Middle Market Growth

The episode contains a handful of genuinely useful operational ideas - the parallel wind-down process and the 'unsub' indenture maneuver being the standouts - but is padded with a walk-up song segment, promotional content, and a lot of generic framing ('maximize value,' 'management teams are set up for growth') that dilutes the density across 21 minutes.

“we actually bought the subsidiary for a dollar and in so doing unsubbed the subsidiary, which means that it was no longer defined as a capital S subsidiary under its indenture”

“if you can try to set up a parallel process for winding the subsidiary down in the event that the sale process is not effective”

The indenture 'unsub' mechanism and the parallel-process advice are genuinely non-obvious to most operators, but the broader framing - sell first, wind down is hard, management hates contraction - is standard restructuring wisdom recycled without a fresh angle.

“we actually bought the subsidiary for a dollar and in so doing unsubbed the subsidiary”

“maximizing the revenues while eliminating cost because both of those factors provide the value when you're shutting something down”

Eric Kaupp is a genuine deal practitioner - 20 years of in-house restructuring experience at Hilco, previously at Skadden - who has actually executed the transactions he describes; however, his perspective is inherently self-promotional and he represents one firm's approach rather than a broader operator perspective.

“I came here in January of 2004 as a lawyer straight from the restructuring group at the Chicago office of Skadden Arps. I was the lawyer in house lawyer at Hillco until January of 2024. So 20 full years”

“we were able to sell six of the nine businesses to individual buyers of those individual businesses”

The Pitney Bowes case study is meaningfully specific - named company, $100M annual losses, 13 facilities, 1,500 employees, $1 purchase price, zero bankruptcy claims, half-budget and two-thirds-time delivery, stock movement from ~$6 to $17 - which is strong for a 21-minute episode, though the Design Group Americas example is much thinner.

“we came in about about half of their budget, what they had internally budgeted for shutting down this division and probably two thirds of the time”

“the stock price of Pitney Bowes was something in uh, five, just, just under $6 a share when we did the transaction and it's been as high as 17 in the last couple months”

The host asks reasonable scene-setting questions and occasionally surfaces a useful angle ('why can an outside partner be better positioned?'), but never challenges Hilco's self-serving claims, skips over technical details worth probing (the indenture mechanics, what the chapter 11 filing actually cost), and opens with an irrelevant walk-up song question that wastes time.

“if you had to choose any walk up song, what would it be?”

“Why can an outside partner sometimes be better positioned to execute either a complex separation or a wind down than maybe the parent company handling that process itself”