Season 2 | Episode 47 | The One With the Furry Confusion

This week on How I Failed in Business, slightly inappropriate and very educational… whether we wanted them to be or not.

We kick things off with a nostalgic trip back to the Covid years — from Zoom quizzes and bizarre lockdown rules, to the business decisions people made during that strange time (some better than others).

Rob reflects on working through the chaos while others were allegedly living their best furlough lives, and Megan shares how she managed to redeem herself after a recent travel booking disaster with a suspiciously cheap flight to Venice.

From there, we get an update on Rob’s new side hustle as a reseller — including tiny profits, unexpected customer complaints, and a woman named Janet who had very strong feelings about missing straps. It’s a masterclass in customer service, patience, and questioning your life choices.

We also share some exciting behind-the-scenes updates about the podcast — including plans for Season Three, a brand-new set, fresh games, and bigger ambitions as the show continues to grow.

And of course, we dive into Grievance Gurus, where this week’s stories take a very unexpected turn. From accidental waxing mishaps, to a client who started purring during and introduced the team to the concept of a “furry lifestyle,” it’s safe to say this segment escalates quickly.

In this episode, expect:

• Throwbacks & questionable business decisions
• Rob’s reseller adventures (and customer complaints from Janet)
• Bargain flights, travel wins & redemption arcs ✈️
• Big updates about Season Three of the podcast
• Waxing disasters & salon horror stories
• A very unexpected introduction to the world of “furries” 😅

If you like your business podcasts honest, funny, and occasionally completely unhinged — this one’s for you.

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New episodes of How I Failed in Business every Tuesday — real stories, real mistakes, and grievances that spiral faster than expected. 🎙️

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