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Although the question "What would prompt an Internet Mogul (middle aged  man with a sewing machine) to offer an advice column?" has yet to be asked, there is a remote possibility the topic could present itself in a casual conversation.  A hypothetical example where the topic might serve as conversation starter might be as follows:

Imagine yourself (Kindle user) having your oil changed at a local quick lube.  It's hot, crowded and the plastic chairs lack both padding and lumbar support.  Although you have specifically requested the advertised bare minimum service, basically "change my oil in ten minutes and let me out of here", the service tech is approaching with an armload of dirty car parts.  You know the standard spill.  It is simply a miracle of providence that you were able to limp into the oil bay with the condition of those filters, nicked belts, PVC valve and dark fluids.  Take charge of the situation before he shames you into submission for a $89 transmission flush.  Set your feet, stand tall, look him directly in the eyes and ask the question " What would prompt an Internet Mogul (middle aged  man with a sewing machine) to offer an advice column?"

There's a 100% chance that he will have no response.  Take his blank look and non-answer as a point of weakness.  Sit back down in that hard chair, open your Kindle and tell him you will be reading while he puts that dirty stuff back on your car.

There's even a stronger chance that you will ever have to provide a reasonable answer to the question but just in case the simple answer is "Why not?" .  If the short answer is inadequate, there's always the real issue of a real job and travel.  Lots of time on planes and in hotels and far away from a sewing machine provides ample idle time.  Reading an playing the harmonica can only go so far.  Posting insightful but Useless content fill the gap.

A Google search on "advice columns" returns 53,300,000 results.  This number possibly includes 15 actual qualified advice therapist.  One more in the mix to bring the number to 53,300,001 is just not a big deal.  There are more than ample columns for personal, relationship, career, financial, etc.. advice but none for Useless Advice.  Strangedog takes great pride in being a Useless web site, awash in Useless information and proudly claims no credentials for offering any advice other than Useless advice.