Questions

1. Is Classic City a business or a practice?

Revenue went from $1.28M → $888K → $802K. You moved from employees to contractors, exited the office, cut the fractional CFO. Every optimization has been about subtraction. The business is leaner and healthier — but it's also smaller. At what point does "right-sizing" become "shrinking"? And more importantly: do you want to grow it again, or have you discovered that what you actually want is a high-income solo practice with a support crew? Those are two very different businesses with very different next moves.

ANSWER: I know that I don't have a desire to run a multi-million humongous agency with a ton of full-time employees. That does not sound very enjoyable to me. The only way that I think I would be down for that is if I was able to find somebody that was willing to take the reins of the company and do most of the nuts and bolts of running the business. Basically, the idea of hiring a CEO.

I think I've realized that my sweet spot is building strong networks of connections and letting the business compound upon itself, even if that means that growth year over year is slow.

The thing is, the revenue numbers that you notated from before are actually going to be another year of decline, because in 2026, unless something crazy happens, we will not hit $800,000 of revenue. It will more than likely be closer to $500, because you actually said it somewhere in one of your next questions.

The simple fact is that I really only need to close about $150k this year to be profitable, which is roughly correct. Going back to your point about right-sizing, my CFO actually pointed that out, middle point of last year. You can only subtract so much, right? You can do subtraction in the name of "let's get lean", but eventually there becomes a stopping point to that.

I definitely am thinking that probably more what I want is a high-income solo practice with a support crew. If I can scale that model, then great. I can increase my number of really dedicated contract folks from three to six, and I can take on more work and also have the ability to have somebody creative that can run discovery and basically do the creative strategy on things, even better. Right now I'm limited to just me and Andrew Booth being able to fill that role.

2. What happens when Magic Spoon leaves?

$9,500/month. $114K/year. That's roughly 14% of 2025 revenue from a single Shopify retainer. ATS and TAP add another $101K. Three clients, 47% of revenue. You know this is a risk — it's in your docs. But the deeper question is: what's your actual plan if one of them churns in Q3? Not "I'd find more work" — what specific, already-in-motion thing catches you? Right now the answer might be "nothing," and that's worth confronting.

ANSWER: Right now, I'm working with Chris Dubois on a lead gen plan. One of the things we talked about during our last consulting session was that I suck at getting lead gen motions in motion, and his monthly income is tied to the total number of recurring revenue that I have. He is incentivized to grow my recurring revenue by increments of $10,000 a month so that his monthly fee can increase. I've given him some outs because he's been working with me for the better part of a year and a half now, and he's kind of got the short end of the stick.

He didn't use the offer of incremental revenue growth to too many people, so I'm definitely lagging behind on that. During our last session, we walked through a couple of different lead gen activities, including:

• Hero section design
• Guest blog posting
• Guest podcasting

to start getting my name out there a lot faster. I'm also hosting a lot of events in the next few months to hopefully ingrain myself with a lot of my friends here, specifically around the Atlanta area, as well as make some new ones, hopefully up in New York City.

I will say that one of my friends did call me out on this inadvertently, mind you. When I asked him if he knew anybody in New York City that he would be willing to introduce me to, his comment was, "Chris, I'm just trying to win Atlanta right now. I need to be winning Atlanta. I don't need to be winning New York City. I got a lot of people from Atlanta heading up to New York City." In less time, I was able to get 20 people to go to a Topgolf event with me here in Atlanta, and that took no time and basically no money. I need to be winning Atlanta.

3. You've built an operating system for a company 3x this size. Why?

14 MCP servers. Automated transcript processing. AI email intelligence. A vector database indexing your entire communication history. A custom financial planning app. A daily dashboard generated at 4 AM. This is infrastructure for a 15-person agency, and you're running a 6-person contractor collective. Is this tooling an investment in future scale, a competitive moat, a form of procrastination disguised as productivity — or is the building itself the thing you actually love doing? That answer matters.

ANSWER: your callout is actually why I stopped doing a lot of that. I disconnected a lot of the recurring tasks that were happening there. The dashboard thing that you see at 4:00 AM isn't running anymore.

I sat back and thought to myself, "What is the thing that keeps me up at night that I need to have better visibility on?" That finance app is the thing that answered that question. It's the thing that I've been wanting to make for the last five years. I did that, and then I stopped.

Yes, I do have some emails still going up to Qdrent. I have my transcripts getting pulled down, which is still a good practice to have all that stuff stored in one location. I feel like I will be able to utilize that better for reach outs to people and staying in touch with folks as my database of humans expands. That'll allow me to personalize content really well in the future.

The types of automations that we're running weren't actually helping me. They were actually creating a lot more noise. I'm trying to get a lot more thorough with what I'm building so that it actually pushes me in the right direction.

A good example of this is that I created a Starter theme for the company. It has a lot of prebuilt Advanced Custom Field Blocks, predefined Gutenberg patterns, and some Claude scripting. When we're starting up a new site, I can copy and paste that starter theme into a client's repository, and Claude Code will run some automations connected to Figma. It will actually build out the initial version of the site in about 5 to 10 minutes. That will then reduce development time by about 20 hours and allow us to focus our development time on the stuff inside of Figma that looks really weird and that you can't really explain to a robot how to do it exactly. That was time well spent, and I already reaped the rewards of all of that time within the first project. I'm about to use the same setup on a second project now.

