Hi everybody. For many of us, public speaking is terrifying. It's not something we look forward to. But then there are those who love public speaking so much that they decide to make a full-time career out of it. So to talk more about the life of a public speaker, I talked to Dan Tuperov, a professional keynote speaker at various events who I worked with in the past who is an excellent product manager and product leader to learn more about what is it like to be a professional public speaker and answer a bunch of questions ranging from how do you come up with topics to discuss, what the logistics of this look like, and more in this really fun chat.

So stick around. Dan, it is great to meet you. And so for those of you listening or watching, I met Dan in person multiple times. He used to work at Google on the same team I was in. So it was great to connect with him then. And now I've been following Dan online for several years as well. A lot of interesting things that we'll talk about on that front as well. So Dan, thank you for taking the time to chat. Awesome.

Thank you Kupa. Thanks for having me. Uh it's been an exciting time. uh you know the last couple years have been really really uh crazy and great at the same time. I'm looking forward to cracking some of those things open and talking about how change is changing all the teams in the world. So yeah no excited

and you know we'll definitely touch upon what happened the last couple of years but I want to go like I always like to do with all my guests can kind of go back to the beginning and ask what made you get interested in getting into tech the whole tech field and all the stuff

that went around it. Yeah. Yeah, for sure. It's it's a pretty there's a pretty definitive pivot point for me. Um, a long time ago, I was actually uh when I was in high school still, I took a couple of drafting classes and I it was really fun for me. Uh, I heard a little bit about architects and what they do in the world. And designing buildings that you could drive down the street and look at and see like see this building, I made that. like that that sort of permanence to the work as an artifact was was always really enticing to me. So I um my senior year in high school uh was I got an internship at an architecture firm and this is 1986 and

um at the time architecture was like a drawing on paper kind of a job right sometimes you know you'd be drawing on on what they called myar which was like a almost a plastic film and you draw in ink so that it would stay stay wouldn't get erased um and you know we had these drafting boards you can imagine them. You've seen them before. The slanted desks with a ruler like attached. Um, and I'm sitting there drawing for I I started January my senior year and I worked there through that semester and then for the summer before I went off to college. My my intention was to go off to college and become an architect. And um I'm I'm as an intern wandering around meeting some of the architects there.

They gave me some jobs to work on, but but those jobs as an intern, as a 17-year-old kid, pretty much they will all the only thing they'll let you do in an architecture office is draw the lines in a parking lot on a plan. So, they would they would draw some building with the this huge triangle-shaped parking lot, and they would say, "Dan, tell me how many spaces we can fit in this lot." And I would figure out where the medians go and figure out if it had one entrance or two. And then I would draw the lines over and over and over again. And um I spent months drawing parking lot lines.

And one day I'm putting the plans in a storage room. Um we have those flat those flat file uh filing cabinets where you store big plans. And I'm putting some plans away and I meet this one guy who I'd never seen before. I introduced myself and he introduced him back and his name was Mr. Pac. P A K. And he um he I said, "How come I have never met you? I've been here three months." And he said, "Oh, because my office is down here because my plotter makes too much noise." And I said, "What's a plotter?" And he said, "Come here. Let me show you." And I he goes I go in his office and he's got a drafting board just like everyone else did, but he also has a

computer and this this big printer thing that that it's hard to even describe how it worked right now. But he showed me how it worked and I could copy paste parking lot spaces on this computer. And we say the word copy paste all the time now, but in 1986 that was magic to just draw something one time and then say plop plop plop plop plop. that that saved me weeks of work and I just knew this computer was going to completely change the face of architecture. So I changed my major immediately and started focusing on computer science and and now I you know now I try to change every industry with little copy paste things um so that they can all work more productively and faster.

Did you go into computer science to continue to do more architecture work in a digital form or did you end up wanting to do something different once you got

into No. No. like instantly. Well, first of all, as a naive kid, I thought, okay, well, architecture has already been fixed now. So, I should I should figure out how to figure out how to take computers and and fix other industries. Um, and so I went into computer science thinking like, okay, well, our job as computer scientists is just to go from industry to industry and figure out how we can help make them more productive. Uh, and so one I didn't I didn't so much care about architecture design because Autodesk already made it. Um, AutoCAD now existed and I figured, you know, they would keep working on it. I've always thought about what it what it would have like been like to have gone to Autodesk and worked. Autodesk makes

auto uh, you know, architecture software for those that don't know. Um, and that would have been pretty cool, you know, convergence of fields, but I I never really I just sort of abandoned architecture as soon as I saw that computer science could change how people worked in that massive way.

