The #1 Trap Ambitious Startup Leaders Fall Into (From Gong & Clari’s Former Content Lead) (Devin Reed)

In this episode, Devin Reed, one of the leading voices in content and marketing, opens up about the defining moments that shaped his career—from growing up between two very different cultures in Sacramento to building a name for himself at Eventbrite, Gong, and Clari before stepping out on his own. He shares candid stories of career pivots, from giving up on his dream of teaching to unexpectedly landing in tech sales, and later realizing his sweet spot in content marketing. Devin reflects on the sting of being graded a “seven” at a company that recruited him aggressively, the intimidation of being told he wasn’t qualified for his role at just 25, and the burnout he faced after tying too much of his worth to productivity.

Now as a founder, creator, and dad, he talks about learning to measure success not in metrics but in moments—balancing ambition with presence, and re-wiring what it means to “win” in both business and life.

In this conversation, you’ll learn:

- Why it’s essential to question feedback and define your own worth

- How to recognize poor leadership and build a healthier leadership style

- What it takes to reset old wiring around ambition and success

Things to listen for:

(00:00) Intro

(01:59) Devin's upbringing and early career

(02:47) Transition to marketing and entrepreneurship

(03:01) Facing challenges and finding success

(06:33) Pivotal career moments

(08:08) Thank you to our sponsor, Navattic

(11:33) Navigating tough feedback

(17:17) The impact of therapy and self-worth

(21:28) Dealing with imposter syndrome

(26:46) Realizing the importance of empathy in leadership

(28:40) Learning from coaches and mentors

(34:48) Balancing work and personal life

(38:50) Implementing new habits and boundaries

(46:20) Setting goals for fulfillment and happiness

(49:25) Caution in advice and embracing relatability

A huge thanks to this episode’s sponsor:

Navattic: Interactive Product Demo Software - https://navattic.com/value

Resources:

Connect with Devin:

LinkedIn: https://www.linkedin.com/in/devinreed/

The Reeder (official website): https://www.thereeder.co

Reed Between The Lines (podcast): https://www.thereeder.co/content-hub/podcast

Connect with Andrew:

LinkedIn: https://www.linkedin.com/in/andrewcapland/

Substack: https://media.deliveringvalue.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching

Join Growth OS: https://deliveringvalue.co/growth-operating-system