Chapter 1: Freedom

I got my green card in December 2022. It was a day I’d waited for over two and a half years, but in reality, I’d been waiting much longer. Since 2016, I had to strategically time my job choices and optimize for places with good visa options and stability. I felt like I had to do that to be legal and stay compliant. When those shackles were finally freed, I ran wild.

The green card meant I could finally leave the country, but more importantly, I was free to pursue my dreams without the constraints that had held me back for so long. I couldn’t wait to explore the world on my terms.

For years, I’d been tinkering with different ideas, running a nonprofit and doing creative projects on the side. But now? Now I could go all in. I jumped at the first dream that was seeded 5 years ago.

Since 2017, I’ve become obsessed with an app called Dedao. It was a well-curated Chinese audio guide full of tech, media, business, and culture content. I fell in love with learning, and it sparked an idea: why not build a company in education? Dedao has open-sourced their playbook every year, so why not create an American version of this?

I wanted to democratize education. I credit a lot of my early success to the knowledge I was able to seek and the people along my ride. Would it be possible to scale that? I had a vision: connect experts who want to share their personal brand with the world to people hungry for knowledge. Democratize access to the wisdom locked away in prestigious institutions. Just like many dreamy startup founders, I wanted to change the world.

I wasn’t completely naive. I knew there was a company called Knowable that had tried to copy the same playbook and failed. They had all the tech influencers and a16z backing them, and they still couldn’t make the business model work. But in my mind? They must have missed something. Maybe the market timing wasn’t right. I tried reaching out to the founders, but both of them didn't respond. Looking back, I should’ve at least tried to contact Connie Chan who led a16z’s seed investment in Knowable. She understood the Chinese market, and we could've learned from their failures. 

I angel invested in my own company to get the product off the ground. I reached out to early believers, recruiting them to join our platform. We had this grand vision of building an advisory board for everyone – not just tech startups with deep pockets, but anyone with the guts to start a business.

Because I was able to recruit friends and big tech employees moonlighting for free, we didn't need a lot of capital. We didn't seek venture funding. At the time, it felt like a strength. We were bootstrapping, doing it entirely our way.

I knew many friends who had been burned from raising VC and having VCs too close to their business. Many VCs recommended that I stay away from VC until absolutely necessary. It's almost like a high-interest credit card that has great benefits and minimum spend. Use it at your own risk.

I avoided that risk, but ended up taking a bigger risk: my time. I could have used some tough love earlier. Even though I had coaching sessions throughout the year, so much of coaching is narrative-based, and I was quite good at making meaning out of everything. What I needed was probably a direct, honest confidant who knew me better than myself.

Chris finally spoke up after observing me for a few months. He asked a simple question: “If a VC were on your board, what would they say?” That question made me realize that I had done such a terrible job that a VC might fire me. The reality of building a startup was messy. The stress about runway, the constant pivots, the rejections. I didn’t experience much of that because I didn’t hold myself to those standards. I would have fired myself already. 

The startup journey isn't just about having a great idea or even building a great product. It’s about understanding market dynamics, establishing partnerships, and learning some hard truths about yourself along the way. 

The lessons weren’t always easy to swallow. But that's the thing about the startup world. It has a way of teaching you things you never even knew you needed to learn. It’s a different kind of freedom—the freedom to fail, to learn, to grow.

The truth of my startup journey isn’t always pretty, but it’s real. And if you’re thinking of starting your own company, well, maybe you can learn from my mistakes. Or maybe you’ll make the same ones. Sometimes that's just part of the journey.

Either way, let’s dive in.¹ This is the story of how I went from a free-wheeling entrepreneur to someone hopefully wiser.

1. Chapter 2 will be released next week.