>"However, I'd like to try to convert them into a paying client for a product that we'd discussed nearly 2 years ago but haven't implemented (it's been effectively killed)."

Cross that bridge when you have a working version 1.0. A heads up might just cause the project to revive. And if you pivot after telling them your plans, you may leave them hanging.

Most importantly, don't make your business model dependent on having your former company as a customer. The most sincere intentions to funnel business towards you may go unfulfilled, even when the benefits of working with you appear obvious. Don't kid yourself, you are a potential competitor.

My advice is to leave on the best terms possible and consider your former employers as part of your business network. Call and go to lunch once a month or so. It's the social relationship that will have the largest payoff in the long haul.

Good luck.

Don't tell them what are you going to do. They will most probably hate the idea of becoming your customer, at least at start.

So just don't do it for the sake of good relationship with this employer.

Also a lesson of being independent which you know already: you don't have to excuse yourself. Do your stuff and move on.

Just say that you're going to work for yourself, feel free to hint that it might be in the same domain.

The point at which you are leaving isn't probably the best time to look for business. Just try to leave without burning bridges, which usually means saying very little.

This is the best job I've ever had and I think everyone there is awesome. This should be a mutually beneficial move for everyone so I don't think burning bridges will be an issue.

An alternative approach previously posted on HN:

http://www.expatsoftware.com/articles/2007/02/two-weeks-vaca...

I quit the best job I ever had. Honestly, I regret it still.

really? any more details on this? We always hear stories about people being happy about quitting their job and how they should have done it earlier.

What did you quit for?

I quit because I moved to Italy for 2 years. That was 4 years ago. I miss the job and the people. I would recommend taking a 'leave of absence' before quitting.

I've never done what you did, but props to you because you're doing something very entrepreneurial and I love it.

I don't think you should sell your idea before you build it. Tell your boss about your ambitions to do a startup, and how you saw an opportunity that you believe is very promising, which is the reason you are quitting.

Tell your boss that you always looked up to him, and ask if you two can stay in touch and ask him for some advices for later. If he replies affirmatively, stay in touch, and exchange Emails from time to time, and then when your product is available, ask him to dinner and pitch it to him.

If he replies no, then he's probably not too pleased with your leaving, thus it wouldn't be a good idea to pitch anything. Save it for later.

Best of luck man!

When I left my last full-time job to return to freelancing I walked in on a Monday morning and gave my two weeks notice to the boss man. I went in with the goal of trying not to piss them off and in the process turn them into a client/customer. Similar to what you're angling for from what I can tell by your comments.

So two tips:

- Make sure you're ready. I knew going in, just like you feel you do, that they would be open to my plan. A lot of the time leading up to giving my notice was spent making sure I was right. I quite literally spent three months getting the balls to jump ship and making sure I was pretty confident I would come out with a client.

- For the love of God, play it cool when you tell them. Try and remember that you're quitting a job and not making a sales call. I wouldn't lead with your plans until they ask. During our conversation about the transition, the chit-chat slowly worked towards what they should do when I was gone. That's when I threw out that they could hire someone else full-time or take me on as a contractor for the technically heavy work and dish out the rest to existing employees.

The only thing I find worrisome about your scenario is that you're apparently counting on them buying a product that doesn't appear to exist yet. They can say "Sure, great idea!" on the day you leave and then, months down the line when it's time to play ball they can act dumb and say "No thanks, baby. That was just pillow talk."

I feel like you might be putting the cart before the horse a bit here but I wish you the best of luck.

If you're a valued part of their team your boss(es) are unlikely to be as excited about your new adventure as you are.

Fine to say you're leaving to pursue your own thing, but it's not the time to be offering anything other than help in finding or training a replacement and making the transition easy on them so they look back at you in the most favorable light when you do approach them down the road.

Personally, I wouldn't try to negotiate anything. Build your product and let the strength of that product do all the talking.

Actually, if I were to negotiate something, it would be the possibility to do consulting work if I needed more money while building the other business.

I've never done this, so take my advice with a huge grain of salt. But some ideas that come to mind:

1. ask them to invest in your startup and take an equity stake.

2. ask them to partner with your startup and do some joint marketing stuff (if your product is truly a complement to their product.)

3. If any engineering effort (on their behalf) is needed to make your product and theirs interoperate, try to negotiate something where they agree to implement that, so you can fully leverage the "complement" position when you market your product. Not sure what you'd have to give up (if anything) to get this, but it might be worth pursuing.

Why quit? Why not try to do the 4 hour work week approach, by working a couple of days a week at home. Then, begin building your product. Once you have a sellable product, then let them know.

Don't burn any bridges, try to be as friendly as possible and maintain connections. You never know when they'll help in some way. Best of luck!

Don't burn a bridge.

Get a bunch of credit cards, preferrably ones with no/low balance transfer fees. Unless they bite and buy your product, you have no idea how long you're going to be without income and getting more credit while building your startup is hard.