December 15th, 2025

Personal

What did you do today? I didn’t have much personal time today. Content Day ran from before 9am until after 5pm, and once it wrapped, I pretty much crashed. The only personal time afterward was spending some quiet time with Allie once everything was done.

How did you feel about today? Despite being exhausting, the day felt absolutely fantastic. It was deeply energizing to spend time with 14 people one-on-one and provide them with meaningful value. I was tired in the best possible way.

Work

What did you accomplish today? The single focus of the day was executing Content Day — and it was a success. Working with the Shock Social video team (introduced by Rod Hames) was a highlight. They were professional, kind, thoughtful, and went above and beyond to make everyone feel comfortable. I trusted them completely with people I care about, to the point where I felt confident handing participants off and not even being in the room. That trust paid off.

What did you learn today? I was reminded how energizing it is for me to give to people — not just creatively, but by taking on the operational risk and responsibility of putting something meaningful together. I genuinely enjoy the logistics, planning, and ownership when it’s done intentionally.

I also learned there is strong demand for this kind of value. Three people expressed interest in doing something similar with their own audiences, and I’m already scheduling conversations to explore collaborations. Each of them serves an audience that aligns well with people we can build websites for.

At the same time, I noticed a quiet drain: playing host in a highly fragmented way throughout the day. With 16 thirty-minute slots running back-to-back, I was constantly juggling greeting the next person, easing the previous person out, and trying to connect with both. I realized I’d prefer to spend time with people before their session to get them comfortable, rather than scrambling afterward. There are opportunities to redesign the structure to better support that.

Did you meet anyone new? Yes.

• Wayne Pelletier, founder of Resonant Pixel, who builds Squarespace websites. He was the first person to record and I met him through the Bureau of Digital.

• I reconnected with Keith Williamson, a friend of Adam Walker’s who I originally met at Brighter Web Conference in October while he was job searching.

• I met Brian Jungles, who runs a publication company. He was especially excited about Content Day and expressed strong interest in following up — I should schedule time with him.

Family

What did you do today? Very little family time today beyond spending time with Allie after Content Day wrapped. The day was fully consumed by the shoot.

Deeper Reflection

What energized you most — and what quietly drained you? Giving to people is deeply energizing for me. I love creating opportunities others wouldn’t normally have access to and seeing their excitement when they step into something meaningful. I don’t mind the operational work or the risk of hosting — that part actually excites me.

What drained me was the scattered nature of hosting. Constantly bouncing between greeting arrivals, transitioning participants, and trying to connect meaningfully created friction. I want to rethink the flow so I can build rapport before people go into the recording room instead of scrambling afterward.

What would need to change for Content Day to be sustainable long-term? Running Content Day monthly in its current form would require rotating locations across Atlanta and addressing cost. This run cost $1,200 ($500 video, $700 location), which is fine as marketing spend — but not indefinitely without leverage.

I need to decide where this lives on the spectrum between marketing and monetization. Options include partnering with agencies and charging them $10–20K to host Content Day for their audiences, or keeping it lightweight and free as a recurring marketing play. The real opportunity lies in tapping into other people’s audiences while maintaining the spirit of generosity that makes this energizing for me.

December 17th, 2025

Personal

What did you do today? Allie and I went to the Kriskindal Market in downtown Lawrenceville with our friends JC and Mary this evening. We shared dinner and drinks and spent a couple hours walking around and hanging out with their kid, Ransom. I also went to Crews Middle School where Rod Haynes was hosting a Shark Tank event for his eighth graders, and I worked with six different students on their business ideas.

How do you feel about today? Today was an overall good day. I did a solid job balancing work and personal life.

Work

What did you accomplish today? I had a sales call with Wayne about his ChurchProducts.com e-commerce site, which feels likely to move forward starting February ’26. I talked with Kale, a friend of Jared Belsky’s, about a potential $12,000 website project that may move ahead soon.

I also connected with Sophie Brannon of Studio Hawk about partnering on a CMO Roundtable. We already have a meeting scheduled and are aiming to host the event in April.

I spoke with Andrew Eklund about TANTAN, an agency connection organization similar to Entrepreneurs’ Organization, focused on honest advice and peer learning.

The day wrapped with a planning call with David Rees to lock in dates for the New York Exude agency leaders field trip in early April. Dates are confirmed with our significant others, and I’m now building the landing page, which I need to finish this week.

What did you learn today? I’m already seeing interest build around the Content Day I hosted earlier this week. Conversations about bringing people together and producing video assets confirmed there’s real demand. The challenge now is format — the current structure could get stale quickly if I don’t evolve it.

I also talked with Jon Durden about potentially monetizing Content Day and turning it into its own brand. Since I already have videographers producing strong work, there may be a path for it to pay for itself or even generate consistent revenue. I’m still deciding whether that’s something I want to pursue and what shape it would take.

Did you meet anyone new? Isaac Hong — a 9th grader at Brookwood High School who helped guide the 8th graders during the Shark Tank event. I was impressed by how thoughtful and confident his questions were. At that age, I wouldn’t have been comfortable being on the other side of the table like that.

Family

What did you do today? The only family-related activity today was going to the market with Allie, JC, and Mary.

Deeper Reflection

What actually moved the needle today? While the sales calls were productive and need follow-up, the most meaningful long-term momentum came from conversations around creating new events for next year. One of my goals is to host or co-host one event per month, and I feel on track. I’ve already scheduled January meetings to keep that momentum going and believe it’s possible to host three or four events in Q1 if those conversations go well. My biggest concern right now is keeping track of all the active deals and opportunities in my pipeline without dropping the ball.

What would need to be true for Content Day to become its own brand? I’d need a video partner willing to absorb risk with me — ideally through profit sharing instead of guaranteed minimums. That partner would also help with locations, editing, and continuously evolving the structure and style of Content Day so it doesn’t stagnate. I want to move beyond simple 30-minute talking-head sessions and experiment with more dynamic formats and scheduled sign-up slots. Jon Durden’s comment stuck with me: this could become a consistent monthly revenue stream if I put real focus behind it.

