This is basically saying: "You got them hooked, now squeeze every cent you can out of them", which I think is very dishonest advice. There is at least one costumer who won't (or can't) pay a penny more than they are currently paying, and "experimenting with prices" would be like telling them: "well, go away, there's a guy here in line with more dough than you". Given the very-skewed distribution of wealth, this line of thought leads to very expensive services for the rich, and the poor having to leave without them (housing market, I'm looking at you).

Let me explain a bit more. I don't suggest raising prices for early customers who are receiving the same product they signed up for originally. They can stay at the same price, which is grandfathering them in.

More typical though is Customer 1 signs up in 2015 when the product had features AB. Then in 2018 the product adds feature C. Is it fair to raise prices on them? Maybe, maybe not. In this case, I would still recommend today doubling prices for all new customers. You can go back to Customer 1 and say either:

1) we raised prices, but since you are an early supporter you get the current price for life with features ABC (if feature D is added, don't give it to them for free, they have to upgrade to the new pricing).

2) we raised prices since adding feature C is providing more value, but as an early supporter we are going to keep you at the original rate for 1 more year.

Surely that depends what the price right now is. As the cheapest paid version is $1/month, I don't really think doubling it to $2/month would be excessive.

We'll definitely give pricing some thought, you're right that it's probably time to revisit.

Re: the video, actually now that I look back we used a company called xp-studios.com - we just provided the script. I believe it was around $3k but this was back in 2013.

I came to suggest the same. The prices feel way too low. If you haven't experimented a lot with these, I'd recommend trying it. If you have paying customers now, I suspect you could increase new monthly revenue by several multiples.

You mentioned wanting to play with paid ads. I think you'll quickly find that your current LTV is way too low to justify any campaigns (unless your enterprise plan is converting like crazy?)

(Unpopular opinion) Also consider experimenting with killing your free plan if your goal is to increase revenue. I'm not saying you definitely should kill it long-term - just experiment with removing the option in an A/B test and see how it impacts conversions on paid plans. Freemium normally benefits products with network effects. It's not totally obvious to me how your product might benefit from that.

Disagree, he's taking advantage of the freemium model which is probably giving him more chances of getting real users.

They're not suggesting getting rid of the freemium model, but to raise prices of the paid plan.