$3M to $40M: An Unfiltered Conversation with My Ex COO | 031

In this episode, Nathan is joined by Barrett Brooks, his former Chief Operating Officer at ConvertKit, for a candid discussion on why Barrett left the company.They explore the nuances of co-leadership, celebrate their biggest achievements, and reflect on lessons learned and what they wish they had done differently.Join us for in-depth learnings on strategic decision-making, compensation strategies, and the company culture at ConvertKit.Timestamps:00:00 Introduction01:00 Why Barrett Left ConvertKit05:26 Lessons Learned and Strategic Insights13:45 Performance Management15:39 Feedback Culture and Team Dynamics33:08 Trust and Agency in Leadership47:26 Compensation and Benefits Structure58:24 Leveraging Influential Creators for Brand Growth01:14:14 Reflecting on Leadership and Team Dynamics01:26:27 Personal Branding and Content Creation01:34:05 Closing ThoughtsIf you enjoyed this episode, please like and subscribe, share it with your friends, and leave us a review. We read every single one.Learn more about The Nathan Barry Show: https://nathanbarry.com/show Follow Nathan:Instagram: https://www.instagram.com/nathanbarry/LinkedIn: https://www.linkedin.com/in/nathanbarry/Twitter: https://twitter.com/nathanbarryWebsite: https://nathanbarry.com/Follow Barrett:Instagram: https://www.instagram.com/barrettabrooks/LinkedIn: https://www.linkedin.com/in/barrettabrooks/Twitter: https://x.com/barrettabrooks/Website: https://barrettbrooks.com/Featured in this episode:ConvertKit: https://convertkit.com/TravelCon: https://travelcon.org/Pat Flynn: https://patflynn.com/World Domination Summit: https://worlddominationsummit.com/Trust Me, I’m Lying: https://a.co/d/dnp561ZHighlights:04:37 Nathan on the importance of “taking your seat as the leader.”06:43 How to build confidence, learning as you grow08:00 Nathan and Barrett should’ve made faster decisions13:48 The median performance you tolerate becomes the expectation15:39 Polarity as counteracting forces that work together18:02 Companies outgrowing employees31:31 Toxic feedback triangles33:08 Trust adults to be adults (allow employees to act in their agency)35:38 Building strong relationships by listening40:56 Unsolicited feedback47:26 Pros and cons of different compensation and incentive strategies at ConvertKit01:00:14 Nike sponsored athletes model01:08:50 Barrett’s advice for ConvertKit: “be the advocates for your own story.”01:14:40 Reboot’s 4 questions for dealing with conflict

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As the CEO of Kit, Nathan Barry has a front row seat to what’s working in the most successful creator businesses. On The Nathan Barry Show, he interviews top creators and dives into the inner workings of their businesses in his live coaching sessions. You get unique insight into how creator businesses work and what you can do to increase results in your own business. One of the things Nathan is passionate about is helping you create leverage. Creator Flywheels let you create many copies of yourself so you don’t get bogged down with the little things in your business. Flywheels will help you reach a place where you can focus on revenue instead of busywork. Tune in weekly for new episodes with ideas and tips for growing your business. You’ll hear discussions around building an audience, earning a living as a creator, and Nathan’s insights on scaling a software company to $100M. Learn how to get more results with less effort and: Grow faster over time. Work less hard over time. Make more money over time.