This is a really excellent post on how to go about raising follow-on funding from First Round's Bill Trenchard and Brett Berson.
FirstCapital helps companies raise growth capital funding, and we see a lot of these issues, all the time. Key pieces of advice from this article that stood out for me:
1. Never run a process half-heartedly. You are either fundraising or you are not. Don't get sucked into a series of conversations that never really go anywhere;
2. Inbound investor interest, especially if it is not from a partner, is not necessarily an indication of demand. It is probably just someone doing their job, researching the market;
3. Markets change. Just because your last round was easy doesn't mean this one will be;
4. There are few things more important than your credibility as a founder. If you lose this (eg through overselling) it's almost impossible to regain, and this will kill the process;
5. Research and target the right individuals and the right investors, and then run the conversations in parallel: scarcity, competition and momentum creates demand.
I'd highly recommend you reading the whole article, it's packed with thoughtful, real world advice for entrepreneurs.
Never run an ad hoc process or be half-heartedly fundraising. As a founder, you should either be fundraising or not — and if you are, it should be done with great intention