeah, think so to answer your question, I'll say two main ones. So in 2023, I was going through a switch, 2022, was switching from one-on-one to a group model so I could impact more people.
Sam Penny (31:06)
Hahaha ⁓
Jesse P. Gilmore (31:28)
And then in like January of 2023, I launched the Leverage for Growth podcast and then started writing the agency owner's guide to freedom. And at the same exact time, I was investing so much into those assets because I knew they were going to be long-term help. I ended up losing 60K in about a three month period of time, which kind of like didn't really help with the cash on hand kind of thing. At the same exact...
Sam Penny (31:54)
That hurts.
Jesse P. Gilmore (31:55)
Yeah, at the same exact time as my third child was being born in June and I had to really lean into faith and trust because I was kind of being shaken up a little bit with that one. And for that, was actually like part of the identity switch was like I actually am an authority, I am somebody of value, and I am able to make it through a really rough storm. ⁓ And I think 2023 taught me a lot.
Now, more recently, ⁓ so about a year ago, ⁓ in a week or so, my dad passed away. And when that happened, it kind of shook me up a little bit. And I started to realize that I didn't have forever, you know, time is finite on this earth. And I had to make some changes and I did some deep dive into myself and figuring out kind of what do need to do for the business. And I started to focus a lot more on legacy.
So the business itself had a lot of systems. There's a lot of people kind of helping us, but ⁓ I had not gotten out of the driver's seat as much and I had not applied leverage for growth, especially the empowering your people part to my own business. And so a lot of Q4 in this last 2025 was geared towards understanding what the vision is when I'm not the person kind of doing the QA checks and not doing all those kinds of things. What does the business look like?
And I made a very distinct identity shift in between Christmas and when I got back in January. And I started to label what my identity was in 2025 as the visionary builder, where I was like the person that would like envision something. And then I was also a system person. So then I jumped into systems and started building it. And I started realizing that that was like holding me back. And in 2026, I made it kind of like a
a company-wide announcement, which is super funny because we have a very small team. But I did it and it was funny because I labeled it. was like, the Jesse version of me before was the visionary builder and now the 2026 version is a steady operator. And then I was like, then control before in 2025 was like operating like a startup. And in 2026, we're operating like an established business.
Sam Penny (33:57)
Hehehehehe
Jesse P. Gilmore (34:18)
And over the last six weeks from this recording, so we're recording on February 18th, ⁓ in the last six weeks, I've hired five agencies to help us with different parts of marketing that we are getting rebranded. So we're going to have a new logo maybe by the time that this rolls out. And we'll have multiple people that are specialists in certain things being able to run. So then I stay in my lane as a coach and a closer, right?
And then my brother who also works in initial control as the operations, he's now in the backend. And so he gets to stay in his lane. I'm staying in my lane. And then we got a bunch of marketers staying in their lane. And I think that that requires a lot of letting go of things that I've been doing for years. And even with Jeremy, because he took all the stuff that I didn't want to do. And then now I'm like, all right, Jeremy, now you stay in this lane. And he's like, ah, and it's like, it's hard for him to do that. But
Sam Penny (35:13)
Ha ha ha.
Jesse P. Gilmore (35:14)
We're all doing
it, you know, and it's pretty cool. Tomorrow we're actually aligning the entire marketing team and giving specific roles and ⁓ Sherry is the brand manager and then like, you know, it's a start mapping each one of these things out. And I am so excited to just stay in my lane. Like I've never been more excited about like the future of the business and like what's happening because I'm starting to finally like.
Sam Penny (35:35)
Ha ha!
Jesse P. Gilmore (35:40)
do what I've been teaching my clients to do and I know how impactful that actually is. So I'm like, I'm just ready to start impacting a million entrepreneurs. And I'm like on this really intense mission to do that. And it's all being assembled literally as we speak. Like tomorrow is the monthly sync with ⁓ the marketing team. So very excited.
