What I Learned Building and Selling My B2B Podcasting Agency

For ten years, my business partner Dr. Jeremy Weisz and I built Rise25, a B2B podcast production company that started as a side project and became a full services business. In 2025 we sold it to The Podcast Consultant, with Jeremy staying on to help run the combined company while I stepped away to build Smart Business Revolution AI.

In this post, I want to share a founder’s view of what actually mattered: understanding that a services business is a labor business, tracking margins by service line, recognizing when your market is consolidating, being honest and clear-eyed about your business, and knowing what you are giving up when you sign a non-compete and stop doing the work that has defined your life for 10+ years.

Most advice about selling a business focuses on valuation and negotiation. Those matter. But what helped more in my case were quieter choices: building recurring revenue, documenting processes, removing founder bottlenecks, making yourself less indispensable and treating the sale as one transition in a longer career rather than the end of the story.

If you are running a services company and wondering how it might end, my hope is that these lessons give you a more realistic picture of what the path can look like and what you can start doing now, long before you ever talk to a buyer.

In the early days

Rise25 did not begin as a podcast production agency. It started as a series of small experiments: mastermind events, relationship-building dinners, and a shared belief that long-form conversations (online or in person) are one of the fastest ways to build real relationships in business. Over time those experiments turned into a company that produced a large number of B2B podcasts for clients who wanted a structured way to meet ideal partners and customers.

Like many services companies, we had long stretches where the business looked successful from the outside but the internal economics were not as strong as they needed to be. The turning point was when I started treating Rise25 as a labor business and looking hard at margin by service line rather than only top line revenue. That shift made the company healthier and, eventually, more interesting to a buyer.

We sold into a market that was clearly consolidating. More podcast agencies were appearing every year, AI was reshaping how clients created and distributed content, and it was obvious that a few larger firms would end up with more scale, more referral flow, and more resources than anyone going it alone. Joining up with The Podcast Consultant was a way to be part of the consolidator instead of getting slowly out-competed by one.

The Smart Business Revolution’s GEO and AI visibility work grows out of the same instincts that built Rise25. Generative Engine Optimization is a different market, but it is still about relationships, trusted conversations, and getting the right companies to show up when buyers are making decisions. But we’ll get to that later.

Key Takeaways

• A services business is a labor business first. Until you understand your labor efficiency and margin by service line, you are mostly guessing.
• The real asset is rarely the deliverable. In our case it was the relationship engine the podcast created for clients, not the audio files.
• Any offer that requires clients to change deep habits is much harder to scale than it looks on a whiteboard.
• If you think you might sell one day, build a business that can run without you whether or not you ever exit.
• Industry consolidation is not an abstract idea. It becomes real when you see competitors raise their game and you decide whether to join them or compete with them.
• Deals involve math and emotion on different timelines. You may make peace with selling months before the paperwork closes, then still feel the impact on closing day.
• Non-competes and other post-close commitments deserve as much attention as headline price because they shape what you are allowed to do next.
• Selling a services business is easier when you already know what you want to build after the sale instead of treating the exit as a finish line.
• Smart Business Revolution’s GEO and AI visibility model is built on the same relationship-first principles that made Rise25 work for clients in the first place.

Table of Contents

• 1. How Rise25 Actually Started
• 2. Finding a Model That Could Work Long Term
• 3. How the Sale Came Together
• 4. Lesson 1: A Services Business Is a Labor Business
• 5. Lesson 2: The Asset Was Never the Podcasts
• 6. Lesson 3: Selling Habit Change Is Harder Than It Looks
• 7. Lesson 4: Build a Sellable Company Whether or Not You Sell
• 8. Lesson 5: Pay Attention to Industry Consolidation
• 9. Lesson 6: Know What You Are Giving Up
• 10. What I Am Building Now
• 11. DIY Versus Advisors When You Sell a Services Business
• 12. Questions to Ask Before You Sell

How Rise25 Actually Started

Rise25 did not start as a carefully planned agency. It started because Jeremy and I were both early to podcasting and to the idea that long-form interviews could be a strategic way to meet people. We each had our own shows. I was still practicing law in Silicon Valley and San Francisco, taking more interest in new media than to the cases on my desk. The podcast was a way to talk to people I would never have met otherwise.

