Dennis Mortensen – Co-Founder & CEO,

Dennis Mortensen is the co-founder and CEO of

Dennis is an expert in leveraging data to solve enterprise use cases and a serial entrepreneur who’s successfully exited several companies on that theme.

His long-term vision of killing the inbox led to the formation of and the creation of Amy + Andrew, artificially intelligent assistants who schedule meetings. He speaks frequently to anyone who’ll listen, from the crowds of Web Summit to his building’s doorman, about an optimistic future for AI, productivity, and the future of work.

Dennis was also an accredited Associate Analytics Instructor at the University of British Columbia and the author of Data-Driven Insights, on collecting and analyzing digital data.

Originally from Denmark (and keeping his accent), Dennis is now a New Yorker for life.

How did the concept for come about?
Amy (and her brother Andrew) were born out of the pain I had when I was running my previous startup, Visual Revenue, which we sold to Outbrain in early 2013. Later that year, I had a bit more time on my hands, and I counted up all of the meetings I had scheduled in 2012. The total was 1,019 with 672 re-schedules, and I scheduled every single one myself. That’s painful. We know it takes upwards of 15 minutes and eight emails, on average, to set up a single meeting. That translated into about eight or nine very sad hours I spent every single week—usually in the evening at home—scheduling my meetings.

So I brought together the core team from Visual Revenue in late 2013 to start sketching out a rudimentary solution. We then raised a seed round of financing in April 2014 in order to figure out if meeting scheduling was a tractable problem. We launched our beta that month, and began scheduling meetings. Our goal was to collect and annotate enough scheduling-related emails to understand whether AI could fully take over the job of setting up meetings.

As it turned out, it is a tractable problem. And over the past five years, has set up hundreds of thousands of meetings and processed over 11 million scheduling-related emails.

How was the first year in business?
Hard! We were fortunate in that there is huge demand for a solution to scheduling pain, and hundreds of thousands of people told us they were looking for one. We were unfortunate in that shortly after we commercialized in October 2016, we realized we had to refactor our software, which made for some bumpy going (and grumpy customers) for the following nine months, give or take.

What was your marketing strategy?
It has taken us some time to determine whether we were, at heart, a B2B or B2C2B company. We’ve landed in some ways where we started: we focus our efforts on individuals and small teams at SMBs. That means our pricing is super low, and our messaging revolves around solving scheduling pains wherever you work. We’ve found that thought leadership around AI, combined with much more tactical content around productivity and a strong social presence, are the key drivers of inbound interest.

How do you define success?
In startups, some entrepreneurs identify with the destination and hinge their self-worth on whether or not they reach it. Others identify with the entrepreneurial journey and identify with how they play the game. I’m personally more of a journey guy.

It almost goes without saying, we’re striving to be the next billion-dollar company; however, success to me is really playing the game well, no matter the outcome.

What is the key to success?
Grit. It’s that simple. You need to be able to persist when you feel like giving up, when your board members, friends, and family think you’re even a little bit crazy, when the signals of success are faint (but discernible).

What is the greatest lesson you’ve ever learned?
Fall in love with the pain, not the solution. If you identify a big enough pain point, it is on you to deliver a solution that fully solves it, and to not get too attached to the first version (or third version) of that solution. That’s where the grit comes in: you need to keep trying to find the right product/service/price point until you solve the pain.

What are some quotes that you live by?
“Never surrender.”
“Only the brave.”

What are some of your favorite books?
Let me provide a set of slightly unorthodox suggestions:

Shoe Dog. Phil Knight’s memoir shows that a dramatic financial entrepreneurial win like Nike doesn’t necessarily translate into the same emotional win. If anything, one might question whether it is worth it.

The Narrow Road by Felix Dennis. It’s important to understand that the only way to get rich, if that is your aspiration, and the above book might suggest it is not worth it, is to hold on to your shares at all costs. I mean, at ALL costs!

Mike Tyson’s Undisputed Truth. Knowing who to trust is hard, and if you single-handedly make hundreds of millions of dollars, then it becomes even harder.

Tell me about one of the toughest days you’ve had as an entrepreneur.
Having to cut a co-founder and friend from the team. Not cool.

When faced with adversity, what pushes you to keep moving forward?
Remembering that it is all just a game and that those three women at home still love me.

What advice would you give to young entrepreneurs?
Think of entrepreneurship as a lifelong career, not a one-off event. If you do, then each time you play the game, you are a little bit wiser, which theoretically should improve your odds.

Who else should we interview? Nominate someone!

Interviews are conducted for research purposes by author Jason Navallo for his upcoming book, Underdog.

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