Sam Penny (35:59)
Man, I can see how excited you are about this. Now, obviously this is, you're gonna lean very heavy on your SOPs, but for many founders who are building a culture and that's really ⁓ what we're always trying to do, build the culture. They often feel that putting in SOPs is gonna make the company more sterile. When you speak to these founders, have you ever said to them that your chaos
is not creativity, it's just avoidance.
Jesse P. Gilmore (36:29)
Ooh, I haven't used those exact words, but I probably should. ⁓ Yeah, it's really interesting. The times where people kind of fight me with the idea that standards and systems actually increase creativity, I actually just share with them Susan Fernandez case study where she was a full service creative agency. gave me, like we met and she was like.
Sam Penny (36:33)
Take it.
Jesse P. Gilmore (36:58)
I've tried everything out there and if I've tried for too many years, very similar to what I had with my first company and she's like, if I don't, if I can't grow this business or scale this business in the next six months, I'm going to shut it down. And, and I had a teacher different ways of looking at systems as not something that's like holding her back or making the business worse, but actually making it better. And, you know, spoiler, she did not shut down her business. She
doubled in six months and then got acquired in 18. And she got two case studies, one of them right after she doubled and then another one right after she got acquired. And she talked about how ⁓ she originally thought that ⁓ implementing SOPs and systems were actually going to make the team not like it as much. But the feedback from the team was amazing. The feedback of the team was like, I don't have to spend so much time and energy towards trying to figure out like how this thing is going to work.
⁓ And I can kind of just plug in and it's more of like you become kind of like teammates and where everything everybody is playing from the same playbook and it kind of just changes the culture. So ⁓ I think it's more so how the leader or the founder communicates what systems are. Because like without systems you don't have career building or career developments. You don't have succession planning. You don't have the ability of people that are specialists to become leaders. Like there's no like actual. ⁓
growth within a company without systems. And so I think once people start to understand that, they should be able to start embracing it. And the moment the founder does, it's all about communication. How do you communicate the systems? And last but not least, system building should never come from the top down. So that's like really, really important. So it should never come from the top down. What I mean by that is you don't have managers making SOPs for specialists to do.
You have specialists that like work together to form whatever the thing is and then add the manager in there just to make sure it's it's a you know up to up to speed so. Yeah, I mean I could go for a long time on that, but yeah, does that make sense? ⁓
Sam Penny (39:02)
Love it. ⁓
Often as entrepreneurs, we're chasing the revenue. I saw one of your clients within 12 months went from 15,000 a month to 100,000 a month. ⁓ But when we're chasing revenue, ⁓ we're losing what the ultimate mission is of the business. When we chase revenue, what is it that really fractures first inside a business?
Jesse P. Gilmore (39:27)
I will you talk about culture and I think that chasing revenue for revenue sake it affects the culture and affects the way that people look at things and they if if revenue is the main kind of like North Star metric then you that if that actually is the thing then people start looking at clients as numbers and it like it changes like pretty much everything so I would I would and even with Warren so you're talking about Warren going from fifteen thousand to a hundred thousand nine months.
And with Warren, one of the biggest kind of unlocks was actually not focusing on revenue. We actually didn't even like, that was like a secondary thing. The first thing we did was client case studies. And all we did was just get everybody to agree that what we're trying to do is we're trying to create a quality experience for the client and that they would have such a great experience that they would give a case study. either it's a written one or some kind of video.
And once that happens, then the culture immediately goes from money to quality, right? And then from there, we started looking at different things like profits and so forth. But the biggest mental model that switched was when I told Warren, said, what if your business was wanting to grow as fast as you were to allow it? And your main role as the founder is just to keep on removing whatever is holding it back from growing at an expansive rate. And it ⁓ that
mindset shift got him to think about the offer, the systems, the people, and we eventually figured out that the bottleneck was more based around training people than it was based around demand. And so then we had to figure out how can we shorten the amount of time it takes for a new hire to become independent within the work. And that's when there was kind of like this hockey stick thing that started happening. And by the way, now he has a 25 person team.
