Garrett Vargas, Co-founder and CTO at LegUp

WHAT WERE YOU DOING BEFORE YOU VENTURED OUT?

Before I quit my job, I was CTO of CarRentals.com, part of the Expedia Group.

WHEN DID YOU REALIZE YOU WANTED TO VENTURE OUT?

About a year and a half before I left, I realized I was ready to do something different. I started my search “the traditional way” for someone who had worked in large companies – looking at roles at the likes of Amazon, Google, and Microsoft. But I couldn’t find anything that reignited my passion. At the same time, I was getting more involved as an advisor for a local startup founded by an ex-coworker. Following their journey, I realized the diversity of experiences in a startup would give me the strategic and technical challenges I was looking for. I wanted the thrill of knowing what I did mattered and realized the risks of a startup were exactly the draws I was looking for to let me live more.

WHAT INITIAL HESITATIONS DID YOU HAVE ABOUT QUITTING YOUR JOB AND HOW DID YOU OVERCOME THEM?

Like many I was worried about the financial impact of leaving my job but decided to test living without an income by diverting my paycheck to another account. This let me see how much I could cut back and exactly how much I needed to supplement. The great part about this was when I did quit, I had built up enough from redirecting my paycheck that I’m now able to “pay” myself what I need to get by, and know what that personal runway looks like.

Another hesitation I had was whether I’d be able to live up to the pace and expectations of a technical co-founder with limited help, especially as I had only worked in large company roles before. I was able to alleviate this concern through hands-on work with some early-stage companies that let me build up their technology stacks. This gave me reassurance that I was ready to take on this role full-time.

CAN YOU REMEMBER THE DAY YOU PUT IN YOUR NOTICE? WHAT WAS IT LIKE, WHAT WAS GOING THROUGH YOUR MIND, HOW DID YOUR MANAGER TAKE IT?

I was fortunate to have a great manager at Expedia, and he knew I was itching for something different. I had been talking with him about several opportunities I was considering in the months leading up to my departure. So it was a bit anticlimactic when I told my manager I was leaving; he knew it was coming. My team, on the other hand, was quite surprised but supportive of my move.

WHAT ARE YOU DOING NOW?

I’m now the CTO and co-founder of LegUp, focused on using technology to help working families find trusted child care on their journey from pre-birth to the pre-teen years.

LOOKING BACK ON YOUR EXPERIENCE OF FOUNDING A COMPANY, WHAT DO YOU KNOW NOW THAT YOU WISH YOU KNEW BEFORE? ARE YOU HAPPY WITH YOUR DECISION?

I knew that the pace would be different and the priorities unclear compared to a large company role. I didn’t really appreciate though how fast things would move and how many trade-offs I’d have to make on a daily basis. It’s invigorating and what I was looking for, so I’m definitely happy with my decision, but it’s been a learning curve no doubt.

ANY OTHER ADVICE YOU CAN SHARE FOR OTHERS CONTEMPLATING A SIMILAR PATH?

It’s really important to know what you’re looking for and why you want to venture out. It’s different for everyone. For me, it was looking to take more risk and live more. After some coaching and much retrospection, I boiled it down to “the three P’s”: Personal Relationship (with other cofounders), Potential (positive impact for the world and personal payout), and Passion (a sense of excitement and enthusiasm around the space). With this framework in mind, I was clearly able to assess different opportunities until I found a great opportunity with LegUp!

Learn more about LegUp

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