How Gary Vee Shattered My World in 2019

Hey there, it’s Aaron coming back to you with another email from beautiful Colombia.

I hope you’ve had an amazing month so far. I can’t believe it’s almost January—30 is right around the corner, LOL. I’ve been going crazy with content recently, so I hope you’ve been keeping up. I just posted my second YouTube video, so it would mean a ton if you checked it out. Shout out to Ned for helping me capture amazing footage and post consistently.

Before I started my adventure in Colombia, I gave a keynote speech that some of you may have attended. It was my first one of the year, and I’ll be honest—I was nervous as hell. But standing there, looking out at over 1,000 people, I realized something important: we all face limiting beliefs, and it’s how we handle them that defines us.

So, let’s talk about limiting beliefs and the two words that changed my life.

I come from humble beginnings. My parents were immigrants who landed in Toronto with my three older brothers—three kids under five—with nothing but a dream and maybe a couple of bucks in their pockets. My dad drove a truck for 20 years, and my mom cleaned houses. We were five kids sharing one room, triple bunk beds and all.

When I was 13, everything changed. My mom started her first business, and suddenly, things were looking up. We went from sharing that cramped room to each having our own. We got our own cars. We even went on our first family vacation—a cruise that blew my mind.

But three years into this incredible, life-changing moment, it all came crashing down.

I watched my mom’s business crumble overnight. The house, the cars, everything—gone. I remember asking her, “Is it over? Is this it for the Spivak family?” And she looked at me and said, “Not yet.”

When I heard those two words, that’s when my entrepreneurial journey started. They became my secret weapon. But it wasn’t until later that I really understood their power.

Fast forward to 2019. Hush was a $1 million business, and I was hungry for more. I snuck backstage at a Gary Vee event in Toronto and hit him with the question: “Gary, we’re a $1 million business. I want to go to $10 million. You think we can do it?”

His response? “What’s your name?”

“Aaron,” I said.

“Cool, Aaron. If I was running your business, you think we would do it?”

Without hesitation, I blurted out, “Heck yeah! If you were running it, we’d be a $50 million business!”

And that’s when it hit me. The only thing holding us back was my own limiting belief. If I believed Gary could do it, why couldn’t I?

That mindset shift is the reason Hush went from a $1 million seasonal struggle to a $48 million exit in just 48 months.

But here’s the thing—we all have that voice in our heads saying:

• “It’s too hard to go from zero to one.”

• “The market is oversaturated.”

• “I don’t have enough experience.”

Sound familiar?

So, how do we kick those limiting beliefs to the curb?

Here’s the framework I use:

1. Is there a rational reason for this belief?

2. Could I be mistaken?

3. Would I believe the same about someone else in a similar situation?

And let’s be real—sometimes the answer to #1 is “Absolutely yes.” But that doesn’t mean we can’t push past it.

I remember when Hush hit that brutal summer slump. My co-founder and I were about to call it quits. But I channeled my inner 13-year-old and said, “Not yet.” We pivoted our strategy, created our iced fabric, and BOOM—a $1.5 million Kickstarter campaign.

The lesson?

Your limiting beliefs are like a rope tying down a baby elephant.

When the elephant is young, the rope is strong enough to hold it. But as the elephant grows to 14,000 pounds, that same rope shouldn’t be able to hold it back. The only reason it does is because the elephant thinks it should. Our limiting beliefs work the same way—they only hold us back because we think they should.

So, I’ve got a challenge for you:

Take a minute right now and write down one limiting belief that’s holding you back. Got it? Good. Now run it through that framework and see what happens. You might just surprise yourself.

And hey, if you want to dive deeper into crushing those limiting beliefs, come hang with us at our Tulum Founders Retreat this December. We’ll be doing some serious mindset work (in between beach time and breathwork sessions, of course). Spots are limited, so grab yours before they’re gone!

Charlie Munger once said, “It’s good to learn from your mistakes, but it’s better to learn from others.”

And that’s what Founders Club is all about—surrounding yourself with people who’ve been there, done that, and can show you the shortcuts.

Alright, I’m off to explore more of Medellín and get in as much padel as I can before I leave. The people here are incredibly nice and open, and the city is just beautiful. Feels surreal to be working from a jungle—you’ve got to see the view from our flat.

Keep pushing past those “not yets,”

All the love,

—Aaron

P.S. Seriously, Tulum is going to be INSANE. Don’t miss out—Apply now!

P.P.S. If this newsletter hit home, share it with a friend who needs to hear it. Let’s grow this community of founders together!