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Jon and Kory discuss why humour is a serious advantage for brands, leaders and anyone trying to earn attention. They explore the science behind why humour makes ideas more memorable, why funny advertising has become less common, and the important difference between trying to be amusing and using humour to reveal a truth.
The conversation looks at what it takes to create the conditions for humour to thrive: giving people permission to take creative risks, planning for it rather than treating it as an afterthought, and understanding why brands such as Liquid Death make it look effortless.
A useful case for taking the work seriously, without always taking yourself quite so seriously.
Timestamps
00:00 - Start
01:44 - The serious case for humour
03:46 - The science behind humour
04:48 - Why humour is good for brands
06:28 - Why we are seeing less funny ads
09:23 - Humour touches on truth
11:17 - How to create the conditions for humour to thrive
14:25 - Why the best brands plan humour
17:38 - Why Liquid Death are so funny
19:37 - Can you use humour in a business context?
Jon and Kory discuss why persuasion is one of the most important, and overlooked, skills in leadership.
Getting an idea approved is rarely about delivering the perfect argument in a meeting. It starts earlier: asking better questions, listening closely, understanding what different people need, and finding the stories that make an idea feel relevant rather than imposed.
They explore the role of verbal and non-verbal communication, why the meeting is never really just the meeting, and how to build support before a decision is formally on the table. Kory also shares practical lessons from winning over her own board, persuading an organisation to take risks, and turning advocates into people who will sell the idea when you are not in the room.
A practical episode for leaders who need to influence without forcing, build alignment without endless consensus, and give their best ideas a genuine chance of happening.
Links
Timestamps
00:00 - Start
00:56 - Is persuasion one of the secrets to being a successful leader?
02:24 - The importance of asking questions
05:00 - The art of listening
08:09 - Verbal and non verbal communication
10:49 - The power of communicating through stories
13:43 - The meeting is never actually the meeting
17:26 - How Kory sold So Many Dicks to her board
20:08 - Pursauding your company to take risks
21:17 - Getting advocates to sell your idea
26:03 - Identifying your leverage
Jon and Kory discuss the Wiseman’s 15 building blocks of customer obsession: a practical framework for turning customer-first intentions into the way an organisation actually works, exemplified by Dutch Bros.
As always, Kory brings the data behind customer-obsessed organisations before the duo discuss why internal politics so often gets in the way, and whether founder-led businesses have a natural advantage when it comes to staying close to the people they serve.
From empowering frontline teams to reading every customer complaint, they unpack the behaviours that make customer obsession tangible rather than a line in a values document. They also draw on lessons from Unreasonable Hospitality, challenge the limitations of the golden rule, and consider how leaders can embed a customer-first mindset across the business.
Links
Timestamps
00:00 - Start
00:40 - Are you really obsessed with your customer?
01:59 - The data behind customer obsessed organisations
03:08 - Why internal politics gets in the way of the customer
05:15 - Are founder-led companies more customer led?
06:42 - The Wiseman’s building blocks
08:47 - Jon’s favourite customer first principles
10:25 - Example of empowering the front lines
13:11 - Kory’s favourite customer first principle
14:20 - Talking through all the Wiseman building blocks
17:13 - Why Kory reads all of e.l.f.’s customer complaints
19:13 - Customer first lessons from Unreasonable Hospitality
23:48 - Why Kory doesn’t like the golden rule
24:45 - How to embed these principles into your organisation
Jon and Kory discuss how small, consistent improvements can transform team performance 38x in just 1 year. Using lessons from elite cycling and Team Sky’s famously obsessive approach to marginal gains, they explore why high-performing teams rarely improve through one dramatic intervention. Instead, progress comes from making incremental improvements that compound over time.
Links
Timestamps
00:00 - Start
00:24 - Why Jon always wears black
02:45 - The compounding power of incremental gains
05:16 - Lessons from high performance sport
06:48 - The insane 1% improvements Team Sky made to win the Tour De France
11:21 - Applying cycling lessons to leadership
13:52 - Why you need to ask for feedback
16:27 - Just start
17:10 - How to see if you’ve actually made progress
20:28 - The paradoxical data on incremental progress
Jon and Kory discuss why making good decisions is one of the hardest – and most important – parts of leadership, and share the frameworks they use to make better choices when the answer isn't obvious.
From knowing when to trust the data and when to follow your gut, to de-risking big decisions and playing “angel's advocate”, they explore practical ways to challenge your own thinking. They unpack Solomon's paradox, the 10:10:10 rule, automatic negative thoughts and why sometimes the smartest thing you can do is ask someone else for help.
They also explore what happens when you stop actively thinking about a problem, some surprisingly useful Japanese wisdom, and one particularly simple test: would you make the same decision drunk?
Whether you're facing a huge strategic choice or simply stuck overthinking, these are 9 tools to help you make decisions with greater clarity and confidence.
