The $300M Founder That Lives on a Farm and Flies Planes | Nathan Barry

02/15/24 • 75 min

Nathan Barry, founder of ConvertKit, shares his journey from software designer to content creator to software founder. With ConvertKit now sending 2.5 billion emails per month and generating $40 million in revenue, Nathan discusses the power of building an audience and leveraging it to create long-term enterprise value. He also delves into his passion for flying and the parallels between flying and entrepreneurship. Nathan emphasizes the importance of having goals outside of work and optimizing for the journey rather than just the destination.

Watch the full interview here: https://youtu.be/vuwfio0Uw4Y

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TIME-STAMPED SHOW NOTES:

(00:00) Nathan Barry introduces himself and his journey from software designer to software founder
(02:57) Nathan Barry discusses his passion for flying and the process of getting a pilot's license
(06:43) Nathan Barry expresses his goal of using flying for both personal and work-related purposes
(08:14) Nathan Barry discusses the limitations and considerations of owning a larger plane
(09:49) Eric asks Nathan about the payment structure for the pilot.
(12:30) Nathan talks about his podcast and the journey of building an audience.
(14:02) Nathan shares the story of Mark Sisson and the value of redirecting audience attention to a product.
(15:08) Nathan explains the power of an audience in promoting and selling products.
(16:03) Nathan discusses the success of Mark Sisson's Primal Kitchen and the value of an audience.
(18:19) Nathan talks about the three rules for building an audience and creating enterprise value.
(19:46) Nathan shares his experience building ConvertKit and its long-term enterprise value.
(20:05) Nathan Barry and Eric Siu discuss the potential of agencies as successful businesses.
(21:25) Nathan Barry shares his perspective on monetization options for creators.
(25:52) Nathan Barry talks about the current growth and future potential of newsletters.
(29:46) Nathan Barry shares a story about how having an audience can shortcut career paths.
(31:24) Transitioning from personal brand to building a business
(32:22) Using personal brand to drive attention to other businesses
(34:21) Debate on the success of creator-led agencies
(39:15) Strategies for growing Twitter following
(42:09) Repackaging and reposting content for maximum reach
(45:47) Nathan Barry is transparent about his financials to inspire others.
(52:59) Nathan Barry discusses the flywheel strategy for growing a newsletter.
(55:30) Advertising as a loop closer drives new subscribers for sponsorships.
(57:54) Growing the newsletter audience leads to book sales and more opportunities.
(59:59) Building network effects between creators through the Creator Network.
(1:01:36) Convertkit's Creator Network and Spark Loop acquisition.
(1:06:09) Nathan suggests using partnerships with other blogs to promote the subscription service and increase email sign-ups.
(1:07:38) Eric asks Nathan about his quote "making money is a skill" and Nathan explains that building a successful business requires developing a range of skills.
(1:11:37) Nathan shares where people can find him online, including his podcast and newsletter.

—

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Watch the full interview here: https://youtu.be/vuwfio0Uw4Y

Don’t forget to help us grow by subscribing and liking on YouTube!

TIME-STAMPED SHOW NOTES:

