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About This 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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Recent Episodes
Sam Kendree | Inside the $84 Trillion Wealth Shift No One Is Ready For
The wealth management industry manages trillions — yet underneath the surface, it still runs on Zillow searches, handwritten notes, and decades-old workflows.In this episode, Chris Mailander talks…
Monica Marquez | From Goldman Sachs & Google to Founder: The AI Mindset Shift Nobody's Making
Monica Marquez has spent her career inside some of the world's most prestigious organizations—Goldman Sachs, Google, EY, Bank of America. She watched from the inside how these companies respond (or…
Ethan Monkhouse | Inside AI that Can Read Minds: When Technology Sees What You Hide
Ethan Monkhouse built AI technology so advanced at psychological profiling that he deemed it "too intense" for public release. As co-founder of Naviro AI, Ethan has created systems that can identify…
Eli Portnoy | Exit Playbook: Founder Reveals His Recipe for Selling Tech Companies
Meet Eli Portnoy, a serial entrepreneur who has done what few have: Founded and led two separate tech companies to successful eight-figure exits. He sold his first company, ThinkNear, for $22.5…
Ryan Davis | Winning in the Attention Economy; Trump; Musk; Mayor Pete; CEOs as Chief Influencers
In this conversation, Chris Mailander and Ryan Davis explore the evolution and current state of influencer marketing, its impact on political campaigns, and the future of media strategy. They discuss…
Billy Goodrum Talks Dumb & Dumber, Something About Mary, Sophia Loren - Life as a Hollywood Composer
Step into the private studio of Hollywood composer Billy Goodrum as he shares the creative secrets behind some of comedy's most iconic films. From crafting the memorable music for “Dumb and Dumber,”…
Josh Gilbert & Gopal Erinjippurath | Geospatial AI | Reshaping Climate Prediction & Global Power
In an era where AI giants like Palantir, Google, Microsoft, and NVIDIA battle for supremacy, a new frontier is emerging: the race to predict Earth's future. Josh Gilbert and Gopal Erinjippurath,…
Andrew Jones: Global Thinker | Complex Decision-Making | Climate Interactive
Andrew Jones is one of the foremost experts on the use of simulation modeling to improve decision-making for our most pressing global challenges, including the socio-economic and geopolitical…
Jan Jensen: Iowa WBB; Caitlin Clark; Building an Elite Program; The New College Athlete
Jan Jensen is the new head coach for women’s basketball at the University of Iowa. Jensen takes over an elite program that developed generational phenom, Caitlin Clark (WNBA Rookie of the Year with…
Eliot Puplett | Fintech Founder on Entrepreneur’s Journey | Mailander Podcast
Tech entrepreneur Eliot Puplett shares his vision for democratizing global finance through blockchain technology. As founder of Medici, he's building a decentralized financial system that could do…
Intention & Patience: Carefully Curate Your Decision Architecture
Are you giving your greatest decisions the time they deserve? Short-term decisions are easy—they fit into neat timelines with clear metrics. But when it comes to the decisions that will most…
Beat Grandma (The ’Tells’)
What do card games with Grandma and corporate strategy have in common? They're both high-stakes games of deception and decoding how the other player thinks. Beneath the surface lies a battle of wits,…
Epic Shifts: Lessons from Admiral Rickover on Leading Transformation
This is a story about an admiral unlike any other. Admiral Rickover was no ordinary leader. He was the architect of the US Nuclear Navy. How did he pull off the feat of creating asymmetric power for…
The Intangibles: Underdogs Embrace the Unconventional
Underdogs. We revel in them. We identify with them. Their stories become ours. They are the clever ones who find innovative ways to achieve victory over the bigger and stronger.The methods of the…
Volatility Is Your Gift
Volatility. It is often feared by leaders and decision-makers. In reality, it is a powerful gift. As we gear up for 2024, learn the art of perceiving and embracing change -- a skill essential for…
S1E12 Ideas vs. Power: The Lesson that Changed JFK
Imagine yourself in the Oval Office. Eighteen months before, you suffered a debacle that will come to mark the low point of your presidency. Your poor decision-making then changed the game, and not…
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…
S1E9 Curate Friction: The Good Fight You Should Be Having
There is a fight for influence over your decision-making process amongst your internal teams. This is how to curate a healthy fight, and harvest its benefits for your company. There are competitors…
Target Poor Judgment: Be a Short Seller
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…
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,…
Frequently Asked Questions
Mailander Podcast has published 27 episodes since November 2023, covering topics in Business, Management.
Mailander Podcast is currently moderate with new episodes every 2 months. Average episode length is 24m.
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