Dennis Mortensen: The Serial Entrepreneur’s Journey

What does it take to be a quintessential serial entrepreneur, and how does it feel to have founded and exited multiple startups over nearly 30 years? In this episode, Dennis Mortensen shares insights from his nearly 30-year entrepreneurial journey, highlighting the importance of clear communication, setting realistic expectations for employees, and the necessity of strong sales skills for founders. We also explore his latest venture, LaunchBrightly, which automates product screenshots to keep help websites up-to-date. Don’t miss this conversation, tune in now!

Discussion Topics: The Serial Entrepreneur’s Journey

• Introducing the quintessential serial entrepreneur
• The things that got better with time
• Working at X.AI
• People’s reaction to AI in workplace
• His latest venture – LaunchBrightly
• Important leadership qualities at an early stage startup
• Picking apart your ideas
• Dennnis’s Happiest exit
• Looking back, what would Dennis have done differently?

Transcript: The Serial Entrepreneur’s Journey

Alison Eyring: Welcome Dennis. It’s so fantastic to have you back for an encore performance on my Growth Leaders Podcast. I love interviewing you. For our audience, you get the record in my book that you’ve founded six startups, and you’ve successfully exited four. You did have one failure, and you have one in progress, which is LaunchBrightly, which we’re gonna talk about later. So in my mind, you are the quintessential serial entrepreneur. How does that feel?

Introducing the quintessential serial entrepreneur

Dennis Mortensen: Very nice words. Thank you very much. But you’re also giving away my age because I’ve been working on this for the last 27-odd years, so it does take some time. We spent about five years on average on each venture, but all I’ve done my whole life. It sounds very dramatic when I say it out loud, but that is it.

Alison Eyring: So for almost 30 years, this is what you’ve been doing, right? The first time was in Denmark cause you’re Danish, right? And now you live in New York. Are you still motivated by the same thing or has it changed?

Dennis Mortensen: It’s a good question. I certainly always had the belief that entrepreneurship could be a lifelong career. There’s the idea that entrepreneurship, it’s something where you see a pain that only you believe can be solved by your efforts, and you must do it and you might win.

I do think like anything else, if you turn it into a lifelong career, You should probably be better at number two than you were at number one and a little bit better at number three than number two.

So over time I become a little bit more confident. I do think if I close my eyes and think back, I just wanted to make some good product or we’re gonna see the joy of somebody using my software.

I don’t think that has really changed much. And it’s not that I have some grand M b like a master plan of here’s the market, here’s some kind of capital. I’ll go invest. I can see two or three steps forward. I get some sort of exit, a few extra monies in my pocket. Nah, I just see some pain. Can I make some software?

Those users are in less pain now. They’re happy. We do a few kinds of high fives and all is good. 

Alison Eyring: So it sounds like your motivation wasn’t, I’m gonna get in there and I’m gonna sell it and become this multi-billionaire, and it was, I’m gonna build something cool and make people’s lives better.

Dennis Mortensen: So I had my computer very early on. I did game development throughout high school and college for beer money and so on, so forth.

Every single kind of subject matter that had anything to do with computer science, I already had 10 years experience because I was just one of the geeks on that particular street and there were many of us.

I learned from day one, do my homework. So for me it was always about just packing away on something on the evenings or the weekends, because I’ve done that for 10 years. Prior to university, you do it for half a decade at university, and then you just continue after university as well.

Alison Eyring: I wanna go back to something you said that you said you wanna be better the second time from the first and the third over the second, the fourth, et cetera. If you look over across the different companies that you started, what did you learn?

Dennis Mortensen: I would say one thing I’ve become much better at, and there’s a thousand things by the way, and there’s a thousand things I still need to learn, but one thing I had too much of. I don’t know, halt, like expectation on my employees early on versus that of, as in I was just emotionally drained when I lost an employee, like visibly disappointed as in borderline.

You betrayed me. Oh, they didn’t, Dennis, as in, they had a job. They did some good work. You paid them some money and that’s that.

But I became much better at just packaging good little kinds of travels from team members that I get and not having that whole, we are now shaking hands on a lifelong relationship.

