Phase 1: Better Late Than Never?
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Phase 1: Better Late Than Never?

September 2, 2026

One of my brilliant mentors, Alex Cooke, told me three years back that I should start blogging about all the entrepreneurial work I'm doing. Better late than never, Alex?

Since that conversation, so much in my life has changed. I moved away from California, where I lived for thirteen years. I got a job working at Physicians First Bancorp, thanks to Dr. Thomas Chambers. I got a second consulting position at Sensor Shield, shout out to Shirley Yager and Zachary Jones. I married my beautiful wife, Madison McCaffrey, and now we have a baby girl on the way.

Nine sites in three months

In the past three months, I've been a little obsessed with building websites. This obsession has led to the creation of nine separate website builds. No, I'm not a programming prodigy. I've just gotten pretty decent with Claude Code and am doing my best to learn how to improve and maintain code, not just crank out slop.

Right off the rip, I want to acknowledge my gratitude for Tucker Sholtes, who has tolerated hearing about each and every single one of these pivots in agonizing detail. I honestly would not have made this web development without your mentorship and guidance. Also, shout out to Dylan Simowitz and Don Felker, who have helped me make sense of the wonderful world of code.

The first website I built was startupmb.com. This is hopefully to serve as a localized Crunchbase for Myrtle Beach since we are in a "tech desert", even though there are loads of interesting and innovative companies doing great work here.

Then, I got annoyed that I never knew exactly how much to water my grass. As a first-time homeowner, my grass looked really rough in spring and at the beginning of summer. My mom and I would debate it all the time, looking at different rain gauges and relying on the basic glass ones in my yard. I figured, why not build Palmetto Rain, a super-complicated algorithm that would take weeks of my time just to save a few hundred bucks a year. I suppose the broader vision is that more people will start using it as well, and eventually it will have a really nice pro-environmental impact.

Next, my sister Claire McCaffrey needed a website for Sunny Visions Co to display her portfolio. Claire, we still need to add your domain!

Next, my wife and I could never seem to figure out exactly when to feed our sourdough starter. This, luckily, is much simpler than watering a yard. I'm going to come back to Our Starter Home because we're going to make it more of a first-time homeowner/parenting blog.

I showed these sites to my bosses, Dr. Thomas Chambers and Marty Nichols, at Physicians First Bancorp. They must have thought they were all right because we rebuilt the bank's website, pfbancorp.com, from scratch. I will say, I'm pretty proud of all the native e-sign features we built into the site.

Then, in August, I started making this site you're on now, willmccaffrey.com. Something I have made a few cracks at in the past and not fully committed to yet. But, here we go.

And this is where it gets crazy. My friend and realtor, Shonte Jordan, who sold us our house, kindly asked me to do some real estate social media videos for her. We got to talking one night while filming, and I mentioned to her I was building websites. She sent me an example of a short-term rental property site she loved, asked if I could build her something like this, and how long it would take. That turned into beachshackat54th.com and the backbone of skipbookingfees.com.

Then, Shonte very kindly recommended her friend Erica Pedro, for whom I built themartinibay.com. Whew, it really has been a busy few months.

Away from the desk

So, I've been sitting at my desk considerably more than normal. I'm typically someone who likes to get up, take breaks, go on walks to think, etc. This is the first time in a long time when I've been locked into a mode of blissful obsession for the majority of each day and night.

The only handful of things I made time for outside of programming was going on a camping trip with my brother Michael McCaffrey up in Brevard, NC, to get excited for his upcoming wedding. I was gifted some Egyptian walking onions to plant in my garden, and purchased some awesome lemongrass stalks for $1 that were like five feet tall. I guess inflation has not ruined everything yet.

Phase 1: the nursery

But, as previously stated, I do have a baby on the way. A baby girl, to be specific. The first trimester is over, so it is crunch time for house projects. And, what better place to start than a nursery? So far, I've probably spent about three hours placing painter's tape in the bedroom and the jack-and-jill bathroom. We are planning to do some cool millennial pink chair rail with wallpaper above. I will definitely include pictures in my post next month.

What's next

On the web building side of things, my goal is to ideally get one new STR client per week. We will see how that pans out. Also, I'm helping my brother-in-law, Bradley Wactor, build out a new website for Bluff Road Auto Sales.

About the patch

So why a patch of a guy on a laptop sitting beneath a live oak tree? One of my favorite albums growing up was "In Between Dreams" by Jack Johnson. I absolutely loved the cover art as well. While I love nature, I seem to also have one foot in the digital world at the moment. Especially since all my work is remote. I guess I'm more in between sites, but building towards some dreams.

Anyways, if you made it this far, thanks for reading. I apologize for posting a day late. I'm sure you were really stressed out about it. I'll try to do better next month. But, better late than never?