That's pretty funny. You know, that I have a similar story in some ways. You know, when I was in high school, my first, you know, we had like options of classes you can take beyond your core classes you could do. And the only thing that seemed remotely interesting to me was drafting, you know, which was like one of the precursors to like, you know, some of this work. So drafting one was I'm literally on the board using the slide rule like the the one where like you know the horizontal and vertical rulers and drawing lines on paper and learning like you know how to do angles and measurements and you know going from like small sizes to big sizes and scales between them and so on. But you know the

next edition like drafting too I forget it was called that was on autocad and so that's when you actually like do all the work you've done here but now you have this like you know you see this like white blank virtual grid with like small dots in it and you're like okay let me just the dots do snapping properly. So when I learned snapping that was a huge life changer because I didn't know that. So I'm like you know I'm working on like either centimeters or feet or some arbitrary value but the dots were like in a different value. So I'm like trying to line up in between them. Once I figured I could customize it to actually make the actual snapping match the unit

of measurement I'm using, that was a game changer. So for me when you said like you were, you know, you were like drawing lines manually, but then you were like on the computer I can do lines this way. That to me was like taking a real life thing and being able to make it smaller and use the plot lines to convert it. Yeah. Yeah. Yeah. That was huge. And for whatever reason, I think that was like new enough. And the the city I was in, they had all these like legacy plans of like things that need to be digitized. And so like who better than children who are learning about this because that solves multiple problems and you know and they can do this. And so I remember like looking at

these plans of like I think it was actually like an intersection with like a sewer line a gas and all these things be underground. It was like like little piece of paper. And we're asked like, can you make this all into like a digital form? And that was my first foray into I guess like what you were describing here. I'm like, yeah, I can absolutely see this connection between this physical world and then the computer world makes this a whole lot more accurate, reproducible, sharable. Now it's archived somewhere. So it's no longer a case with the paper were to get, you know, burnt or water damage or just disintegrate. You still have all this going. And so yeah, so when you were describing the drafting story, it

reminded me of like my time doing very similar things. Of course, I didn't do that beyond it after that. You know, there was no drafting career and I went to college and I did other things, but it is fun that there's a connection there. Yeah, that is that is amazing.

and and yeah, drafting was one of those things where in high school um you know, there's electives. There's like there's the classes they force you to take and then there's the electives and drafting was one of the only things that was like an elective that could also be a job when you right and and so that was that was just super enticing to me. I was like people choose to do this. They're not forced and that and often time you walk by the rooms where the drafting class is taught. It was very different.

Right. It wasn't your traditional classroom which just like repurposed like things in the whiteboard to be different. It was actually like a different arrangement. You had larger desks, you had chairs, you had it was very different. So you were like, I want to try this out because who knows what's going to be there. Right. Right. Right. Yeah. Yeah. Yeah. Anyway, so that's where I got started. You know, I little by little went into computers. Uh uh and then you know that I started work in the 90s. You know, 94 was my first corporate job. and they had just got PCs for the first time and they were transitioning from old mainframe computers like dumb terminals where the computer was in the basement. We just had keyboards. Um, and

you know, for me that was that same thing. Hey, we're getting PCs here. I'm going to help you figure out how to use these to do your work. And then we got the internet and then we got, you know, mobile phones and then we got cloud and then we got like data science and then we got remote teams and now we have AI. For me, this is just like the seventh transformation in a long series of transformations that's never going to stop.

So, you studied, you know, architecture formally. Was there a fear that you were basically had all the sunk cost in having studied architecture, but now you're embarking on a career that does not really use that in its literal

direct sense? Um, I so f first of all, I I did ch I changed my major in school. So I worked um you know a couple years on trying to get an architecture degree that well when I tell the story it seems like this binary switch and it was in my head but I didn't actually follow it with my body um right away. So I you know I started working on architecture and um you know I would do these drafting classes and you know model building and all these things and I was doing okay at that. I was like a C B minus student in that stuff and then I would have a CAD class and I would like just plow through it. It was great. Um

and then I took some other computer classes and little by little I realized that computer classes are just way more intuitive for me than the other things. And so you know I sort of gradually uh you know my architecture triangle got smaller and smaller and smaller while while my computer science triangle got bigger and bigger and bigger. And um and I always realized, you know, the learning how the old thing was done made me better at finding the the product value in the new things I was trying to build. Um so I never never really thought of it as sunk cost. I always looked at it as as ways of learning how they used to do it so that I could preserve the things that were important

and automate the things that were boring and slow.

