Dennis Mortensen, CEO of X.AI | Analytics, Data, Failure, Success


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In this week’s episode we sit down with Dennis Mortensen, Founder of X.AI. 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. 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. 

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The Success Story podcast is focused on speaking to incredible people who have achieved success through trials, tribulations, wins and losses. In each episode we sit down with leaders and mentors.  We document their life, career and stories to help pass those lessons onto others through insights, experiences and tactical strategy for business professionals, entrepreneurs and everyone in between.






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Scott D Clary, Dennis Mortensen


Scott D Clary  00:05

Thank you for joining me on the success story podcast where we speak with incredible leaders mentors who have achieved success with trials, tribulations, wins and losses. Today I am sitting down with Dennis Mortensen, who is the CEO and founder of Now, I’m going to let Dennis tell his story. But to give you a Coles notes, Dennis is an expert at data and delivering data through business insights. He’s a serial entrepreneur, he’s successfully exited several companies before founding X ray and AI in 2014, along with two of us, other co founders, Matt Casey and Marcos belongia. Dennis is solving a problem with Meeting scheduling, which I’ve used the platform myself, I liked it a lot. And from 30,000 feet and may not, you may not understand why you have to solve for meeting scheduling, but I can tell you firsthand, with the amount of hours and stress and back and forth that there is a problem in the meeting scheduling space, which a lot of you know business people salespeople have to deal with. So a couple more things about Dennis, he’s a recognized leader, author. He is an adjunct professor, for the University of British Columbia West, I’m in Canada. So I recognize I recognize University out there. He’s the author of data driven insights. And he frequently speaks on analytics and data. He’s a native of Denmark, but he’s currently in New York. So Dennis, you know, give me a give me a summary of your background, you know, where you came from, and how you got to


Dennis Mortensen  01:41

Sure, and thanks so much for having me here. How did I end up here, I could obviously kind of give you the number for my mom. And she will give you the four hour version. And it will be fantastic, I promise you. But let’s see if I cannot give you the more crap, compressed, less flattering version. So I took a CS degree some 23 years ago, and immediately decided that I would not ever want to be an intrapreneur because my dad, my uncle’s, my cousins, all were intrapreneurs in one way, shape, or form. And I’ve seen the amount of effort that needs to go into that I was coming home late, working six days a week, falling asleep in front of the telly, not eating dinner with your kids. Those are kind of the bad things, I didn’t immediately see the positive thing. So all I wanted was really just to get my CS degree and go work for IBM hadn’t even called them but in my mind, I’ll just get my certificate, take my bicycle, go out to IBM and say, Hey, so where’s my desk? I’m ready. Let’s do this. The funny beginning, though, was that I did game development to kind of fund my studies. And the last title that we worked on, we’ve worked on probably for a year and a half. And certainly the way you pay most students is on delivery because they’re super bloody flaky. So let me see something, then I give you some money, there’ll be the exchange, but the company went bankrupt. And in my disappointment business, I ended up acquiring the assets of that company. That sounds like something major. But this was at a time for where most lawyers didn’t understand. much, if anything about software, all they wanted to sell me was chairs, tables, leases, cars, what have you. All I wanted to buy was two CDs, and they just didn’t get it. So I bought it for next to nothing. The company came back, had a refinance bonus figured out that one of the engineers had bought all the software assets. So I sold that shortly thereafter and made what I thought at that moment was a fortune in hindsight, not really. But at that moment, suddenly, if you’re kind of right out of school, and you get a little bit of money in your right pocket, you’re winning. That was not enough for me to kind of decide that. That will be the beginning of my intrapreneurial life. Nope. What I wanted to do was take that money, put it on read, play the night out, lose it all and go work at IBM. So I started a internet analytics type company in June of 96. If you want to be part of the Internet revolution, you should probably started in June 96. So I did that. And we ran that up without any funding so entirely owned to an exit in April 2000. If you don’t want to sell a company in the combo, you want to sell it in April 2000. So timing was just fantastic. Stick. And that gave me a lot of additional money in my left pocket. And that was probably the beginning for where I guess I’m an introvert intrapreneur out. And we did then multiple ventures after that, and the one. This is my fifth venture, the third one we actually did out of Budapest ended up being acquired by Yahoo. And some of the acquisition terms were that I moved to New York. And I arrived here 11 years ago. And that’s how I ended up in New York, then we did a predictive analytics venture. For three years, I got acquired by Outbrain, and then brought the team back in 2014. And kind of off to the races again, and if anything, I just like playing the game. So the whole idea of just being an entrepreneur, I am so long on that idea that I wonder who’s gonna run this to the end, sit at 65 still be pitching you on some idea that I’m working on that we had together last weekend? So that’s my short story.


Scott D Clary  06:03

I love it. It’s, you know, I think that you, I think that you’re describing what a lot of entrepreneurs describe, because from the outside, they look absolutely, you know, batshit, crazy, like there, but it’s not, it’s a love of the game, it’s a love of understanding how to play the game of Listen, we’re in we’re in 2020, and people are realizing that jobs are not secure, that working for big companies are not secure. Obviously, nobody expected this. But you know, the traditional workforce, somebody worked for an IBM or for business machine, like the the place to go work. It’s not, it’s not the safe option anymore. And people don’t spend 30 years in a career. So I you know, I think that the takeaways Go Go try something, go try something.


