Ask HN: How to minimize career risk from an attempted startup | Hacker News Reader

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

24 pointsthw659730 comments

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?

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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.

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?

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.

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.

How do you get around IP ownership issues? I believe FAANG company contracts claim ownership of any IP you develop while employed. Are these not really enforceable and can be ignored?

Not in California, no. It’s why the tech industry exists there and not (as much) in eg Texas.

California has a bunch of laws related to labor ( section 96, section 2870 ) that have the effect of making it easy to start a company on your off hours

IANAL

In most jurisdictions these are not enforceable if the work is done outside of work hours with no company resources. So make sure that you use your own devices, own accounts and so on. There can also be concerns if the products are related (as you may be benefiting from proprietary knowledge).

Of course it is a good idea to confirm with a laywer who can give you a good answer for your situation.

> 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.

Thanks, i appreciate this answer a lot. A) makes sense but I am a bit worried about IP issues?

The point about the network is a great one to keep in mind.

Ask your manager for a waiver, and an invention assignment on your side-project.

It’s not a business; but a side-project (right now) — assuming it’s tech-related. If it’s a non-tech business, where you’re not generating IP, even better.

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

This advice doesn't really apply if you work in FAANG. You generally give up the ownership of any IP you create while under their employment, at least in my experience.

This answer is completely nonsensical. I wonder if it's a satire, especially the last line? I have never once met an employer who grilled me on gaps in my resume and if the question did come up, most were positively surprised that I took a jab at something risky and came out better in the process. In the industry where starting up is so commonplace, I have hard time believing even a corporate company weighing it too much against a candidate.

My close(ish) confidants in my industry will be understanding; and those outside of my inner circle will be polite and cordial about it; but behind closed doors people will judge you, and use it against you.

Perhaps we simply run in different circles.

If a company is going to judge me in that way then I wouldn't want to work for them anyways. Would be like dodging a bullet for me.

Maybe I do run in different circles too. I have only worked for small companies where upper management knows me and values me. I'm not just a faceless employee and I wouldn't have it any other way.

Your reply is basically risk averse and too pessimistic to ever run your own business, if any business owner listened to your advice, they would have never started any business. Big portion of starting a business is risk taking, if you are the type of person who can’t quickly adapt, need your typical coffee in the morning while taking the same commute route, then starting a business isn’t for you, and that’s ok, not everyone is meant to anyway.

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 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.

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.

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.

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.

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?

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.

I might read this differently.

Perhaps an ambitious entrepreneur may be better able to understand what drives business value and translate that into architecture + code?

It may not be a years-long engagement, but certainly the experience brings value.

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).

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

Fwiw i completely agree. This whole scheme is about more than that, but I am interested in derisking.

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

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