5 Lessons Entrepreneurs Can Learn from Hamilton

Ok, so first things first: HAMILTON IS LIFE.

The last time I fan-girled this hard is when I was obsessed with Harry Potter at14.

I had heard about it already and knew about the pop culture references. I knew Lin Manuel Miranda performed at the White House which gave the musical the fame it needed and deserved. When a good friend came to visit from Australia last Christmas, we decided to go down to London for a couple of nights so we could watch Hamilton. We’re both really into our social justice, we are loud supporters of the BLM movement and have both been involved in human rights campaigns for years before. Hamilton, with its strong messaging is therefore right up our street. (BTW, you don’t have to be super woke to appreciate Hamilton, in itself it is a wonderful piece of art).

Watching Hamilton live is incredible. I’ve always been a huge fan of theatre, particularly musical theatre. I credit my high school music teacher for exposing us to so much. We watched so many musicals and opera, sometimes even I'm impressed with myself. When I’m in a theatre my senses get heightened and I get super emotional, I feel everything acutely. I get super emotional. I remember getting teary at Andre Rieu live in Sydney a few years ago.

Nothing has been a sensation for me as much as Hamilton. It is special for me- I grew up studying American history. As they sing I hear echoes of my history textbooks from my youth. It’s like a weird memory lane situation, except it’s not my memory. It’s the legacy. And then to watch the most diverse musical theatre cast EVER literally talk about slavery … it fires you up. You feel a fierce pride for the world that you are contributing to.

I wanted to share a few key lessons from Hamilton. In an attempt not to spoil the show for you, I’m going to share specific lines and then expand on them with my own story. I will parenthesise lines from the show.

Dear entrepreneurs, this is for you:

History has its eyes on you

The first time I saw this on a sign in a picture of the BLM protest, I have to admit I shed a tear. There’s a famous saying going around: if you wonder what you would have done during slavery, if you would have been on the “right side of history”, whatever it is you’re doing now, is what you would do then. Because while there are injustices in the world, and you keep your head down and work only for your benefit… that’s your legacy.

I’m not saying that everyone needs to draw out their bayonets, but do think about your actions. That’s the lesson. What do your actions say about you? What can you do? We all have a platform nowadays, thanks to social media. Heck, blogs are free to start. Are you a keyboard warrior? Do you stand on street corners during protests squirting hand sani in people’s hands? Do you help make signs? Do you support people in need?

I’m going to talk about your legacy in another point below, but just remember: history is watching. Pull yourself out of your own ego for a minute and take in the world as it is. With humans. With stories. Millions and millions of stories. What is your story? What category is it going to fall under?

I know what I want my labels to be: fiercely loyal and strong. Leadership. Bravery.

Be brave.

There will always be a hurricane/the world turned upside down

The world is upside down… They call these ‘unprecedented times’. We know. In the last decade we’ve seen so many upsets, so many “what the hell?!” moments.

So many successes are borne out of tragedies. Uber, Airbnb, I believe even Amazon were created out of a recession. Our resilience is what pulls us through, each and every time. One huge driver for people is pain: wanting to better our circumstance.

Societal pressure was my hurricane. And in the quiet moment (eye of the hurricane) is when we make decisions, based on gut instinct and desires. I have goals. I want to reach them. And when I take a moment to recover, collect myself, I am able to find the fire within me to rebuild.

Hurricanes rage - they are unpredictable, they are scary. They can tear your entire life apart. Growing up in Taiwan we had typhoon seasons that ravaged and raged. One weekend, when I was living back at home in my mid-twenties, my parents both went on holiday abroad and I was left to look after the huge house I grew up in. The typhoon raged like a mofo. It was terrifying. Our roof had a leak and the trellis of the balcony fell apart in the wind, banging on the window dangerously.

I slipped on our marble staircase (a new leak had sprung) and fell on my hip. I cried out in pain and was then reduced to tears in the foetal position on the cold stone landing. The hurricane was raging and I felt helpless, powerless, fearful. The power went out. I had to put my phone on airplane mode to preserve battery. I felt alone. Unsupported. Isolated. I was at a turning point in my life- right after this weekend, I decided to turn my life around. I jumped into my online business. I was going to create my own empire. I was going to create my own ”house”, and having survived the typhoon, I knew I was going to survive the typhoon of running my own business, too.