December 18, 2025

Personal

Yesterday I hung out with Claude Ball and had dinner with him. We were down at Good Word Brewing, and we just hung out for a few hours talking about everything from how to design better to how to grow. One of the main things we talked about was him thinking about adding some messaging components into what he does, and we also talked a lot about solo travel. Overall it was a very relaxing time.

Business

Work-wise, I recorded a podcast episode for This Got Me Thinking. After that, I spent a few hours recording custom intros and outros for every single episode I’ve recorded that hasn’t been edited yet. So I was able to hand my editor, Patrick, about eight episodes where—if he has time over the holiday break—he can basically run straight through them. He was really excited about that, and he feels like he can get all of them knocked out and ready to go within the next few weeks.

I also worked a little bit on the pricing calculator, and honestly I need to stop trying to make that thing 100% perfect. I think I have it almost done. I’ve got it to where it downloads a PDF version when people are ready for it. I think I just have to tighten up the PDF a little bit and make sure it emails me so I know somebody actually used it. Once that’s in place, I feel like I can put it on a couple different pages of the site, start testing it, and then honestly start writing some content about it too.

I also met a person named Alex Foulkes—the person I interviewed—and Andy Milligan is the one who introduced us. Alex runs a business operations company. He helps creative people who run businesses but suck at operations… like actually running them well. Not just admin stuff or finance stuff, but project management, staying in touch, and basically all the things that visionary types tend to struggle with. It’s a really interesting business model that I honestly hadn’t thought about before.

What I Learned

Yesterday reminded me that I need to schedule more days where I don’t have nearly as many meetings. I felt like I accomplished quite a bit because I could sit down and focus. I also need to figure out a better way to organize my task list because there are probably one or two things I should’ve gotten done yesterday that I definitely didn’t—because I went so hard-nosed on podcast intros/outros and prepping all of that. And don’t get me wrong, that was a good use of time, because now I don’t really have to think about it anymore.

Also… if I could just find somebody to upload the podcast for me, that would be fantastic. You’d think a simple 15-minute task would be easy for me to do, but it never is for whatever reason. I don’t even know why.

Family

Allie went out and hung out with Sarah Reiss last night and did her first-ever book club with her. She really enjoyed it—there were about five other women there—and she liked the conversation a lot. She also started playing Baldur’s Gate again, and I think this is going to be her fourth run-through, so she’s very excited about that. And I finished up a lot of the manual labor portion of her Christmas present yesterday, so now I just need to put it all together.

Deep Dive Questions

1\) You got a lot done once you had space. What’s the non-negotiable calendar rule you need next week—and what’s the one thing you’ll say no to to protect it? I’ve been getting pretty decent at not scheduling meetings on Fridays. With the business changes—moving Daniel and Dawn to part-time—I’ve had an influx of sales-related activity, which I’m honestly really happy about, but it’s pulled some Fridays into being busier than they normally are. I’ve put some sales calls on Fridays just to keep the ball moving, because I need revenue coming in the door starting in January. Friday is today though, and the only thing on my calendar is a two-hour jam session with an agency owner I know, which honestly will be a fun, creative way to spend time.

I tried to block time on my calendar for podcast recording, internal virtual meetings, and then “out of the house” meetings—like only doing in-person things on Tuesdays, and doing virtual connections on Wednesdays and Thursdays—so I could protect focus time. That hasn’t worked super well, mostly because I feel like I need to be in a mode where I’m meeting as many people as possible right now. I like the idea of no meetings before noon… but that’s going to be a challenge.

2\) The “15-minute task” problem keeps showing up. What’s the real blocker—and what’s the first delegation experiment you’ll run? I don’t think the blocker is perfectionism, lack of a checklist, or control. I think it’s just hard for me to know that a “10-minute task” is actually going to take 15 different steps, and I have to wait and be patient while it gets done. For whatever reason, there’s a mental block there. I would love to delegate it, but part of this new version of the business is that I need to take on ownership of some of these things and actually do them versus shipping them out—mostly because of cash.

I asked Patrick yesterday if he’d be willing to do uploads if I paid him a smidge more, and he categorically does not do them because it would require him to have a bazillion Google profiles logged in, which is a total pain. I don’t have a VA right now, but when I do, podcast uploads are probably one of the first tasks that comes off my plate.

December 19th, 2025

Personal

What did you do today?

Today I worked a little bit on my final D\&D session preparation. Tomorrow is my last D\&D session that I'm hosting through this mini campaign. My players are about to fight the big boss battle, and I prepped the map, the big bad guy, and also some of the various different story points that they could have. I enjoyed the idea of being the DM for a D\&D campaign. I enjoy a lot of the prep and the setup work. However, I am a serial procrastinator, I have found out. And I tend to wait to the very last minute to actually do any of the prep work which is extraordinarily stressful.

So what I have found out that I do like is basically creating the math and the challenges behind various different dungeon crawls as well as making battles unique and interesting and different. And so I would love to see when Allie is running her campaign how I could possibly help her build out some unique dungeons or crawling through different places and allow her to utilize those wherever she sees fit.

How did you feel about today?

Solid is my one word. Allie and I also got to hang out and watch a movie tonight which was fantastic and go to the gym today. I also feel very prepared for the D\&D session tomorrow. So overall personally I feel pretty solid.

Work

What did you accomplish today?

I spent a couple of hours working on the pricing calculator for the website today. I nailed down the PDF output as well as finally got it to actually email me a copy of the output as well.

I then spent some time talking to Mickey Mellon about the changes that are upcoming inside of his business. We talked some about that as well as some of the event preparation for this coming year. I told him I wanted to do more of these content days and I walked him through a little bit more about how content day actually went. He was very excited about it and I basically pitched in the idea of having content day be a part of the brighter web ecosystem. This is kind of opening up my eyes on how me and him could partner up together to build the brighter web community and how we could make our events larger together. I'm hoping that over the course of this year, that maybe I could actually host some of these content days through brighter web and start building that community up some. This would allow me to host some more events and very naturally tap into that community. I'm very interested in that.

What did you learn today?

