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
My Blind Spot: Hard Lessons Learned Painfully Well
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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.
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Original Music by Billy Goodrum