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
Sam Kendree | Inside the $84 Trillion Wealth Shift No One Is Ready For
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
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
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Original Music by Billy Goodrum