[Top Agency Series] Get Your Business To Work for You With Ryan Redding

Ryan Redding is the Founder of Eightfold Advantage, a firm that helps business owners and leadership teams scale without chaos. He previously founded Levergy, a digital marketing agency for home service companies that was acquired by KickCharge Creative in February 2025. A certified Bloom Growth coach and host of the Blue Collar.CEO podcast, Ryan draws from his own journey of overcoming burnout and leading successful company exits to help others build sustainable businesses and achieve their goals.

Here’s a glimpse of what you’ll learn:

• [6:04] Ryan Redding explains the reason entrepreneurs hit plateaus and burnout
• [11:40] The pivotal moment that forced Ryan to finally let go
• [15:21] Why grinding harder won’t create freedom, and the shift founders must make
• [18:04] Ryan’s blueprint for escaping endless work and reclaiming life
• [21:29] How finding the right integrator can change everything
• [27:59] The power of healthy debate in business partnerships
• [36:07] Why most mergers fail and how to avoid disaster
• [44:37] The hidden pitfalls and importance of cultural due diligence
• [52:55] Why Ryan became a certified Bloom Growth coach

In this episode…

Entrepreneurs can easily get trapped in 60- to 90-hour workweeks — juggling clients, managing teams, and putting out constant fires. Profits shrink, growth stalls, and personal freedom disappears. Is it possible to escape the grind without losing control of the business?

Growth coach and advisor Ryan Redding shares how his fast-growing agency left him exhausted until he “fired himself” from daily operations and empowered his team. By hiring a strong operational leader and adopting systems like EOS, he transformed the business and his life — moving from 90-hour weeks to true autonomy. His story highlights the power of trust, healthy conflict, and culture in overcoming burnout and building sustainable growth.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz sits down with Ryan Redding, Founder of Eightfold Advantage, to talk about scaling businesses without chaos. They discuss the shift from being a doer to a leader, the value of finding the right operational partner, and lessons learned from selling a business. With insights on culture, EOS, and Bloom Growth, Ryan offers practical advice and real-world stories for entrepreneurs ready to scale without sacrificing their lives.

Resources mentioned in this episode:

• Ryan Redding on LinkedIn
• Eightfold Advantage
• Blue Collar CEO podcast
• EOS Worldwide
• KickCharge Creative
• The Five Dysfunctions of a Team: A Leadership Fable by Patrick Lencioni
• The Advantage: Why Organizational Health Trumps Everything Else In Business by Patrick Lencioni
• Traction: Get a Grip on Your Business by Gino Wickman
• Don’t Get Mad at Penguins: And Other Ways to Detox the Conflict in Your Life and Business by Gabe Karp

Special Mentions:

• iBrand Visual
• Dan Antonelli on LinkedIn

Related episodes:

• “Entrepreneurial Lessons and Failures Building a $220M Empire With Tommy Mello” on Inspired Insider Podcast
• “Leading with Passion with Gino Wickman Founder of EOS Worldwide” on Inspired Insider Podcast
• “[One Question] Closing A Promising Startup with Mark C. Winters of RocketFuelNow.com” on Inspired Insider Podast
• “[Top Agency Series] Navigating a Merger and Becoming an End-to-End Digital Partner With Kevin Hourigan of Spinutech” on Inspired Insider Podcast
• “[Top Agency Series] Expanding Your Brand Impact Through Social With Duncan Alney of Firebelly Marketing” on Inspired Insider Podcast
• “[Top Agency Series] Most Valuable Advice When Selling Your Agency With Todd Taskey of Potomac Business Capital” on Inspired Insider Podcast
• “Raising Leaders for the Service Business With Chad Peterman” on Blue Collar.CEO
• “How to Walk in the Door and Add $20M in Revenue With Lawrence Castillo” on Blue Collar.CEO

Quotable moments:

• “I could not just outwork or outgrind my way to growth or to freedom or to clarity — I was stuck.”
• “The grinder of the business has to die in order for the leader to be born.”
• “The key to your freedom is actually having a team do the work and having clear, documented processes they all follow.”
• “It was simultaneously the most terrifying and liberating thing I’ve ever done — firing myself and trusting my team.”
• “Businesses are not made of spreadsheets; they’re made of people. Cultural due diligence might be the secret ingredient to an acquisition deal.”

Action steps:

1. Delegate responsibility and empower your team: Letting go of the urge to do everything yourself and entrusting capable team members with true responsibility helps break personal and organizational plateaus. This creates space for growth, prevents burnout, and fosters a culture where others step up.
2. Implement a structured operating system: These systems help founders move from reactive firefighting to strategic leadership.
3. Prioritize cultural due diligence during acquisitions: Paying attention to cultural alignment, not just financials, reduces friction and increases the odds of successful mergers or partnerships.
4. Embrace healthy conflict and debate: Fostering an environment where team members can respectfully challenge each other’s ideas leads to better decision-making and innovation.
5. Focus on personal well-being and work-life boundaries: Recognizing the signs of burnout and intentionally creating time for rest ensures sustainability for both leaders and their businesses. Prioritizing life outside of work helps prevent resentment and aligns business growth with personal fulfillment.

