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.

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.

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.

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.

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.

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^>

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.

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.

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.

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).

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?