Nathan Barry gave away millions of dollars to his family—and says it was the best financial decision he ever made. As CEO of ConvertKit, he'd reached a level of wealth that changed what money could do, not just for him, but for the people he loved most. In this conversation, Nathan walks through the moment he realized his parents could retire immediately if he simply wrote them a check, the calculations that made it possible, and why he believes optimizing for experiences—not net worth—is the real endgame of financial independence.
Introduction to Nathan Barry
Nathan founded ConvertKit in 2013, an email service provider now serving thousands of creators. He's been part of the FI community for years, building his company using FI fundamentals while reimagining what wealth can accomplish.
Discovering financial independence
Nathan reflects on finding the FI community through figures like Mr. Money Mustache and how those ideas shaped his approach to building a business and living intentionally.
Skill acquisition leads to increased income potential
When you focus on learning high-value skills, increasing income becomes far easier than cutting expenses. Nathan shares how this mindset opened doors in his entrepreneurial journey.
Value of experiences over material goods
The conversation emphasizes investing in experiences—trips to Disneyland, sailing adventures—rather than accumulating possessions. This aligns with Nathan's philosophy of spending money on what creates lasting memories.
How Close Are You to Financial Independence?
Free calculators, a personalized FI roadmap, and a community of 25K+ on the same journey.
Flying with skills
Nathan discusses how developing new capabilities—whether in business, creativity, or life—compounds over time and leads to better financial outcomes and more fulfilling experiences.
Ready to take the next step?
Put what you heard into action with these tools and community.
Your unique perspective creates a distinct message
There are no unique messages, only unique messengers. Nathan explains why finding your voice and sharing your story matters more than trying to say something no one has ever said.
Nathan's impactful family gifts
The most moving part of the episode: Nathan walks through his decision to give substantial funds to his family, allowing them to retire comfortably. He breaks down the math, the emotional impact, and why he chose to share wealth now rather than later.
Money can be a powerful tool for positive change
With financial resources, you can create meaningful impacts in the lives of those you care about—whether that's funding retirements, enabling experiences, or removing financial stress.
Using money for impactful experiences
Examples of spending on experiences that matter: family trips, travel rewards, and investments in relationships that pay dividends in memories and connection.
Related Resources:
Top Travel Card
Ready to unlock a world of free travel? Start with the Chase Sapphire Preferred® Card
$95 annual fee | Earn 75,000 bonus points
Best Card for Side Hustlers and Business Owners
Side hustlers! With the Ink Business Preferred® Credit Card you can earn free travel from your business expenses.
$95 annual fee | Earn 100,000 bonus points
Most Flexible Travel Card
The Capital One Venture Rewards Credit Card can be used to offset almost any travel expense.
$95 annual fee | Earn more than $1,000 in Travel Bonuses with a limited-time $300 Capital One Travel stays credit, plus earn 75,000 bonus miles once you spend $4,000 on purchases within the first 3 months of account opening—that's more than $1,000 in travel value
ChooseFI has partnered with CardRatings for our coverage of credit card products. ChooseFI and CardRatings may receive a commission from card issuers.
- ConvertKit
- Die With Zero by Bill Perkins