“Stop Being A Big Shot”: How I learned to start where I am with what I have

“Stop being a big shot” was the best advice I received as a young entrepreneur and content creator. It came from one of my friends who was one of those hustlers who succeeded early and knew what the hell he was talking about.

So my first real startup began like most; Two friends sick of their office jobs, branch off on their own and work very hard to change the world. Our plan: to revolutionize digital content creation and distribution. We created a very intriguing digital thingy that allowed audiences to create and interact with online content in whole new ways. Cool stuff. Really.

“What we need to do now is build a website”…

We went through the usual start up struggles, we got a few thousand bucks together, we hustled, raised a little angel investment, and eventually got a sizable chunk of funding. We were off, sky’s the limit. So we say to ourselves “what we need to do now is build a website. A really cool website”. And this is the point when we set out to make the mother of all websites. It would be edgy, but clean. It would say just enough to peak people’s interest. So we hired a really talented British design firm (Who were awesome buy the way. None of what I’m about to tell you is their fault). Simultaneously, we had a bitchin’ startup-y logo made and then proceeded to spend an obscene amount of money and a boatload of time getting the site built. Much blood and treasure later, we were ready to hit the pavement. With a website like this, who could fail?

With new shiny site in hand, my partner and I proceeded to go out into the world to sell our wears. We were convinced we were about to blow people’s minds. There we were, young entrepreneurs, with their brain-melting tech, dressed in that entrepreneur costume everyone with a digi-widget seems to be so fond of…”They wear jeans with a blazer? Holy shit, they must be breaking all the rules.” Short Pause… wait for it, wait for it… THUD. People were, let’s say, whelmed. For a host of reasons, it just didn’t catch on. We got a lot of, “This is really cool, but…”

What we really need to do is appear bigger… like really big.

Like tons of young, eager entrepreneurs we said, “Why let an early, lukewarm response stop us? All we need to do is lick our wounds, adjust, and we’ll be back in the game.” And to our credit, we were right to do so, but it was the way we decided to adjust that spelled disaster. Never the less, that’s when one of us said to the other, “I think they think we’re just a couple of dudes with a digital thingy. What we really need to do is appear bigger… like really big. What we’ll do is have different divisions; a content division which we’ll split up into unscripted and scripted but we’ll go niche, right?” “Yeah, really niche…food and thrillers.” “And we’ll have our technology division too, right” “Right… and we’ll give all these divisions separate names with separate websites so our audience doesn’t get confused” “Fucking Awesome, Dude”. Again, what could possibly go wrong with all this ill-advised entrepreneurial adventure… and to our naive shock, once again, crickets.

This was the moment my friend’s advice came screaming back and perched itself back in my ear. This is when I learned not to be a big shot. Not to be a person who was ashamed of starting out and being new at something This is the moment when I learned to lean in to who I was, to where I was, and to what I had…. in that moment.

What if we admit that we’re just starting out…

Since then, I see it all the time. In the privacy of people’s rooms, they are completely logical. They are calm and know exactly who they are. But the minute they put their stuff out there or face somebody across a conference table, they all of a sudden try to get everyone to think they’re Apple, or Quentin Tarantino or the inventor of White Out. When did they think that pretending to have offices in Barcelona and Sydney was going to so dazzle successful, busy and smart people that the checks would come rolling in?

What if we admit that we’re just starting out, we have a lot of experience in one field, and now we’re taking all that experience and we’re moving it into another. What if we let people know we’re super excited, we have something unique to offer and this is going to be a business that adds value to people’s lives. What if we simply say, “Here is my argument as to why my shit is worth paying for and if you use it, here is the outcome I believe you’ll have.”

In the end, humility is perceived as strength and bullshit and feigned confidence is uncovered with the same embarrassment and shame of someone who just got caught stealing a meaningless trinket from CVS.

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