S2 Ep4: How I turned $1000 into $320 MILLION | Nathan Barry
What does it really take to turn your audience into a multi-million dollar company?
Nathan Barry went from broke blogger to the founder Kit, a bootstrapped SaaS powerhouse generating $45 million a year in subscription revenue.
This episode is more than just a story.
It’s a masterclass in how creators can build real, scalable businesses, without investors, hype, or burnout.
We cover:
• How Nathan grew from $2K/month to $100K… then $500K… then $3M/month in revenue
• The Ladder of Wealth Creation and how to climb it step-by-step
• How to go from selling a $250 product to a $2,500+ product
• Why email is still the most powerful tool in the creator economy
• His framework for moving from low-ticket to high-ticket offers
• How the Flywheel Effect transformed his business and how you can build one too
• Why he turned down Spotify
• How creators can spot underpriced, overvalued opportunities
Whether you're just starting out or already have an audience, this conversation will challenge how you think about money, audience growth, and long-term success.
Sign up to Revolut Business at https://www.revolut.com/rb/wakeup and add money to your account before August 31st, 2025, to receive a £200 / $200 welcome bonus. Subscription fees and T&Cs apply. Available for new Business customers in the UK and US.
US Customers: Revolut is not a bank. Banking services are provided by Lead Bank, Member FDIC. The Revolut USA Prepaid Visa and Prepaid Mastercard are issued by Lead Bank pursuant to licensing by Visa(c) U.S.A. Inc. and Mastercard International for Mastercard cards. Your funds are FDIC insured up to $250,000 through Lead Bank, Member FDIC. See https://www.revolut.com/en-US/ for more details.
0:00 Introduction
2:10 Nathan’s Backstory
5:00 Celebrities on Kit
6:00 How to Make Great Content
8:42 Nathan's Childhood
12:23 Discovering Web Design
14:40 Writing Books
18:00 How to make a lot of money selling to a small audience**
20:00 Email Drives Everything
24:00 Writing 1,000 Words a Day for 600 Days
29:00 Life Transformation: $60K to $250K
30:55 Ladder of Wealth Curation
34:00 From $2K/Month to $100K/Month
35:42 Almost Gave Up
38:30 Getting ill
45:30 Doubling Down on Kit
53:00 Power of Word of Mouth
1:00:00 Jumping from $500K to $3M/Month
1:02:00 Why He Rejected Spotify
1:04:00 Building the Flywheel
1:13:30 Low-Ticket to High-Ticket Products
1:14:30 How Ryan Reynolds Became a Billionaire
1:17:00 Teaching Skills to People With Money
1:20:00 Chris’ Digital Product
1:25:00 Nathan’s Non-Flexing Philosophy
1:28:40 What’s the Difference Between a Strip Mall?
1:34:00 How Reese Witherspoon Became a Billionaire
1:37:55 Final Take: What Can People Wake Up To Today?
Follow Chris: https://www.instagram.com/chrisdonnellyofficial/?hl=en
Follow Nathan: https://www.instagram.com/nathanbarry/?hl=en
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S2 Ep3: The Brutal Truth About FAILURE You Need To Hear | Elizabeth Day
No one teaches you how to embrace failure, but what if that’s the only way to truly succeed?
Today, I’m sitting down with Elizabeth Day, bestselling author, journalist, and host of the How To Fail Podcast, the hit podcast that’s changed how millions of people think about setbacks.
Elizabeth opens up about the moments that shaped her: growing up in Northern Ireland, feeling like an outsider at school, the pursuit of confidence, and how repeated rejection eventually became her greatest superpower.
She also shares the deeply personal stories behind her success, from boarding school struggles to navigating miscarriage, online hate, and public life, and why your ability to fail well might be the most important skill you’ll ever learn.
If you’ve ever felt like you're behind, broken, or not enough, this one’s for you.
Sign up to Revolut Business at https://www.revolut.com/rb/wakeup and add money to your account before August 31st, 2025, to receive a £200 / $200 welcome bonus. Subscription fees and T&Cs apply. Available for new Business customers in the UK and US.
US Customers: Revolut is not a bank. Banking services are provided by Lead Bank, Member FDIC. The Revolut USA Prepaid Visa and Prepaid Mastercard are issued by Lead Bank pursuant to licensing by Visa(c) U.S.A. Inc. and Mastercard International for Mastercard cards. Your funds are FDIC insured up to $250,000 through Lead Bank, Member FDIC. See https://www.revolut.com/en-US/ for more details.
