Mailander Podcast
The Mailander Podcast is a film room for high-stakes decisions.
In each episode, strategist and author Chris Mailander sits down with leaders who have been tested under real pressure to replay 2–3 pivotal choices that changed the trajectory of a company, career, or market.
The show is built around decision intelligence—the discipline of designing the processes, frameworks, and systems that make consequential choices better over time. Guests are typically CEOs of private mid-market companies (roughly $50M–$5B+ in revenue) or founders of AI and technology platforms (roughly $5M–$50M ARR) who have already navigated major inflection points: exits, strategic investments, AI transformations, turnarounds, or elite program builds.
Instead of surface-level origin stories, conversations slow the game down. Chris and his guests break down what they saw, what they missed, the trade-offs they wrestled with, and how those decisions shaped enterprise value, culture, and competitive advantage.
If you’re a performance-driven leader—CEO, investor, operator, or emerging founder—and you treat judgment as a craft, this is your room. Episodes are produced in long-form video and audio and released across Apple Podcasts, Spotify, Audible, YouTube, and major social channels, with selected clips cut for precision delivery to the audiences that matter most.
Mailander Podcast
Decision Bias: Find the Subtle Influences on Your Decision-Making
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A quick exercise for CEOs to better understand how their decision-making is influenced by key actors, both in overt and subtle ways.
In this excerpt from Decidedly, a podcast focused on helping private company CEOs, family offices, and HNWs manage their wealth, Mailander describes a process for revealing the subtle but profound influences on your own decision-making. It is an exercise frequently used with CEOs who are members of YPO in a workshop format.
The exercise involves identifying the overt objective the CEO seeks to attain – whether that be an M&A or exit from their business, a recapitalization, a reorganization, the pathway for generational succession, or to growth the company’s enterprise value to the greatest extent value. Then, the CEO is to identify the eight people (from both within the company or from the CEO’s personal life), which are most influential to how the CEO will think, perceive, and react to alternative pathways to achievement of the end goal.
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Original Music by Billy Goodrum