[Top Agency Series] Trust, Positioning, and Smarter Agency Acquisitions With Karl Hughes

Karl Hughes is the CEO of The Podcast Consultant, a podcast production company that helps business and financial industry experts build authority and generate long-term value through audio and video content. He also serves as CEO of Rise25, where he helps B2B companies generate clients, referrals, and strategic partnerships through podcasts, and is the Founder of Draft.dev, a developer content agency he launched in 2020. Karl also hosts Retained Trust, a podcast featuring conversations with digital service entrepreneurs about building, scaling, and selling successful service agencies.

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

• [6:02] Karl Hughes shares how his engineering background led to entrepreneurship and Draft.dev
• [9:33] Lessons from scaling Draft.dev past $2 million and managing rapid growth
• [13:46] Testing business partnerships before making a bigger commitment
• [19:24] How acquisition criteria evolve as buyers gain experience and scale
• [21:44] Karl explains why trust and buyer-seller alignment matter in agency acquisitions
• [30:17] What The Podcast Consultant acquisition revealed about client retention and service expectations
• [35:26] Why niche positioning matters in high-trust industries like financial services
• [40:13] Rise25’s relationship-driven approach to podcast-led business growth
• [55:52] Karl shares how delegation creates greater leverage across growing businesses

In this episode…

Acquiring an agency can accelerate growth, but a successful deal requires far more than finding a profitable business and agreeing on a price. Buyers must evaluate the people, financials, positioning, and long-term fit while preserving the strengths that made the company valuable in the first place. What does it take to make an agency acquisition work well beyond the closing table?

For Karl Hughes, a former software engineer turned multi-business entrepreneur and experienced agency acquirer, the strongest deals are built on trust, careful due diligence, and post-acquisition patience. He highlights the importance of choosing a buyer or seller you can work with throughout diligence, transition, and any long-term payout structure, rather than focusing solely on the biggest number. Buyers also need the discipline to observe before making major changes, since established teams, processes, and client relationships may already be working well. As acquisition experience grows, criteria can become more flexible, allowing buyers to recognize opportunities in companies with solid revenue or leadership even when the financials are not perfect. Karl also emphasizes the value of sharpening a company’s positioning after acquisition by identifying where it already succeeds and doubling down on that niche.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz sits down with Karl Hughes, CEO of The Podcast Consultant, to discuss smarter agency acquisitions. They explore building trust with sellers, refining acquisition criteria, and positioning acquired companies for growth. Karl also shares how to integrate businesses without disrupting what already works.

Resources mentioned in this episode:

• Karl Hughes LinkedIn | Website
• The Podcast Consultant
• Draft.dev
• Rise25
• Retained Trust
• Finance Podcast Production Insights
• Rocket Fuel: The One Essential Combination That Will Get You More of What You Want from Your Business  by Gino Wickman and Mark C Winters
• The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Timothy Ferriss
• The Alchemist by Paulo Coelho
• How Will You Measure Your Life?: Using Innovation Theory to Create a Life Strategy for Career, Relationships, and Integrity by Clayton M. Christensen, James Allworth, Karen Dillon
• The Top Five Regrets of the Dying by Bronnie Ware
• Buy Then Build: How Acquisition Entrepreneurs Outsmart the Startup Game by Walker Deibel
• The E-Myth Revisited: Why Most Small Businesses Don’t Work and What to Do About It―A Guide to Starting a Business in a Productive and Successful Way by Michael E. Gerber 
• Who Not How: The Formula to Achieve Bigger Goals Through Accelerating Teamwork by Dan Sullivan with Dr. Benjamin Hardy
• Karl Hughes Recommended Books
• Zo Computer

Special mentions:

• Manuel Weiss on LinkedIn
• Todd Taskey on LinkedIn

Related episodes:

• “[Top Agency Series] Most Valuable Advice When Selling Your Agency With Todd Taskey of Potomac Business Capital” on the Inspired Insider Podcast
• “Building a Great Team and More Helpful Insights with Jason Swenk Host of The Smart Agency Master Class Podcast” on the Inspired Insider Podcast
• “[Top Agency Series] Navigating a Merger and Becoming an End-to-End Digital Partner With Kevin Hourigan of Spinutech” on the Inspired Insider Podcast
• “From Agency Owner to Fund Investor: Grant Hensel on Buying Enduring Businesses” on Retained Trust
• “Building Barrel Holdings: Peter Kang on Scaling and Exiting Agencies” on Retained Trust
• “From Podcast to Portfolio: Will Smith’s ETA Journey” on Retained Trust
• “[Top Author Series] The Two Leadership Traits To Explode Your Business With Mark C. Winters Author Founder of RocketFuelNow.com” on the Inspired Insider Podcast
• “Leading with Passion with Gino Wickman Founder of EOS Worldwide” on the Inspired Insider Podcast

Quotable moments:

• “We’re a little more flexible with some of these things that we used to not be so much.”
• “You want to trust your buyer. Otherwise, just, you know, steer clear if it’s too good to be true.”
• “We don’t just immediately assume we know what to do better than, you know, what’s already there.”
• “Niche it into a space where it’s already successful and double down on what already works.”
• “The end result should be higher leverage of your time. That’s the goal.”

Action steps:

1. Prioritize trust in every acquisition: Strong buyer-seller relationships make due diligence, transitions, and long-term payout arrangements smoother and reduce the risk of costly conflicts.
2. Evaluate more than just financial performance: Looking at client retention, team strength, cash flow, and owner integrity can reveal whether a business is truly a good acquisition fit.
3. Avoid making major changes too quickly: Taking time to understand existing teams, processes, and client relationships helps preserve what already works and prevents unnecessary disruption.
4. Sharpen positioning after an acquisition: Identifying where a company already performs well and doubling down on that niche can strengthen differentiation and make future growth easier.
5. Build leverage through thoughtful delegation: Assigning the right work to people or technology allows leaders to spend more time on higher-value decisions, relationships, and growth.

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 from InspiredInsider.com. I am super excited to introduce Karl Hughes. You can check out ThePodcastConsultant.com and now also Rise25.com. So Karl, I’m going to formally introduce Karl in a second, but I always like to point out other episodes of the podcast, Karl, that people should check out.

Since this is part of the top agency series, some of the top ones, I was actually on Inspired Insider a day ago. Who should we mention? I mean, the biggest goal Karl has and Rise25, The Podcast Consultant has, is to be the biggest, best company in the world doing podcasts for companies. And it’s really when I say podcast, we’re not doing podcasts for companies, okay? We are helping people build amazing relationships. If you could see over my head, that’s what we do. We help people build amazing relationships with their referral partners, their strategic partners, their clients, their potential clients, people in their universe. Right? That’s what it’s about. We do that on the back of a podcast forming real relationships, and we’ll get into it deeply.

So, but that’s so I’m thinking, okay, who has amazing connections in the agency space? So when they hear, oh yeah, this person may want to sell within that kind of, I say, awkward teenage phase. Karl. They’re like 1 to 4 million, right? It’s too small for PE sometimes, too little. There’s not a lot of, you know, it’s hard to sell a company in that range sometimes. And so that’s what Karl and the team is doing.

So we have Todd Taskey who’s an amazing resource. He’s got the Second Bite Podcast. And these are, by the way, episodes on Inspired Insider. You could check out these people. But he helps pair agencies with private equity. But those are typically larger on the larger side. Jason Swenk is another one. We’re both a part of Jason Swenk’s mastermind, and he’s got an interview of when he started his company, how he ended up building it to eight figures and selling it. And then another one is Kevin Hourigan. Kevin Hourigan has had his agency Spinutech since, I think, 1995. Karl. So it was interesting to hear the span of business, the internet and agency life over several decades. That many more on InspiredInsider.com and maybe Karl any favorite of your episodes that you’ve done and talk about your podcast for a second.