Those early conversations led to opportunities: legal clients, referral partners, friendships, and introductions that would have been impossible with a cold email. The medium looked like content. The value was in the relationships. That pattern has shaped everything I have done since.

By 2015, Jeremy and I knew of each other through our mutual friend Andrew Warner but not well. We both ended up at the same conference in Napa Valley, hosted by Jayson Gaignard at MastermindTalks. Jeremy asked if I wanted to run a small mastermind the day before. I was saying no to almost everything that year. For reasons I still cannot fully explain, I said yes to that.

The event worked. People got value, and we enjoyed running it. We did another one, at a resort in Austin, at a much higher price point. For a few years that was the business: small, in-person masterminds that relied entirely on relationships.

Finding a Model That Could Work Long Term

By 2018 the in-person model had stopped working for me. We were working extremely hard and traveling constantly. I had four young kids at home. Every good quarter required getting on a plane.

If I didn’t get on a plane, we weren’t making money.

The business was real, but it was not the life I wanted for the next decade.

At the same time, our own clients kept asking a simple question. They saw how we were using podcasts as a relationship tool and wanted to know how they could do it. Helping them was a natural extension of what we were already doing, so we started producing a few client shows as a side offer.

When COVID hit, everyone was locked at home and still needed a way to build relationships with clients, partners, and referral sources. The thing we had been doing on the side became the whole business. Rise25 shifted from in-person masterminds to B2B podcast production focused on relationship driven shows.

From there the company grew steadily. I went through the great EO Accelerator program. Jeremy went through Goldman Sachs 10,000 Small Businesses. We both eventually joined Entrepreneurs’ Organization. Being in rooms with owners who were a couple of years ahead made a bigger difference than any single tactic. It normalized the idea of building a company that could outgrow its founders.

How the Sale Came Together

For more than a year before the sale, I operated on a simple thesis. Podcast production as an industry was going to consolidate. More agencies were showing up every year. Competition was increasing. At some point a handful of firms would pull ahead because they had more scale, more brand recognition, and more referral flow than anyone trying to compete alone.

I did not want to wake up one day as a good small shop slowly losing deals to a better resourced competitor. I wanted to be part of the larger, combined company that had a chance to win that consolidation game.

So I went out and had the conversations. Between fifty and sixty of them, with companies in and around our space, about mergers and acquisitions in both directions. Most of those conversations went nowhere, which is exactly how the process is supposed to work. You learn quickly where businesses are incompatible in culture, economics, or strategy.

When we connected with Karl Hughes and Manuel Weiss at The Podcast Consultant, it felt different. They had independently arrived at the same view of where the market was going and what kind of company would be worth building over the next three years. We agreed on the strategy and the direction of the industry.

The math was the hard part. The combined company was not large enough to support four equal co founders. Someone was going to have to step off. I volunteered, not because I was noble, but because it was the answer that made the most structural sense and fit what I wanted to do next.

What Ten Years Taught Me

Everything below is what the ten years before it taught me.

Lesson 1: A Services Business Is a Labor Business

For a long time I thought of Rise25 as a marketing company. From the inside, though, it behaved like a classic labor business. We bought hours from a distributed team and sold outcomes to clients. The game sat entirely in the gap between those two numbers.

Once I started tracking labor efficiency and margin by service line, things that had been fuzzy for years came into focus. Some services that felt impressive delivered weak margins. Other offerings that looked small from the outside quietly carried a lot of the profitability.

If I were starting again, I would build that habit from day one. In a labor business, the numbers are not an afterthought, they are the strategy. Everything else is commentary.

Lesson 2: The Asset Was Never the Podcasts

Over a decade we produced a very large number of podcast episodes. Almost none of the real value lived in the audio files.

The asset was what a podcast did for a business owner. It gave them a legitimate reason to spend an hour with someone they wanted to know. It gave them something to offer, an interview and a spotlight, instead of something to ask for. It turned cold outreach into an invitation that felt good on both sides.

