You have 1.2mm ARR, that's a lot of leverage and you're in a strong position to raise a Series A. Your current investor has no reason to encourage you to take m

You have 1.2mm ARR, that's a lot of leverage and you're in a strong position to raise a Series A. Your current investor has no reason to encourage you to take money off the table, but they also don't have a super compelling reason to discourage it. But of course if you ask them, they'll say "no don't do that." Ultimately the only way to get a read on the situation is to start the raise and see how outside investors really feel about it. But why the rush to take money out now? And why slow walk into Series A? Personally I'd try to couple it with the raise (rather than pre-emptively) because that's when you'll have most leverage against all parties, and you'll probably be able to sell your stake for even more too. So either raise now, or sell your stake later. Once you get two new outside investors, you just need one of them to approve a secondary sale and that's enough leverage to get the others in line with it. Also, you can always increase your salary, or even pay yourself a bonus. Your lack of salary for two years and subsequent revenue increase seems like a good enough argument for why you deserve one. Get your co-founder aligned and pay yourselves some cash...