My call with Mickey today was primarily supposed to be with or about the challenges that he was having. I found out today that when I was chatting with him, he pretty much had everything kind of locked and loaded and prepped and ready to go. So we ended up taking the conversation a different route. I do feel bad that we scheduled this meeting with him, me, and him to go over all of his stuff, and we ended up talking about more of my stuff. But I also know that Mickey, in and of himself, is a very interested person, so he asked a lot of questions no matter what. The conversation naturally floated away.

The other thing I learned today is that project management bothers the crap out of me. We are in the process of finishing a mini project for a client called APEX, and Dawn was not on the sales calls or the discovery call or anything like that. She is a little bit lost in project managing it, which I totally understand why. It makes me feel annoyed, but I also know that that's not the right feeling that I should have. So I need to figure out how do I move things from sales to project management better so that I don't get annoyed at stuff like that. If it's something that I truly do not enjoy, I need to figure out how to get it off my plate entirely.

Did you meet anyone new?

No.

Family

What did you do today?

Allie and I went to the gym today in the afternoon, which was an extraordinarily tough class over at Orange Theory. We came back home, we made some Mediterranean bowls with couscous and sausage, and then we sat down and watched the most recent movie in the Knives Out series on Netflix. It was a very relaxing evening, a great way to conclude the week.

Deep Dive Questions

Where in my life am I unconsciously recreating situations where I get to be the architect but not the inhabitant—and what do I gain by staying in that role?

When I stay inside the architect role, I basically just chase my tail. I keep creating new things over and over again. I don’t like working within the things I’ve already built because once they’re no longer new, they’re not as exciting.

A really clear example of this is to-do list applications. Whenever I start using a new one, it’s empty. It’s blank. It’s a clean slate. And that feels really good. But once it starts to get cluttered—or once I get busy—I start to ignore it. It’s no longer new anymore. So then I feel the pull to create something new again just to make it feel nice and fresh.

I don’t get nearly as much joy from seeing a body of work accumulate over time—getting to the point where I can look back and say, “Man, I’ve used this consistently for years, and look at where I am now.” For whatever reason, my brain immediately goes to whatever the newest toy in the box is, and that becomes the most interesting thing.

And the truth is… it’s very hard to run a business that way.

What part of me resists closure and delegation because it equates “finishing” with loss of identity, relevance, or control?

I think what you’re seeing right now in these journal entries around delegation is mostly a lack of money to actually spend on delegation. That’s the practical reality.

But if I tie this back to my answer about not using old tools, there’s another layer: I’m really bad at pre-scheduling things early so I don’t stress about them later. There’s always something more urgent to do, and those urgent things always float to the top of the list.

I know there’s the Eisenhower Matrix—urgent vs. important—and I don’t even remember all the quadrants anymore. But I do know this: I spend most of my time reacting to anything labeled urgent. Phone calls. Slack messages. Scrolling LinkedIn. Especially on the business side of things.

And in this particular season of the business, it genuinely feels like I need to spend every possible moment moving the needle. I know my team members’ availability is about to shrink, and I feel pressure to use them while I have them.

On top of that, every sale feels extremely important right now. Some of our retainers aren’t necessarily in limbo—but there’s always that low-level stress sitting in the background: When will this be the last month for certain retainers?

And I know that’s not a healthy way to live.

December 20th, 2025

Personal

What did you do today?

Allie and I started the day by getting coffee at Seven Brew, which is our typical Saturday routine. I ran a few errands in the afternoon before hosting the final D\&D session for my mini-campaign. It was the big boss battle, and I had designed about four or five different endings depending on how the dice rolled and what choices the players made. I confirmed beforehand that they were okay with any outcome, from the best to the absolute worst, and they were game for it. The session lasted about four hours, and everyone was super excited; it went very well. I definitely procrastinated more than I should have on the prep, but that’s just how it goes sometimes.

Through this, I've realized I enjoy being a Dungeon Master, but I don’t particularly like the improv side—creating and roleplaying a bunch of NPCs isn't for me. However, I love building dungeons and boss battles, and I want to find a way to craft more of those over time because it’s just a lot of fun.

To end the day, I went to David Feldman’s 40th birthday. He rented a sauna and a cold plunge, and I joined seven people I didn’t know at all. Jumping into a sauna with strangers was wild since I’d never done it before, but it was an enjoyable experience. The cold plunge wasn't as bad as I expected; apparently, it’s easier after being in the sauna, though I don’t quite understand the science. We cycled through the sauna and cold plunge for about an hour, then ate fantastic Korean barbecue that David prepped. I found out a lot of the guys there are legit musicians, which was dope. We talked a bit about D\&D, and then played a few rounds of Wavelength. It was a wonderful day, and I finally got home around 11:30 PM.

How did you feel about today?

It was a really good day, and I very much enjoyed myself. It involved a lot of social interaction, between playing D\&D and then going out to hang out with people I didn’t know at all. Because of that, I was absolutely exhausted by the time I got back home, but it was definitely a day I would absolutely repeat again.

Work

What did you accomplish today?

Honestly, for work, I did not accomplish anything at all today. I don’t think I had any work-based conversations and did absolutely nothing professional. Today was purely a recharging day.

What did you learn today?

Even though I didn’t work, my experience with David was a great reminder to just try new things. As soon as I hopped into the sauna—I was probably only the third person there—David asked, "You've never done this before, right?" and he was 100% right. This whole day was really the culmination of trying new things: finishing the D\&D campaign was the end of my first run as a DM, and hanging out with David’s friends was a brand-new experience. Meeting so many new people at once was part of that, too. I learned that trying new things and getting out of your comfort zone makes other difficult tasks easier in the future. The more hard stuff you do, the easier the next challenge becomes.

Did you meet anyone new?

I met seven new people at David’s birthday party. I have all of their phone numbers, and I’m actually in a group chat with them now, but I honestly don't remember any of their names or how they are specifically tied to David. They aren't necessarily people I need to keep up with from a business perspective, but it was great to meet them.

Family

What did you do today?

I didn’t do anything with family today outside of the personal activities I’ve already mentioned, like our morning coffee routine and spending time with Allie.

