💌 Letter from Olivia

If you're reading this, there’s a reason. Maybe you’re in that weird in-between season.

Maybe you’ve bought your first property, or even your second or third. But now you’re wondering… what’s next?

The questions start swirling:
Should I buy another House Hack or STR?
Should I get into commercial real estate?
What’s the fastest path to leaving my 9–5 for good?
Should I start or scale a business through social media?
How do I work part time and travel the other half of the time?
What’s the best way to retire my husband as fast as possible?
How do I actually live the life of my dreams, and stop worrying about money?

You might feel a little stuck, or maybe even a little scattered.
Like you’re working on a million things and nothing is actually moving.
And because you want to do it all (which, same), you end up doing nothing.
Disappearing. Pausing. Freezing.

You’re a multi-passionate girly and I love that about you! But as a fellow multi-hyphenate, here’s something I had to learn the hard way:
When everything is important… nothing gets done.
And when everything feels like a constraint, nothing is a real constraint.

There are different seasons for different goals, but the magic happens when you choose what matters most right now and go all in on that.

And that’s exactly what we help you do inside Leap Year.

Maybe you’ve started scaling that real estate portfolio.
Maybe you’ve started building the business.
Maybe your life looks “successful” on paper, but something in you knows there’s more.

You want freedom — but also fulfillment.
You want wealth — but also joy.
You want to leap — but you’re not sure what you’re leaping into.

More alignment. More ease. More joy. More you.

That’s exactly why I created Leap Year.

This isn’t just a community for entrepreneurs.

It’s a sacred space for high-income, wildly ambitious women who are in the messy middle.

Those who are done performing for achievement and ready to live deeply aligned, radically free lives, built on their terms.

Over the past few years, I’ve helped hundreds of ambitious women buy their first investment properties. But more than that, I’ve built a life that actually feels like mine. 

I’ve grown a $3M real estate portfolio, started multiple soul-led businesses, and traveled the world with my dog. I’ve surprised my best friends with fully paid getaways, spent slow mornings in places I used to only dream about, and filled my days with joy, presence, and the people I love most, no permission slip required. But the best part, is I wake up energised every day to do the work that my soul was called to do.

But even after all that, I realized something:

No amount of strategy matters if your life still feels like a checklist someone else wrote.

So when I sat down to design this space, I asked myself a different question:

What do I wish existed when I was in that messy middle — where the money started coming in, but the life I craved still felt out of reach?
Who do I want around me to celebrate the big wins and hold me through the hard moments?

How do I SCALE BIG, without burning out and wanting to burn it down in the process?

Because here's the truth:

A lot of people have freedom on paper, but still feel stuck in hustle or proving mode, in a version of themselves that is too afraid to let go of the grind.

The turning point?

Learning to live, not just build.

That’s where Leap Year begins. It’s the space I wish I had in that season.

Not another strategy call or blindly chasing goals, but a container to ask deeper questions.

It’s about going deep, getting radically honest, and creating a life that feels good now — not in five years.

What do I actually want my life to feel like?
What would I do if I stopped waiting for permission?
What does my version of success really look like?

Yes, we’ll give you tools to scale to multiple 6 and 7 figures.
Yes, we’ll support you with systems, strategy, and structure.

But it’s not just about buying the next property or hitting $1M.

It’s about designing the gap year you never gave yourself.
The business that fuels your soul and your savings.
The real estate portfolio that gives you Fridays off to fly to Italy, just because.
The mindset that lets you stop chasing… and start choosing.

Inside Leap Year, we’re not chasing door count, we’re building lives that feel like us.

Because the goal was never to build a life you need a vacation from, it’s to build one you never want to escape.

This is your Leap Year:
The space between who you’ve been and who you’re becoming.
The year you go all in on you, not just the investor, but the woman behind it all.

And the best part? You don’t have to do it alone.

We’re leaping too, and we saved you a seat.

Your leap starts NOW!
Olivia xx