Episodes
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111: Every technology decision you make now is a post-quantum decision
SEPTEMBER 22, 2026
Quantum computing may not be breaking your security today, but the decisions you make now could determine how exposed your organization is when it does. Conor Deegan explains why CTOs need to start preparing before Q Day arrives.
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110: AI Compressed the Work That Built Your Judgment
SEPTEMBER 14, 2026
Twenty years at one company should have made my guest predictable, and that is exactly the trap he built a method to escape.Build your own CTO Playbook at
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109: Your Agents Are Held to a Lower Standard Than Your Engineers
SEPTEMBER 08, 2026
Most CTOs think adopting AI means picking the right tools, but Sumeet argues the real work is closing the accountability gap between agents and engineers.Build your own CTO Pl...
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108: Your Most Valuable Executive Relationship Is the CFO
SEPTEMBER 01, 2026
Ask a CTO which executive relationship matters most, and they'll name the CEO, but my guest today would send you to the CFO instead.Build your own CTO Playbook at
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107: The Controlled Re-Entry: A CTO Playbook for Coming Back from Holiday
AUGUST 25, 2026
I nearly turned my own summer into the cautionary tale. The thing that saved me was a last-minute week in the Swedish mountains.Build your own CTO Playbook at
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106: Trust, temper, override: managing the AI you don't control
JULY 28, 2026
One CTO spent two weeks tearing frontier models out and ended up back where they started. Another spent a few days building a tested escape route for what actually mattered.Bu...
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105: The CTO's real job when agents write the code (belief reversal)
JULY 21, 2026
A founder went from zero to $10 million ARR in six months with six engineers and fifty agents, and the gap between idea and shipped feature was nine hours.Build your own CTO P...
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104: Why the Best CTOs Filter the Firehose Instead of Blocking It
JULY 14, 2026
Shielding your team from context isn't protection, it's a subtle underestimation of the people you hired for their judgment.Build your own CTO Playbook at
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103: What CTOs Miss Before an M&A Deal Hits
JULY 07, 2026
Most CTOs chase value creation. Jaco Vermeulen says the real job is preserving it first. Build your own CTO Playbook at
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102: AI Transformation Starts With What You Don't Know You're Assuming — with Duri Chitayat
JUNE 30, 2026
Duri's father holds more than 100 patents, filed his latest one at 96, and gave him a one-line philosophy that now drives how his teams approach every problem: most people don't try.
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