Deep Dive Questions

You mentioned that you love building the "dungeons and boss battles" but dislike the "improv and roleplaying". If you look at your business through that same lens, what are the "dungeons" you enjoy building, and what is the "roleplaying" that is currently draining you?

I enjoy building systems for operations. I realize that I end up spending a lot of time creating spreadsheets, calculators, and new elements for the Classic City site; I'm a creator in that sense. I recently created a product called "The Prototype," which is a two-week design-only sprint to let clients test-run working with us. The creation of that product was a lot of fun. I enjoy getting into the weeds of the business and the creative deliverables, and I love working with clients to get to the root of a problem.

However, while I like creating operational structures, I do not like running them. I always want to be tweaking them. I need to get better with consistency—creating the system and letting it run without complaint. I know that sitting purely in a sales-only role is not where I’ll thrive long-term, but I also don't want to be doing the heavy technical deliverables like coding. My business is moldable right now because my payroll is about to drop significantly, and I’m considering shifts like turning Classic City into a design-only agency or partnering with friends on creative consulting.

You’ve now proven—both with Content Day and the D\&D finale—that you can deliver high-value, high-stakes experiences even when you procrastinate on the prep. Does that "last-minute" pressure actually serve your creativity, or is it a hurdle you want to clear to make these wins feel more sustainable?

I think my procrastination is a bug, not a feature. With Content Day, I didn’t actually procrastinate; I just set an extraordinarily tight deadline, which made the pressure external. Once the date was on the calendar, I had to do it. I phased out the work over two weeks and didn't feel rushed, only forgetting small things like name tags.

The D\&D campaign, however, felt like external pressure but without the same "reality" because it was a personal goal. I kept telling myself I could just do it tomorrow, thinking I could knock it out in a couple of hours, which wasn't true. I’ve realized that external pressure forces me to work at a more even pace, but I haven't quite figured out how to apply that same pressure to myself internally for goals that don't have an outside audience waiting on me.

December 21st, 2025

Personal

What did you do today?

Today is Sunday, and we went to church as we normally do. I played drums this morning, and the entire worship band experience went very swimmingly from a musical perspective. After church, Allie and I came back home to relax for a while. She started a new Baldur’s Gate 3 playthrough, and I spent some time reading Project Hail Mary by Andy Weir, which I started about a week ago.

Later in the afternoon, we went on a double date with Mark and Kendra Barneycastle. We ate at Jerusalem Bakery in Alpharetta and then went to see a live Christmas jazz performance at The Velvet Note. This was the first time most of the group had been to a jazz club, and it was an absolutely fantastic experience. The piano player, William Green, and his band were a 10 out of 10; I’d love to see him perform again. Allie really enjoyed it as well, and we’re already thinking about going back more often next year. Even though the show was only about an hour and a half, it felt much longer because the music and vocalists were so great.

As a drummer, I found the improvisation and the connection between the musicians fascinating. The pianist acted as the band leader, guiding the bass player and drummer with subtle hand motions, facial expressions, and head nods. Watching the band respond to those cues and change their playing in real-time was incredible. They had a connection that made it seem like they’ve been playing together for years.

How did you feel about today?

Today was an extraordinarily relaxing day. I could have sat in that jazz club for three or four hours and just been in seventh heaven. Listening to live music in a small venue like that is an extraordinarily relaxing thing for me; there's just something about the quaintness of sitting right on top of the stage. There is a level of human connection there that you don't get at a large standing-room-only concert. It was a fantastic experience and a great way to end the weekend.

Work

What did you accomplish today?

The only work-related thing I accomplished today was moving around some meetings for next week that needed to get pushed out to the new year. Nothing too crazy. I did notice that Andrew Booth sent over a project update for ATS regarding some requests they made late last week. I’m really happy we were able to knock those out so quickly for them; it should set them up very well for a meeting they have tomorrow morning.

What did you learn today?

The jazz club was another new experience, and it was interesting to have this plethora of new things happen back-to-back. Saturday was packed with novelty, and then today added a new restaurant and the jazz club to the list. This entire weekend was full of new things, which was a lot of fun. It reinforced the idea that I need to just continue getting out of my comfort zone.

Did you meet anyone new?

I did not.

Family

What did you do today?

Allie and I went to church together this morning and spent the afternoon relaxing and reading. Later, we went out on a double date to Alpharetta for dinner and a jazz show. My dad gave me a call on our way back home from the jazz club to figure out our Christmas plans. It’s a bit complicated because of the situation with my brother, so I just told him he and I would swap presents a couple of Mondays from now since we weren't invited over for Christmas. Thankfully, the conversation wasn't awkward or lengthy, which was fantastic.

Deep Dive Questions

You observed the jazz band leader guiding the musicians through subtle cues like head nods and hand motions, noting that they were "all on the same page." As you navigate the next few weeks with your team members' availability shrinking, what are the "subtle cues" or systems you need to put in place so your "band" stays on the same page even when you aren't in the same room?

There are definitely going to be some hitches, primarily because Dawn has been picking up anything she can over these last few weeks while she was full-time. I know there will be areas with certain projects popping up where she won’t feel she has the flexibility to do quite literally anything she wants, simply because she won’t have that full-time salary. I’m thinking there will be some issues there at some point, though I don’t know exactly what those will look like yet.

The good thing is that we have very good clarity on what her pay structure looks like for next year with the projects we have active—not just in the pipeline, but actually active. Her pay will immediately drop down to about 30% of what it currently is, so I am a little bit concerned with that transition. However, over the last month or so, our retainer projects have all gone well. She’s getting paid the same amount of money for those and working the same number of hours, so that part shouldn't change. I'm not too terribly concerned there.

Looking back at Content Day, which was also an intimate, one-on-one experience, how does this weekend’s "human connection" insight change how you think about the future format of those events?

It’s all about creating memories in some way, shape, or form. Doing David’s birthday party was a new experience, and going to the jazz club was a new experience. If there is a way to create memories at scale like that, that is going to be the big win.

With the way we did Content Day this past time, I don’t necessarily think it was memorable beyond the fact that people got an immense amount of value from it. As I’m thinking through ways to provide value to my friends at scale so I can stay top-of-mind, if I can pivot that into creating a unique memory, that’s where the long-term win will be.