(00:00) Nathan Barry introduces himself and his journey from software designer to software founder
(02:57) Nathan Barry discusses his passion for flying and the process of getting a pilot's license
(06:43) Nathan Barry expresses his goal of using flying for both personal and work-related purposes
(08:14) Nathan Barry discusses the limitations and considerations of owning a larger plane
(09:49) Eric asks Nathan about the payment structure for the pilot.
(12:30) Nathan talks about his podcast and the journey of building an audience.
(14:02) Nathan shares the story of Mark Sisson and the value of redirecting audience attention to a product.
(15:08) Nathan explains the power of an audience in promoting and selling products.
(16:03) Nathan discusses the success of Mark Sisson's Primal Kitchen and the value of an audience.
(18:19) Nathan talks about the three rules for building an audience and creating enterprise value.
(19:46) Nathan shares his experience building ConvertKit and its long-term enterprise value.
(20:05) Nathan Barry and Eric Siu discuss the potential of agencies as successful businesses.
(21:25) Nathan Barry shares his perspective on monetization options for creators.
(25:52) Nathan Barry talks about the current growth and future potential of newsletters.
(29:46) Nathan Barry shares a story about how having an audience can shortcut career paths.
(31:24) Transitioning from personal brand to building a business
(32:22) Using personal brand to drive attention to other businesses
(34:21) Debate on the success of creator-led agencies
(39:15) Strategies for growing Twitter following
(42:09) Repackaging and reposting content for maximum reach
(45:47) Nathan Barry is transparent about his financials to inspire others.
(52:59) Nathan Barry discusses the flywheel strategy for growing a newsletter.
(55:30) Advertising as a loop closer drives new subscribers for sponsorships.
(57:54) Growing the newsletter audience leads to book sales and more opportunities.
(59:59) Building network effects between creators through the Creator Network.
(1:01:36) Convertkit's Creator Network and Spark Loop acquisition.
(1:06:09) Nathan suggests using partnerships with other blogs to promote the subscription service and increase email sign-ups.
(1:07:38) Eric asks Nathan about his quote "making money is a skill" and Nathan explains that building a successful business requires developing a range of skills.
(1:11:37) Nathan shares where people can find him online, including his podcast and newsletter.

—

What should I talk about next? Who should I interview? Please let me know on Twitter or in the comments below.
Did you enjoy this episode? If so, please leave a short review here
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Previous Episode

Making A Million Bucks in 48 Hours? | Noah Kagan

Eric Siu interviews Noah Kagan, the founder of AppSumo, to explore essential entrepreneurial insights. They discuss the significance of having a clear vision, maintaining high standards, and finding joy in the entrepreneurial journey. Noah shares practical strategies for achieving business success, emphasizing the importance of focus, goal setting, and overcoming challenges. Noah's wealth of experiences and practical advice offers valuable insights for aspiring entrepreneurs.

Watch the full interview here: https://youtu.be/Dqccee-F0QA

Don’t forget to help us grow by subscribing and liking on YouTube!

TIME-STAMPED SHOW NOTES:

(00:00) Introduction to Noah Kagan
(02:06) Importance of internal satisfaction rather than external achievements
(06:00) Noah Kagan's approach to hiring elite advisors
(07:20) Example of Mark Zuckerberg having a business coach
(08:12) Noah Kagan's coaching framework and the coaches he has
(14:26) Noah Kagan's approach to reaching out to prefluencers and the importance of engagement
(16:06) Introduction to Noah Kagan's business, Appsumo
(19:06) Noah Kagan's goal for Appsumo's growth
(22:14) Balancing running a business, YouTube channel, and book writing
(37:59) The interest rate environment in 2020 and 2021 has led to founders stepping back into their businesses.
(38:29) Hiring CEOs may be overrated as founders are better at driving the vision.
(40:00) AppSumo's team has been reduced to improve efficiency and profitability.
(46:15) Many businesses fail because they quit too soon before seeing success.
(53:52) Eric Siu and Noah Kagan discuss the inspiration behind their book, "Million Dollar Weekend."
(56:30) Eric asks Noah to explain the 1-minute business model and its impact on AppSumo.
(57:09) Noah emphasizes the importance of targeting a million-dollar market and optimizing the business model.
(01:00:40) Eric Siu mentions sales as a pain point in his business.
(01:04:00) Noah shares his thoughts on lifetime deals and subscriptions.
(01:05:10) Eric asks Noah about finding contentment and fulfillment in life.
(01:09:00) Noah Kagan explains how he approached dating like a business, focusing on who he wanted and where to find them.
(01:15:40) Noah Kagan emphasizes the need to grow a business through social media and monetize the audience.
(01:19:30) Noah Kagan explains different business models for newsletters and how Appsumo monetizes its newsletter.
(01:21:10) Noah Kagan shares his five-part strategy for promoting his book, including building a launch team.
(01:24:00) Noah Kagan discusses the success of hand-to-hand marketing and using surveys to engage customers.
(01:26:15) Noah Kagan explains his goal of selling 25,000 books and his research-based approach to podcast interviews.
(01:27:00) Noah Kagan shares his list of top ten shows to promote his book.
(01:32:14) Noah Kagan emphasizes the importance of making an impact rather than just making a list.
(01:41:52) Jeremy's impact on the YouTube channel's growth
(01:47:15) Investing in the YouTube channel as an audience-building strategy
(01:56:50) Noah Kagan shares the story of Larry Janeski, who built a successful business by never quitting.
(01:58:30) Noah Kagan discusses the structure and budget of his content team
(02:06:00) Balancing sustainability and enjoyment in content creation
(02:09:09) Noah Kagan's website for more information

