In this deep dive, we unpack the operating philosophy of Joe Liemandt - builder of Trilogy Software and ESW Capital, and now the force behind Alpha School - including lessons from 100+ acquisitions. Liemandt became a billionaire by buying sleepy software assets and turning them into cash machines, vanished from public view for years, then re-emerged with a mission to rebuild systems from first principles. This episode isn’t about education - it’s about how great operators think.

The Sponsor
This episode is brought to you by CapitalPad. A marketplace that connects acquisition entrepreneurs who need capital with investors who want exposure to small-business deals. Standardized terms, governance, and distributions included. If you’re raising for a deal - or want to back operators - check out https://capitalpad.com/

Timestamps
00:00 Intro: Who is Joe Liemandt & why this episode
01:16 The real job of a boss: raise the bar
03:25 Reality-distortion & Trilogy’s elite culture
06:44 Expect more than they expect of themselves
08:46 ESW Capital’s “insane” bet: buying legacy software
09:20 Sponsor: CapitalPad
12:47 Pricing power: why most companies undercharge
14:33 Value-based pricing: the ESW playbook
16:15 Pricing moats
17:56 The real bottleneck: motivation vs information
19:48 Hiring for fire
21:27 Inner scorecard
23:12 Information is commodity; motivation is scarcity
24:45 Leaders as motivators
26:10 Systems that reward curiosity, not compliance
27:06 Closing framework: light the fire
27:55 “Customers have the answers” - sit with end users

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