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Lessons From A $80M Startup Failure

Questions You Can Ask To Avoid My Mistakes

(Read time 13 min 5 sec)

After Uber’s layoffs in 2020, I was looking for my next role.

After some soul searching, I created a goal to become a Chief Operating Officer or found my own company in two to five years.

But I wasn’t there yet.

I saw a gap that needed to be filled in my experience.

I had launched markets, managed markets, managed products, managed small teams, and touched every aspect of the business in my seven years at Uber, but I had never owned the whole thing.

I hadn’t yet…

  • Managed the entire operations department

  • Been in charge of department hiring

  • Reported directly to a founder

  • Had exposure to fundraising

  • Dictated the OKR’s and department strategy

So, my mission was to get those experiences, build those skills, expand that network, and learn from those teachers to make my achievement of COO or Founder inevitable.

The best way to achieve that goal was by taking on a VP, Director, or Head of Operations role at an early-stage startup.

After following the same job hunt process I share in this newsletter and teach in the UpEmployment Accelerator, I landed a role as VP of Operations at Avo, a same-day delivery startup.

The Smiling Avocado

Avo was founded in 2017 by four co-founders in Israel.

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