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
Target Poor Judgment: Be a Short Seller
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
Leverage the methods and mindset of the short sellers that hunt mistakes in judgment by CEOs in the public markets to strengthen the decision-making of companies in the private markets.
This is a technique that CEOs and boards of directors can use to test both public and private companies’ decision-making prowess. It leverages the methods of short sellers, who hunt for companies to bet against, harvesting large gains from the mistakes of others. For this reason, short sellers are not popular, but they play an important role. This technique is more fully outlined in my article in Directors & Boards in 2023.
For CEOs, as well as the boards of directors possessing a fiduciary duty to oversee management decision-making, the test helps identify potential errors of judgment along the way. Most commonly, the test is to identify the assumptions underlying the variables in the CEO’s decision-making ‘algorithm’. Then, modify the assumptions to determine the implication on the decision outcome.
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Original Music by Billy Goodrum