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)

Sam Kendree | Inside the $84 Trillion Wealth Shift No One Is Ready For

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 w...

20 Nov 202546min

Monica Marquez | From Goldman Sachs & Google to Founder: The AI Mindset Shift Nobody's Making

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 do...

28 Okt 202539min

Ethan Monkhouse | Inside AI that Can Read Minds: When Technology Sees What You Hide

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 p...

5 Aug 202555min

Eli Portnoy | Exit Playbook: Founder Reveals His Recipe for Selling Tech Companies

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 millio...

10 Jun 202545min

Ryan Davis | Winning in the Attention Economy; Trump; Musk; Mayor Pete; CEOs as Chief Influencers

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 ...

20 Mai 202545min

Billy Goodrum Talks Dumb & Dumber, Something About Mary, Sophia Loren - Life as a Hollywood Composer

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,” ...

6 Mar 202545min

Josh Gilbert & Gopal Erinjippurath | Geospatial AI | Reshaping Climate Prediction & Global Power

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, co-fo...

9 Jan 20251h 21min

Andrew Jones: Global Thinker | Complex Decision-Making | Climate Interactive

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 ramifica...

30 Des 20241h 4min

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