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 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

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

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

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

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

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

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

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

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

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

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 intentionally curate your company’s decision architecture to create the greatest long-term value. Let’s go to work. Key Takeaways:Patience is Key: Long-term decision-making requires patience, allowing ideas to develop and evolve without the pressure of immediate results.Embrace Cognitive Friction: Introducing and managing cognitive friction—deliberately challenging and deconstructing ideas—enhances decision-making and prepares teams for real-world challenges.Flexible Decision Architecture: Successful long-term strategies are built on a flexible, less rigid decision-making process that encourages creativity, experimentation, and non-linear thinking.Intentional Curation of Ideas: Curating ideas with intention, even when they seem illogical or irrational, can lead to innovative solutions that redefine your organization’s future.Avoid Over-Transparency: In long-term planning, being too transparent about desired outcomes can stifle creativity and lead to groupthink. Instead, allow space for new pathways and ideas to emerge organically.___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

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 for success in your leadership journey. Put yourself into position to play a winning hand?Key takeaways:Decoding Decision-Making: Just like reading Grandma's moves in a card game, understanding the conscious and unconscious decisions of competitors and partners is crucial in corporate strategy. By deciphering these patterns, leaders can anticipate future moves and gain a strategic advantage.Uncovering Subconscious Biases: It’s important to recognize not only the overt decisions but also the hidden biases and blind spots that influence behavior. Identifying these subconscious patterns allows leaders to make more informed decisions and navigate complex business environments with confidence.Enhancing Accuracy and Competitive Advantage: Improving the accuracy of decoding decision-making processes is essential for success in a competitive landscape. Through methods to enhance accuracy and minimize guesswork, leaders can better position themselves to capitalize on opportunities and navigate challenges effectively. Doing so is how a CEO plays at the highest levels of ’the game’.___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

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 intelligence. AI promises to change everything about how we think, live, and work, and as such fills many of us with tremendous fear and uncertainty about the implications. These potentially dramatic shifts in our future parallel those who experienced the early days of the nuclear era unfolding after WWII. Rickover stood at the forefront of harnessing nuclear technology in that era, and his story takes on new relevance now. More specifically, Rickover’s acumen as a leader lie in his ability to harness the potential of tremendous technological advancements, but in doing so by actually unlocking the potential of human minds. His journey shows us a path for rethinking our own decision-making, and embracing the change, not shrinking from it. Rickover’s story offers valuable insights into fostering innovation, leading with resilience, and unlocking human potential.  Key Takeaways: Embrace Unconventional Leadership: In an era defined by rapid change and uncertainty, traditional leadership models may no longer suffice. Learn from Admiral Rickover's unconventional approach to leadership, which emphasized creativity, innovation, and a willingness to challenge the status quo. By embracing unconventional leadership strategies, you can foster a culture of agility and adaptability within your organization, enabling you to thrive in an ever-evolving landscape.Test Your Resilience: The ability to navigate adversity and bounce back from setbacks is essential for success in today's volatile business environment. Take a page from Rickover's playbook and deliberately put yourself in challenging situations that test your resilience and decision-making under pressure. By actively seeking out opportunities to test your resilience, you can build the confidence and fortitude needed to weather any storm and emerge stronger on the other side.Foster Innovation: In an age where innovation is the lifeblood of business success, fostering a culture of creativity and experimentation is paramount. Follow Rickover's lead by encouraging passion, curiosity, and a willingness to think outside the box among your team members. By creating an environment that values innovation and rewards bold ideas, you can unleash the full potential of your organization and stay ahead of the curve in a rapidly evolving marketplace.Lead with Conviction: Effective leadership requires more than just a vision—it demands unwavering conviction and a steadfast commitment to seeing that vision through. Drawing inspiration from Rickover's resolute leadership style, strive to lead with clarity, purpose, and determination. By embodying conviction in your actions and decisions, you can inspire confidence, rally your team around a shared purpose, and navigate through uncertainty with confidence and resolve.___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

