I Almost Left My VC Job for a Hot AI Startup

#1

Post by swedonym » Sat, Jun 28, 2025, 2:06 PM UTC

I Almost Left My VC Job for a Hot AI Startup
swe2vc.com

Re: I Almost Left My VC Job for a Hot AI Startup

#2

Post by swedonym » Sat, Jun 28, 2025, 2:06 PM UTC

I recently found myself this close to trading in my role at the firm for an early seat on a shiny pre-Series A Sequoia-backed AI startup in the consumer space. The opportunity seemed like a rocketship - exciting tech, star investors, that intoxicating “get in on the ground floor” energy. Why on earth would I hesitate? Well, spoiler alert: I didn’t go through with it. In this post, I’ll candidly share why I nearly jumped - and the reality check that made me pump the brakes.

Re: I Almost Left My VC Job for a Hot AI Startup

#3

Post by ednite » Sat, Jun 28, 2025, 2:58 PM UTC

I really enjoyed this POV, it feels like the perfect counterweight to a recent piece I wrote about why it’s absolutely worth quitting when you’re stuck in a toxic environment.

Sometimes leaving is the healthiest, most rational decision you can make. In your case, staying was clearly the right call.

You are correct that every “shiny” opportunity is worth chasing, especially when you’re already in a good place. The impulse is more FOMO than genuine purpose.

This kind of honest self-reflection is refreshing in a space where the narrative often defaults to “if it’s risky, it must be brave.” Sometimes, staying put is a brave choice.

Thanks for sharing, and well done.

Re: I Almost Left My VC Job for a Hot AI Startup

#4

Post by swedonym » Sat, Jun 28, 2025, 5:01 PM UTC

ednite wrote: post #3

I really enjoyed this POV, it feels like the perfect counterweight to a recent piece I wrote about why it’s absolutely worth quitting when you’re stuck in a toxic environment. Sometimes leaving is the healthiest, most rational decision you can make. In your case, staying was clearly the right call. You are correct that every “shiny” opportunity is worth chasing, especially when you’re already in a good place. The imp…

Thanks for the kind words! Would love to read your piece too if you want to link.

Re: I Almost Left My VC Job for a Hot AI Startup

#5

Post by ednite » Sat, Jun 28, 2025, 8:33 PM UTC

swedonym wrote: post #4

ednite wrote: post #3

I really enjoyed this POV, it feels like the perfect counterweight to a recent piece I wrote about why it’s absolutely worth quitting when you’re stuck in a toxic environment. Sometimes leaving is the healthiest, most rational decision you can make. In your case, staying was clearly the right call. You are correct that every “shiny” opportunity is worth chasing, especially when you’re already in a good place. The imp…

Thanks for the kind words! Would love to read your piece too if you want to link.

Work in progress since I'm new to blogging.

https://mindthenerd.com/how-to-know-its-time-to-quit-your-jo...

Thanks for asking!