Dennis Mortensen  06:51

And I think there’s at least that, from me, and it sounds like I’m on commission from some organization, I’m not, but there’s this need for me to tell people to at least go tried once, it might not be for you, you might actually dislike the initial chaotic setting. And what I see as romantic, you see as frightening. And for every time I step forward, what I really end up liking and fall in love with just gives you anxiety, but I still suggest you go out and try it. Even if you lose, I think you spent 18 months trying to bring something to life that just didn’t survive. It was stillborn. That’s okay. That is probably the cheapest, most valuable MBA, you can go acquire US and you can go spend that 200k up at Columbia. And I’m not saying you’re going to come out dharma. But if you really want to come out smarter, I suggest you do the two years on some startup idea, because that is just knowledge that is very hard to acquire elsewhere. It almost impossible. That’s suddenly one bullet, I think the other bullet is if it is for you, when you do lose that first startup, which must be the assumption. SM almost every startup will have a super optimistic beginning and a very sad ending. That is how most of them are defined. And that is okay. You just need to at least a show it won’t go well. But then you should imagine not a single venture probably a lifelong career as an intrapreneur for where you can do 1012 Interesting ventures, only two or three of them need to kind of work half Okay, can I pay for the remainder of them. So that’s a lifelong entrepreneurial career, or as I tend to call it, it’s the 50 year fund. So most VCs will run a four year fund, you can’t do all of them at the same time. You have to do them over 50 years. I’m 23 years old on my fifth venture, and I got five more me, perhaps, yeah,


Scott D Clary  09:13

well listen, like if you, I think that I think the biggest thing that you mentioned, that’s important to remember, takeaway is like, you’re going to fail a lot. And if you can get over that hump, then you’re just on to the next one on to the next one on to the next one. And you learn every time and that’s why you hear like, you know, like, I don’t want to hijack this, but like you hear about like Zuckerberg and whatnot. And he’s like, how many things he tried before Facebook and I’m sure like all the other apps that you can name you use on a day to day they’ve all tried and failed, like, you know, many, many things before they become successful.


Dennis Mortensen  09:45

And I know it’s easy to say, but you certainly see plenty of people and you must have friends who worked at Morgan Stanley and finally assembled the courage to quit their job. Go do that thing that they dreamt of doing for years and failed on it. But they sometimes attach their life’s worth to the success of their company, which is completely unfair. And those two got nothing to do with each other. So your life’s worth, as it do just a nice guy. Whether you’re making no 40k minus 300k or 800k, a year on your newly established venture, you’re still a cool guy. So somehow was why I tend to not honor disrespect, speak of startup as a game, just like any professional football, if you want to really become good at your craft or any other sports that you go watch, you must assume that you play a lot of games, and you lose many of them. But the reason you had this particular level is that you were willing to lose along the way. So your lies worth is not this particular venture, it’s just how you play the game. And if you assemble a little bit of knowledge along the way, you’re probably smarter than the next one. And that’s how you become a pro. But not one for where, sadly, some end up with. Not a full on depression, but just a sad set of months, if not years in life for where I hated the last eight months, I had a difficult time in assembling begin to curse to get up, go back out into life and tell people who I am given I told everybody, up until this point that I was an intrapreneur. And now I have to tell them that well, it didn’t work. So I’ve done my fifth venture, one of them didn’t work. I proudly put it on my CV, and I proudly speak of, you know, all the mistakes, why I think we failed. Now, I might even still pitch it as in, hey, I think we could have made it work. Have we done this? But it’s not something I would want to hire. There’s no you’re not a part of my life that I want to be without? But


Scott D Clary  12:03

how do you why do you think that is? Why do you think that? Like how do you get over that? Because I know actually, I know why it is a silly question. It’s it’s tough innately to accept that you’re bad at something. But how do you get over it? How did you get over it, because I think that’s the lesson people can definitely learn from.


Dennis Mortensen  12:21

I wish I had some magical process, if you just went about applying that, then you would escape this depressive moments that might come along with not winning, I do think it’s the best thing I’ve ever come up with. And I know I’m repeating myself that if you try to at least not attach yourself to the success of the company and think of it as really just a game. It sounds extremely disrespectful, if you raised any amount of money $100,000 from a pool of friends and family, or millions of dollars from institutional investors, it’s probably the same emotion that comes attached to any one of those pools, you should still make both yourself and them aware of the fact that I’m taking this very serious. It’s still a game though, for we all agree are probably going to lose all the odds are against us. But we know that otherwise it wouldn’t be a standard to begin with, it will be a going concern. And you wanting me to sell whatever witches we can buy for $10. And we can sell for 13. So we know we’re going to lose at least making sure that all of your constituents are equal you were of where this will end. If we then escape it off, we should all be ecstatic. That’s just not what we expected. We expected that the next 18 months, 24 months will be an unfair amount of work. And come the end of it. We’ll have nothing to show for it. But you know what? It’ll be an amazing story. If we do, or you want something, otherwise, where else would you think to get hundreds of percents of return? If you want something else? Well, I think Citibank is doing oh point 2% At the moment, you should put your money there.


Scott D Clary  14:17

It’s true. And I think that I think that a lot of entrepreneurs, they go in and they get money. And I think they may be it may be intimidating, especially for first time entrepreneurs. But you have to align with the right money you have to have smart money you have to have a partner that’s going to invest is going to provide value and you have to have a partner that is putting money into 100 Ventures knowing that only one is going to be successful. And if you have the right partner then it’s not so stressful anymore. But they have to venture has an onus to educate entrepreneurs too.


