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

Have you considered somewhat of a smoother transition? Keep your current job and work extra to get to a point where leaving the FAANG job is a natural next step.

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?

There is absolutely a substantial chance it won't work out - the vast majority of startups don't succeed. In my experience it always seemed to have appeared as a plus rather than a minus though (both when hiring and when trying to get hired).

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.

Living your entire life in order to optimise your CV is something that you will almost certainly regret.

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.

Ask your employer to work Part-Time (e.g. 3 or 4d/w).

That will free a lot of time to prototype and experiment with your SaaS, while keeping a stable income stream. You'll basically an infinite runway to launch your product.

CV-wise, that's even better as the experience you'll get on your side-business (product dev, project management, new techs ...) will add up nicely to your regular job's. There will be no empty line on your CV.

I've been doing this for 4y, taking free time, learning new techs and and trying to launch various SaaS, and my CV would never been as great if I kept working full-time. I'm also significantly happier.

I think that if you have FAANG on your resume and you showed that you attempted to build an entire software company/product that you will be fine.

Have specific milestones and bail on the project if you don't meet them. One major risk is not failing fast, even with a lifestyle business. It's easy to lose a decade with a modestly profitable lifestyle SaaS

Think of it as your PhD equivalent in the business world. One does a PhD not for mere survival, but for the thirst of knowledge, for engaging in stimulating intellectual activity and so on. The results from your PhD probably may not become famous, may not fetch you any big awards and whatnot, but it will mean something to you. It is essential that you aim for some sort of non-monetary returns, perhaps psychological and emotional results, first and foremost (since it's within your control).

If someone looks down upon you for trying and learning, then is it really worth associating with them?

Do a bit of the groundwork first: Build a landing page, attach free tier analytics to it and start sharing it as much as you can (especially with strangers who are your target market).

Reddit is actually a great source for this, just find a subreddit that relates to what you want to do and direct message people who are active on it. Reddit will block you if you send a ton of messages but 2-3/minute should be fine. If you get terrible feedback or if you hate reaching out to people then you know it isn't for you.

I have a one year gap in my Resume where I built and launched a few products, I just list it as 'Solo Developer' and link to the projects. They all failed haha. It is not as beneficial as a year at Google, but it also hasn't been a huge deal.

I would hope that managers at most places use their brain. A failed startup shouldn't be a read flag. They should ask you about your experience with it. In all likelihood, if you didn't make multiple stupid mistakes you would be a string candidate for most jobs because you have experience running a business. At least that's what I would think.

The best way is to make sure you ACCOMPLISH something. I did the same as you and actually got a massively better role after my startup failed. The reason was because I accomplished something that's hard to accomplish.

How about you get a client before leaving? You should be able to find someone to pay for what you're making. If you can't work an additional 10,15,20 hrs per week at a cushy FAANG job and get a client you probably shouldn't leave to work the brutal life of rejection building a new company entails.

In a way, it's a permanent brand you have to wear and some employers may avoid you indefinitely thinking that you may always be vulnerable to the itch to go out and start your own thing. If I'm looking for a dependable programmer the last thing I want is an ambitious entrepenuer.

It shouldn’t matter, been through it before. Just don’t make the failure seem to be your fault.

I went into the startup journey after having a full time job. Now, with around 14 years of experience, it's actually not easy to find a job. Mostly because I'm over-qualified, and most employers are scared and doubtful of someone who says can do or did so many different things and not just "React developer for 8 years". In the end, I ended up removing stuff from my CV to even be considered, but still harder than I thought to go back into the workforce.

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Based on my personal experience attempting something like this, most people will not understand it.

To minimize risk, I'll recommend having conversations with other FAANG people in your network and create a soft back-door.

This is obviously opposite of "burn your bridges" strategy, which is quite popular and may not be your vibe.