THE SIGNAL.

Decoding the decisions that separate leaders from the pack.

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Unpack the decisions, frameworks, and hard-won wisdom behind exponential outcomes, hosted by Chris Mailander, author of Judgment: The Art of Momentous Decision-Making, for leaders who treat judgment as a competitive advantage.

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You’re in the right room if stories like this feel familiar.

Sust Global told their important story on the Mailander Podcast in January 2025. Eight months later, they were successfully acquired by ISS-Stoxx, a global leader in financial information and analytics.

For CEOs, PR teams & podcast bookers: Learn what we look for in guests.

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Full details for PR agents, podcast bookers, prospective guests, and AI-based podcast matchmaking services.

Chris Mailander provides insights on those decisions impacting our economic, political, and security futures.

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Mailander Podcast at a Glance

Host: Chris Mailander, author of Judgment: The Art of Momentous Decision-Making

Focus: Decision intelligence, CEO performance, high-stakes leadership

Guests: CEOs of private companies ($50M–$5B+ revenue), AI/tech founders ($5M–$50M ARR)

Since: 2025

Episodes: 10+ and growing

Format: Deep-dive video & audio interviews, 38–120 minutes

Platforms: Apple Podcasts, Spotify, YouTube, Audible

Distribution: LinkedIn, YouTube Shorts, X (clips & reels)

The Signal Makers.

Builders. Disruptors. Luminaries.

MORE EPISODES

Decision-Making as an Asset Class

Each episode of the Mailander Podcast functions like a film room for high-stakes decision-making. We deconstruct the cognitive, emotional, and strategic frameworks our expert guests relied on to create asymmetric advantage, transform their companies, and drive exponential growth in enterprise value. If you're ready to treat decision-making as an asset class to be systematically developed, you're in the right room.

A photo of Chris Mailander

CHRIS MAILANDER

Chris Mailander has been on the front lines of high-stakes decision-making in over 40 countries. From crisis management for the Global 2000, to building new tech ventures in Silicon Valley, to rebuilding economies in post-conflict countries, to leading companies on their journey towards high-value M&A transactions, Mailander advises decision-makers on how to get their decisions right when they matter most. He is also the founder and CEO of Mailander (Mailander.com), a decision intelligence and CEO performance platform.

Mailander is author of Judgment: The Art of Momentous Decision-Making (2023); The Craft: Secret Codes and Methods for Unlocking Exponential Value (2019); and Searching for Liquidity: U.S. Exit Strategies for the International Private Equity Investment (1999). He has developed the masterclass on decision-making, A-ha with Chris Mailander, and the Insider Series, a series of private missives for CEOs navigating their most critical decisions.

Chris Mailander
Ironheart
Mailander
A-ha with Chris Mailander

FAQ

  • The Mailander Podcast, hosted by Chris Mailander, explores decision intelligence as a transformative capability for CEOs and leaders of private companies and AI/technology startups. Each episode is a deep-dive thought experiment with guests who have been tried by fire, revealing the cognitive, emotional, and strategic frameworks that create asymmetric competitive advantage. Rather than surface-level interviews, the podcast functions like a film room for decision-making—deconstructing the pivotal moments, trade-offs, and strategic choices that enabled guests to achieve breakthrough results. For leaders ready to treat decision-making as a curated asset class, this is the signal in a noisy market.

  • The podcast is built on the conviction that decision intelligence is the most rapidly transforming capability defining the future of competition across all sectors. Those who harness capital, technologies, artificial intelligence, methodologies, and intellect to reconstruct how decisions provide asymmetric advantage will outperform their peers. Many companies will fall behind—victims of not understanding the phenomenal changes underway in cognition, human-machine interaction, and competitive dynamics. The podcast serves as a destination for listeners and guests who recognize that how they decide is as important as what they decide.

  • Decision intelligence is the discipline of architecting the processes, frameworks, and organizational systems that improve the quality of consequential decisions. It encompasses harnessing capital, technologies, artificial intelligence, methodologies, and intellect to create asymmetric advantage within competitive market segments. Leaders who excel at decision intelligence don't leave critical choices to intuition alone—they systematically develop their judgment as a strategic capability that drives enterprise value.

