I returned to the workforce after failing as a startup founder — here’s my experience.

🌈 Abstract

The article discusses the author's experience of founding a startup that ultimately failed, and their subsequent transition from being a founder to becoming an employee. It covers the challenges faced during the startup journey, the decision to shut down the company, and the difficulties encountered in finding a new role. The article also reflects on the author's changed perspective and their desire to approach entrepreneurship in a way that aligns with their lifestyle.

🙋 Q&A

[01] The Startup Journey

1. What were some of the key challenges the author faced while running their startup?

• The author faced 10 "no's" for every "yes" they received, had to work all-nighters when the servers went down, paid themselves nothing for a year to extend the runway, and went through an early cofounder breakup and legal battle that threatened to destroy the company.

2. What led the author to ultimately decide to shut down the startup?

• The author found themselves looking forward to the next growth experiment failing rather than succeeding, indicating they were burnt out and ready to step away from the startup.

3. How did the author describe the difficulty of giving up on the startup?

• The author described giving up as "hard when you're stubborn as hell (as most founders inevitably are)."

[02] Transitioning from Founder to Employee

1. What challenges did the author face in transitioning from being a founder to becoming an employee?

• The author struggled to figure out where they fit, feeling like their experience matched many roles but not feeling qualified. They felt like there was an "inner circle" that employers were looking for, and they no longer fit in.

2. What roles did the author apply for initially, and what role did they ultimately decide they wanted?

• The author applied to roles like partnerships manager, "entrepreneur in residence", chief of staff, and customer success, but ultimately decided they wanted to be a Product Manager, as they loved building product, analyzing metrics, working with engineers and designers, and talking to users and customers.

3. How did the author's job search process go, and what strategies did they find effective?

• The author's job search spanned 2.5 months and 19 companies. They found that most companies disliked their entrepreneurial experience, but a few loved it. Their strategy was to focus on those few companies and not waste time trying to convince the others.

[03] Reflections and Perspectives

1. How has the author's perspective changed since becoming an employee?

• The author has realized they don't have to choose between an identity as an "entrepreneur" or a "career person" - they can be both. They are now finding a new way to approach entrepreneurship that works around their lifestyle, rather than the other way around.

2. What are some of the differences the author has noticed between being a founder and being an employee?

• The author notes that things move slower as an employee, they question the existence of certain deliverables, and their new colleagues don't fully understand their decision to pursue their own startup. However, the author has never been happier, as they can focus on the things they enjoy (like product) rather than everything else, and they no longer feel the constant stress of being underwater.