You might have heard I had a breakdown. I didn't. I had a breakthrough.
For the better part of two years, I went dark. Not the strategic "I'm rebranding" kind of dark. The real kind, where friends text your wife to ask if you're okay, where LinkedIn goes quiet for months, where the algorithm decides you're dead and stops showing your face. Some people heard it was a nervous breakdown, and I won't pretend the rumor has no basis. What else do you call it when a guy who was active and visible and building just goes silent?
The truth is less dramatic and, I think, more interesting. I walked away from a situation that was eating me alive. The organization I'd been working with had gone toxic in ways I don't need to detail here. If you've been in one, you know the shape of it. I was giving my best hours to something that was making me worse, and one day I just stopped.
But I wasn't lost. I had a plan. And underneath the plan was a thing about me that's been true my whole career: I solve coordination problems. Not concrete, not code, not facials. Coordination. Wherever work gets stuck, repeated, or trapped in one person's head, I'm the one who notices the gap and builds the missing piece. That instinct is the only straight line through everything that follows.
The Decision
I'd spent years in ultra-high-end custom residential construction, builds running north of five million, some past ten. I'm still a licensed general contractor and I'm genuinely good at the building side of it. But I'd come to believe the cost-plus model is broken. You're asked to tell someone what their project will cost before anyone knows the full specs, before the changes nobody can predict, while the homeowner is already sure they're getting the best possible price. It almost always ends up costing more, the relationship turns adversarial no matter how well you manage it, and you spend your life defending skilled tradespeople against the idea that they should work harder for less. I decided I was done fighting that particular fight. That doesn't erase twenty-plus years of experience. I just wasn't going to spend my remaining years inside a model I don't believe in.
What I wanted instead was closer to home. My wife Amy is a serial entrepreneur and a licensed esthetician with over twenty years of experience and a fiercely loyal clientele she could no longer fully service on her own. We needed to bring on more estheticians, modernize the systems, and build the studio into something that could run beyond just Amy in a room. And it was bigger than the studio. Amy wanted to teach, to launch a training program, which meant content, documented SOPs, systems other estheticians could learn from. Someone had to build all of that. I was the one who knew how.
So the plan was simple to say and hard to do: rebuild the business, launch the training platform, and set our lives up for the phase we actually wanted. More travel. More freedom. More of the work that makes us happy.
None of this was as far from construction as it looks. I had a whole life before the job site. An import business that let me travel the world young. Two retail stores. A career doing audiovisual production out of my own recording studio. Different surfaces, same job underneath: keep complex operations running without dropping anything. Even on the big custom builds, the real work was never pouring concrete. It was keeping information moving. RFIs, change orders, schedule updates, permit timelines, vendor invoices. The failures were almost never construction failures. They were coordination failures. The stone was wrong because the spec missed a revision. The inspection failed because a trade ran ahead of the engineer. The overrun came from changes nobody reconciled.
I'd spent years reaching for tools that were supposed to fix that. Smartsheet, CoConstruct, Buildertrend, Booker, ClickUp, agile kanban boards. Every one solved part of the problem. None solved all of it. And I have a knack for finding the exact thing a piece of software won't do that you most need it to. Software companies all tell you their platform is going to save you money and solve all your problems, and they're just lying. So I'd build the "workaround." Zapier, spreadsheet formulas, whatever glue I could find. I was always building the missing piece. I just didn't have real tools yet.
The Forcing Function
The real change didn't come from a plan. It came from a crisis.
Amy had been on Booker for close to a decade and it worked. But she wanted a more modern presence, online booking, newer features, so just before I left my job we migrated to Square. That's when things broke. Square seemed fine at first, but once we hired our new esthetician and ran more clients through it, every gap became a crisis. Amy runs a results-based skincare clinic. She needs to see, fast, what active ingredients she's used on a client's face over the past year, what they've bought to take home, and how it all connects, so she can tell what's working and adjust the plan. Square couldn't do that. Not well, and in some cases not at all. She's got a few minutes between clients to turn the room, and the information she needed simply wasn't there.
So I went to work, fast. I pulled data out of Square to build at least a historical record, scaffolded systems around it in Airtable, and built dashboards, client-tracking tools, and a workaround for every gap. Some of it I built in hours, because my wife was stressed and I was trying to stop the bleeding. At one point I was on a call with Square's own sales and dev teams telling them I'd built a better version of a feature they were selling, myself, in Airtable, in an afternoon, for free, which is more than I can say for Square. After the triage I made the call to move us to Boulevard.
Boulevard is built for medspas and higher-end esthetics, and it gave Amy enough to breathe again. More importantly, the enterprise account came with something Square never gave me: API access. That was the turning point, and not overnight. Over months I learned how to actually reach into data on a level I'd never had before. Slow going. I'd spend a whole deep dive on API calls and come away having understood a little more of what I could and couldn't do. I'm not a trained software developer. I'm persistent, and I'll brute-force my way to a solution, which had been my technique with AI from the beginning, back when most people didn't even know what it was.
What I was chasing through all of it was payroll automation. Ours is ugly: hourly or commission, whichever is greater, calculated per employee, with clean records every single week. The idea that I could automate that kept me going through the slow stretches. It took months. But I could see the light, and I kept walking toward it.
