Hi! It’s been a few months since you last received this newsletter. Here is what has been going on:

EntryThingy Turnaround

When we bought the company, the codebase was a liability. Customers stayed for one reason: we were the cheapest option. We had no roadmap, just a broken asset. A good asset in some regards, but still, a fundamentally broken asset to build upon.

We tore the code down and rebuilt it from scratch. For a specific cohort of art galleries, EntryThingy is no longer just the cheap option, we are the best option. That feels good to say.

You’ll love this: I found out greatmemos.com was available, so I bought it. It’s live right now!

You’ll notice the site is a repository of the best memos out there. You are the first to hear about it. Check it out and reply with any memos that should be added!

On the Third South front, we are doubling down on what works. With EntryThingy, we are simplifying how artists of all sizes find and submit work, which includes promoting our competition. With Third South Services, we are tackling a similar rebuild opportunity, but in the finance world.

The ET V2 launch wasn’t perfect. We found bugs. Some were legacy gremlins…some were our own doing. It’s embarrassing to have to fix things we convinced ourselves were fine. But our goal is to make the most useful platform for artists and galleries. We are almost there.

I hope you had a nice October! Mine constituted trips to Washington D.C. and New York City. There were some wonderful people in both cities, most notably family in D.C. and friends in New York.

I went on a spree and bought about fourteen over the past couple of weeks. The favorite thus far is Elon Musk by Walter Isaacson. Sam Walton’s Made in America is the current read. And I’m most looking forward to Napoleon: How He Did It, which was written by Napoleon’s long-time secretaries.

The finished and wrote-up books include insights gained from the Wright Brothers, Seven Days in the Art World, and The Only Rule Is It Has To Work.

Over the past month, I wrote about my gripes with email hygiene, an unlock in design engineering, and a long-held belief around the world being nothing more than a mirror.

Hi all,

September was mostly spent on rebuilding EntryThingy (more on this soon!) and settling into Carlisle. I didn’t write to you all in August because I traveled to France for a wedding, and to Williamsburg for family.

If you’re in New York, Richmond, DC, or Philly in the coming months, let me know. I'd love to see you!

Here are some pictures from a hike:

So July is wrapped up. I did a lot of writing, a lot of traveling, and had a lot of fun this month. Here are some of the published pieces from the past thirty days:

• The Earned Secrets of Constellation Software

  • for those who read this earlier, thank you for the kind notes
  • please reply with any reactions/questions to this piece, a follow up one is in the works!
  • Assorted Notes on the Union Tank Car Company - practical monopolies
  • Goodbye, Richmond, reflections on the River City
  • How I gave in to the dark side and started breaking habits.
  • Evolving my relationship with writing.

How We Published 3 Interviews in 4 Hours

We’ve unlocked an efficient new way to create content. In about four hours, I recorded, transcribed, and published three hour-long interviews:

• Third South Capital: Learn how our founders are building software companies without knowing any programming.

• Founder Spotlight: An interview with the founder of one of our recently acquired companies.

Our process is simple and AI-powered: Google Gemini handles the transcription, an AI agent refines it with pre-set instructions, and we get a polished Google Doc that requires only a few minutes of final review.

Investing

I joined Colin, Justin, and Harrison at Third South Capital as a full-time partner. We're buying and operating software companies. You can read our first public update here.

Most of my time in public markets has been reduced to special situations and acquisitive conglomerates due to the low research requirements. I’d rather spend the time on building companies with my friends!

Writing