0:00 Introduction
1:40 Elizabeth & Chris’ experiences with IVF struggles
7:00 Self doubt in your 20s
9:55 Elizabeth’s early years
15:40 “Confidence in a muscle you can flex”
16:55 Elizabeth’s first job at 12
20:30 Gossip columnist
23:20 “Just do the hard thing over and over again”
24:50 Introverted Vs Extrovert
31:00 Understanding failure
35:20 If you're feeling lost watch this
39:15 Thoughts on Ozempic
41:15 How to balance it all
49:30 Elizabeth's IVF story
59:40 Sally Phillips opens up about failure
1:03:30 Kate Winslet opens up about failures
1:05:30 Psychic readings
1:13:30 Failing in your 20s
1:16:00 5 year plans
1:21:00 The importance of friendship
1:23:00 Work addiction
1:26:50 Conflict avoidant
1:29:20 Stop being a people pleaser
1:32:00 How to set boundaries
1:35:00 How to deal with negative opinions
1:40:20 Justin Baldoni & Blake Lively court case
1:44:50 Elizabeth being a CEO & Founder
Follow Chris: https://www.instagram.com/chrisdonnellyofficial/
Follow Elizabeth: https://www.instagram.com/elizabday/
Pre sale link: https://lnk.to/OneOfUsElizabethDay
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S2 Ep2: Shaolin Warrior Master WARNING The Collapse of The West! This Modern Habit Is Killing Millions!
You don’t need more motivation. You need mastery.
In this episode, I sat down with Master Shi Heng Yi one of the world’s most respected voices on self-discipline, inner strength, and mental clarity. He’s not here to give you life hacks. He’s here to teach you how to face the uncomfortable truth: that most of us are running from ourselves.
We unpack what it really means to live with presence, power, and purpose and how to stop letting your emotions, distractions, and past pain run the show.
From overcoming addiction to comfort to understanding why we are the cause of our suffering, this conversation is a blueprint for those ready to step out of autopilot and take their mind back.
If you’ve ever felt anxious, undisciplined, or like something’s missing, this is your wake-up call.
Chapters:
0:00 Introduction
1:10 Early Years
3:20 Rebelling
6:40 How to Deal with Comparison & Competitiveness
10:00 How to Figure Out the Purpose of Life
12:12 Epidemic of Addiction & Greed
17:00 What to Do When Times Get Hard
20:00 Pain & Failure Can Sometimes Be Good
25:05 Demon Hand, Buddha Heart
28:00 Is This the Life You Want to Live?
30:00 How Can People Motivate Themselves?
33:00 Why Discipline Is Needed
34:00 How to Confront Your Demons
35:30 Have You Got a Dead Corpse in the Basement?
40:30 Your Thoughts Become Who You Are
42:50 5 Hindrances to Sensory Growth
45:50 R.A.I.N. Method
48:00 How to Stop Getting Triggered
50:00 You Can’t Grow When Comfortable
54:20 How to Grow Your Heart
56:10 Consistency Is More Powerful Than Intensity
1:00:08 Failure vs. Success
1:02:15 How to Focus on Goals
1:05:00 How to Let Things Go
1:06:00 How to Bring the Shaolin Spirit into Your Life
Follow Chris: https://www.instagram.com/chrisdonnellyofficial/?hl=en
Follow Master Shi Heng Yi: https://www.instagram.com/shihengyi.online/?hl=en
Master Shi Heng Yi's Book: https://linktr.ee/shihengyi.online
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S2 Ep1: How to STOP Getting Defensive, Handle Difficult People & Take Back Your Power! Jefferson Fisher
You don’t need to shout to be heard. You don’t need to win every argument to be respected. And you don’t need to fear difficult conversations, if you know how to lead them.
In this episode, trial lawyer and #1 speaking coach Jefferson Fisher shares the communication frameworks that have made him one of the most trusted voices online for navigating conflict, setting boundaries, and speaking with confidence.
We explore why less is more when you speak, how to stay calm under pressure, and the one mindset shift that instantly makes you more magnetic in any room.
From boardrooms to relationships, Jefferson’s practical tools will help you argue less, say more, and lead without raising your voice.
If you’ve ever struggled with people pleasing, being heard, or standing your ground, this one’s for you.
