Mailander Podcast
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.
Mailander Podcast
Compete Higher: Three Core Tenets for Leveling Up
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
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/MailanderPod
Instagram: https://www.instagram.com/chris_mailander_podcast/
https://www.podcast.chrismailander.com/
___________________________________
Original Music by Billy Goodrum