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

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 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

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 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

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 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

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

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. 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 years before a sale and unpacks the vital role of founder-led sales in building a truly valuable company. Beyond tactics, the conversation delves into the emotional reality of the startup journey, from the difficult lows and "moments of just absolute shit" to the incredible highs that provide the motivation to do it again. These lessons led to his latest venture, Back Engine AI, which was built to solve a core problem he faced: losing the "founder superpower" of deep customer connection as a company grows. It is his favorite company yet. Chapters: 00:00 The Mindset of Acquirers 02:16 Building Valuable Companies 08:06 The Importance of Relationships 16:16 Timing and Market Conditions 18:15 Valuation in Illiquid Markets 23:30 The Importance of Founder-Led Sales 26:04 Scaling Sales Efforts 28:11 Navigating Pivots in Startups 31:20 The Emotional Roller Coaster of Entrepreneurship 32:41 The Draw of Entrepreneurship 35:31 Adapting to Rapid Market Changes 38:20 The Role of Venture Capital in Startups 41:07 Building Back Engine AI: A New Venture ___________________________________ Socials: X: https://x.com/MailanderPod Instagram: https://www.instagram.com/chris_mailander_podcast/ https://www.podcast.chrismailander.com/ ___________________________________ Original Music by Billy Goodrum

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

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 political and commercial content, the perspective of a digital nomad, the role of technology and AI in marketing, and the potential abuses within the creator economy. They delve into how audience engagement varies with creator size, the evolving expectations of CEOs as influencers, and the implications of AI on content creation and authenticity. It is a broad ranging conversation, spanning President Trump’s media-first strategy, to Elon Musk, Gavin Newsome, Mayor Pete, Corey Booker, and political upstarts, all seeking to capture the moment with the right message on an rapidly evolving medium. Chapters: 00:00 The Evolution of Influencer Marketing 03:10 Understanding Influencer Marketing Today 10:10 The Impact of the Attention Economy 12:40 Navigating the New Media Landscape 19:40 Emerging Candidates and Strategies for 2028 22:40 The Role of AI in Future Campaigns 25:43 The Economics of the Creator Economy 28:50 Navigating Political and Commercial Content 34:52 The Digital Nomad Perspective 38:25 Leveraging Technology and AI in Marketing 41:41 Addressing Potential Abuses in the Creator Economy ___________________________________ Socials: X: https://x.com/MailanderPod Instagram: https://www.instagram.com/chris_mailander_podcast/ https://www.podcast.chrismailander.com/ ___________________________________ Original Music by Billy Goodrum