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 replicating the strategies of their larger competitors. They don’t have the money, market share, brand, teams, or domain expertise at their fingertips to go toe-to-toe. Instead, they must find a competitive edge. They need a unique angle. They need to hone the ‘intangibles’ within their competitive arsenal. In this episode, Chris shares his experience having grown up and played with athletes that reached the heights of the NFL and NBA, as well as others who now coach at the highest levels of competition in NCAA football and basketball. He also shares some of his experience growing up in rural Iowa. In each of the stories, the competitive strategies of the underdog are revealed that enable them to out-compete those that were bigger and stronger. Key lessons in this episode include:Underdogs lean into and hone their ‘intangibles’, those subtle but profound factors that give them advantage, including their vision, anticipation and intuition, as well as the cadence and rhythms of their team;   The intentionally curate their decision-making processes so that they are optimized for those critical moments in which they will be under pressure, the situational context is shifting, and the confusion is greatest. It is in these moments in which they can turn adversity into opportunity; and   CEOs, like coaches or managers, must curate an environment in which they are overtly working to improve the intangibles, including the ability of their teams to work under pressure, manage through confusion, effectively anticipate how their competition will behave under similar conditions and come to trust one another’s decision-making and actions under new and challenging circumstances.  ___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

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.Team Conditioning: Equip your team with the skills to not only weather uncertainty but to thrive in it. Overcome the natural inclination to perceive change as a threat, fostering a culture where volatility is viewed as an opportunity.Unlocking Opportunities: Explore why embracing volatility can position your organization not just to survive but to emerge stronger. A comprehensive analysis demonstrates the long-term benefits for companies adept at navigating uncertainty.Dual Clock Management: Gain insights into managing the dual clocks of long-term strategy and short-term challenges. Learn how simultaneous navigation of both timelines empowers informed decision-making.Financial Preparedness: Uncover the critical importance of a robust balance sheet, essential for seizing strategic opportunities in times of uncertainty.Your Imperative as a Decision-Maker: Embrace the unpredictability of 2024. Instead of dwelling on the nature of surprises, focus on fortifying your organization to leverage the opportunities intrinsic to volatility. Join the discourse on strategic decision-making, financial preparedness, and transforming surprises into triumphs. Are you prepared to unlock the potential within volatility?___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

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 across the Atlantic towards Cuba. They threatened establish nuclear capabilities within lethal range of 80 million Americans. The fate of the world was on JFK’s shoulders. His track record so far was poor. Today's CEOs and leaders, like JFK, must similarly navigate a constant barrage of decisions which will affect the future of their organizations, their people, and their legacy. The fundamental question in these moments is how to get the decisions right when it will matter the most? JFK’s most profound lesson in his young presidency rooted in his ability to fundamentally re-architect his decision-making processes. He did so in the short span of 18 months. As a result, he moved from the low point of his presidency – the decision-making failures associated with the Bay of Pigs fiasco – to its high point: the blockade of Cuba. Building on the lessons learned in critical moments by leaders like JFK, in this episode learn how you can similarly: Architect Your Decision-Making Processes: Enhance your decision-making process by incorporating diverse perspectives and fostering open debate;Unleash the Power of Your Team: Unleash the potential of your team members by focusing on the quality of ideas they create rather than the allocation of power amongst them.Build a Resilient Organization: Cultivate an environment where ideas flourish, innovation thrives, and teams come to trust the process.JFK had to learn several tough lessons quickly. He rearchitected his own decision-making patterns. He challenged the ‘smart guys’ on his team to compete in new ways. He architected a process that yielded more options, superior risk analysis, and higher probabilities of success for those moments when they matter the most. These are the lessons CEOs and executive leaders can similarly learn well in advance of their own most critical decisions. ___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

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 in 2024 which will reshape industries, economies, and the way we work. Learn the two fundamental rules that dictate decisions when situational contexts shift, paving the way for three crucial lessons for CEOs and decision-makers.2024 is on the horizon, marked by high interest rates, personal debt spikes, and a tumultuous presidential election, all set to reshape the economic landscape. Corporate debt, government spending, and global events add layers to the shifting ground, presenting opportunities and challenges for businesses.Discover the common errors CEOs make in the wake of systemic shifts—immovable narratives, a lack of understanding about the evolving battlefield, and succumbing to emotional responses. The antidote? Proper planning, options analysis, and playbook development to navigate uncertainties.Your assignment? Identify the major systemic shifts for 2024 and plan accordingly. This episode serves as your guide, offering strategic insights to forecast winners and losers, steering your ship toward success in the face of evolving circumstances. Tune in for a thought-provoking exploration of the rules that govern decisions and the lessons that shape destinies.___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