Makes a lot of sense then. So from there, how did you choose your first job to formally work on after getting your

computer science education? Yeah. So um that was uh that was kind of you know serendipity uh a little bit. I was actually still in school. I had been go because I changed my major halfway through. I was on like the seven-year plan for for uh for bachelor's degrees. And um so I'm going to schools, taking classes during the day and one day I saw in the newspaper before we had Monster uh we used to look for jobs in the in the Sunday paper and uh there in the one ads there was a job for a computer operator and it it essentially said computer operator will train works nights and I was like I can still go to the school it says computers I like them

uh they're going to train me so they need nothing from me and I went there and I you I had had applied and and got the job and that was really the only thing I had applied to do that was a real job and I was still in school so I wasn't really like on my um on my job search yet. I wasn't like doing career fairs and stuff like that because I you know I was still just a junior in uh in college. So uh uh I started doing that and then I stayed working there as I finished school and and um kept you know doing more and more computer stuff as they went through their PC transformation and you know I I spent 10

years at that place and uh they bought a software startup and I went to to help run it and that's what really got me onto the software side of things. Yeah.

As an aside you just mentioned Monster. I had no idea if they're still around. I remember like wait that's where people applied for jobs back in the day. I remember when I was in college.com was

the place you went to. Yeah, they're still around. I didn't realize that. Yeah, they are. There's kind of an interesting story uh that also overlaps on my resume. Um before Monster.com, there was a company called Telephone Marketing Programs. They were a company that managed and sold advertising in the Yellow Pages phone book, right? So, you know, before we had the internet, we would get the Yellow Pages and thumb through and look for plumbers. Um, you could also thumb through that and look for jobs. And this one company called TMP, Telephone Marketing Programs, started making job boards in the yellow pages. they were local to a zip code, right, or phone area code, and they they were all the things that were great about job listings now. And so TMP started

creating job um boards that became such a successful part of their sales business that they spun it off and called it Monster.com. Then 2000 happened and Monster.com exploded. They made so much money they bought TMP, their former parent company. And so Monster.com became uh the parent company of their original TMP. And 15 years after all that happened, they had split apart again. And I went to work at TMP, which was the original company. And they were still doing like recruitment job board sites for people. Uh you can still look them up. Actually, no, they've changed their name now. It'll be in the speaker notes later. I forget the name of the new place, but long meandering uh career path for me. and it did overlap with

Monster. That is amazing. I I always knew that Monster.com I I vaguely remember TMP because for whatever reason I just like to dive into companies just for the you know fun of it and I remember reading it was a long time ago. I did not realize that you had direct connection with that particular Right. Yeah.

Anyway, so one of the things you've you know I looked to your career is that you mentioned earlier about how you I like to identify problems that needed to be solved and how computers can help solve them. And I think that probably played a big role in the the career path you took. You know, you've been in product management, you've been in consulting and you know, all these various areas. And so walk me through a little bit of that. You know, when did you decide to go from in some ways like working with computers and like helping people in a smaller scale to then trying to have impact on much larger scale because you worked on various roles where you're you know defining a large part of strategy

for a company and and things like that.

Yeah. Yeah. Um, so I think first, uh, intuitively I just always was a product manager. Like when I was doing homework in junior high, I was looking for ways to do that homework more efficiently, right? Um, when I was working at McDonald's before the internship in high school, I was looking for ways to, you know, do our stuff at McDonald's more efficiently. I was always just a problem solver. It's just fun for me. It's like a puzzle that you're trying to solve. And little by little, you know, I started I started majoring in computer science and started programming as a developer for that first company that I worked at. And you know, for that my first developer project was I was a solo developer by myself on a project. I was

assigned to a sales team and they said, "Hey, just go work with this sales team and make stuff that will help them." And you know, so I started building a CRM system for that team at the time. They were all managing um I have visual aid. Yeah, absolutely. Bring it on. They were all managing their day in one of these. This is called a Franklin planner for anyone that's, you know, under 50. Um and they would just write all their customer notes in this book and they would keep track of their calendar and write their to-dos and all this stuff.

and then a salesperson would quit or get fired and they would take this book with them and you would lose your entire sales history with that client and the new client would the new salesperson would have to start over. Um, and so I built a CRM system that digitized that book. Uh, this was before we had um salesforce.com or anything like that, right? And so um I had four users and that was it. my four salespeople, they would put their stuff in this thing and then, you know, we could transfer accounts and all that stuff. Um, so I was a developer. They didn't call me a product manager back then, but you know, my first day I went up to the sales guy and said, "Hey, what's your biggest

problem?" He's like, "I don't know. I'm about to go visit this customer and I have no idea what the last person said to them." And so I made something that solved that problem. And that's little by little I realized that was the fun part of my job. Not programming and fixing my own bugs all day. Uh so you know little by little I started asking more people what kind of software problems they had or what kind of problems they had and tried to think of you know software solutions for those problems. Really just been doing that my whole life way before we used the word

product manager. So essentially customer solving the customer problem was your destination for you. everything else was just like the way you got there. So, programming, all those things were So, speaking of programming, what language

do you write your CRM in? Uh, way back then it was um Visual C++. So, I had learned C++ as first C and then C++ in college, but most of that was mainframe development stuff back then without window interfaces. And so Visual, now it's Visual Studio and the whole .NET framework. When that first started coming out, they created Visual C++, which was essentially the C programming language, but with Windows that you could, you know, draw and articulate and then automate. Uh, that's what I that's what I built the CRM in. And, um, I still have I still have that on a floppy disc somewhere.

