Welcome to another episode of Brands & Outliers, where we survey all of the brands moving the culture of their categories forward, and point out the outliers that give us a signal of the future to come.

There were a lot of interesting brand names and developments this month, but they all pointed to one theme: brands are getting comfortable playing with (un)reality.

Our biggest discussion was around the grief tech brands that have been around for a while but are really starting to gain traction now that AI is an accepted force.

Grief tech brands promise to never let our loved ones die, but they also rob us of the very grief that helps us grow. Experiencing death makes people more open to life and brings the living closer together.

It begs the question, will we let the individual escape the pain of loss, even if it means potentially more pain for the group?

In the shallower end of the (un)reality pool, we have brands like J.Crew and AI Garage Sale test the limits of authenticity.

And it’s a good time for that, too, because being ‘authentic’ (this year’s word of the year) once carried a moral charge in its meaning, but perhaps now has become detached from any moral connotation. Etymologists call that expansion of meaning semantic broadening, and it’s been happening a lot in our language lately.

Here are some more highlights from our discussion:

00:26 Splintering Authenticity

• The definition of the word “authenticity” is morphing yet again, and brands like J.Crew and AI Garage Sale are cleverly moving the line between real and unreal

13:31 Reshaping Ecosystems

• Brands like Thales Alenia Space, COBOD, Neighborhood NYC, Haven Co-living and even WalMart reveal how our most important spaces are getting smaller

26:00 Customized Self

• Grief tech companies like Replika, HereAfter AI, StoryFile, and Seance are trying to get rid of the pain of death altogether, but we debate whether that’s what society is really asking for right now

39:25 Chaotic Masculinity

• On one side we see muscle dysmorphia and hunters who won’t wear pink even if their lives depended on it, while on the other side people like Tony P. practice “Vibrant Masculinity”. Masculinity is in its messy middle phase.

P.S. The short animated film I reference is ‘World of Tomorrow‘ (2016).