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 exercise involves identifying the overt objective the CEO seeks to attain – whether that be an M&A or exit from their business, a recapitalization, a reorganization, the pathway for generational succession, or to growth the company’s enterprise value to the greatest extent value.   Then, the CEO is to identify the eight people (from both within the company or from the CEO’s personal life), which are most influential to how the CEO will think, perceive, and react to alternative pathways to achievement of the end goal.  ___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

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 strong preference for creating routine rhythms to the decision-making in the company, with a routine cadence, common language, and well-defined metrics.  In another, the preference is for the sort of irregularity where creative, innovation, and risk mitigation flourishes.  One wants patterns to work within. The other prefers no patterns at all.  They are both necessary and essential to the organization. The friction between these camps should be carefully curated to ensure each contributes well to the overall decision-making prowess of the company. Doing so leads to improved argumentation, better options analysis, stronger playbooks, the development of more diverse decision arcs, the ability to find the lines that blur between emotion and logic, and perhaps most importantly, the ability to evaluate how individual contributors think, react, and perceive.  For the CEO, key components for curating this friction include Intentionally observing and managing this process; Managing the ‘blend’ between those who flourish in regularized decision-making versus those who prefer irregular ones; and Measuring the performance of each camp, which for the former can be evaluated against MoM or QoQ financial performance and operational efficiency, and for the latter, which can be measured by their contribution to sustained increase in the long-term enterprise value of the company, able to both capture emergent new opportunities as well as forestall the risks that lurk beyond.___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

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, but they play an important role. This technique is more fully outlined in my article in Directors & Boards in 2023. For CEOs, as well as the boards of directors possessing a fiduciary duty to oversee management decision-making, the test helps identify potential errors of judgment along the way.  Most commonly, the test is to identify the assumptions underlying the variables in the CEO’s decision-making ‘algorithm’. Then, modify the assumptions to determine the implication on the decision outcome.  ___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

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 your company to play against the big boys, the nature of the competition and how they protect their positions can be awe-striking for the emerging company. Three core tenets for for discovering how to level up and compete higher include:Identify the Trophy Sought. You might be in a competition with a player or players whose end goal is quite different than your own. You might be hunting for increased sales, market share, or enterprise value appreciation. They might seek enhancements to their free cash flow or net-after-tax yield.  The different trophies being sought means they play the game in very different ways, and the decisions they will make for getting there will be quite different.  Domain Expertise. Dominant competitors leverage better financing capabilities. They have well-seasoned executive and middle management teams. They leverage the best lawyers, accountants, tax advisors, and management consultants, all of which are privy to the subtle ways of creating more value and impenetrable positions for their clients. Find an Edge. Rarely can a smaller competitor take on a larger competitor in a head-on assault, meaning it is hard to beat an established player at their own game. It is imperative for the smaller player or challenger to find their unique edge – some strategy that creates asymmetric advantage, even if for but a moment – whereby it can exploit a vulnerability of the competitor.  Very often, that edge will root down into the decision-making acumen of the players.  It can be one of the most profound and cost-effective means for leveling up.___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

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 executives on a string of success, the quest is to keep chalking up the wins, all in hope for achieving the beautiful prize in the end, which in the case of a tech company, is most likely its eventual sale to one of the 'big boys’. Navigating a corporate spin-out, initial funding, building deep teams across all disciplines, putting the right partners into the company to help it achieve its growth and credibility, all were part of building success upon success. The pieces of the puzzle were coming together. Yet, the next round of funding would not close. Something was trapped within a blind spot. In the end, the funding round never happened, and the company was sold. There was no climactic end. Red flags for CEOs to look for in anticipating their own blind spots, which by their very nature are extremely difficult to perceive, see, and root out, include: When you are on a run of success, look for what is hiding in the creases or just beyond your vision; and Locking in on one dimension of logic, staying extraordinarily focused on the prize (this is what they tell you to do, isn’t it?), and rationalizing away anything that doesn’t fit within this logic as noise or a distraction. ___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

