Self-Driving Marketing: Beyond Basic Automation
Featuring special guest Justin Rae, founder and CEO of Cinch, Jim and Veer discuss how customer data can drive more useful marketing. Justin explains how…
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Using AI to Speed Up Development Without Losing Control
Featuring special guest Evan Moser, CTO of iClassPro, Jim and Veer discuss how his team is using AI to update a mature software platform. Evan explains…
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The Future of Accounting and Finance: AI, Talent, and Executive Leadership
Featuring special guest Ken Philbrick, Jim and Veer discuss how AI is changing finance work and the people companies hire to lead it. Ken, a Partner at…
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Data Readiness, Learn by Building, and the Build-or-Buy Decision
Meeting notes, project files and conversations can help an AI understand a business, but someone has to decide how that information fits together. Jim and…
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"Raccoons in a Trench Coat" – The Realities of Building Your Own Open Brain
Jim and Veer compare what their personal AI knowledge systems are actually doing for them. Jim describes a daily reminder that suggests client follow-ups…
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Stop Dreaming, Start Doing: AI Where It Actually Matters
A 13-week cash flow forecast gives Jim and Veer a concrete place to start talking about AI at work. Jim describes using AI to handle the preparation so he…
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Self-Driving Marketing: AI Agents and the Future of PC Performance
Featuring special guest Justin Rae, Jim and Veer continue a two-part conversation about the systems behind Cinch's marketing software. Justin describes…
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The AI Shift Nobody Saw Coming - From Chatbots to Self-Driving Marketing
Featuring special guest Justin Rae, Jim and Veer begin a two-part conversation about how Cinch uses customer data to help local businesses make better…
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AI reps, local agents, and why business cases still matter
Veer shares an experiment with a local AI assistant that can see what's on his screen and offer help while he works. Running a smaller model on his Mac…
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Genies, Interns, and the Myth of Lazy AI: Anthropic’s 4D Framework & The Future of Entry-Level Work
Giving AI a task takes more thought than handing it a sentence and accepting what comes back. Jim uses Anthropic's 4D framework to discuss delegation,…
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When AI Makes You Angry: The Distrust Trend Among Young Professionals
Jim and Veer discuss why some younger people are skeptical of AI even as employers encourage them to use it. They consider concerns about jobs, creativity…
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The Critical Difference Between Using AI Frequently and Using It Well
An AI reporting tool that cost about 30 cents to run was set aside because of concern about the expense. Jim and Veer use that example to ask how…
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Rethinking AI Utilization: Beyond Vanity Metrics to Real Business Value
Tracking usage can show that employees are trying AI, but it leaves a lot unanswered about the work. Jim and Veer discuss how to evaluate adoption as…
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The Reality of AI Adoption: Risks, Mindsets, and Strategic Focus
A business process can become dependent on an AI model that the company doesn't control. Jim and Veer discuss what happens when access, vendor decisions…
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Navigating the Realities and Risks of AI in Business Strategy
Jim and Veer explain tokens and context using examples from the AI literacy work they do with clients. They discuss why a model's costs can be hard to…
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Human Problems vs. Tech Solutions: Enhancing Collaboration in the Age of AI
A retailer is spending time entering product descriptions into a tool that has no bulk import feature. Jim and Veer work through the example, including…
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Moving From AI Novelty to Operating System: Maturity Curves for Mid Sized Businesses
Jim and Veer discuss how a mid-sized business can judge its progress with AI. They compare occasional experiments, such as rewriting an email, with…
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Unlocking the Power of AI in Executive Productivity
Veer walks through the morning briefing he built with Cyrano and Balcony. It brings together his calendar, recent conversations and unfinished work so he…
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Building a Personal "Open Brain": Implementation and Future Potential
Jim and Veer walk through the components of the personal knowledge systems they're building. They explain how stored information becomes searchable, the…
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Building an AI-Driven "Second Brain": Part 1
Starting a new AI conversation often means explaining the same background again. Jim and Veer introduce the personal “open brain” projects they're…
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Turning Curiosity into Value: A Functional Executive's Guide to AI Fluency and Adoption
Jim and Veer compare the curiosity that gets someone started with AI and the persistence it takes to become useful with it. They draw on their own…
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From Hype to Practicality: Functional Executives on Real-World AI Applications
Jim and Veer compare what they are learning while building tools for real work. Jim describes a reporting product with a very specific output: an email…
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Building Smarter, Not Harder: How AI Agents Accelerate Business and Decision-Making
Jim describes building a voice-based reporting prototype for his wife's business with Cursor. Having an actual user and a clear reporting need helped him…
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Accelerating Careers with AI: Lessons in Leverage, Humility, and Practical Application
Veer walks through a personal job board he built to help a longtime friend. It uses the friend's experience and location to research suitable employers,…
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Executive Function in the Age of AI: Margin, Meaning, and Machines
Jim Boswell and Veer Hossain introduce Functional Executives and the work they want to explore together: practical uses of AI for people responsible for…
Listen & readStart with what’s
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Find episodes about the work you’re doing, from getting your data ready to deciding what to build.
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We compare notes on the tools we use, the projects that need more work, and the decisions we’re still figuring out.
Jim looks at the finance and operating decisions. Veer builds and experiments with the technology. Our guests join us to talk about what they’ve learned in their own work.
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