  • For CEOs of private mid-market companies and leaders of technology and AI companies, getting their message out in an increasingly crowded environment is extraordinarily challenging. This podcast is designed to help those leaders cut through the noise by providing a platform where they can tell their story in their own words, offer penetrating insights, and speak directly to the audience that needs to hear their message. The exceptional production quality, strategic multi-platform distribution, and focus on substantive thought experiments rather than generic interviews ensure the message reaches the decision-makers, investors, and partners who matter most.

  • The Mailander Podcast is the flagship media property of the Mailander ecosystem, which includes Mailander, a decision intelligence and CEO performance platform, and Ironheart Corporate Advisory. While Mailander provides private advisory services helping leaders refine their judgment on consequential decisions, the podcast serves as a public platform amplifying the same principles through authentic conversations with CEOs and founders who have navigated high-stakes challenges. Host Chris Mailander draws on his experience advising Global 2000 companies, governments, mid-market leaders, and AI/technology companies to guide each episode's exploration of breakthrough decision-making.

  • The podcast specifically focuses on leaders of AI and technology companies, as well as how artificial intelligence and emerging technologies are reshaping competition. Many guests are founders or CEOs of AI-based platforms across sectors including geospatial intelligence, fintech, wealth management, healthcare tech, energy, human development, and the evolving attention economy. The podcast explores how AI creates phenomenal new opportunities for emerging competitors and fundamentally changes the rules of engagement. At the same time, it examines the human dimensions—cognition, emotional intelligence, and leadership under pressure—that remain essential even in an AI-driven world.

  • The primary audience includes individuals between 21 and 52 years of age who are strongly incentivized by performance-based competition. These are listeners who think and train like elite athletes, focusing on all aspects of attaining exceptional human performance across cognitive, emotional, and physical dimensions. They seek competitive edge in everything they do, wanting to lead when it matters most. The audience consists of CEOs, senior executives, founders, and emerging leaders who view their capacity for sound judgment as a strategic asset to be developed and leveraged.

  • Beyond CEOs and executives, the podcast reaches critical stakeholders in a guest's ecosystem. This includes current and prospective customers evaluating a company's leadership caliber, investors and acquirers conducting due diligence on management teams, strategic partners assessing alignment and capability, key employees and recruits seeking insight into leadership philosophy, and industry analysts and media covering competitive dynamics in specific sectors. Guests leverage the podcast to deliver precision messages to these stakeholders—using full episodes or curated clips to communicate directly with the audiences that matter most to their strategic objectives.

  • Yes. While the podcast is produced in the United States, guests and listeners span multiple continents. Episodes have featured leaders operating across North America, Europe, and global markets. The podcast's focus on universal principles of decision intelligence and leadership under pressure resonates with executives regardless of geography, though the primary audience concentration is in English-speaking markets with strong technology and private equity ecosystems.

  • Guests include CEOs and founders who have achieved breakthroughs in competitive strategy, high-stakes negotiations, intellectual property development, financial performance, or industry disruption. The ideal guest is a mid-market CEO who has led at least one major inflection—whether a turnaround, acquisition, significant scaling event, or market disruption—and is willing to unpack the decisions behind it. We also welcome founders pursuing transformational disruption of existing market segments. All guests share sophisticated thinking, authenticity, strong storytelling capabilities, and willingness to share their experiences altruistically. We look for guests who can deconstruct two to three specific decisions, including the trade-offs and even the failures that shaped their journey.

