There are 3-5 healthcare specific crowdfunding platforms - I would start there.
-MD

Never. If you go into a startup with any other mind-set than your going to make it work "no matter what" you will never survive the grind.

Having done over 35 different financing rounds over 7 companies I've built in Silicon Valley - you should be giving up 15%-25% dilution in each round with a plan to never raise beyond a Series-C.

Investors get equity for money invested, don't start doing "special deals" or it could poison the well for future investors. If you want to "slightly" sweeten it for a truly early investor , then put them on your advisory board for 1/4 a point equity ( vesting over 2 years). Then they have to deliver some value for that equity.

-MD

The realities of media and publishing are such that it requires massive audience to effectively monetize any content.

It's awesome you guys have built up 25-50K in visitors monthly , but realistically the cost of actually building a 10-15MM unique user audience (profitable) monthly is WAY out of the range of possible for most people/start-ups.

Your sweet-spot and skill so far has been to CREATE CONTENT, and arguably content that a group of people (25k-50k) want to consume.

You will need to look elsewhere for audience - you need to syndicate your content and get paid by larger trafficked properties who are looking for solid programming around specific topics your covering.

This is a very real and tangible way to create predictable revenues month-2-month from your publication.

Happy to give you examples.

-MD

Likely you should only be getting 1-4% max as a CMO in a tech start-up.

Pivotal Tracker, no question.

To be an entrepreneur successfully is essentially to be a great communicator and motivator of people, to identify great opportunities and relentlessly pursue them while enlisting other smart people to join you in the adventure.

- I learned more about sales, human psychology and human nature from selling cutlery door-to-door in high-school than just about anything else ( i know sounds crazy)

- The basic notions of how to convince, motivate and "sell" people will apply no matter what technologies come along - so these are crucial

- But if you don't have a strong command of basic technological tools necessary to build a business, the struggle will be harder (email, CRM, CMS, Demand-Gen, Analytics, and the world of software development - Lean, Agile, Scrum, etc)

99% of the time Start-ups fail because there is no tangible "market" for what they are creating...this is why it is SO important to validate that the market demand truly exists and can power a business. I see over and over again this is the mistake a HUGE number of entrepreneurs make in the first 90-Days. You have to be diligent about testing your hypothesis and quantifying market demand - before you tae a single step.