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

Scott Galloway (Prof G) has returned to the Uncensored CMO podcast for a second time, in a special live episode. Galloway is Professor of Marketing at NYU Stern School of Business and host of the Prof G and Pivot podcasts. He joins Jon in a special live episode in London and lives up to his billing as the most uncensored guest of all time. Scott takes big swings at the advertising industry throughout the episode - despite the audience of CMOs - claiming that the days of the CMO are numbered. He continues with his damning commentary on why the era of brand is dead, why rage is the new sex, why young men are in trouble and what marketers need to do in the age of AI.

Timestamps

00:00 - Intro
02:15 - How does Scott deal with the online negativity?
09:00 - Why the CEO saviours of social media won’t be turning up
16:13 - Scott’s thoughts on the Adolescence Netflix show
23:51 - Why marketers need to do the hard things
27:56 - How does Prof G assess a business opportunity
33:36 - What corporate employees can learn from entrepreneurship
40:22 - Why the CMOs days are numbered
47:33 - How should marketers approach AI
56:06 - What things has Prof G been profoundly wrong about

Thank you to System1 for making the live event possible.

Credits

Host: Jon Evans
Executive Producer: James McKinven
Director: Kerry Collinge
Event management: Lara Zwirn, Gen Norris
Social media: Sam Price
Event graphics: Colin Jenkinson
Production: Kinura

Live from Adobe Summit in Las Vegas, in this bonus triple header, Jon speaks with Colin Fleming (ServiceNow), Stacy Martinet (Adobe) and Billy Seabrook (IBM) about the hot topic in marketing today, AI, and what a new wave of agentic AI technology means for marketers.

Timestamps

00:00 - Intro
00:51 - Part 1: Colin Fleming
01:51 - The things people don’t understand about B2B marketing
03:32 - How AI is having an impact on marketing
05:29 - ServiceNow’s relationship with Adobe
06:21 - Advice to marketers to stay on cutting edge of AI
08:47 - Part 2: Billy Seabrook IBM
09:17 - Where are we on this AI journey
11:31 - Principles of an effective campaign using AI
13:02 - How effective has AI been for IBM
18:16 - What’s next when AI at scale becomes the norm?
21:08 - AI: a threat or an opportunity?
22:06 - Part 3: Stacy Martinet
22:33 - Stacy’s role at Adobe
23:18 - What makes great marketing for marketers?
24:12 - Communicating all the changes in marketing (specifically with AI)
25:15 - What is Agentic AI and what are it’s use cases?
28:27 - How technology is used to enhance creativity
30:31 - Tips on how to utilize agentic AI
31:43 - How to future proof our marketing
32:48 - What goes into creating an event like Adobe Summit

00:00 - Intro
00:51 - Part 1: Colin Fleming
01:51 - The things people don’t understand about B2B marketing
03:32 - How AI is having an impact on marketing
05:29 - ServiceNow’s relationship with Adobe
06:21 - Advice to marketers to stay on cutting edge of AI
08:47 - Part 2: Billy Seabrook IBM
09:17 - Where are we on this AI journey
11:31 - Principles of an effective campaign using AI
13:02 - How effective has AI been for IBM
18:16 - What’s next when AI at scale becomes the norm?
21:08 - AI: a threat or an opportunity?
22:06 - Part 3: Stacy Martinet
22:33 - Stacy’s role at Adobe
23:18 - What makes great marketing for marketers?
24:12 - Communicating all the changes in marketing (specifically with AI)
25:15 - What is Agentic AI and what are it’s use cases?
28:27 - How technology is used to enhance creativity
30:31 - Tips on how to utilize agentic AI
31:43 - How to future proof our marketing
32:48 - What goes into creating an event like Adobe Summit

Seth Matlins is the Managing Director of the Forbes Forbes CMO Network, where he oversees the annual Forbes World's Most Influential CMOs List, the Forbes Entrepreneurial CMO 50 List, the Forbes CMO Summit, the Forbes European CMO Summit, and an expanding marketing content portfolio. Seth is an award-winning marketer, who has spent a career in and advising the C-suite of dozens of the 100 most valuable brands globally.

Timestamps

00:00 - Intro
00:45 - Seth’s new podcast
02:58 - Why are there not enough CMOs becoming CEOs
05:28 - Marketing needs much better marketing
07:36 - Seth’s career history
08:00 - Working jobs that have never existed before
11:41 - Scars from being a failed entrepreneur
13:24 - Making unexpected connections between fields
18:23 - Why organisations need to trust their marketers
20:26 - What makes a CMO influential
26:29 - Everyone is a brand manager
28:35 - How CMOs can be more influential
35:13 - The world’s most entrepreneurial CMOs
41:12 - What makes a CMO entrepreneurial
46:22 - Doing a lot with little
47:02 - What is changing for CMOs in 2025

Today Jon talks with Eugenia Zalis, CMO for one of the most iconic sweet brands in the world, Oreo. We talk about their "stay playful" positioning, incredible brand collaborations (with the likes of Coca-Cola and Post Malone) and some of the interesting innovations the brand has worked on.

Timestamps
00:00 - Intro
00:46 - Eugenia’s marketing journey
01:33 - What can we learn from the Unilever approach to marketing?
02:27 - How Dove turned into the brand it is today
05:42 - How Eugenia started with Oreo
06:33 - The “stay playful” positioning
09:49 - The best way to eat an Oreo cookie
11:08 - Managing a 110 year old brand
12:14 - The Oreo playbook for marketing in different regions
15:18 - Oreo’s collab with Coca-Cola
18:49 - Oreo’s approach to innovation
21:14 - System1 testing on Oreo innovations
23:40 - Innovations from around the world
25:23 - The surprising Coca-Cola collaboration
25:52 - Oreo’s SuperBowl ad in 2024
28:34 - Winning a Cannes Lion for a tweet
30:34 - Why is humour not used more
35:37 - Oreo x Post Malone collab
38:07 - Creative process for collabs
39:02 - How to lead a $4.5b organisation
43:57 - Advice to aspiring CMOs

Cadillac is an iconic American brand who are navigating the shift to electrification in the automotive industry and have partnered up with 72andSunny to launch their brand new campaign “Let’s Take the Cadillac. So today, Melissa Grady Dias, CMO of Cadillac, and Marianne Malina, President of 72andSunny join Jon to talk about working with a new agency and launching their first campaign together.

Timestamps

00:00 - Intro
03:53 - Marianne’s background
06:49 - How to manage a brand like Cadillac
08:34 - How EV’s are changing the industry
13:53 - How do you change your marketing for EVs
15:08 - Insights and inception of “Let’s Take the Cadillac”
17:56 - Developing the “Let’s Take the Cadillac” campaign
21:41 - How to launch a new car
23:39 - Building the campaign for different formats
25:42 - 72andSunny and Cadillac’s first campaign together
28:11 - Challenging the conformity in car advertising
30:48 - Why brand is so important for car purchasing
32:31 - Leading the marketing agenda inside a big org like General Motors
34:24 - In car Cadillac Car-aoke
35:22 - Melissa’s song
36:13 - Coolest feature about Escalade IQ
38:37 - Creating a luxury experience
39:27 - Choosing your car as CMO of Cadillac
40:57 - Creating a premium vehicle
42:53 - Thoughts on the Escalade IQ