The goal is to really, with what I learned through doing all of that (which I think is key to note here), be able to build stuff with your voice without it being bad. It just adds another layer of distraction into the world. We have all these different marketing channels and content that needs to be written, videos that need to be produced, and podcasts that need to be hosted and guested on.

Now the question is, how are you providing 10X more value to your clients overnight? We have the ability to do that in some way, shape, or form. Figuring out where to stop and how to go to bed is critical

4. Can you sell what you're not willing to delegate?

You run 80% of sales calls. You do the design direction. You set the "Classic City magic" tone. The business is Chris LaFay's taste and relationships. That's a strength and a ceiling. Andrew runs 20% of calls — could he run 50%? Could Claude Ball art-direct without you in the room? If the answer is no, then every growth conversation is really a conversation about Chris's calendar, and there's a hard cap somewhere around $1-1.2M (which, notably, you've already hit and retreated from).

ANSWER: the answer to your two specific callouts is yes:

• Could Claude Ball art direct?
• Could Andrew Booth run more technical direction without me?

The answer to both is yes.

For Claude, it's a matter of confidence. For Andrew, it's a matter of him having enough actual time. There's definitely a ceiling for Andrew, given the amount of time he has to give within a given week. Honestly, it probably caps out at about 25 hours a week. That number would not be able to be the average or the default number; it would have to be less than that.

I don't have a person with more scalability at this point. Right now, I'm the only one, and honestly I don't know who that would be. I don't know if I have anybody in my network who is available, interested, and relatively affordable (doesn't have to be super cheap) who could run the creative side for all accounts.

Andrew Booth is the one running the technical side for all of our technical accounts, like Magic Spoon and ATS, and whenever we close Aries, he'll be running that as well. A lot of those things rely heavily on code, and the clients are also very technical, which helps. Andrew does not lead any of the new projects that we close, because those are typically more on the creative and marketing side. Claude could do some of those, but his availability is limited.

Yes, I feel like I'm building an entire company around two folks who can work for me about 20 hours a week, and an intermediate developer in Samson who needs a lot of handholding. The problem is, where do I find that fractional senior person who can run circles around me?

5. Is the agency-for-agencies play a pivot or a distraction?

The $5K "Iconic One-Pager" aimed at agency owners through the Dynamic Agency community is clever. It's productized, it's repeatable, and it solves a real problem (agency websites are embarrassingly bad). But it's also a fundamentally different sales motion than what you do today. Your current engine is relationship-driven, high-touch, $15-35K projects. The agency play is volume-driven, community-based, $5K transactions. Those require different muscles. Is this an AND or an OR?

ANSWER: David Feldman mentioned a very similar thing to me about this. I told him about the entire idea of the agency play, and he said he liked it with one condition: that I only do it for agencies interested in pursuing an actual referral relationship with us.

He doesn't want me getting distracted by small projects like Logan Lyles, and they're not going to bring in more money. What David didn't say was that I need to be more like Andy, who is very focused on the one thing he's doing and is doing a bang-up job with it. He's not getting nearly as distracted as I am.

The only caveat to this in my brain is that if my entire play is going to be building good relationships with agencies over the long term, how can we give them a sample of what it's like to work with us without them having to build out an entire humongous site? I want them to be able to see and feel what that's like without having to hand us over to one of their clients that they have a lot of rapport with

6. What's the real cost of "100% word-of-mouth"?

No ads. No cold outreach. No content funnel that generates inbound leads. Every new client comes through your network. That feels clean and authentic — and it's worked. But your network has a radius. David Feldman, Jack Ogilvie, EO Atlanta, the Dynamic Agency group — these are finite pools. The question isn't whether referrals work (they do), it's whether the rate of referrals matches the rate of churn from legacy clients. Six high-value clients churned in 2025. How many referrals did you get?

7. Is WordPress the right long-term bet?

Your entire technical moat is Gutenberg blocks, full-site editing, and the block library approach. That's a genuine differentiator within WordPress. But the broader market is moving toward headless CMS, component libraries, and frameworks like Next.js (which, ironically, is what you built your own apps in). Are you betting on WordPress because it's the right platform for your clients, or because it's what you know? What would it take to offer the same "block library + education" value prop on a different stack?

8. What would you do with the podcast if it had to justify its existence financially?

"This Got Me Thinking" takes ~~4 hours/week of your time plus editing costs (~~$660/month). It builds relationships with guests, creates content, and establishes authority. But does it generate revenue? If you had to draw a line from podcast episodes to closed deals, could you? And if you can't — is it a marketing channel, a networking tool, a creative outlet, or something you'd keep doing even if the business didn't exist?

9. Jack Ogilvie offered to buy Classic City. What did that teach you?

Someone looked at your business and saw something worth acquiring. What did they see? Was it the retainer base? The client relationships? Your personal brand? The processes? If you stripped away Chris LaFay, what's left to buy — and is that something you should be building more of or less of?

10. What does "enough" look like?

You've optimized expenses down to ~$176K/year. Retainers cover ~$230K. You're at or near breakeven without any project work. If you closed $100K in projects this year, you'd net ~$150K. If you closed $200K, maybe $250K. At what number does the business fund the life you actually want — and are you oriented toward that number, or toward some other version of success that might not be yours?