Silicon Valley entrepreneur and start-up veteran - Founder of 7 killer tech companies since 1995, 3 acquired, 1 IPO - active advisor and angel investor in big ideas and passionate teams
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.
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.
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.