Was the UI language windforms?

um you know that I can't remember it might it it was just from Microsoft you could literally buy yeah visual visual C++ and Microsoft probably like got that package from somewhere I I don't

actually remember that the reason I ask is that you know visual basic was one of my first programming languages like real programming language you know I learned flash of course my first one but no one considered that a real language so visual basic was my first one and they had a form designer you know you had like a you had like a place you can like similar to the AutoCAD the the form had like a window layout doc again where you can like lay things out and space things around and so on and I always was and at that time I think it was like windforms is the name of that technology then it evolved into WPF and then all the various versions of it beyond that but I

always curious to ask because some people actually did not like using that UI designer for it so they wrote everything in code you know just like in Java you could actually write your entire UI in code where you're writing mathematical numbers and then that transit into visuals. So I was kind of curious to know if you fell on that spectrum if you actually were happy to

use the designer. Yeah, I was happy to use the design tool because I was always sort of a visual person as an architect. Yeah. Right. Draw drawing out like I could picture the thing in my head and so drawing it was a way easier way than

um than Yeah. than Yeah. I had to cut an interview short if it had if you were like no I actually wrote every line. I defined a button by defining the rectangle coordinates and I literally plopped it in and I recreated everything on input and so on. Right. Right. Right. Yeah. Yeah. Yeah. Yeah. For sure. That makes a lot of sense. And so from there, you know, at some point you you went from like I need to write programs as part of solving customer problems to then becoming a formal product manager.

Was that transition more natural or was it something that required more careful

planning on your part? It was it was pretty organic. So, so mostly what happened was I had worked on I had worked on that CRM system for about four years. Uh during those four years we were shifting from C visual C++ over to Java because that now we were needing web applications for our internet and stuff like this. Um, and so first I realized, you know, I I just got good at Visual C++ and now I'm like trying to understand classes and and Java, the Java framework and and all these all the calls and and puts and and all all the all these things that um were foreign and new for me. And at the same so I'm now I'm struggling as an early Java

developer. I feel like I'm starting over, but at the same time, I'm like eight years into my seniority on the IT team at this company where I'm working and I know how all our teams work and I know all the people that are involved and what's important to the business and and so other software engineers were starting to rely on me for making our documentation like doing the problem solving, the analysis, writing that, you know, I I at first I called myself a business analyst, right? I was like, "Hey, we don't have a business analyst on this project, Dan. Can you help us for a bit?" And I was like, "Yeah, sure.

I worked with that team for for years." Um, and so I sort of gradually just ignored getting better at Java and focused more on helping people with the documentation part of the work. Um, and then then I started to figure out road maps and I um I went to a company uh there was a company way back then called constructs uh which doesn't need to sound familiar to anybody but one of the one of the leaders of that company was one of the people at the at the meeting in in Colorado where they had the agile manifesto meeting.

So like four years before the agile manifesto, I took training from I forget the guy's name, but uh but and that was I just I just was really interested in how software was evolving and how people were going to use it and I got good at at at listening for customer problems and then translating between that business to the development team that didn't understand the business but they understood how to program in Java. So I became that that translator guy.

That's very fun. And and from there at some point you went to Autodesk, you went to McKenzie, you know, what was the you know what what made you what made you change companies in some ways? Because it seemed like you've been a company for 10 years. You've been in many companies for a long period of time. So what was often a forcing function for me to go okay I think I've you know reached the you know what I want to do here. There's something really new and interesting coming on. I need to actively do something different.

Yeah. Yeah. Super easy answer to that question. Um, as a product manager, you can with some amount of skill and speed and access to customers, you can easily create a road map for the next five years and then you're waiting for engineers to build that thing or or you're having the more frustrating side of the conversation where you say, "Okay, well, we can only build 20% of this road map. Which 20% should we build?" That's not the fun part for me. And so mostly what I do over the last 32 years is I would build five years of a road map and then I would say, "Hey guys, I'm out. Good luck." And I would go build five years of a road map for somebody else that

needed that work. Um, and I, you know, the part where we're gradually seeing that roadmap come to life and doing the horse trading thing where, you know, we get new stakeholders with different opinions like that, that part was just more political and bureaucratic for me and that just wasn't as fun. So, um, you know, when you look at my history, you see, you know, four or five years here and then four or five years there and then a new startup for a little while and then it didn't work and so then a bigger company. And I I sort of just have always been a a three to four years on a project kind of guy because that that's where I get my my motivation from. That's where my inspiration is is

most helpful. Speaking of four, five year road maps, do you think that time frame is still valid today?

