Breaking Up with Your Solution | Dennis R. Mortensen at

In part one of my conversation with Dennis R. Mortensen, the co-founder and CEO of, he told us about the simple power of his AI scheduling assistant developed by his company.

In this second part of our conversation, Dennis explains his belief that soon our current way of arranging meetings will seem as antiquated as the FAX machine, and he also discusses his method of staying uncommonly close with the customer and the dividends it pays.

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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’m certainly a fan of being super close to the customer, because it constantly reminds you why you’re here.

Alexander Ferguson 0:18
In part one of my conversation with Dennis Mortensen, the co founder and CEO of, he told us about the simple power of His AI scheduling assistant developed by his company. And the second part of our conversation, Dennis explains his belief that soon our current way of arranging meetings will seem as antiquated as the fax machine. And he also discusses the method of staying uncommonly close with a customer and the dividends it pays. That’s I’m excited to continue our conversation. And we were just talking about this, this journey where you you heavily invested in this, this underground layer of people don’t even realize or see that now. Amy or Andrew? Can they can understand what you’re saying when it comes to scheduling? And now you could there’s so much capabilities and grow on that. And it’s exciting potential, but something you mentioned earlier, it’s a change in behavior. And so tell me more about this journey, this change of behavior of you have to get people used to, I’m going to give up control to an assistant that’s not even human, how do I know they’re going to do a good job? What are your thoughts around overcoming that behavioural change in people?

Dennis R. Mortensen 1:27
I think it’s inevitable that we will get to the other side, not just the delusional intrapreneurial idea of you surviving, which is unlikely, but the fact that we, as an industry will get to the other side. So there was a time not long ago, if I just go back to my last venture for where every single employee contract, I printed out, signed in paper and scanned and sent back to them. You can have a laugh now, but it’s not that many years ago, as in every single one, every single master service agreement with any one of our customers, same process, then slowly, then quickly, then, inevitably, we all ended up signing our contracts digitally, as then you haven’t signed anything on paper in the last many months or many years, depending on how tech savvy you are. It seems equally inevitable that you telling somebody else over the phone. Oh, yes, I will be in New York next week, we should meet up, send me an email with a few times. Well, that will sound overly eccentric, kind of like, you know, faxed me the contract. What? I don’t even know how to do that. I said, Where do I go to make that happen? So we will get there. It seems like this spring, given what we’ve been through, have accelerated that. So May was the best month ever for us. This Tuesday was the best day ever for us. June will be the best month ever for us. If the current trajectory can hold that could implode, of course, but so far, so good. And that means not tomorrow. But in the not too distant future. We’ll go from this being kind of exotic, interesting. I understand tech, I’ll make this work for me, or I want to change my habits to your why, why wouldn’t I or I must learn. But it’s certainly a habit change. And we had some design handicaps early on where perhaps we didn’t fully understand it, that there was actually some anxiety attached to that of using a new technology. It’s kind of like one could imagine you right out of college is 10 years ago, and they ask you to sign your contract on a PDF. Can I am I going to get paid? Is this right? This work kind of similar, and we’re seeing that some people are so having that feeling wait. I’m an account manager. This is a real meeting. I’m a little nervous here. So we’ve done a ton of things of late such as you ask Amy and Andrew to set up a meeting. The very first thing we do is we immediately split second, read the whole thing back to you as in Hey, did you ask to set up a Zoom meeting next week for 45 minutes with John and Susannah Sam being optional under this title? Yes, I did. Then you just reply. Yes. That was a good kind of step for where Okay, let me see. I can write anything however crazy to the agent. The worst thing that can happen is that something comes back with a need to kind of go chew, okay,