Alison Eyring: I think it’s pretty significant that one of your most profound insights is such a human thing. It’s not about products, it’s not about going to the market. It sounds like it’s a lot about your maturity, so it’s less about you and what you’re doing with people. I really love that. 

Working at X.AI

I spoke at a conference that was about ai. So of course it made me think of you because you are the data. Man, and I met you when you were working on X.AI, which you just mentioned. I just wanna go back to that. I had such a fun time in my life. It was the first time I’d actually had an AI assistant who I named Amy.

And I have written blogs about Amy. That was how I met you. I did. Talk to me a little bit about what it was like exiting that company because that was something that you really loved.

Dennis Mortensen: I think it’s gonna be very hard to do anything for a long period of time where there’s no guarantee of safe arrival if you don’t love doing it or press put in another way. You almost have to start up for the love of the sport.

The most likely, or the default outcome is you try and you die. So you should at least have some fun along the way if you don’t. Why are you even doing it? So in that regard, I think I’ve been equally excited,

And we certainly thought back in 2014 when we started X.AI, the prospect of a possible intelligent agent that can schedule meetings on your behalf will be fun. Exciting and challenging. I worked on it for those six years and ended up with some good products.

AI was a bottoms up Slack, Zoom and similar, which is that there’s a free edition. You go use it, you might fall in love, you upgrade to the pro edition.

You like it, you introduce it to a colleague. Before we know it, we solve a team edition. And here we go. And in that setting, you are aggressively exposed. To a very large number of users versus a more kind of traditional B two B setting where it is equally exciting, but there’s not as much chatter on Twitter and elsewhere, or X as it’s called today.

But this was fun. That was the one part, just a lot of people talking about it, which kind of made it exciting. The other part is that we ran these, at least initially, a thousand touring tests every day, and we won some of them. And you know what? A little bit of joy in seeing people converse without an agent.

Get to the end, see a meeting being injected on their calendar, not even knowing that this was an ai, just assuming that, Hey, for this meeting where I’m bringing a sandwich for Amy, Damn, that was a machine. It was joyful. Absolutely.

Alison Eyring: It was fun. I remember having people discover that Amy was not a human, and they were so surprised.

What did you learn about humanity when you introduced AI into the workplace and into their work?

People’s reaction to AI in workplace

Dennis Mortensen: A ton. I’ll give you a few here. One, I thought the expectation of the agent would be similar to that of humans doing the same job. That was not the case. As soon as you introduce machines into a job, you get super human expectations, so I could not just do as good as a human personal assistant. I had to do much better.

So Microsoft did some research that shows that the willingness to forgive machines, it’s just at a different level to that of your willingness to forgive humans.

If you have a colleague, they make a mistake, you speak to them, you forgive them. They continue to work on whatever kind of project they’re working on, a machine doing that might just get terminated, and we saw that. So that was the one part. The other part was as soon as you introduce machines into a kinda human or human-like negotiation, machines will make machine mistakes and humans will make human mistakes, such as you might forget.

There’s only four hours between New York and London over the summer for two or three weeks because we cut our summertime in different days. Oh, yes. Happens to the best of us. Very human mistake. Those are not the mistakes the machines make that they just do, with a hundred percent accuracy all the time.

Lastly I thought incorrectly, at least initially, that it will be of value to humanise the agent as in make it a part of the conversation on similar terms to that of the other participants that worked against us. As soon as we became more clear about this it is a machine doing a human-like task, but speak to it and expect machine-like responses.

As soon as we made that public front and centre, everything worked. Much better, even to the point where we actually skipped the idea of naming the agents. They were called Amy Ingram and Andrew, and we moved to a scheduler. Just a change of email actually increased the accuracy.

And there’s two types of lies that we’ll see. One, the unintentional lie because you are a human. So you’ll say things like at 2:00 AM deni. Let’s meet first thing tomorrow morning. What you mean is this morning, as in you just haven’t gone to bed yet, so it’s very human to use the word tomorrow up until the point where you go to sleep, but tomorrow already arrived.

