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Mailander Podcast

Mailander Podcast

著者: Chris Mailander
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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.

© 2025 Mailander Podcast
マネジメント マネジメント・リーダーシップ 経済学
エピソード
  • Sam Kendree | Inside the $84 Trillion Wealth Shift No One Is Ready For
    2025/11/20

    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 system — and why the coming $84 trillion wealth transfer could fundamentally reshape who wins and who disappears.

    From private equity flooding the space, to AI “wrappers” overwhelming advisors, to a new generation that changes advisors within 12 months of inheriting wealth, this conversation pulls apart the forces reshaping one of the biggest, oldest, and least-changed industries in America.

    If you want to understand how wealth really moves — and why the next decade will not look like the last — this episode is essential.

    Key Moments
    • How wealth managers still source clients using Zillow and court filings
    • Why only 5–10% of advisors use modern prospecting tools
    • How AI is flooding the industry with low-quality tech
    • Why inheritors immediately fire their advisor
    • The $0–$5M segment no one is serving
    • Why “money in motion” is the real catalyst event
    • What WealthFeed’s five-click discovery model enables
    • What happens when the bull market ends

    Chapters:
    00:00 Transforming Wealth Management with Technology
    03:00 The Crisis in Financial Advising
    06:05 Revolutionizing Client Acquisition
    08:57 AI's Role in Wealth Management
    11:48 Personalization in Financial Outreach
    14:52 The Future of Wealth Management
    17:45 Navigating the AI Landscape
    20:50 The Old Guard vs. New School in Finance
    23:42 The Evolution of Trust in Financial Relationships
    25:56 The Impact of AI on Consumer Expectations
    29:13 Robinhood's Influence on Wealth Management
    32:21 WealthFeed's Role in the Financial Landscape
    35:26 Navigating Partnerships in Wealth Management
    43:06 Forecasting the Future of Wealth Management

    ___________________________________
    Socials:
    X: https://x.com/MailanderPod
    Instagram: https://www.instagram.com/chris_mailander_podcast/
    https://www.podcast.chrismailander.com/
    ___________________________________
    Original Music by Billy Goodrum

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    47 分
  • Monica Marquez | From Goldman Sachs & Google to Founder: The AI Mindset Shift Nobody's Making
    2025/10/28

    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 wonder why adoption stalls. The workflows are better. The tools are more powerful. But humans have deep resistance to disrupting the way they've always worked—especially when that work has made them successful for 10, 20, or 30 years.

    This episode explores the real frontier of AI adoption: The human element.
    Monica explains why "survival of the fittest" no longer applies. Now it's survival of the fastest. She breaks down what Flipwork actually does—helping teams flip outdated beliefs about work and build adaptive, human-centered cultures that can move with AI, not against it.

    She also reveals the hard truth: if you don't build internal capacity to adapt, smaller, leaner competitors will eat your lunch. The organizations that figure out how to upskill talent instead of replacing them will dominate the next three to five years.

    For leaders, managers, and anyone responsible for organizational change: This conversation is about the gap between what technology can do and what humans can actually embrace.

    Key Moments:
    • Why big tech companies are scratching their heads over flat AI adoption
    • The specific moves smaller companies are making that larger ones can't
    • How psychological safety unlocks real adoption
    • Why you have to disrupt yourself before you get disrupted
    • The compounding effect of impact vs. effort in the age of AI

    Chapters:
    00:00 Transforming Work with AI
    09:55 The Human Element in AI Adoption
    20:08 Reinventing the Playbook for Success
    29:58 Diversity and ROI: A New Perspective
    39:08 Personal Journeys and Embracing Change

    ___________________________________
    Socials:
    X: https://x.com/MailanderPod
    Instagram: https://www.instagram.com/chris_mailander_podcast/
    https://www.podcast.chrismailander.com/
    ___________________________________
    Original Music by Billy Goodrum

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    39 分
  • Ethan Monkhouse | Inside AI that Can Read Minds: When Technology Sees What You Hide
    2025/08/05

    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 the lines of your digital presence to understand who you really are beneath your public persona.

    From analyzing posture, object placement, speech patterns to other subtle hints, Ethan’s AI was able to detect his mild OCD, for example. It was something he’d never revealed publicly.

    We dive deep into how this technology works, its applications in marketing and fan identification, and the ethical considerations of building AI that can see through our carefully-crafted online personas.

    For Leaders, Strategists and Decision-Makers: Discover how Naviro AI replicated months of marketing strategy work in one hour, identified superfans with 99% accuracy, and helped music labels understand the psychological drivers behind fan behavior. But more importantly, understand what this means for the future of work and human privacy.

    This conversation sits at the intersection of technological possibility and human psychology - essential listening for anyone trying to understand where AI is headed and how to navigate its implications responsibly.

    Key Moments:

    • Real-world case study: How AI identified specific personal details Ethan had never shared publicly
    • Technical deep dive: Fine-tuning models, vector databases, and agent management
    • How music artists use AI to identify demographic groups as fans with the greatest lifetime value (LTV)
    • Crafting future organizational chart that place AI agents into key decision-making roles
    • Building responsible AI in an age of increasing surveillance


    Chapters:
    00:00 The Power of AI in Personal Profiling
    02:56 Navigating the Edge of Technology
    06:07 Understanding Psychological Profiles
    08:49 The Process of Fine-Tuning AI Models
    11:51 Evaluating AI Responses
    14:50 The Role of Trust in Marketing
    17:41 Identifying Super Fans in Music
    21:05 The Dynamics of Fan Engagement
    23:57 The Future of AI in Marketing
    26:41 Ethics and Responsibility in AI
    29:52 The Evolution of Engineering Roles
    33:02 Trust as a Key Factor in Business

    ___________________________________
    Socials:
    X: https://x.com/MailanderPod
    Instagram: https://www.instagram.com/chris_mailander_podcast/
    https://www.podcast.chrismailander.com/
    ___________________________________
    Original Music by Billy Goodrum

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    55 分
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