—

What should I talk about next? Who should I interview? Please let me know on Twitter or in the comments below.
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Connect with Eric ...

Next Episode

How He Cracked the Money Making Secrets of Wordpress | Syed Balkhi

Syed Balkhi and Eric Siu discuss the power of compounding and the importance of maintaining friendships with other high performers. Syed shares his philosophy of giving unconditionally and compounding goodwill, emphasizing the need to avoid the frustration coefficient that can hinder progress. He also shares insights on the power of compounding, the challenges of passing on generational wealth, and the value of learning from historical patterns. This conversation provides valuable lessons and perspectives for both aspiring and experienced investors.

Watch the full interview here: https://youtu.be/O5VhhH0Aky8

Don’t forget to help us grow by subscribing and liking on YouTube!

TIME-STAMPED SHOW NOTES:

(00:00) Syed Balkhi defines himself as a blogger who helps people build better websites using WordPress.
(01:18) Syed Balkhi discusses the concept of running a profitable business every year to achieve a continuous exit.
(04:41) Syed Balkhi explains the value of masterminds and peer groups for personal and professional growth.
(04:58) Syed Balkhi advises teenagers and young adults to start building a network by following people they admire.
(06:03) Syed Balkhi discusses the different benefits he gains from various mastermind groups and forums.
(08:49) Syed Balkhi introduces the concept of the frustration coefficient and warns about its negative impact on decision-making and relationships.
(09:59) Syed Balkhi advises practicing radical candor and addressing frustrations directly to interrupt negative compounding.
(13:29) The power of compounding goodwill and giving unconditionally.
(14:43) Going deep instead of wide in networking and learning.
(19:56) The driving forces of incentives and insecurities in human behavior.
(20:47) Two driving forces shaping human behavior: insecurities and incentives.
(24:59) The importance of empathy and aligning goals with team members.
(26:07) Viewing acquisitions as a more lucrative alternative to paid media.
(30:46) Being known enough to have influence while maintaining anonymity.
(31:05) The story of Syed Balkhi's father working at a gas station.
(33:22) Syed bought gas stations as a backup source of income.
(36:40) Syed's negotiation philosophy: no emotional attachment.
(38:17) Syed emphasizes the importance of staying frugal.
(39:46) Syed Balkhi shares his strategy for offsetting new expenses with investments.
(45:15) Syed Balkhi shares examples of investments he made to solve problems in his own businesses.
(46:31) Eric Siu and Syed Balkhi discuss the potential rise of pay per task pricing models.
(47:28) Syed Balkhi and Eric Siu talk about the adoption window for new technologies.
(48:40) Syed Balkhi advises against overestimating one's ability to turn around businesses.
(52:11) Favorite Mungerisms and Buffettisms.
(58:41) Recommended books: "Psychology of Money," "Atomic Habits," "Same as It Ever Was," "Clear Thinking," and the Thompson trilogy.
(1:00:02) Lessons from the Vanderbilt and Rockefeller families on passing down generational wealth.
(1:02:35) Find more about Syed Balkhi online.

—

What should I talk about next? Who should I interview? Please let me know on Twitter or in the comments below.
Did you enjoy this episode? If so, please leave a short review here
Subscribe to Leveling Up on iTunes
Get the non-iTunes RSS Feed

Connect with Eric Siu: