In building Third South, we gave very little premeditated thought to the topic of vendor consolidation. After owning and operating assets for two years, we now have opinions!

Each of our portfolio companies does two things, more or less: deliver a web-hosted service to a customer and accept payment for those services. Exactly how each company does the service delivery varies.

Some are apps in an ecosystem where significant infrastructure is provided by the ecosystem host. Others are more traditionally built SaaS, where we are responsible for all aspects of service delivery from development to deployment.

Our Preferred Stack (details below)

Third South has had two offsites this year, one in February and one in July. Here are some reflections that hopefully are helpful.

Our History with Offsites

We began Third South Capital with an accidental offsite. In late-2022, Colin visited Richmond to brainstorm about some entrepreneurial ideas with me and Justin. We didn't call that meeting an offsite at the time, but it was: it was the offsite that formed Third South. Once we started Third South formally, our basic plan was to meet in person once per year. At that time, we were each managing other full-time obligations, and Third South was a part-time project for all of us. During “Third South 1.0”, offsites essentially consisted of asking:

Authored by: Harrison Roday

From late 2022 to 2023, our team at Third South Capital evaluated dozens of potential acquisitions. The idea was to pool our personal capital and start a permanent holding company of niche software businesses. After six months, we had nothing to show for it.

Things started to change when we met Denis Leonov. His product, Clipboard History Pro, became one of five companies we acquired in less than two months. This is the story of the acquisition, completed two years ago in July 2023.

Meeting Denis and Kicking Off Diligence

Neither Colin nor Harrison have technical backgrounds, yet they have been shipping complex technical projects touching thousands of users due to advancements in AI.

This story is not theoretical. It’s about how two non-technical investors rolled up their sleeves to drive tangible value for their users.

From early AI explorations to spearheading complex technical projects, Colin and Harrison demonstrate how these new tools are reshaping the trajectory of Third South Capital:

Myles: Could you start by telling me about your technical backgrounds?