**2026 update, you can find my 2.0 crosswords account experiment on Tiktok here.
My pandemic King Lear? Solving crosswords with friends live on Instagram.
Most Wednesday nights at 9:15, for over a year, me and whoever joined my Instagram live stream solved a New York Times Wednesday crossword together. I read the clues, and whoever’s watching would give the answers. It took us about 45 minutes, but we’d get it done. It started small, and turned into something special.
The first instagram story, posted with no expectation
One fateful night, I made an instagram story and went live. And insanely, people joined. At first, we’d get a group of like 5 friends, and then slowly it grew to 50, and before long we had enough to attract the eyes of a real life sponsor!
I worked with an incredibly talented Art Director, Jacqui Bontke to turn my scribbles into a real brand identity. And then we made a ton of fun merch and stickers.
The journey from weird guy posting on instagram to successful influencer was truly bizarre and rewarding. In 2021 when the world opened up completely, Crosswords with Jonathan had our last show. But one day soon, it will return. Check out more highlights below.