I’ve been thinking about hosting cocktail hours at my house, doing larger group sessions, or hosting roundtable discussions recorded with a small group of people who don't know each other. There are a handful of ways to do it, including simply going places with folks—like a jazz club—and being intentional about getting 7-8 people together. The goal is to build an intentional community where people are encouraged to invite new faces. One of my agency friends has noticed their events stagnating because the same people keep showing up. There needs to be intentionality from the beginning about bringing in new voices. The key pieces I want to dig into over time are: How are we creating memories, and how are we always inviting in new people?

December 22nd, 2025

Personal

What did you do today?

Today, Allie and I actually went ahead and celebrated Christmas. We typically always give each other our gifts way before Christmas just because we already have them and there's no reason to wait any longer. So we went ahead and exchanged gifts which marks the end of my preparation of Allie's extraordinarily convoluted Christmas gift where I got her a million different things for her next D\&D game that she is running. I manually cut out hundreds of pieces of cardstock with various different map pieces, a lot of different elements for like treasure chests and rocks and things that I also manually cut out. I ended up purchasing some 3D terrains as well as also some like 3D printed rocks, sticks, boulders, and things. I also got her a roll-out map set so that she can make the entire table look like a particular terrain and then she can place the cutouts on top of that to make an even more immersive experience. I got her some castle walls with doors and some crumbling areas as well. I got her some new status indicator rings that stack up very nicely, and so now that is done\! She was absolutely beside herself with excitement with it\! It took me the better part of two hours to physically wrap the rest of her gifts, get stuff inside of her stockings, and then prep the rest of the closet the rest of the way, so that is done, and she is thrilled\! I also read a little bit more in Project Hail Mary by Andy Weir; I'm actually a little bit over halfway at this point, so yay for that\!

How did you feel about today?

Today was a really good day. I ended up spending a good amount of time on building out this style guide/wireframe tool for myself. It's something that I build out in Figma currently, but would love to have the ability to do it inside of a browser so that the style guide is very tangible, can also add elements to it very easily, and then be able to show that live to a client and be able to have them click around and "touch" the website, for lack of better terms. Then also potentially building out some type of an export tool from it so that it will automatically create custom blocks within WordPress for each of the different elements that I have in there, and so that'll just save multiple steps in getting into development a heck of a lot faster. So I spent time doing that. I don't know if it was necessarily worth the time. Obviously I did not finish it, but my brain is buzzing with creativity at the moment, which is a very exciting place to be but it's also a very hard place to focus on.

Work

What did you accomplish today?

I met, I think for the first time, a woman named Allison Boaz who honestly just wanted to get together, connect, and chat about random stuff. Found out that she's actually from Atlanta, and I'm going to invite her to the next Content Day that I host. She is a fractional CMO, so she would probably be a good person as a fit for the podcast at some point as well. There was no sales pitch, no pitch—we talked about the stuff that each of us did, but it was a very chill conversation which was fantastic.

Then I talked to Apex Trading because we went ahead and passed over the site for them to start working on content. The guy that is going to be working on it was a little bit flustered because I don't think he's ever edited a WordPress site before, so I sent him on his merry way with all the various training videos and hopefully he'll have minimal questions. This is the downside of doing a website build and not doing any of the content; it's always that shock reaction, so we need to figure out a way to reduce that element because I'm feeling we're probably going to be doing a little bit more of that in the future.

Lastly, I worked on that style guide tool. It's very interesting. I like it, if I could figure out a way to make content around it. There's just thoughts I have about taking some of these tools and ideas and putting them under an umbrella, writing content about why I decided to build them, the building process, the iteration process—the whole nine yards. But the thing is, I don't know if I want to spend time editing all of that because there's going to be a lot of just video of me writing AI prompts. I don't know if there's value in that "building in public" space or if that's in alignment with this. I'm not 100% sure, still trying to figure out the way that I want to stand out.

What did you learn today?

I'm realizing that if you're a developer and you understand the core concepts of how to code, and you're also a visionary where you have a lot of ideas just coming out of you day in and day out, AI is not a thing that really helps with concentration. When you can go from an idea to something that is fully fleshed out at like 50% in the matter of a couple of hours, it's a really addicting thing to a creative person. When you get that itch to do something new and to try something and to build something, you're like, "Oh wait, I can do that right now." And then at that point, everything else is lower priority, and all you can focus on is that one thing.

So I have to figure out how I am going to not get distracted by trying to build every single idea that's in my mind? Because I can, and just because I can does not mean that I should. I don't even take these ideas and vet them to other people to make sure that I'm not barking up the wrong tree. I'm just building stuff that's in my head. And I'm sure the code is not that great at the end of the day; I don't really have an eye on how everything is being built from a foundation. Their infrastructure is probably extraordinarily weak, and that does terrify me a little bit as a person who builds websites in general. I'm seeing all these places where I can expedite operations, but I feel like these things I'm doing are probably trying to take some piece of operations and improve it from 85% efficient to 88%. Those jumps don't matter. It's taking something from zero to 50\. And I need my creative brain to think more on those areas and also how it impacts generating new leads as well.

Did you meet anyone new?

Yes, Allison Boaz.

Family

What did you do today?

Other than the gift exchange that Allie and I did today, that was pretty much the only family stuff that happened. We typically always give each other our gifts way before Christmas. She was thrilled with the D\&D terrain setup I put together for her.

Deep Dive Questions

Where in your current "buzzing" list of ideas is there a "zero to 50" leap for lead generation, and which ideas are actually just "85% to 88%" operational distractions?

There is not an idea that I have that's taking something from zero to 50 inside of my head at the moment. I know I'm about to drop the ball on posting things on LinkedIn, and I've already dropped the ball the last couple months on sending out emails on a regular basis. I don't know what I need to do to make that a more efficient mode of marketing. The only reason I was as consistent with LinkedIn the last month is because about a month ago, I had a day where I was able to sit down and literally just knock out all the content, which is fantastic. I'm wondering if there are ways that I can take all of my previous LinkedIn content, any blog posts that I've written, all of these entries, my sales call transcripts, my meeting call transcripts, my podcast transcripts, and basically put them all into some sort of a folder system and have AI go through all of that and take the themes and core topics of my current LinkedIn post history as a baseline for my tone of voice, my structure, and the topics I'm interested in, and pull out different derivatives from all that type of stuff. Like that would be a very, very powerful thing to have at my disposal. And then also figure out how that would then convert into email content and things like that.

