New to the Podcast? Here Are the 'How I Failed in Business' Episodes You Need to Hear First
So you have just discovered How I Failed in Business. Welcome. Pull up a chair, plug in some headphones, and prepare to feel significantly better about your own business journey.
The back catalogue has grown into something we are genuinely proud of — a library of honest, funny, and often surprisingly moving conversations with real business owners who have been through the fire and come out the other side. Every episode is different. Every guest brings a completely unique story.
But we know what it is like to discover a podcast with a large back catalogue and feel mildly overwhelmed about where to start. So we have done the work for you. Here are some of the themes and types of episodes that our listeners consistently love — with a guide to what to expect from each.
Start with the ones that make you feel less alone
If you are going through a tough period in your business right now — and many people find this podcast precisely when things are hard — start with an episode where the guest is raw and honest about a moment of genuine crisis. A point where they were not sure they were going to make it through.
These are the episodes that generate the most messages from listeners. Not because failure is entertaining (though sometimes the stories are), but because hearing someone else articulate the exact feeling you are sitting with right now — that specific 3am dread, that creeping sense of 'have I made a terrible mistake?' — is extraordinarily reassuring.
You are not the only person who has felt this way. Not even close. And more importantly: the people in our episodes who felt it came out the other side. That is worth hearing.
Then try the ones where the failure turned into something unexpected
Some of our most popular episodes follow a structure that sounds almost like a cliché but is absolutely true: the business that failed became the seed of something far better. The client who walked away forced the pivot that saved the company. The deal that collapsed opened a door to something bigger.
These episodes are not about putting a positive spin on difficulty. They are about the genuine, specific, accidental ways that going wrong can redirect you somewhere better. The founders who share these stories are not optimists by nature — they are realists who have been surprised by their own journeys.
If you want to understand why 'failure' is such a misleading word for what most business setbacks actually are, these are the episodes that will reframe it for you.
The ones that are just really funny
Look — not every episode is deep. Some of them are just an absolute laugh from start to finish. Business disasters that are so specific, so perfectly timed, so utterly avoidable in hindsight that you cannot help but howl.
There is something about the particular flavour of professional embarrassment that is universally funny. The pitch that went catastrophically wrong in real time. The email that was sent to entirely the wrong person. The product launch event where literally nothing worked as planned.
These are the episodes our listeners share most often. They end up in WhatsApp groups with captions like 'you need to hear this' and 'this made me choke on my lunch.' If you want to introduce a friend to the podcast, one of the funnier episodes is usually the best entry point.
The ones to listen to when you are thinking about starting a business
We get a significant number of listeners who found the podcast during the 'I am thinking about leaving my job and doing my own thing but I am absolutely terrified' phase. If that is you — first of all, completely normal. Second of all, this podcast is genuinely useful preparation.
The episodes where guests reflect on what they wish they had known before starting are consistently among our most listened-to. The things no one tells you. The assumptions that turned out to be wrong. The things that seem scary from the outside but are actually fine, and the things that seem fine but turn out to be genuinely hard.
Starting a business is one of the most exciting and terrifying things a person can do. We think knowing what you are getting into — the real version, not the LinkedIn version — is the best possible way to set yourself up for success.
How to make the most of the back catalogue
Our advice: do not try to listen chronologically. Pick an episode based on the guest description or the topic that resonates most with where you are right now. Every episode stands alone — there is no running thread that requires context from previous episodes.
And if you find an episode that really lands, share it. Send it to someone who is going through something hard in their business. Drop it in your team WhatsApp. Leave us a review on Spotify or Apple Podcasts — it genuinely helps more people find the show.
Want to know more?
Search 'How I Failed in Business' on Spotify, Apple Podcasts, Amazon Music, or any major streaming platform. Or visit www.howifailedinbusiness.co.uk to browse episodes and find out more.
And if you love what you hear — tell a friend. Word of mouth is how this podcast has grown, and we are grateful for every single listener who has been part of it.