Figuring out what’s next after shutting down your company

Gillian O'Brien
10 min readJul 20, 2020
artwork by Ashley Olinger
  • Our last story about shutting down Cherry / fundraising during Covid got a ton of great feedback.
  • Now, I’m sharing a follow up piece about figuring out what to do after your company has shut down.
  • I am a non-technical person and this piece will reflect that perspective

My co-founder, Emily & I made the decision to shut down our company at the end of April. At the time, figuring out “what’s next?” was a concern, but my thoughts and feelings were unwieldy. I didn’t know where to start. I had been Cherry’s CEO: I didn’t just “touch” all parts of the business — the business was me, and I was the business. It was my identity. So where could I go from here?

I soon realized that these concerns were not unique to me as texts and emails from my founder community started to trickle in. Each of them — for one reason or another — were also moving on from their Founder roles and trying to figure out the answer to the same question I was. “What’s next? What now?”

When I don’t have a clear understanding of something, I find it helpful to survey others to build out my own opinion. Some people read books, some people meditate — I like to talk to people. 🗣️

Below, I detail the 4 stages of conversations I had, using my network to ultimately understand what I wanted to do next with my career. I think this article will be helpful, not only for ex-founders, but anyone who is in the midst of a career transition.

👨‍👩‍👧‍👦 Stage 1: Friends & Family

The first people I spoke to were my strongest, warmest connections: friends & family. I shared the news that Cherry was going to be shutting down, and had casual conversations about what the future might hold for me (what roles might I enjoy and be good at?) Here’s what I heard most often:

  • 👩‍💻 Founders typically go into Product Management roles
  • 💨 Founders typically don’t want to join other early stage cos because they are burnt out
  • 🔭 If you’re unclear on your desired role, look at interesting companies and analyze where they may have skills gaps you could fill or take a leadership position in

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Gillian O'Brien

Accelerator Partnerships @ Pilot.com + Venture Partner @ OCVC | YC alum | former Chief of Staff | NYU grad | gillianroseobrien.com