The Ghost of Software Future

In February of this year, an obscure research report triggered a $1 trillion wipeout in software stocks in seven days. In this episode we decipher what actually happened — and why AI is more likely to be a gift to enterprise software than a death sentence.   Devin and Jim have invested through every major tech transition: PCs, client-server, the browser, mobile, the cloud. This time, they're breaking down the four bear cases for enterprise software (private credit, seat licensing, vibe coding, the AI bubble) and sharing what's actually happening inside their portfolio. The ghost shows up every decade. Here's how not to get spooked.   READ: "The Ghost of Software Future" on Substack

Selling a company isn't just about price - it's about timing, preparation and process. In this episode, Devin sits down with Ryan Milligan to break down how to sell a company - from timing the exit to running a competitive process and getting a deal across the finish line. They walk through the full private equity playbook including when to sell, whether or not to hire a banker and how deals move from early conversations to signed LOIs and closing. If you've ever wondered how exits happen behind the scenes, this episode illustrates how it really goes down.

Everyone loves the chase but what happens when the ink dries on the deal and you actually own a company? In this episode, Jim sits down with Paul Stansik to pull back the curtain on how the combined deal, ops, and management teams come together in the first few weeks and months post-close. They break down what life looks like immediately after an acquisition, including setting up governance, identifying talent gaps and figuring out where the real opportunities (and risks) are hiding. Jim and Paul also hit on the softer side of what happens during the early-hold period, and the importance of curiosity, connection, and trust-building inside ParkerGale's approach to value-creation. Ever wonder what your investors are thinking about during the first few months of a new investment? Curious about what happens when diligence is over and things get real? This is the episode for you.

It all starts with an acquisition, but most people don't understand how private equity firms actually find and buy companies. Devin sits down with Ryan Milligan to break down the mechanics of deal sourcing, banker-led processes and direct founder relationships.  From the early days of rotary phones ringing with deals to today's hyper-competitive sourcing environment, we discuss how firms build pipelines, win founders over, and decide which companies to buy.  If you've ever wondered how private equity truly functions behind the scenes, this is your go-to guide for the entire process.

Raising your first private equity fund is humbling. Like Lloyd Dobler holding a boombox outside an LP's window, you need to be committed and creative. It took us over 150 meetings and almost 2 years to get to the finish line. One LP fell asleep mid-pitch. We got stranded in a monsoon in Connecticut. Kenny the Associate torpedoed us in Manhattan. Jim got locked out, and Devin had to fly solo. We survived. You can too. From hiring a placement agent to practicing your pitch to getting LPs to tell you what they want, to recharging your batteries on the road so you can keep going til the end. This is everything we wish someone had told us. Always Be Closing. Kinda.

In this episode, Devin and Jim rewind to 2014 — and a $12 bottle of Cabernet at the Macaroni Grill — where they hatched the plan to leave their firm and build a new private equity firm from nothing. This is the insider's guide they wish they'd had.

It's our annual Predictions episode (and by annual, we mean just the years we remember to record one). Devin and Jim offer their hot takes on fundraising, liquidity, why artificial general intelligence (AGI) is still years away, and whether or not the world is officially "over-softwared." PE FunCast New Episodes Every Wednesday Follow us on social media and subscribe to our Substack! LinkedIn: https://www.linkedin.com/company/parkergale-capital Instagram:https://www.instagram.com/pefuncast Substack: https://substack.com/@pefuncast Facebook:https://www.facebook.com/people/PE-FunCast/61580605382460/?mibextid=wwXIfr&rdid=UXSOfkHvpixQjCyB&share_url=https%3A%2F%2Fwww.facebook.com%2Fshare%2F14VqLVUrhVD%2F%3Fmibextid%3DwwXIfr TikTok: https://www.tiktok.com/@pefuncast X: https://x.com/PEFunCast

Devin sits down with Funcast listener and Terem Capital CEO Scott Middleton. Terem is a software holdco in Australia, and Scott shares his strategy, investment criteria, sourcing approach, and the difference between US holdcos. 

Jim sits down with Sean Lucq (Partner at SPMB Executive Search) to talk about the art of hiring senior engineering and product leaders—especially now that every job description on Earth has "AI" duct-taped to it. We get into why sticking with one great search firm beats "random recruiter roulette," why tech interviewing is tough (spoiler: engineers aren't always born interviewers), and the eternal tension between the two key roles - CTO (big brain science/vision) and VP Engineering (keep the trains running, preferably on the tracks). Then it's on to the AI gold rush: what a normal Head of Engineering should actually be doing with AI (hint: practical stuff like code review, QA, automation), why "Head of AI" is usually a totally separate job, and why "10 years of LLM experience" belongs in the same bin as Web3 buzzword soup. We also cover who's moving jobs right now, why PE can feel like a saner bet than venture (less "moonshot," more "actual exit"), and what candidates must be able to explain: what you did, and how it moved the business—numbers included. Plus: a few recruiting war stories, including the kind you can't make up and the kind that makes you grateful for a boring Tuesday.

In this episode of The Private Equity Funcast, Jim Milbery sits down with Jennifer Nelson (CEO of Izzy Software), Richard Malone, Rob Swanson (co-founders of CNX Corporation), and Iwona Montgomery to talk about CNX's nearly 30-year glow-up — from green screens to the cloud. After almost three decades in the biz, CNX just joined forces with Izzy Software, and the result? Legacy systems that finally got the spa day they deserved. We dive into how moving to the cloud has made life easier for developers and why low-code tools are giving old-school software a serious second act.