Alexander Ferguson 4:53
that affirmation, examination they provides comfort

Dennis R. Mortensen 4:58
and it sounds Tiny and small, it was Major. Then another thing we did a blade is even with that way, okay? Now I know you understood everything which I asked you to do. But what are you going to say to people? Now we have this kind of preview all the emails, they’ll go out to all the participants. Okay? Okay, show me what is about to go out, okay? Hey, Suzanne can do this, Hey, John, can you this, okay? If these all the emails are going out nice, I didn’t have to write them. But now I can see what will go out. And just by seeing it, I’m a little bit more comfortable. And you know what you need to this often enough, as in, there’s plenty of platforms where we do a quick preview, before we do the send, or submit or save and say, show me the preview, I say is this proper? And that is what well, we try to apply that across the platform. And just to give you another kind of design change in that direction for where we used to be a little too autonomous. For where I believe, at this juncture, we should do this. Many times will correct. But the few times where we were not. People always came back with the you could just have asked me. And we now have these forks in the road for where we don’t move forward. We just ask you, Hey, everybody replied back. But Suzanne, do you want to schedule the meeting as is? Or do you want us to try to find a new time?

Alexander Ferguson 6:33
Which a real person would do? Right? Like they would check exactly. Yeah. Someone says, I see now the power that’s been put into all these forks, these thoughts that that is not not easy for someone else to duplicate in these as a counseling calendaring thing. So I’m curious that question for you of if there was a learning out of out of this venture, or any of your previous four ventures or more that another entrepreneur could learn from if you were to share a piece of wisdom or advice that helped you overcome a challenge? What What would you share,

Dennis R. Mortensen 7:06
I’m certainly a fan of being super close to the customer. Because it constantly reminds you why you’re here. And if you are a little bit technical, it’s very easy to fall in love with your solution for the sake of the solution, because just I could sit the next five years and just geek out on my laptop with some Diet Cokes and be a happy dude. Not a good business, just a happy dude. So the closer you can be to your customer, the better. And just to give you a good example, in our last venture, we moved in with our first customer. I said, we do predictive analytics for media. And we moved in with the newer Daily News. And we sat there, for the first year and a half, I sat right next to the editor in chief. And I’ve been called the most rude things for a year and a half. If you sit on a tabloid like that, and after that, we moved in with the Associated Press and set that set there for the remainder of the period until we got acquired. That worked very well. This venture, we try to do something similar. But given we have a b2c to b type strategy for we attack it from the bottom up. Customers are, you know, many times individuals is a guy at Spotify, he started using it. Now there’s five people at Spotify, that turns into a little team might have another team at Spotify. And it kind of grows from that. And we’ve seen that with fellow Dropbox, Slack and others. But we’ve certainly tried to be very intimate. So I’ll just give you one example. We created this group of people that we called Time Lords, and we are very close with them. And they are kind of time hackers, if you will. And they’re trying to make the most of their calendars. And we show them most things when they’re not so early that you would be beyond embarrassed and you don’t have the answers as in is this a pitch Dennis? Then it’s a shady pitch. No, it’s just really you and me trying to solve this together because I know you are the user. I’m the vendor that worked very well. And we did and are still doing kind of office hours with PMS office hours with me. Early previews. hos critique this unlike this I don’t like but that have worked very well. But just a different setting.

Alexander Ferguson 9:33
Being intimately close with someone, whether you’re inside them or you’re you’re elevating, giving a title to your customers that makes them feel important. That is powerful. Thank you for this insight. This is really cool. People can go where to learn more

Dennis R. Mortensen 9:51
people should immediately even before this finish, go to extra AI. There’s a free edition. Sign up try to schedule two or three meetings, then email me at Dennis at human dot x II. And tell me about the experience. And remember, I just said 22 minutes ago, I run inbox zero, so you are guaranteed a response.

Alexander Ferguson 10:16
That concludes the audio version of this episode. To see the original and more, visit our UpTech Report YouTube channel. If you know a tech company, we should interview you can nominate them at UpTech Or if you just prefer to listen, make sure you’re subscribed to this series on Apple podcasts, Spotify or your favorite podcasting app.



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