Um I I do although I've actually just begun a research project to really dig into that more because I know what you're going to say. It seems like things might be speeding up. Um, and and you're right, I think, but there's there's an actual driver to real change in at least large organizations and maybe also medium ones. And that is that leaders once they're at a certain level of seniority get so close to retirement that they don't need to make dramatic sweeping revolutionary changes. Now, some at companies like Google where we were together, they do that anyway, even though they could just coast for five years and ride it out and let the next person figure out if AI is going to be a big deal or not. But at most companies

like an insurance company in Iowa or a transportation logistics company in North Carolina, if you're 61, you don't care about AI or NFTTS or big data or whatever those things are. You're just trying to ride it out and not break anything. Um there's a generational um uh throttling to major organization changes. It it takes a set of leaders to age out of the market and a new set of leaders that comes in with completely different experiences for real change to happen. And that isn't going to speed up. Now, these new people might be trying to do 28 changes at once instead of one big one, right? They're not just switching from mainframes to PCs anymore, right? They're now they're trying to figure out, you know, how to

work remotely and how to figure out what quantum computing is going to mean and also service the the Africa continent with a whole new market because those people are coming online. like they're doing all those things together at once, but I think those things will come in packages that still have a 4 to 5 year transition span. Does that I don't know if that makes any sense. And that's that

makes sense because if you look at the life cycle of most things technology, there are some few things we can highlight as like major shifts like for example the shift from mainframe to PCs. That was one major shift where was a decentralization and democratization of computers where everyone now has one in their home as opposed to having to go to a library or a university or some lab and then have dedicated access to to things. And then of course the internet was a big one when everyone realized that what they have on their local machine can actually be now available for the entire world to access not just people who physically are in that warehouse or the building or in the office. So I think that was a big change

and I think the whole cloud computing wave was a big one as well where now you no longer needed expensive machines you just needed lightweight machines and all the expensive complicated things was being done by someone else and of course AI is the big one right now where a lot of things you might have assumed as being natural or now considered to be unnecessary because it's being abstracted away and dealt with with AI itself. These are the kind of cases where if you don't react to it, you might find yourself like not even having a business to come back to because you're still in the business of selling mainframes, for example. You might find that at some point that market's no longer there because no one is buying

them. And we've seen so many companies, you know, in that time frame being able to navigate well and others not navigating well. For me growing up, it was always like at least in my college university labs, you had all these like, you know, like purple themed solarist sun micros systemystems machines and they were like the high-end, you know, you had silicon graphics, SGI made these like really high-end machines and those were the ones you really wanted, right? I went back there about a few years ago.

Not a single one of them exists anymore because they've all been replaced by very thin client machines that areorked. all the main software is running somewhere else and you have a Citrix VM that's basically funneling pixels because it's all local to your network. It's fast. You don't really notice the latency differences. There's so many examples where if you were an executive in that company about to, you know, hit retirement age. You might have been like, you know what, I don't see this as a threat. I'm going to keep doing things I've always done. We've been very successful. We're in the cover of all these magazines. We won all these awards for being the most innovative company in the, you know, mid '9s, 80s, and so on.

Why would I ever change? And I think even today if you read like you know follow like Intel for example some of their challenges it's like there's a lot of reasons why it wouldn't be in their best interest to change how they've always done because they became successful doing something really well but then you go that also might be part of what makes them less successful now compared to it. Do you think there's a you touched upon this earlier as well where you have people and your CEOs like doing a many many things then you have like which often causes difficulty in focusing then you have someone like let's say you know like Jeff Bezos you know his goal is like how can I create

the most customercentric company that mission statement is independent of internet no internet mainframe no mainframe AI no it's it's more general it's more broad do you think having a broader vision can protect you in some ways from like having naturally acknowledging there'll be changes, you're going to react to it as opposed to being laser focused on something that you think is going to be definitive without realizing that on the side view mirror, something big is happening that's going to make all that work irrelevant. Yeah. Yeah. I I think

what what I what I like about what Jeff Bezos is trying to do with that vision is that he's trying to create a north star that doesn't have to do with the implementation as much, but it has to do with a thing they can measure for customers that shows them if they're getting better or worse. Right? if you you know you've had hundreds of conversations about OKRs and and you know key metrics and and north stars and and data mapping and all that stuff. But if you can if you can get a single thing that you can measure that says like I'm trying to help customers and if they say I'm helping them then I'm doing the right stuff. And if they say I'm not

helping them enough then I'm not doing the right stuff. And maybe if I'm not helping them enough then it's because I need a cloud transformation. But measuring the fact that you've done a cloud transformation or not done the cloud transformation doesn't tell you about the customer value that you're creating. And so I really like companies that have some sort of customer ma value measurement in their in their north star because ideally I think some people go way too far down the rabbit hole of OKR mapping um and they start to lose track of like what are we really trying to do for customers? You know what and how do we know if we're doing more of that? And most people don't have a way of actually

measuring customer value. Um, and so they have a bunch of proxies and sometimes sometimes they're helpful and sometimes they're distracting.

