Nathan Barry: Everything We Learned Growing ConvertKit to $40M (and What We'd Do Differently)

Nathan Barry is the Founder and CEO of ConvertKit. In previous careers, Nathan has been a designer, author, and blogger. After learning the power of email marketing, he gave up a successful blogging career to go all-in on ConvertKit. Outside of work, Nathan spends his time playing soccer, woodworking, and chasing after his three boys.

This week, Barrett and Nathan sit down for a candid conversation about the ups and downs of building a $40M company, and what they wish they had done differently. They also dive into their strategies for growing personal brands, the power of clear roles and communication in projects, building strong team relationships, creating a supportive yet high-performance company culture, and much more.

In this episode:

[00:00] - Intro
[04:20] - Why Barrett left ConvertKit
[15:18] - Building confidence as a leader
[22:59] - "We should have fired more people"
[37:57] - Creating a healthy feedback culture
[44:13] - Strategies for better communication
[58:14] - Designing comp and benefits
[01:07:46] - What we nailed on the growth side (and what we could have done differently)
[01:23:10] - Lessons learned from Barrett's departure
[01:36:20] - Podcasting for the long haul
[01:52:16] - On brand differentiation
[01:55:52] - Who Nathan is becoming

Key Takeaways

Clear roles and responsibilities in projects reduces tension and leads to smoother execution.
Relationship-building practices, like listening walks and unsolicited feedback, create strong, trusting relationships within a team.
Written feedback leads to clarity and accountability, helping bridge the gap between intended and received messages.
Growing companies are built on decisive and confident leadership.
Balancing a supportive culture with high performance requires intentional practices and constant recalibration.

Quotes

“I think I tried way too hard to be liked, to make people feel heard, to make sure I wasn't a burden on other people and all of these things. And the person that I'm actually working on becoming is someone who is much more confident, collected, and steady, and just trusting my instinct, and also being relentless in bringing that to life.” ~ Nathan Barry

“We struggled to find the balance between building a culture where everyone felt safe and heard and cared for and building a high-performance culture. We created a lot of strife between us and the team because we, on one hand, would be really emphasizing the softer sides, and then, more quietly between us, we're like, but we're here to win, and we want people who are here to win.” ~ Nathan Barry

“There's not an industry-standard way of doing it. Take the information in front of you and make your decision.” ~ Nathan Barry

Links