You mentioned that the "weak infrastructure" of these AI-built tools terrifies you. How does this fear change the way you view the value of your agency? Does the value lie in the "code" itself, or in the "architectural vetting" and "human connection" that AI currently lacks?

I think one of the big pieces of the value proposition of our agency is definitely going to be the personal connection side of things. The idea for Content Day is fantastic, and the need to extrapolate on that quickly is important. I don't have any off-the-cuff ideas of how to grow that exponentially super-quick. I also have a couple of ideas with working with Chris Dubois about doing a virtual agency summit as well, which would then let me tap into other people that I know across the spectrum and getting that kicked off at some point in April. All of these things seem slow, which is fine, but it's a good time for me to get started. Where I feel like there's a lot of pressure on that. And when we have those large retainers, it's a lot simpler to have full-time employees obviously. So I'm wondering where the line is. I'm watching Andy Milligan who is starting to get some success in the healthcare niche because he's niching down into that specific people that he knows are able to send very direct referrals his way. People are able to look through their client lists and see “oh yes, this person needs what you do”. So it does make me kind of go back and think about the value proposition of my agency as “is there a value that I could provide to a very specific subset of people?”, which I know is the problem I've been trying to solve for a really long time.

December 23rd, 2025

Personal

What did you do today?

Honestly, from a personal standpoint, I didn't do too much today. I mostly did work stuff. I ended up practicing piano for about an hour and a half or so tonight because I will be playing piano for our Christmas Eve service at church. I'm very excited about it. It's definitely stretching my boundaries a little bit because we're playing a lot of songs that I have never played before. But I practiced them quite a bit the last week or so, and I feel honestly pretty comfortable with it. I'll be playing all these songs live with our band leader for the first time. We actually haven't practiced yet together which is a little bit annoying, but you know, such is life. It's kind of my entire musical journey which is learn music and play it live almost the first time every time.

How did you feel about today?

It was overall a very relaxing day. From a personal standpoint, it was a very energizing day today, and I definitely do not feel overwhelmed right now, which is a great feeling. But I also want to make sure that I don't get super creative and dive down too many rabbit holes and get distracted.

Work

What did you accomplish today?

Today I got together with John Durden and honestly worked with him almost all day. He is a member of my EO group and he had been talking about how his website was a stumbling block for him to get started with lead generation for his business. So I offered to sit down with him one day and basically go through his design inspiration, wireframing out key pages as well as site mapping what he needs in preparation for his work with Andy Milligan. And so we spent the better part of four hours today going and doing all of that. And I realized that I very much enjoyed that particular process. I enjoy hanging out and poking holes in things because honestly, I can get to the crux of the core of what's needed for a website within the span of a few hours. It's not really that challenging for me.

And so what I also did today is talking about all this design inspiration and things along those lines with John made me realize that I do enjoy the design process. So I went ahead and purchased the Radical Design course by a guy named Jack McDade. And ended up spending way too many hours tonight looking into that. And so that was a lot of fun, and I have an itch to design something super creative for somebody right now. So don't know when that's going to end up being, but or even if I will actually do it, we shall see. But I have a lot of tools at my disposal now and a lot of motion for being super creative with it. And so I don't know what it'll look like. I might maybe toss something out on LinkedIn and see if anybody wants a homepage design without any kind of holds barred basically. Pitch something like if you're willing to let me take the design reins you want to do something kind of creative and small? Let me give it a shot and see what happens.

What did you learn today?

I'm definitely learning that I think my sweet spot in the business is not just simply doing sales. I think there's an aspect of what this business could be where I am directly doing consulting and that I actually enjoy that. When I was chatting with Mickey Mellon the other day, I know that he's probably going to be doing something similar as well too. And I want to be okay with that and I want to be able to make money for it. So now that I've done this for both Chris Dubois and John Durden, I want to figure out where I can basically try some of this out, this design consulting thing out. I know that Anil Gupta is looking for something at some point here soon for the design of his website. And I know that he is willing to pay so I'm wondering if that's kind of actually the first one that I do.

Deep Dive Questions

You mentioned that getting to the crux of a website's needs in four hours "isn't really that challenging." If the thing that is most valuable to your clients (clarity and a roadmap) is the thing that is easiest for you, how does that impact the "Classic City" model for 2026?

I think this goes back to the prototype offer that I worked on a couple of weeks ago—that two-week design sprint thing. I’m wondering if this would be a good example of that. I have the What’s In project in my pipeline, and while I’m not sure if their style and texture are going to be super odd and interesting yet, I wonder if I can get them to think outside of the box a little bit. Honestly, if I can do more of that type of stuff where we have a handful of retainers that keep our core team busy (so I don't lose them to other more full-time jobs), and then I can close one or two of these small design consulting things every month—like a $10,000–$15,000 project—that would almost be perfect.

The "Radical Design" itch is a classic creative high. How can you use that "homepage design" LinkedIn offer as a lead-gen experiment (a "Zero to 50" move) rather than just an "85% to 88%" creative distraction?

I know that Chris DuBois has been asking me about what type of testimonial that I want him to give me. I know that he is willing to basically do whatever I would like to for his testimonial. So I'm wondering how I can position this new offer kind of simultaneously with Chris' testimonial. I also need to get one from John because he said that these four hours that we spent together, even though we didn't actually do any design work, was an extraordinarily beneficial four hours that got him out of his head. A lot. And so I'm wondering, both of these people are agency people. I mean, Chris runs a community now, but he's a former agency person. John runs an agency, so I'm wondering if there is a way to pivot this to agencies specifically and being like: "Hey, let's take your website from something that is holding back your marketing to something different. I have a couple of free design spots that I'm willing to give away for this year. Let's go ahead and do these and maybe use that as a way to provide value to my agency partners."