Dennis Mortensen  14:47

I think you’d wait and you actually picked up on a point for where you can add unnecessary stress to the equation yourself. If on your Very first venture, your first 40k Is your parents savings, all of their savings, not one out of many investments that they will make this is their only investment that is not healthy. So you should try, at least to find people were you know, I’m one out of many, and they have a portfolio. And in that portfolio, there’ll be a lot of bodies, and it’ll be okay. There’ll be a few winners, and we’ll pay for the rest, and I can still come back be in his next portfolio. So in that regard, try at least to design it in such a way that you aren’t adding unnecessary stress yourself.


Scott D Clary  15:42

I agree with that a lot. Okay, so, so question, before we go into exci. Why, why multiple analytics companies, analytics seems very dry, from my point of view. So what what makes somebody have a passion for data?


Dennis Mortensen  15:58

I think there was an article in The Economist at some point many years back, that was titled, data is the new oil. And I think that headline sounds perhaps a little dated at this very moment in time. But there was some truth attached to it, that if you have a reasonably good understanding of where data might originate, how you can tap into it, how you can extract it, and how you can then refine it to the extent where some people will see value in it. That is a skill. And like any other skill, if you continue to kind of perfect it, you probably become good at it, help perhaps even world class, if that’s what you spend your life on. I do think sometimes a little bit of serendipity is attached to where we end. And I’m not suggesting I woke up last year of Kahless, thinking I should be the data Baron of the 20th century, it was just wonderful. Where our first venture, we saw plenty of people running websites, without having any idea of how they fared. And at that point, nobody could slap a set of Google Analytics pixels on a website, they just had raw web server log files. And we would mind those. And we stumbled into that, perhaps a little bit. But then once you go into the mines, and you work there a little bit, that becomes your identity, right, and you learn something, and then you learn a little bit more. And all of a sudden, you start to see things that other people can’t see, just like you can see things I can’t see, because you have an expertise that I don’t have. So you can kind of look out the window and see things or be at a meeting and have people say one thing, and here’s something else, I’ll just hear what they say, But you heard something else. And that particular vision, I think is interesting once you start to get it in whatever particular attack angle you’re at. And for me in being data. And then the next one, you figure out, Where else can I go drill for some data. And if you think about external AI, even though we’re in the meeting, scheduling space, we’re still really one big data science bit like anything else. And we can kind of go into detail on why that is. But that’s certainly been the route of any one of our ventures. And I imagine that that will be the route of any future ventures that we might do.


Scott D Clary  18:36

So that makes a lot of sense. I like I like how you like how you framed the when you’re in a meeting and you hear one thing and one person takes for face value in the other person, that that insight is very powerful and driving like especially what you do, I speak with a couple entrepreneurs on this and some people like within organizations like career lifers, but the entrepreneurs, they always have a knack. I don’t know if it’s a skill, but it’s a knack for being able to, to like look that level deeper than the average person. That’s where they find the pain point, or that’s where they solve the problem. And then that’s how they become successful. That’s why you see, all these people that have been in a career, the most successful entrepreneurs are the ones are the highest rate of repeated success, or they’re in a career, they know their industry, then they go and branch out and they build a company after you know, like mid 30s to 40s, whatever. Not the Stanford MIT grads, like That’s a rarity. It’s usually the ones that are much older, right?


Dennis Mortensen  19:33

That is funny, and there’s been multiple studies. So if you ask anybody who’s not in this particular ecosystem, to draw an intrapreneur, it would be that 22 year old dude from Stanford with a hoodie and that will be what that would turn in for that assignment. In real life, though, it is exactly what you describe is people who spin around typically A decade or longer, and at some point feel like they have the expertise needed to go do something. And those that turn out the most successful outcomes, people of our 80s, it might not sound as sexy. But that is where success starts to arrive. And that should, I think, provide a lot of people a lot of comfort for where I think the curve I looked at last, and I’m sure there’s a lot of elasticity attached to that suggested 42. I’m 47. So that might suggest I’m on the other side of that curve. But they’ll certainly be a lot of people before 42 thinking, well, that is, I’m not even at my peak yet. Even though you and me don’t fall into and it’s all about the individual, the team, the execution, the idea, the market timing, but still, there’s something when you take a step back and look at that curve. I suggest it’s obviously not too late. And I think a lot of people have this is too late. And sometimes the too late is really not on them being able to do it is all of the commitments, they signed up for conformity to


Scott D Clary  21:15

like, kids and family,


Dennis Mortensen  21:17

dogs, cats, apartments, all the things in the background.


Scott D Clary  21:20

Yeah. So okay, so let’s, let’s talk about So, first, what is it? What does it do, and then let’s talk about why you’re doing it.


