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

Mailander Podcast is a business podcast hosted by Chris Mailander, with 27 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Chris Mailander hosts Mailander Podcast, a business show with 27 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Mailander Podcast

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

  Nov 20, 202547 minS0

  <p>The wealth management industry manages trillions — yet underneath the surface, it still runs on Zillow searches, handwritten notes, and decades-old workflows.<br/><br/>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.<br/><br/>Sam breaks down the reality behind this slow-moving system — and why the coming $84 trillion wealth transfer could fundamentally reshape who wins and who disappears.<br/><br/>From private equity flooding the spac...

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  Mailander Podcast

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

  Oct 28, 202539 minS0

  <p>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.<br/><br/>The irony is sharp. Companies invest millions in AI and then wonder why adoption stalls. The workflows are better. The tools are more powerful. But humans have deep resistance to disrupting the way th...

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  Mailander Podcast

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

  Aug 5, 202555 minS0

  <p>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.<br/><br/>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 the lines of your digital presence to understand who you really are beneath your public persona.<br/><br/>From analyzing posture, object placement, speech patterns to...

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  Mailander Podcast

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

  Jun 10, 202545 minS0

  <p>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. This conversation is an insider’s look into his playbook, revealing the specific strategies he uses to build highly acquirable companies from the ground up.<br/><br/>The discussion explores Eli's core philosophies: that companies are bought, not sold, and that influencing an acquirer’s vision is more powerful than chasing it. He details his strategy of building relationships with potential buyers year...

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  Mailander Podcast

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

  May 20, 202545 minS0

  <p>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 traditional celebrity endorsements to a more decentralized approach, where authenticity and audience engagement are key. The conversation also touches on the role of AI in personalizing campaign messaging and the importance of navigating the new media landscape for candidates. In this conversation, Chris Mailander and Ryan Davis explore the dynamics of the creator economy, discussing the economics of influencer marketing, the intersection of...

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