Investor Girl Britt

06/05/2026

06/04/2026

I remember the exact day I decided I would never work a regular job again.

I was a receptionist. It was -50° outside. So cold that my eyelashes were covered in ice and I couldn’t feel my face. (Canadian Winter 🥶)

I called my dad on the way to work and just said “I can’t do this.”

I don’t want someone else controlling my time. I want to be my own boss. I want to make my own schedule.

And that was the moment.

Now I won’t pretend entrepreneurship doesn’t have its own version of -50°. Because it does. There are days that feel exactly like standing at that bus stop. frozen, uncomfortable, wondering what you’re doing and why.

But I would choose this over that receptionist job every single time without hesitation.

The difference is when it’s hard now, it’s hard on MY terms. I’m building something. I’m in control.

So here’s the question I want you to sit with:

What pain are you willing to take??

Because there is pain either way. The pain of staying stuck in something that shrinks you. Or the pain of building something that scares you.

06/04/2026

Back in 2016, I had 4 properties and decided to start documenting my real estate journey on Instagram.

One of my first posts was a photo of my little office setup.

The best part was my “why” board.

I wrote:

“I think it’s important to have a visual reminder of what you are working towards and what the end goal is.

I know the years coming up will be tough and I’m going to work my ass off to eventually get to the places I want to be.

As long as I can stay focused on my goals and remember why I am working so hard, I know I will be able to achieve whatever I want in life.”

Reading that now honestly gives me chills Because I was so right😅

Those years were harder than I ever expected…But my life now is also better than I ever imagined.

That version of me didn’t know all the deals, failures, renovations, breakdowns, risks, and lessons that were coming! She just knew she wanted more and she was willing to work for it.

That’s why I share my journey. It proves what can happen when you stay focused long enough to become the person who can handle the life you once prayed for.

06/03/2026

Years of being a waitress taught me 4 skills I still use in real estate investing today:

#1 sales
I was practicing sales fundamentals every day. building rapport, anticipating needs and working in a fast pace environment with high pressure

#2 customer service
Because waitresses are the best at making unhappy people happy

#3 multitasking
There's 1 million things going on you have to make sure everyone has their drinks, food, checks and make sure everyone's happy and everything's taken care of

#4 work ethic
I didn't want to get paid a set amount per hour I wanted to serve as many people as many tables as possible so I can make more money.

As an investor, these skills help me all the time as I'm networking, analyzing deals, building my connections.

How can you use skills from your current jobs to help you as a real estate investor?

06/02/2026

As a small-town girl from Canada, reaching financial freedom, having a business that runs without me, and being able to travel is truly a dream come true. And it never would have happen if I hadn't started Thinking Bigger, Sooner.
Big thinking feels risky in the moment.
But small thinking steals your time, potential, and opportunities before you even realize it.

I dive deeper in this week's Thinking Bigger, Sooner Newsletter.
Link to sign up:

Welcome to the Thinking Bigger Sooner Newsletter. Get a short, personal note from me weekly about where I am in my investor journey, including upcoming (mostly free) education opportunities.

06/02/2026

How does your work contribute positively to your life (outside of paying the bills)?
Real estate investing has given me way more than money.

just a few examples…

1) Endless Opportunity
I started with tiny fixer uppers and eventually scaled into apartments, self-storage, hotels, and larger commercial deals through partnerships and leverage. There are so many different paths in this business.

2) Keeps Me Creative
Design, renovations, branding, marketing, problem solving, deal structuring... real estate can be a great way to stay creative.

3) Builds Knowledge
Real estate changed the way I think about money, business, leverage, opportunities, and life. There is always more to learn.

4) Expands My Network
Some of my closest friendships, business partners, and biggest opportunities came from getting in rooms with other investors.

5) Improves My Mindset
One of the biggest things real estate gave me was a new way of thinking about what’s actually possible.

6) Location Freedom
This was why I started in the first place. The goal was to have a business that could make money without me being there. Fifteen years later, it's still the best decision I ever made. It's literally a dream come true.

06/02/2026

👌

05/29/2026

In high school my dad said something that changed my future (I just wasn’t ready to hear it back then)

“Britt, self-storage is a great business. Good money, little effort. You’re basically just renting out metal boxes.”

I was a teenager…. So, I filed it away and forgot about it.

Fast forward to 2019 when I’m renovating little houses making a few hundred dollars a month in cashflow.

Then, I heard AJ Osborne on a podcast say he made $13 million on a single storage deal🫢

I sat there like… wait. My dad told me this yearsss ago.

I knew I had to find a way to get into this.

So I tracked down the right partners, learned the asset class, and started buying .

By 2022 I had partnered with AJ himself, bought it on 12 storage deals and co-founded the largest self-storage investing community in the world.

And it all started with an offhand comment from my dad at the kitchen table when I was 16.

The best investing advice I ever received came for free😅 I just wasn’t ready to hear it yet.

What’s the best money advice someone gave you that took years to actually sink in?

05/27/2026

Giving you the secret real estate investor formula🤫

05/27/2026

A mentor gave me one piece of advice that made me $1.2 million🫢

Here’s the story-
I was about to walk away from a deal because I was drowninggg in problems.

He said: stop. “Zoom out. Answer two questions.

Will it be worth more in 10 years?
Is it paying all its expenses today?

That’s it. Nothing else matters right now.”

Both answers were yes. So, I bought it.

That deal went on to generate hundreds of thousands in cash flow and equity (and I almost let fear kill it!!)

Most investors don’t lose deals to bad fundamentals.
They lose them to overthinking.

That two-question filter from my mentor cuts through all of it.