You can’t really compare <i>entrepreneurs</i> and <i>VCs</i> roles, as they are entirely different things. VCs are investors and may or may not have a board role and although they add value in other ways, the day-to-day running of the company is left to the entrepreneur.<p>There are slight variations of this model where you can create an ‘incubator’ of companies which is what was started by IdeaLab (I think they were the earliest tech incubator in 1996) and what the likes of Obvious, Rocket Internet, Science etc are doing.<p>However, in terms of doing 1 startup vs. 20 startups as per your example – if any of them become successful you are going to need <i>entrepreneurs</i> to run the startups in your ‘incubator’ (and you’re going to have a problem even attracting them unless you have $$$) – and <i>you have far better chances of having 1 successful startup than 20</i><p>The reason why you have a better chance of having 1 successful startup over 20 is easiest to explain with an example, so let’s pretend that you want to make $100/day from these startups. You may think that if you have 20 of them that’s only $5/day compared to 1 earning $100/day and getting 20 to $5/day <i>may</i> sound easier than 1 to $100 especially as, you can “spread” out your chances of success and income sources – it’s not. The reason why it’s not is because:<p>Bigger sites make <i>more money</i> – advertisers like to work with large sites because it’s the same amount of paperwork to advertise on a site with 100,000 pageviews as it is for one with 10,000,000 pageviews – which is why advertisers prefer to do 1 ad buy on that 10,000,000 pageview site than 100 deals with sites with 100,000 pageviews.<p>Bigger sites get better <i>deals</i> – when you’re generating a ton of traffic you get great deals from advertisers. Likewise, bigger sites <i>open doors</i> as most companies aren’t interested in working with small sites until they have a considerable amount of users – having 20 sites with 1M users each isn’t as interesting or valuable as having 1 site with 20M users. Why? Well 20 sites x 1M users each = 20M right? NO! Every time a member of one of your sites is member of another – it reduces the total number of users.<p>Bigger sites are easier to <i>promote</i> which makes them <i>stickier</i> after all the average user only visits a handful of websites.