Show Notes
Alex Brooker hands his own microphone to the two people who know him best and lets them ask the questions he never answers on his own show. Adrian McKenzie and Oli Deakin, Alex Brooker's former colleagues at Snowflake Software, take over hosting duties on the Travel Tech Podcast to interview Alex directly. The conversation moves through leadership philosophy, the book Alex is writing about his career before and during Snowflake Software, and the early-life habits, from door-to-door fossil sales to a career defining dressing down, that shaped how each of them works today. What You'll Learn Leadership: Being kind, not nice, means having the uncomfortable conversation instead of avoiding it. Feedback: The best feedback often doesn't register as feedback until you reflect on the conversation afterward. Trust: Giving honest feedback gets harder, not easier, with people you haven't worked with for long. Writing: Alex's book centers on the moment a founder's problems outgrow what one person can code alone. Strategy: Most technology leaders solve what's directly in front of them instead of planning three to five years ahead. Formation: Early hustle, from door-to-door sales to Christmas Day shifts, builds a lasting baseline for how someone works. Resilience: Harsh, accurate feedback early in a career can become the turning point that accelerates it. Risk: Leaving a large corporation trades procedural safety nets for closeness to every decision. Time-Stamped Highlights (0:00) Introduction: turning the tables on Alex (2:18) Lessons from moving out of corporate life (2:50) Be kind, not nice (8:17) The challenge of giving honest feedback to people you don't know well (11:14) Alex's book project and its emotional core (13:47) Ollie's hypothetical book: technology strategy (15:50) Formative story: Alex's childhood fossil-selling hustle (19:29) Ollie's turning point: the feedback that changed his career (24:01) Adrian's formative story: dinner table debates and connecting people (25:41) Threads between early formation and post-corporate strengths (26:11) Being closer to the edge: solopreneurship vs. corporate safety (29:02) Why corporate stability is more illusion than reality (30:04) What's next: AI, small business leverage, and future chapters (31:41) Closing thoughts and thanks
Guest bios Adrian McKenzie helped transform and build Snowflake Software alongside Alex Brooker and Oli Deakin before moving into leadership and team performance work, built around the principle of being kind rather than nice. Oli Deakin was also part of the leadership team as CTO at Snowflake Software (in its second life) and now advises technology leaders on building longer term technology strategy, helping heads of tech and CTOs connect day to day decisions to a three to five year vision. About the Podcast The Travel Tech Podcast features long-form conversations with leaders across travel and technology. The show explores how software, data, operations, and distribution come together in real businesses, with an emphasis on tradeoffs, incentives, and lessons that transfer beyond any single company or role.
Host bio Alex Brooker is the founder of Airside Labs, an AI business that applies aviation grade testing and compliance rigor to enterprise AI systems. Before founding Airside Labs, he built and scaled complex software in aviation and safety-critical domains, and he also invests in early-stage technology ventures.
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