So I now have to figure out what you say is not what you want.

Then there’s other lies, which is that you say something, which is true, but not what you want. Let’s meet first thing next week. Then we set up a meeting for Monday, 8:00 AM which is within your preferences. Everything is correctly predicted through and honest and inserted. I said the first thing next week, not Monday at 8:00 AM So in short of 20% of all instances, one in five they would immediately correct the agent. They actually figured out how to use it as a feature in the end, but we had to train them as in Sure, they want what you want.

Alison Eyring: It really illustrates the complexity of language, doesn’t it? I wanna go forward to where you are now, which is with LaunchBrightly, which I love. I can’t wait till I can buy it. Talk to us a little bit about that.

His latest venture – LaunchBrightly

Dennis Mortensen: It is always super nice if you can end up working on a particular problem or pain point that you yourself have. Then you only have to assemble through interviews and what have you, some level of empathy for somebody else’s pain.

You can just look at yourself and say, you know what? This I don’t like. I wish somebody would come along and fix it. So if you run any SaaS product and you put it to market, you need to support it.

You would like some sort of self-service, which side note all your users want as well. They don’t want to email you. They don’t want to chat with you. They actually don’t want to talk to somebody in customer success. They just want you to give them an article that shows them how to set up that two-factor authentication, which might be a little bit complex for that.

You write some support articles, and in those support articles, you add some product imagery. I will guarantee you anybody listening to this and anybody who I know, those product images they do manually, and I’ll tell you how they do them. They log into their demo account in some Chrome browser. They sit on their Mac, they navigate to that particular page.

They find the particular feature they wanna have a look at. They do a little bit of inspecting elements to remove some noise on the screen. They click perhaps some dropdowns to show what they want. They do a command shift. Four, do the little rectangle, the whole thing lands on their desktop. They might annotate a little bit, a little kind of rectangle around it, a little arrow.

Look at this, please. Once they’ve done that, log into Zendesk. Find two or three articles where that image exists, replace those kinds of images and they’re done with it. That particular process is nice, not difficult, but you have to do it for every single person as in this is the, it’s not like you say, Hey, I support half the features in our product. No, you have to support all of them.

Sure, you have your big marketing launches, but you make changes all the time. As you make those changes. Those product images that I just talked about, they slowly rot, meaning that what you have in your help centre, in that knowledge base is just slowly rotting, getting ever more disconnected to reality.

So what I wanna do is to turn that into a machine process where if you change your product, I will log into that demo account. I will take all those screenshots and all those particular modes you want. Desktop, light, desktop, dark mode, mobile mode, and what have you. Save them to the cloud, have that whole bucket of images, log into your Zendesk and replace all those kinds of images.

So if you change your product, I update the whole help centre and they’re just in sync at all times.

Alison Eyring: Automated product screenshots. It’s definitely a lot of energy, right? We feel that at Produgie because we have so many ongoing changes and so many different stakeholders on the system and so many different use cases and applications, and so user enablement is really important.

And that is having it not be confusing to people. So I think that that is definitely a problem. I can’t wait for you to solve it.

Dennis Mortensen: I’ve become so cocky of late that I would kinda do research.

Now I don’t do any research, so we speak to somebody on the phone and I’ll say, Hey, let’s log into your demo account while we do that. Lemme go help dot your company name.com. I’ll go into any article. I’ll go have a look at those screenshots. Let’s find that in your product. And there’ll always be a disconnect.

And I’ll say, ah, Danny, it’s just, yeah, I know. I changed the kind of nav or the dropdown and yes, we have more options now.

As in there’s probably some inflection point where you are sabotaging your support as in they came here for clarity or side note by the way. It’s not like people are arriving at your help centre in some sort of ecstasy of joy. Now they arrive with a little kind of bag of disappointment, which is that I hate the fact that I couldn’t figure it out in the tool, but that’s okay.

It happens on other tools as well, but I’m not super excited. I at least found the right article. If that article is not easy to follow and those screenshots are not up to date, I’m not gonna get any happier. I might just reach that point of disappointment, which is just a long list of disappointment, right?