Dennis Mortensen  21:33

Sure. So extra AI is a SaaS solution that helps you schedule your next meeting. So anybody really in any function will be asked to either get into a meeting later this week, get a meeting on the calendar for next week. And some will certainly do more than others. So you if you’re an SDR and you really just qualifying leads for your account executive help, you might easily have 12 calls on the calendar every day, if you’re a PM, you might have two or three with some design teams around the organization. Every day, if you’re a back end infrastructure engineer, you might have two a week. But we all if we turn up an office and touch a computer, have some meetings on our calendar, the vast majority, if not almost all of those we see on people’s calendars today. And in the US, you’ll have shown up 90 million knowledge workers will be scheduled by people themselves. They don’t have a human assistant, they don’t have any kind of software assisting them, they just have the pay. Tom, Jeff 10 minutes later today to kind of go through this or dear customer. Can we set aside two hours for training early next week at your office. And anything in between those two. And the way it works is that we typically use email that is the primary source, do a little bit of ping pong, and then we come to a conclusion. And then either you or me will do the insert on the calendar and add the participants. And it’s not that this is difficult. It’s just yet another chore for where you and me speaking. We could speak today at 230 at 130. Tomorrow 10. We could speak hell next Tuesday. They’re all equally good for me. What’s not cool, though, is me having to work it I know already. I want to talk to you, then the systems figured out now the software then provides you a couple opportunities. One you could do, what do you see in plenty other people do just send a link to a page where you expose some times under certain constraints. Like I set up a calendar for interviews, that is in certain times not certain durations, certain locations, say Skype or zoom, then I might have other constraints and other meetings that are a little bit more distinct. For there. You can email our agents Aimia, extra radii, or Android extra AI like I did for this meeting, I believe yes. I haven’t replied back Cece and Amy and say sure. I’m up for that. Amy, can you find time for a zoom chat early next week, or whatever I said? And as I said in that the agent will see who is Dennis? Do I work for him? Yes, I do. What is Dennis’s preferences? What does his current cabinet look like? What other promises have I made on behalf of Dennis and assemble then a response to you sent out to you and are more participants try to extract a response from you either in a click at one o’clock or you trying to move it out to say May because something kind of came up and then upon conclusion, assemble an invite and then add onto my calendar, and then send you an invite. And again, it is not necessarily rocket science in concept, it’s just a little tiny chore for if you need to be without it will be slightly happier. Now, we’ve gone to market with this S, on one end, a free solution, anybody can sign up. And then like any other SAS vendor think Trello, Dropbox and others with some premium features, and you can upgrade and pay us eight bucks. And hopefully you do and if you do I make a few pennies. So yes,


Scott D Clary  25:37

it’s all so I like that a lot. So how did you I’m coming from a again, so business or data analytics? How did you think of or conceptualize the problem that you’re trying to solve here? Because it makes sense. But why? You know, there’s I, I’m not going to name them on the podcast with you. But there’s a whole bunch of people that do the link to the calendar schedule. So how did you think of taking it the next level?


Dennis Mortensen  26:03

Any intrapreneur will have some process for how they come up with new ideas. The one process I suggest you do not implement is that idea of getting a couple of pizzas, a handful of beers, you pop by my apartment, we work the whiteboard a little bit, and we come up with an idea that is so fast, that I simply can’t believe that it’s of any good, there’ll be exciting because we’ll be a little bit bust. And we’ll tell ourselves patted you on the back that this is awesome. Know, what you should do is probably the opposite, which is try to come up with a list of hate. And that sounds very sad. So I run a little list on my phone on anything which I hate. So whenever I stumble into it, instead of immediately trying to figure out how can I solve it, I just write it onto my list. This I don’t like. So you stand in line at Citibank thinking, as you look left and right, this is fucking shit. And you’re right, I should figure out how to solve the retail bank pain might not even mean anything, but it’s just from major pain points to little tiny ones. And then once you kind of get to the end of one story or one venture, we take a look at your list. And so did I. And in our prior venture, which we ran for 1059 days to be specific, given I’m a data geek, we allowed us to go back and I think I had 14 pages of one liners of things I really disliked. And when you look at the list, you’re thinking, that is one sad boy, he needs to experiment. But really what you have is a treasure trove of good ideas. And then you start to sort that. And what I saw on that list multiple times was that I was I don’t know, to pece even as a VC backed company to hire either an office manager or a personal assistant. So I would sit at 10pm in my underwear with a bowl of cereal trying to get the next meeting on the calendar, thinking. Is this my life? Yes, I’m 42. Now is this my life ahead, then I would write it onto my list. So I I came back and looked at it, it just came back. So often I thought, okay, if I dislike this so much, there must be other people who dislike it. And the first qualification I do on my own ideas is one for where I try to disprove it. So the first thing is to try to do is to kill your ideas. So it’s so easy to fall in love with them as in that takes nothing. an intrapreneur will follow up with their own ideas. 20 minutes as in, you can call me tonight and say, Dennis, I’m coming over, I got an idea. And then come Monday morning, you will be a law, you’ll need a logic, some sort of app for whatever thing that’s going on, as in, I get easily excited. But your job is to kill it. You can kill it, you’re saved as a full years of your life. So in this, I tried to look at, as you alluded to, why is it that this particular epiphany isn’t unique to me. And if it isn’t unique to me, there must be some solutions. And when I look at the space, there’s not one solution. I found I think 81 some odd solutions. People who try it and died people who try it were still alive, people who tried who are barely alive, but they were all seeing the same pain. But they were all also at least to me and I know I’m heavily biased here, walking down the same Avenue which was wonderful where they couldn’t come up with with anything else, but okay, I need to book a meeting with somebody. So I don’t know their times, they don’t know my times, how about I just send them my times, then they can figure it out. But that seems a little unfair as in the pain that didn’t disappear, you just transferred somebody from you to your guest. So it looked like some total, the same amount of pain existed in the universe. Our take was wonderful. Where what if we could perhaps create this agent for where I could describe specifically what I wanted, so that I could remove some pain from the universe and not just put it on the guest. So that if not in full, then a lot of it could disappear. And we will both be slightly happier. And now it’s the beginning of that agent tape that none of the other folks have been able to do. And we’re still the only vendor out there giving that a whirl. It was also way harder, and way more expensive than we had assumed on day one. And as we did that, just give you one last step in my little intrapreneurial validation process, I actually hired two assistants full time on my dime. Even before we started the venture said, Hey, you’re going to be working for 50 of my friends. And I’m going to call 50, my friends who are no, who are not in any position to have a human assistant and tell them, You’re going to have one tomorrow. And you can’t ask them to do anything but schedule meetings. So what are you going to see? Would they even want that? That was a huge success. Because then you I am 14 years out in my career, because before I become SVP, a Flim Flam a timing, and I get an assistant called Tom. So I’m going to use Dennis’s system, he’s paying for it. And they went wild. That was a good indication, then the next step was to figure out, now I know they want what we have. But that’s a human, that’s way too expensive. How do I then use data? See if I cannot replicate the human and turn that human into a machine? And that’s where traditional expertise came into play? Very long answer. Sorry,


