I hope you’re all doing well and had an excellent February.

As most of you know, under the Third South umbrella, we own and operate a portfolio of different software companies. Today’s update is focused heavily on EntryThingy, a platform we bought a couple of years ago from Chris (who, post sale, started a bakery). It’s a two-sided marketplace where galleries post calls for art, and artists find and apply to those shows. It also has a subscription product for artists to manage their online portfolios.

When galleries look for a platform to host their calls, they care about three distinct things:

• Price: We are by far the most affordable on the market.
• Quality: We believe we offer the highest-quality interface and a feature set that’s on par with—or ahead of—competitors.
• Marketing: How effectively the platform can get their calls in front of actual artists.

We previously addressed the quality piece of the business during the rebuild of the old version of EntryThingy. We spent almost all of February putting our heads down to build a massive marketing engine to tackle that third pillar. Here is a look at what we shipped, how we are prioritizing our time, and the infrastructure changes happening behind the scenes:

The Recommendation Engine is Live (and the data is great)

Because EntryThingy has been around for nearly two decades, we have a database of 160,000+ artists. A huge chunk of our month was spent getting these artists consented into our email list so we can start sending them targeted, highly relevant monthly recommendations. We noticed competing platforms are charging galleries several hundred dollars just to feature them on their email blasts — what if that was something we could offer for free to benefit our flywheel? Marketing emails are something our customers want: galleries like to see their calls promoted, and artists are looking for opportunities.

Harrison built out the scaffolding for these campaigns, and I built a brand-new call recommendation engine to power it. The engine matches artist mediums and locations to open calls, ensuring we aren't just blasting emails into the void, but delivering actual value.

We just ran our latest weekly send, and the early data is fantastic:

• Open Rate: 70% (3,277 opens)
• Click Rate: 24% (1,146 clicks)
• Conversion rate: data is murky. We haven't seen as many conversions as we would like, but we know it is well above 0

Building for Artists (and retiring the "Shiny Object")

We want artists to stick around long after they’ve applied to a show. To make that happen, Colin has rebuilt the artwork management side of the business. This is our subscription-based product that allows artists to build their own website, manage mailing lists, and create an easily shareable online portfolio. (You can check out a great live example of an artist portfolio right here: Diana's Portfolio.)

When you own multiple companies, you operate on an infinite canvas of potential tasks. We could build a thousand different features for these artists. So, how do we choose?

I recently wrote a piece on our internal framework called The Language of Shiny Objects. We are officially retiring the phrase "shiny object" as a slur for technical tasks. Instead, we ask one question: "Given an infinite timeline, would we do this?" If the answer is yes, it’s a Valid Investment. If no, it’s a Distraction. Colin's portfolio builder is a massive Valid Investment for our users.

Operations: Killing Middleware and Conquering Support

I recently did a deep dive into our portfolio's tech stack in his 2025 Vendor Audit. The takeaway? We are keeping mission-critical infrastructure (like AWS), but we are aggressively killing "middleware." AI has made technical chores trivial enough that paying a premium for an "easy button" wrapper no longer makes sense. A lot of these services work just fine, but the spend and complexity across multiple portfolio companies adds up. Over time, it makes sense to migrate a lot of these to internally built solutions.

This philosophy ties directly into how Justin has been overhauling our customer support. Galleries care deeply about support, but historically, juggling tickets alongside deep-focus work caused a lot of anxiety for our small team. Justin leveraged AI and custom tooling to remove roadblocks and make us quicker and better. We now have custom admin panels in Help Scout (our customer support tool) that allow us to instantly view a user's activity and troubleshoot.

Furthermore, we changed our human infrastructure: instead of everyone doing support simultaneously, we now rotate. Each team member takes a one-week shift where their only priority is getting the support inbox to zero. If they accomplish nothing else that week, it’s still a win. February was easily the best month for customer support we’ve had in a long time.

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We love talking shop about how we run these businesses. If you have any questions, thoughts, or ideas, hit reply and let us know!

Best,
Myles, Colin, Justin, and Harrison