Sam Penny (41:15)
Wow, man, what a great outcome. He must be loving you.
Jesse P. Gilmore (41:22)
And I love him too, he's one of my favorite case studies to talk about.
Sam Penny (41:27)
Absolutely fantastic. Now let's shift gears. Let's talk about the listener, the person tuning in who wants to learn from Jesse Gilmore. ⁓ I've got four questions for you. Quick answers. What's the most common lie agency owners tell themselves to justify their 80 hour work weeks?
Jesse P. Gilmore (41:44)
Mmm, that it has to be that way. Like that that this is only going to be a season and eventually it'll get better without doing anything different.
Sam Penny (41:54)
Do you see behaviors ⁓ that really immediately tell you that a founder is not going to be able to scale past six figures?
Jesse P. Gilmore (42:02)
If they continue to stay in a cycle where they choose comfort over uncomfort or comfort over doing something that is uncomfortable for them to grow. If they can't learn the skills that are needed, like being ruthless about a vision and bringing it into reality or declaring it to people and then moving on it, ⁓ then they're gonna continue to stay kind of like as a centralized business model or a centralized, ⁓ like they are the main.
Yeah, like the dependence upon the business and the founder is all funneling through them if they're not able to embrace something that's new or change the way that they go about things.
Sam Penny (42:44)
Jesse, is there a metric that you see that most founders really ignore, but really does determine whether they're going to survive over the next five years?
Jesse P. Gilmore (42:54)
Metric. I was gonna say client case studies. It's like my it's like legitimately my favorite thing because if you think about client case studies, if you if you had client case studies as a North Star metric North Star is like your definition of success as an organization. The only way that you're going to get ⁓ enough client case studies is by bringing a new business having clients that are satisfied and then delivering on what you served right? So I would say.
Sam Penny (42:58)
Hahaha.
Jesse P. Gilmore (43:23)
Being able to track that and make that as like your KPI or your North Star metric would fundamentally change everything and no one really tracks that. They're always focused around revenue. And in actuality, the way that revenue works is it's a lagging indicator. It's very similar to the client case studies. It's made up of a lot of things and then eventually you get to some things that you can focus on that influence the predictability of actually hitting it. And I think...
client satisfaction and the ability of just asking, you know, if we hit your goal, would you give us a case study? And they say yes, and then you just sprint towards hitting the goal. ⁓ I think that would fundamentally change everything and it's usually the thing that people are missing.
Sam Penny (44:05)
That's a pretty good metric. ⁓ Now, if someone wants to build a million dollar plus agency, what do you think they should really emotionally detach from right now?
Jesse P. Gilmore (44:19)
Right now these are supposed to be quick answers Sam. I got you. You got it. You got it attached from perfectionism and embrace the idea that with the right processes and systems, ⁓ someone else who it does not get paid as much as you do can do the same same quality of work or better than you can. And if you embraced.
Sam Penny (44:24)
Yeah!
Jesse P. Gilmore (44:45)
letting go of perfectionism and finding those people and setting them up for success, you'd have a fundamentally different business.
Sam Penny (44:51)
Yeah.
Jesse, you said that ⁓ you want to impact a million entrepreneurs. When you hit that number, what does the standard entrepreneur look like? Are they calm? Are they structured? Are they present with their family? What is that? Paint that picture.
Jesse P. Gilmore (45:06)
I believe that the impact of the entrepreneur comes down to what's their definition of success. So the culture, the hustle culture has a definition of success they want you to subscribe to. Whether that's growth or revenue or $10 million business or selling or whatever it is, I want everybody that's listening right here to just ask themselves, what is your actual definition of success if everything else external was let go?
