Ask HN: Bootstrapped business is good but slow growth. Should I raise money?

Video's are awesome and seem to really help. Glad they are already working well for you.

To your other point, I have trained my wife to handle our non-automated billed clients and I have outsourced all the other details like Accounting etc. It is amazing how much that frees up time and really does not cost much at all. I also use an online accounting system that is integrated to our products/services so that when a client purchases it is automatically added to the accounting system and so it removes the need to do bookings etc. The accountant than picks it up from there and does their thing and keeps everything straight for me. If you haven't already done that it may be worth your while to go there. Since you are using Wordpress there are existing integrations to QuickBooks, even if you don't use it for accounting today it might be worth moving to it and buying one of the plug-ins for like $100.

We just built a subscription service website for a client (they do online training with videos and quizzes) and they wanted it in Wordpress, so we utilized Woocommerce, Paid Membership Pro and a QuickBooks plugin that basically allowed us to write a very small amount of code (for that part) but let them have a fully integrated solution from signup to purchase to accounting. Just a point, not an endorsement for any of those products, but damn it works and it was way cheaper than a fully custom solution for them.

Lastly as to hiring someone, since you are in a more expensive part of the country, you could train/hire someone in say the Southeast or mid-west where salaries are a bit lower. Also, if you don't need a developer type to do the demo's, then you can likely find someone for a pretty reasonable rate to help you get people signed up.

You're making enough you could hire an assistant to handle some of the support, inquiries, billing/accounting so you can focus on demo's and growing . . . support would probably be the first thing to outsource . . . setup a google doc outlining typical questions/responses . . . so it's pretty straight forward and have them send something more complex on to you to handle . . .

That will free up some time for demos, etc.

You might get a bump from conversion optimization, reducing churn, etc . . .

Could you go to 4 days per week at your day job . . .

Start doing one demo call over lunch a few times per week . . .

I think there are lots of less expensive ways to gain more time/revenue vs. losing equity.

Good luck scaling your SaaS.

agreed. Some investors can be needier than your neediest customer, and worst case, you can always fire a needy customer...

A salesperson with connections in the relevant industry might even consider doing it for commission plus vesting equity only with those numbers.

If you feel that it's a business that needs a big development investment or push by a sales team to fully realise its potential or stave off competition then by all means go for a significant level of funding, but it would be a shame to give up control of your business for just enough angel money to look after your living costs after you've done the hard bit of getting nearly there