I sent a diaper cake to Gary Vaynerchuk and got a 15-minute meeting.

Back in November 2012, I was a first-time founder raising money for my newly formed startup company. I found myself vying for the attention of investors with my elevator pitch.

This was pre “Lean In” and “Me Too.” There was no #GirlBoss or #WomenInTech movement. It was a time when a comment like “your market’s not big enough” was still code for “you’re targeting women.” Not yet privy to the challenges of being a female founder, I forged ahead with naive confidence.

After college, an internship boss once told me if I wanted a real job I needed to “perfect” my resume. After sending 300 resumes and still no job, I started following Gary Vee in pursuit of a mentor that actually understood the difficult post-2008-crash climate. The #1 thing I learned from him was to stop following the crowd.  

Years later, that same advice would inspire me to start my own business. 

Coming from a small town of fewer than 1000 people, with a liberal arts degree from a place no one “up north” had ever heard of, my connections were limited. As a newbie in the startup ecosystem, it took every ounce of energy just to get in front of investors, let alone earn their serious attention. 

When I learned that my favorite guru was a successful investor in his own right, I wanted a seat at the table. So I did what any follower of Gary Vee would do: I took his own advice. 

Gary’s birthday was coming up and he had just welcomed a new baby. His immense passion for the New York Jets was also well known. After some serious digging for his address (not advised), I got on Etsy and ordered a New York Jets-themed diaper cake—with my Executive Summary attached to it. 

It was scheduled to be delivered to his doorstep . . . or so I thought.

Hearing only crickets, I sent a follow-up e-mail. 

Within days I received this…

To be clear, I didn’t live in New York. Nor did I have a trip planned. My home base was Cincinnati, Ohio. But after receiving his email, I packed my bags and made an impromptu visit to meet Gary Vee at Vaynerchuk Media’s offices in New York City.

This wasn’t about getting funded or even about Gary Vee himself. This was about getting rid of my limiting beliefs about whether I had what it took to get in front of investors. 

We’re taught as founders that there is an optimal time to raise support. That we’re supposed to first perfect our pitch deck. (Sounds eerily like my old boss, right?) We’ve been conditioned to stay in line. Pressured, even as entrepreneurs, to follow the status quo. 

While that strategy may work for the Ivy League grad or the McKinsey & Company intern, it doesn’t bode well for the rest of us. Instead of being reminded to follow, we need encouragement to step out.

Ultimately, Gary didn’t invest that day, and to be honest, I’m not even sure I asked him to. But he did give me far more than the 15 minutes he had promised, and a lesson I couldn’t have otherwise learned. 

The next time you’re struggling with getting the meeting, the pitch, or the job, remember this: don’t just blend in if you want to stand out.