Scaling Your Agency for Exponential Growth With Jesse Gilmore

Jesse Gilmore is the President and CEO of Niche In Control, an agency helping overwhelmed agency owners simplify operations, develop their teams, and rapidly scale without sacrificing their lives. With a rich background in various businesses and extensive experience in corporate HR and systems, he brings a unique perspective to the agency landscape. He’s the author of “The Agency Owners Guide to Freedom,” which provides agency owners with strategies to escape the time for money exchange. Jesse also hosts the “Leverage for Growth” podcast and has created a popular digital newsletter for agency CEOs.

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Here’s a Glimpse of What You’ll Hear:

  • [0:00] Jesse Gilmore shares the formula for scaling your agency 
  • [3:30] How to harness natural traits like adaptability and multitasking in business
  • [4:02] Uncovering the impact of financial stability and freedom on entrepreneurial drive
  • [6:48] The value of corporate experience in refining business systems and HR skills
  • [8:18] How humility and a learning mindset can lead to valuable corporate opportunities
  • [14:12] Does time freedom often precedes financial freedom in the entrepreneurial journey?
  • [19:30] Insight into the 12-week-year principle for maintaining work-life balance
  • [22:59] How a strategic focus on systems and processes can lead to significant agency growth
  • [26:38] The importance of identifying and addressing bottlenecks in your agency business

In this episode…

Have you ever wondered what it takes to scale an agency’s business effectively? The journey from startup to growth involves mastering the right mindset, systems, and team dynamics. But how exactly does one navigate the complexities of expansion while ensuring sustainability and avoiding the common pitfalls of overworking and underplanning?

Jesse Gilmore addresses these challenges by emphasizing the importance of systems, proper time management, and strategic simplification. He shares his journey of transitioning from a hands-on agency owner to a strategic leader who empowers his team and implements robust systems to enhance efficiency. Jesse highlights the transformative approach of taking regular breaks to reassess business strategies and ensure that the company’s growth is sustainable. He emphasizes the importance of drawing lessons from diverse experiences to refine business acumen and the capacity to adapt and deploy effective strategies for growth and sustainability.

Tune in to this episode of the Smart Business Revolution Podcast as John Corcoran interviews Jesse Gilmore, President and CEO of Niche In Control, about his strategies for scaling and sustaining growth in marketing agencies. They delve into the significance of learning from previous business failures, how to balance personal relationships with entrepreneurial pursuits, and how to identify and address bottlenecks in your agency business.

Resources Mentioned In This Episode

Quotable Moments:

  • “Entrepreneurship is one big marathon, and if you can understand that you’re doing these sprints, it gives you enough time to rethink strategies.”
  • “The business is wanting to expand as fast as humanly possible, and your role is to remove whatever is holding it back from growth.”
  • “Time freedom happens before financial freedom. If you can create a business and a life by design, it changes everything about how you work and live.”

Sponsor: Rise25

At Rise25, we’re committed to helping you connect with your Dream 100 referral partners, clients, and strategic partners through our done-for-you podcast solution. 

We’re a professional podcast production agency that makes creating a podcast effortless. Since 2009, our proven system has helped thousands of B2B businesses build strong relationships with referral partners, clients, and audiences without doing the hard work.

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The Rise25 podcasting solution is designed to help you build a profitable podcast. This requires a specific strategy, and we’ve got that down pat. We focus on making sure you have a direct path to ROI, which is the most important component. Plus, our podcast production company takes any heavy lifting of production and distribution off your plate.

We make distribution easy

We’ll distribute each episode across more than 11 unique channels, including iTunes, Spotify, and Google Podcasts. We’ll also create copy for each episode and promote your show across social media.

Cofounders Dr. Jeremy Weisz and John Corcoran credit podcasting as being the best thing they have ever done for their businesses. Podcasting connected them with the founders/CEOs of P90xAtariEinstein BagelsMattelRx BarsYPO, EO, Lending Tree, Freshdesk,  and many more.  

The relationships you form through podcasting run deep. Jeremy and John became business partners through podcasting. They have even gone on family vacations and attended weddings of guests who have been on the podcast.

Podcast production has a lot of moving parts and is a big commitment on our end; we only want to work with people who are committed to their business and to cultivating amazing relationships.

Are you considering launching a podcast to acquire partnerships, clients, and referrals? Would you like to work with a podcast agency that wants you to win? 

Contact us now at [email protected] or book a call at

Rise25 Cofounders, Dr. Jeremy Weisz and John Corcoran, have been podcasting and advising about podcasting since 2008.

Episode Transcript

John Corcoran 0:00

Today we’re talking about how to scale your agency business, including having the right mindset, the right systems and the right people in place. My guest today is Jesse Gilmore. I’ll tell you more about him in a second. So stay tuned.

