Today, I’m joined by James Kuczynski, Creative Director at Duolingo, and Dan Salkey, Founding Partner at Small World, for a conversation on how to build truly entertaining brands.

Fresh off their SXSW panel titled "Entertain or Die", named after a report by Small World, we explore how Duolingo has built such a standout brand, particularly through the rise (and death...) of their iconic mascot, Duo.

In the first half of the episode, I chat with James about Duolingo’s brand success, why they decided to "kill off" their beloved mascot, and how giving creative autonomy to their team has been key to their growth. In the second half, I speak with Dan about the most entertaining brands in the world today—and the specific traits you can apply to make your own brand more entertaining.

Download the Entertain or Die report here.

Timestamps

00:00 - Start
00:47 - Part 1: James Kuczynski from Duolingo
01:22 - James’ background in marketing
03:23 - How James joined Duolingo
04:18 - What is Duolingo
06:34 - How Duolingo has used gamification to help people learn languages
09:47 - How is AI enhancing Duolingo?
11:20 - Is AI a threat to Duolingo?
12:13 - Why Duolingo created “Duo”, their mascot
15:47 - How the Duolingo owl evolved
17:56 - Duolingo’s April fools plans
20:00 - Why Duolingo killed off their mascot
23:57 - The results of Duo killing their mascot
25:08 - How partnerships have played a role in the success of Duolingo
28:02 - How Duo is bigger than A-list celebrities
29:26 - How Duolingo built such a huge social media following
32:08 - The importance of being in-house for growing Duolingo
33:17 - How Duolingo hires social media talent
34:34 - The thing that makes Duolingo stand out
36:32 - Part 2: Dan Salkey from Small World
37:15 - Why Small World created the Entertain or Die report
38:57 - How they identified the most entertaining brands on the planet
39:30 - What brands are the most entertaining?
40:41 - Why the most boring categories have most space to innovate
42:35 - The entertainment gap
44:07 - How can brands be more entertaining?
49:54 - Final advice on how brands can be more entertaining

In this episode, we deep dive into the irrational world of customer behaviour with legendary behavioural economist Dan Ariely. Dan reveals why we’re all predictably wrong, how tiny invisible cues can radically change price perception, and why effort makes things feel more valuable. We also unpack the real reason people fall for misinformation, how to rebuild trust in broken industries like insurance, and why letting customers choose their own price might just be your smartest move. If you want to understand what truly drives decisions — and how to use that insight to become a better marketer — this one’s unmissable.

Timestamps:

00:00:00 - Intro
00:00:50 - The story of Dan Ariely’s half beard
00:07:53 - Dan’s painful introduction into behavioural science
00:11:46 - Reaction to Jon’s house tragedy
00:15:11 - The hidden truths revealed by social science
00:21:43 - Invisible vs visible motivation
00:29:20 - How Dan would change insurance companies
00:33:30 - Lemonade insurance example
00:35:39 - Why the human brain is a vintage Swiss Army knife
00:38:08 - How context radically changes price perception (the relativity effect)
00:45:01 - Why you should let your customer choose their own price
00:47:11 - Why economists donate the least to charities
00:49:58 - Why effort greatly increases your price perception
01:00:06 - The real cause of misinformation and why it isn’t what you might think
01:12:18 - What will be Dan Ariely’s new book?
01:13:38 - Why we are so afraid of mistakes

Rory Sutherland returns to the Uncensored CMO podcast, tackling the economic crisis with his signature wit and wisdom. As ever, he offers a refreshingly unconventional perspective on the world’s biggest problems — and marketing’s role in solving them.

In this episode, Rory explores why marketing is more like a casino than a science, how to capitalise on your competitors’ blind spots, and what his unexpected TikTok fame has taught him. Expect laughs, left-field insights, and the kind of brilliantly bizarre anecdotes only Rory can deliver.

Timestamps

00:00 - Intro
01:03 - Are we looking in the wrong place for growth?
05:33 - Should we slow down our adoption of AI?
09:08 - What marketers and the police have in common
14:40 - Marketing is a casino
17:42 - The most transformative behavioural science insights
19:47 - Take what your competition are doing badly and double down on it
26:20 - Fame is a luck multiplier
32:43 - Why AO add bears to every order
37:19 - How Rory would boost growth in the economy?
47:13 - What has Rory been profoundly wrong about and why