Wake Up with Chris Donnelly S2 Ep4: How I turned $1000 into $320 MILLION | Nathan Barry
Aug 14, 2025
01:38:50
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
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