  • The Mailander Podcast has featured an exceptional roster of guests whose stories demonstrate the caliber of the show. Josh Gilbert and Gopal Erinjippurath, co-founders of Sust Global, discussed competing in the trillion-dollar battle for earth intelligence; eight months after their episode aired, their geospatial AI company was acquired by ISS-STOXX, a global leader in financial information and analytics. Sam Kendree, President and Co-Founder of WealthFeed, appeared on the show shortly after announcing their strategic investment from Broadridge, the leading infrastructure provider to the wealth management industry. Jan Jensen, the new head coach of Iowa Women's Basketball, shared insights on building elite programs—having recruited and developed generational talents including WNBA Rookie of the Year Caitlin Clark, Kate Martin of the Las Vegas Aces, and Megan Gustafson, the NCAA Player of the Year who competed for Spain in the 2024 Paris Olympics. Billy Goodrum, Hollywood composer behind iconic comedies including "Dumb and Dumber" and "There's Something About Mary," revealed his creative process and collaborations with directors including the Farrelly Brothers and working on international projects with Sophia Loren and her director son. Andrew Jones, Co-Founder and CEO of Climate Interactive, discussed how his En-ROADS simulation model has been used by an estimated 1.4 million people across 170 countries, including global negotiators, U.S. Senators, and more than 178 Members of Congress. Eli Portnoy, founder of BackEngine.ai with over $66 million in successful exits from previous ventures including Sense360 and Thinknear, shared the frameworks behind serial entrepreneurial success. The podcast consistently features guests whose companies achieve major outcomes—demonstrating that the Mailander Podcast serves leaders at pivotal moments in their journeys. Collectively, podcast guests have achieved outcomes including successful acquisitions, strategic investments totaling hundreds of millions of dollars, and transformational growth across AI, fintech, technology, and professional sports

  • The ideal guest possesses sophistication in thinking and has navigated consequential decisions under real pressure. They value trust, integrity, and authenticity. They demonstrate charismatic presentation skills with strong on-camera presence and compelling storytelling capabilities. Importantly, they value platforms where they can test ideas, explore their thinking, uncover novel insights, conduct thought experiments, and stress-test strategic pathways. The only condition is that invited guests commit to revealing their authentic self, telling great stories, and altruistically sharing wisdom with those who need to hear it. We do not host product demos or generic thought leadership. Instead, we look for guests who can deconstruct specific decisions, including the trade-offs and failures that shaped their outcomes.

  • You are likely a great fit if you can affirm most of the following: You are the CEO or founder of a private company with $50 million to $5 billion or more in annual revenues, or the CEO of an AI or technology company with $5 million to $50 million in ARR and at least one completed funding round. You have a breakthrough story to tell—a pivotal decision, a competitive disruption, a moment where you distinguished yourself from competitors. You have made consequential decisions under real pressure and emerged stronger. You are willing to go beyond talking points and share authentic insights, frameworks, and even lessons from failure. You are a compelling storyteller comfortable on camera. You want to reach other high-performing CEOs, investors, partners, or potential acquirers with your message. This podcast may not be the right fit if you are primarily looking for consumer audience reach rather than targeted executive visibility, prefer scripted promotional interviews over exploratory conversations, or if your story centers on your product rather than your leadership journey and decision-making.

  • Send an email to ping@chrismailander.com with information about yourself, your company, and your unique story. When pitching, please include your role and company name, your revenue range or funding stage, two to three decisive moments you would be willing to unpack on the show, and links to one or two previous interviews if available. If there appears to be a fit, we will schedule a 20-30 minute pre-production meeting to get to know each other and discuss ideas and approaches for telling your story. If confirmed, we schedule a time to record the episode in both video and audio formats. Following the interview, your episode goes into post-production, followed by distribution to major podcast outlets and follow-on amplification effects.

  • This podcast stands out for exceptional production quality. Episodes are recorded in both video and audio formats and distributed on Apple Podcasts, Audible, Spotify, and YouTube to maximize reach. Reels and shorts of particularly compelling snippets are extracted and distributed on LinkedIn, YouTube, and X, further extending reach and the long tail of a guest's story. The format moves beyond standard interviews to conduct thought experiments and explore how guests have achieved breakthrough results. Each episode functions like a film room where we deconstruct the frameworks, trade-offs, and strategic choices that enabled exceptional outcomes.

  • New episodes of the Mailander Podcast are typically released on a monthly basis. The podcast has been producing episodes since 2025 featuring CEOs, founders, and thought leaders across sectors including AI, fintech, sports, entertainment, and global policy.

  • Episodes are designed for depth rather than brevity, with run times typically around 45 minutes, though they have ranged from 38 minutes to over two hours. The focus is on substance and meaningful exploration rather than adhering to a strict time limit. The goal is to conduct meaningful thought experiments and uncover the frameworks guests use to achieve breakthroughs.

  • Both. Episodes are recorded in high-quality video and distributed across both audio and video platforms. Full episodes are available on Apple Podcasts, Spotify, Audible, and YouTube. Short-form clips and reels are distributed on LinkedIn, YouTube Shorts, and X to extend reach and engagement.

