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
Latest 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 with Sam Kendree, CEO & Co-Founder ...
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 don't) to massive shifts in their operating en...
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 personality traits, psychological patterns, a...
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 million and his second, Sense360, for $44 million....
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 how influencer marketing has shifted from tr...