Jim Milbery and Devin Mathews

Private Equity FunCast

Business EN ↓ 323 episodes

Your favorite GP's favorite podcast. Occasionally insightful, always entertaining. Deep dives into how private equity works, what happens after the deal closes, how money gets raised, and how companies get bought and sold. And everything in between with healthy doses of pop culture and humor. Straight from the team at ParkerGale Capital. For educational and entertainment purposes only. Not investment advice. Additional disclosures at www.parkergale.com.

Author

Jim Milbery and Devin Mathews

Category

Business

Podcast website

www.pefuncast.com

Latest episode

Jul 8, 2026

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Episodes

Anatomy of a Security Assessment 29.04.2020

Jim talks with Paul Petefish from Evolve Security about the ins-and-outs of an actual security assessment -- ours.   We cover everything from penetration testing to phishing attacks.

Part II : How the world of sports thinks about culture 22.04.2020

The conclusion of our two-part episode (both recorded before the coronavirus pandemic) with ParkerGale advisor and former Chicago Bulls team psychologist Dr. Steve Julius discussing how elite sports franchises think about organization and team culture and what can be applied into a business context.

How the world of sports thinks about culture 15.04.2020

In episode 1 of a 2-part episode (both recorded before the coronavirus pandemic), Jim, Jimmy, and Paul are joined by ParkerGale advisor and former Chicago Bulls team psychologist Dr. Steve Julius to discuss how elite sports franchises think about organization and team culture and what can be applied into a business context.

March Madness 2020 – Slightly Delayed 06.04.2020

Weeks ago, before we were all focused on the coronavirus pandemic, Jim and Jimmy recorded our (mostly) annual March Madness episode. We hit pause on posting this one for a while, but on what would have been the finals of the men's college basketball tournament, we thought a little levity would be something listeners could use.  In this episode, the months of the year face off in a battle for supre...

Quick Information Security Suggestions for Remote Work 30.03.2020

We talk with Paul Petefish, Founder and CEO of Evolve Security about some simple and fast suggestions to make remote working more secure.

[Replay] A Parade of Terribles: Founder Legal Traps to Avoid 17.03.2020

A fan favorite episode -- The FunCast spends an hour with Kirkland & Ellis partner Ryan Harris (formerly of McDermott Will & Emery LLP) talking about the legal traps founders fall into when setting up their companies and when they sell them. What's the best company structure -- C Corp, S Corp, LLC?  How do you handle employee equity?  Hear about the infamous "Cubs side letter."  What are the commo...

The Second City, "Yes AND," and Private Equity 10.03.2020

Jim and Jimmy are joined by Marla Caceres and Nelson Velazquez, improvisors at Chicago's famous Second City Theatre. They discuss how ParkerGale has leveraged the Second City Works to provide professional development for senior executives in addition to the concepts that underpin the Second City philosophy and why they are so important to fostering growth, teamwork, and innovation. Oh – and don't...

What is Customer Success? And why should you care about it? 03.03.2020

On this episode, Jay Nathan (Founder of Customer Imperative) joins Paul Stansik to share how companies can be more intentional in building intimacy and delivering value to their customers. We talk about how his consulting firm builds customer success teams, how business leaders get this wrong, and the baby-steps that anyone can take to "make the renewal a no-brainer."

Interview with Dean Brown, CEO of Ipro Tech 24.02.2020

Jimmy sits down with Dean Brown, CEO of Ipro Tech. Dean discusses his upbringing in a military family, his education in Industrial Psychology, the serendipity of a career, his love of products and product strategy, his experience founding, scaling, and ultimately selling his startup, why culture is so important to him in business, and much more.

Why does the PE firm care about your product roadmap? 14.02.2020

In part 3 of a 3 part series on Product Strategy, Jim and Cici continue the discussion of how product strategy ties into value creation, and how specifically as a PE firm, we monitor our portfolio companies' product strategy through taking a detailed look at their product roadmaps. We discuss how we conduct Product Strategy Reviews – the objectives, who's in the room, and what we actually cover. W...