Episode Transcript

Intro 00:15

You are listening to Inspired Insider with your host, Dr. Jeremy Weisz.

Dr. Jeremy Weisz 00:22

Dr. Jeremy Weisz here Founder of InspiredInsider.com where I talk with inspirational entrepreneurs and leaders. I have Ryan Redding. You can check him out at EightFoldAdvantage.com. He’s also the host of Blue Collar.CEO. Ryan has been on the show before. I don’t have many people on twice. Ryan at the time of this has sold his company, so I figured we’d have him back on, talk about his learnings and then what’s on the horizon for him. And so, Ryan, this is part of the Top Agency Series and some other I always like to point out some other episodes people should check out of the podcast, and Kevin Hourigan was a good one. Who runs Spinutech. He started his agency in 1995, so it’s interesting to hear the journey of the internet business and the agency world through a couple decades. That was a good one. Also, Duncan Alney, who I know you know as well.

Ryan Redding: 01:21

Oh, Duncan, he’s a good dude.

Dr. Jeremy Weisz: 01:24

Firebelly Marketing. He’s got the the he’s got a great podcast interviewing CPG founders, beverage founders, mission based companies. So check those out. And Todd Taskey we’re speaking of acquisition here Todd Taskey helps pair agencies with private equity. He has a Second Bite Podcast. And he has a lot of interviews of me. You should probably go on his Ryan actually of talking to the journey of selling. He’s got people from private equity on and he’s got agencies on talking about the journey of selling. So check that episode out as well on InspiredInsider.com.

This episode is brought to you by Rise25. At Rise25, we help businesses connect to their dream relationships and partnerships. We do this in a few ways. One, we’re an easy button for a company to launch and run a podcast. We do the strategy, accountability, and the full execution and production behind the scenes. And number two, we’re also an easy button for companies gifting. We make gifting and staying top of mind to your clients, partners, prospects, even staff. Simple, easy and affordable. So you just give us a list of the people and we send them gifts every couple months for years to come.

So, Ryan, we call ourselves the magic elves that run in the background and make it stress free for companies so they can build amazing relationships and they focus on running their business. Right. So and for me, the number one thing in my life is relationships. I’m always looking at ways on how to give to my best relationships, and I’ve found no better way over the past decade to profile the people and companies I admire. Share with the world what they’re working on. Also, send them sweet treats in the mail. So go to.

Ryan Redding: 03:02

I’m going to.

Dr. Jeremy Weisz: 03:02

Go ahead.

Ryan Redding: 03:02

I’m going to vouch for you here. I’m not going to cut you off, but I will vouch as a unsolicited testimonial. I’ve used both of those services. You did our Blue Collar.CEO Podcast, which I freaking loved. Everything you guys did, your team incredible. And the gifting service we also use for our clients. Always loved because the easy button metaphor is spot on. Everything you guys did was thoughtful. It was intentional. I never had to check up on you. In fact, you guys were checking up on us. Dude, highly, highly recommend everything you guys do because you are. You have a great team.

Dr. Jeremy Weisz: 03:35

I appreciate that, and it means a lot coming from you because I know you run a well-oiled machine yourself. So check us out at Rise25.com or email [email protected] and I want to give a shout out to iBrand Visual. If you’re watching the video I haven’t updated my backdrop in like ten years and they created this for me. They create interior and exterior signs from startups to fortune 500. They do signs even at the you know, The Ritz. And so if you need something, if you’re a podcaster or if you just need to sign your inside or external business, go to ibrandvisual.com. Tell them I sent you. I don’t get anything for it, but I love them over there.

So I am excited to introduce Ryan Redding. He’s the Founder of Levergy, a digital marketing agency that helps home service companies scale through SEO, PPC, and branding. He sold Levergy to KickCharge Creative in 2025. He shifted his focus to advising entrepreneurs, agencies, home services companies on leadership and growth strategies. He’s also a certified Bloom Growth coach, helping business owners install operating systems so their companies run smoother, scale faster and work for them. As I mentioned, he’s also the host of the Blue Collar.CEO Podcast, and we’ll check him out at EightFoldAdvantage.com. So Ryan, thanks for joining me.

Ryan Redding: 05:01

Man, thanks for having me on two two times is in quite the honor. So thank you for making that happen.

