🎙️ 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

🎙️ Executive Series — Managing Up with AI Episode 9: From Two Pages to 100 Words (and Why Timing Beats Brevity)

In this Executive Edition of Practical Prompting, Alex and his AI co-host, Practically Speaking, dig into one of the most overlooked leadership skills: managing up.

Act I: We put a two-page update on the chopping block—distilling it into a high-impact, 100-word brief for a senior leader. You’ll hear why “shorter” isn’t the goal—decision-ready is—and how to use meta-prompts and guardrails (“with high accuracy”) to get AI-generated summaries that hit 97% of the mark in seconds.

Act II: We zoom out to the strategy: managing up as timing, not just content. From building a “priority heat map” to experimenting with digital twins of senior leaders, Alex and PS explore how to align updates with what’s actually on the radar. We close with three AI-powered tactics you can use today to make your boss’s decisions easier, faster, and safer—plus a challenge to rethink objection handling as a daily habit.

Whether you’re reporting to a VP or briefing the C-suite, this episode will help you shift from proving your team’s worth to steering leadership’s focus—at the right moment, with the right message.

🎯 Your Challenge: Email alex@lololai.com or tag Alex on LinkedIn with the next executive pain point you want decoded.

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

Connect: alex@lololai.com

🎙️ From 0 to 30 Prompts a Day (Executive Edition) – feat. Promptly Speaking

What happens when you go from never touching AI to using it 30 times a day? In this Executive Edition of Practical Prompting, we break it down step-by-step—without adding a single new chore to your calendar.

Act I: We tackle a pain point every executive knows too well: being looped into a sprawling, weeks-old email chain with zero context. You’ll hear exactly how to turn that time-sink into a 3-minute AI-powered “email chain autopsy” that leaves you with clarity, an agenda (if needed), and the right people in the room.

Act II: We unpack the Spark → Scaffold → Flywheel system for building AI habits that stick—starting with small, high-impact wins, adding structure to make them repeatable, and scaling until AI is a genuine business partner in strategy, decision-making, and execution.

And this week, there’s a twist—meet Promptly Speaking, my new AI co-host. With an English accent, a dry wit, and a knack for asking the questions you didn’t know you needed answered, she’s here to challenge my thinking, keep us grounded, and sneak in a joke or two.

Whether you’re an AI skeptic, a curious exec, or already halfway to 30 prompts a day, this episode will leave you with practical tactics—and maybe a laugh—to accelerate your own AI adoption.

🎯 Your Challenge: Email alex@lololai.com or tag Alex on LinkedIn with the next executive pain point you want decoded.

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

Connect: alex@lololai.com

Episode notes

🎙️ Guardrails & Governance – From Kitchen Table to Boardroom

Why does “governance” sound scary when it’s really just handing your kid scissors — plus the rule “only at the kitchen table, blade down”? In this Executive Edition of Practical Prompting, host Alex Kalish shows how the same guardrails that protect family photos can save your company millions in breach fines.

Act I: Tiny Guardrails, Big Impact

• Kid-Friendly Content Policy – A 150-word, emoji-powered house rule that keeps kids (and their data) safe in AI chats.
• Voice-Assistant Auto-Delete Drill – One prompt, three taps, and every Alexa recording purges itself after 90 days.

Skip the buzzwords—see how consent, clarity, coverage, and quick checks turn abstract “AI safety” into a fridge-magnet rule.

Act II: Risk & Compliance at Enterprise Scale

• “Tea” App Meltdown – Viral women-only dating app shipped Firebase keys in its code; 72 k selfies and 1.1 M DMs splashed across the internet.
• What to do Today – Changing thought processes from "we need a plan" to "we carved out an enterprise license."

Good intentions aren’t a defense; if an intern can git push an API key at 2 a.m., you need guardrails yesterday.

You’ll learn how to 🔍

• Translate “governance” into simple, repeatable household habits.
• Recognize potential issues before they hit the headlines.
• Establish governance without sacrificing speed.

🎯 Your Challenge: Email alex@lololai.com or tag Alex on LinkedIn with the next executive pain point you want decoded.

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

Connect: alex@lololai.com

🎙️ Half-Budget, Full Impact

What if your ops budget was cut in half—today—but your KPIs stayed the same?

In this Executive Edition of Practical Prompting, host Alex Kalish turns a high-pressure constraint into a strategy accelerator.

Act I: Household Constraints, Executive Mindset

What can GenAI do with 4 mouths to feed, $80, and a week of dinners? More than you'd think. Alex walks through how a simple one-liner prompt turned into a full dinner plan, shopping list, and prep schedule—in seconds. But the real lesson isn’t about food. It’s about constraint-stacking as a forcing function for smart trade-offs and AI-powered planning.

Act II: Strategy Under Pressure

Alex zooms out to the boardroom: what happens when you treat headcount plans, SLAs, or revenue goals the same way? Hear how one VP used a reusable GenAI prompt chain to simulate outcomes, cut FTEs by 30%, and accelerate throughput—all with KPI integrity intact.

You’ll learn how to:

• Frame goals in messy human language—and let GenAI structure the strategy.
• Generate decision-ready artifacts like vendor matrices, risk maps, and KPI deltas.
• Use GenAI like a co-strategist, not just a summarizer.

🎯 Your challenge: Take one constraint that’s been keeping you up at night, and throw it at GenAI—no polish, no perfection. Just start. Screenshot what you get and tag #PracticalPrompting.

Listen, rate, & review: Email alex@lololai.com or tag on LinkedIn with what topic you'd like to see covered. The first ones who do will get a complementary stop sign sticker with "Ask AI First".

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

Connect: alex@lololai.com

Grab your coffee and your passport: this episode shows how GenAI can plan a multi-city European getaway and become the everyday co-pilot you didn’t know you needed.

Act I: Vacation Wizardry

Tabs everywhere, brain in overdrive? Alex demonstrates a repeatable prompt that turns loyalty-point juggling and must-see lists into a polished 10-day itinerary in seconds. Learn the simple role → task → constraints template, the art of micro-iterations, and why you’ll never spreadsheet a trip again.

Act II: The 30-Prompt-a-Day Journey

Follow the progression from “I barely open ChatGPT” to firing off 30+ prompts a day. You’ll hear:

• Phase 1 – Sporadic: recipes and random dad jokes.
• Phase 2 – Discovery: “Wait, it can do that?” resume rewrites, SQL assists, meeting agendas.
• Phase 3 – Habitual: email drafts, stand-up notes, voice-to-prompt workflows, and a five-minute guardrail to stay focused.

Alex shares a habit-stack blueprint and a daily “Ask AI First” trigger that transforms friction points into instant leverage.

Listen, rate, & review: Track your prompts for one week. If you hit 10+ per day, post a screenshot with #PracticalPromptingPodcast and tag @Alex Kalish on LinkedIn. The first 50 listeners get the limited-edition stop-sign “Ask AI First” sticker for your laptop.

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

Connect: alex@lololai.com