On the latest Behind the Buyouts podcast, Thoma Bravo LP partner Carl Press turned the clock back to discuss the parallels between the software investor’s early days and its Explore middle-market fund.

“As our firm grew and as our flagship funds grew in size from $3.5 billion to $10 billion and $25 billion, we kind of got away from that middle-market segment — that really is where we cut our teeth and grew as a firm and had a bunch of our early success,” Press said.

Press co-leads the Explore fund, which launched in 2020 and typically makes equity investments of $50 million to $250 million in segments from applications, infrastructure and cybersecurity to financial technology, healthcare and information technology. While Thoma Bravo backs founders — a prized opportunity in middle-market tech — the firm also has a strategy for investing in joint ventures.

With the Explore, Flagship and Discover funds, Thoma Bravo covers software from the lower middle market to the bulge bracket. “We have three distinct buyout funds that allow us to make control investments in software up to $12 billion of enterprise value, all the way down to about $100 million of enterprise value,” Press said.

The funds have a symbiotic relationship, providing partners with a window into niches beyond their funds’ immediate purview.

“We joke sometimes that there’s an old saying about bringing a gun to a knife fight,” Press said. “I feel for Explore, when we go in the middle-market deals, it’s like bringing a bazooka to the knife fight — having Thoma Bravo as our parent organization and being able to leverage the operating partners that we have at our firm.”

Here’s the podcast with Carl Press:

More podcasts from The Deal are available on iTunes, Spotify and on TheDeal.com.