I think definitely for the next decade, more of A.I. is going to be around augmenting humans to make them better. It’s going to be around filling in gaps in jobs that are dangerous or boring or things people don’t want to do – Rob May 

Artificial intelligence and its abbreviation “A.I.” can evoke fantasies of sentient overlord robots, HAL 9000, deus ex machina, or sexy operating systems (please).

I admit AlphaZero spooks me a little but outside of games where are we?

It can be difficult to separate hype from reality. Newsfeed cycles don’t help either. Stories circulate with titillating headlines as to what A.I. has just done without context as to where it’s failed.

Regardless we should pay attention because the ultimate goal of A.I. is to not only make machines intelligent – but as intelligent as humans.

Hence my guest, Rob May. Rob is the CEO and Co-founder of Talla, a Boston-based company offering AI-Powered automation for service and support Teams. Prior to Talla, Rob was the CEO and Co-founder of Backupify, the world’s first cloud-to-cloud backup company acquired by Datto in 2014 Backupify was acquired by Datto.  

He is an angel investor in 50 A.I. companies and the Managing Director at Half Court Ventures and also writes InsideAI, the world’s most popular email newsletter on artificial intelligence.

Narrow voice application A.I. has been an interest of mine since my googler days when beta testing Google Home. So I was very interested in talking with Rob not only because of his deep expertise running his own company but his broad exposure to many different types of A.I. forward companies. I wanted the scoop as to what he is seeing in the real world currently, not DeepMind or CMU experiments but what C Corps, LLCs or Partnerships, etc, we’re actually running or launching.

Bear with me as I geek out a bit but hang in as we bring it home on how A.I. might impact your company and your work.

Here are some of the highlights of our discussion. 

  • How he defines and discerns between A.I. and Machine Learning
  • What he sees as hype and the current reality
  • Where he sees A.I. working and where / why companies fail with A.I.
  • His perspective on the near and long term futures of A.I.
  • Measuring application disruption vs augmentation 
  • How companies and people can prepare for broad adoption
  • Where he see most of A.I.’s value creation coming from
  • How he evaluates investments in companies who say they use AI

and much more …enjoy!

Resources / References 


Half Court Ventures 

Inside A.I

The Age of Em 

Manna: Two Visions of Humanity’s Future 


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