I just used my WebWhore101 goal to achieve 101 different sources of income to make a somewhat dubious investment.

Tonight is the last chance, supposedly. It’s a $100 minimum buy-in (is buy-in the right word or am I confusing investing terms with casino gambling OH WAIT they are the same).

The relatively low minimum stock purchase combined with FOMO (LAST CHANCE! Tonight!) and the fact that I’m procrastinating on preparing our 2022 taxes (late, but could should still meet extension deadline) made for a perfect storm of ill-advised but probably-not-catastrophic decision-making.

A lot of my “101 Sources of Income” goal is motivated less by money, and more by curiosity and love of learning. Some people think a life well-lived involves lots of travel. Others think it is a life revolving around relationships and social connections. Still others believe it is about living in service. For me, though, it’s wandering around, exploring things, learning bits and pieces of stuff.

And I’ve always been curious about crowdfunding websites. Before “crowdfunding” was even a word, back when I wondered if it was possible to get non-traditional loans for my porn sites through some kind of stock-y scheme; everyone said NO, too hard/impossible to do legally … but here we are twenty years later having seen the scams of cryptocurrency and completely bonkers cult startups like WeWork that literally bilked people out of billions of dollars.

I’m curious about the lines between gambling and socially-acceptable “investing”, and where people draw legal, ethical, and moral boundaries around thrill-seeking, risk-taking, sex, and money. The stories and bullshit people cloak allllllll of that stuff in. Why one kind of thrill-seeking and risk-taking is seen as smart or heroic, while other kinds are viewed as weak, pathetic, or negatively pathological.

Will this $100 investment satisfy my curiosity in these regards? Probably not much. But I’m curious and already time-invested in the particular site offering these options, and the fascination one of the site’s main dudes has with Bob Guccione (Penthouse, Omni) and the investments he has made in preserving and low-key celebrating Guccione’s art and culture contributions. I get the feeling most of the site’s users are not keyed into this aspect of the platform and the ways it straddles some lines between erotic content and very mainstream apple-pie g-rated audience-appealing content in ways I see very few other newish platforms built with user-generated content embracing.

The site also has a really unusual business-model for a bigly-branded mass-advertised platform; it does this very old-fashioned thing of hooking people with the lure of winnable contests with big money prizes … but you have to pay an entry fee, most often in the form of a monthly membership. I’m intrigued by this set-up and the other things they keep throwing at the wall (including these stock options) to see if they stick. I also love the diversity of users on the site where the people contributing content are not the fancy types populating other famous platforms drawing content and traffic from would-be literati snob bloggers and well-oiled influencers.

Will my investment make money and qualify as an actual source of income? I’m guessing I will get my hundred dollars back and maybe a few bucks here and there before the site eventually dies in a few years. But I would be thrilled if it does better than that. It seems pretty unlikely, though; why are they soliciting funds (and rather aggressively, it seems) from their users this many years into their game if they're doing well? Is it not for our actually money, but more for our buy-in and loyalty? If so, will it pay off? Color me intrigued.

Probably the hundred dollars will be a fair price to pay for “research”, as much to dabble with the DealMaker platform managing the investment stuff and making it accessible as for the site I’m investing in, but I would love to find that this business model actually works, confirming that many people are happy to pay a regular entrance fee to participate in something kind of therapeutic and arts and craftsy for a little attention, positive feedback and the much more important hope of winning big.