I still love listening to you because I think that you’re so different in that you really have this thing of, starting and going. You have a business, you have an idea, you have a product, you build a team, and then you go on.

Alison Eyring: It’s like you embody entrepreneurialism, right? What are, do you think , leadership capabilities that are really important at that very early stage? And if so, what are they?

Important leadership qualities at an early stage startup

Dennis Mortensen: You’re certainly right. Zero to one Part of the journey is very different from the one to two, two to three, three to four, so on and so forth. And many people hate the zero to one ’cause it’s just a bag of uncertainties. We don’t have the full team yet. We don’t know if the pain is completely true.

We don’t have any users, customers, revenue, finances, prospects. The whole thing is just kind of bordering on dead on arrival, right? But that challenge I find almost romantic.

You can fake many things, right? But one of the few things you can’t really fake is enthusiasm. It’s very hard, as in people catch onto that for where, I don’t think you’re excited. You say all the right words. That’s not excitement, but people who are excited, that guy, let’s do something with him.

Then I think the other part is it is on you to be able to see a few steps ahead because you have all these unknowns and for where you must at some point be able to see something that other people can’t see, which is that we still just swimming out, not towards shore, but the other way.

But I see something out here which we can hold onto. So if we can just get there. That’ll give us a little bit of breathing room. But you must be the one who can see that. And if you can’t see it, it must be your bravery or whatever you wanna call it, that at least suggests this is the direction we’re gonna go in.

It feels right. We might all die, but at least let’s go in this direction. It’s our best chance. So that is something for where that particular pain point that you picked, you must be able to see clearer than anybody else. I. Just rewind a little bit where I’m, it’s not a cheat code, but I spend an unfair amount of time pre or beginning any venture in trying to invalidate the particular thing that I’m starting on.

Your job is to kill almost all your ideas so that only the special ones survive. So I have this whole, key process for where my finest job is to create obstacles for where the ideas can’t really pass.

Those are some of the qualities. Then of course if I was to add just one last one, sales. If you can’t sell it’s gonna be hard.

You at least need to team up with somebody who can sell because your whole job as a founder, even as a technical founder or kind of product-led founder, whatever you wanna call it, is sales. You’re fucking selling everybody all the time. You’re selling investors, market press candidates, employees, your wife, your kids, the world.

You’re selling everybody all the time. And if you’re just not either good at it or don’t enjoy telling that story on repeat you’re just gonna, you’re just gonna drown. That is, say, a skill that somebody in the founding team must have.

Alison Eyring: Yeah, that I will like. The whole comment about really picking apart your ideas and really trying to find the holes in them before you start. I just think that’s so hard for people to do because it’s, people wanna believe in their idea, they wanna believe it can, they can just work hard enough, and I feel like that’s just this very hard realism that is so important because then once you pull the trigger, you really go for it, and then you really have to be able to help people follow you.

Picking apart your ideas

Dennis Mortensen: I’m of the belief that if you start. That’s only two ways we end, as in we win in some capacity or we lose. As in we just exhausted down to the last penny.

I’m just not a big fan of the idea of, yeah, we’ll pivot three or four times. No, that’s not the mission we’re on. That’s actually not what I hired people on. As in we shook hands on us going in this direction and halfway there, me suggesting we could go in another direction.

Then we are not mission-driven, then we’re just in it to make money. And I’m not sure I’m in it to make money. I’m in it because I thought this was a pain we could remove. And you know what? We just couldn’t. And that’s okay.

I’ll give you one process I use before we start. So I have this setting where I invite a handful of friends, near friends and experts.

Their job, their only job is to come to not really be super prepared, but just come with their kind of expertise and kill the idea as if they should see themselves as successful. If they can shoot down my ideas, I, and I don’t want your love. What I want you to come here and tell me is this idea is shit. And I’ll tell you why.

First of all, I’m a data scientist in this particular kind of area and you, your ideas then say, are just not solvable. I am. That’s a 10 year research endeavour. I said, how dumb can you be? So that’s their job. But if I can survive that, which is I spent a couple of months preparing for it, if I can survive that, okay, there might be something here.