Our best clients understood this immediately and treated their show as business development. They built systematic follow up into their process and turned interviews into long term relationships. Clients who treated the podcast purely as content marketing were often a little disappointed because they measured success only by downloads and listens.

Every business I have built has used some version of this pattern. The medium changes. The mechanism does not. Today, when we work on AI visibility and GEO, the same principle applies. The point is to earn and deepen relationships, not to glorify any single channel.

Lesson 3: Selling Habit Change Is Harder Than It Looks

From the outside, Rise25 looked like a done for you podcast service. We booked the guests, handled the tech, edited the audio, wrote show notes, created blog posts, and handled distribution. Clients received a finished asset every week without touching the production side.

The one thing we could not do for them was the thing that mattered most. They still had to show up for the interviews and they still had to follow up with guests afterwards. That meant our product depended on clients changing their habits around time, outreach, and relationship management.

Some clients embraced that rhythm quickly and had incredible results. Others bought with real enthusiasm but struggled to build the habit. No amount of white glove service on our side could make up for a calendar that never had time blocked for interviews or a sales process that never prioritized follow up.

If you sell any service that depends on clients behaving differently than they did last month, you are in the behavior change business as much as the delivery business. Price for that. Build onboarding around it. Screen for it in your sales process. I would do all three more intentionally if I were starting again.

Lesson 4: Build a Sellable Company Whether or Not You Sell

John Warrillow’s book Built to Sell and his podcast were useful to me because they reframed how I thought about building a services business. The core argument is simple. The traits that make a company sellable are the same traits that make it less stressful and more valuable to own.

Recurring revenue, documented processes, a client base without dangerous concentration, a delivery team that can operate without the founder, clean financials, and clear positioning all matter whether or not you ever take a company to market. They also happen to be exactly what potential buyers look for.

When we eventually sold Rise25, those traits were part of what made the company attractive. They were not things we built only as a pre sale exercise. They were the reason the business was livable in the years before the sale.

Lesson 5: Pay Attention to Industry Consolidation

Market consolidation is one of those phrases that sounds abstract until you are in the middle of it. In podcast production, you could see more agencies appearing, more competition for the same clients, and more pressure on pricing. At the same time, AI was reshaping how companies created, edited, and distributed content.

In a market like that, a few players usually grow larger than the rest. They have more budget to invest in systems and people. They become the default recommendation when someone asks a peer for a referral. If you ignore that pattern for too long, you can end up working very hard for a shrinking share of the opportunity.

My goal was not to time the top of the market. It was to be honest about where the industry was headed and to put Rise25 in a position to be part of a stronger combined company rather than getting slowly pushed to the margins.

Lesson 6: Know What You Are Giving Up

When you sell a services company, you are not only selling cash flow. You are also agreeing to certain constraints on what you can do next. In my case, that included a non compete that I would absolutely have asked for if I had been on the other side of the table.

Signing that agreement meant acknowledging that I had spent a decade becoming very good at one thing and that I was now agreeing not to do that thing for a period of time. That is a serious decision. It deserves as much attention as the multiple on earnings or the earn out structure.

I also chose to pause the Smart Business Revolution podcast, which I had been hosting since 2010. No one required that. It was my own recognition that I was entering a new chapter and that I should not keep running the old chapter’s marketing on the side. Both decisions were right. Neither was free.

What I Am Building Now

After the sale, I knew I wanted to stay in B2B. I also knew I do my best work in markets that are on the upswing rather than ones that are already mature. Podcasting played that role for me around 2010. Today, Generative Engine Optimization and AI visibility feel similar.

Smart Business Revolution AI is an advisory and GEO agency focused on one question: when your ideal buyers ask an AI assistant for help, does your company show up, and if not, what will it take to change that? Under the hood, that work relies on the same mechanics that made Rise25 valuable. Clarifying your positioning, understanding buyer behavior, building the right relationships, and creating content that helps people make decisions.

I am running this business with a small, lean team and leaning heavily on AI and AI agents inside the operation. After a decade of managing a large distributed services team, I wanted to see how much a handful of people and modern tools could do. So far the experiment has been worth it.

