Mailander Podcast

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 wher...

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, bu...

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 co...

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...

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...

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...

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,...

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, inc...

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...

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...

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 t...

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...

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 o...

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...

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...

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 delibera...

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 dec...

Elite CEOs and companies do not shy away from the noise, confusion, and chaos of shifting markets. Instead, they study them. They move their assets and players into place. They place a mark on others, including those less savvy, stuck in their mindset, unable to move, or simply certain they are right, because they always were before. If played well, they emerge even stronger in the end. This is a...

This is the story of a U.S. Navy nuclear submarine commander’s ability to challenge the Soviets when they were at their weakest. He changed the rules of the game.  And won.  He secured asymmetric advantage, but for a moment. It was by targeting the decision-making weaknesses of his Soviet nuclear counterparts for but a moment. The Cold War ended three years after his exploits.  This is a story pie...

Many CEOs believe their strategic success depends on the strength of their product, service, technology, financing, or branding. In reality, however, the most powerful asset available to the CEO in leading a company’s strategic execution is the process by which they make decisions. The process determines the outcome. A former parliamentarian in the U.S. House of Representations, who would go on la...

The seeds of decision-making success or failure are planted years before we witness the climactic result.  Four common CEO archetypes are at risk of getting their decision wrong when it will matter most.  There is a myth that there are singular moments of brilliance or failure in CEO decision-making.  It is the climactic high point in the stories we tell and movies we watch. More often than not, i...

Identify the red flags that CEOs can look for in targeting the decision-making of opponents, as well as to overcome in their own decision-making patterns and tendencies through an exploration of how one of the most influential captains of a venerable institution went to stewarding one of the most profitable financial engines on Wall Street to overseeing its demise. Joe Cassano was CEO of AIG Finan...

Sound CEO decision-making is fundamentally rooted in a willingness to persistently challenge the dominant logic and narrative that runs in your mind. This is my story of getting hit in a blind spot. These moments hurt. They are remembered. This is where some of our greatest learnings can come from. Mailander learned a hard lesson while building a Silicon Valley technology company. Like many execut...

Leverage these three core tenets for enabling your company to level up against the next higher level of competition. Drawn from the experience of working with a mid-market leader that was successful, had more ceiling with their current business, but for the young CEO, could reach so much higher, this episode reveals three core tenets to competing at a higher level.   When leveling up to enable you...

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, ha...