December 24th \- 28th, 2025

December 28th, 2025

Personal

What did you do today?

We had our Christmas Eve service that evening. I did play piano for the entire set and it honestly went really well. All the practice I did paid off. There was only one song, one that Lindsay Hodges led, where I lost my place and played a handful of wrong notes consistently—the note F is categorically not in the key of D. Outside of that, it went really smoothly. JC and I jammed a bit during Joe’s small sermon, with him playing guitar and me fiddling around on the piano. It was lovely.

After the Christmas Eve service, we went and had Thai food with Allie’s family as well as Joe and Carmen Lewis. Christmas Day was a breeze. All we did was see Allie’s family at her parent’s house. Abbey hasn’t told their two girls yet about the impending divorce, so we definitely skated around that a bit. The girls enjoyed themselves immensely. Most of the gifts we gave folks were experience-based, so we all didn’t have too much stuff under the tree this year, which was perfectly fine.

On the 26th, we went to go hang out with the Shirleys and Bouchers up in Canton. Now that the Shirley kids are older, they are a lot more enjoyable to be around. They also love hanging out with Abbey’s two kids, which is a delight. I talked with Nathan, Allie’s cousin, a lot about video games and the Jeep that he wants to buy. I put some good pressure on him to get a Jeep that has a unique color to it versus a boring white or black one.

On the 27th, I realized Chandler Lewis was in town. We had lunch at Zoe’s Tacos and shot the breeze for a while. I found out that they are expecting a kid due in June. I want to play some PS5 with him, but apparently, he needs to buy a table to put his TV on. I need to pressure him about that some.

Today, I hung out with the "baseball gang." Josh Tiensivu and Justin Hancock were both in town, so we hit up Zoe’s Tacos and chatted for a couple of hours. I got to meet their significant others, and I felt sorry for them because we basically just swapped stories of our past for a couple of hours. Both the SO’s are very sweet and I think they both found good people they can build lives around. I'm super thrilled for them. Justin is having a kid in June, too. Good grief. I can’t imagine that dude as a father. Absolutely wild.

How are you feeling about these few days?

Very fufilled. I haven't had to think much about work, which has been nice. I'm not working on Allie's Christmas present anymore, which is nice. I'm not running my DND campaign (which is nice). A lot of things have wrapped up AND I've been able to have good conversations with folks. It kinda feels like I went from 100mph down to 25mph pretty quick. NORMALLY, that is something that makes me literally sick (it's like my immune system says: "Finally\! We can get him now\!" but this year, I've been good. Even though we've had a good amount of stuff to do, I feel like we've had a lot of time to vegitate.

Also, I finished Hail Mary\! I read 8 books in total this year (with 7 of the 8 being in the first few months). I need to continue this habit going into 2026\. I already picked back up Dungeon Crawler Carl \-- that was the book I left off on \-- I think I'm 75% of the way through, so there's a chance I'll finish that before the EOY ..... even though I read most of it in March/April.

Work

What did you accomplish today?

LOL. I basically just worked on my personal website these last few days. I ended up buying the Jack McDade design course and it got me creatively thinking. I came up with a Hero section for my personal website's homepage. It's in a SNES Mario "side-scroller" style. I made a pixelated version of my headshot. I found some cool retro fonts on one of the asset libraries I subscribe to. The thing is... I don't know what to do with it.

Can I build it? Yes.

Is it worthwhile? IDK.

Is it cool and fun? Heck yes.

Can I expedite the building of it with AI? ... not really. It's a unique layout that's hard to transpose.

So, I don't know what I want to do with it. I think it'll be iconic and unique. Then, that makes me think: "Well, to get the MOST use out of it, use it as the CCC website\!\!" But.... I already have a defined aesthetic and have a LOT of building blocks for it. No need to reinvent the wheel.

But, I do like the idea of having something VERY unique to me. Almost as a calling card to say: "Look.. I know how to design cool stuff. Let me do something unique and weird for you too." But, I don't know if that matters.

What did you learn today?

I've learned that I am creative. I haven't really given myself any love on the "design-side" of things. Most of what I have designed recently (which isn't much) has not been super great. But, this little design project shows me that I still "got it" in some way.

Does this small "win" indicate that:

\- I should personally dive more into design work and find more unique projects?

\- This is a distraction and I shouldn't?

\- Since I enjoyed this so much, I should lean more into the Prototype product I've built and do more of that? (and by "more" of that, I mean: "get an actual deal across the finish line")

Did you meet anyone new?

No, I did not.

Family

Nothing new outside of the stuff I talked about under Personal

Deep Dive Questions

You’ve noticed that "external pressure" forces you to work at an even pace, while personal goals (like D\&D prep) suffer from procrastination. With your team’s availability about to drop significantly, do you view the "increased ownership" of 2026 as a healthy external pressure that will keep you focused, or as a risk that will lead to more "reactive" behavior?

This is something I’ve thought a lot about. With my team members “gone,” I’ve had a renaissance of creative ideas. I don’t think correlation proves causation 100% here, but I do think they are remotely related. Yes – client deadlines keep me honest. I have an issue with “people pleasing,” and therefore hit deadlines that are imposed by deadlines for clients. However, with all these creative ideas running around in my head, it’s hard to prioritize what will actually help move the needle next year. I still need to make around $300-400K in 2026 in revenue to be profitable (current retainers put us around $250K).

“Only” having to close $100K is both a sedative and a cause of anxiety. It’s \nice\ because I close that many deals while sitting on my hands. Just these last couple months, I’ve had more deal flow than I have had in a long, long time (now, nothing has closed yet, but the quantity is definitely there). I assume that with all the efforts I’m putting into providing value to people, that will stay consistent through the year.

All of that being said: I feel like some of the stuff that I’ve done that is “creatively reactive” has been good for me, but I need to have more self-control. I almost wish I had an ongoing project that allowed me to flex that creative muscle on a regular basis (...and get paid for it)

You’ve had a massive creative "win" with the Mario-style SNES design, and you’re questioning if you should lean into the "Prototype" design-only product. If you were to treat your own personal website's "weird and unique" design as the first official "Prototype" project, what would be the one metric or reaction that would convince you this is a viable business pivot rather than just a creative distraction?