Do you feel it's easier in some industries than others to be able to do this mapping?

Um, it's I haven't I haven't spent a lot of time thinking about that question, but it feels like it's probably yes. It's got to be different in some than others. Um, you know, if you're whatever, if I'm a doctor, I have a bunch of patients and having those patients be less sick or have them in the in the hospital less frequently or taking less med medication, like those things are all probably improvements, but like helping um helping a you know, formerly from McKenzie, helping a company build better strategies, like how do I measure better strategies? That's hard. Um, and I it's uh it's tricky. So, yes, is it's I'm sure it's different and hard for some people and easier for others, but I think it's an important thing to try.

Yeah. And during all of this, you also made another transition where you are also a public speaker. You go to events. You're you're see by many people to talk about various topics in technology. How did that come about?

Yeah, I um I sort of stumbled into that like everything else in my life. Um uh the in 20 in 2012 I was working at Atlassian, the company that makes Jira for developers in the group. Um and one of our people on our team had applied to speak at a Gartner summit. So, Las Vegas, Nevada, about 800 like IT VPs and CTO's and stuff like that. Guy on my team, his name was Sven. Uh, he had applied, he wrote a talk, he had slides, everything. Um, but then his travel visa got blocked at the last minute and so he couldn't go to Vegas. And so with four or five days notice, he asked our team if anyone would be willing to go and deliver his presentation. I knew his

content because we worked together really closely. I know the market. I'm fairly comfortable on stage, but I, you know, I hadn't really ever spoken to 800 people before. But I did it. I took his slides. It was fun. It was so fun. I like loved seeing like the audience head nodding back to me when they understood something that was hard. Um, and people came up to me after and said that was really great. and they followed me on LinkedIn even though LinkedIn was still pretty new back then. Um, and all that was just a rush. And so, you know, I came back to work and said, "Hey, can I do that more?" And they said, "Um, I mean, a little bit more, but your job is

product management." So, you know, I did it I did it um three or four times a year, and it was always the most fun thing I ever did. Um, and so I, you know, tried to do it a little bit more and a little bit more and, um, and one day I discovered that people actually get paid to do these speeches. Um, I I never knew that. I thought you were just trying to like elevate yourself as a thought leader, maybe sell some of your own services to the audience, sell from the stage, you know, support a product like Firebase at Google um, from the stage. Like all those things are great things to do. I didn't know that people would get money.

And um one day we were planning an event for our uh I was working at a small startup right before Google and we were planning an event and um and we reached out to an event planner and they gave us a list of speakers and told us what their fees were and I was like fees what? I like we reached out to Daniel Conorman and his fee was like 70 grand for an hour. I was like, my brain exploded. I'm like, the most fun thing that I ever do is a job that people have and it pays really well. That it just blew my mind. So, I um you know, I thought about what would it what would that look like as my postc corporate career? Uh and I started

figuring out if I had a speech, you know, if I wrote a book and somebody bought the book 15 years from now, what would I want that book to say? as a technologist, what am I writing a book about NFTTS? And then somebody reads it in 20 20 years from now, they're like, "What the heck was an NFT?" And what were they thinking? No offense to the NFT supporters, but um I was just trying to figure out like when you're picking technology things to write about, which ones have longevity? And that's a hard question. Um so I thought about it and I practiced a little more and I did a little bit more speeches and eventually I tried charging people money and they started paying it. And so almost 18

months ago, uh, September of 2023, I quit my job at Google just to speak. And now I'll probably do 75 of them this year. And, uh, I'm just helping teams do the stuff that I was always trying to do for our team anyway. Just helping them navigate the world, figure out how to solve problems, use things like AI, um, or whatever comes next after that, robots and quantum computing probably.

Are the topics once that you get to choose or are they do they do they get

hints from the the venues itself? Well, so so mostly in order to actually get paid um you need to have some consistency like some people have to know oh I saw Dan and this is his framework for adopting technology in a world of exponential technology and it's great you'll love it. So from a customer's perspective, they need to feel like it's the same talk I've been writing for seven years and it's great and I've rehearsed it hundreds of times, but I also customize a little bit of it to bring some things for your specific industry. So that that's how I do it. I have a talk right now that's an hourong talk and about 20 minutes of that is specific to a customer and or specific

to their industry. and the other 40 minutes are the same every time. I I help people figure out why AI isn't going to take your job and why the robots won't take it either. Um, no matter what your job is. And so that's that's mostly what I'm what I'm talking

about every every time. It it almost sounds like like a a musical live act where you kind of want to see their back catalog of things you really enjoy and why you're seeing them, but they might know some new content. They might customize it for the venue they're at and so on. Yeah. Yeah. Yeah. Yeah.

