Episodes
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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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101: Why Most Leadership Assessments Are Measuring the Wrong Thing
JUNE 23, 2026
What if the biggest constraint on your organisation isn't your tech, your funding, or your market, but whether your leaders can think at the level the problem requires?Build y...
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100: Why AI Is Quietly Draining Your Senior Engineer Pipeline
JUNE 16, 2026
The reps that used to turn juniors into seniors are disappearing, and most engineering leaders won't notice until the senior shortage hits in three years.Build your own CTO Pl...
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99: Why Transformations Die Just Before They Succeed
JUNE 09, 2026
The most dangerous moment in a transformation isn't the start, it's the stretch right before behaviours actually start sticking.Build your own CTO Playbook at
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98: The Office of the CTO at RevenueCat, with Miguel Carranza
JUNE 02, 2026
When do you stop being the CTO with all the answers and start being the one who asks better questions?Build your own CTO Playbook at
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97: Stop Hiring More of the Same — Michelle McDaid, The Leading Place
MAY 26, 2026
Women weren't pushed out of tech once. There were multiple waves, and the patterns are still showing up in how teams get built today.Build your own CTO Playbook at
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