pics

I actually can't speak to Reich's experience, as I hadn't heard about this before; the only information I could find on it is this Reddit post which states somebody tried to upload his incompatibly licensed photo from IMDb. The citation in this image is to a members-only Game Changer video.

The steps are straightforward and should go as follows:

• Make sure the image you're going to use can be licensed under a compatible license – generally CC BY-SA, CC BY, or CC0 (public domain). If somebody else took it, make sure you have their consent to freely license it. Written consent is preferable if you're afraid it could be challenged.
• Make sure the image is better than the original if one already exists. If you're doing this in good faith, this next part probably shouldn't apply, but: make sure it doesn't violate guidelines on promotion, (superfluous) vulgarity, etc.
• On Wikimedia Commons, add metadata to the image such as the date taken, the author, etc. then publish it.
  • In the case where you're uploading your own headshot which you intend to use on Wikipedia, the description should probably state that you, the user, are also the subject (especially if the author is someone other than you).
• Now to get it onto Wikipedia, you'll swap the current infobox image out for the one on Commons by just changing the string in the 'image' parameter of the infobox template.
• On a technical level you're done, but on a social one, Wikipedia does also require COI disclosures and heavily discourages editing about yourself, so it's a good idea to go to the talk page and clarify that you're the subject, that you changed the image, and why you changed the image (if one existed before).

So to your question: I can't really say, because it doesn't seem like a difficult process, and I don't know how/if Sam Reich's experience deviated from it.

Edit: TIL we have an actual guide for this.