Ask HN: Have any of you quit your job to explore startup ideas?

Figure out what you want to do first.

Even if you later pivot that’s fine, but you need direction, otherwise you’ll flounder along until your funds runs out.

Many years back I saved up over one year of runway, quit my job and started working on software tools I wanted to write. I had a clear vision of what I wanted to make and successfully executed on it - and even though those tools still brings in income today, it was never enough to support me financially and so I branched out in to contracting and then for the last few years have gone back to full time employment.

Most startups fail. Without knowing what you want to do, how will you know what to execute on?

Otherwise it just sounds like you’re sick of your job and just want to do something else - that attitude won’t get you far in startup land.

That said, AI is hot right now so maybe you could still raise a 2M seed round anyway.

Thank you for sharing this! Appreciate your advice. Even though AI is hot, I think, raising a 2M+ seed round in the current market still requires having a prototype and some paying customers (or LOI), especially for the first time founders. At the end of the day, the goal is to build a strong business so your earlier point about having a clear vision of the initial product before jumping ship makes sense.

Yes. You need a clear focus and direction. Although a 3-6 months break is more than enough to find out if you want to start a company or just want “more” free time to experiment with technology ideas. I think I am more in the second camp.

Before you jump ship, read the book "The E-Myth Revisited: Why Most Small Businesses Don't Work and What to Do About It." It will give you a very good understanding of what a business is about.

The old proverb, "The grass is always greener on the other side." Is absolutely true. Don't let it discourage you. You just need to be ready for it and act on the challenges. As a techie you are used to finding solutions to challenges so you should be able to deal with the business issues. They just happen to be different when you start a business.

Thank you for the book recommendation!

I have been trying to "bootstrap" various things for at least ten years, depending on how you count it. I've been able to scrape by, and on a few occasions that was at least partially income from the startup attempts. I got used to being poor. Moved to Mexico for awhile.

I never tried to raise money though and always have worked alone so that probably doesn't apply to your situation.

But I was probably 8 years ahead of the game in terms of remote work. Never have to commute. Don't even own a car (technically can't necessarily afford it).

I do have to take programming contracts routinely but I don't try to get high paying ones. And in between I can spend 30-40% of my time working on exactly the projects that are interesting to me using my preferred approach.

Luckily I don't have a kid or anything.

I don't like being poor that much but I don't have to deal with office politics, commuting, high-pressure projects.

Sounds like you’ve found a work-life balance that are you happy with. Thank you for sharing!

I've sort of been in a similar position in the last 2-3 years. I jumped ship because i got tired of an older career where i spent 15 years, hoping I'd get into consulting and work on startup projects I like. I'll be honest and say it didn't go as planned and sometimes i wish i didn't jump ship that fast even though i am a very calculating individual. To be fair though, if you have a very long financial runway and you got a very strong support system, both of which i didn't have, your risk might be less. But the risk is there.

Thank you for sharing this! If you were in the exactly same situation as you were before you jumped ship, how would you handle it now?

Really tough question because I am still finding out the answer myself. A lot happened in two years. A couple of observations though: - I spent 1.5 years after jumping ship exploring different audiences and problems i could solve. It might help if you have a rough idea before you jump ship because you're burning time and cash. - Do plan for things going wrong. In these 1.5-2 years I had opportunities and partnerships. Some of these were with people I have worked with before and I thought we had really good synergy back then. Most went sideways and put me in a financial position worse than when I initially started. So plan for this eventuality but don't adopt a pessimistic outlook. - Marketing is a huge part of the journey. I discovered that the hard way. I overestimated my PR and network which was too niche and wasn't as beneficial as I thought in my new focus area. As a 41 year old with 15+ years in consulting and , I found myself having to reintroduce myself to a market that knew nothing about me and I was as good as the guy who just graduated or spent only 1 year at a big brand firm. You don't survive on marketing alone but it's the number one driver of value perception. - If you're under pressure, you'll make emotionally charged decisions and your emotions might blind your ability to reason through a decision. In general, the more pressure you're under when you're making the decision, the more you should increase your financial runway. So if in normal circumstances you'd make sure you had 12-16 months of runway, multiply that by a factor that represents the additional risk.

Do a personal cost benefit analysis or SWOT analysis. How does it look like? Is your tenure at Apple a + for your future network and vertical? is marketing the forte of one of your partners? What if things go wrong and the partnership breaks? Do you have enough financial runway? What if you burn too much cash too fast? Is there a side kick you can rely on to make extra money if you have to?

In no way is this comprehensive and I am still figuring things out. Definitely made mistakes on the way but It's not always this bad. I started with a very disadvantaged position. I jumped ship because we lived through a local financial crisis as well. People took advantage of that. Make sure you have leverage on the negotiating table.

Hope it helps

Yes, this is very helpful! Love you suggestions to do a personal SWOT; and factor pressure/stress into personal runaway.

Thank you!

I have a small saas, running for a decade. It makes about a quarter of a salary. I got on an accelerator programme and left my job to grow it. It didn't grow.

I tumbled back into employment, in another field, and love it.

Ny advice would be if you and your friend are two Woz's go for business acumen. A guy on my accelerator programme wanted to make millions and he did. The tech lovers, do gooders and dreamers, not so much.

Thanks for the advice! Agree, we, as tech lovers, tend to focus on the tech more than the business/sales side of things.

I've basically never had a 'normal' job on someone else's payroll (with 3 exceptions over ~40Y). I've always been noodling around waiting for the next idea and consulting around various start-ups.

WARNING: this approach has not made me a billionaire, YMMV.

I am solvent, with a paid off house, savings, a family including two happy teens doing well at school, and have just started in academia FTW... B^>

Thanks for sharing this! Great to hear that you were able to stay self-employed for that many years!