Dr. Jeremy Weisz: 05:07

I want to start back to what kind of like go backwards for a second and, you know, with Eightfold Advantage. We were talking before we hit record. And whether it’s a digital agency and you mentioned, you know, it’s a software company. If it’s entrepreneur home services, people often in the journey feel stuck. They can experience burnout and hit plateaus personally and in the business.

So I kind of want to start there and go backwards and talk about some of those points for you, because obviously this is what you help business owners do, and you’ve kind of gone through those, I guess, through the fire before. Maybe start with the the plateaus and the ceilings and the what you experienced at different phases of the business with the plateaus and ceilings.

Ryan Redding: 06:04

Yeah. I think and actually let me, let me maybe go back before that because I think, I think anyone who’s built a business, especially from the ground up, has probably found themselves in a similar spot like I did. So for me, I started my agency in 2016, and one of the realities of just like starting a business from from scratch is like, you kind of have to do everything right. You’re the jack of all trades, you’re answering the phones, you’re doing all the product fulfillment for fulfillment or whatever the service that you do. You’re doing all the invoicing and payroll and tax like you, you are the thing and the as you start growing the company and as you start growing the people, you might have a playbook or some other company you admire, but you’re really you’re just kind of like figuring out as you go there Very, very few people who like are given like, here’s the manual.

Once you hit 1 million of revenue, here’s the decisions you should make and why. Here’s the $5 million revenue manual. Like here’s what you’re going to have to deal with and solve. You’re just kind of figuring it out. And what happens is because as a founder, you are you’re intimately familiar with all the areas, right? You’re familiar with what goes into making customers happy, what goes into fulfillment to make sure that your quality controls meets your standards and your own level of paranoia, like, you know, all these things, it’s so easy for you just to kind of jump in and do them. Even when you hire people, you jump and do them. So I was no different. I jumped in and did exactly what everyone else does, just like you’re just trying to keep afloat. I was very fortunate that when I started Leveregy, the business grew faster than I expected.

Not a lot of people have that experience. And so for a couple of years, it was just like hiring, training, trying to onboard new clients. It was just always trying to stay above what was happening. The the problem is though, because you’re going at that pace. For me, it was really difficult for me to stop, take the time to train someone else.

Right. I couldn’t train an account manager, I couldn’t train an SEO tech. I couldn’t train a web person. I just didn’t have the time to actually implement the training. I just I was busy trying to keep everything going, and I didn’t have time to stop and put together a manual, put together a process map.

It was really, really difficult. And if I did stop and put put thought into a process, by the time it would actually get like codified, written, put into play, I’d probably outgrown it. Right. So it was like this really weird sort of scenario. And at one point, at one point, I remember finding myself working 80, 90 hour weeks. My family saw me. And if I made it, if I made it to like, family dinner, like I was still on my phone. I’m like pecking, pecking at slack and like, I’m on chat and I’m like, responding to clients like I’m there, but I’m not there, you know? Like. And my kids tell me stories like that, that they felt like I was absent.

I wasn’t with them. I would miss soccer games like I’d miss I’d miss these parts of my life. Like, that’s not why you started a business. You start a business for freedom. Like to do what you want, when you want, how you want, where you want.

Like that’s why everyone starts a business. And I found myself just like being chained to my phone, chained to my computer. And I remember the like, the most stressful times for me was like going on a family trip, remember? Oh gosh, might have been 2018, 2019. We decided we’re going to take a week and go to Lake of the Ozarks, which is this beautiful lake in central Missouri, and I’m on my computer the entire time, driving like I have my wife at the time drive, and I’m just, like, pecking away.

Just I couldn’t get away to even go to the lake. And once I go to the lake, I’m like, on my laptop. Everyone else is like skiing and doing jet skiing and doing the fun lake things. And I’m like, stuck trying to not die. And it was exhausting. And I remember at one point I want to say we probably had 50 people on our team, maybe 50 or 60 people on our team at this point. And I’m telling someone who also ran an agency, he was outside of Atlanta, and I remember I remember just like talking to him about my my day. And for me, it was just like it was just a day, right? It was like, I’m not proud about it. I’m not embarrassed about it.

I’m just like, I’m just doing whatever I have to do to survive and take care of my clients. Just take care of my team. But I’m I have nothing else to give. I can’t add more time in the day, and I can’t just get this stuff up. And I remember his name was Jeremiah.

Jeremiah looks at me and says, dude, why on earth do you have all those people on your payroll? They’re all really smart people. Why do you have them on your payroll if you’re just doing all their jobs? And that was the first time. That was the first time where I stopped and realized that I had a problem, that I could not just outwork or out grind or out hustle my way to growth or to freedom or to clarity.

Like I was stuck. Turns like, turns out that’s a really common experience for a lot of entrepreneurs. Like that wasn’t unique to me. That is a really common experience that people are just trying to keep up and keep the wheels turning, and they find themselves like, at the end of the day, it’s kind of like three buckets. It’s either they they find themselves with no time, you know, like they can’t leave the computer at home and just go to the lake for a week.