DIY Versus Advisors When You Sell a Services Business

One practical question founders ask is whether to run a sale process themselves or work with advisors and brokers. There is no universal right answer, but there are clear patterns.

If you are early in the journey, you do not need to decide this now. What you can do is build the kind of business that would give you options later: clean numbers, recurring revenue, documented processes, and a team that can operate without you.

Questions to Ask Before You Sell

Before you open any serious conversation about selling a services business, it helps to ask yourself a few blunt questions.

• If I did not sell, what would I want this company to look like in three years?
• Am I building something I enjoy owning, or am I trying to escape a business that drains me?
• Do I understand where our margins are strong and where they are weak?
• Is there visible consolidation in my space, and if so, which side of that do I want to be on?
• What kind of non compete or other restrictions would still feel fair to me a year after closing?
• What would I want to build next, separate from this company?

Thank You

To Jeremy, for ten years. We built something real and I’m glad it’s continuing.

To the Rise25 team, several of whom stuck with us for the better part of a decade. You did the work.

And to the clients who let us into their businesses and trusted us with the relationships that mattered most to them. That was never lost on me.

Conclusion

Selling a services business is not a neat, cinematic moment. It is the result of hundreds of small decisions about how you treat labor, which offers you double down on, how you document processes, when you pay attention to market shifts, and what kind of work you want to do next.

If you are somewhere on that path, my suggestion is simple. Get honest about your numbers. Pay attention to how hard your model leans on founder habit change. Build a company that could run without you even if you never sell. Watch for signs of consolidation in your space. And be as thoughtful about your next chapter as you are about this one.

CTA: If you are thinking about what comes after your current services business, start by clarifying where your time and expertise create the most leverage, then design your next chapter around that instead of only aiming for a headline exit number.

Related Guides

• GEO Search Optimization
• GEO AI Optimization Services
• What Is AI Visibility?
• Smart Business Revolution Services
• Contact Smart Business Revolution

FAQ

When should I start thinking about selling a services business?

Sooner than you think. You do not need to hire a broker or start a formal process, but you can start building a more sellable business years before you ever talk to a buyer. Clean financials, recurring revenue, documented processes, and reduced founder dependency all make your life easier now and your options broader later.

How important are margins when selling a services company?

Margins are central. Buyers care about what the business keeps after paying for the labor required to deliver the work. Two companies with identical revenue can look very different once you break out delivery costs by service line. Tracking that gap regularly is one of the fastest ways to improve both your experience as an owner and your attractiveness as a potential acquisition.

Do I need an advisor to sell a small services firm?

Not always. Founders with strong networks and a short list of logical buyers can sometimes run a simple process themselves. An advisor becomes more valuable when you want broader reach, help shaping your story, or discipline around negotiation. The right answer depends on your goals, energy, and complexity of the deal.

What should I watch for in a non compete?

Look at scope, geography, and duration, then test those terms against what you might want to do next. A non compete that looks reasonable on paper can feel different a year later if it blocks you from serving a market you care about. Be as detailed about future plans as you can before you sign.

How do I know if my industry is consolidating?

Signals include competitors raising more capital, larger firms rolling up smaller ones, clients mentioning the same names repeatedly, and more pressure on pricing. None of those automatically mean you should sell, but they are a good reason to think more strategically about where you want to sit when the dust settles.

Can I build another company in the same space after I sell?

That depends on the non compete and other restrictive covenants you sign. Many founders can eventually work in the same broader industry again but may be limited for a period of time or within certain service lines. This is why clarity about your next chapter matters so much before you close.

How does this relate to AI visibility and GEO?

The mechanics are similar. Whether you are building toward an exit or building toward better AI visibility, you are still aligning your business with how the world discovers and decides. In both cases, clear positioning, strong relationships, practical proof, and repeatable systems matter more than any single tactic.

Ready to start designing what comes after your current services business? Begin with the questions in this article, then explore the related guides above to see how Smart Business Revolution approaches long term visibility and positioning in the age of AI.

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