Private Equity FunCast

Join host Jim Milbery along with guests Alan Williamson (CTO of HiBid) and Kristopher Kubicki (CTO of OpenBrand) as we react to the recent DeepSeek AI announcement, its implications for the AI industry, private equity, and technology companies. We discuss the shock and awe response from the VC and tech communities, debating whether it signals a true paradigm shift or an overreaction. The conversation underscores how AI, particularly LLMs, is reshaping software development, cybersecurity, and investment strategies. While DeepSeek has fueled fears and recalibrations in the market, the real challenge is keeping up with the constant AI evolution—where new models and frameworks emerge at a staggering pace. Companies must remain agile, strategic, and realistic in their AI adoption to truly capitalize on this technological shift.

Jim and Paul kick off the 2025 podcast year. We discuss economic uncertainties, private equity challenges, and evolving market strategies. We explore AI's role in portfolio management, cybersecurity concerns, and operational improvements, emphasizing practical efficiency over drastic changes. The conversation also touches on AI adoption within organizations, avoiding vendor lock-in and training teams to leverage new tools. Wrapping up, we invite listener engagement while reaffirming their commitment to authentic, ad-free content.

Matt Van Itallie from SEMA Software joins Jim to discuss the value of SEMA's code analysis tools for private equity backed companies, particularly for companies managing technical debt, security, and code quality. They highlight the challenges of due diligence in software acquisitions, especially for older companies with legacy systems, and stress the importance of transparency in identifying security and licensing risks. SEMA's AI-driven tools assess code quality and help firms measure the impact of AI-assisted development, making processes like testing more efficient.

Jim welcomes old friend and colleague, Jeremy Burton, CEO of Observe, to the podcast. They discuss the importance of observability in modern software development, the evolution of observability, the challenges of distributed applications, and how advancements in data technology and AI are shaping modern software development and troubleshooting.

Jim welcomes Phillip Weinstein, founder of Atropates Capital who discusses his background, entrepreneurial journey, and the concept of starting a search fund. The conversation covers a range of topics, including Phillip's first entrepreneurial venture at Wake Forest University (a laundry service), through founding his search fund. The discussion explores how search funds differ from other business models, such as private equity and venture capital. Phillip shares his insights about finding and evaluating deals, the challenges of operational leadership, technical debt in software, and integrating AI tools.

Join Paul from the ParkerGale Ops team as he unpacks the concept of "product-market fit" with special guest, Rob Snyder – multiple-time startup founder and Fellow at Harvard Innovation Labs. Paul and Rob explore the origins of the PMF concept, what it means, and why it's both an essential and confusing concept for PE-backed tech companies. Learn about the importance of building a shareable case study, the pain cave you inevitably enter while trying to connect with your customers, and how to use the concepts of demand versus supply to shorten your search for product-market fit.

Devin spends an hour with Ankur Gupta, PNC's Global Head of Technology Finance, to discuss the current state of software company lending. We cover where PNC fits in the lending landscape, what a "good fit" deal looks like, what you should expect during due diligence, what covenants you should expect, and where pricing is across different lenders these days. We also cover how lenders think about Gross Retention vs Net Retention, ARR to loan values, and growth vs. profit.

Jim's longtime colleague and friend, Rick Greenwald, joins the podcast to discuss the ins and outs of the famous Magic Quadrant. The episode provides an in-depth look at the complexities of Gartner’s evaluation process and offers practical advice for companies aiming to improve their market positioning and strategy.  Plus, we've known each other since at least 1990, so lots of conversational detours.

ParkerGale Principal Cass Ziebel sits down with CFO Jon Danielson to discuss the priorities of a PE-backed CFO and what he's learned from a recent sale process. In this episode, Jon talks about what surprised him most when he moved from an investor role to an operating role, what it means to "shrink the QofE," and advice to other CFOs as they enter a PE-backed business in the first few months and prepare a business for sale.

In this interview, Jim and Yuval Yeret discuss the implementation and challenges of agile methodologies within the private equity space. Yuval has extensive experience in product development, and he emphasizes the importance of principle-driven agility over rigid adherence to frameworks. While agile practices originated in software development, their application is beneficial across various industries and organizational functions. Companies often struggle with "agile theater," where companies follow agile rules without understanding the process. Effective agile adoption requires cross-functional collaboration, adaptability in strategic planning, and the ability to balance customer flexibility with engineering realities. Yuval shares examples from biotech and healthcare, illustrating how agility can extend to broader business operations. He also discusses the role of OKRs (Objectives and Key Results) as strategic guides rather than rigid metrics. Finally, Yuval underscores the unique position of private equity firms and consultants in driving agile transformations through pragmatic, principle-based solutions.