April didn’t just move fast, it rewrote how software gets built.
AI is no longer just assisting, it’s starting to own the work. From generating production-ready code to completing complex engineering tasks in minutes, we’re watching developers shift from writing every line to reviewing, guiding, and orchestrating.
At the same time, enterprises aren’t experimenting anymore, they’re deploying AI deep into real workflows. New models are pushing what’s possible across design, coding, and even cybersecurity. This isn’t incremental progress. It’s a turning point, from AI-assisted tools to fully AI-driven systems.
In this month’s conversations, we’re unpacking what that shift really means, and where it’s all heading next.
As always, listen to the latest episodes on Spotify or Apple, or watch them on YouTube.
The Advantages of Serving
the Little Guys
Andrew Stern is the CEO of Quilt Software, and no, it has nothing to do with fabric. We unpack how to deliver real value without overbuilding, why actionable intelligence beats more data, and the growing risk of scaling AI without understanding the costs.
BONUS CONTENT
I asked Andrew about a business decision that paid off but wasn’t obvious at the time, and he shared how Quilt made an early, seemingly excessive investment in data systems, what they called “a big hat on a little guy,” to avoid past mistakes.
His takeaway: they didn’t anticipate AI, but that decision became a massive advantage, positioning them to adopt AI faster than most, and proving it’s hard to go wrong betting on data.
Harsha Chintalapani, Co-Founder & CTO of Collate, shares
how he tackled complex data challenges at Uber, and what it really takes to turn data into something that drives decisions, not just dashboards.
We also get into the harder problems most teams ignore, adding real meaning at the metadata level, why open source attracts top talent, and his concern that in a world of AI-generated code, developers don’t lose the ability to truly model systems.
BONUS CONTENT
I asked what business decision had a surprisingly positive impact, and Harsha shared that going fully remote, out of necessity during COVID, ended up working far better than he expected.
His takeaway: by hiring the right leaders and people who truly believed in the mission, the team thrived without being in the same room, proving his initial doubts about remote work were unfounded.
Books Behind the Leaders: Recommendations from our Guests
I always ask our guests to recommend a book, or perhaps a blog or podcast, that has been helpful in their lives—professionally or personally. Here’s what our recent guests have recommended.
The Fortune at the Bottom of the Pyramid: Stern shares how this book has had a big influence on how he thinks about markets. While living in India and focused on serving rural communities, this book reframed what looked like small, low-income customers into a massive opportunity when viewed at scale.