To raise or not to raise?

It's a shame you don't feel the fire in the belly for what you're doing but that happens.
Any Angel or small VC is going to want your absolute commitment to stay with the company. They RELY on your fire in the belly to make the company happen. So, there's a real potential conflict there.

Unless you're "In it to win it", I'd avoid an outside investor. That said, would it be possible to find a potential partner that could "buy in" to the company and ultimately take the helm? Even adding a minority partner that does have that fire and then finding an investor would be a better alternative than you have today.

There are ways to structure an agreement with a new partner that would allow you to get paid over time based on the company's success and with an investor (although there's virtually no investor that will want you to use the funds to pay yourself immediately).

The most important factor is to find a financial partner or investor who shares your objectives. There are VCs that are not afraid of management changes and who are seeking 2 to 4 year exits. The key is how you find your investor and the deal you set with them.

Another alternative is to find and groom a CEO to grow the company and hand over the reigns before seeking the funding. This way you position yourself more as a Chariman or non-executive director and can possibly have your cake and eat it,too.

Your lack of enthusiasm will be apparent to anyone you will want to raise money from. So, that is probably not a viable option.

I think the alternative of bringing in a partner who is passionate about what you are doing is a great idea. That sets up smooth transition for you to get out.

This will still take a while the bottom line is you can stay or leave whenever you want to, but as you have already clearly stated the amount you get out of it will depend on how long you want to stick it out. If the additional return you think you will get is worth it, stick around and make something happen. If not, cash out and move.

Hey there, I have raised a few rounds myself, got my butt kicked on others, and helped raise over $11MM for other startups.

Raising capital is very hard. It's emotionally draining, and it's a full-time job for awhile - the average round takes over three months. Which means... it's hard to do when you're not passionate about what you're doing.

I might consider this approach:

1) Fine-tune your pitch. Make it incredible! Exciting, passionate, and highlight your growth (I/others can help with this).

2) Then, take that pitch to two different audiences:

2.A) A potential COO/CEO/etc. See what kind of talent you can get to phase yourself out.

2.B) A few investors in your network you trust. Try and get a gauge on how difficult this round of funding will take.

You can use that "data" to help inform your decision.

Last note: some investors might actually be happy to transition you out of the CEO role. Not all, but some.

Hope that helps!

You can choose. Have a few millions, be completely free, enjoy the fuck out of your 20s + start a new company or have 10+ millions in 10 years. What would you like more?