Ask HN: How to minimize career risk from an attempted startup

I am about to ditch my somewhat successful FAANG career to attempt bootstrapping a SaaS business. My goal is to build a lifestyle business, not a VC rocketship, but I still think there is a substantial chance it will not work out. What ca I do to minimize my risk of having lower chances on the job market due to this adventure? What data do recruiters and employers look at to determine if the failed startup listed on a CV is a plus or a minus?

I think it depends on whom you ask.

1. If you plan to continue your entrepreneurial journey, VCs tend to look for what you've learnt from the failure of the business, what would you have done differently etc. 2. If you want to board the FAANG train again, technical details about product, scale, issues etc. would be of interest.

Does that make sense to you?

no offense, but thinking you're going to be able to plan for this is a fallacy that stereotypical faang types easily fall into. there isn't going to be a grade, there is no application and acceptance process for actual success (admission into incubators is not success), and you're probably going to fail. but more directly to your question, every single person/company you interview with after a failure is going to view it differently. it's completely outside of your control or foresight.

but you should do it anyway because living with no regret is no way to be.

I think it'd be good to be prepared to show and explain what you actually did, on the ground to build the business and demonstrate that it wasn't just a side project which you threw up and hoped for the best, but something that you leaned into to make work. If asked, talk about what you learned, what you'd do differently, and how you'll carry those things forward into new opportunities.

As others have said, you can't really control what people will think about having tried and failed to build a business, but you can show them that you put in the work, took some valuable lessons and that those experiences make you a valuable candidate.

> What can I do to minimize my risk of having lower chances on the job market due to this adventure?

a. Don’t quit your day-job until the side-project makes atleast two times your current comp.

b. Work on it for a year; realize you’re way in over your head and pretend it never happened. Line on CV: “took a sabbatical for one year.”

> What data do recruiters and employers look at to determine if the failed startup listed on a CV is a plus or a minus?

Most recruiters will not understand. Data? The data is that you were essentially unemployed for a long period of time; and instead of breaking out of the mold, you came back to the fold — and so you will be judged accordingly.

Employers? Most will think you’re at best a flight risk and at worst too independent-minded to be an employee.

Some will view it as a unique plus if you can show: a. A product; b. Paying customers; but these are definitely the minority and you cannot plan for finding these people. If you do decide to drop out of the corporate grind, your best way back in would be your network. If you don’t have one, you may end up working for boiler rooms at much lower pay.