If I can’t, Denis, these people came in, killed it in three days. Lucky you didn’t do that idea, and you spent two months if you can’t even defend it, it’s just not worth doing. And I’ve had the ideas who died on that, that I still love to this day, by the way.

Alison Eyring: I love this. But I’m just imagining it for myself and thinking about how hard it would be for me, but also how incredibly powerful to just invite people to kill my idea. And I love the idea that if you can’t find a way to, to justify it, You let it go. I just think that’s so incredibly powerful.

Dennis Mortensen: Oh, it’s hard. But that’s the promise I’ve made to myself.

Alison Eyring: You said similar themes from last time, but I really love that story about having people poke apart your ideas. It’s just so powerful.

I wanna ask you about your exit, that was your favourite. What was the, what was your exit that you, that left you feeling the happiest and why?

Dennnis’s Happiest exit

Dennis Mortensen: They’re all special. They’re all your kids, right? However, the first exit where you go from, I might just be an entrepreneur too. This could confirm I am an entrepreneur, it is special and unique, right?

And I certainly remember that first exit vividly. And the kind of joy that came attached to it. Like many other things. I remember the second exit part of the deal terms were that I moved to New York, which I did.

I remember I have a picture, me, my wife, my two kids, this empty apartment, and I remember that joy. We had a little picnic in the apartment and you know what, no matter what happens, I always have this place like, you know what? I can just sit at home with my laptop and diet codes like I want in life already.

And I just felt a ton of freedom in that particular moment. But I think many things the first time gives you a, at least a unique amount of joy.

Alison Eyring: Yeah, just a sense of accomplishment. It’s so fun to listen to you describing that. I just wanna ask you to look back now, like 27 years starting so many different businesses.

If you look back, is there anything you would do differently and what would that be?

Looking back, what would Dennis have done differently?

Dennis Mortensen: The funny thing is there’s plenty of things I believe I could have done differently, which would’ve had that one startup. We did not fail. So the idea was obviously very good. So we got started on a delivery platform. Think GrubHub in Europe.

It’s a massive idea today. We all use that particular product two times this week, right? In, in some capacity. So I have plenty of ideas for how I could have done that differently, but now I might just be telling myself lies and you can tell me that then it’s now you’re just singing a song for yourself.

But you know what? Me failing on that was the one thing that got us travelling as a family.

We spent four years doing a venture in Budapest. We ended up in New York, So if the default outcome is that it doesn’t work, then it can’t be seen as a failure. It’s really just you run an experiment and you have some sort of hypothesis for what the outcome might be.

It didn’t turn out to be that. It’s still a good experiment though.

But yes, what could I do differently? It’s a good question. It’s been a while. Journey. I could have certainly taken the one we failed. By the way, this is a funny story if I’m just being very specific.

We did have an m and an offer, which I declined because I thought they ended up being, do they own GrubHub today? I think they do. It was a European company. They just became the biggest in Europe. We did have some m and an offer with an ID client, which I thought we’re just a better team. We are just in a little bit of a rough setting right now, but hey, I’ll solve it.

But we didn’t. And they won, but I can go back and say, Deni, you should’ve taken that. But that’s fine.

Alison Eyring: It sounds like that it was a business failure, but it was a life success.

Dennis Mortensen:  That’s exactly what it was. Yes.

Alison Eyring: Yeah. So I really love that. Dennis, I’ve loved having this conversation with you back in your encore visit to my Growth Letters podcast.

It’s wonderful to hear about your new venture launching brightly. I’m super excited about it and I can’t wait to hear what happens next with it. Thank you so much for taking time to talk to me today.

Dennis Mortensen: This has been fun. Thanks.

Our Guest: Dennis Mortensen

Dennis Mortensen is a serial entrepreneur with a track record of founding six startups and successfully exiting four of them. With nearly three decades of entrepreneurial experience, Dennis is known for his passion for solving real-world problems through technology. Dennis’s latest venture, LaunchBrightly, reflects his commitment to making products better and more user-friendly.