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

The Nathan Barry Show

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 Introduction
01:00 Why Barrett Left ConvertKit
05:26 Lessons Learned and Strategic Insights
13:45 Performance Management
15:39 Feedback Culture and Team Dynamics
33:08 Trust and Agency in Leadership
47:26 Compensation and Benefits Structure
58:24 Leveraging Influential Creators for Brand Growth
01:14:14 Reflecting on Leadership and Team Dynamics
01:26:27 Personal Branding and Content Creation
01:34:05 Closing Thoughts

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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/nathanbarry
Website: 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/dnp561Z

Highlights:
04:37 Nathan on the importance of “taking your seat as the leader.”
06:43 How to build confidence, learning as you grow
08:00 Nathan and Barrett should’ve made faster decisions
13:48 The median performance you tolerate becomes the expectation
15:39 Polarity as counteracting forces that work together
18:02 Companies outgrowing employees
31:31 Toxic feedback triangles
33:08 Trust adults to be adults (allow employees to act in their agency)
35:38 Building strong relationships by listening
40:56 Unsolicited feedback
47:26 Pros and cons of different compensation and incentive strategies at ConvertKit
01:00:14 Nike sponsored athletes model
01:08:50 Barrett’s advice for ConvertKit: “be the advocates for your own story.”
01:14:40 Reboot’s 4 questions for dealing with conflict