There’s been talk of lower priced memberships and per-article pricing, both of which are ways to potentially increase membership while still doing so profitably and without undercutting current subscribers.
But there is another way to grow the bottom line, and that is by offering even more expensive tiers. It certainly shouldn’t be the focus, but Thurrott.com may be leaving money on the table by not at least offering a higher tier. If you look at Kickstarter, Patreon and other subscription-based sites there are often opportunities for people to contribute at a level above the baseline value proposition for different perks. I bet there are readers out there who would pay $100/year, or make a special one-time payment for something special.
Obviously this could devolve into farce (e.g. tandem bike ride with Paul; drop Brad in a dunk tank; have the guys leave you a happy birthday message), but I think the basic premise of giving people a chance to be super-contributors isn’t entirely untenable– especially when you’re talking about a niche audience that also likely contains some very passionate fans.