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 Financial Products for two consecutive periods in its history. During the first period, he turned FP, is it was known on Wall Street, into a financial engine that turned out derivatives on a super-thin slice of financial exposure in the housing finance market. The risk on the instruments was ‘virtually nil’, in the minds of FP executives. Yet, these instruments print money for this subsidiary of the global financial behemoth, AIG. Times were good. Very good. In the second period of Cassano’s reign, FP crashed. The market changed. The player’s jockeyed for position, searching for positions of strength during troubled waters, and quite frankly, standing by idly as their brethren drown in a sinking market. What happened?  In short, Cassano was caught in his blind spot. He had created a perfect engine. When the situational context in which it operated changed, he was caught unaware of new risks emerging. He was resistant to change. He dug in rather than evolve his decision-making to reflect the unfolding realities. The experience illustrates certain ‘red flags’ that other CEOs can observe both to improve their own decision-making, as well as target that of others, including: Look for CEOs that tamper down dissenting voices in an unreasonable fashion; Look for CEOs that have a very tightly constructed ‘algorithm’ for their decision models, as these models and those who rely upon them will have difficulty adapting their decision models to new conditions and variables. Their mental architecture demonstrates a lack of flexibility and responsiveness;Look for CEOs that are slow-footed, slow to respond to changing situational contexts. For some, shifting conditions represent opportunity, but for the slow-footed, their vulnerabilities will quickly manifest.___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

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, it is a myth. The reality is the seeds of poor decision-making are most often planted years before the climactic high point of the story.   Chris Mailander, author of Judgment: The Art of Momentous Decision-Making (Ironheart Publishing, available on Amazon), describes four CEO archetypes at risk of poor decision-making, and the indicators which tell us why: The FOMO CEO. This CEO sees their peers achieving great success with their businesses.  They see the phenomenal exit which personally enriches the peer CEO and company shareholders; the successful recapitalization or financing of the company; or the launch of a brilliant new product or service receiving accolades from the public.  The FOMO CEO wants to achieve the same. Most often, however, they have not prepared for the journey. They have constructed decision processes customized to the outcome. Their team is not ready to undertake the path. They have not built out a gameplan and the playbook for getting there. They want to play in the biggest game, but haven’t yet risen to the level of competition it demands.  The Frustrated CEO.  This CEO expresses frustration with their team. They feel the team, while they have been good at accomplishing successes to date, does not have the capabilities or domain competencies to achieve the next higher level of success.  Below the waterline, what often is going on is that the legacy decision-making process makes the CEO the final arbiter of all or too many decisions.  The team reporting to the CEO have conditioned their contributions to the decision process to cater to the CEO’s own predispositions and tendencies, for better or worse.  To achieve the next higher level of success will require mastering new domains, thinking about problem-solving in new ways, and increasing the capacity of the organization to take on new challenges.  It is the decision process which needs to be redesigned in order to achieve the next higher level of success. The Bored CEO.  The bored CEO was most alive when they were shepherding the company through years of challenge. Now that the company is successful, the CEO doesn’t feel that same sense of vitality. They grow board. When they grow bored, they grow distracted, taking on new pursuits and hobbies in search of something that can reignite the feeling of vitality. This CEO needs new challenges which reengage them in the company at a deeper level. The Successful CEO. This CEO has been brilliantly successful quarter-over-quarter and year-over-year. They have developed a decision architecture for the company which has been perfected to achieve success and longevity. The challenge emerges when there is a shift in the situational context. The variables in their decision-making change, but their processes do not. It exposes vulnerabilities. These highfliers do make the newspapers, as their climactic downfall causes a splash. They were unprepared.  ___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