Scott D Clary  32:24

but no, no, that was a good answer. I love your story. It was a good start. Listen, that the podcast was supposed to tell a story. It’s. So why Okay,


Scott D Clary  32:35

so a couple things that are that. First of all, why was it expensive? Why was it an expert? Was this a bootstrapped? Or was it a VC backed?


Dennis Mortensen  32:46

That’s actually a really good question. So I think most people who are about to embark on this journey should have a clear understanding of whether it is bootstrap mobile, or whether it is not, you or me just can’t imagine how you can bootstrap yourself into a new car company, as in, they’re probably require some capital, as in, there’s not enough you’re making doing the grace to kinda get that started. Then there’s other things, in particular, in software for where you can easily imagine a new notetaking app being brought to life for very little capital, a couple of laptops, diet, Cokes, three months in the basement, and we could probably pull that off. And then there’s everything in between those two, this particular venture, we just assumed, given language is not a solid science, that we needed an unfair amount of data labeled, so that we had a corpus for it to go create a set of predictive models for how people talk about meeting scheduling that corpus, we initially assumed would be one size, I said, I get in an email, I label it for time and dates, locations, people intent. And you do that many times. Now, you have to figure out so many times. So how many is that 10,000 10,000 100,000 10 million. We thought it would be a little less. It ended up for us being about 32 million times. hand labelled. Imagine I gave you four highlighters and 32 million pieces of information and said Hey, could you please highlight that? Imagine the amount of time so I’ll just give you some magnitude. So we had at some point 100 people doing nothing, full time 24/7 and labeling data. That is a staggering amount of people trying to put in place a very strong Unique corpus that really only we sit with now is on us to figure out whether we can now extract some value from that corpus, but we certainly mind it. We also think we’ve refined it. And now it’s time to kind of bring it to market. But that was brutal.


Scott D Clary  35:19

Like, that sounds brutal. It sounds like so. So you went out and you had to, like this was an out of your own pocket? Like that’s, yeah, like, in theory, yes, you could pay for that yourself. But that’s not smart.


Dennis Mortensen  35:32

So we raised capital. Yes.


Scott D Clary  35:35

Yeah, that’s, uh, I, you know, it makes sense when you break it down. But I think AI is still very much a black box to most people, and they don’t understand it. So they think they, again, they categorize it into all the other software development type projects that are really just calls of different things, right. That’s really all it is. And but there’s so much more to mimic a human


Dennis Mortensen  35:57

to an aesthetics. It’s funny, right for where some software, which is cheap, could still be very valuable, but cheap, and very predictable to engineer, as in, you can almost put a project plan in place before you get started on how much time you need to go apply to this before you are able to have a product in market can be difficult, say for my mom to understand. But my mom immediately understands the idea of a self driving car, the ultimate engineering challenge of the day, as I get it, I’m in downtown Manhattan, I want to go to Midtown. I just asked the car and here we go. Yeah. But there’s probably 1000 predictions for every kind of meter you drive, somebody needs to be able to make 1000 predictions and make them at very high accuracy. Yeah, unless, of course, you’re comfortable with hitting a pedestrian every 100 meters, probably not, probably not. That is very interesting to kind of see how these very complex technological ideas are easy to understand on the consumer side, but have become ever more complex on the engineering side. But that is obviously this is where the excitement kind of takes over on my end, that is always what you want in any good venture, where if you have a small or no delta for where it is very easy to do. And they don’t necessarily immediately understand what you’re doing or why it’s of value. Now you want those who have a very large spread for where they immediately understand what you do. But it’s almost impossible to make examinees, you will be able to create some sort of note here for where any three guys out of Y Combinator tomorrow, and immediately say, You know what, let me start by hiring 100 people and labeled some data and see if we can not do what Dennis is doing. So that creates some sort of moat here, certainly for us to be able to do predictions that other people can’t do. But it just took way longer than we had anticipated. So I thought we were sitting in that basement for a couple years. Yeah, we ended up sitting in that basement for four years before we could escape it. And any machine learning startup want to have sums up escape, if you depend on label data for where you can label data forever, as in those self driving cars, who for the most part have safety drivers in the driving seat right now was part of how they labeled data, those safety drivers needs to disappear. So everybody’s running towards them. 0.4, you cross an inflection point where the very use of your product becomes the new labeling. So just by you, me setting up this meeting, you helped me create a little bit of data. Now a few sprinkles, right? But if you do that 100,000 times, I get a lot of data. So we crossed that threshold on June 1 2019. So that was the point where I went from a dramatic negative margin to a dramatic positive margin. But now it’s June 1, to be honest. That was not what I pitched in my first day. really honest. It was a different set of dates.


