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

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May 30, 2024

Barrett Brooks, former COO at ConvertKit, joins for a candid chat on leadership nuances, strategic decision-making, team dynamics, compensation strategies, and leveraging creators for brand growth. They reflect on lessons learned, company culture, and personal branding. Insights on transparency, feedback culture, and creating connections in business.

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ANECDOTE

Emotional CEO Departure Walk

Nathan Barry told Barrett Brooks he was leaving ConvertKit during a sunset walk on a team retreat.
Both were emotional, and the team was informed the next day, causing significant trauma.

ADVICE

Take Your Seat as Leader

Embrace your role as CEO and make decisions confidently without trying to please everyone.
Clear decisiveness stabilizes the team and establishes strong leadership.

INSIGHT

Question Tradition, Innovate Culture

Some company processes persist without reason, and leadership should challenge them.
Testing new ideas on culture and performance can reveal better ways to operate.

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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:
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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