How I Risked Everything To Build A $20M Company In 3 Years

Katelyn Gleason
3 min readMar 17, 2018

This post is 3 years old. I wrote it in 2015 and meant to publish it, but never did.

“Often the difference between a successful person and a failure is not one has better abilities or ideas, but the courage that one has to bet on one’s ideas, to take a calculated risk — and to act.” — Andre Malraux

Recently, we closed a round of funding (valuing Eligible, Inc. of which I am one of the founders and Chief Executive Officer) at $20 Million.

Before you read this and think “wow a 20 million dollar company that quickly!”, check out my YC 2012 batchmates, Instacart, who created a company valued at $2 Billion in the same amount of time.

Nevertheless, a

  • Company worth $20M
  • In 3 years
  • Led by a non-technical founder with a theatre degree

is still dare I say — an incredible feat (and one our entire team is proud of).

Secret to Eligible’s success: Risk.

As per the title, for the past 3 years I’ve had to risk every possible human normalcy to get our company to where it is today.

These risks include, but are not limited to: family, friendships, true love, high-paying jobs, health, dreams, youth and admiration. Everything. You name it, I’ve risked it.

Building a company on a shoestring.

There was nothing left. Except an iMac, some lip gloss, a hair clip, and a pizza-box-mouse-pad.

For the past four years, I have not owned a TV, a couch, or any of the other “normal household items.” At one point, my family came to visit and they were literally scared for my life!

Why would anyone in their right minds risk so much you ask?

It must be that I found something worth the risk.

When I moved to Silicon Valley at 25, I saw a world I always knew existed, but almost gave up on finding.

This is a world where people create their life instead of complaining that the one “assigned” to them is unfair (or worse, uninteresting).

In the valley, I found that everyone there was just like me. They wanted their thoughts and energies to be thoroughly used up, lights on, working on Sunday nights, Monday mornings, and Tuesdays at 2 am.

Not because they “had to” or “felt guilty” if they didn’t, but because they wanted to, they were moving the world.

All this, and still the place kept getting better and better.

I found it didn’t matter what school I went to, how much money my parents made, what car I drove, how pretty I was, or what clothes I wore.

All that mattered was the work I did, what I was able to contribute, and what I was able to create.

I was home.

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