Intro 0:14

Welcome to the Smart Business Revolution Podcast where we feature top entrepreneurs, business leaders and thought leaders and ask them how they built key relationships to get where they are today. Now, let’s get started with the show.

John Corcoran 0:31

Alright, welcome everyone. John Corcoran. Here I am the host of this show and you know, because you’ve heard previous episodes that I’ve every week I talked to smart CEOs, founders and entrepreneurs from all kinds of different companies. We’ve had Netflix and Kinkos. What do you do at Activision? Blizzard LendingTree GrubHub. Activision Blizzard. I said them already. Redfin OpenTable, all kinds of great episodes in the archives, go check them out. And this episode brought to you by Rise25, where we help b2b businesses get clients referrals and strategic partnerships with done-for-you podcast and content marketing and you can learn more about what we do over at or email us at support at Alright, first shout out to Corey Quinn, past guest on my podcast, great guest agency advisor and go check out that episode. But he introduced me to today’s guests. Some of my best guests come from recommendations from other past guests on the show. 

And my guest today is Jesse Gilmore. He’s the President and CEO of Niche In Control. It’s an agency dedicated to empowering marketing agency owners on their path to exponential growth and sustainability. And he has a lot of different experience in different types of businesses, which kind of distinguishes them in the agency expertise realm. So we’re gonna get into that. And he’s also the author of a book called The agency owners guide to freedom which is a comprehensive guidebook for overwhelmed agency owners there it is seeking to break free from the shackles of the time for money exchange, and I spent a lot of years doing time for money, none the NGO world interestingly, but when I was practicing law, and it’s a tough world to be, and he’s also the creator of new agency, CEO newsletter, digital newsletter, which you can sign up for at his website. And it also has a great podcast called leverage for growth, which you’ll have to check out as well. 

And Jesse, such a pleasure to have you here today. And I was chatting beforehand, about, I love to ask people about how they were as a kid, and he could a little side hustles that they had as a kid. And you must be a certification guy, because you at a young age realize that if you go get certified as a babysitter certified babysitter, maybe it was, you know, some kind of EMS certification or something like that, that you could charge more and went on babysit, and you’ve found the right family. Tell us about it.

Jesse Gilmore 2:46

Yeah, back when I was younger? And to answer your question of, you know, I was entrepreneurial from the beginning, I really wanted to make a lot of money. And so when I was 13, I found out I did my research and figured out if you get certified in things like infant CPR and other like first aid kind of things, you’re marketable a bit better. And so I was able to get $5 per kid per hour, and then just found a family of five.

John Corcoran 3:16

I have four kids, and I have struggled to watch my kids solo without my wife around. So I can’t imagine being 1314 years old and watching five kids, how’d you do it?

Jesse Gilmore 3:30

Yeah, I think my natural ADHD and hyperactive disorder was kind of channeled in there and being able to figure out how to multitask and prioritize. There must have been something that happened really early.

John Corcoran 3:42

And what drove you said, you’re really motivated, make a lot of money. And a lot of times I find people fall into a couple of different buckets, either something they can’t even quite put their finger on. They just wanted money. Or sometimes they grew up in an entrepreneurial family. Sometimes they didn’t have money, their family didn’t have money. What was it that motivated you? 

Jesse Gilmore 4:02

Yeah, That’s a good question. Um, I think when I was growing up, I was the youngest of three. And my dad was a doctor who worked 90 to 100 hours per week and got to a point where he was bringing home tons of money. But then he got so burnt out, it ended up becoming like a health issue thing. And so he ended up having to shut down the business and deal with a lot of health stuff. So at the time when I was kind of growing up, thinking back to it, we came into a lot of money, and then all of a sudden we had none. And I think that that fluctuation got to a point where I realized, you know, financial stability is a really big thing. Financial freedom. Making money is a big thing. And I think I was just naturally trying to figure it out right from the get go.

John Corcoran 4:52

It’s kind of a real cautionary tale, then of the perils of working too hard, which I met. Can you bring to your work working with agency owners who oftentimes do the same thing work, work themselves to death?

Jesse Gilmore 5:09

Yeah, and actually, interestingly, if you follow the entrepreneurial journey, that is actually what happened in my first business, second business, my third business and actually, my first business was called the North Coast collective as a web Information Services business, promoting the arts and culture of Minnesota. And kind of similar to digital marketing, we were selling ads on our own website and stuff. And we had built a business so centralized around us. And it took us a really long time to get a proof of concept. So I had the idea for a long time, we’re working through a lot of processes to figure it out. And I got to a point where, once the business was gaining traction, I started realizing that as we became more successful, I just kept on working longer hours. 

And I couldn’t figure out how to break that. And so for a long time, I was working 60-80 hour weeks, basically repeating what happened with my dad. And I got to a point where actually me and my brother decided, like, look, we got to shut this thing down, something’s wrong, something’s off. And I didn’t really know what it was. Systems. I didn’t know what it was. And then I went into my second business, the same thing happened. When the third one, the same thing happened. And it wasn’t until I just kind of sucked up my ego, went into corporate America to learn business systems, and HR, which I probably talked a little bit about, and then realizing that those were the things that were missing. So yeah, it’s been a big, I guess, focal point or focus of mine.

John Corcoran 6:48

I figured, it is interesting that you managed to go into corporate America, so many people, especially someone like us started three different businesses, you know, so you’re a serial entrepreneur at that point. Lot of times people find themselves unemployable. When you went into corporate America, why do you think that you managed to, you know, handle it, when so many entrepreneurs just can’t handle that going from running your own show to being an employee?

Jesse Gilmore 7:19

Yeah, I think I’m pretty early, I had a really good mentor. Number one, but the second half, I had tried the employee route 28 jobs. So I’ve gone through so many different types of titles and positions. And there’s, there’s a couple of different things with that, that kind of got to me to understand, what are my strengths? What are, what do I bring to the table? What are my competencies, but going into corporate America, I remember. I remember the hiring process, Judy, who I gotta give kudos to by Judy is a VP of HR, and a $4 billion dollar global corporation. And I basically sucked up my ego and was trying to work under her as an intern. 

John Corcoran 8:09

And as really having three separate businesses, you took a step back and said, I’m going to be an intern.

Jesse Gilmore 8:18

I think that at the core of everything, I think internally, I know that I am a continual learner. And there was something that was missing that I couldn’t get from business school, which I went to, I couldn’t get from owning a business. And even before Northwest collective, I was a door to door sales person. And I used to knock on doors, you know, anywhere from 80 to 120 per day. And being the student of life that I am, I asked every single business owner that I got to sit down with, what’s the ticket to a successful business, I wrote it down took, like 1880 Page journals of notes, I brought all of that into my companies, I still realize that it was something I was missing. 

The thing that I was missing was how corporations use business systems to make it to where it’s not single, there’s no single point of failure, where it’s a single person that can do the work. And if that person’s gone, and you know, the customer gets impacted. Once I started realizing that I was learning the thing that was missing. That’s when I realized, okay, there’s something there and I’ll stick it out. 

John Corcoran 9:30

How did you know that when you went into the corporate world, that you would find what you were looking for, and that you know, you wouldn’t end up you know, in a role that didn’t get you what you needed.

Jesse Gilmore 9:44

I think let’s give some context of that time period because I had just shut down the third business and at the same exact year of that business, kind of dissolving. I was getting connected with my now wife. And at that time, we started realizing that and we were living in Minnesota at the time. Yeah, we started realizing that we needed something different. And we already wanted to separate ourselves from the past life, right? The life that was in Minnesota with the three businesses and everything else that was happening, but back then. 

And so prior to corporate America, we moved from Minnesota to Oregon, shut everything down and basically started from scratch. Now, if you’ve ever done that kind of thing, like burning bridges and moving, you know, you are literally starting from scratch. And every network that I had, based on previous businesses, were all in Minnesota, as opposed to Oregon. And so at that place that we had moved, which was Corvallis because she wanted to go back to get her MBA at LSU. And at that time, we realized that that place did not have a really good job market. So I had applied to 42 different jobs, I did a lot of different things to try to make it work. 

And so and then I was like, okay, if I’m gonna start a business it is still going to be a long time before it’s going to gain traction, so forth. And so even though I was doing things on the side, like photography, and whatever, I ended up, yeah, really just getting to a point where he, you got to do something, you know, something.

John Corcoran 11:23

And you were probably one or two kids at this point, when you made this change. 

Jesse Gilmore 11:28

We were planning on actually getting married. And my wife comes from more of the non entrepreneurial type of family, more based around security, and so forth. And so I think part of it, if I’m looking back on who I was back then, is very different now. If I was to look back on it, I think I was trying to figure out how to create that stability and how to create that security. So that way I can, you know, the woman of my dreams.

John Corcoran 11:56

It’s an interesting, you know, conversation around what stability really is. There are many entrepreneurs I’ve interviewed who will argue forcefully that entrepreneurship is more stability, because it’s not like in a job where you can wake up in the morning, come into your company, and there can be a layoff or your boss can just decide they don’t like the shoes that you’re wearing and let you go. Verses when you’re got a company, you’ve got many different bosses, and you kind of diversify your risk in that sense.