Claim OwnershipMailander Podcast
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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.
27 Episodes
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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 syste...
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 wo...
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 t...
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...
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 lan...
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 c...
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 environme...
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 multinatio...
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, w...
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 inv...
Are you giving your greatest decisions the time they deserve? Short-term decisions are easy—they fit into neat timelines with clear metrics. But when it comes to the decisions that will most significantly impact your company's long-term future, you need to be willing to think differently, break the rules, and allow ideas to evolve. The best leaders know that patience and a bit of chaos have the greatest benefit. If you’re ready to rethink how you plan for the future, I’ll show you how to inte...
What do card games with Grandma and corporate strategy have in common? They're both high-stakes games of deception and decoding how the other player thinks. Beneath the surface lies a battle of wits, where every move is calculated to win. But how do you decipher the moves of your competitors and partners? Join me to learn how to outsmart Grandma and apply the same techniques to your corporate strategy. By decoding the DNA of decision-making, you'll gain a strategic advantage and pave the way ...
This is a story about an admiral unlike any other. Admiral Rickover was no ordinary leader. He was the architect of the US Nuclear Navy. How did he pull off the feat of creating asymmetric power for the United States through technological leadership? He did so not as a traditional military leader, but instead by rewriting the rules for driving transformational change. We now stand on the brink of a new technologically-driven era, fueled by the mysterious potential of artificial i...
Underdogs. We revel in them. We identify with them. Their stories become ours. They are the clever ones who find innovative ways to achieve victory over the bigger and stronger. The methods of the underdog apply equally well to the private companies and innovators seeking to compete with their much larger brethren. For those CEOs and management teams seeking extraordinary outcomes, the methods of the underdog may be their most effective method for competing. Underdogs do not win by re...
Volatility. It is often feared by leaders and decision-makers. In reality, it is a powerful gift. As we gear up for 2024, learn the art of perceiving and embracing change -- a skill essential for leaders, CEOs, and decision-makers navigating today's dynamic business landscape. Key Insights: Strategic Perception: Master the ability to perceive and respond to changing conditions, shifting your focus from anticipating the nature of surprises to adeptly navigating evolving landscapes. Te...
Imagine yourself in the Oval Office. Eighteen months before, you suffered a debacle that will come to mark the low point of your presidency. Your poor decision-making then changed the game, and not in your favor. Castro got stronger. The Soviets were emboldened to challenge you. Your reputation as a statesman on the international stage was damaged. Now, the young JFK was at the center of deliberations surrounding the most pressing threat. Soviet ships were shuttling nuclear weapons acro...
Explore the rules and pitfalls of decision-making amidst the significant systemic shifts we will likely see in 2024. From significant economic change, to the chaos of being a presidential election year, to a shifting global security and power framework, uncover your strategies for navigating these uncertainties which lie ahead in this thought-provoking episode. Dive into the intricate world of decision-making during systemic shifts with this episode. We dissect the pivotal moments unfolding i...
A quick exercise for CEOs to better understand how their decision-making is influenced by key actors, both in overt and subtle ways. In this excerpt from Decidedly, a podcast focused on helping private company CEOs, family offices, and HNWs manage their wealth, Mailander describes a process for revealing the subtle but profound influences on your own decision-making. It is an exercise frequently used with CEOs who are members of YPO in a workshop format. The exercis...
There is a fight for influence over your decision-making process amongst your internal teams. This is how to curate a healthy fight, and harvest its benefits for your company. There are competitors amongst those on your team who fight for influence over your decision-making. The battle can be overt, passive-aggressive, or quite subtle. It can be unhealthy. If curated well, it can be very healthy to your stewardship of the company. There will be several camps. In one, there is a...
Leverage the methods and mindset of the short sellers that hunt mistakes in judgment by CEOs in the public markets to strengthen the decision-making of companies in the private markets. This is a technique that CEOs and boards of directors can use to test both public and private companies’ decision-making prowess. It leverages the methods of short sellers, who hunt for companies to bet against, harvesting large gains from the mistakes of others. For this reason, short sellers are not popular...
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