Founder and CEO of ConvertKit, Nathan Barry, discusses his journey from almost shutting down his business to building a $200 million company. Topics include annual life review ritual, transformative writing habits, flywheels in sales, and the importance of team building for success.
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volunteer_activism ADVICE
Annual Life Review For Memory And Direction
Do make an annual life review that you write for yourself and future family members to capture goals, travel, and projects.
Use photos, calendar data and consistent tracking apps so the review stays accurate and useful over years.
question_answer ANECDOTE
The Shut‑Down Or Double‑Down Moment
Nathan was advised to shut down ConvertKit 18 months in but instead waited and reassessed his commitment and resources.
He set a six-month target to reach $10,000/month or shut it down, then doubled down and ultimately built it into a large company.
volunteer_activism ADVICE
Use Hard Milestones To Decide
Do ask yourself if you've given a project every possible chance to succeed before quitting and quantify a time or revenue limit for a decision.
Use a concrete deadline or milestone (Nathan used $10k/month in six months) to force a decisive outcome.
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How does an entrepreneur go from being told to shut down their business to building a software company worth over $200 million and serving over 50,000 creators? In this episode of How I Work, Nathan Barry, founder and CEO of ConvertKit, shares his incredible journey and the counterintuitive strategies that propelled his success. In this episode, we discuss:
🤔 Nathan's annual life review ritual: We delve into how he not only assesses business opportunities but also tracks his adventures, home life updates, fitness endeavours, and personal goals.
🛑 The turning point: Just 18 months into launching ConvertKit, a friend advised him to shut it down. Discover the pivotal questions Nathan asked himself and the framework he used to make that crucial decision.
💬 Nathan shares his transformative experience of writing 1000 words a day for 600 consecutive days and how this habit has evolved over time.
🌀 What on earth are flywheels? We unravel this concept and discuss how Nathan applied it to the sales process at ConvertKit.
👥 The importance of team building and its ripple effects on business success.
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