My notes

Went to Florida for a convention with New York Avenue (Joshua Hays)

Last week I went to Florida for four days (Wednesday through Saturday) and worked a booth at a convention with the New York Ave team. My primary motivation was just to work with another group of people. It sounded like an enjoyable way to spend a few days.

I always point back to my career and realize I have never had the chance to work alongside anybody, especially folks who are farther along than me. I have always been in my ragtag group of people, and that is definitely not a complaint at all. I am very thankful for that, but I did miss the ability, earlier in my career, to sit alongside other smart people and work toward a goal.

I went down there Wednesday, hopped on a plane, and was there all day Thursday, all day Friday, and half a day on Saturday. My initial goal while I was there was to be a front man: try to grab people to come into the booth, say hello, and possibly do a little bit of sales activities as well.

They gave me a download of their entire service offerings, pricing, how they talk about it, etc. That definitely got me out of my comfort zone. Obviously I'm not bad about talking about my services and website building with folks, but having to walk through an entire marketing system that is not my own and that I'm not familiar with was definitely something that was way out of my comfort zone.

It was definitely good for me to do that. As the days progressed, I got more and more comfortable walking up to folks and asking if they were interested in joining me in the booth. As people were interested and I was able to talk to them, I was able to hone how I talked about their productization, and it got simpler and simpler. There were a couple of opportunities where I was able to tag-team some of those conversations with the guys, which was honestly a blast.

In their booth, they had a little mini podcast studio. We pitched this as a way to get doctors or other vendors at the booth to do a profile video of themselves. We asked them about four questions:

• Who they were
• What they do
• Why they love doing what they're doing
• Why they love their customers

One of the guys on the team is going to edit that clip together into a solid profile video for that person.

We had another team member, Ben, there too. His purpose was similar to mine: grabbing folks and seeing if they wanted to do podcast recordings. After the first day, he ended up sitting in the podcast host seat most of the time. I realized the sales angle was probably not my best value that I brought to this team, so I hit up Josh and asked if I could sit in the podcast host chair the next day. He said yes.

On Friday, I tried to spend about half my time in the podcast chair because I think we interviewed upwards of 35 people that day. I wanted to give Ben a break, and that space was a heck of a lot more comfortable for me. A person has already said yes, "I'm interested in being interviewed," so they're coming to that with the idea that they're open to talking about themselves. I was able to prep these people for sales conversations with other team members of New York Avenue.

Built a CMS the past week or so

when I got back, I was chatting with one of my friends, Isaiah Ram, about what all he's been up to, because it's been a while since I've seen him. One of the things he is currently doing is running some advertisements for himself to build some free websites for non-profits and churches ($99/mo hosting fee though). His hope is that by building a free vibe-coded website for these folks that don't have a presence, he can get them into the Google ad grants program and charge them a monthly ads management fee. The website is the foot-in-the-door offer, and the potential long-term retainer bet is helping them with ads.

As he was telling me a little bit about how he was building these things, I realized that every single one of his websites was going to be built very differently from one another. That made me realize that I have this full-blown style guide structure for my websites, and pretty much all of the building blocks in that are blocks built with advanced custom fields (therefore it's custom HTML code that I own, and we're just shoving in values into it). That made me think that if we just use that, we basically have the best possible baseline for a completely custom-built CMS. We just need to wrap it up in an admin dashboard.

With any idea that I have, the only way that I know how to get rid of the idea in my head is to actually build the thing, because that makes sense. I spent the last four or five days working on this. I found an admin HTML and CSS template within the Envato system. I went ahead and bought that for $24 to save a heck of a lot of time designing and building out an admin navigation panel and just general app framing.

I then poured in a lot of the style guide blocks, figured out the whole drag-and-drop thing, figured out the site mapping thing, figured out how to create pages, made it multi-tenant, added media uploads, and did collections of data (like custom post types), literally the whole nine yards. It's not too bad. I mean, don't get me wrong, it's not fantastic or anything, but it's not bad, and it was extraordinarily lightweight. It doesn't take long to load.

It makes me wonder if there is something that I could do with Isaiah where people wanted something more than a vibe-coded site. We actually load them into this thing so that edits are easier, websites are a lot more consistent with each other, and we charge a hosting fee basically.

I realize I get very distracted very easily, and that's one of my core problems. I also feel like building this type of stuff stretches my creative boundaries quite a bit. While I do think I waste a lot of time doing stuff like this, I do feel like there is a benefit to flexing that muscle on a regular basis.

Publicom, TexBuilt, and Trialport

So this is the trio of websites that I basically sold for an average of $15,000 apiece. I'm sad that I didn't actually log my time on the public com and the TexBuilt site, because I feel like my effective hourly rate was close to $500 an hour. It's proving the case that the style guide system and basically Claude workflow stuff that I've done is paying dividends now.

Trial port is the newest one that I'm starting currently. I am logging all of my time on this one, and I'm definitely going a little bit above and beyond on the design side of things because, in all honesty, I have a handful of really good ideas that I want to do with it. They have a really good color palette and structure, good imagery, and I just did the kickoff call today with Keith, the owner and founder of this organization.

He, like many other clients in the past, has said, "If we can knock this sucker out of the park, he knows that there's going to be some other folks lining up for sites like this." I mean, don't go wrong. A lot of clients say that, and do any of them come through with that? Who knows, but he was extraordinarily organized and came to the table with a Google Drive folder of tons of documentation and tons of design inspiration. They're actively writing a lot of their content right now, so I basically have about a week and a half to get their homepage where I want it to be. I feel like right now I'm about at 75%, and I think I've worked on it for about six hours so far, so not too bad. I don't think I'll finish this one in 30 hours flat like I did the TechBuilt public com site, so I'll probably have a slightly lower hourly rate on it, but it's been good.

These clients, the first two, Publiccom and TexBuilt, have been super easy to work with. I basically have sold all these people on the first phone call. I did not send a proposal to any of them, and they basically just signed straight up. Obviously, TexBuilt has some other websites because they're part of a larger parent company that we're working through right now. Publicom will just be a one-and-done, like I doubt I'll ever talk to him again. Trialport will hopefully have something for me and might actually be game to do one of the care packages, which would be fantastic. I haven't had any success with the care packages yet, but I still think it's a great concept.

Relay Scanner

a couple of weeks ago, while I was at the beach, Mickey Mellen was working on a tool called Relay Scanner. You can put in a website URL, and it scans it first to see if it's WordPress or not. If it's WordPress, it has a laundry list of plugins and their up-to-date changelogs. It goes through all of the source code of that website and figures out which plugins are up to date and which ones are not. It also scans for common malware and code injections (the whole nine yards that can be seen publicly), and it puts all of that into a report and gives the website a score.

As he was creating this, I was giving him some feedback and ideas. He created a little portal for me so I could log in, put my own websites in, see the scores, and the whole nine. I asked him to build out an API for it so I could connect it to Claude Code, which he did. I also signed up for a Hunter.IO account so I could find email addresses for these people.

My thinking is I could use it as a good cold outreach mechanism, like, "Hey, looks like there's some stuff wrong with your site." I know from a cold outreach perspective that people don't want the first thing you tell them to be something overly negative. They'll typically just handle that in-house and archive it as spam, so I don't think that's the best route to go with it.

Mickey has also gone the route of helping you find second-degree connections with certain people. He has spent a lot more time on a site-by-site basis to figure out which sites have bad scores and how to find a mutual connection somewhere, so that person can reach out on your behalf to build that connection for them. He has had a couple of clients potentially so far, and I really like this idea.

