Reading Brian's post is like reading something I wrote a few years ago with the same honesty, approach, and potential foundation to continue into the future. During the early years of WP Tavern, I monetized the site through display advertising and affiliate links. I had 0 business sense and didn't know what to charge. I went with whatever price seemed reasonable to me and I've since learned this is a common problem of self-devaluation.
There were many threads in the WP Tavern forum discussing options and ways for me to make money. Almost all of them were not created by me but by the community. Some even campaigned to have Matt hire me for Automattic lol. At one point, I took some advice and created a VIP program within the forum. The program was $60 for 6 months while $100 gave you an entire year's worth of access. VIP members received access to a private job board, private forum, content not available to the public, special deals with WordPress companies, etc.
The problem I experienced with this program is the continuous need to provide value to members. This was difficult, especially when I was already spending most of my time writing engaging content for the site. Quite a few people purchased memberships to the program more or less to support my efforts, not necessarily to take advantage of everything the program offered. I launched the VIP program on May 28th, 2010. I closed it down August 31st, 2010.
I closed the VIP program and refunded everyone who joined. That was a substantial, financial hit but I felt it was the best thing to do. I closed the program because I felt like I wasn't providing enough value to members to justify its existence. I was really upset with myself and felt like I was ripping people off. I closed the program without telling anyone I was going to do it before hand. When members saw refunds in their account, they were confused and some of them were upset. Since they just wanted to support my efforts, they'd rather I have their money instead of refunding it. This post goes into more detail on the closing of the program.
I continued to try to monetize the site with affiliate links, display advertising, audio ads during WordPress Weekly, etc, until the effort wasn't matched by income. Eventually this lead to me selling the site.
In the past few years, I think Ryan Imel (WPCandy) had the best shot of monetizing an independent WordPress news/community website. With his developer background and eye for design, he could create things to sell or enhance the site in ways I couldn't with WP Tavern. I thought the idea of an iPhone app just to read the Tavern was a stupid idea. Ryan did it with WPCandy and people paid for it. I thought a physical medium focused on WordPress content was a stupid idea. People paid for it. WPCandy also had a jobs board, a forum, and was executing on all of the things I thought were stupid ideas.
I'll always have respect for Ryan Imel and what he did with WPCandy. It's too bad he couldn't keep it going and the bottom fell out with the Quarterly, a physical piece of WordPress history. Again, a lot of the people who gave Ryan money did so in an effort to support the site and his work, not necessarily for the benefit of advertising products to his audience. Ironically, Brian Krogsgard became a respected voice in the community thanks to his work with WPCandy.
Brian and I have different backgrounds, see things in a different light, and have different ways of dealing with things. A lot of the things I wanted to do to enhance the site or create products required developer knowledge. Ryan Imel had this and so does Brian. That's a great advantage to have. I don't know how he plans on balancing his work at Range INC with PostStatus because everything in his post is aimed towards the site being a large undertaking. However, if he hires the right people to help him out, it could turn into a hell of a resource for WordPress folks.
I also like the idea of PostStatus being sort of like an industry trade magazine, concentrating on the business aspects of the WordPress economy. If there is a niche he excels at, it's this one. He's also got a knack for writing great posts on development aspects of WordPress.
There are a couple of things I hope Brian can power his way through. The additional pressure of having to deliver on a regular basis so that the value of memberships is maintained or increased. The feeling of not doing enough to justify the cost is draining. If he opts to go the way of corporate sponsorships, to find a way to balance those with unbiased reporting/content. I'm almost certain that will be a non-issue. Last but not least, if he sees this not working out, to cut the ties sooner rather than later. I don't think anyone has to tell him to do the complete opposite of Ryan Imel when shutting something down.
As I mentioned when tweeting this, I had a shot and failed, Ryan had a shot and failed, I think Brian has what it takes to make the model successful. Success being long term stability, being around for a few years, growing, increasing value for the membership prices and becoming a heck of a destination for those in and especially those outside the WordPress sphere. That is potentially the largest challenge Brian faces, getting people outside of the inner WordPress circle to join and support his work.
If there is one other piece of advice I can share, it would be to go with his instincts and gut feelings. I asked my community what I should do and ended up with too many ideas or ways to implement them. I ended up in a confused direction of travel instead of just following my instincts.
I wish him the best of luck. I'm curious to see what PostStatus is up to a year from now.