The Agentic Entrepreneur: How the next wave of AI is changing the startup playbook
GeekWire
GeekWire
4.4 • 116 Ratings
🗓️ 4 October 2025
⏱️ 51 minutes
🧾️ Download transcript
Summary
This week on the GeekWire Podcast: How artificial intelligence is changing the way companies are created, built, and operated. We're on location at Pioneer Square Labs in Seattle with investor and entrepreneur T.A. McCann, a managing director at the startup studio and venture capital firm.
He explains how AI agents are automating complex functions, letting small teams do the work that once required large groups of people. As AI makes product development easier, he says, the key strategic moat for many startups is now shifting to distribution and data.
Other topics include:
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The wearable AI recorder that captures everything he says throughout the day.
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The rise of the "one-person billion-dollar company" powered by a suite of specialized AI agents.
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How AI-generated personas are replacing human focus groups for market research.
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The future of "agent-to-agent" conversations, where different AI systems negotiate with each other on behalf of their companies.
With GeekWire co-founder Todd Bishop; Edited by Curt Milton.
See omnystudio.com/listener for privacy information.
Transcript
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| 0:00.0 | How many businesses could Todd Bishop run with a system like that? |
| 0:06.5 | Dozens. |
| 0:07.4 | Dozens? |
| 0:08.1 | Tens? |
| 0:08.8 | Hundreds. |
| 0:09.4 | Yeah. |
| 0:10.1 | And you might be managing 10 businesses that are small. |
| 0:13.7 | You might be managing one or two businesses that are big. |
| 0:16.6 | And you are relaxing on the beach with your family in Hawaii. |
| 0:27.3 | Yeah. and you are relaxing on the beach with your family in Hawaii. Welcome to Geekwire. I'm Geekwire co-founder Todd Bishop. |
| 0:30.8 | T.A. McCann is a Seattle-based serial entrepreneur, investor, and managing director at Pioneer Square |
| 0:36.8 | Labs, or PSL, which is a startup |
| 0:39.2 | studio and venture capital firm. He has a history of building and selling technology companies, |
| 0:44.2 | and he's now focused on the next generation of AI, particularly AI agents. His perspective is shaped |
| 0:51.3 | by his hands-on experience as a founder, his current role as an investor and builder at PSL, and his philosophy of personal productivity, and also really a sense of health and wellness and the integration of technology into that. |
| 1:05.7 | TA, it's great to have you on the show. |
| 1:07.3 | I see again, Todd. |
| 1:08.3 | Absolutely. |
| 1:08.9 | And so I've got all sorts of questions for you about AI agents and where things are headed, where you see productivity and personal assistance going. |
| 1:16.6 | But I have to start with what you're wearing on your shirt. Tell me what you're wearing on your shirt. |
| 1:23.1 | So this is a product called Limitless. It is a little clip on recorder and I wear it all day long |
| 1:29.2 | now and it records effectively everything I say, transcribes that, uploads it to the cloud, |
... |
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