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 later to become a parliamentarian in the U.S. Senate, introduced Mailander to the subtle but profound power of understanding and influencing the path of decision arcs. These paths wind. They ebb and flow in response to pressures and vacuums, the jockeying of the players along the way, and to immutable forces of inertia and momentum. How they are crafted and managed, in the end, determines the outcome. More about the flow of the decision arc can be read in Mailander's article appearing in Big Think on July 13, 2023, entitled “How Curling — that Weird Winter Olympics Sport — Can Help You Make Better Decisions” (https://bigthink.com/smart-skills/curling-help-you-make-better-decisions/). To make this a-ha practical for the CEO, identify the most critical imperative for your company over the over the next 12 to 24 months – e.g., buying a company through M&A; finding an exit for liquidity or sale; recapitalizing the business; reorganizing it; achieving greater market share; or sparking organic growth – and then work backwards from that end-point to chart the likely path of the decision arc that will achieve your momentous outcome. Chris Mailander, author of Judgment: The Art of Momentous Decision-Making (Ironheart Publishing, available on Amazon), then describes an exercise CEOs can undertake to help reveal what elements must be true and when they must occur in order for you to achieve the critical objective. By doing so, a curated decision-making process can be crafted that heightens the probability of achieving the end-state objective. ___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

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 pieced together from reviewing thousands of pages of now declassified documents and images from the U.S. Government, including the Department of Defense, Central Intelligence Agency, and U.S. Congress. It reveals how one decision-maker – the commander of the U.S.S. Guardfish – was able to obtain all the secrets of the Soviet Navy at a time when Cold War tensions were at their highest. The Soviet Navy had long had submarines that were larger and more powerful than the Americans. In 1985, the Soviets brought to sea a new class of submarines, the Akula. They were much more stealthy.  It was a dramatic advancement. It changed the fundamental nature of submarine warfare.  The Americans, which had long been able to track the Soviet submarines from long distances, now had to get in close. The commander of the U.S.S. Guardfish did just that, getting within 20m of two new Akula submarines, photographing the entirety of their new ships and engineering advancements. The lessons for CEOs managing their own undersized, less powerful companies against larger incumbents are many, including: Look for advantage in environments in which there is a strategic shift by a competitor; Intelligence-gathering is key; Look for environments in which decision-makers are forced to operate under significant stress; Target actions when players are at risk of making mistakes in their decision-making;Recognize that these moments of opportunity for the weaker player are fleeting;Prepare for these moments by preparing your team, advancing quickly up new learning curves, and preparing gameplans, playbooks, and operational processes for critical moments; and Use decision-making as your weapon.  Chris Mailander, author of Judgment: The Art of Momentous Decision-Making (Ironheart Publishing, available on Amazon) provides several exercises CEOs can use to evaluate their own decision-making within their own situational context, all designed to provoke an a-ha moment.  ___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum

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 story of how.  This is the short story of the long arc of events that led to the 2008 global financial crisis. It begins with warning signs to all about the dangers emerging in the subprime housing market. In 2005, many tried to get their last deals in, make their money, and then run. Others, like Goldman Sachs, began to offload their positions, pushing the risks onto others. In 2007, Goldman Sachs placed the first ever collateral call received by AIG Financial Products on the derivatives it had written for a very select slice of the subprime housing instruments. It was a shock. AIG FP executives were stuck, certain of their positions, fighting against the critics. The reality was that path to the end was already caste.  Fourteen months later, a taxpayer financed bailout became necessary to prevent AIG’s slide into the abyss, taking the entire financial system and the global economy with it.  Something happened in 2005 that manifest to the world at large in 2008, and perhaps not until 2010, when investigators released their comprehensive findings as to the causes and contributors to what became the greatest economic calamity since the Great Depression.  Within these events, a number of lessons emerge for CEOs navigating critical moments of decision-making, including: Studying the long arcs of systemic change; Finding marks which can be placed amongst the competition for which players will rise and which will fall as the decision arc navigates its winding course towards an end, which in this case was a taxpayer financed bailout; Understanding how the intangible of fear within the mind of the markets or public accelerates pacing of the decision arc, increases pressures on decision-makers, and allows irrational behaviors to become normalized; and If you are the slow player, unable to change how you perceive and react to the unfolding shifting conditions, you risk becoming the mark.  Chris Mailander, author of Judgment: The Art of Momentous Decision-Making (Ironheart Publishing, available on Amazon), provides several exercises CEOs can use to evaluate their own decision-making within their own situational context, all designed to provoke an a-ha moment. ___________________________________Socials:X: https://x.com/MailanderPodInstagram: https://www.instagram.com/chris_mailander_podcast/https://www.podcast.chrismailander.com/___________________________________Original Music by Billy Goodrum