I suggested that Dmitry aim for visible, repeatable revenue before talking to investors. The numbers need not be substantial - even just collecting money from a few customers could be enough if he can demonstrate he has an understanding of the full sales cycle, all the way from first contact to purchase/invoice and on to actual money in the bank. A tested, well-understood revenue model should open doors for him with many investors and help him to get much better terms.
To get to repeatable revenue, Dmitry will need to know much more about how users interact with the site and what they might find valuable enough to pay for. He currently gathers feedback over email from his users and has had this kind of interaction with about 60 of his 1000 registered writers. I encouraged him to try talking to some of these users in person to get even more detailed information about usage and improvement opportunities, and specifically to quiz them about what they find valuable enough to pay for.
We discussed two possible revenue models - predictably, I recommended Dmitry try both to see which works. The first involved helping the members of the writing community to promote themselves and their writing. For example, a publisher may put a book on shelves but leave the author to organise his or her own publicity - book tours, social media campaigns, and so on - and Scriggler could help them to do that. To follow this strategy, Dmitry would be well-advised to look for writers in his community who need this help and to find out what their greatest needs are - which may or may not involve the Scriggler application and current users, as users might need something very different like book-tour organisation. Dmitry was thinking of quite a low cost for this service, but I suggested that pricing for this model could be quite high, as PR agencies might cost thousands per month.
The second model involved helping brands find writers for "content marketing" to help customers find them and learn about their brand without a hard sell. This is a newer idea so Dmitry hasn't explored it as deeply; in addition to discussing it with writers as in the other model, he will of course want to find content marketers at various companies to understand their needs. I encouraged him to consider trials with just a few of the interested brands he finds as he doesn't need very many success or failure stories to prove or disprove the model - the key measurement is whether he can go through the whole process from first contact through to campaign, invoice, and cash in the bank.
In either case, having a working model (even if very modest) is not only likely to help Dmitry find investment, but to help him find the right investors - e.g. if he can prove the brand model works, then an investor with history and contacts in advertising is likely to be _both_ much more interested in coming on board, and valuable to the business in the long term.
I checked in with Dmitry a few months after giving the above advice. He said that they really went for customer feedback, investigating stats on daily comments, publications and just general logins into the system. They concluded that engagement is not high enough and that a solution to this could be to increase digital outreach - two interns are now focussed on this alone. Not quite obvious to me how much this is driven by numbers and how much by interaction with real customers and feedback about what they need - I am hopeful that the focus on engagement numbers is driven by comments from those who might pay for access to a community of energetic, interested writers.