In this episode of Business Brain, we dig into the tools that make us better operators, starting with Markdown, the plain-text format John Gruber built to be human-readable and computer-friendly, and now the format our AI overlords love because it burns fewer tokens and runs faster. We share a free live-preview tool at markdownlivepreview.com and Dave’s go-to Mac app, then Read more
In this episode of Business Brain, we welcome a special third brain to the table for World Brain Day as Lisa joins Shannon and Dave with real questions about turning household clutter into a reselling business. We walk through the exact path we’d take: start by selling what you already own, research your market before spending a dime using eBay’s Read more
In this episode of Business Brain, we get into when to stop using chat and move to Cowork. Chat is a great place to start — it’s just not where we should live. Dave’s signals: more than five back-and-forths, or constantly pasting in screenshots, log files, and PDFs. That’s the tell. Point Cowork at the folder instead and stop copying Read more
In this episode of Business Brain, we dig into the exponential timeline — the long, flat stretch every business grinds through before anything looks like growth. We break it down as chutes and ladders: you climb, you slide back, you climb higher. The problem is most of us quit before the hockey stick ever arrives, because the middle part sucks Read more
In this episode of Business Brain, Shannon Jean and Dave Hamilton kick off Casual FridAI with a $10,000 surprise. Dave got an unsolicited email about a domain he’d owned for 21 years and never used — exactly the kind of message he’d normally ignore. This time he fed it to Claude, treated AI as a confidential collaborator, and worked through Read more
In this episode of Business Brain, you’ll rethink everything you assumed about failure. Shannon and Dave dig into why America’s culture of embracing failure, from bankruptcy protection to at-will employment, fuels entrepreneurship in a way most other countries can’t match. You’ll hear how low switching costs mean low experimentation costs, why VCs invest in founders instead of ideas, and why Read more
In this episode of Business Brain, we break down Anthropic’s surprise release of Claude Sonnet 5, a leaner, more agentic model built for the daily grind of coding, automation, and multi-step tool use, and why we’re shifting our default from Opus to save tokens without sacrificing quality. We also dig into the new OpenClaw iOS app, which finally gives us Read more
In this episode of Business Brain, we dig into the power of intentional language and why unnecessary change can quietly wreck a good team. We kick things off with a customer service moment that stuck with us: a tuxedo rental shop promised to call “if we have any questions,” not “if we have any problems,” and that one word swap Read more
In this episode of Business Brain, we tackle a question that hits closer to home than anyone wants to admit: is AI quietly stealing your creative time the same way social media does? We dig into “faux-ductivity” — the trap of endlessly building, prompting, and tinkering in AI under the guise of getting work done, when really it’s just one Read more
In this episode of Business Brain, Shannon Jean and Dave Hamilton tackle a topic that hits every wallet: tipping culture, and how far the pendulum has swung. We dig into why the standing-up-means-no-tip rule makes sense, how COVID-era generosity quietly became the new default, and why getting prompted to tip at the pharmacy or grocery checkout feels so absurd. We Read more
In this episode of Business Brain, we dig into the question of who really controls AI. We trade notes on Anthropic’s new Mythos model and its Fable guardrails — including a jaw-dropping account of how relentlessly capable these tools have become — and we wrestle with the bigger issue lurking underneath: when AI decides what we can and can’t do, Read more
In this episode of Business Brain, we dig into how a little personality goes a long way in business. We talk about turning our interests into businesses (and yes, making a chunk of our lives tax-deductible while we’re at it), then unpack the underrated power of the email autoresponder — how a quick, human note while we’re away humanizes our Read more