Karl Hughes: 03:03

Oh yeah. Sure. Well, we just recorded an episode of Retained Trust, so that’ll be fun when it comes out. I probably, I don’t know if you’ll beat me to release or I’ll beat you to release, but it’ll be around the same time. I imagine.

Dr. Jeremy Weisz: 03:13

You’ll probably beat me.

Karl Hughes: 03:13

You know, some of my favorites recently, Grant Hensel’s, a friend of mine here in Chicago, he did one with me in February where we talked about, he’s actually moved from owning an agency to now running a fund that invests in search funds. And so that’s kind of adjacent to acquisitions. So I’ve learned a ton about him, from him. Peter Kang is another one I had around the same time. He also has been building and also buying agencies and a holding company for the last few years. Really cool guy. I did one as well with Will Smith, he does a podcast called Acquiring Minds. Will is really connected and smart guy in the world of search funds. He interviews a lot of people doing search funds for his podcast. And again, since I’ve been doing a lot of acquisitions in the last year, it’s just been the last few years. It’s been really fun to connect with these people who are, yes, in agencies, but also kind of in this adjacent space of acquisitions and M&A. So yeah, those are some that come to mind. Jeremy. Maybe recent ones.

Dr. Jeremy Weisz: 04:13

Yeah. I mean, we’ll talk about your experience with buying agencies and possibly what sellers should be thinking about when they’re ready to sell or if they’re ready to sell. We’ll get into that. But I always before I introduce you, Karl, like this episode is brought to you by The Podcast Consultant and Rise25. And, you know, really, we help businesses give to and connect to their dream relationships and partnerships that I just said, but we are an easy button for a company to do that, to launch and run a podcast. We do the strategy, accountability and the full execution and production. You know, for me and Karl has much of this mentality too, which is the number one thing in my life is relationships, and I’m always looking at ways to give to my best relationships. And I found no better way over the past over 15 years at this point, podcasting to profile the people and the companies I admire. So if you have questions, you can go to either Rise25.com or ThePodcastConsultant.com. You can email [email protected] to learn more also.

So I’m excited. So Karl Hughes is a former software engineer turned multi-business entrepreneur. He’s bought and sold several niche marketing agencies. He’s creating a powerhouse of podcast production companies, which I mentioned The Podcast Consultant and Rise25. So Karl, thanks for joining me today. And I want to, we’ll get into that. But I do want to just fast forward through your background a little bit, because you have a very interesting background as a software engineer, from startups to Draft.dev to now what you’re doing. So talk a little bit about just your starting point in your career because like how we start is, you know, myself being a chiropractor, how we started is not how we end up.

Karl Hughes: 06:02

Exactly. Yeah. I think we both share this like weird backgrounds for what we do now, Jeremy. So I can appreciate that. Yeah. You know, in college, I wanted to get into engineering for two reasons. One is I loved solving problems. And I’m fairly technical and I like to kind of really understand how things work. The other side was I had a physics teacher in high school who told me I was too much of a class clown to make it as an engineer, and so I had to prove him wrong. So, Mr. Dahlberg, if you’re listening, you know, I’m.

Dr. Jeremy Weisz: 06:33

I’m gonna find him on LinkedIn.

Karl Hughes: 06:34

Yeah, yeah. Yeah.

Dr. Jeremy Weisz: 06:35

Right, right.

Karl Hughes: 06:36

He’s retired. I think he’s retired now. No, but seriously, like, I like solving problems part. What I realized is I got into the world of, you know, actually being an engineer is that I was a fairly average engineer. I’m not a great detail person, which isn’t necessarily a good skill if you want to be the best individual contributor as an engineer. But I’m really good at communicating and interfacing with people and as an engineer who is fairly competent but a pretty good communicator, there’s a really great role out there, which is like managing engineers because, look, I don’t have to be the smartest engineer in the room, but I do have to understand enough of what they’re talking about to merge it with what the business needs from their work.

