Have you ever felt behind in life?

Behind on your finances. Behind on your career.

Behind on your full potential?

I have.

I felt it for the first 30 years of my life (and sometimes, I still do).
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Because we're all capable of great things and as Maslow said - "What a man can be, he must be".

For me, I didn’t realize until later how much my birth order affected me.
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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 two 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 pursue finance after high school.

Failure to launch

In my first year at college, 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 needed 50% to pass a class. You could get half the stuff WRONG and still get through.

Then came Accounting 101. I bombed the test. Failed the class.

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...

How can you make this a great turning point in your life?

That message stuck.

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

It was the opportunity to start a new chapter where I showed up for my future self.

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

Starting in Finance

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

Almost overnight I went from helping cleaning ash trays and wiping tables to helping companies make $100 million and sometimes billion dollar deals.

‍But it wasn’t all sunshine and rainbows.

My girlfriend had moved from Canada to live in Australia with me.

But like most people that worked in professional services coming out of college - I got put through the wringer.

Late nights. Weekends. You name it.

It was tough at the timI’d do it all over again if I could.

It learned a ton of skills in a short period of time. But after five 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 a 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.

The best place to do that was in the United States. 🇺🇸

Leaving Australia

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 fall behind my peers that stayed on that stable escalator to financial freedom.

But we knew we had to answer the call. I trusted that we could figure it out - and somehow - 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 was great, but the biggest lesson was one of inspiration.

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

So after a couple of years I was looking to start my own company.

I left the company with everyone's support and got on my way.

One of my best friends from childhood was sleeping on our couch and we were exploring ideasn

One day over a bowl of ramen in Japantown - 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.

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

We abandoned the office and transitioned into remote work.

Other companies did too.

This put a wind in our sails 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. For the next 12 months we helped them integrate the business into a larger portfolio.

By 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

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.

This was tough, and we carefully navigated the market for 24 months.

Thankfully we were 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.

Now with our two young girls and chihuahua, we decided to move back to Australia.

Connecting the dots

After 10 years away and having finished what felt like my personal quest overseas, it was the end of chapter 1 of my life.

There were many lessons, but one of the biggest ones was that we can all feel a little behind sometimes.

You might even feel this yourself.

The person we want to catch up to isn't our older siblings or other people. It's actually the best version of ourselves.

I share the lessons that I’m learning on my own journey in a newsletter covering business, money and mindset.

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

Thanks for stopping by and don’t be shy to reach out.

Cheering you on. ✌