$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