AI, leadership, and the realities of running a business. Pick a topic, find a familiar challenge, or start at the beginning.
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 Cinch uses buying patterns, price sensitivity, and…
Listen & readFeaturing 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 how a series of agents examines legacy code, scopes…
Listen & readFeaturing 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 Adam James International, brings examples from…
Listen & readMeeting notes, project files and conversations can help an AI understand a business, but someone has to decide how that information fits together. Jim and Veer work through that problem using their own…
Listen & readJim and Veer compare what their personal AI knowledge systems are actually doing for them. Jim describes a daily reminder that suggests client follow-ups and prepares Outlook drafts for him to review.…
Listen & readA 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 can spend more time checking the numbers,…
Listen & readFeaturing special guest Justin Rae, Jim and Veer continue a two-part conversation about the systems behind Cinch's marketing software. Justin describes his vision for more autonomous marketing and the…
Listen & readFeaturing special guest Justin Rae, Jim and Veer begin a two-part conversation about how Cinch uses customer data to help local businesses make better marketing decisions. Justin, Cinch's founder and CEO,…
Listen & readVeer 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 makes the idea tangible, but the speed and quality…
Listen & readGiving 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, clear instructions, reviewing the output and taking…
Listen & readJim 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 and the opportunity to learn through doing the…
Listen & readAn 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 companies judge the cost of a new workflow, including the…
Listen & readTracking 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 people move from occasional use to tools they…
Listen & readA 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 or regulation changes, and how that uncertainty…
Listen & readJim 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 understand at first, and why restricting usage…
Listen & readA retailer is spending time entering product descriptions into a tool that has no bulk import feature. Jim and Veer work through the example, including the missing connection to supplier information and…
Listen & readJim and Veer discuss how a mid-sized business can judge its progress with AI. They compare occasional experiments, such as rewriting an email, with processes where people use the tools regularly and…
Listen & readVeer walks through the morning briefing he built with Cyrano and Balcony. It brings together his calendar, recent conversations and unfinished work so he can prepare for the day with the relevant context…
Listen & readJim and Veer walk through the components of the personal knowledge systems they're building. They explain how stored information becomes searchable, the roles of Supabase and pgvector, and how embedding…
Listen & readStarting a new AI conversation often means explaining the same background again. Jim and Veer introduce the personal “open brain” projects they're building to make earlier conversations and work available…
Listen & readJim 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 experiments and client work, including the difficulty of…
Listen & readJim 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 that needs to be consistent and useful to a business…
Listen & readJim 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 decide what to build and how to direct the AI…
Listen & readVeer 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, explain why a job fits and prepare a tailored…
Listen & readJim Boswell and Veer Hossain introduce Functional Executives and the work they want to explore together: practical uses of AI for people responsible for running a business. They bring their finance and…
Listen & readJim Boswell and Veer Hossain introduce Functional Executives with a short example of what they have been building. Jim, a CFO without formal software development training, describes an application he…
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