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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Instagram: https://www.instagram.com/chris_mailander_podcast/
https://www.podcast.chrismailander.com/
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Original Music by Billy Goodrum

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

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

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

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