I left the same company after 5+ years ( 6 years ago ) with a few goals -

1. Spend time with family ( parents )

2. Work on a side project

3. Travel

4. New language ( Spanish )

5. Learn something new ( tech and non tech )

I am very happy with 1,3,4,5. ( ongoing )

Regarding 2, I worked on making a no code platform for Voice apps and had a working demo/app but the market was just not ready and it still is not … Next I tried making some simple web apps - but no success financially. I keep on experimenting with technology so I still love my current state of affairs.

My personal learnings/experience (also from YC Startup School online ) is that you need to have some form of demand/audience before building the product for the consumer space. My friends in the Enterprise space seem to have much better luck.

PS: The fruit company is pretty strict about moon lighting (speaking from experience of a very good friend ) so just be careful about that aspect if they find that out while you are employed. I left in positive terms, in-fact a week back my boss mentioned to let them know when I am done with everything and would like to be back.

Thank you for sharing your story! Have a couple of questions, if you don’t mind sharing a bit more: 1. How are you supporting yourself financially? Are you consulting or living off you savings? 2. Based on your friend’s story, do you have any tips on what not to do when trying to moonlight?

1. I am primarily living off my savings. However, I haven’t had to sell any investments for expenses during this period and they have likely grown ( as per Mint.com ) I don’t actively track my investments ( I have vested stock from the fruit company + use robo investing ) so I am mentally free to enjoy other things without worrying about market volatility … I think my average monthly expense ranges from $1500 - $2500 depending on the country. A lot cheaper than a Bay Area down payment + plus so much time to do anything. Also unmarried and no kids.

2. My friend ( at Fruit Inc ) was working with a undergrad friend from the East coast on a side project. The other friend posted a Craigslist ad needing help on the project and mentioned my friends credentials on the posting. Somehow a recruiter found out about it and so my friends VP called him … that he can’t do so and so, and that the fruit company owes everything and he needs to turn it all to them, and he can be terminated etc. And even after termination they will come after him. Long story short, he stopped working on the project and he was NOT terminated but he did eventually leave to a different company. (For context: the project my friend was moonlighting on was not some cutting edge secret or some hard problem )

Bottom line: If no one knows about your project you are fine. And if you decide to leave the company and work on your idea … might make sense to ensure that the start date of the code etc looks a little after your resignation.

Happy to answer if you have any other questions

Thank you for such a detailed response - really appreciate it!

regarding (2) did this happen recently? or years ago? I've heard the culture or policy around this has "changed" but that could all be BS.

If you remember Flipboard, Evan Doll was in the iOS team and also taught the CS183 at Stanford. As per his LinkedIn as soon as he left, the same month he cofounded Flipboard although the app was released 1 year later.

I have a few coworkers from my team that cofounded companies and they too have 1-2 month gap after they quit and they all got funding :)

It was around 2011.

I don’t think the policy changed as per se. It’s just they found proof of him trying to hire a part time help.

I had a co-worker around 2013 ish who just wanted to blog and put personal projects code to GitHub. It was not recommended and needed VP permission … basically a hassle.

i wonder how this stuff is dealt with during hiring conversations like when you have a project already …. or how acquihires happen

I founded three startups, raised several VC rounds, and I'm ex Vmware, Palm, Cisco.

For the past three years I'm in the API domain trying to solve hard problems in the space. Sometime being an insider helps you come up with new ideas quite fast. I recommend that in addition to being in AI tap into other domain experience. Otherwise, it is quite possible you may end up building a small/niche feature missing in a large platform and end up in a tight position in terms of raising funds, growing business, and selling your startup.

My new startup focuses on AI-Powered API Performance Testing. We enable startup CTOs deliver High-Performance APIs with our self-learning platform to stop churn and win 3x upsell.

https://www.perfai.ai

My recommendation is to not leave your job until you have a concrete and validated idea. You will be tempted to do it earlier because of "all the extra time" but it's a trap. You will benefit from the pressure of keeping it as a side thing next to your main job.

Having a clear value proposition and developing a unique insight is almost certainly not enough for securing funding. Doubly so in this environment (exceptions like Mistral AI exist, but I wouldn't bet on that). Build an MVP, get some traction (aka paying customers), prove out your value prop. I don't want to be too negative (trying to do something similar in fact!), but there's definitely some real upfront work and hustle required before you can start even thinking about measuring successes.

Agree, developing a value prop. and insights is necessary but not sufficient.

If you have the cash and the time, I’d say it’s pretty low risk to give it a shot. With AI@Apple on your resume, you shouldn’t have a problem finding a new job (possibly higher paying) if things don’t take off in your business venture.

Set yourself a deadline though. If you’re still “exploring” after 2 years, your employability will start to decline.

Edit: also, remember that it’s always better to regret having done it than to regret not having tried.

Thank you for your input!

I am exploring my startup idea after being laid off. I have no actual idea, but it looks like I may be the first to a fully functional prototype of decentralization. I don’t mean Web3 or blockchain. I mean no central artifacts of any kind. I have one last step to complete before the prototype achieves full Zero Trust conformance (as much as a non-hardware solution can achieve).

Thanks for sharing! Good luck on your journey!

You should probably try something in the advertisement space ,there has not been much innovation in this space.

I just quit . God bless me

can you describe what it is about your daytime job that makes moonlighting difficult?

So far it has been challenging to find time and energy to explore ideas and do costumer development after 10 hours at work and spending a couple of hours with family.

Could you reduce to 24 hrs per week? That would be 3 full days out of 7.

so there is no work life balance at the fruit company?

Depends on the team. Most of the times WLB is not bad.