From H-1B Constraints to Creative Freedom: Learning to Build Within the Rules!

How I learned to explore entrepreneurship as an immigrant engineer in the U.S. and why the dream doesn’t have to wait.

Hi, I’m Harshdeep Gupta.

In 2018, I graduated from IIT Delhi with big dreams and a suitcase full of excitement. My first job offer came from Microsoft Redmond, and before I knew it, I was on a flight to the U.S. ready to start my career, explore a new world, and live the dream I had worked so hard for.

The first few years felt incredible. The campus, the projects, the opportunities everything was larger than life. I felt grateful to be here so early in my career. But beneath all that excitement, there was something I didn’t fully understand back then: the quiet constraints of the H-1B visa.

I had always dreamed of building something of my own an idea that would come alive, end-to-end. But when I started exploring what that would mean in reality, I quickly ran into the legal walls that come with being on a work visa.

I talked to friends brilliant engineers, all on H-1Bs like me. Almost everyone said the same thing:

“Don’t do it. It’s risky. You could lose your status.”

So, I quietly accepted it. I focused on gratitude on how lucky I was to be here, to learn, to grow, to contribute. But deep down, I couldn’t shake the thought that these were golden handcuffs comfortable, shiny, yet still handcuffs.

One night while browsing online, I stumbled upon a community called H1B Founders. The name stopped me mid-scroll. I dug deeper and discovered that this was a group of immigrants just like me people who had chosen not to give up on their entrepreneurial calling. They were figuring out how to build within the rules instead of being paralyzed by them.

After speaking with Sid, the community’s founder, something shifted. For the first time, I realized that entrepreneurship on an H-1B wasn’t a dead end it was a puzzle waiting to be solved.

That clarity reignited something in me.

Since then, I’ve been exploring ways to combine my technical background with creative problem-solving. One idea that came from personal experience is called PicPickr a project inspired by the chaos of sorting thousands of wedding photos. It’s not a company yet, just an experiment I’m learning from a sandbox where I get to think, design, and imagine what could be possible one day.

Along the way, I’ve met other builders who are walking the same tightrope balancing their visa, career, and startup dreams. There’s comfort in that shared experience, and power in the community that understands what you’re going through.

If you’re an immigrant with an entrepreneurial spark inside you, don’t let it die quietly.

Join H1B Founders - 1,400+ immigrants building together. Ask questions. Learn the rules. Build within them.

And if you’re working on something exciting or just thinking about starting reach out. I’m always happy to connect, brainstorm, or even team up.

You can DM me on LinkedIn I’m actively looking for co-founders and collaborators who share this dream.

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BIO: Harshdeep Gupta is a Microsoft engineer, IIT Delhi ‘18, and WIN CLUB member building PicPickr while navigating H-1B. He discovered H1Founders when looking for others who refused to let visa status kill their entrepreneurial spark.

PS: The golden handcuffs are real. But they’re still just handcuffs. You can build within the constraints or let the constraints build your prison. I chose building.