Chapters:
0:00 Intro: Why Words Matter More Than Ever
1:30 Jefferson’s Backstory
4:50 Jefferson Powerful Online Voice
7:10 “What You Say Is Who You Are”
9:50 How to Spot a Liar
12:55 Nervous Before a Hard Conversation? Try This
15:20 Declutter Your Sentences, STOP Saying Um
17:45 Power of Speed & Tone in Speech
21:00 Why You Might Sound Like You're Lying
24:00 "Don’t Be a Waterfall, Be a Well"
27:00 How to Argue Less and Say More
30:00 How to Spot “Knots” in a Conversation
33:25 How to Lean Into Conflict
36:40 Feel an Argument Coming? Do This First
41:30 People Mirror Your Frequency, Use It Wisely
43:30 How to STOP Reacting to Insults
46:30 The Power of Letting Go
50:00 Stop Forcing Your Opinion, Try This Instead
56:00 The 3-Step Framework for Difficult Conversations
1:01:30 How to Argue Like a Lawyer
1:04:40 How to Say “NO” With Confidence
1:07:00 How to Clearly Set Boundaries
1:11:00 How to STOP People Pleasing
1:14:35 How to Stay Calm When Insulted
1:21:00 How to Apologise Properly
1:22:45 What to Say After a Bad Apology
1:25:30 How to Deal With a Narcissist
1:29:00 How to STOP Getting Defensive
1:30:30 Handling Insults at Work
1:33:00 How to Have Tough Conversations at Work
1:34:00 How Jefferson Leads His Business
Link to Book: https://www.jeffersonfisher.com/book
Follow Chris: https://www.instagram.com/chrisdonnellyofficial/?hl=en
Follow Jefferson: https://www.instagram.com/jefferson_fisher/?hl=en
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S1 Ep16: Psychologist Reveals Mental Hacks That Will Unlock Your Dream Life In 3 Months - Maya Raichoora
This episode might change the way you think about mindset forever.
At just 17, Maya Raichoora was diagnosed with a chronic illness that left her unable to walk, eat, or even attend school. Doctors told her she’d never recover fully.
But what changed everything wasn’t just treatment — it was visualisation.
Maya shares the exact moment her healing journey began, how she used mental imagery to rewire her brain, and the powerful mindset tools she now teaches in her new book “Visualise.”
If you’ve ever felt stuck, burnt out, or like you’re living in survival mode
This conversation is a blueprint for getting back to yourself.
Chapter:
00:00 – Introduction
02:31 – Introducing Maya
03:24 – Maya’s Early Life as a High Performer
04:09 – Diagnosed with Ulcerative Colitis
05:19 – The Mental and Physical Struggle
06:39 – Isolation and Shame
08:39 – Searching for a Cure Worldwide
09:39 – The Question That Changed Everything
10:39 – Visualising a New Future
12:09 – The Obsession with the Mind-Body Connection
13:09 – Turning Pain into Purpose
14:09 – How to Start Visualising
15:09 – Building Your Future Self Through Reps
16:39 – The Power of Slowing Down
19:09 – Mind Like a Lake: A Visualisation for Calm
20:39 – The Energy Diet No One Talks About
22:39 – Recognising Your Seasons
26:09 – Hibernation Mode for High Performers
28:09 – Spring, Summer, and Harvest Cycles
30:39 – Following Your Own Race
33:39 – Building a Character-Driven Identity
36:09 – Taking Radical Responsibility
39:39 – The Real Role of Social Media
42:09 – Internal vs External Validation
45:39 – When You're Overwhelmed by Feedback
48:39 – Building Mental Fitness Habits
51:39 – Celebrating the Present Moment
54:39 – Letting Go of the Hustle Guilt
57:39 – Learning to Delete, Not Just Add
01:00:39 – Visualising Nike-Level Mindset
01:03:39 – Book Writing, Reading, and Rewriting Beliefs
01:06:39 – Building Accessible Tools for Young People
01:09:39 – Future Plans for Mental Fitness Education
01:12:39 – Why We Avoid Hard Conversations
01:15:39 – 6 Vulnerable Questions That Build Deep Connection
01:18:39 – Managing Stress Through Language and Awareness
Follow Chris: https://www.instagram.com/chrisdonnellyofficial/?hl=en
Follow Maya: https://www.instagram.com/maya.mental.fitness/?hl=en
Link to book: https://www.penguin.co.uk/books/465180/visualise-by-raichoora-maya/9781846048524
A few years ago, I was just like many of you, figuring out the highs and lows of entrepreneurship, facing setbacks, and chasing breakthroughs. By 25, I had built and sold a leading digital marketing agency. By 30, I was co-founding Lottie, a health tech company transforming care solutions, and growing into one of the UK’s fastest-rising business creators. But along the way, I noticed something: the world is changing, yet most of us are still stuck playing by outdated rules.
That’s why I launched Wake Up, a podcast for people who are ready to rewrite the playbook. It’s not just about hearing incredible stories, it’s about taking those stories and turning them into real, actionable steps. Each week, I sit down with some of the most inspiring leaders, creators, and innovators to uncover their strategies, struggles, and unfiltered truths.
Wake Up isn’t here to inspire you for a moment, it’s here to empower you for a lifetime. Together, we’ll rethink the way we work, lead, and succeed in a world that demands new ideas. Thank you for joining the movement. Let’s wake up to what’s possible and create something extraordinary.
UK