The Bots that Bring People Together | Dennis R. Mortensen at

One of the more notable truths to emerge in the digital age is that as complicated as software may seem, the people using that software remain infinitely more so. This is especially apparent when it comes to scheduling meetings.

Lives are difficult to coordinate, and people may not always remember the numerous requests coming their way. So it may be fitting that software is being developed now to manage the people.

Our guest on this edition of UpTech report is Dennis Mortensen, the co-founder and CEO of—a company offering a very simple but powerful tool: An AI assistant that can reach out to your associates and schedule the meetings for you.

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Dennis is an expert in leveraging data to deliver business insights. A serial Entrepreneur, Dennis built and successfully exited several companies before founding in 2014. Along with co-founders Matt Casey and Marcos J. Belenguer, Dennis set out to solve a painful problem — scheduling meetings — through a sophisticated AI platform that saves people time and effort.

Dennis is a recognized leader, author, and university instructor in the field of digital data and analytics. Originally from Denmark, Dennis lives in New York with his family.

DISCLAIMER: Below is an AI generated transcript. There could be a few typos but it should be at least 90% accurate. Watch video or listen to the podcast for the full experience!

Dennis R. Mortensen 0:00
I like the idea of autonomy, as in being able to ask some entity, human or machine to do a task that I don’t want to do, so that I can immediately archive it.

Alexander Ferguson 0:24
One of the more notable truths to emerge in the digital age is that as complicated as software may seem, the people using that software remain infinitely more. So this is especially apparent when it comes to scheduling meetings, lines are difficult to coordinate. And people may not always remember the numerous requests coming their way. So maybe fitting that software is being developed now to manage the people. Our guests on this edition of UpTech Report is Dennis Mortensen, the co founder and CEO of, a company offering a very simple but powerful tool, an AI assistant that can reach out to your associates and schedule the meetings for you. Dennis, I’m excited to be talking with you right now and hear more about excellent AI. To begin, can you share that the concept of it in five seconds? Very brief, what is it?

Dennis R. Mortensen 1:11
Sure. We schedule meetings. That’s it, there is no slide to that’s the end, why

Alexander Ferguson 1:21
the name, just one letter short URL, or

Dennis R. Mortensen 1:26
if you’re doing anything on the internet, there’s something romantic about a single letter domain, whatever you do, and you are making come up with all sorts of sorts of brand stories. But if we’re just a little bit geeky, a single letter domain, or I’ll give up one of my children for a single letter domain, as in that is gold. Putting putting that aside, we suddenly like the idea of people imagining an agent setting, and we can then append It’s not that I think AI is always a good moniker, but it certainly gets people thinking. And that’s perhaps just enough to kind of say, Ah, why is it that Dennison team is taking a different take to that of say, Calendly, there might be something here, let me at least give it a whirl and see whether it’s different. That’s one, two, I like the idea of kinda, X marks the spot and your calendar. And if the domain is available, take it, I bought it at auction, by the way, before we started the venture that was not cheap.

Alexander Ferguson 2:42
I can imagine this concept of differentiating, though, right in the Pros and cons to it marketing term, many people just pull it in. But truly, I think you if I can say this correctly, you went from the heart of it. No, truly, we want it to be run through natural language processing, can you share that a bit more details of about the technicalities of how it is different from Calendly, or other features out there.

Dennis R. Mortensen 3:08
I like the idea of autonomy, as in being able to ask some entity, human or machine to do a task that I don’t want to do, so that I can immediately archive it. So I’m an inbox zero kind of guy. And the worst thing that can happen to me is not many emails, as people have this idea that oh, Dennis, you must be dying on the inside. Given this promise you made yourself of not leaving the office before you hit inbox zero. Now, that’s the easy part. As in, there’s no difference between 80 and 120. No, what I really hate are things that I can’t remove from my inbox, because there’s a dependency on another person. So I’m waiting for you to reply to me. So what do I do now, to keep it or to I trust you to reply to me, I don’t trust anybody. So I need to leave it in my inbox. Now with Amy and Andrew, there’s this level of, again, autonomy is suddenly a grand word. But forget about that. The fact that you can ask them to set up a meeting so that you can immediately archive it, because it’s now on them to assemble the email, reach out to you reach out to you again, reach out to you again, and then mention to you that this is probably going to be the last time I’m going to be pinging you and if you don’t respond, I’ll have to go back to Dennis, and you still being tardy, going back to me X number of days later and say hey, Dennis, I actually reached out on Monday, and on Wednesday, Friday, but I didn’t get any response. So you should probably reach out yourself. Oh, fine. And then I can take whatever action I want. That is certainly very distinct to how we attack this. For where and there’s nothing wrong with that of sharing a link. We have all the kind of calendar pages and single URLs and combine calendar pages and teams and round robin, all those things that you should have as a calendar platform. And it’s very similar to Calendly. And sometimes that is what you need.

