In this episode, Ryan McCready, content leader turned Principal Content Engineer at Demostack, opens up about the moments that shaped his path: hacking distribution in the early “monoculture SEO” days, sharpening his voice through roles at Foundation, Reforge, and Whimsical, and facing his first layoff. He shares candid stories about creator burnout after viral teardowns, being the last marketer standing after cuts, and the gut punch of being told he hadn’t delivered on a role that had completely changed. When the market went quiet, Ryan turned the setback into a story on LinkedIn, igniting a thousand DMs, weeks of interviews, and a fresh sense of momentum.

Now, as a builder and editor who treats vulnerability like a career asset, Ryan talks about measuring success in relationships, not just metrics, documenting your receipts, keeping your voice, and sending that DM. He breaks down the unglamorous parts of leadership: giving and receiving hard feedback, guarding against plagiarism, and aligning work with products that actually have staying power, while showing how practical AI and automation can clear the busywork so you can create with intention.

In this conversation, you’ll learn:

• How vulnerability, done thoughtfully, can unlock opportunity, community, and your next role

• Practical ways to productize your “receipts” with AI or automation so your wins market themselves

• How to deliver and absorb tough editorial feedback while protecting quality and your own voice

Things to listen for:

(00:00) Intro

(01:34) Ryan’s early career and content creation journey

(04:19) Navigating career challenges and feedback

(09:37) Thank you to our sponsor, Navattic

(11:04) Giving and receiving feedback

(14:58) On being a team player

(17:41) The importance of adaptability

(31:18) The power of vulnerability in job hunting

(35:39) Creating a strong online presence

(41:57) Difficult conversations in leadership

(51:16) Building professional relationships

A huge thanks to this episode’s sponsor:

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

Resources:

Connect with Ryan:

LinkedIn: https://www.linkedin.com/in/ryan-mccready

Demostack: https://www.demostack.com/

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