About

Jazz musician → English teacher → Entrepreneur

I spent the first 7 years of my “career” as a jazz musician.
I spent the next 7 years as an English teacher, traveling the world. After that, I spent 7 years building a $10M online education business.

And today, I run four separate businesses — StoryLearning, Creator Empires, OllyRichards.co, and TeacherAI — an invest in many more.

Everyone who hears this story thinks the best bit is the part about the successful business. But I don’t.

The Jazz Years…

I grew up playing music.
When I was 16, I became infatuated with jazz. So much so, that I ended up doing a degree in Jazz Piano at one of London’s top conservatoires.
Those were great years.

I had no money. But I didn’t care. I was living a life drenched in music, with the best friends in the world.

But trouble was lurking around the corner.
Maybe I was too immature to commit.
Maybe I loved the music, but not the work.
Maybe I just wanted something else from life.
I don’t know.

Either way, I started to doubt that the jazz life was for me, and I started to drift away, leaving the riffs and rhythms behind.

Here’s what I learnt during that period:

  • Passion dies when it becomes work
  • A life with art is a great privilege
  • It’s possible to be broke and happy
  • Community is priceless
  • 95% of success is hard work (even for the naturally talented)

The Teaching Years…

So, what do you do when you’re 28 years old, and totally lost?
Move to Japan, that’s what.

I did an English teaching qualification, moved to Japan, and lived there for four years.

“Reckless!” some said. (My friends and parents included.)

Me? I just wanted to enjoy life.

Living in Japan was the thrill of my life.
And turns out, I freakin’ loved teaching.

It felt good to help people – seeing students week in, week out, watching them improve, being part of their journey.

But I wanted more than the hectic schedule of an English teacher, so I moved to the Middle East to pursue academic management. There, I entered the depressing hierarchy of a huge, lumbering government organisation.

Something wasn’t right.
I’d swapped the jazz life for this?

My daughter was born in 2015, and that was the excuse I needed.
So I quit, and went back to London. Back to square one.

Here’s what I’d learnt from all this:

  • Teaching and helping others is a virtuous path
  • Learning and development improves and inspires you
  • You can become world-class at a new skill in 7 years
  • Corporate hierarchy, wage caps and lack of autonomy are soul destroying

The Entrepreneur…

London, 2015. With a newborn baby in tow, I moved back to the UK. I was 34.

No job. No home.
(Only parents can truly appreciate how terrifying this kind of situation is.)

The one thing I did have going for me was a fledgling blog about language learning that I’d started while in the Middle East.

I hustled — Man, did I hustle!
I wrote blogs, I wrote books, I did podcasts, I made products. Things grew—as they have a habit of doing when you focus on them.

Before I knew it, I’d walk into bookstores and my name was everywhere.

Today, I’ve published over 20 books that have sold 1.5 million copies worldwide. Our income statements now had 7 figures on them.

For the first time in my life, I had money.
Eventually, I gave myself permission to spend it…
The nice house, the nice car(s), the blowout meals, the business class travel.

The Real Work Begins

But building that business nearly broke me. The anxiety, the burnout, the 2am wake-ups thinking about work. You know what I’m talking about.
What saved me were the lessons from my previous careers.
They gave me the confidence to say: 

 “I don’t care about making more money if it means compromising on the good life.”

So I redesigned everything.

Today, I work 4 days a month on StoryLearning. I have large amounts of blank space in my calendar, and I wouldn’t trade that for anything.

Here’s what I’d learnt from all this:

  • Money is just a game you were never taught to play
  • You can create any life you want (really)
  • Entrepreneurship is a vehicle to create the highest version of yourself
  • Time, money and freedom can inspire and crush you in equal measure

Why I Do This

Once you’ve made the money, it’s through service and impact that you continue to grow.
The teaching is the point.

That’s why I mentor other education entrepreneurs—being the guide I never had when I was drowning in the thick of it. I’ve worked hand-in-hand with creators and business owners to help them 3X their profit while stepping back from day-to-day operations.
In hours or days, I offer what might otherwise take years to learn. Not just tactics and strategies, but the deeper questions:

  • Who are you as a person?
  • What life do you want to build?
  • What does alignment look like for you?

Because here’s the truth:
Your business should serve you, not the other way around.

The Courage to Say No

Thanks to my earlier careers, I deeply understand my own values: Total autonomy over my time and schedule. The value of teaching. The importance of art and creativity in life. I wrote blogs, I wrote books, I did podcasts, I made products. Things grew—as they have a habit of doing when you focus on them. Before I knew it, I’d walk into bookstores and my name was everywhere.

That big dilemma you’ve been wrestling with? It’s perfectly acceptable to say “no” simply because you simply don’t want to.

Have the courage to build a business that works for you. Have the courage to say no. Be skeptical of the lure of money.

Happiness and fulfilment lie elsewhere—community, family, self-expression, being of service to others… oh, and hard work.

If you run an online education business, welcome home.

The best place to start is with my 118-page case study, which you can read free here, or pick up in paperback format if prefer reading that way.

You can also:

Namaste,

Olly