Exactly. Uh a great analogy. It very much is a performance. Um it takes rehearsal. You know, I have a theater coach that it helps me figure out like where am I staying on stage. When I say everyone, am I doing this with my hands or not, right? And that's there's a right answer to that question. And you know, those kinds of things matter. Uh, and they help your audience, you know, not just drone out while you're talking and, you know, look at their phone or whatever, but they, you know, helps drive real change. There there's a speaker that I saw in like 1996 and I still remember every single thing he said. It changed my life as a technologist, as a business worker. His name is Jeffrey Moore and his book was

called Crossing the Chasm. Uh, the most impactful book I ever read. And you know, maybe 15 years later, I saw Eric Ree and he talked to me about his lean startup book. And again, that changed the way I thought about making stuff. And so, you know, to have that kind of lasting impact, uh, you it takes some work and thought and practice and rehearsal and all that stuff. Both, you

know, Jeffrey Moore and Eric Ree, did they have their books out at the time they made their speeches or was it

before their speech itself? They they did. But to caveat this a little bit with time, back then if you didn't write a book, there wasn't anybody any way for them to know if you're good or not, right? And so once YouTube started to become um a place where people could go to watch what you would deliver, then you know having a having a 10-minute video of you is more helpful than having a book. Although having a book also adds some more credibility um as well, but it's not it used to be that having a book was absolutely a precursor to speaking. Now, if you have video um you can you can get away with it. I don't have a book. I'm writing a book. It's

called The Innovation Machine. It will be out maybe this fall, but um I don't have a book and I'm still getting lots

of speeches. Oh, that's I was about to ask about the role of YouTube and social media in some cases as well because there are thousands of clips I get seen all the time or you know my feed always has like you know snippets of speeches from people about various topics you know is to be successful as a speaker in the future do you have to also balance out your persona in real world situations in in all the events you're going to but also have an online version of it where anybody can kind of top of funnel style be able to know more about you and the snippets of it that then it can be used to entice you to speak in

person. Uh yes, I I think it's it's definitely helpful. Uh as long as it doesn't dilute what you're trying to talk about. Um, right. If imagine imagine like you have a speech Kirupa and you're developing this speech on whatever it is and um and somebody hears that your speech is great and they want to book you for an event and they go to your YouTube channel and then they find a bunch of videos that aren't you do doing that keynote. um which as a follower of you I'm I'm it' be easy for all your awesome content which is great to bury your keynote things right and so they wouldn't see it and they'd be like wait I thought this guy was the keynote speaker maybe I have

the wrong Kirupa um right and and so maybe if you have two different kinds of things that you do I would create two channels two social profiles so that it's very clear um which of M people should go to if they care about speaking and which of them they should go to if they care about you as an influencer. Um because those are just different, right?

I think what I've learned the most from our conversation so far is brand management is actually a big thing because you are the brand in this case. It's not a product you're representing. It's actually you. So anything that you do has a major repercussion on how people perceive the services you provide. Yeah. Yeah. Yeah. Yeah. For

sure. And you know, as you follow me on LinkedIn, you you'll probably see like I I do put content out there. I try to post every Monday, every Wednesday, and every Friday to keep myself active in the feed. Um, however, most of that is not a clip from my talk, right? Because I what I don't want is somebody watching my whole feed looking at every single video and then feeling like I came on stage and didn't bring them anything new. It's like if you go see a comedian and you already know all of those jokes, it's disappointing a little bit. And so, um, I do write lots of stuff. I try to share lots of thoughts on LinkedIn, especially and Instagram a little bit. Uh, but I I

it's mostly just like what I think about the world, why I'm making the decisions I'm making. It's not little snippets of my talk. Um, one minute at a time. So,

walk me through your process for how you go from having an idea for a talk and actually writing it, iterating on it, and ultimately delivering it.

Um for so for for my talk I I um like like a product manager might um I just wrote my first talk quickly without thinking about it and I delivered it for free and then I talked to people in the audience at the reception after the day ended about what they liked and what they didn't like. Right? I said like, you know, what did I say in there that you disagree with? If you could only remember one thing from what I said today, what would it be? And I asked my audience like what my keynote should be.

