Commit & Push

"Don’t hire the brilliant jerk." That’s just one of the hard truths Zach Goldberg, CTO of Gruntwork and author of The Startup CTO’s Handbook, drops in this episode of Commit & Push.

Zach joins Damien to talk about the mistakes most new CTOs make, why developer productivity is wildly misunderstood, and how overcomplicating your stack can tank your team. They dig into what actually works when scaling a dev org, how to build real performance systems, and why most software out there… just isn’t very good.

If you're leading engineers—or thinking about how to lead better—this episode is your shortcut to avoiding expensive management lessons and building a team that actually ships.

If you enjoyed this episode, make sure to subscribe, rate and review on Apple Podcasts, Spotify and YouTube Podcasts, instructions on how to do this are here.

Episode Highlights:

• [0:00] Intro
• [1:03] Zach’s Journey to Becoming a Startup CTO
• [3:15] What is Gruntwork?
• [5:57] Balancing a Full-Time CTO Role with Coaching
• [6:50] Writing The Startup CTO’s Handbook
• [11:40] Lessons in Management and Hiring
• [16:22] Setting Goals &  Metrics for Engineers
• [22:22] Full-Time vs. Fractional CTOs
• [28:12] Keeping Software Development Simple
• [30:51] Developer Productivity
• [34:50] Overhyped and Underrated Tech
• [44:43] Will AI Replace Developers?
• [49:38] Why Every CTO Should Consider Coaching
• [51:25] Where Can You Find Zach Online?

Episode Resources:

• Zach Goldberg’s Website
• Zach Goldberg on LinkedIn
• Gruntwork Website
• The Startup CTO’s Handbook
• Damien Filiatrault on LinkedIn
• Scalable Path Website

Most AI projects fail. Some never ship. Others ship and implode. So what’s going wrong?

In this episode of Commit & Push, Damien sits down with Dan Saffer - Associate Director of Outreach at Carnegie Mellon’s Human-Computer Interaction Institute and author of Microinteractions - to dig into the real reasons so many AI projects fall apart.

Drawing on years of academic research and hands-on industry experience, Dan unpacks the five most common failure points: bad data, fragile models, vague value props, ethical landmines, and poor user adoption. They also dive into the myth of explainability, the broken state of AI UX, and why “sparkle-washing” products with AI features often makes things worse, not better.

Oh - and if you’ve noticed your favorite platforms slowly turning into garbage fire content mills? Dan’s got a name for that too: enshittification - and AI might be pouring gas on it.

Whether you're building AI tools, integrating them into your product, or just trying to separate signal from noise, this episode pulls back the curtain on what’s real, what’s hype, and what to do about it.

If you enjoyed this episode, make sure to subscribe, rate and review on Apple Podcasts, Spotify and YouTube, instructions on how to do this are here.

Episode Highlights:

• [00:00] Intro
• [02:00] Who Is Dan Saffer?
• [04:53] Why So Many AI Projects Fail
• [11:02] Why “Perfect” Use Cases Are a Trap
• [14:39] Trusting the AI Too Much
• [20:44] The Rise and Fall of Chat Interfaces
• [35:31] Enshittification: AI’s Role in Ruining Platforms
• [42:49] Stop Slapping Sparkles on Everything
• [44:52] AI Tools That Delight

Episode Resources:

• Dan Saffer’s LinkedIn
• CMU Human-Computer Interaction Institute Website
• Microinteractions Books
• Damien Filiatrault on LinkedIn
• Scalable Path Website

Welcome to Commit & Push, where we talk about how great software really gets built. I'm Damian Filiatro, your host and founder of Scalable Path. Each episode, we'll explore the decisions, tradeoffs, and strategies that shape successful digital products. You'll hear from developers, founders, and tech leaders about the challenges they've faced, the solutions they've found, and the insights they've gained. Ready to explore what makes digital products thrive? Let's get into it.