They find themselves like the profit is actually not where they think it should be. It’s just like leaking. But they’re not quite sure where or why or how to fix it or it. They don’t feel like the business is growing, like it’s just stuck. They hit a ceiling.

It’s like one of those three things. A lot of entrepreneurs find themselves at at different points. And I remember being so, so struck when Jeremiah told me that that I went to my staff meeting the next day, which was already scheduled. It wasn’t an ad hoc. It was like I was already on the calendar. And I told people I walked in, I said, hey. As of now, I it has occurred to me that I am doing a lot of your jobs that you guys have been hired to do, and I’m just in your way.

So as of now, I am firing myself. You guys are responsible for taking care of your responsibilities. You break it, you fix it. But I’m going to Napa. And I went to Napa for two weeks just to kind of hard reset my cadence. And it was simultaneously the most terrifying and disruptive and liberating thing I’ve ever done. Kind of like, all in ones, you know? Like I just found myself.

Dr. Jeremy Weisz: 12:41

Just a cold turkey kind of guy.

Ryan Redding: 12:44

I’m not by default. That’s the crazy part. That’s not. I’m usually very intentional, very methodical and very systematic. And this is just like, if I don’t do this, either my business is going to break or my body is going to break. One of those two things is going to break because I can’t keep up the pace. My my health was starting to take effect. Like, I, I could not just out grind myself to freedom, and I had to just force myself to learn new habits. And I had to force the team like what it means to do things and to put out their own fires instead of come to me for everything. It was it was crazy.

In in that two week period. The Napa one highly recommend everyone fires themselves and goes to Napa like there is no downside of this decision ever. It is one of the most amazing experiences people should make, but two it forced me in the spot to really think through systematically what type of business do I want? But more importantly, what type of life do I want? Because I definitely, definitely, definitely did not start the agency to be a slave to it.

I did not start the agency to grind 90 hours a week. I started the agency to take care of my family, to have freedom to like, do things that I wanted on my terms. And the way I was working wasn’t working.

The crazy part, which made it hard on the outside, is if you looked at my my financial statements during that period, you would have every reason to think that we were insanely successful. Like our growth was on point, our top line was growing, our bottom line was growing. Our team was like, generally speaking, happy from a from a PNL or balance sheet sort of perspective. If you just look at the numbers, everything was amazing. Don’t touch it. But from a quality of what it felt like to be in the business, be strapped in the business, It wasn’t something that I wanted. Like I wasn’t happy, it wasn’t fulfilled. My family was starting to resent my relationship to the business and my role in the business. It was a spot that I could not sustain. And Napa. Napa marked a reset to me. It really, really did.

Dr. Jeremy Weisz: 14:54

Do you think that was the case, Ryan? Because that got you in the beginning, that got you to where you were and you just didn’t let go of like as a leader, some of these tasks or things or like, what do you. Yeah. How did it get that far? I guess because it’s like a death by a thousand paper cuts type of thing. It seems over. Yeah.

Ryan Redding: 15:18

Yeah.

Dr. Jeremy Weisz: 15:19

And is that what you think happened or what? Yeah.

Ryan Redding: 15:21

Yeah, I think it’s spot on. I think I think starting off every business, like, starts off, the owner has to grind. Like you just have to grind. Starting off, not many people start off with, like, millions of dollars in the account and you could hire people like most people aren’t in this like pre-seed fundraising rounds. Or it’s like, hey, we got money in the bank.

We don’t know how we’re going to make money, but we have cash for days. So take your take a breather. Most people just have to work harder and they have to grind. And that’s true if you’re an agency. That’s true if you’re a plumber.

That’s true if you’re a lawyer. Like it doesn’t matter your industry, right? You just like do more of the things. If you’re making cupcakes, you just like, cool. Let’s just make more cupcakes.

At some point, you realize the key to your freedom and the key to like that next level of growth for the business and for you as a person and as a leader isn’t just make more cupcakes. Like you run out of the ability to make cupcakes. At some point you have to realize, like, damn it, I gotta make a bakery. I have to figure out actually how to have this machine make cupcakes and have somebody else manage the machine. So once you start realizing that the key to your freedom is actually not you doing more of the thing.

It’s not you saying more patience. It’s not you building more websites. It’s not you, you know, knocking on more doors. The key to your freedom is actually having a team do the work and having clear, documented processes they all follow. Having the right team, like the right people in the right seats, knowing that they’re all incentivized to do the thing that’s in the best interest of the business, like the whole point is to make the bakery. And I think everyone starts off by like this desire and this need. You have to you have to you have to just make more cupcakes. My friend Tommy Mello, which I think I think he’s been on your show before.

Dr. Jeremy Weisz: 17:09

Yes.

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