If you could choose to be David or Goliath, which would it be?

The bigger, stronger favorite? Or the counted-out underdog? Expected to win or to be written off?

Well, here's the thing. You never actually get to make this choice.

If you're a startup, you're David. You are the underdog. Capital D.

And as someone who has been through the startup thing several times, both as an operator and investor, one of the bigger mistakes many founders make is that they assume to win, they must be more like Goliath. There's this sense that you have to be more than you actually are. The startups that win not only embrace their David status, they use it as a weapon.

David can, and did slay Goliath. But first comes acceptance. You are David.

You are who you are.

At my current startup, I recently faced this very issue head on in two different scenarios. In one, I made the right call and landed our biggest account by being true to our David. In the other, I made the wrong call and signed off on a website that screamed inauthentic to the most casual observer. As it turns out, this was a lesson to be relearned once again.

Pretending to be Goliath

Last year, our cobbled together website needed a refresh. It wasn't terrible, it's just that we'd finally learned how to tell our story. We'd also zeroed in on some market segments that were ready to listen. Ready to buy. We'd identified the early adopters. Target acquired. So, our site needed to reflect those revelations. We'd also settled on a system to capture leads. A little marketing technology for our video technology startup. A new website was on our radar.

We hired a great firm to help us. They checked all the boxes. They'd produced beautiful work for some peer companies and had helped us on several app projects with high marks. Yet, almost from the beginning, I felt uneasy with our direction. It was more a gut feeling than clear insight. In the end, they produced a site which though professional, simply misspoke. It created an illusion of established. Sober. Mature. Everything we were not.

Even though David pretends to be Goliath, he is in fact, still just David.

Embracing Your David

Several months later despite our mismatched site, we were able to land an RFP from a large brand at the top end of our market segment because of our innovative technology.

I eventually teased out the identity of our foe. A large, public, established, behemoth of a company. At the time, they were literally hundreds times bigger than us on every measurable.

They had more people, more resources, and proven tech. We housed our entire operation in a throw away space from a landlord who invited us in as a favor. We appeared to be simply out-gunned.

And yet, we hung around. At some point, I realized the very parts of our offering that I thought could be viewed as the knocks were being well received.

Yes, our tech was somewhat unproven, but it was new with lots of flash.

Yes, there were parts of our platform that weren't quite finished yet, but our delivery date on those gaps was only weeks, not quarters.

Yes, they wanted some things we didn't have, but our roadmap really synced up with their needs.

Yes, we didn't have a Division 1 football team to dedicate to their account, but our smaller squad proved capable, sharp, and responsive.

Before my eyes, the path revealed itself.

It all came down to a final meeting -- their decision makers in the room with almost our whole company. We pitched our roadmap and our dexterity. Our tech group gave an unbelievable pitch on what we'd accomplished since the start of our courtship. My attorney sat in the room and worked through potential contract terms during lunch and signed off on several changes right on the spot.

Finally, the meeting broke. I couldn't help but be proud of our team and openly gushed in front of this maybe client. I could tell she was with me, on my side of the praise.

On her way out, I pulled her aside for just a moment.

"Kim, thanks for spending the day with us. I hope we impressed you and I want to tell you again how much we'd like to be your partner on this project. As the CEO, you'll have my cell phone, and can call me anytime. I can get stuff done around here."

She was following me. I continued.

"Listen, I know we aren't the safe choice. But today was an indication of how much you'd mean to us. You'll be our biggest client. You choosing us will transform this company and the people here. I know we can do it. We will not let you down."

She paused just for a moment, understanding the weight of her next words.

"Matt, you guys did a great job. We're picking you."

So, here I am with a new enterprise client as we in parallel embark on another website project. This time, I hope to capture some of that magic that won us this big account.

Our internal code name for this new website project?


You are who you are.