What It Became
The studio was growing the whole time. We added HydraFacial and a second treatment room. I bought cameras and lighting and found my old video-editing instincts came right back, which turned into real marketing: over 200 leads from our ads, 55-plus new clients who became regulars.
I also took a run at business-to-business consulting with contacts in the construction industry. Mixed results. I learned fast that businesses say they want process change, but when it comes time to actually pay for it or change anything, most are just trying to get through the day. Not everybody wants their world rearranged, even when it needs to be. I'd run into that before in my career. People just don't want to do anything different.
Then came Estate South, and that's when I reached for real tools.
I'd done a major project for a couple in their 80s years earlier. They had a flood, and for them it was a disaster. They needed someone they trusted to navigate the whole situation. They didn't care about locking me to a price. They knew I wouldn't mark things up, knew I was on their side. After years of adversarial construction relationships, it felt like alignment, and it reminded me I still had something to offer people. There are property owners out there who need a person in their corner, someone stewarding the place on an ongoing basis instead of a contractor who shows up when something's already broken. That's the idea behind Estate South.
It's hard to put property stewardship on paper, so I leaned on what I knew. I generated about 400 video clips with Google AI Ultra, cut them together with that old musical-editing instinct, and gave the concept an emotional hook you don't usually get in a pitch deck. And because no concept video is complete without a little swagger, I had AI narrate the whole thing in a Burt Reynolds voiceover. The concept video was compelling enough that a lot of people, including me, could look at it and say: there really is a market for this, even if it's hard to explain in a sentence.
Building Estate South was the moment I picked up an AI-assisted coding platform for real. Within a few hours I had the first piece of what became a multi-application system. A completely different level of control. Sites and tools that did things, with real logic and real data, not just nice-looking pages. Within weeks I had three applications built deep, and then I realized I needed them to talk to each other, and discovered I'd architected myself into a corner before I'd even finished my first real app. So I found Supabase, a real database with row-level security, picked up another coding platform, and rebuilt everything through a unified security model. Things that worked standalone broke under it, so I fixed them, and kept going.
By this point Amy had also launched Great Skin Essentials, a pharmaceutical-grade skincare line, alongside a podcast called Gen X Esthetician, virtual consultations, and a Shopify store. Being married to a visionary when you can actually build things is a fast way to get yourself into real trouble. The Estate South app, tools for Amy's studio, client-facing software, websites that actually worked: it was all running in parallel, all being built at once.
The steepest part of the climb was self-hosted AI agents, and it nearly took me under. Sixteen, eighteen-hour days, money going out the door, a system that kept mutating underneath me while I tried to fix it, until Amy finally told me, quietly, that she needed me back. She was right. I wrote that whole stretch up separately — Two months down a rabbit hole with OpenClaw. The short version is that it supercharged everything. I came out the other side with real skills I didn't have before. Software development. Database architecture. Agent systems. AI memory, which is one of the live frontiers in the whole field right now. I went in trying to build a tool and came out a different person.
The Breakthrough
Through all of it, various contacts kept reaching out to offer me roles in construction. I can walk in, know everyone, know what it takes to get things built. Every time the door opened, I couldn't bring myself to walk back through it. Because solving problems in our own businesses, building the things we actually needed, had given me the most satisfying professional stretch I can remember. That's when it landed: I've got too many ideas to work for someone else. I'm built to build my own things.
So that's what's running now. Estate South is in beta. We walk properties, photograph everything, and AI models analyze each image the way a trained preservationist would, organizing it into a maintenance plan clients reach from a dashboard anywhere. I'm in conversations with partners about scaling it. I'm doing owner's-rep consulting for clients who need someone in their corner on complex construction, work that found me on its own. I've launched Digital Ops Box to show what I've built across our businesses and for the people I've helped, and to take on select work for others who need that custom layer between off-the-shelf platforms and how their business actually runs. I'm putting some tools on GitHub too, including a transcription platform and a construction takeoff tool that does what subscriptions costing hundreds a year do, without the subscription.
The agent system is running the things I built it to run. Books reconciled across all our companies, transactions matched and queued, a couple of keystrokes from done — automatically. Content pipelines running across four channels without me shepherding each one. A routine that scans retainer clients, flags who's over threshold, and drafts the invoice for my approval. The studio is thriving, the skincare line is live, the podcast is publishing, and Amy's assistant can update a client's home-care plan without either of us opening a laptop.
It's not finished. I don't think it's supposed to be.
It's hard to rebuild at 50. It's hard to step away from the thing that made you look successful from the outside, the position, the authority, the money. But what's it worth if you're miserable? The departure was abrupt and I know it caught people off guard, and reconnecting after two years of silence takes something out of you I didn't expect. I came out the other side with skills and an understanding of my own capacity I didn't have before, and one thing I'm now sure of: I'm not built to work for someone else. Maybe I never was.
If you run a business and keep bumping into the gap between what your tools do and what your operation actually needs, that's the problem I've spent my whole career solving. Construction, retail, a recording studio, a spa, and now software. The job never changed. The toolbox just got bigger.
You might have heard I had a breakdown. I didn't.
I had a breakthrough.