The CTO Podcast · Insights & Strategies for Chief Technology Officers Navigating the C-Suite while Balancing Technical Strategy, Team Management, & Innovation

CTO Leadership: Navigating Startup Realities and Inspiring Teams with Krijn Van der Raadt

·42 min·2 clips

Jane McGonigal ran a 10,000-person simulation that closely matched 2020 conditions.

1. The CTO Podcast episode with Krijn Van der Raadt focuses on startup CTO leadership, scaling engineering teams, and practical tools for technical leaders. 2. Etienne de Bruin hosts Krijn Van der Raadt, a former CTO at GreatCall, AppFolio, and MindTouch who now works as a fractional CTO, coach, and mentor. 3. The episode asks what Krijn finds interesting about CTO work and why his experience matters for startup leaders. 4. Krijn says a founding engineer can grow into a CTO title without being effective once a startup passes “two handfuls” of people. 5. He contrasts strong individual engineering with the different demands of leading a rapidly growing organization. 6. Krijn says his years at GreatCall, now part of Best Buy Health, taught him leadership styles, organizational structures, and the challenge of doubling engineering for several years. 7. He frames startup growth as a shift from what works at 10 people to what works at 20 and 40. 8. Krijn says constrained budgets can create better focus because teams must build things that matter to real human beings. 9. He argues that too much money can produce useful-looking work that nobody actually wants. 10. Krijn connects his mindset to being Dutch, describing frugality and careful attention to “every euro or guilder” spent. 11. He also talks about prepping, saying it is less about bunkers and guns and more about understanding supply-chain fragility and local response during outages. 12. Krijn cites a 2008-era warning that the United States was “24 hours away from zero food being shipped” to grocery stores. 13. He recalls a more than 24-hour power outage in San Diego and says responses ranged from neighborhood walks to hearing gunshots. 14. He recommends Jane McGonigal’s book Imaginable and describes her 2010 simulation of a future with a communicable disease, masks, wildfires, and misinformation. 15. Krijn says 10,000 participants in that simulation later thanked McGonigal because they had already rehearsed the emotional stress of 2020-like conditions. 16. He uses that idea to describe a real workshop aimed at moving a product with hundreds of engineers from daily deployments toward continuous deployment. 17. The interview style is conversational and exploratory, with Etienne steering from leadership philosophy into books, tools, and technical practice. 18. Krijn’s answers are practical and reflective, moving from startup structure to prepper thinking to AI tooling without changing the calm tone. 19. People leading startups, engineering orgs, or CTO transitions would likely get the most value from this episode. 20. Listeners wanting fast entertainment or light banter may skip it.

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