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
Author of "It Depends: Writing on Technology Leadership 2012-2022"
CTO @ DistroKid
https://kevingoldsmith.com
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-...
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
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-...
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-...
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...
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
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...
The truth? Healthy teams take on debt intentionally. The trick is knowing which debt matters and which doesn't.
pod.link/1724860326/e...
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...
itdependspod.com/episodes/dem...
November 23, 2025 at 10:57 PM
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...
itdependspod.com/episodes/dem...
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...
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
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...
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...
Every wave of tech promises transformation. Few deliver.
My latest newsletter, "Making Technology Choices That Last," is about leading with intent instead of impulse.
open.substack.com/pub/kevingol...
My latest newsletter, "Making Technology Choices That Last," is about leading with intent instead of impulse.
open.substack.com/pub/kevingol...
November 2, 2025 at 3:54 PM
Every wave of tech promises transformation. Few deliver.
My latest newsletter, "Making Technology Choices That Last," is about leading with intent instead of impulse.
open.substack.com/pub/kevingol...
My latest newsletter, "Making Technology Choices That Last," is about leading with intent instead of impulse.
open.substack.com/pub/kevingol...
New newsletter: The Hidden Architecture of Engineering kevingoldsmith.substack.com/p/the-hidden...
October 20, 2025 at 4:46 PM
New newsletter: The Hidden Architecture of Engineering kevingoldsmith.substack.com/p/the-hidden...
So used to seeing Meri Williams as a conference host, I forgot how good a speaker Meri is! #LeadDevNYC
October 16, 2025 at 6:39 PM
So used to seeing Meri Williams as a conference host, I forgot how good a speaker Meri is! #LeadDevNYC
Kudos to Pooja Varshneya for the prettiest slides so far. #LeadDevNYC
October 15, 2025 at 7:28 PM
Kudos to Pooja Varshneya for the prettiest slides so far. #LeadDevNYC
Really liked the talk from @addyosmani.bsky.social on leadership supporting AI coding. #LeadDevNYC
October 15, 2025 at 4:05 PM
Really liked the talk from @addyosmani.bsky.social on leadership supporting AI coding. #LeadDevNYC
Hello #LeadDevNYC! @yee.camp starting things off!
October 15, 2025 at 1:48 PM
Hello #LeadDevNYC! @yee.camp starting things off!
new newsletter: Values->Culture->Everything
open.substack.com/pub/kevingol...
open.substack.com/pub/kevingol...
October 5, 2025 at 9:10 AM
new newsletter: Values->Culture->Everything
open.substack.com/pub/kevingol...
open.substack.com/pub/kevingol...
New newsletter! kevingoldsmith.substack.com/p/making-the...
September 22, 2025 at 12:15 AM
New newsletter! kevingoldsmith.substack.com/p/making-the...
New article! "You should give that talk or write that blog"
kevingoldsmith.substack.com/p/you-should...
kevingoldsmith.substack.com/p/you-should...
September 8, 2025 at 4:35 AM
New article! "You should give that talk or write that blog"
kevingoldsmith.substack.com/p/you-should...
kevingoldsmith.substack.com/p/you-should...
Getting ready for my keynote tomorrow at Seattle's Got Tech...
July 28, 2025 at 7:20 PM
Getting ready for my keynote tomorrow at Seattle's Got Tech...
New newsletter post: The story behind publishing "It Depends"
All the details - tools that worked, costly mistakes, actual profit margins, and why I went DIY instead of traditional publishing.
A case study in building a creative business while managing risks.
open.substack.com/pub/kevingol...
All the details - tools that worked, costly mistakes, actual profit margins, and why I went DIY instead of traditional publishing.
A case study in building a creative business while managing risks.
open.substack.com/pub/kevingol...
June 29, 2025 at 7:38 AM
New newsletter post: The story behind publishing "It Depends"
All the details - tools that worked, costly mistakes, actual profit margins, and why I went DIY instead of traditional publishing.
A case study in building a creative business while managing risks.
open.substack.com/pub/kevingol...
All the details - tools that worked, costly mistakes, actual profit margins, and why I went DIY instead of traditional publishing.
A case study in building a creative business while managing risks.
open.substack.com/pub/kevingol...
The latest newsletter tackles performance reviews, guild structures, and prioritizing accessibility when you're not in charge.
open.substack.com/pub/kevingol...
open.substack.com/pub/kevingol...
June 15, 2025 at 1:09 PM
The latest newsletter tackles performance reviews, guild structures, and prioritizing accessibility when you're not in charge.
open.substack.com/pub/kevingol...
open.substack.com/pub/kevingol...
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
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 "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
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
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
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 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
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
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
pod.link/1724860326
May 11, 2025 at 9:57 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
pod.link/1724860326
May 4, 2025 at 7:59 PM
New newsletter issue, "Succession for Scale"
kevingoldsmith.substack.com/p/succession...
kevingoldsmith.substack.com/p/succession...
May 4, 2025 at 7:48 AM
New newsletter issue, "Succession for Scale"
kevingoldsmith.substack.com/p/succession...
kevingoldsmith.substack.com/p/succession...
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
Listen here: pod.link/1724860326
April 27, 2025 at 8:51 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
Listen here: pod.link/1724860326
April 20, 2025 at 7:36 AM
In the latest episode of the "It Depends" #podcast, @kstewart.bsky.social and I discuss why big companies often step on their toes when trying to innovate like startups.
#Innovation #startup
pod.link/1724860326
#Innovation #startup
pod.link/1724860326
April 17, 2025 at 6:50 PM
In the latest episode of the "It Depends" #podcast, @kstewart.bsky.social and I discuss why big companies often step on their toes when trying to innovate like startups.
#Innovation #startup
pod.link/1724860326
#Innovation #startup
pod.link/1724860326
📚 New newsletter alert! Two chapters from "It Depends":
* 20 questions to elevate your 1:1s
* My OPEX Week speech on autonomy culture & Agile meets Operational Excellence
kevingoldsmith.substack.com/p/twenty-que...
#Management
* 20 questions to elevate your 1:1s
* My OPEX Week speech on autonomy culture & Agile meets Operational Excellence
kevingoldsmith.substack.com/p/twenty-que...
#Management
April 6, 2025 at 8:04 AM
📚 New newsletter alert! Two chapters from "It Depends":
* 20 questions to elevate your 1:1s
* My OPEX Week speech on autonomy culture & Agile meets Operational Excellence
kevingoldsmith.substack.com/p/twenty-que...
#Management
* 20 questions to elevate your 1:1s
* My OPEX Week speech on autonomy culture & Agile meets Operational Excellence
kevingoldsmith.substack.com/p/twenty-que...
#Management