Alexander Ferguson 5:16
So speaking of then, not not pivoting and moving forward this this journey of now, six years in the six years into this, what do you see in the near term the next year so that you’re working towards your roadmap? And in the long term, 510 years, what are you working on? Where do you see you’re headed?

Dennis R. Mortensen 5:35
We might have at least initially, under invested in the scheduling engine. So if you think about what we do, it is one thing to understand what is going on in the universe. So think about a self driving car, you see some object in front of you, you might even understand what it is. But you now need some engine that can decide what do I do with what I now know, if you see an object, which is unidentified, but the predictions suggest it’s a plastic bag, but you’re not sure it could be a baby, you don’t need a decision engine for what to do next. And if you’re not sure, and it’s a self driving car, I suggest you slow down and stop. And if it’s a meeting, you also need to have an idea of what do I do with the information which I have, and that scheduling engine have become extremely robust. But for us, it was unfairly invested in. So now it’s almost kind of tilted. Where a lot of what we do, if you think about even just a calendar page, if you go to a calendar that actually is less dentists, what you will see is different kind of meeting templates of mine. But they’re not just free times on my calendar. Now they are availability extracted from a scheduling engine based on what is Dennis’s calendar look like right now? What are the particular constraints for this particular template? What other promises have I made for dentists in this very moment? And given all that, what can I safely present to people so that if they click something, they are not only happy dentists is also happy? So it looks very simple on the guest end, but it’s become this kind of very complex and very interesting kind of scheduling engine. So that I certainly like and to then answer your question, what is it that we’re looking at right now? And what is it that we’re doubling down on, we are suddenly doubling down on that scheduling engine so that you can extract that availability and expose it in many forms. In many places, from dentists, I just need a quick way to quickly extract the five times a give to somebody, okay, let me find you a function for that. Dentists, I need to have a quick page I can just send people to for where it adheres to these rules. Let me give that to you. There is I really need to be flexibility of being able to describe an ad hoc meeting on the fly and natural language. I think you were spent years on that. Yeah, let me provide that to you. But it’s all rooted in the same scheduling engine. And we want to expand on that complexity for where, see, I run a team of SDRs 11 salespeople, and any new customer coming in, you probably need to qualify in some capacity, that customer doesn’t care who they speak to, they just want to speak to somebody as soon as possible. I also want them to speak to somebody as soon as possible. So I need the engine to just kind of see, okay, of all these people with what the customer asked who’s available first, who’s the best fit. And I’ll kind of connect these two. So these all these corner cases where when explained as I get it, let’s just say 1000 of those cases, and I need to support all of them. That is where we’re doubling down, and it’s not necessary, as visible on the front end. Now, then on the front end, I would really like to make sure that we are present and available in any context where you talk with other people about meeting up. So today that is suddenly on the web, in email on Slack. But you speak to people in other channels, LinkedIn messaging, and so on, so forth. I should be in any one of those channels. So you don’t have to do context switching. That’s one on top of that. And then lastly, I would like us to kind of integrate with

other solutions that kind of come along with the meeting. So whenever you do a meeting, there’s typically a set of associated chores that come along with it. So you’re in Manhattan in August as we do agreed, we should probably meet up for sushi. But if Amy is scheduling the meeting, and we agree it’s a lunch thing. She knows me, she knows you. She knows his lunch, why you’re not just logging into my Open Table and booking a table at Horos. As in, that’s actually not represented as and you don’t need any data science, you need some engineering, but it’s actually not something that’s hard. Or, you know, where my office is that, you know, I’m at my office, you booked a meeting there, you know, the next meeting is in Midtown. Why am I even pulling out my phone and trying to book a new book? Why is that not just down? Why don’t just walk out the door and it’s there, you know exactly how long it’s going to take me to get there. So just book it. I don’t want to deal with that. So we want to have all these additional chores attached to it. And we do some of it today, like a Zoom meeting. So you may actually ended up criss crossing a little bit because I asked my agent to set up a meeting. And as it’s asked for it to be assumed to log into my Zoom account, extract a distinct URL, attach that to the meeting, so I don’t have to write or do the same with Microsoft Teams or Google meet. Or if you hear the office, look at my resources book a meeting room, so I don’t have to write this whole corner in office fighting for who got to meet you will just find one which is available and I’ll go there.

Alexander Ferguson 11:25
Be sure to check out part two of my conversation with Dennis in which he offers some important insights on why you should avoid falling in love with your solution for the sake of the solution.



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