The thing is, it takes time, and I suck at things that take time. I'm just so bad at it. I get in the weeds doing all the work I need to do and I don't carve out time to do that type of manual lift for marketing. It sucks. Right now, I'm even behind on some of my LinkedIn newsletter stuff, but I've made that really easy for myself, and I just cannot get the motivation to do it. I don't know why.

Questions

The proven engine you keep walking away from

AI Question: $500/hr effective, sold on the first call, no proposal needed. The style-guide + Claude pipeline is proven and printing money. Every side-quest in this note — the CMS, Relay Scanner, even the Florida trip — is you walking away from the one thing that objectively works. What's the story you tell yourself about why the boring, proven engine isn't enough — and is it true?

I mean, I typically always have an excuse for stuff. At the end of the day, that is a very true statement.

The thought here is that the $15,000 website does not produce any recurring revenue, and that's the problem. My thinking is that if I can use the next 12 to 18 months to build a pipeline of folks that pay me between $250 and $500 a month doing something web-oriented, that seems like a very safe bet. Right now, all of my clients pay me in the thousands when they're on retainers, but it's very fragile. I think I only have about five of them at the moment.

How could I alleviate the fact that I have a handful of clients that make up 40% of my income? The idea of having a rotating wall of $15,000 website projects coming in does not sound like a bad idea. I really like that idea, but it also isn't an actual recurring payment from the same person, and I think that terrifies me. If all my retainers go away and the only thing left in my belt is $15,000 website builds, I'd have to sell 1.5 of them per month to cover myself effectively, and that's quite a bit.

So far this year, the cadence has been pretty good. I didn't include every project this year, but we did:

• Consume Media
• Sherman Phelan
• Two from the TexBuilt people
• Lumberock for $25,000 (their process is a lot more intense, so I've basically sold one of these per month so far)

Let me actually give you the numbers so you can do the averages:

• TexBuilt with 17,000
• Publicom was $12,000
• Trialport is $15K
• Lumberock is $25K
• Sherman Phalen is $13L
• Consume Media is $15K
• The State Election Board is $17K
• ASP and Primo was $27K

The diversification you can't see because it's not recurring

AI Question: Updated math: 8 project clients, $141K, ~$17.6K average, ~1.33 projects/month* over roughly six months — on word-of-mouth alone, zero marketing effort. That's ~$23.5K/mo in project revenue, which already exceeds your entire retainer base — and you're basically already hitting the "1.5 per month" number you said you'd need if retainers vanished.*

Now sit with this: that project revenue is spread across 8 independent clients where none depends on the last one existing. Your "fragile, non-recurring" project wall is already more diversified than your 5 retainers that make up 40% of income.* The concentration risk lives in the retainers, not the projects.*

Which means the $250–500/mo recurring dream doesn't actually reduce your fragility — it adds a brand-new product that runs on the one muscle you've openly admitted you won't flex (slow, manual, volume marketing — see your own Relay Scanner note). Meanwhile the project engine runs on the muscle you're genuinely elite at: first-call relationship closes.

So which is really driving the CMS — concentration risk, or that "build a cool CMS" is a more comfortable story than "do the outreach I hate"? And if it's truly recurring revenue you want: what does the version look like that runs on relationships and referrals* (the thing you're great at) instead of cold volume (the thing you avoid)?*

On that note, about the outreach I hate versus the relationships and referral stuff, I haven't done another event since the event with JC Lund in early June. I basically took almost the entire month of June off from doing an event, and I did an agency lunch right after that, so it has truly only been a few weeks, but it feels like it's been a really freakin' long time.

I have a guy named Trey Bowden I'm talking to about doing an event where we might get a space for free or very cheap. We have an idea of how we can get maybe 30 to 40 people in the room for a collaborative workshop-style thing, which sounds fantastic to me. The idea of cold outreach just bugs the crap out of me.