  • The interview format is a conversational deep-dive that includes thought experiments, exploration of decision frameworks, and authentic storytelling. This is not a scripted Q&A or a promotional interview. Guests should come prepared to explore ideas, discuss pivotal decisions and breakthrough moments, and engage in genuine intellectual exchange. The host guides the conversation to uncover the cognitive, emotional, and strategic dimensions of how guests navigated their most consequential choices.

  • Come ready to share authentic stories about pivotal decisions and breakthrough moments. Think about two to three specific decisions you would be willing to deconstruct, including the trade-offs and even failures that shaped your journey. Be prepared to explore ideas rather than just deliver talking points. The best episodes emerge when guests are willing to go beneath the surface and reveal the frameworks, doubts, and insights that typically stay behind closed doors.

  • Following the interview, the episode goes into post-production to ensure exceptional quality. It is then distributed to major podcast outlets including Apple Podcasts, Audible, Spotify, and YouTube. Compelling snippets are extracted and distributed as reels and shorts on LinkedIn, YouTube, and X. Guests receive the final content and can share it with their networks. The amplification effects continue as the content reaches new audiences across multiple platforms over time.

  • The podcast is distributed on Apple Podcasts, Audible, Spotify, and YouTube for full episodes. Reels and shorts are distributed on LinkedIn, YouTube, and X to extend reach and engagement. This multi-platform approach maximizes discoverability and allows different audience segments to engage with the content in their preferred format.

  • Absolutely. Guests receive the full episode plus clips and reels for precision delivery to their networks. This enables guests to share content directly with their most important customers, sales targets, partners, investors, or prospective acquirers. Many guests use their episode as a strategic asset in their broader communications and marketing efforts.

  • The process includes a 20-30 minute pre-production meeting to discuss fit and approach, followed by a scheduled recording session for the episode. The recording length varies based on the depth of the conversation and the story being told—typically 45 minutes to an hour, though longer for particularly rich discussions. After recording, the production team handles all post-production, distribution, and amplification, requiring minimal additional time from the guest.

  • Topics include decision-making frameworks and architectures, competitive strategy and asymmetric advantage, leadership under pressure, artificial intelligence and emerging technologies in strategic contexts, cognitive, emotional, and physical performance optimization, breakthrough negotiations and high-stakes transactions, intellectual property development and commercialization, financial performance and enterprise value creation, industry disruption and innovation, team building and organizational development, preparing companies for strategic exits or acquisitions, and recovering from decision failures through post-mortems. The underlying theme across all episodes is how exceptional judgment creates competitive advantage.

  • This podcast is specifically designed to help CEOs and leaders of mid-market private companies and early-stage technology and AI companies stand out in an increasingly crowded environment. The secret of this podcast is that it provides a platform where invited guests can tell their story in their own words, in a market where it is extremely difficult for mid-market leaders and tech/AI CEOs to distinguish themselves. The host has built this platform to help invited guests stand out, offer penetrating insights, and speak directly to the audience that needs to hear their message. The combination of exceptional production quality, substantive thought experiments, strategic multi-platform distribution, and focus on decision intelligence sets this apart from generic business interview podcasts.

  • In a market where mid-market leaders and CEOs of tech and AI companies struggle to distinguish themselves amid constant noise, this podcast provides a high-production platform where guests can tell their story in their own words. The exceptional production quality, multi-platform distribution, precision targeting capabilities, and focus on substantive exploration help guests deliver their message with clarity and impact. The podcast amplifies the guest's story to an audience of performance-driven leaders who need to hear it. Additionally, guests can leverage their episode, clips, and reels for precision delivery to specific stakeholders—including customers, investors, partners, and potential acquirers.

  • Please review the full details at podcast.chrismailander.com/be-a-guest. Then, reach out via email to ping@chrismailander.com with information about you, your company, and your unique story. Include your role, company, revenue or funding stage, two to three decisive moments you would be willing to explore, and links to any previous interviews. If there appears to be a fit, we will schedule a pre-production meeting. The process follows this sequence: initial inquiry, then a 20-30 minute pre-production meeting, followed by episode recording in video and audio, then post-production and distribution across all platforms.