The one metric/reaction would be someone saying: “OK, that’s dope. I want to stand out too. Let’s work on this together.” Then, how to actually market it out to the masses. I feel like this move is something that is going to appeal to more founder-led companies and not CMOs. I’m OK with that, but how many founders are willing to actually look different in the sea of sameness?

December 29th \- January 5th

Personal

What did you do today?

Today—and really looking back at the last week—has been a mix of relaxation and helping others. Today specifically, I played Fortnite with Mickey Mellen for about 45 minutes1. He had a tough day with some staffing changes he was making, and I wanted to help him unwind. The man is a brick wall, though; he seemed perfectly okay with everything, which just boggles my mind.

Allie and I also went to the gym this afternoon and had a really good workout2. Afterward, we went over to her parents' house to help them move a mattress and a few other things down into their basement in preparation for Abbey to move in with them in a couple of weeks3.

Looking back at last week, Allie and I went over to our friends JC and Mary's house down in Conyers4. We actually brought Daisy, our dog, with us, and she got to meet their dog for the first time. In all honesty, it went really well. We were able to chill out, have dinner, play some games, and the dogs and their child, Ransom, did absolutely fantastic5.

Then on Saturday, the 3rd, Allie hosted the initial session for her brand-new D\&D campaign6. We had all the new people come over to the house, had lunch together, and did all the normal "Session Zero" things—introducing characters and walking through the rules and setup. It went really well, and I think we have a fantastic group for this round.

How did you feel about today?

Today was actually a very relaxing day overall. Allie and I are planning on going to the mountains Thursday through Sunday, so that'll also be very relaxing. This week, from a work standpoint, I don't have a ton on my plate, which just makes personal life a lot simpler, too.

Work

What did you accomplish today?

I actually posted about the SNES-style personal site today on LinkedIn, and it got some really good traction7. Obviously, I didn't close any new business from it, but there seemed to be a lot of interest, and now I'm thinking about how I want to proceed with that tiny bit of knowledge.

One of my primary goals for today was to send out a lot of reconnection emails because my goal is to figure out ways to stay in touch with the ever-growing list of agency owners and potential business contacts I have. I need to be better about staying in touch, so today I sent out about 15 emails and text messages to people I haven't talked to in a while—simply to say "hey," see how things were going, and hopefully schedule some chats. A lot of those were received very well, and I already got a handful of replies back.

I also got back about six fully edited podcast episodes from my editor8. So, I went ahead and wrote up LinkedIn posts for all of them and got them uploaded. Now I don't have to think about my podcast editing or publicizing anything for the next month, which is fantastic.

The one thing I did not accomplish today was sending inactive clients and agency owners the link to the prototype landing page9. I'm definitely falling behind on that because I need to get some more interested people to drum up sales.

What did you learn today?

I learned that I really enjoy having days that are wide open to myself with just a handwritten to-do list of the 4–5 things I have to accomplish. When the to-do list appears never-ending, it's a sign that I have way too much on my plate and that nothing is taking priority. I only listed four items today and got three of them done, so I definitely feel like I accomplished what I set out to.

I was also reminded of one of Tim Smith's motifs, which is simply: just reach out to somebody. There was a mentor of mine named Jack who I was in pretty consistent communication with last year, and at one point we just stopped. I have no earthly idea why. I told myself, "You know what? I'm just going to go ahead and reach out to him today." I sent him a text checking in, and he responded very quickly—which is rare for him—with a lot of excitement. Hopefully, I can get a call scheduled with him. That would be a huge agency contact I had kind of written off just because of a lack of communication. I know he would have work for us this year, and I would love to partner with him again.

Did you meet anyone new?

No, but I will meet two new people in the next two days and go to an event on Thursday.

Family

What did you do today?

Other than helping Allie's parents move furniture for Abbey, we mostly just spent time together10. The visit to JC and Mary's earlier in the week was also a highlight for us.

Deep Dive Questions

You noticed a stark contrast today: you got immediate, organic traction on the "SNES" post (the creative signal) but procrastinated on sending the "Prototype" outreach (the structured sales signal). Does this hesitation suggest that the "Prototype" offer is actually just a "boring wrapper" you’re trying to force because you think you should, and that your real lead magnet for 2026 is actually just doing "weird, iconic work" like the SNES site and letting people come to you?

I was actually thinking about this a little bit today when somebody was talking about niching down. One of my friends, Jesse Barnett, reached out to me when he saw the SNES-style graphic I put up. He basically asked me, "Hey, if you're going to do some more of these, you can use me as a test dummy." So I hit him up with some questions, and I'm probably going to work on something for him just because it'll be fun for me.

The thing is, I'm definitely not going to code this whole thing out, so there's that challenge with doing this work for a friend. But I do really like the idea of being the guy that designs really funky, memorable websites that actually have some style and texture to them. That to me sounds like a heck of a lot of fun, but I don't know how much of a need there is for it in the market.

I also think that in order to be able to pull off an offering like that, you have to have the development chops under your belt as well to be able to then give somebody something like that. Because if you don't do the dev work in-house, that client is going to take a really awesome design, and a random developer is going to neuter that design greatly. So I feel like you have to do everything under one roof to preserve its niceness.

If you commit to this "funky, memorable" path, you are essentially narrowing your market to the "1% of weirdos" who appreciate it and the "1% of developers" who can build it. Are you actually financially prepared to turn down the "boring" money in Q1 to hunt for these unicorns, or is this creative pivot a luxury you can’t actually afford right now?

One of my thoughts is that if I decide to go down the route of some really funky, creative website design and development projects, the other stuff will still pop up. We still have a library of this type of design, and the thing is, by putting my thought process out there, it could be messaged in accordingly.

I think this kind of comes back to the whole mindset of making Classic City into a collective. If I'm the designer that does all the weird stuff, Claude is the one that does the high-end B2B work 11, and Andy could be the person that does any of our Webflow design or something that is healthcare-specific that falls right into his design style12. So, really, we have three designers that come out at a problem in very unique fashions. I'm wondering how that could then be messaged in accordingly.