So that’s what I did with startups was, you know, yes, I was an engineer early on, but I also would hire the early engineering teams and work with the leaders, the founders, who are usually less technical to make sure they understood where the product was going and what was possible and how fast things would go and things like that. So really fun experience, I loved it. And then Covid hit and the company I was working for really hit like a snag as far as like they weren’t going to be able to raise funding, they weren’t growing that fast and they just needed to figure something out cashflow wise. So they started cutting all of our hours and kind of, you know, battening down the hatches, so to speak, and just trying to survive. They did survive and they did sell. But in the meantime, I started picking up some freelance work as a writer and would. It sounds weird, but surprisingly, there’s a lot of companies out there that would reach out to engineers who have written things on the internet and say, hey, would you want to write something for our company blog? Because it’s a marketing thing and they needed really technical people to market.

I’ll fast forward through it. But that became Draft.dev. We grew really quickly. We hired a team. I started to prophesize it and build it into a real company. You know, within a couple of years we were doing it over 2 million in revenue. And so it was a sort of right time, right place kind of business. I don’t think I could replicate that again. If you gave me, you know, a shot at it. It was just the moment in time was right. And I was the right person to do it.

So that was the start for getting into entrepreneurship for me. So I had been at these venture backed startups, and then Draft.dev was kind of this self-funded, less of a startup and more of just a bootstrapped small business. And it just made me realize how powerful owning your own business is as a wealth builder, as an interesting thing to work on as a problem solving thing to work on and as just an opportunity to like, learn from an experience. And so yeah, that was getting into entrepreneurship for me.

Dr. Jeremy Weisz: 09:08

I mean, Karl, like, you know, capturing growth is sometimes hard to do, right? So you did do that successfully with Draft.dev. I’m wondering, what were some of the challenges with the growth? Right? I don’t know if they’re hiring challenges because like you have to do a lot to when you grow that quickly in that amount of time, you know, just talk about some of the challenges.

Karl Hughes: 09:33

They’re super hard. I mean, like, I think as any small business owner will tell you, the people they hire early days are probably not the people who scaled with them. It just, it’s rare that that happens. And again, there’s some people that will carry through the whole journey, but like other people, move on because they want to go work at something else. They want to go start their own thing, like whatever.

And so the people I first started working with were just freelancers that wanted to help me out, like editing some stuff here and there. And I basically, as Draft.dev grew and I was driving more sales in demand, I kind of promoted those people into then leadership and operational leadership roles, and they were just as lost as me. And I think there’s something to like trying to run a small company with growing fast, but everybody is in a totally new world and role is pretty tough. And I, you know, we screwed plenty of things up.

I’ll give you an example of this. This is like, again, like a dumb entrepreneurial move. Early on, we had a negative cash cycle, meaning I would get a client to sign for a three month commitment. Then I would start the work. We would invoice them after we sent them the very first article and had already produced 5 to 6 behind the scenes. Then we’d give them 30 to 60 days to pay that invoice. And in the meantime, I’ve been racking up bills, paying my team and paying all our vendors and paying myself. We were adding, in theory, $20,000 a month in revenue, but in practice losing cash every month because of that. So there’s things like that that I was just completely naive about. Like, I didn’t understand cash cycles. I didn’t even, I’d never thought about that before. Anybody who’s been doing this for a long time will tell you, well, duh, collect the money up front, especially if you got a lot of demand. Like that’s great. You can self-fund. I did eventually do that, but it took some time to learn that and transition it.

And so similar mistakes like that we made all over the place, around hiring, around processes, around treating clients the right way. Again, like we didn’t, I don’t think we made any fatal errors because the company survived and has done fine. But I do think we made a lot of dumb mistakes that I’ve tried to avoid since.

Dr. Jeremy Weisz: 11:40

I mean, sometimes you were working with some big companies, right? And so some of the companies may require like, hey, we only pay every 60 or 90 days too. Right. So.

[Continue to Page 2]