"Back in the 1900s when I was crossing the Great Plains in a covered wagon, programming in the back, the cover headline was: Software Development is Dead."

I talked with Anthony Jackson, a CTO with 30 years across healthcare tech and enterprise software and author of the Architecture Protocol series, on Startup Hustle this week. Anthony is the creator of LeadershipOS, a framework for building teams that keep running when the leader isn't in the room.

Here's what you'll get out of it:

⚡ Why "software development is dead" has been a headline for 30+ years, and why the human judgment layer never goes away

⚡ Why the real gap isn't more engineers, it's product people (and engineers who think like them)

⚡ What actually changes when you go from individual contributor to manager, and why almost no company trains you for it

⚡ Why every line of code still needs a name attached to it, especially in regulated industries

⚡ How "lossy compression" quietly ruins decisions as they filter up and back down through management

⏱️ Episode Breakdown

00:32 Introduction and Anthony Jackson's background

02:13 Is software development dead again?

03:14 The impact of AI on coding and human judgment

04:07 The importance of responsibility in software development

05:59 The challenge of product management and customer feedback

10:18 Transitioning from individual contributor to manager

11:36 Building effective teams and leadership culture

14:41 Anthony Jackson's leadership OS book and approach

18:26 The significance of company and team culture

21:07 The impact of good and bad managers

21:38 Anthony Jackson's newsletter and coaching

23:14 Connecting software developers with customers

25:06 Empathy for users and understanding their experience

28:18 Where to find Anthony Jackson's resources and books

Links & Resources

Connect with Anthony Jackson on LinkedIn

Anthony Jackson's Website - https://technicaleader.coach

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