I'm leaving my day job. But my CEO doesn't want me to leave.

I could be wrong, but I doubt he has any desire to invest in your business (and if he doesn't meet accredited investor requirements, you might not be able to legally pull it together anyway).

More likely, he does not want to deal with backfilling your positions and training a new person.

The probability is that he is being selfish, not helpful to you. I would look for some sort of work-from-home or part-time arrangement. Let them "fund" your startup by allowing you to keep a portion of your paycheck, not by actual investing.

Don't count on option 2, either. I've seen many cases where a "super critical" employee leaves with much concern, and 3 months later it's like they never even worked there.

I don't mean to sound negative, just realistic...

The work from home or part-time arrangement sounds OK. He has already hinted at that. As someone else has said, I worry a bit about IP in that case (although I never signed any agreement with my employer).

IANAL, but I don't know that you have to sign any kind of agreement other than you cashing your paychecks and them having a written policy stashed away somewhere.

Note to self: determine if they have any IP policy stashed away somewhere.

The startup existed as its own corporation before they hired me; in fact, they hired me because they liked the startup.

I'm pretty sure he means "work together to keep you here" not "work together on your new project".

Noodle's suggestion of offering to stay on as a consultant for less than 40 hours a week is probably the best suggestion.

I just went through this process myself. It can be tempting to structure some kind of part-time agreement, to continue to consult with your old company, but I didn't do it.

It took me 5 months to extract myself from my old company, I planned it out with the CEO and set a date. After that date, all I've done is answer the occasional question. Now I have complete focus on my startup, and it's been wonderful beyond even what I expected. It's unleashed a whole lot of creativity that was squashed at the old company because my ideas didn't really fit in with the company's direction. I'm totally loving it.

That is some seriously encouraging commentary. Thanks.

True dat. Although now you need to get someone to weigh in where the process backfired on them. Volunteers?

"This is a fairly established startup with a few million unique users"

I cannot understand what is holding you back. Quit your job. No strings attached. Just go for it.

If you have a startup with a few million users and you don't quit your job, who will? This is a no-brainer. Take your chances. Take the plunge. It will turn out good.

Oh I don't know. How is it "taking your chances" if "it will turn out good"? It may turn out bad, in fact, the unconditional odds are against him. Not to be a sourpuss, just being realistic. I think he is quite right to agonize a bit and think his options through for the event that it does not go well, even with millions of unique users. Good risk management...

This is pretty easy: switch from employment to 1099 contracting. Get a master services agreement in place with its own IP clause, which ensures you own your own product, services, and methodology work. An MSA should also establish your ability to subcontract work, or substitute any of your employees for yourself on projects.

Then get an up-front commit on a couple months worth of work.

You have now set yourself on a course to bootstrap the company off consulting work. Total win.

It's quite common that key persons(usually in management/business) stay as consultants for a while, like few months to few years, when they're leaving/boostrapping their own company. The company will have enough time to fill the position and train the new guy and the person leaving can keep stuff running and turn over accounts/information/contacts.

Try to negotiate somekind of new contract. It's good to get a solid contract, say for like 6months, which is renewable or terminated if both parties agree, so they can't drop you easily(you can have some income projections) but they cant keep you forever either, and you can terminate it if it doesn't work out.

what if you went from a full-time employee to a contract/freelance worker at maybe 20 hrs/week? more time to work on the startup, and you'll still have a separate steady paycheck (edit: while you work on monetizing the startup).

Good suggestion, I'll have to think about that.

Then again, the startup definitely has enough work to keep me busy full-time, and taking a 1/2 cut in pay to work 20 hrs a week on the startup is almost worse than going to $0 pay to go as fast as humanly possible.

why would you agree to a simple 1:1 ratio paycut to hours worked? minimally, you need to cover taxes, benefits, etc. that the company was covering previously, so your hourly rate should be higher from that. but since you're the one inconvenienced here, you should be asking for more on top of that.

Good point!

Yeah -- single tasking is probably much, much better than trying to split between two companies at once.

I'd pursue getting the CEO as an angel investor. It provides you with money to build the business but attaches you to only one person instead of an entire company. If you are successful, you can always propose a larger investment or relationship with the existing company as a whole -- and by that point you know the CEO already has a hand in both pots, thus an incentive to facilitate that relationship for you.

A thought: If they want you bad enough and you are in the U.S. or similar, make continued healthcare coverage and maybe some other benefits part of the negotiations, even if you go contract. (+)

Sabbatical? Some companies will offer/support that kind of a time off model.

Guard your IP.

+ I'm not certain this is possible, but I've heard sometimes vague descriptions of such arrangements. It seems to me that staying within a larger pool would be preferable to purchasing independently.

most freelancers include healthcare/insurance/taxes/etc. into their hourly rates by default. not all, but i think its reasonably standard. in the US, that is.

For health insurance, is there a benefit (so to speak) in staying within the former employer, now client's pool, as opposed to shopping independently? I don't know much about this and what is possible. I've heard mention in the past of some people achieving such an arrangement. Whether that information was correct, I am uncertain.

EDIT: I updated my prior comment, above, to better reflect my uncertainty.

yes. it will almost definitely be cheaper in total with your employer (i'm not taking who actually pays -- you, your employer, or both).

going solo, it will be more expensive unless you can get in with a group of some sort. for example, you can join up with the freelancers union and get help with your rates (i think -- haven't actually done the work to see whats cheaper).

Are you implying that by giving up 20 hrs to your current employer, you'll only have 20 left for your startup? If you really think that your startup is going to be successful with you only committing to it 40 hours/wk (in the absence of contracting back to your current employer), you should reconsider your startup.

If you go this route (and you definitely should) be sure to get yourself hired through your startup, so you can use your old company's logo and a quote from your boss on your PR page.

My advice: Get 100% on your startup or don't jump the ship.

Don't fire bridges with your last job-contacts. Keep your friends and be polite with your CEO but tell him you have taken a decision.

Factor Number 1 in a startup is time, if you continue working for your job, you lose a lot of more time in between. You need to be in the position of having only two options: 1-success or 2...success. You need to be hungry for success. Take money from people you know how they are.

pg wrote about the risks of trying to consult and build a startup at the same time:

http://www.paulgraham.com/startupmistakes.html

Look at #18. It's what killed my startup.

I know of a similar case where the company continued to pay 75% of the person's salary and health coverage for half-time work. This worked out pretty well.

Is your startup in an area strategic to your current employer? That presents an opportunity for their formal support but also a risk -- are you certain they'd have no claims on the work you've already done?

Yes, it is. They could offer a lot of promotion, but our biggest challenge right now isn't exposure, it's (no surprise) revenue.

Exposure can be a catalyst for revenue (of course), so that does sound handy.

4) You ask your current employer to match the position and potential financial upside (with far less risk of course) you would be getting at the start up.

How about a retainer agreement? They purchase some of your time each month. This limits your time devoted to their concerns but could also be a distraction from the startup. The rest of your time is devoted to your startup with the retainer giving you more runway.

Any chance your current employer could become a paying customer? Starting off with a customer gives you credibility for capital and other customers.

Retainer--that's not a bad idea. So they could potentially hire me out for X hours per month, and there would be an upper bound on X?

Any chance your current employer could become a paying customer?

Already are, actually.

3

Do you know of any examples where this has been done?

Actually I do and just can't think of them. But I know this is not that unusual.

Chances are you will fail. Even if you do the right things.

Don't mean to be harsh but that's the statistical reality.

Cheers

If you fail even by doing the right things, you are tragic, and I wouldn't call that a failure because I believe in rebirth.

Off-topic: what's your measure of success?