Thanks for your question.
If things go well the boss will find out anyway, so you may as well assume you will do well and have a conversation with him now. Now we don't know enough about your idea to really advise well enough, but in general I'd try and position it as a 'weekend hobby', and as something he/she shouldn't be worried about.

Also, I really wouldn't worry about the boss doing what you do just because they can. I'm guessing anyone connected with you on social media or networking events could do so too. People are way too busy with their own stuff to allocate enough time and resources to do what you do, nor are they as advanced in the business as you have been, given you've spent valuable time gaining key insights that they couldn't never gain from hacking a version of your business.
Hope this helps. Good luck!

First, I'm a dad and an entrepreneur. Kudos to you! It's a big deal doing this with kiddos.

Second, it's hard to say entirely without knowing more details. But, I won an entire startup competition without my day job knowing (six months). It was completely legal, I just didn't want the hassle of talking through why I was doing something on the side. If you're no legally allowed to, that's a different ball game.

Third, for what it's worth, online customers may not need to know much about *you* for quite some time. You can attend physical events without having to put your name on your site or social profiles just yet. You can blog as the company and fill your 'about' page with company mission and vision info. If the product isn't a consultancy, podcast, etc. you might be able to stay anonymous for longer than you think.

Fourth, there is always a fear someone else could steal the idea. It doesn't happen often though!

Fifth, I would advise waiting until you absolutely *have* to say something - preferably when the company is at a point you can jump ship.

Sixth, keep all your personal files off your work computers. Or, use a password protected partition for all those files. It's just a smart way to operate with this stuff.

I hope that helps! If you want to chat about it let me know. I'm easy to find on Twitter if a phone call doesn't make sense.

Execution of ideas is a big factor...just because someone knows about your idea doesn't mean they can or will do a thing about it.

And even if they do, will they have the energy and ability to execute it as well as you?

You have two choices as I see it:

1. Embrace the public connection between you and the new business ("Yes! It's ME!")

or

2. Keep hidden behind the business name. Center all marketing around the business and downplay personalities. Use your first name only as much as you can ("Derek at JingoText").

Sooner or later your employer is going to find out.

You really don't have any control over what he does. Whether he's angry, supportive or ambivalent, you need to be clear with yourself about what you're doing and why.

How much do you value your business?

If being safe (which is an illusion: your job can be taken away at any time) is more important to you than developing your own business, perhaps you should turn the idea off.

Being self-employed takes guts. And you learn those guts while you do it--I can tell you from my own experience that I am much braver about taking risks, depending on my own efforts for income, and being my own boss, now than I was four years ago. So you don't have to "feel it" 100% at the beginning.

But you should know whether you're committed or not. And if you are committed, then it doesn't matter what your current boss thinks.

Stealth mode allows businesses to temporarily conceal their product, brand, or any aspect of the business, as to not alert competitors of what they are working on until the last minute. The idea is to develop products and services in secret, out of the sight of competitors. And then, enter the market when the product or service is advanced enough to stand on its own and hold an advantage against new market entrants. I believe this is the only way to handle stealth mode.
Besides if you do have any questions give me a call: https://clarity.fm/joy-brotonath