My first startup raised $250K from an angel investor. It felt like sh*t.

Hey Greenblasters! 👋 (Hmmm. Not sure about that one).

Today I’m sharing the story of my first foray into entrepreneurship. This is after:

• 16 years as a child actor in film & TV

• going to theatre school to become a “real” actor

• hating it

• quitting the business

• becoming an ESL Teacher in Spain

… PLUS 4 takeaways from that experience.

Enjoy:

Before I knew what the word entrepreneur meant, I found myself as the co-founder of a company.

It was in an industry I’d learned a bit about, namely teaching English as a Foreign Language abroad, but I had no concept of what I was doing in business.

When our CEO raised this money, none of the founding team had any business experience.

None of us had been to business school, none of us had started a company before, and no one knew what terms like “cap table” “articles of incorporation” and “voting shares” meant.

We certainly didn’t know how to start and scale a company.

But we had a quarter of a million dollars, and we went for it.

It may sound exciting, and in some ways it was. The issue was, due to our lack of experience, the money began to feel like a burden rather than a blessing.

We hadn’t even received our business license in our country of operation, China, and already we were burning through cash just to try and establish the connections on the ground there that we felt we needed.

We worked for rival agencies, pretending to be just another foreigner in Asia teaching English, while secretly collecting info on our competitors’.

We would omit or even outright lie to anyone who asked us why we had come, worried that if anyone found out what we were up to, someone might steal our idea.

And on top of all that, we had no formal agreement either with our investor, or amongst each other as shareholders.

All of this felt incredibly stressful, and after 1.5 years of living there, working insanely hard and paying ourselves next to nothing, I suffered a major back injury, and had to go back to Canada.

What was supposed to be a month of surgery and rest turned into a year-long painful recovery. I eventually quit the start-up. With no agreement in place, it was as straightforward as an email.

The realization that I might lose my time investment and my (I had just learned this term back then) “sweat equity” made me sad.

But the fact that I was so relieved that the ambiguity of the money no longer hovered over me, told me it was the right thing for me. 

That experience, to date my only experience raising that much capital, taught me some key things:

1. Make sure working on your start-up feels right, in your bones. If it doesn’t, get the fuck out.

2. Always draw up very clear agreements from the beginning, even if it means paying multiple lawyers.

3. Don’t try so hard to hide your intentions as a founder. NDAs and secrets, while sometimes necessary, say more about your overinflated sense of your idea than they do about the actual value of your idea.

4. And finally, I got into entrepreneurship for the freedom. If you’re spending someone else’s money, you’re not free. It might be worth it, but it might not.

That’s it for today! Please FORWARD this email to an entrepreneur who might like it, and let me know what you think!