What happens when a technology starts to look, sound, and reason like us?
Taylor Black, Director of the AI Ventures Ecosystem in the CTO’s Office at Microsoft, has spent his career at the intersection of data, venture building, and emerging technology. From bootstrapping a SaaS company to helping shape early stage AI innovation inside one of the world’s largest technology organizations, Taylor brings a rare long term perspective on what AI is, and what it is not.
In this conversation, we explore how today’s AI moment compares to past technological revolutions, why most current AI applications are still low hanging fruit, and where the real economic and organizational disruption is likely to come from next.
We discuss the limits of automation, the rise of agentic systems, the moral responsibility of those building AI, and why the hardest work ahead is not technical, but cultural.
This is a wide ranging discussion on AI, human work, governance, and the difference between making hard things easier versus making impossible things merely difficult.
Connect with us:
Website: https://thedatastorytellers.com/
LinkedIn: https://www.linkedin.com/company/the-data-storytellers
Apple Podcasts: https://podcasts.apple.com/gb/podcast/the-data-storytellers-podcast/id1493766476
Spotify: https://open.spotify.com/show/2N0vZtHZHgod4Tll2LX2xa
YouTube: https://www.youtube.com/channel/UCz9e56lhYUfORiOHMiLlPmA
Chapters
00:00 – Introducing Taylor Black and his role at Microsoft
04:00 – From bootstrapped SaaS founder to data driven decision making
10:30 – Learning to translate technical insight into business value
16:30 – Venture studios, zero to one work, and entering Microsoft
23:30 – How ChatGPT changed perception inside large organizations
28:00 – The steam engine analogy and why infrastructure matters
33:30 – AI, work, and why modern jobs already felt broken
40:00 – Presence, remote work, and the limits of digital collaboration
46:00 – AI optimism, AI fear, and misunderstanding the technology
52:00 – What large language models actually are and are not
58:30 – Governance, moral responsibility, and who shapes AI
1:05:30 – Agentic systems, job disruption, and what comes next