A-ha with Chris Mailander

About A-ha with Chris Mailander

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.

Publisher

Chris Mailander

Category

business

Language

en

Explicit

No

First episode

3 Nov 2023

Latest episode

20 Nov 2025

Latest episodes

27 episodes in the feed.

1. 

   20 Nov 2025

   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 of WealthFeed, about why a $30B+ S&P 500 company like Broadridge chose to back a nine-person startup with a strategic investment, and what that says about where wealth management is really headed. Sam breaks down the reality behind this slow-moving syste...

2. 

   28 Oct 2025

   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 environment. What she discovered became the foundation of Flipwork: Organizations fail during transformation not because the technology is wrong, but because people can't change fast enough. The irony is sharp. Companies invest millions in AI and then wo...

3. 

   5 Aug 2025

   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, and even childhood trauma from social media behavior alone. Ethan discovered his technology was becoming immensely powerful. In this fascinating conversation, we explore the cutting edge of AI psychological profiling - technology that can read between t...

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

7 ratings

Spotify

5.0 / 5

5 ratings

Podcast Authority Score: 43 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

48

Social presence

90

YouTube

0

Engagement

51

Contact A-ha with Chris Mailander

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.