Looking back, I honestly don’t know how I made it through those 3 days. It feels mostly like a blur, with bits and pieces coming back to me as I write this. What I took away from the weekend was the inner strength I didn’t know I had. I was strong, I could weather the biggest typhoon in years, by myself. I could tie down the trellis in howling winds, I could mop the staircase, empty the water bucket in the attic perched precariously on a rickety ladder.

Say what you want, as horrific as it was, it was character building. It set me up for the confidence, resilience and strength I needed to go out on my own.

So while the world is howling around you, telling you what you “should” do or “must” do, tie down your trellis. Mop your floors. You do what you need to do to survive, to thrive. The world is going haywire right now- stick to your guns. Live by your values. Empty that water bucket even though it’s 3am. The reward? The house is still standing, still strong. Wiser. And that’s what you are.

The world is wide enough for both you and me

We’ve been conditioned since childhood that there can only be one winner. That there is only one champion. There are losers.

I’ve got a newsflash for you: in the game of life, there are no losers. Only people who didn’t seize opportunities. My brand is totally different from every other business coach. No one has lived through life as me, I am a bloody snowflake. If there were only 5 business coaches in the world, they would make a lot of money but they would also never sleep because of the demand of business coaches.

Same goes for literally everything else. If you want to open a jewellery store on Etsy, by all means go ahead. Yes there are 5,000+ other moonstone earrings. But people are gonna buy them- why not yours?

The world is wide enough for all of us. There is enough space for all of us to live on this planet, enjoy the seasonal fruits and vegetables, and there is enough money to go around too. This is critical. As soon as you start living in abundance, you will see there’s actually enough space for you to co-exist with your competitor (in Hamilton’s case, his enemy).

You don’t need to put others down to rise up. You need to rise up all on your own. On your own merit, on your own grit. That is what truly counts.

You will never be satisfied

Satisfied is one of my favourite songs in the show. It’s truly incredible writing and Renee performs that part so effortlessly, your jaw will drop when you hear her rap.

Anywho: satisfaction is something that eludes many entrepreneurs. We are always chasing after the next best thing. We are always fighting for the next battle before we help our wounded and count our dead. One goal has been achieved, and on we go to the next one already. It’s an incredible cycle that is, admittedly, very difficult to break out of.

Hamilton was never satisfied. And ultimately, in my personal opinion, was his downfall. On so many levels. And if I’m being honest with myself, my inability to be satisfied has been my downfall.

So tread carefully here- do some inner work here. You need to understand what satisfaction means to you personally. You need to bring that into light for yourself. Find satisfaction in your work. A deeper meaning. For me, knowing that I get to serve people and support them has been so crucial to my success. My clients aren’t just figures in a bank account to me. They’re a mission. And that’s what helps me serve better, produce better results regularly.

Who tells your story?

This is, of course, the whole point of the show. The legacy. The story. Lin Manuel Miranda wrote this show beautifully, shared with us insights that we otherwise wouldn’t have had. He brought history alive. I wish more history was written in this way, much more accessible than we ever thought possible.

So, let me ask you: who is going to tell your story?

There’s a great line in the show, where Aaron Burr says “now I’m the villain in your history”. Was he really a villain? Some people call him the anti-hero. He might very well be misunderstood. But at the end of the day, actions also speak louder than words. So, to round all of the lessons up: what are your actions, that lead to your legacy? How will you be remembered?

A lot of people have children for similar reasons, to have a legacy to pass down. I somehow skipped the biological clock so I don’t think that way. I’m more interested in the time I have to write myself. I’m lucky in the sense that no one can burn the Internet. My words are now being written into history, preserved online for everyone to see. I will use this as my medium. My sword is my keyboard, my blue-light blocking glasses are my visor.

I’m still unsure who is going to play me in my biopic- I’m hoping a young, mixed-race actress graces our screens soon and goes on to international fame so I can get her to play me hehe.


While we are living in such a crazy, f-ed up world, I am grateful. Grateful to be here at this moment. This is my era, I feel it strongly. These are the times that I want to experience, learn from, support, and create. This is truly my time, and your time. It is our time. We have ample supplies and we get to use our creativity. We can learn from our ancestors and push the agenda for progress.

There is so much greatness, goodness in the world. We just have to be willing to find it. I want to thank you, for bearing with me while I talk about something so close to my heart.

I want to thank Lin Manuel Miranda for being an amazing, incredible human being coming up with this and all the people that made Hamilton such a joy (that includes the Obamas, I believe).

I want to thank our ancestors, our families, for bringing us to this moment now.

It’s our turn to change the world, it’s tour turn to make the world a better place. Let’s go.


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