Links
Timestamps
00:00 - Start
00:26 - Why Jon looks “savagely tanned”
01:19 - Why decision making is hard
04:16 - When you need to trust the data or your gut
06:43 - How to make a decision
07:29 - How to de risk a decision
09:30 - Try playing “angel’s advocate”
10:50 - Solomon’s paradox when making a decision
11:51 - Squash the ants (automatic negative thoughts)
12:23 - The 10:10:10 rule
14:36 - Ask for help
15:22 - Make space for your default mode network
17:06 - Would you make the same decision drunk?
17:47 - Japanese wisdom for decision making
20:29 - The stats on why this is important
Today Kory shares the lessons from taking her leadership team offsite and deliberately putting them into an unfamiliar environment - a horse ranch. Jon and Kory explore why pattern disruption can help teams break old habits, the difference between a group of strong individual contributors and a genuinely connected team, and why getting outside your comfort zone can reveal how you really work together.
They also discuss the language of connection, learning to ask for help, why pressure isn't always the answer, and how to turn an offsite from a memorable experience into lasting behavioural change. Because however busy your team feels, sometimes stepping away from the work is exactly what helps you do the work better.
Links
Timestamps
00:00 - Start
00:37 - Why Kory takes her team offsite
03:01 - Why you need to transform your team
04:14 - The power of pattern disruption
07:13 - Individual contributors vs working as a team
11:20 - Going out of your comfort zone
13:40 - The language of connection
18:21 - Learning how to ask for help
23:44 - The power is not in the pressure, it’s in the release
25:40 - How Kory is implementing the lessons in the team
27:03 - You’re too busy to not do this
Today, Jon and Kory open up their personal leadership toolbox, sharing the mental models and frameworks they rely on to make better decisions, communicate more effectively, and build high-performing teams.
From understanding your audience before creating content to aligning teams around a clear vision, raising the bar through belief and repetition, and creating dedicated thinking time, these are the practical tools that have shaped their careers. They also discuss why spending time with people smarter than you is one of the fastest ways to grow, and finish with the one framework that underpins everything else.
Timestamps
00:00 - Start
01:11 - Tools for your toolbox (in work and life)
01:57 - Framework 1: A.B.C. (Audience Before Content)
07:43 - Framework 2: A.B.C. (Always Be Curious)
09:14 - Framework 3: V.A.E. (Vision, Alignment, Execution)
13:43 - Framework 4: Raising the B.A.R. (Belief, Attention, Repetition)
18:08 - Bonus tool: spend time with people smarter than you
18:36 - Framework 5: 3, 5, 7, 9
22:31 - Framework 6: T Time!
26:43 - The framework to rule all frameworks
Today Jon and Kory explore the leadership habits that keep successful organisations moving forward. Drawing on research, personal experience and examples from some of the world's best businesses, they discuss why the strongest leaders surround themselves with people who will tell them the truth, stay relentlessly close to their customers, and never shy away from difficult conversations.
Timestamps
00:00 - Start
00:56 - How to stay grounded when you’re successful
02:52 - Does success drive complacency?
04:14 - What the data says about successful companies
06:07 - You need people that are prepared to tell you the truth
09:25 - Why you need to have the tough conversations
12:45 - Spend time with your customer
15:07 - The power of saying no
17:42 - Working with the right people
23:06 - Define your organisation
25:22 - Play to win
For decades, marketers have relied on the traditional 4 Ps: Product, Price, Place and Promotion. But as the role of the CMO has evolved, so too have the skills needed to succeed as leaders.
Today, Jon and Kory introduce a new framework for modern marketing leadership, inspired by research Jon conducted with TikTok. Rather than focusing on the marketing mix, these five Ps focus on what today's leaders need to excel inside their organisations: People, Planning, Persuasion and Performance. (Plus a bonus P that isn't a P - Storytelling.)
Timestamps
00:00 - Start
00:48 - A new set of marketing Ps
04:38 - P1 - People
08:05 - P2 - Planning
14:57 - P3 - Persuasion
23:52 - P4 - Performance
28:55 - P5 - Storytelling
Launching a brand is one of the hardest things you can do. Today, Jon and Kory break down the principles they've learned from building brands, products and podcasts from the ground up.
They explore the three ingredients every successful launch needs: a crystal-clear value proposition, surrounding yourself with exceptional people, and the persistence to keep going when progress feels slow. Along the way, they discuss why we're often too close to our own ideas, how constraints can become a competitive advantage, and why the best launches rarely happen by accident.
Timestamps
00:00 - Start
00:48 - How hard is it to build a brand from scratch?
02:52 - The 3 things that need to be true for a succesful launch
03:24 - Having a clear value prop
10:55 - Are we too close to our own proposition?
15:02 - Surround yourself with greatness
20:50 - Persistence
23:59 - The power of constraint
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