Scott D Clary  39:14

So So what is it so how is this okay, so now it’s obviously it’s got some most significant momentum. So how are you seeing it being used? And where do you see like a product like this like going in the future?


Dennis Mortensen  39:31

Let me use an analogy here. And then I’ll tell you about my fantasies or my wish. Take something like you and me signing almost all of our contracts digitally today.


Scott D Clary  39:49

We’re gonna do Yeah, you know now we all know we all Yeah, yeah.


Dennis Mortensen  39:54

Yeah, exactly. Now we all are, but you know what? Go back home. For decades, I can tell you with 100% certainty, every single offer letter in my last venture, I signed by hand, those printed out, it had my signature, we had two copies. And I sent you home with your own version, all of the MSA as the master service agreements that we signed with our clients, all 102 Before we got acquired, I signed by hand with this pen, because that’s what you did in 2010.


Scott D Clary  40:29

Now, even still, I know some companies like for RFPs for you have to use IV, when I used to work in telecom I used to deliver I used to have to deliver RFPs sealed in an envelope by mail with a soft copy on a USB like, it’s insane. It were still there, though. And for some industries.


Dennis Mortensen  40:52

I think you’re right, I do think at some point, we crossed from you and me signing a contract online, being part of the future sexy for the few to it being so normal, that I don’t even advertise it anymore, I just make the assumption that the recipient, obviously would assume that at some point, in the next hour, you’re going to receive an email and in that there’ll be a link for you to sign this, I don’t even say hey, by the way, we use this system, and you’ll get an email and an email to go in and sign it there. You’re not going to receive anything in the mail. But that’s kind of what we said, some years back. Now we don’t because it became normal. Now, if we take that, and take what I do today, you don’t have to say anything, if you want to set up a meeting yourself, you just do a little bit of email paper, because everybody just assume that is what is going on. However, some people do me others are moving towards a setting where you know what? I’m not sure I want to do this, it seems a little bit eccentric in the year 2020. I’m gonna either add a link help, I’m even going to CCN Amy, I might even say hey, by the way, I’m using this service email, we’ll send you a set of times in a moment and negotiate and get this on the calendar. But at some point, to answer your question, then what I want is for this to be normal. I want it to be odd, eccentric, and way old school. If you start to say, Dennis, can you do Wednesday one, if not that Thursday to I’ll be doing? What are you doing? Time for this Mickey Mouse bullshit? Yeah, then I’ll take control and say you know what? I don’t know. But I’ve CC to Amy. So you can find some time for us. So that is the inflection point I’m looking for, for where we are suddenly signing up, you know, 1000s of users, and I’m very happy with that. But many of them are tech savvy, or somebody savage to the extent for where they feel comfortable enough. They’re not yet my mom or people just in the workplace. You might just think, Ah, I’ve seen a link to a calendar a million times. Yeah. Because you me kind of work with people who are kind of tuned in for normal people. We’re still at the beginning. So I’m kind of waiting for that curve. And then once that starts to really that wave, really, when that come out arrives. I want to be the one surfing it.


Scott D Clary  43:25

Are you you are so you’d be like, you’d be like the DocuSign of, of the sign contracts or what? But yeah, you’re right. You know, there’s still I think that and the more I it’s funny, I was just speaking about this, I did an earlier episode. And we were speaking about collaboration tools and whatnot. And just tools that people are people are being forced to be more technical. With the pandemic that we’re currently living through when this is being filmed. I pray that, you know, this is this episode’s gonna go ahead and about a month, I really hope that things are a little bit better when this goes out. But right now we’re living through this and we can’t leave everyone’s work from home. So people are going to be forced to be more tactical companies are going to be forced to enable their workers to have access to all these collaboration tools, Slack, Skype, zoom. And I think with that wave, we’re forcing people to modernize. So it’s right there. It’s like we’re at the precipice, but we’re just, we’re just have to forget some things a little bit more than others. But we’re gonna move in that direction very quickly, I


Dennis Mortensen  44:28

think. I think you’re very much right. Certainly, the data we’re looking at right now on signups use it engagement, churn, all metrics that you would care about if you ran my business up into the right, not necessarily because we are more clever today than we were yesterday. But because as you alluded to, there’s a moment here for where they wouldn’t have planned for it. But now it’s forced on us. Now that is forced on us. We need to pick up some tools And I think in that kind of tools, it, some will sign up for zoom for the first time, some will sign up for extra AI for the first time, help someone start on slack for the first time. But there’s a set of tools here that are perhaps not to use a pop turn, but anti fragile, we are almost becoming stronger by this force move to a distributed setting. And that is certainly nice to see that the wave is moving closer, even faster. Obviously not nice to see the reason for why that is happening. But faster.


