Building With Clarity: Lessons in Product Management With Jonathan Tai

Hello everyone! I’m Conrad Ruiz, founder of Well Aware, and today I want to take a moment to reflect on something that feels deeply personal: the intersection of friendship, curiosity, and the discipline of product management.

This is a story about building — not just products, but relationships, frameworks, and trust. And at the heart of it is someone I’m incredibly grateful to call both a friend and collaborator: Jonathan Tai — or as I call him, JT.

We met at WPI years ago, both of us full of ideas and ambition, but it wasn’t until we reconnected later in our professional lives that I got to see just how powerful JT’s mind really is. His ability to distill complexity into clear, actionable steps is something I’ll never stop admiring.

JT’s Journey: From Robotics Engineer to Product Leader

JT’s background is fascinating. He started in robotics — designing intricate systems where precision and adaptability had to coexist. But over time, his curiosity led him to something bigger: product management. Because as complex as machines are, people are infinitely more nuanced.

He took his engineering mindset and applied it to the art of working with humans — building processes that feel intuitive, making sure teams have what they need before they even know to ask. That rare balance between structure and empathy is where JT truly shines.

The Hard Lessons of Product Development

When I first started working on Loop — our platform for task and accountability management — I did what most founders do: I jumped headfirst into building without fully defining the scope. I thought passion would carry me through.

It didn’t.

What I lacked was clarity. I was overwhelmed by possibilities, constantly questioning which features to prioritize, and unsure when to say “not now.”

That’s when JT stepped in.

He didn’t just tell me what to do — he walked me through his process. He asked questions that forced me to slow down:

• What’s the simplest version of this idea that still delivers value?

• What decisions can we defer until we’ve learned more from real users?

• What infrastructure do we need today that won’t become a burden tomorrow?

Those conversations shifted everything for me.

Systems Thinking in Action

JT has this incredible talent for making the abstract concrete. He would take my rambling ideas and return with structured diagrams, detailed workflows, and visual roadmaps that made me go, Oh — now I get it.

It wasn’t just about helping me build Loop; it was about helping me become a better founder. I began to understand that product management isn’t about doing everything — it’s about doing the right things, in the right order, with the right expectations.

He taught me that good systems aren’t restrictive — they’re liberating. They free you up to focus on creativity and growth because the scaffolding is already in place.

The Power of Saying No

One of the hardest lessons I learned — with JT’s guidance — was restraint. The temptation to add “just one more feature” is strong. But JT taught me to be ruthless in protecting the product’s core essence.

He introduced me to the concept of the minimum viable context — just enough information and structure to make meaningful progress without drowning in detail. That idea alone saved me from countless hours of spinning my wheels.

Communication: The Real Secret Weapon

Above all, JT’s greatest gift is how he fosters communication. Product development lives and dies on the strength of conversations — between founder and product manager, between product and engineering, between the business and the end user.

With JT, communication is never just transactional; it’s an ongoing dialogue. He makes space for questions, listens closely, and adapts his approach to fit the person in front of him. That empathy makes teams feel safe — and when people feel safe, they build faster and smarter.

What’s Next

I won’t pretend our work is finished — far from it. Loop is evolving every day. But I feel confident knowing that I have the systems, the mindset, and the support in place to keep building.

And if there’s one thing I’ve learned from JT, it’s this: The best products aren’t built in isolation. They’re the result of thoughtful collaboration and intentional design.

If this story resonates with you — if you’re building something, or dreaming about it, or simply curious how founders and product experts think through messy, complex challenges — I invite you to check out our latest episode of the Well Aware Podcast.

In this episode, I sit down with JT to go deeper. We talk about his career pivot, the frameworks he uses to help founders get unstuck, and the countless lessons we’ve both learned through trial, error, and persistence.

👉 Listen to the episode on Youtube and Libsyn

And if after listening, you feel like you could use a JT in your corner — reach out. I’d be more than happy to make an introduction through Loop, the very product he helped me build.

Until next time, stay curious, be patient, and keep building.