How we link Product Strategy to Value Creation 05.02.2020

In part 2 of a 3 part series on Product Strategy, Jim is joined by Cici to discuss the private equity investor's perspective on how and why products get built. Living in a world of limited resources, we discuss the framework that we use to help shape the discussions with our portfolio companies about prioritizing their products and features. We talk about market segments versus markets, the Ansoff...

How we think about Value Creation - Risk Mitigation, Cost Reduction and Revenue Growth 27.01.2020

In part 1 of a 3 part series on Product Strategy, Jim is joined by Cici to discuss the three levers of value creation - risk mitigation, revenue growth, and cost reduction, and how we think about the three in the portfolio. Jimmy joins as well to add the People dimension.

Building Effective Teams and Healthy Organizations 14.01.2020

On this episode, Keith Hadley from the Table Group joins Paul Stansik to chat about how we build aligned C-suite teams and healthy portfolio companies. We cover what healthy organizations do differently, why most team offsites are not time well spent, and how to tell if you're on (or leading) a dysfunctional team.

2020 Predictions Show 07.01.2020

Devin and Jim kick off the new year with our annual predictions episode.  Come have a listen as we opine on what 2020 has in store for Private Equity.

Interview with Stacey Kacek, CEO of OnePlus Systems 13.12.2019

Jimmy Holloran talks with Stacey Kacek, OnePlus Systems CEO. They discuss her early career as an engineer at Motorola, her transition into leadership, and her perspective on being a CEO. Along the way, they cover key influences in her life, lessons learned, and as well as advice for aspiring CEOs.

When process automation misses the mark 03.12.2019

Jim recently got massively over-billed by Hertz, prompting a discussion about what happens to customers when process automation goes off the rails. Ryan Milligan jumps in with a Zappos story that will warm your heart.

How we use talent reviews, the 9box, and succession planning 22.11.2019

As part of our continuing People Operations series, ParkerGale Principals Jimmy and Paul dive into the 9box, a talent management framework commonly used to assess an organization's breadth and depth of talent. Jimmy and Paul cover why this matters, how to effectively review an organization's entire talent base, and why it pays for investors to be involved in the process.

You Need Win-Loss Analysis with Cici Zheng 15.11.2019

Devin sits down with Cici to discuss some easy but very important things you should be doing to extract deeper customer and market insight into your software products.

Inside the Deal - Three perspectives on how a deal gets done 06.11.2019

Partner Ryan Milligan talks with Mike Trasatti, CEO of DealerBuilt and Bill Lamm of Presidio Technology Partners about how a deal really gets done. Covering everything from the banker signing up to represent DealerBuilt to ParkerGale courting and successfully completing the deal with management.

Strategies for Technology Transitions 30.10.2019

Come have a listen as Stephen Tallamy CTO of EditShare talks about strategies for making technology transitions for complicated software platforms.

Hiring Technical Leaders for Non-Technical People 15.10.2019

Hiring technical people is hard when you don't know all the buzzwords and acronyms. Devin and Jim help you with good process and some helpful questions to ask when you are hiring Engineering and Software Development leaders.

Tom Obermaier Interview 27.09.2019

Continuing our on-going series of interviews with ParkerGale portfolio company CEOs, Jimmy interviews Tom Obermaier, CEO of Rippe and Kingston. We talk baseball, growing up in New York, leadership lessons from President Washington, rising to Chief Risk Officer at Citi Bank at the time of the financial crisis, and his evolution as a CEO at RDC and Rippe.

A Brief History of Software with Tom Shore 20.09.2019

Jim talks with fellow Babson College Alum, current portfolio company CTO, Tom Shore about application software from the early 80s through today.  We talk Digital Equipment PDP/11s all the way through the current no-code fascination.

Kara Master Interview 13.09.2019

We talk to PG Principal Kara Master about her journey from the model UN and a career in journalism to joining the deal team at ParkerGale.

Things to Avoid in Selecting an Executive Job with Dave Kellogg 23.08.2019

Buckle your seatbelts for a fast-paced conversation with Dave Kellogg. Dave and I first met back in the early 80s at Ingres, when I was a pre-sales engineer and Dave was a technical support rep. We've each spent over 25 years in enterprise software, in mixed roles that involve both technology and sales & marketing. We reconnected recently and met up up in Chicago at ParkerGale's "intergalactic hea...

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