Artificial Intelligence and Amy

Last June, we made a seed investment in, the brainchild of Dennis Mortensen. Dennis is an entrepreneur I've known for several years. Both of us spent time in the digital publishing space and both of us led businesses that were acquired by Outbrain. Surphace, a business that I led from 2009-2011, was Outbrain's first acquisition in 2011. Two years later, we acquired Dennis’ company, Visual Revenue. The technology Dennis and his team built now powers Outbrain VR - a product that combines predictive analytics with algo-driven content recommendations to help editors program their pages. The acquisitions of Surphace and Visual Revenue helped fuel Outbrain’s growth in very different but important ways and now, Dennis and me are part of a very small club. To thicken the soup even more, my partner at SoftBank Capital, Jordy Levy, invested in Visual Revenue out of a previous fund, so the collective ties to Dennis run deep.

When Dennis approached us with his vision for early last year, we jumped at the opportunity to work with him, but reserved a fair dose of skepticism given the grand ambitions of his vision. With, Dennis sought to solve the age old problem of appointment scheduling by emulating a personal assistant, using human-machine interaction or artificial intelligence. Dennis studied the problem and figured out the average meeting consumes 6+ emails before it’s scheduled. We've all experienced the pain and associated inbox noise - something Dennis aptly calls "ping pong".

Person A: Let’s get together. How about Monday at 10?
Person B: I have something then that I don’t think I can reschedule.
Person A: What works?
Person B: What about Tuesday at 4?
Person A: Sorry, picking up kids from school. Friday lunch?
Person B: Let's push it to next week.
Person A: Wednesday breakfast?
Person B: Perfect
Person A: Okay, I’ll send an invite.

Well, after only six months, is well on their way to proving any skepticism wrong. Dennis and the team (including COO Alex Poon, who also worked with us at Outbrain) have designed an AI-powered personal assistant who can schedule meetings and take the entire exchange out of your inbox. For the average person, this can save 100s of emails a month and for busy professionals, many more. The product is already largely machine driven, e.g. scalable, but still incredibly humanistic - the majority of my contacts who interact with Amy Ingram (the default account name that displays when she goes to work) don’t realize they’re talking to a machine. The experience of Amy creates the kind of magic that gets us excited as investors.

Here’s how it works:

  1. A new user grants Amy access to their calendar via Google auth.
  2. New user receives email from Amy introducing herself and asking for preferences.
  3. User replies to Amy's email describing meeting preferences in plain english. Tell her favorite meeting locations, breakfast spots, coffee shops, etc. Let her know when you like to have meetings and times reserved for other stuff.
  4. Introduce Amy via email cc on the first email exchange involving scheduling. She’ll include you on the first few exchanges to provide comfort, but after that, the user never sees another scheduling-related email in the thread until the meeting is scheduled.

I've been using Amy for three months and it's wonderful. Yes, working with her feels a little bit like Scarlett Johansson in "Her" at first, but as a friend recently described, she’s “irritatingly efficient”. In my experience, Amy has proven more efficient and reliable than her human counterpart - who she replaced. Granted, there are some things that require judgement which a human may still be able to do better, but for simple scheduling, the efficiency and predictability of Amy is phenomenal. She always handles meetings the same way and knows my preferences as I’ve defined them. When clarifications are required, she asks me, and when mistakes are made, it’s usually because I wasn’t clear. I’m not the only one who is excited about Amy. She scored an NPS of 68 among early users and a quick Twitter search conveys the sense of magic that early adopters are feeling. Amy is already scheduling 10,000+ meetings per month in a private beta and the goal is to grow that number substantially before rolling it out broadly. In six short months, Dennis and the team have laid the building blocks for something very special that we think has the potential to be a hugely disruptive business productivity tool.

This week, we are thrilled to announce our continued investment in in a $9.2 million Series A financing led by FirstMark Capital. Along with FirstMark, Pritzker and Crunchfund joined the team as new investors, along with our partner on the seed financing, IA Ventures. We're thrilled to be involved and have a front row seat as Dennis and his team show what thoughtful human-machine interaction can accomplish.

If you want to give Amy a try, go over to and sign up to gain access.