I'd not heard about this before. Admittedly I only knew him from his cute anecdotes about early Windows development. Did a cursory search and I found this thread on Reddit: https://old.reddit.com/r/linux/comments/rb2xzk/dave_plummer_aka_daves_garage_former_microsoft/

There's a pretty interesting comment by a user called Kefim_Wod, I'll quote it here so you don't have to visit that shitty site unless you want to.

TL;DR I don't trust what that guy says anyway.

I really enjoyed his youtube channel until I found out about the business practices of his earlier company SoftwareOnline.com, Inc.

His company was sued by the Washington State Attorney General's office in 2006.

https://www.atg.wa.gov/news/news-releases/attorney-general-s-office-sues-settles-washington-based-softwareonlinecom

Here is an excerpt:

The defendants agreed to pay $400,000 in civil penalties, with $250,000 suspended on condition of compliance with all terms in the settlement. They must also refund consumers who have filed complaints and pay $40,000 in attorneys’ costs and fees. The settlement terms prohibit the defendants from engaging in the following practices:

• Inducing computer users to install software by misrepresenting that the user's computer is at risk for crashes or privacy and security invasions.
• Marketing its InternetShield software by means of a “free scan.”
• Using “buttons” in its advertisements that do not function as the user would expect them. For example, the X found in the corner of a window is normally associated with closing the window and should not open another ad.
• Installing software on a user’s computer that causes multiple pop-up advertisements when the user tries to close out of advertisements.
• Failing to provide a functional uninstall option for removing all software files.
• Failing to obtain a consumer’s explicit consent to purchase a product or a service.

Direct links to associated court documents: SoftwareOnline.com Complaint

SoftwareOnline.com Stipulated Judgment & Order

You can also find them at the bottom of the webpage I linked earlier.

Here is an article from 2009 that mentions it.

He greatly downplayed these events in his book but I'm taking his word with a grain of salt.

I freely admit that I developed a bias towards him after realizing he is a multimillionaire. Learning about that in combination with the information I detailed above really soured my perception of David.

I have the belief that more often than not very wealthy people are wealthy because they have taken advantage of other people to obtain that wealth.

I wanted to give David the benefit of the doubt because I really enjoyed watching his youtube channel but one google rabbit hole later and I felt like my belief was reaffirmed.

Also, the post includes this image, which... I mean it's certainly a take.

He seems like a M$ grifter. Big shocker.