My first entrepreneurial experience happened right after my first semester of college.

In January 2008, I did a brief winter internship.

My boss was a part time law professor. Publishers would regularly send him sample textbooks—with the hope that he would select one of their textbooks for his class. The idea is that students would then be forced to buy the selected textbook, and that is how publishers make their money.

Over the years, piles of these textbooks had stacked up in his office—in unused, mint condition.

Some of these law textbooks were quite expensive.  

Very generously, my boss told me that I could sell all of his books keep 100% of the proceeds.

So I took the books home, and I listed them on Half.com + Amazon marketplace.

Soon the books started selling.

I would get bubble-wrap envelopes, pack the textbooks, go to the post office, and ship them to the buyers.

Easy breezy.

Over the course of 2 weeks, I made $1,600.

All-in — the listing, packing, and mailing took 10 hours of my time. So my rate was $160 / hour. Not bad for an 18 year old with no professional experience … and remember, this was 2008 dollars too!

What do you think I did after that?

Or what do you think I should have done?

In reality, I DID NOTHING. Once 2nd semester freshman year started, I went back to school and forgot all about it

Alas – Yishi’s textbook empire never came to be.

What I could have done

In retrospect, I could have approached a few professors at my university and asked them for their sample textbooks. Then, I could have sold the books online and provided the professors a cut.

Given that my school had a couple thousand instructors, even a 1% success rate would have paid my tuition.

If I was even more ambitious, I could have hired a student intern or 2, and scaled to other campuses.

Okay the latter might be a stretch – but at the very least I should’ve talked to a few professors at UC Berkeley and tried to earn some beer money.

But no, I went back to being a normal college student – and I didn’t think twice about it for a very long time.

Over the past few years, I’ve plunged into the world of entrepreneurship. And as I continually reflect on who I am and what I want to do—I began to mentally revisit my textbook-selling experience.

Why didn’t I seize the opportunity staring me in the face in 2008—or at least explore it a bit further?

Why I didn’t do anything

I think there are three main reasons:

1. I wanted to do normal college kid things. I was focused on having fun + getting good grades. Sure, I would’ve liked more money. Who doesn’t? But personal growth was more important to me at that point in my life, where I was still trying to find myself in a psychologically safe environment and fit in with the crowd rather than go off the beaten path.
2. I lacked exposure to entrepreneurship. It wasn’t obvious where entrepreneurship could take me. In 2008, Facebook was relatively new. The first iPhone had just launched. This was before the rise of Y Combinator, Uber, Twitter. Airbnb and all those other iconic start-ups that would come to define the 2010s.
3. I was risk averse. I am the only child of immigrant parents. My parents have zero business experience. My mom was a waitress for many years when we first arrived in America. We had crawled our way up to middle class. Failure was not an option for me. I wanted to make money, and at that point, I wanted to do so in a stable environment, following the conventional path. (Fittingly, my first post-college job would be at Goldman Sachs. I wrote about why I left that world. )

Why did I write this and what does it matter to you?

The circumstances for me to start a business weren’t perfect in 2008. But then again, neither are they now.

The thing is – the timing is never perfect to be an entrepreneur.

The financial and psychological freedom required to take a risk is a luxury.

The good news is that throughout human history, goods that were once luxuries tend to become affordable over time. And now, there are more resources than ever to enable individuals to pursue entrepreneurship.

I feel privileged to be able to take the risks I do. And I’d like to create more equal opportunities in the world. And my method of doing so—of sharing my privilege—is to help more individuals start successful businesses.

In my own entrepreneurial journey, I’ve found that the number one most helpful resource is a thought-partner to talk to—just one other person to help de-risk the idea, push things along, and get it off the ground.

And that is why I started Optionality Partners.

All you need to do is notice an opportunity. It could be a small inconvenience, or a major problem you face in your daily life / work.

You don’t even need to think of yourself as an entrepreneur. You could be perfectly happy with your career / your personal life, but you notice an annoyance that you think should be fixed.

The world will never be perfect. And that is an opportunity for us all.

Come talk to us. We would be happy to listen to you, and maybe we’ll change the world together!