Mailander Podcast

Hosted by Chris Mailander

Business Management

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Latest episode

Nov 2025

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EN-US

About the show

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.

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27 recent

November 20, 202546 min

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 endsChapters:00:00 Transforming Wealth Management with Technology03:00 The Crisis in Financial Advising06:05 Revolutionizing Client Acquisition08:57 AI's Role in Wealth Management11:48 Personalization in Financial Outreach14:52 The Future of Wealth Management17:45 Navigating the AI Landscape20:50 The Old Guard vs. New School in Finance23:42 The Evolution of Trust in Financial Relationships25:56 The Impact of AI on Consumer Expectations29:13 Robinhood's Influence on Wealth Management32:21 WealthFeed's Role in the Financial Landscape35:26 Navigating Partnerships in Wealth Management43:06 Forecasting the Future of Wealth Management___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

October 28, 202539 min

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 AIChapters:00:00 Transforming Work with AI09:55 The Human Element in AI Adoption20:08 Reinventing the Playbook for Success29:58 Diversity and ROI: A New Perspective39:08 Personal Journeys and Embracing Change___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

August 5, 202555 min

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 managementHow 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 surveillanceChapters:00:00 The Power of AI in Personal Profiling02:56 Navigating the Edge of Technology06:07 Understanding Psychological Profiles08:49 The Process of Fine-Tuning AI Models11:51 Evaluating AI Responses14:50 The Role of Trust in Marketing17:41 Identifying Super Fans in Music21:05 The Dynamics of Fan Engagement23:57 The Future of AI in Marketing26:41 Ethics and Responsibility in AI29:52 The Evolution of Engineering Roles33:02 Trust as a Key Factor in Business___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

June 10, 202545 min

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 Acquirers02:16 Building Valuable Companies08:06 The Importance of Relationships16:16 Timing and Market Conditions18:15 Valuation in Illiquid Markets23:30 The Importance of Founder-Led Sales26:04 Scaling Sales Efforts28:11 Navigating Pivots in Startups31:20 The Emotional Roller Coaster of Entrepreneurship32:41 The Draw of Entrepreneurship35:31 Adapting to Rapid Market Changes38:20 The Role of Venture Capital in Startups41:07 Building Back Engine AI: A New Venture___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

May 20, 202545 min

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 Marketing03:10 Understanding Influencer Marketing Today10:10 The Impact of the Attention Economy12:40 Navigating the New Media Landscape19:40 Emerging Candidates and Strategies for 202822:40 The Role of AI in Future Campaigns25:43 The Economics of the Creator Economy28:50 Navigating Political and Commercial Content34:52 The Digital Nomad Perspective38:25 Leveraging Technology and AI in Marketing41:41 Addressing Potential Abuses in the Creator Economy___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

March 6, 202545 min

Billy Goodrum Talks Dumb & Dumber, Something About Mary, Sophia Loren - Life as a Hollywood Composer

Step into the private studio of Hollywood composer Billy Goodrum as he shares the creative secrets behind some of comedy's most iconic films. From crafting the memorable music for “Dumb and Dumber,” “There’s Something About Mary,” and countless other Farrelly Brothers classics to collaborating with Sophia Loren’s son on award-winning international projects, Goodrum offers a rare glimpse into the collaborative genius of film composition.In this intimate conversation, discover:• How a chance meeting and “Two Foot of Butt Crack” launched Goodrum’s Hollywood career• The subtle art of film scoring and how he helps create compelling experiences for his audiences• His transition from composer to screenwriter with “How to Die in the South” and other screenplays in development• The stark differences collaborating with American comedy directors versus European auteursThis episode delivers fascinating insights into how sound is used to create the experiences that make us laugh, cry, and feel. There’s even an ‘easter egg’ towards the end that helps demonstrate how Billy translates abstract concepts into tangible compositions that shape how we engage with an experience. Enjoy! ___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

January 9, 20251 hr 21 min

Josh Gilbert & Gopal Erinjippurath | Geospatial AI | Reshaping Climate Prediction & Global Power

In an era where AI giants like Palantir, Google, Microsoft, and NVIDIA battle for supremacy, a new frontier is emerging: the race to predict Earth's future. Josh Gilbert and Gopal Erinjippurath, co-founders of Sust Global, reveal how geospatial AI is becoming the next critical battleground in the global tech war. Drawing parallels to the nuclear arms race, they explore how major tech players, defense contractors, and financial institutions are competing to harness vast satellite and environmental datasets to predict everything from hurricane paths to economic shockwaves. This episode pulls back the curtain on how AI is revolutionizing climate risk prediction and reshaping global power dynamics. Josh and Gopal share insider insights on which tech giants might win or lose in this trillion-dollar race, and how geospatial AI is giving decision-makers unprecedented ability to anticipate and respond to environmental and economic threats. Learn how this technological arms race is transforming not just how we understand our planet, but how nations and corporations will compete in an AI-driven future.Key takeawaysGeospatial AI is the next frontier: Just like language models transformed text, geospatial AI will revolutionize how we understand and interact with the physical world.Data is the new oil, but spatial context is the refinery: Raw data is abundant, butextracting meaningful insights requires understanding the spatial relationships within that data.The race is on: Companies like Palantir are already dominating this space, but there's still room for innovative startups to carve out niches and disrupt the market.The future is multimodal: Combining geospatial data with other data sources like financial, social, and climate data will unlock unprecedented levels of insight.Human-in-the-loop is evolving: The future of geospatial AI involves intelligent agents that can autonomously analyze data and generate actionable insights, minimizing the need for human intervention.Visit Sust Global here: https://www.sustglobal.com/___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/___________________________________Original Music by Billy Goodrum___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

December 30, 20241 hr 4 min

Andrew Jones: Global Thinker | Complex Decision-Making | Climate Interactive

Andrew Jones is one of the foremost experts on the use of simulation modeling to improve decision-making for our most pressing global challenges, including the socio-economic and geopolitical ramifications of climate change. He is Co-Founder and CEO of Climate Interactive, and creator of the En-ROADS simulation model which has been used by an estimated 1.4 million people in over 170 countries, including by global negotiators, U.S. Senators and more than 178 Members of Congress, and multinational corporations. In this episode, filmed in Asheville, North Carolina, following the devastation of Hurricane Helene, we explore how system dynamics modeling, simulations, and synthetic experiences can be used to help policymakers and decision-makers to better conceptualize and understand the myriad dimensions of complex problems. Jones reveals methods and strategies for overcoming the challenges of time and space in order to visual future outcomes within milliseconds, creating non-judgmental environments for exploring alternative options, and avoiding reliance on ‘black box’ modeling to instead use methodologies which transparently reveal the dynamic cross-correlations at play within complex systems.___________________________________You too can directly work with the simulation model discussed in this podcast (available for free and in 20 languages) by going to https://www.climateinteractive.org/en-roads/ . You can connect with Andrew Jones here: https://www.climateinteractive.org/about/staff/andrew-p-jones/ .___________________________________Original Music by Billy GoodrumWatch on Youtube: https://youtu.be/6VaJ9xhvEG0___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

November 26, 20241 hr 45 min

Jan Jensen: Iowa WBB; Caitlin Clark; Building an Elite Program; The New College Athlete

Jan Jensen is the new head coach for women’s basketball at the University of Iowa. Jensen takes over an elite program that developed generational phenom, Caitlin Clark (WNBA Rookie of the Year with the Indiana Fever), and reached the NCAA Championship game the last two years. Previously named NCAA Assistant Coach of the Year, Jensen has been instrumental in recruiting and developing such athletes as Kate Martin (now with the Las Vegas Aces) and Megan Gustafson (also with the Las Vegas Aces, who recently competed for Spain in the 2024 Paris Olympics, and was NCAA Player of the Year while at Iowa). Our conversation discussed Jensen’s succession path following Lisa Bluder; her vision for the team under her leadership; building and curating a team culture; recruiting the right players to fit the Iowa program; creating the conditions for developing confidence and trust; the changing realities of college athletics with NIL, the portal, and revenue sharing; the Iowa ‘brand’; and a few memories of growing up in Iowa’s small farm communities.___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

November 19, 20242 hr 36 min

Eliot Puplett | Fintech Founder on Entrepreneur’s Journey | Mailander Podcast

Tech entrepreneur Eliot Puplett shares his vision for democratizing global finance through blockchain technology. As founder of Medici, he's building a decentralized financial system that could do for money what the internet did for information. Puplett discusses the challenges of disrupting entrenched financial institutions, navigating regulatory hurdles, and building new infrastructure from scratch. He explains how blockchain can dramatically reduce costs and complexity in international investments by eliminating middlemen and creating transparent, immutable transactions. Beyond the technology, Puplett reveals his deeper mission: enabling thousands of people who've been excluded from traditional finance to build wealth, start companies, and access capital markets. It's a raw, candid conversation about fighting the status quo while trying to become part of it – and the messy reality of building a financial revolution from the ground up._______________________________________Original Music by Billy Goodrum___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum