Why It Feels So Good To Be The Underdog | The Early Startup Life

The advantages of doing it all

A Startupper's Life - By Leo
New Writers Welcome
4 min readDec 15, 2023

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“It’s never just business. It never will be. If it ever does become just business, that will mean that business is very bad.”

Phil Knight, Shoe Dog

If I were to share the memories of the early days as a start-upper, that image would sum it up pretty well:

  • a co-working (a garage is old-school now)
  • bunch of university grads listening
  • a recently self-proclaimed CEO talking

And let me tell you this: few things feel as good as that moment.

As for many cases, it will be extremely easy for those who went through the same experience to say. “that’s it buddy! Feel the same here!”.

However, most don’t know the deep and insanely strong feeling that makes you wake up every morning to keep your idea alive. Do you remember the short tale of a lion and a gazelle waking up every morning in Africa?

Well, close enough.

Because that’s exactly what an early-stage startup is: the constant effort to prove, day in and day out (up until the run-rate comes knowing at your door) that your idea is worth the attention and hard-earned money of your audience.

To me, everything started in May 2018.

End of the academic year: time to prepare for the last exams, start thinking about the final thesis and, hopefully, find a (remunerated) internship for the summer break.

Let’s just say that I was a bit lost.

It’s probably due to that exact feeling when I received that LinkedIn message from a guy building “the next billion-dollar company”, that I quickly fell for the idea that getting my hands dirty in a small startup was not a bad idea on how to enjoy the summer.

I ended up spending the next 5 years there, growing from intern to Head of a department and leading my team.

Not a bad ROI for a summer internship, right?

However, the end of the story is not what matters here.

Although it does sound cliché to say that it changed my life, the heartbreaking ups and downs of an underdog startup life can provide valuable lessons:

1- You learn to: sell yourself as you sell your product

When you are building or helping build (as in my case) something from scratch, you cannot rely on a big brand to do the work for you.

The very first adopters will choose you, not your service/product.

If you think that’s nothing big, think twice.

Advancing in my career I’ve learned that the most relevant asset you might ever have in your toolbox is how you talk to people.

But, bear in mind, to talk you need to listen first.

That’s why being put in a corner by clients not trusting what you offer obliges you to listen attentively to their concerns and doubts. Only then will you be able to explain why the doc/ppt/video presentation that you’re showing them is worth their precious time.

2- You learn to: accept defeats (and so to pivot)

“Fail fast”

It doesn’t sound that bad when a multibillion company executive says so.

Things start changing when you are the one looking in the mirror realizing that your plan (and hopefully you did have one) did not work out.

Hard pill to swallow, trust me.

The positive side of this tale? If after having swallowed many of those lovely pills you’re still alive, it’s more than likely that your attitude toward what you do and how you do it will change:

  • more attention to detail and warning indicators
  • a retrospective approach to your actions
  • a (drastically) reduced fear of failing

Focus on the last one.

Failing teaches you to react, accept your mistakes, and carry on.

Not letting the fear of executing stop you is, in my opinion, the file-rouge among the crazy people out there trying to build something that doesn’t exist yet.

3- You learn to: look at the right things

Among the most valuable lessons that I have learned, one of the top spots is reserved for where your attention should be directed.

Startups are (almost) always required to grow at an astonishing fast pace and the risks of looking at where it’s most convenient are high.

I witnessed growth from 7 to >500 employees in just 3 years.

Yep, that sounds great. “We made it!”. A solidly built startup we can brag about when talking to old university friends.

Or maybe not.

With the experience of the years spent hustling to keep things afloat, I understood that such a metric was just plainly wrong. We should have looked at productivity, rev/FTEs, etc etc.

But we didn’t.

Even if this is just an example, experience “on the field” grants you sharpened eyes, the ones you need to seriously make your goal a reality.

So, yes, being the underdog has some positive sides, you’ll just need a bit to realize it. But, remember, it’s so much better at the end of the unpaved road.

Photo by Artem Bryzgalov on Unsplash

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A Startupper's Life - By Leo
New Writers Welcome

Hidden under a pen name, exposed through my stories | I write to share hard-earned lessons in business and life, guiding others to success without the pitfalls.