Mailander Podcast

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.

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Episoder(27)

2024 Unveiled: CEO Strategies for Decoding Unfolding Systemic Shifts

2024 Unveiled: CEO Strategies for Decoding Unfolding Systemic Shifts

Explore the rules and pitfalls of decision-making amidst the significant systemic shifts we will likely see in 2024. From significant economic change, to the chaos of being a presidential election yea...

19 Nov 20237min

Place the Mark: The Great Chess Match Between Goldman Sachs and AIG (2005-2008)

Place the Mark: The Great Chess Match Between Goldman Sachs and AIG (2005-2008)

Elite CEOs and companies do not shy away from the noise, confusion, and chaos of shifting markets. Instead, they study them. They move their assets and players into place. They place a mark on others,...

3 Nov 20236min

Spotting Weakness: How a U.S. Nuclear Sub Commander Changed the Game

Spotting Weakness: How a U.S. Nuclear Sub Commander Changed the Game

This is the story of a U.S. Navy nuclear submarine commander’s ability to challenge the Soviets when they were at their weakest. He changed the rules of the game. And won. He secured asymmetric adva...

3 Nov 20238min

Process Determines Outcome: Teachings from a U.S. House of Representatives Parliamentarian

Process Determines Outcome: Teachings from a U.S. House of Representatives Parliamentarian

Many CEOs believe their strategic success depends on the strength of their product, service, technology, financing, or branding. In reality, however, the most powerful asset available to the CEO in le...

3 Nov 20232min

Worst Decision-Making: Myth Versus Reality

Worst Decision-Making: Myth Versus Reality

The seeds of decision-making success or failure are planted years before we witness the climactic result. Four common CEO archetypes are at risk of getting their decision wrong when it will matter mo...

3 Nov 20234min

Target Blind Spots: How a Wall Street Captain Was Exposed

Target Blind Spots: How a Wall Street Captain Was Exposed

Identify the red flags that CEOs can look for in targeting the decision-making of opponents, as well as to overcome in their own decision-making patterns and tendencies through an exploration of how o...

3 Nov 20234min

My Blind Spot: Hard Lessons Learned Painfully Well

My Blind Spot: Hard Lessons Learned Painfully Well

Sound CEO decision-making is fundamentally rooted in a willingness to persistently challenge the dominant logic and narrative that runs in your mind. This is my story of getting hit in a blind spot. T...

3 Nov 20234min

Compete Higher: Three Core Tenets for Leveling Up

Compete Higher: Three Core Tenets for Leveling Up

Leverage these three core tenets for enabling your company to level up against the next higher level of competition. Drawn from the experience of working with a mid-market leader that was successful...

3 Nov 20234min

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