From Product Leader to Creator: The Journey I’ve Never Shared Until Now

Most people who follow me know me as someone who writes about AI, growth, and product. Over 250,000 of you have followed my work online.

But here’s something surprising: I’ve never properly introduced myself.

Not the resume version. The real version.

Until now.

Roots, Names, and a Place Called Kalamazoo

My name is Aakash. I was born and raised in Kalamazoo, Michigan. Yes, it’s a real place.

We have something called the “Air Zoo” — a wildly underrated aviation museum with actual military planes and immersive exhibits. It’s a spot I’ve loved since childhood, and now it’s a favorite for my kids too.

Speaking of names, let me settle this once and for all. It’s pronounced “ah-kaash,” not “uh-kosh.” And the last name is “Gup-tha,” not “Goopta.”

(I’ve heard it all. If you just tried pronouncing it, thanks for making the effort.)

I’m a Dad First. Creator Second.

I have two little ones, ages one and three. They are my world.

I wrote part of this article while sitting at the Trevi Fountain in Rome, during their nap. Two weeks ago, we were rock-hopping on the beaches of Rhodes, Greece. And none of it would have been possible in my previous life.

A few years ago, I was working 60-hour weeks as a product leader. My calendar was always full. My passport rarely was.

Now, I work for myself. I travel. I create. And I’m home for bedtime.

Two years ago, I was earning a solid mid six-figure salary. Today, I make double that as a full-time creator. I run two businesses — a newsletter with over 170,000 subscribers and a podcast that has been sold out with advertisers since launch.

But it didn’t start this way.

From PM to VP to… Something Entirely Different

I’ve spent 16 years in product management. Started in SaaS, climbed my way to VP of Product, and then something shifted.

It wasn’t burnout. It was clarity.

I realized I didn’t want to build someone else’s vision anymore. I wanted to build my own.

So I left. Started small. Grew slowly. Learned the ins and outs of audience-building, monetization, and digital storytelling.

Today, I lead a lean team of five. Our profits grew 225% year over year. But more than the numbers, it’s the life that changed.

As Naval Ravikant once said:

Play long-term games with long-term people.

I stopped playing short-term games. And it’s changed everything.

A Few Things You Probably Didn’t Know About Me

• I used to be a policy debater. That’s why I talk fast.
• I’ve rock climbed on five continents. Still chasing the sixth.
• My favorite food is Jamon Iberico. Least favorite? Sugary candy.
• My most treasured life moment was marrying my wife.

And perhaps the most valuable skill I’ve honed over the years isn’t technical at all. It’s energy. Relentless, consistent energy. I never get tired of working or parenting. That engine keeps me moving forward.

As Angela Duckworth puts it:

Enthusiasm is common. Endurance is rare.

I Never Thought I’d Leave Corporate. Then I Did.

For most of my career, I thought I’d be corporate for life. There’s stability. Prestige. Structure.

But over time, I started asking harder questions.

What if success wasn’t just title and compensation?

What if success meant spending a month abroad with your kids?

What if it looked like working less, living more, and still growing faster?

And what if you could do all that while impacting tens of thousands of people every week?

That’s the version of success I’ve found on the other side.

As Steve Jobs once said:

You can’t connect the dots looking forward. You can only connect them looking backward.

Looking back, the dots make sense now.

So, Who Am I Really?

A product thinker. A father. A storyteller. A climber of rocks and businesses.

And mostly, someone trying to live with purpose, joy, and full presence.

My life mission is simple: to have as much fun as possible while impacting as many people as possible.

If you’ve learned something new about me today, I’d love to hear what surprised you.

And if you’re standing at a crossroads in your own career, ask yourself: What kind of life are you optimizing for?

Because sometimes, the biggest breakthroughs come when you stop climbing the ladder — and start building your own.