All Episodes

November 4, 2025 36 mins

Chris Brogan shares some brutally honest insights about leadership, growth and being helpful. He's a self-proclaimed expert at failing, but what does that mean? And how can leaders learn from it to keep their organisations flexible and effective even as they grow at speed?

Ten-time author, executive coach, strategic advisor, writer, photographer and co-host of the internet’s Backpack Show and Playing For Time, Chris is a master communicator. As Chief of Staff at Appfire, he most recently helped steer the B2B SaaS company from $10m to $275m of ARR (annually recurring revenue). Despite this, he claims he's never been ‘capable or qualified’ for anything he's done professionally. 

This is a conversation packed with wisdom, experience and smart thinking. And a very dry reference to the Red Hot Chilli Peppers that went right over my head at the time. Listen to discover:

  • what Chris thinks is crucial about failure and failing,
  • the traits that make for great (and not so great) leaders,
  • why companies lose their elasticity as they grow - and what you can do about it,
  • what he wants to do for the rest of his life,
  • why he’s learning to code,
  • some excellent tips for cold email marketing, and 
  • the philosophical lessons we should take from the Red Hot Chilli Peppers.

Connect with Chris on LinkedIn: https://www.linkedin.com/in/cbrogan/

Sign-up for his newsletter: https://chrisbrogan.com/#newsletter

 

Check out that Anthony Kiedis/Red Hot Chilli Peppers reference: https://www.youtube.com/watch?v=8DyziWtkfBw

 

The report about the gender difference in confidence when it comes to apply for roles: https://hbr.org/2014/08/why-women-dont-apply-for-jobs-unless-theyre-100-qualified

 

And due credit to The Adaptavist Group's Jari Worsley for the story about his dad training spreadsheet users back in the day. Read more here: https://bit.ly/4onTjXJ

 

Further reading:

Chris Brogan ‘Social Media 101’ (affiliate link) https://uk.bookshop.org/a/15792/9780470621004

 

Chris Brogan & Julien Smith ‘The Impact Equation’ (affiliate link) https://uk.bookshop.org/a/15792/9780670922406

 

Ryan Holliday ‘ Ego Is The Enemy’ (affiliate link)  https://uk.bookshop.org/a/15792/9781781257029

 

Chris Whipple ‘The Gatekeepers’ (affiliate link) https://amzn.eu/d/1m2wNHl

 

-- Thanks for listening to Curious Business, the business podcast that brings you fresh insights, experiences and ideas to help you think differently about your business and marketing. My name is Stephen Morris. I help start-ups and scale-ups gain clarity, take action and ignite real momentum in their marketing and pipeline generation. If you'd like to know more, book a discovery call or sign-up for my monthly newsletter - The Prompt.
Mark as Played

Advertise With Us

Popular Podcasts

Stuff You Should Know
Ruthie's Table 4

Ruthie's Table 4

For more than 30 years The River Cafe in London, has been the home-from-home of artists, architects, designers, actors, collectors, writers, activists, and politicians. Michael Caine, Glenn Close, JJ Abrams, Steve McQueen, Victoria and David Beckham, and Lily Allen, are just some of the people who love to call The River Cafe home. On River Cafe Table 4, Rogers sits down with her customers—who have become friends—to talk about food memories. Table 4 explores how food impacts every aspect of our lives. “Foods is politics, food is cultural, food is how you express love, food is about your heritage, it defines who you and who you want to be,” says Rogers. Each week, Rogers invites her guest to reminisce about family suppers and first dates, what they cook, how they eat when performing, the restaurants they choose, and what food they seek when they need comfort. And to punctuate each episode of Table 4, guests such as Ralph Fiennes, Emily Blunt, and Alfonso Cuarón, read their favourite recipe from one of the best-selling River Cafe cookbooks. Table 4 itself, is situated near The River Cafe’s open kitchen, close to the bright pink wood-fired oven and next to the glossy yellow pass, where Ruthie oversees the restaurant. You are invited to take a seat at this intimate table and join the conversation. For more information, recipes, and ingredients, go to https://shoptherivercafe.co.uk/ Web: https://rivercafe.co.uk/ Instagram: www.instagram.com/therivercafelondon/ Facebook: https://en-gb.facebook.com/therivercafelondon/ For more podcasts from iHeartRadio, visit the iheartradio app, apple podcasts, or wherever you listen to your favorite shows. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.