I think the reason I'm not enjoying writing my content for marketing is that it's not a lot of new stuff. I enjoy writing about the things I'm learning about as an entrepreneur, but that's not necessarily just website ideas and things. You could go back as you're reading through this and look through some of my notes from my LinkedIn newsletter and how I want to port that over to email and how I should be able to derive good LinkedIn content from it. I just haven't done it.

What does interest me is writing about this type of stuff: the stuff I'm playing around with, the stuff I'm learning. A lot of it isn't really about the type of website stuff that people would be interested in or is more commonplace. I could write up an entire multi-article set about the CMS I built, even though it's half-baked and not really done and not ready for publication by any stretch of the imagination. Writing about that process would be very intriguing to me, but that's not really what's in the cards. Maybe that's maybe that is a differentiator. I don't know, and I don't need you to agree with that. I'm just kind of thinking that's where my head's at.

There are a couple of other events coming up that I need to put my head toward a little bit. Sophie Brannon said she was interested in co-hosting another Topgolf social event in August. Mickey Mellen's conference is coming up at the end of September or early October, so we need to start thinking about it now. It's getting much closer than I expected.

I need him to approve the artwork I did. Mickey is also interested in doing micro lunches with marketing and agency folks. We have one coming up next week, and I did three outreach emails. One person is interested and trying to clear his schedule. One person couldn't make it, and I haven't heard back from the other. The goal is to keep those extraordinarily small, like six people total: me and Mickey, and then each of us brings two people and splits the lunch tab. I liked that idea, and I think we could do that once a month very easily.

I also haven't done another agency lunch club since I did one in the middle of June. We went to Taqueria del Sol in Decatur and got a good response, with a number of people interested but the date didn't work for them. That is free. Honestly, that is something I should do once a month because people pay for their own meals there. It is an easy way to stay top of mind, provide value, get good social posts, etc. Through that, I also try to push people to bring a friend with them when they come.

Aby Varma also reached out about us bringing content day back to his AI marketing pulse event. That was one that Kiera Wiatrak and I did back in May. I definitely met some good people, but it wasn't the best. I don't know, because there were definitely really good people there. I know some of the people that I didn't get a chance to meet, but I got connected with them a little bit after the fact. They would have been great people for me to know, but they were not the ones that signed up for video slots, so I need to think if I'm going to do that again or not. It's also here in Gwinnett. I know the Shock Social guys would be down for it.

The mic, not the keyboard

AI Question: Simple version. Everything in this note that gave you energy is a live conversation — the podcast chair, the booth, the workshop, the lunch clubs. Everything that drains you is done alone at a keyboard — cold outreach, the newsletter, writing "website content."

So the question is just this: Why are you still trying to market yourself in writing when you're clearly at your best in a room or behind a mic? What happens if you stop, and make "get in front of people and talk" your whole marketing plan?**

This is my whole concept with Content Day. I get 8 hours of space broken into 15-minute chunks, and people come in and answer the questions they've already prepared for us. That is the idea, and that is the way to meet people at scale and provide them value at scale.

If we're doing this from 9:00 to 5:00 in 8-hour blocks, that is 32 slots throughout the day. Obviously that does not include breaks and things, but it is great for meeting new people.

The problem is I do not know how to fill all of those seats. Hypothetically, I could get me and two camera guys there, and if I could figure out a way to fill up that entire bucket, we could rotate folks in and out so that we would all have our own breaks from being on all day long like that.

I do not know how to fill those seats with people that I do not know. That is my problem, because I like the idea of using something like that as an outreach tool. It would really only cost me about $750 to do that all day, but I do not know how to make that scale faster than that. Also, I am going to be limited with cash, because that is going to be probably the thing that costs me the most physical money on a regular basis.

