Dogged Pursuits Ep. 1 Highlight Reels vs. Real Work

You're Already Using AI.
So Why Are You Working More, Not Less?

You've watched the tutorials. You've tried the tools. You're putting in extra hours to keep up — and you still don't have one thing that actually saves you time. That's what I fix.

Trusted by

Imagine…

…your boss stops asking you to learn the latest AI fad — because they already know you're on top of it.
…people in your next team meeting look to you when they need to know what AI can do for the current project.
…the next time AI comes up, you point to something real you built — not the latest headline from ChatGPT.
Background
10+ Years in Software & Teaching
Instructor Rating
4.9 / 5.0
Workshop Focus
Non-Coders Welcome
Support
Pre-Work · Build Day · Follow-Up

Hi, I'm Jai

I've Been Where You Are

I spent the last ten years in New York City as a software engineer and teacher — shipping production software at HashiCorp, building curriculum from scratch, and consistently earning a 4.9 instructor rating across every class I've ever taught.

But the reason I started Chai With Jai isn't on my résumé.

I watched smart, capable people — friends, colleagues, clients — get left behind by AI. Not because they weren't sharp enough. Because nobody gave them a practical first step. Everyone was selling the category. Nobody was helping with the work.

Now I do one thing: I help non-coders get their first real AI win.

Watch 0:05
Start here

The short version of the promise

A quick intro for people deciding whether Chai With Jai is practical enough for the work they actually do.

Watch clip
Original show

Dogged Pursuits

A first look at the media side of the work: honest conversations about ambition, execution, and what happens behind the highlight reel.

Why this works

Technical direction plus a learning system.

Most people do not need another tool demo.

They need a translation layer: what to build first, how to judge whether it works, and how to keep using it after the workshop energy wears off.

My edge is the combination.

I bring production engineering, teaching, and instructional design into one coaching loop.

  • Software Engineer at HashiCorp (Nomad) Product-quality thinking under real delivery pressure.
  • Taught JavaScript at Parsons Coaching built for how adults actually learn.
  • Frontend + UX translator Technical complexity turned into usable workflows.

What I Keep Hearing

The Same Three Things

I know I should be using AI more. I just don't know where to start.
I'm being asked to do more with less, and AI is framed as the answer — but nobody's showing me how.
I've opened ChatGPT a dozen times and still don't have one workflow I actually trust.

The problem isn't intelligence. It's support.

Most AI education starts in the wrong place — models, frameworks, prompt patterns, browser extensions. None of it answers the question a working person actually needs answered:

What should I build first that will make next week easier?

The Shift

That Question Changed Everything

AI education for working people can't start with the tools. It has to start with one real work problem.

Not the impressive one. The useful one.

The one that already costs you time every week — messy meeting follow-ups, content trapped in a long draft, proposals rebuilt from scratch, customer research that never turns into usable insight.

Start there, and AI stops feeling abstract. It starts feeling like something you can actually use.

One recurring problem. One practical build. One real win you can point to.

My Approach

No Hype. No Theory. Just Building.

I don't teach 19 prompt patterns. I don't sell AI at an altitude that makes normal people feel behind.

  • Pick the right first build — not the one that sounds smart, the one that saves you real time
  • Build it with guided support — pre-work before, hands-on help during, follow-up after
  • Leave with something real — something that works, that you built, and that you'll keep using

The goal isn't to leave impressed by AI. It's to leave with something you can actually use on Monday morning.

Outcome 01

Signal

You learn how to separate hype from useful implementation choices.

Outcome 02

Systems

You build repeatable workflows you can run weekly, not random experiments.

Outcome 03

Shipping

You move from "I should learn this someday" to using AI in active projects.

What Students Say

After the Fear Drops

"Your class took away my fears and doubts that AI was unattainable. This class really changed my mindset. I feel empowered."

— Toya, workshop graduate

"You don't know what you don't know until someone comes along and teaches you what the possibilities are. I can't thank Jai enough for opening my eyes to what's possible with AI."

— Samina Quraishi

Students don't just leave feeling better. They leave clearer on what AI can do for their work — and with something concrete to show for it.

From 2.5 years of nothing to a first successful event.

"Three months later, I threw my first successful event. The focus did not just help me find my One Thing - it helped me understand why I kept losing momentum."
Nick Stebenne, Founder, Marketito

From 4-hour nightly planning to less guilt.

"I used to spend 4 hours every night planning my day and catching up on tasks, only to watch it all fall apart by lunchtime the next day."
Anne Flanagan, Consultant

From scared of AI to having a thinking partner.

"The day Jai showed me how to think with AI instead of just using AI tools, everything clicked."
Seema Kothari, Real Estate

What to expect

A practical system you can keep using.

The experience is designed around one useful build, then the operating rhythm that helps it survive after the session ends.

Step 01

Guided onboarding

We narrow the problem, define the first useful workflow, and set expectations before build time starts.

Step 02

Build day

You make something concrete with support, templates, prompts, and judgment calls explained in plain language.

Step 03

Follow-up loop

You leave with next steps, reusable artifacts, and a clearer way to evaluate future AI work.

Ready to Build Your First Useful Thing With AI?

You don't need to code. You don't need the perfect idea. You just need one real problem and a willingness to try.