🎙️ Episode 12: Guest Series - John Mathias' GenAI Journey — From feeling behind to expert

In this episode of Practical Prompting, Alex is joined by longtime collaborator John Mathias—law degree from Regent University, a stint at a think tank in DC, and now years of startup building.

Act I: Dives into John’s personal journey with GenAI: his first experiments, everyday wins, and the “aha” moments that made AI feel less like a toy and more like a tool.

Act II: Zooms out to the professional side: how those same skills translated into legal research, policy analysis, and startup workflows, plus the challenges and opportunities he’s uncovered along the way.

🎯 Your Challenge: Email alex@lololai.com with how many questions you ask GenAI each day.

Connect with John: email-jmathias@lololai.com, website-lololai.com, linkedin-johnmathias.

Disclaimer: Views expressed are Alex’s own and do not represent any employer; no confidential information is shared.

Connect: alex@lololai.com

🎙️ Episode 11: Why GenAI Feels Scary — Driving clarity through the foggy fear

GenAI feels like quicksand: kids are already using it for schoolwork, headlines scream that most enterprise pilots flop, and “strategy” sounds like a buzzword. In this episode, we name the fear—and shrink it. You’ll get a simple, repeatable way to turn ambiguity into choices you can prove in 30 days.

Act I: We start at the kitchen table (why getting started is daunting, what kids are actually doing with GenAI, and why that matters.

Act II: We'll then jump to the workplace where strategy often stalls due to fear. Along the way, you’ll hear practical, real-world examples leaders face every week—like creating a “Monday Ops Pack,” and a starter GenAI strategy to get you started.

🎯 Your Challenge: Email alex@lololai.com with your Top-3 fears you feel or see with your own GenAI adoption.

Disclaimer: Views expressed are Alex’s own and do not represent any employer; no confidential information is shared.

Connect: alex@lololai.com

🎙️ Executive Series — Episode 10: Objection Anticipated — Turning AI Into Your Toughest Opponent

In this Executive Edition of Practical Prompting, Alex and his AI co-host, Practically Speaking, turn a tactic into a habit: use AI to surface objections before your stakeholders do—so decisions get faster, safer, and sharper.

Act I: The Couch Dilemma → The Hidden Criteria Play Alex walks through replacing a couch in hours, not months, by converting “vibes” into ranked constraints (back height, seat depth, dog-proof leather) and reframing the use case (reading + tea, not home theater). The result: fewer, better options and a cleaner ask. Lesson: many “objections” are your own unspoken criteria. Name them, and the noise falls away.

Act II: AI as Your Objection Simulator We zoom out to leadership. Before your deck leaves your desk, run an AI premortem: simulate CFO/COO/Legal—or whichever roles are actually in the room—merge duplicates, and return only the top three objections with evidence and a two-sentence counter. Package it in a one-slide “Likely Objections” box and a Decision Card (Goal, 90% plan, Top-3 risks + counters, Clear Ask). This reframes prep from defensive to proactive and trims approval latency.

🎯 Your Challenge: Run the meta-prompt on one live proposal today. Email alex@lololai.com with your Top-3 objections and the single riskiest assumption you’ll test this week.

Disclaimer: Views expressed are Alex’s own and do not represent any employer; no confidential information is shared.

Connect: alex@lololai.com