In this episode of the Shift AI Podcast, LaSean Smith, Product and Growth Lead at Google Cloud, joins host Boaz Ashkenazy for a wide-ranging conversation on how systems thinking and agentic AI are reshaping the way individuals, small businesses, and enterprises operate.

LaSean shares a career journey that spans Microsoft HoloLens, Amazon, a successful startup exit, and now Google — plus a portfolio of small businesses that have served as his real-world AI lab. From a salad shop in Renton to a pre-construction development business in Seattle, he's applied workflow design and agent automation to solve practical problems long before it was fashionable.

The conversation digs deep into how to actually build effective AI agents — not by prompting a chatbot, but by thinking in workflows first, identifying where reasoning actually needs to happen, and writing skills that make agents fast, reliable, and token-efficient. LaSean explains the "parcel grader" agent he built for his construction business, why he starts every agent build in a chat interface before moving to CLI, and how the McDonald's SOP model is the right mental framework for getting great output from AI.

Boaz and LaSean also discuss the barbell economy that AI is creating — where small players and large enterprises both gain leverage while the middle gets squeezed — why Microsoft's Copilot strategy missed the point, how to think about agent security and identity, and why healthy organizational culture is the actual prerequisite for successful AI adoption.

The episode closes with a reflection on what "always changing" really means as a mindset, and why building resilience and systems thinking skills now is the most important career investment anyone can make.

This episode is essential listening for entrepreneurs, operators, and anyone using or thinking about deploying AI agents in their work.

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Chapters

[00:00] Episode 100 and LaSean's First Jobs

[03:30] From Microsoft HoloLens to Amazon to Google: LaSean's Career Path

[08:00] What LaSean Does at Google Cloud Today

[11:00] The Entrepreneurial Side: Small Businesses as an AI Lab

[16:00] The Barbell Economy: Why the Middle Is Being Squeezed

[20:00] Building the Parcel Grader Agent for Pre-Construction

[25:00] How to Write Better Skills: Start in Chat, Not CLI

[30:00] Workflow Thinking vs. Department Thinking

[35:00] Why Google Is Generating 75% of Its Code with AI

[38:00] The McDonald's SOP Model for Agent Design

[42:00] Agent Security for Individuals and Small Businesses

[47:00] Enterprise AI: Governance, Trust, and Organizational Design

[52:00] The Two-Word Future of Work: Always Changing

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Connect with LaSean Smith

LinkedIn: https://www.linkedin.com/in/laseansmith/

Connect with Boaz Ashkenazy

LinkedIn: https://www.linkedin.com/in/boazashkenazy/

Email: [email protected]