You're solving the wrong problem

AI Question: You said it twice: the problem is filling seats "with people I do not know." But look at the two times this actually worked in this very note — the New York Ave booth and Aby Varma's event. You didn't fill either room. Someone else's audience was already there, and you just brought the chair.* Aby literally invited you back. Mickey's conference is coming this fall.*

So the question: why are you trying to build an audience from scratch when your best moments were plugging your mic into an audience someone else already gathered? What if you never own the room — you make Content Day a thing you bring to other people's events (conferences, EO, partner orgs, Mickey's thing), where the seats are already full?**

And for the times you do host your own: your whole business runs on second-degree referral, and your lunch club already works on "bring a friend." So why does Content Day have to be strangers? If 10 warm people you know each bring one person you don't, the room fills — with warm-adjacent people who convert better than cold strangers anyway.* Is "fill 32 seats with strangers" a real requirement, or a story you invented that makes the whole thing feel impossible?*

the New York Ave thing that I did last week was definitely for somebody else. I did not actually bring Content Day there. New York Ave has a video arm within it, and that's just what they did.

In all honesty, I understand what you're trying to say. The thing is, I just don't know a ton of people that host events. I don't have a lot of partners that do events. Mickey's thing is Happenstance, and Aby Varma was really the first kind of foray into that.

I just emailed Aby and asked if we could get on their registration form for sign-ups, since we weren't able to do that before. That would be great. Bringing it to Mickey's conference would be interesting, but the problem is that his day is pretty full with speakers the entire time, and when there are no speakers, it's lunch. I don't know how we could squeeze that in without pulling people away and looking relatively rude.

The event is relatively small, with about 60 or 70 people there, so if people were constantly leaving the room to go film content, that'd be a very awkward look.

I think I basically just need to come up with what my cadence is going to be. For example:

• Mickey's event is going to be annual, and it's always going to be in October.
• Abby Varma's event is quarterly, so if I could get on his registration form, that would probably be the best.
• I don't mind doing that because I feel like there would be a good number of people there. If we got them to sign up at the very beginning when they registered for it, we could then be picky and choosy about the people that we actually put in the seat.
• If I actually did a monthly agency lunch club, like I started in June, that would be a good cadence.
• If I also did a monthly lunch with Mickey at his micro lunches over in Dunwoody, that would be fantastic.
• Then hosted three top golf-like events with somebody like Sophie.

How do I do the whole microphone thing? You mentioned the microphone. I'm not doing the podcast now. I was doing most of that virtually, and when I say most of it virtually, I did it all virtually, 100% virtually. I'm not really telling anybody any stories of folks that are in Atlanta. The content day video shoots are just one person in front of a camera. It is the person, and then we are asking them the questions that they provide off camera. There's a potential there to flip that around to feel more like a podcast recording, but that would require two camera angles, a little bit more lighting, and my variable cost would increase because there's more editing to be done. Would people actually want to have a video of them being interviewed? I don't know. Right now, all the videos that get publicized are ones where people are talking about themselves and the topics that they want, with no other person

You productized yourself out of the room

AI Question: Catch what you just did. This whole reflection landed on: your superpower is being in the chair, in the conversation. And then you described your current Content Day format — "just one person in front of a camera… we are asking them the questions off camera." You're not in it. You built a version of your own event that removes the one thing you're best at.* No wonder it doesn't feel like a relationship-builder — you deleted the relationship.*

And you already have the proof it should be an interview: in Florida, people said yes to being interviewed and it "prepped them for sales conversations." The interview IS the outreach — 15 minutes of a prospect talking about their favorite subject (themselves), face-to-face with you.

But here's the real fork, and I think it's the actual decision under all of this: you can't have both in one day.* If you're the interviewer in every seat, Content Day is a deep relationship tool — but it's Chris-bound, doesn't scale, and you can't rotate out for breaks. If it's monologues to a camera, it scales and camera guys run it without you — but it builds you zero relationship.*

So the question: what is Content Day's actual job — to build relationships, or to produce content volume?* Right now it's built like a volume machine but you're trying to use it as a relationship machine, and that mismatch might be the whole reason it feels off. Which job do you actually need it to do for your business right now?*