What I Learned From Leaving My Job To Launch a Startup as a First-Time Founder

Failure is one of the greatest teachers you can have and I experienced my fair share of it on the road to pursuing my dream.

Kasra Khalili
3 min readFeb 1, 2022
credit @golimitless

In 2018, I left my career role to launch my first startup in what would be a life-altering journey.

I come from a family of entrepreneurs where problem-solving felt like a religion growing up. However, I didn’t follow that path at first. My degree was in Occupational Safety, Health, & Environment, one of the furthest points from entrepreneurship. Regulation and process dominated our field.

In my role as Sr. Safety Specialist, I focused on corporate program management, regional branch oversight, and training. This afforded me the opportunity to travel constantly and the autonomy to innovate and execute the safety program.

I loved my job. Leaving was one of the hardest decisions I’ve ever made.

Here’s why I did and what learned.

I wanted to make a bigger impact and I saw tech as the best tool to do that.

At the time, I was only 23 years old and heading up safety for 34 locations while contributing at a high level with leadership. What more could I want? I guess more than that… Back then, I always felt like I was up against the clock. As if I only had so much time to accomplish everything I wanted in life.

This ambition led me to form a startup with a couple of friends that we worked on for about a year during late nights and weekends. Even with putting in all of our spare time into the startup, it wasn’t moving. I felt a change was needed.

Two years after getting my friends together to share a cool idea I had, I quit my job to go full-time on the startup.

Being a full-time founder is ridiculously hard.

Being a first-time founder means working ridiculous hours, loss of sleep, and sweating over details. It means some combination of loneliness, stress, anxiety, anger, fear, and depression. Being a founder sucks most of the time.

For better or worse, I was willing to make any sacrifice in order to grow my startup. I thought it was what I was “supposed” to do.

But startup success isn’t just about how hard you work. Working on the right things at the right times is what defines your outcome. Unfortunately, my timing and efforts were off target too often.

A little over two years after quitting my job, we shut down the startup for good, we failed.

The upside of building startups far outweighs the potential failures.

I knew the downside going in; I had watched my family fail multiple times before they succeeded. Experiencing it myself taught me more than I could have ever imagined.

In the trenches of building a startup, I made lifelong friends, learned invaluable skills, and have seen countless opportunities present themselves.



Kasra Khalili

I write about community, startups, & productivity to help early-stage founders and aspiring entrepreneurs take their business from 0 to 1, faster.