My Story

I didn’t realize how much my birth order would affect my life. 

And like most things, it's only in hindsight that I’ve been able to connect the dots.

I was born the youngest of four children in an immigrant family in Sydney, Australia.

From being the youngest, I always wanted to catch up and prove myself. Not just to my older brothers and sister, but myself too.

This gave me a competitive nature from an early age, and coupled with a love of numbers - led me to pursuing finance in college.

Failure to launch

In my first year, I treated the campus like a drive-thru, in for class and out just as quickly.

My real life was a mix of skateboarding, chasing girls, and believing success would just fall into my lap. Because, here’s what I figured….

You only need 50% to pass - you could literally get half the stuff WRONG and still get through.

Then came Accounting 101.

I bombed the test and failed.

This wasn't just a red mark on my transcript; it felt like a red flag on my life's plan.

My dad asked me...

What are you going to learn from this failure and how can you make this a great turning point in your life?

That message stuck.

Still now, almost 20 years later as I write this.

Failure wasn't the end, but the opportunity to start a new chapter where I showed up for my future self.

Like most obstacles, the failure helped my grow and I eventually got an internship then graduate job.

Starting in Finance

The first real job was a major inflection point in my life.

It felt like almost overnight I went from helping people choose the steak or salad to helping companies complete $100 million and sometimes billion dollar deals.

But it wasn’t all sunshine and rainbows.

Like most people that worked in professional services coming out of college - I got put through the ringer and I’d often find myself way out of your depth. 

But I’d do it all over again if I could.

It's so valuable as you get to learn a tonne of skills in a short period of time. But after 5 years of doing that things had changed.

My dreams had evolved.

I realized that I didn't want to be in the services business forever. I wanted to build something tangible that had an real impact on the world. But I had a problem.

Apart from a few side hustles, I knew very little about real business and had a lot to learn, and the best place to do that was in the United States.

Leaving Australia

So my wife and I packed up all our stuff and bought a one-way ticket across the Pacific.

The decision to move to the U.S. was both exciting and terrifying.

It was a new adventure… but saying goodbye to our people and our life was tough. It made me feel like I was going back to the start of the journey. 

I was going to be falling behind my peers that stayed on that stable escalator to financial freedom. 

But we knew we had to answer the call and trusted that we could figure it out. 

We kind of did.

Meeting the Mentor

We landed in San Francisco in 2015 and I had the opportunity to work under an incredible mentor in an early stage fintech business.

We helped thousands of people save money on their student loans, as well as launch other products into the market like personal loans and credit cards. 

I learned how all the pieces of a business come together to make products and customer experiences.

Each of those lessons were great, but the biggest lesson was one of inspiration.

Because watching this guy wield together a business from a PowerPoint and a dream made me realize - that was the an adventure that I wanted to be on too.

So after a couple of years I was looking to start my own company. And one of my best friends from childhood was sleeping on our couch.

We were exploring ideas then one day over a bowl of Raman in Japan town - we decided to go all-in on building something together.

Helping companies grow

We built a platform that helped great companies like Credit Karma, MasterClass, and Warby Parker onboard and support their people.

This was a transformative period and felt like my Rocky-training cut scene

I got to experience all the extreme highs and lows of building something from the ground up. Getting a product live, building a team, managing investors, dealing with lawyers and HR- you name it.

But none of that prepared me for the biggest challenge yet… 

A global pandemic in March 2020.

It felt like the world stopped spinning for a moment there didn’t it?

With 70 people at the time and almost half a million dollars of monthly payroll to cover, we had to make some time calls as panic set-in.

We abandoned the office and transitioned into remote work. And other companies did too…. this put a huge wind in our sales as our software helped them to do that more effectively.

We ended up having a great year and by the end of 2020, we were acquired by a private equity firm and for the next 12 months helped them integrate the business into a larger portfolio.

At this point, my family and I had reached financial freedom but something was missing.

I wanted to help other people get there too.

Returning to Fintech

So my CTO and I then started exploring alternate assets and we launched a company focused on increasing access to private real estate in the US. Our timing could not have been worse.

From the day we launched the business, interest rates went from zero to five percent which had a huge impact on our market.

That is because in real estate, most of the capital structure is debt. 

So when debt pricing moves rapidly, market pricing gets upside down.

Sellers don't want to sell…

Buyers can't afford to buy…

So a large bid-ask spread is created and deals rapidly dry up.

This hurt and we carefully navigated the market for 24 months.

Thankfully we're able to do a number of great deals, help thousands of investors and find a great owner for the next chapter of the company in early 2024.

This was a transitional moment for my wife and I.

Connecting the dots

Now with our two young girls and chihuahua, we decided to move back to Australia. After 10 years away, I feel like I’ve been able to connect the dots.

I’ve realized that maybe everybody can feel a little bit behind sometimes.

You might even feel this yourself. 

And that person we want to catch-up to is not our older siblings or other people.  It's actually the best version of ourselves that we should be chasing.

I decided that I wanted to share the lessons that I’ve learned in my own journey of self development.

So I started a newsletter on business, money and mindset

I believe if you can get these three things right, you then have an incredible opportunity to support, lead and inspire the communities around you.

Thanks for stopping and don’t be shy to reach out. I'm always open for opportunities and would love to help. ✌

Cheering you on.

Andy Crebar signature

My Why

I want to help one million people live the good life of health, wealth, love and happiness, so that they can better support, lead and inspire their communities.

The journey so far...

Here's what I've been up to.


First job was delivering pizzas, before serving drinks at the bar.


Studied finance and accounting at the University of Technology, Sydney.


Met the love of my life while traveling in Portugal.


Joined Macquarie as a graduate in their technology and media team.


Bought my first property.


Moved to the United States to get into company building.


Sold my first real company.


Welcomed our first daughter - Arlow!


Built an online platform that helps people invest in private real estate.


Welcomed our second daughter - Billie!


Started my newsletter. Subscribe below - its good stuff.