Ever stared at a blank email wondering how to phrase something important, or walked into a meeting wishing you'd actually prepared? Well, you're not alone!

Joe Downs and Peter Swain kick things off with the Dear Idiots mailbag, tackling a listener question from someone managing eight Airbnbs and planning a shipping container home using AI workflows to optimize both.

Then they flip the script on the old "stay late and grind" career myth, showing how ChatGPT for business and Claude can make you look like the smartest person in any room.

Finally, they walk through the "Side Hustle Figure Outer", a step-by-step process to discover your zone of genius, validate your idea, and figure out if entrepreneurship is actually for you.

If you've got skills, a couple of spare hours a week, and a dream of financial freedom, this one's for you.

Listen For

:21 How can AI help you get promoted even if you are not the hardest worker?
2:49 How do you use AI to optimize Airbnb occupancy, pricing, and listings?
9:11 How can AI build you a 30 day learning plan before you spend six figures?14:20 Why is AI not trustworthy for yes or no feasibility answers on big investments?
28:09 How do you prompt AI to find insights that make you look like a rockstar in a meeting?

Links Mentioned

Gemini AI (by Google)

ElevenLabs

Notebook 11

Read.ai

Otter.ai

Fireflies.ai

Nano Banana 2

Claude AI (by Anthropic)

Wey App

Email the “Idiots” Joe and Peter

Joe Downs

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Peter Swain

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Ever wish you could outsource that awkward family talk to someone else?

Joe Downs and Peter Swain dive deep into how AI can prep you for life’s toughest conversations, from asking for a raise to confronting aging parents about care.

With practical examples, listener questions, and real-life stories (including how Peter used AI to co-parent from 3,000 miles away), they show how the right context and prompts can turn emotionally fragile moments into calm, productive outcomes.

If you’ve been putting off a talk that keeps you up at night, this episode is your roadmap—and AI is your new conversation coach.

Listen For

:22 How Can AI Help You Prepare for the Hardest Conversation You’ve Been Avoiding?

3:56 What’s the Right Way for Artists to Use AI Without Copying Other Creators?

12:40 How Do You Build a Master Context Document So AI Actually Gives Smart Advice?

23:12 How Can AI Reframe Fear Before Asking for a Raise or Having a Money Talk?

30:04 What Happens When You Let AI Challenge Your Assumptions Before a Parenting Decision?

Email the “Idiots” Joe and Peter

Joe Downs

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Peter Swain

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Are you planning for Valentine’s Day or just winging it…again?

Joe Downs and Peter Swain reveal how AI can turn your last-minute panic into a masterclass of thoughtful planning.

Using Valentine's Day as the premise, they dive deep into how AI can help plan meaningful experiences…not just dates, but everything from corporate retreats to Super Bowl parties.

Peter walks us through a repeatable framework for feeding context into tools like Claude and ChatGPT to create personalized, impactful plans.

The duo exposes how fear, procrastination, and outdated playbooks sabotage our best intentions and how AI can remove that pressure.

Whether you’ve been married 20 years or are trying not to blow your fifth date, this episode turns AI into your secret relationship and logistics weapon.

Listen For

4:08 What’s the Right Prompt to Help AI Plan a Memorable Date?

9:17 Why Do People Freeze Up When Talking to AI?

12:25 What’s Your Real Objective for Valentine’s Day?

26:20 How Can AI Handle All the Logistics of an Event?

Email the “Idiots” Joe and Peter

Joe Downs

Website | Email | LinkedIn | YouTube

Peter Swain

Website | Email | LinkedIn | X