Scott D Clary  45:43

Know that I think you’re you know, I like that I like the reason why you want this to keep pushing that way. It’s like, it’s more than just a business. It’s like, it’s the advancement of how we use technology as professionals. And this is, this will be one of those things. And you know, I really haven’t seen anything like what you’re doing right now, to be quite honest, so good on you for writing down that list of things you hate, and figuring out because you’re right, there is like the worst thing, you know, as somebody who deals in business and sales and just in like communications with other stakeholders all day, every day is like, you set up a meeting. And then the thing is, like, who has the authority to ask the other person to put it in their calendar, right? Like, it’s almost like it’s like, you’d like stack ranked your your professional like value based on who allows the other person to put it in their calendar. And even worse is when you just seem like, oh, you know, find something in my schedule, there’s still like, a little bit of animosity around just sending over like a link, because it’s like, what about my schedule? You know, it’s like, it’s silly, but you’re right, there’s like a pain point there. So I do like the you’re moving. You’re you’re sort of defaulting it all to to an AI tool that that gets rid of all the awkwardness and and the extra 30 seconds and things that we just bug us. It’s it’s Yeah, that’s really a


Dennis Mortensen  47:10

no account manager was ever put in place to arrange meetings. Surely he can’t do his job without that. But the value is him speaking to our customers. Yeah, no account any services was put in place to schedule meetings, I want you to speak to leads help you if you could deploy a little bit of software and you can speak to 14 over 12? Well, I can start add up, there’s two hours every week, there’s 100 Every year, I know my funnel shit, that’s 70k in additional potential MRR that could be extracted from you, if I could do two extra. So that way it is arriving some is already taking advantage.


Scott D Clary  47:51

Agreed? Agreed. Okay, I want to I do like to ask some questions or to bring out like your experience and some insights. But before I go into that, because we’re gonna move off of xr AI to close it up. Is there anything that you wanted to bring or discuss that? We didn’t chat about?


Dennis Mortensen  48:10

I think still good chat.


Scott D Clary  48:12

Good. I’m glad. That’s, that’s what I like to hear. Okay, so a few more the more vanilla questions, but I liked them because they give me a little bit of insight. And I like the people that listen, like to hear this stuff as well. If you could tell your 20 year old self one thing, what would it be?


Dennis Mortensen  48:32

I used to be very attached to the idea of each and every team member being with the company from beginning to end, not fully accepting that other people might have careers where they go from one company to the next. And I took it as almost betrayal, when somebody resigned was silly, and completely misguided. What I would tell myself is if somebody comes in, and they want to have a two year career, helping out doing certain stuff, just try to just both make sure you’re both in agreement on that. That is what he wants us and then craft a setting where he can succeed in doing that. And you can get some value from that. But I used to be very emotionally attached to people quitting because I would never quit as in we quit. When we run out of money. That’s that’s the only day we quit and just didn’t see that I become way more relaxed and way more tuned into the fact that we have different trajectories, I am on one, you might be in another one. Sometimes we’re very aligned. And we’re gonna sit together for years and then and that’s cool, but I should just try to figure out exactly what trajectory you’re on and figure out how we can inject that into our organization. They should make the most of it. So you have a good beginning, a good tour or a good end.


Scott D Clary  50:05

Now, that’s that’s experience has taught you that. But I know a lot of people that over their entire career don’t come to that conclusion. How how do you as a young entrepreneur, or even perhaps as somebody who’s working for a startup? How do you enable that mindset, I don’t know how you would do that without offending somebody, if I was going to think about working with the CEO and telling them like, I only want to be here two years, they’re not going to give me a job, which is wrong, I think you can still add value. And if it’s purposeful, and it’s transparent, and there’s communication, it’s better always 10 of the 10 times, but I don’t know how to enable that.


Dennis Mortensen  50:46

I to think, and again, as you alluded to, it’s got a lot to do with the transparency within the organization. Some organizations are, through their values, quite transparent. Some are not those that are not might not really need to go work on this challenge. First, they might need to go work on the transparency value first, if that is a value that they want to go apply. But I think that’s where you should go solve it first. Reed Hoffman, was it in one of his books? I think so. wrote about this idea of the tour. And anybody who haven’t read it should pick it up. I do think it’s in one of his books. And the tour is wonderful, where the hiring manager or the organization should be crystal clear about, what does your tour look like, if your tour is one for where I want to come in as a junior SDR. And I want to leave as a Senior Account Executive. Fair enough? If that’s what you want. If there’s something I can give you, if I can give you that, how can we then craft a tour around that, so that you actually get to the end. But when you get to the end, you can now do two things? Because there’s a fork in the road, you can craft a new tour together as in? Do you have aspirations of becoming, say, Director of Sales? Well, perhaps I can create a tool for that of as I cannot, and then you fork out and you go find that somewhere else. But I do think, again, being super transparent, trying to figure out why are you here? What would like to achieve that? Can I help you achieve that? Because if I can’t, even if I don’t think I can help you achieve that. You shouldn’t get started, we’ll both be disappointed. If I just really want you to sit in your seat, be an SDR for three years don’t move? Well, you’re going to be sad by the day. So that is what I recommend. But it does take some transparency. I do think as you suggest, it might not be immediately emotionally easy for the 22 year old to just sign up for that, because he certainly wasn’t easy for me.


