Kevin Goldsmith
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kevingoldsmith.com
Kevin Goldsmith
@kevingoldsmith.com
This is my account for technology leadership posts and announcements. For personal stuff, https://bsky.app/profile/kmg.bsky.social.

Author of "It Depends: Writing on Technology Leadership 2012-2022"

CTO @ DistroKid

https://kevingoldsmith.com
New episode of the It Depends: Lessons in Technology Leadership Podcast - "Leading What You’ve Never Done Before"

Your scope will eventually outrun your resume.
The job isn’t to become an expert in everything; it’s to lead the system around it.

itdependspod.com/episodes/lea...
January 18, 2026 at 4:54 PM
Experience makes the job easier.
That’s also when growth quietly stalls.

This week’s newsletter is about reflection as a leadership skill. Not journaling for journaling’s sake, but deliberate time to avoid running the same playbook forever.

kevingoldsmith.substack.com/p/reflection...
January 11, 2026 at 9:55 PM
New podcast episode for the new year! Why a reflection practice is critical as you move into senior leadership (because no one else is going to be focusing on developing you). You can’t lead others to grow if you’ve stopped growing yourself.

pod.link/1724860326/e...
January 5, 2026 at 12:02 AM
Tech debt isn’t inherently good or bad. It’s information.

Some debt is a smart trade-off
Some is safe to ignore
Some is genuinely dangerous
Some is a warning that leadership systems, not code, need attention

The problem isn’t debt. It’s unexamined debt.

kevingoldsmith.substack.com/p/tech-debt-...
December 14, 2025 at 2:25 PM
Just released a new episode on technical debt.

The truth? Healthy teams take on debt intentionally. The trick is knowing which debt matters and which doesn't.

pod.link/1724860326/e...
December 7, 2025 at 9:25 AM
Board meetings aren’t mysterious—they’re high-stakes performance reviews for the whole company. In this episode, I explain how they work, who’s in the room, and why they shape so many strategic decisions.

itdependspod.com/episodes/dem...
November 23, 2025 at 10:57 PM
A technical strategy isn’t a roadmap; it’s how you align your team to face the future together.

In this episode of It Depends, I discuss what makes a good strategy, how to document it effectively, and how to keep it alive as your company evolves.

pod.link/1724860326/e...
November 9, 2025 at 9:22 AM
new newsletter: Values->Culture->Everything
open.substack.com/pub/kevingol...
October 5, 2025 at 9:10 AM
New article! "You should give that talk or write that blog"

kevingoldsmith.substack.com/p/you-should...
September 8, 2025 at 4:35 AM
New "It Depends" episode: Final Q&A before summer break.

Tackling the messy realities of tech leadership:
Competitive reviews vs collaboration culture
Innovation without roadmap chaos
Accessibility advocacy as an IC

Real problems, practical solutions. No fluff.
pod.link/1724860326

#TechLeadership
June 8, 2025 at 9:31 AM
New Q&A episode of It Depends: Lessons in Technology Leadership is live! 🎧

Tackled six listener questions covering everything from building a learning culture on a shoestring budget to the hard realities of organizational change.

pod.link/1724860326
May 25, 2025 at 9:07 AM
New episode of the It Depends podcast: I answer your questions on accountability in matrix organizations, making the qualitative quantitative in reviews, growing from a data leader to be a CTO, and protecting your team from layoffs.

pod.link/1724860326
May 11, 2025 at 9:57 AM
What happens when your company outgrows its leadership? In the latest It Depends episode, I share lessons on succession, growth, and knowing when it’s time for change.

Listen here: pod.link/1724860326
April 27, 2025 at 8:51 AM