What is the definition of success? For a majority of people that resonate with my message, like if you're listening to the end of me and Sam's talk, most likely you're resonating with something that's happening right now. ⁓ Then most likely you're the type of person that wants to work a certain amount of hours, wants to have a time freedom, wants to be able to take vacations and have the business be able to run without you constantly there all the time. And you also most likely just want like the ability of
having some type of impact on people, right? That's the reason why entrepreneurs are even in business as freedom and impact, right? And I think that the impact of the million entrepreneurs is a pathway there, clarity, calm, and then they're plugging into leverage for growth as a method, kind of like as a beacon. If you think about, let's dark out, and you're trying to get to...
You're trying to get to the lighthouse and then the lighthouse goes ping and they're like, alright, I'm going to go towards that. Like that's the way that I want to have that impact on.
Sam Penny (46:40)
Fantastic. Now, before we wrap up, ⁓ for those founders who feel like they've basically just built a bigger cage, where should they start?
Jesse P. Gilmore (46:50)
Time log. Yeah, just do the time log. Yeah, it's ⁓ it's it's really easy, but just do the time log and then go through what we like rewind ⁓ this ⁓ episode and then look at the eliminate automate delegate time block. If you just literally did that week over week for about four weeks, you would fundamentally be operating completely different than what you are right now, ⁓ and it would give you an insight into all the next moves that you need to make.
Sam Penny (46:52)
Timelog.
So when we get to the end of this episode in one minute, Jesse, that's the number one thing that they're going to have to go away and start doing.
Jesse P. Gilmore (47:27)
Yeah, time log. If you get it done and find me on LinkedIn and then let me know that you listen to me and Sam and that you did your time log or you can even ask for a template for a time log and I'll give it to you. ⁓ Because I think it's single most important thing that you can do right now is just analyze your time. Be real with it and get aware of what needs to change and then start making those changes.
Sam Penny (47:41)
fantastic.
If you're listening to this and you felt slightly uncomfortable, then that's a good thing because somewhere in this conversation, you probably recognize yourself. It's the late nights. It's the constant slack pings.
The quiet belief that if you step away for a week, everything might wobble. That's not ownership. That right there is dependency. Jesse has shown us that real leverage isn't about squeezing more productivity out of your calendar. It's about designing a business that can breathe without you. A business with architecture, with structure, with intention. For the founders listening who recognize themselves in this conversation, who know they've been the bottleneck, who ready to stop being the engine and start being the architect.
Jesse, where's the best place for them to connect with you?
Jesse P. Gilmore (48:34)
Absolutely, so if you're on LinkedIn, you can find me Jesse P. Gilmore and the P actually helps with SEO and a bunch of other things. So if you type that into Google, you'll find a bunch of stuff. But if you connect with me on LinkedIn, just let me know that you listen to me and Sam and maybe you want the time log. Happy to send that over to you. And when it comes to if you're a marketing agency owner and you're you're looking for kind of like that pathway we talked about, you can go to nicheincontrol.com.
And if you want a free copy of my book, The Agency Owner's Guide to Freedom, you can go to nicheincontrol.com/book, and I'll give the links to Sam to put in the show notes, but that would be a good way to start.
Sam Penny (49:16)
Absolutely fantastic. And let's not forget the leverage for growth podcast that you run.
Jesse P. Gilmore (49:20)
Yeah, I have over 200 episodes of Leverage for Growth podcast and actually that 2023 version I was doing daily leverage episodes which were like five to ten minute episodes of me while I was learning during that process of time so kind of cool but the last 70 or so episodes have been actual interviews with successful agency owners and kind of reverse engineering what worked for them so Leverage for Growth podcast is found on Apple or Spotify or YouTube.
Sam Penny (49:49)
Fantastic, and I'll make sure I put all those ⁓ links into the show notes. And if this episode made you rethink how you're building, share it with another founder who's still stuck in the engine room. This is Built Built To Buy. I'm Sam Penny. Go build something that works, even when you don't.