Scott D Clary  53:03

Yeah,that’s fair. But I liked the I liked the recommendation and the concept of the tour. I like that a lot. I’ve never heard that. I’ve never heard that before. I’ve heard it said different ways. Like you know, career mapping and, and, but like you make your 135 year plan and things like that. But the tour is I like it because it’s very purposeful. It’s like, let’s just discuss it and and and it’s no BS, it’s like you’re you’re, you’re allowing them to set an end date and an expiry date on on them within your organization. It’s not the it’s not the it’s, you know, the whole BS like, you know, where do you see yourself in the organization in five years? Like, even asking that question is presuming that they want to be in your organization in five years? And you’re almost like, it’s a leading question, as they would say, like, in court, right. So it’s anyways, but I like that a lot. And you also you kind of answered my next question, probably not entirely, but I wanted to ask some books, podcasts, mentors that you recommend for people to go learn from and you you just dropped the book, but any, any other things that you would tell people to go check out?


Dennis Mortensen  54:08

Again, you I can give you the usual books. So anybody on this podcast would have read zero to one or the hard thing about hard things, and any one of those that we supposed to read and then our bad? I like him as well. I’ll give you three recommendations. Not that we prepared for this, but I’ll give you three recommendations that are not on your current list. I’m sure I’ll tell you why. I think that interesting. So the first one is by Felix Dennis, a British entrepreneur who did Maxim he did a book called The no erode. So feel is is not a good person. It is probably an awful person. He just died recently. And I’m not saying that to this. But he says so himself. He lived an awful life and then change come the end, but it was probably too late. That book will teach you one thing to cherish your shares, and not depart with a single share unless you think it’s a good idea that is worthy of the 200 some odd pages, because I can tell you as an intrapreneur, that you shouldn’t just willy nilly handout equity for the fun of it, you depart with equity, because you think there’s a real purpose and value in doing so. That is an interesting book. And that text is rather rude. Throughout. He starts I think, on the first few pages of in years, it’s a read a last in describing just the different brackets. And I think the two to $10 million net worth is what he calls comfortably poor. So you Amir in the kind of comfortably poor category, perhaps just to kind of set the scene. That is, is a good book, The next one would be the mike tyson biography, again, perhaps at some point in life, a person if not awful, certainly not as nice as one would hope people would be. But it will teach you one thing, and you end up with a ton of empathy for Mike in the end. And if a single person ended up being able to create an unfair amount of wealth, and that is relative to your situation. So that could just be you and three friends or a family and creating 800k Or for Mike $300 million, doesn’t matter. But some settings where you now ended up mostly on your shoulders, creating a lot of value, who can you trust? So in Mike’s life, that will add up to nobody, sadly, acid, everybody is trying to take advantage of you? How do you then determine who you can trust? Acid? What particular investor is a good investor? What particular co founder is a good co founder? What particular employees a good employee? What particular customer or partner distributor? Is a good distributor? Having a thought about how you evaluate that? What risk do you attach to the fact that if you cannot trust them? What is the worst case that look like? That is an interesting book. It’s a little sad, but it is very honest. He wrote most of themself, at least according to what the commentary is. And it looks like that. So that means there’s a lot of foul language attached to it. Then the last one would be and I think that is where our circle starts overlap Shoe Dog by Phil Knight, the founder of Nike. Read it for two reasons. One, the first 300 pages, it’s just a good story. You can read it in a single setting. And you just getting to the end and thinking you know what? I’m surprised. There’s something called Nike today, because there was seven reasons for this to not exist. So I am completely baffled. Because at no point did he really wanted into existence, at many points he wanted out of existence. So it’s just an interesting book. Now, what I want to point people to is the last really 510 pages, if you read it, he almost between the lines, given his son dies, suggest to people who are about to embark on this particular journey to at least take a step back and ask themselves. Are you sure it’s worth it? Whatever the journey, I’m not just talking about the intrapreneurial journey. But whatever journey you’re about to embark on, allow yourselves at least a moment to deliver it whether is it worth it? I think what he’s trying to tell us or at least that’s how I read the last few pages, that he’s not entirely sure that it was worth it for him. And you can read throughout the book that he had one child that was likely no wife, not the kids, not the house, it was just Nike. And that is also a little sad. So all these three books have kind of semi sad endings, but I think good, strong points to make today. pre written books.


Scott D Clary  59:49

I love it. Thank you very much. Those are good recommendation. Never heard those recommendations before. I’ve heard of I’ve heard of Shoe Dog. Mike Tyson, the book by Mike Tyson. What was it? What are the titles of the book by Mike Tyson just saw? Do you remember? I can look it up, but I’ve never heard. One. There’s only one. But there’s still amazing recommendations. Um, lastly, how do people get in touch with you if they want to reach out?


Dennis Mortensen  1:00:18

I am everywhere on the internet. So if you look up Dennis Mortensen, on any platform, there’ll be a picture of me, and there I am. And if they want to go wild, I’m on Dennis and That’s my email. If you got anything to say, email me, I’m an inbox zero kind of guy. So I’ll get to it.


Scott D Clary  1:00:39

I love it. Alright, that’s all I got. Thank you very much. I really appreciate the chat. It was really really good. As always, this has been another episode of the success story podcast. If you haven’t already, please like, subscribe and share with your friends, families, peers, or co workers. You can leave us a rating it’d be much appreciated. Any rating is fine as long as it contains five stars. And you can always stream or download this podcast on any podcast platform and you can also catch it on YouTube. As always, have a great week. Have a productive week and we’ll speak again soon. Bye now.

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