It's actually not that hard. We made waves with national radio ads and meetings with local chamber of commerce members, gov agencies etc. with @reggaesteem (almost dead now).
It all comes down to your approach, and we find merchants were far easier to onboard than casual users, as they are able to pay staff to learn the 'system' in order to reap the benefits of decentralized payments, data/financial security, as well as the promotional benefits of using a social blockchain.
Casual users are easier to onboard in groups of co-workers or friends. The idea of earning money together inspires camaraderie and peer pressure.
We need to enable the experienced professionals within the community. I believe the inherent problem is we listen more to whales than those with the experience to get it done. There are quite a few members who can put a solid marketing campaign together but the feeling is unless they have a high stake or good connections, they likely wont get a chance.
PS: The current hive.io landing page truely sucks, it is now too blockchain oriented for the avg no-coiner who wants to join the 'social revolution'. Steemit at least had that going with Steem.com. Immediately the new lead would understand they are not just looking at the avg blockchain info site but a new world social network, that pays.
Peace