Embrace Being the Underdog

Jay Block
3 min readSep 5, 2019

Us Entrepreneurs, we’re crazy. Yes, that’s right absolutely out of our minds. Like, think we can create something, bring it to market and get people to take money out their pockets and pay US- kind of crazy!

Leave a steady job for a roller coaster- who does that?! An entrepreneur.

One thing I’ve noticed in myself as well as with other fellow entrepreneurs is that we fake it a lot. We think that the only way to survive is to tell people we’re a lot bigger than we are.

It comes in MANY forms. Like:

Sending an email to someone we want to do business with and writing “Dear X, We’d like to propose…..

WE??!!! You’re a ONE MAN SHOW DUDE. Why don’t you just write “I’d like to propose….” Because, we’re scared that if they find out it’s just ME they’ll never listen.


Dear X, We’d like to propose the following… due to some renovations currently happening in OUR office, let’s meet at the Starbucks located at…..

DUDE- You’re working out of your garage with no electricity and a lamp plugged in to an extension cord. WHAT OFFICE AND WHAT RENOVATIONS???!!

But we’re scared that if they find out they’ll never agree to the meeting.

Aside from the fact that the truth will end up spilling out (when they check the mailing address on your website and they “swing by” and find out it’s your Grandma’s basement)-

Most People CHEER On the Underdog!!!!!

When you see someone just absolutely grinding out a great idea, you don’t care about the garage, the one person team or the lamp- in fact those become HUGE assets!

Gail Becker is an incredible entrepreneur who quit her job as president of Strategic Partnerships and Global Integration at Edelman, one of the most prestigious PR firms in the country and set out to build one of the most amazing brands in the food space- CAULIPOWER! Since then, the CAULIPOWER brand has already enjoyed recognition around the country and earned over $100 MILLION in sales in just over two years!

One of the most interesting nuggets I took away from my recent interview with her (HERE) was this:

But the lesson overall is that, early on, I really tried to pretend to be bigger than I was. Because when you’re trying to get in that frozen door in the supermarket where there’s multi-billion dollar companies that are represented in that door, there’s not a lot of space. I thought I had to pretend to be bigger and stronger than I was. And what I realized was there are a lot of people cheering on the entrepreneur. And when you embrace that and you accept that and you ask people for help, I think you’d be surprised about how many people cheer on the entrepreneur and help you along your crazy journey.

So, to my fellow guys and gals who are daring enough to make the move to becoming an entrepreneur- DON’T FAKE IT!

Let people know “your weakness” because “your weakness is your STRENGTH!”

What are your thoughts? Have you felt the need to fake it? How did that turn out?



Jay Block

"You are your company" I love sharing the stories that have made brands and entrepreneurs successful. Jay@TheSBJournal.com