And then I I threw out the stuff that they didn't think was that useful or that they didn't bring up at all. And I expanded the stuff that they really liked. And then I did it again. And I did, you know, I did that for five years. The whole time I was at Google, I delivered, you know, four, five talks a year where each time I was just figuring out like what do people really like that I talk about and what's the what's the core of my thought leadership? Like what do what do I really think about the world? Um, and you know, it took it took the audience helping me to find that.

Um, because I think a lot of stuff, but also other people also think those things. What's the unique thing that I think about the world? And that's a way harder question. You're almost like AB testing in real life. Yeah. Yeah. For sure. You are AB testing in real life. And every time I try a new story, I just did it to you at the beginning of this conversation. Like when I, you know, when I'm telling that um that architecture meeting Mr. Pac story, you know, I'm trying it in different ways every time and I'm seeing like what feels good. I think I rambled on a little bit too long in this one, right?

So, I'm gonna I'm gonna take a look at how I said that and I'm gonna I'm gonna see could I make that a little tighter? Could I get to the point more quickly?

Um, that kind of stuff. I think the nice thing about podcast is that it does encourage rambling. It's often a desirable thing because you get to just see someone in a more natural state. But I read a lot about how comedians come up with their material. Like the one of the reasons I I'm always curious about like the rise of comedy clubs and what sustains them especially given today where very few clubs are really successful because it's all online but comedy clubs will have a very special place and one of the number one reasons they give is same as what you did where they can actually workshop their material. They can see what works. They bring their notepads out. They literally they're taking notes and recording

things and scratching things out. And that to me I'm like that makes a lot of sense because you can't get that reaction from anything else in the

future. Yeah. Yeah. For sure. for sure. And also make sure as you're doing that that like um when when you're delivering a talk for free because you filled out a call for speakers at the Splunk conference or Salesforce or whatever, then you could do whatever you want. Like they don't care. Um uh but if somebody pays you your your your rate card for some event, like you know, you need to dial back the amount of experimentation you're doing there. So, so you know, my goal is to do one free talk every quarter. So, I'm always like looking at, you know, South by Southwest or um uh CES or uh the Splunkathon or whatever, you know, maybe Google Next one year or something like that. So that I have these places where

I'm delivering some material that I get to try out um and see like what would it if this audience is way more technical than the insurance company in De Moines, Iowa, do they still like my content? because they already know a lot about technology and um you know so those are the kinds of experiments that I'm still doing. I try to do that once a quarter with a live audience for some of this I guess um testing whether this material

is going to resonate and not has AI helped you in any of these ways and the reason I'll give you is that I I give a lot of presentations at work and I do like to actually just like you change things up in how I talk about the same thing every time I present just to see like what makes the audience understand things better and so on. I've recently started playing with just the voice features in these AI assistants and saying I'm going to present topic A.

Tell me what you like and don't like about it. Pretend like you are so and so. And I found that, you know, it's getting better, but compared to what it was 6 months ago to what I'm getting like a week ago, I found the feedback has given me has been very closely matching what I see in re real world and presenting it to individuals. I'm curious to know like if you've tried any

of those kinds of things. I I've definitely been experimenting because I one because one of the things I'm doing is helping organizations figure out how they can use AI to do stuff like this. So I want to make sure I'm I'm attempting it as a as a as a practitioner also so that I have firsthand experience. But secondly, there are some things that AI is good at giving you um and other things that that they're not. I don't I haven't yet done the VO voice version of that. I mean, I use I use voice with chat GPT and Gemini sometimes, but um that's just really to transcribe the question and if I'm at my computer, I I just type it. Um what I do do a lot though is put a a snippet of my

story into Chat PT or Claude. When I'm talking about my thought leadership, I usually use Claude or Gemini because I like their privacy policies better than Chat PTS. Um, but I'll put stuff into Claude and I'll say, "Can you make this a little bit better? Can you make it a little tighter, more crisp? Um, how's the structure? Should you should I start with a with a a James Bond moment to get right into the action and then explain what's going on a little bit later or something different?" And it's it's great at giving me that kind of feedback. That's what I use it for right now. Um I haven't really asked it like what what would you think or what do you think an audience might think? Um I have

enough audiences now that I'm getting the real feedback from the real people. So and they all think different stuff. So it's a little bit a little bit hard to generalize. Um but it's it's worth trying. I should certainly play around with it a little bit more because AI is pretty knowledgeable. Y when writing

your presentation speeches, do you start with like pencil and paper or do you go

straight to like something digital? Uh digital but not a script. Um what I actually do is I make the slides for my talk first and usually low fidelity. It's just like five words on a white slide and then five more words on another white slide and then um uh I write some amount of the deck, maybe 15 slides or so. And then I talk to my camera as if I'm giving the presentation and I record that and I listen to it back and then figure out like what in there went really well.

What did that should be the script and what in there should I try again? And I I I write by by speaking and transcribing as opposed to typing a script and then trying to read it. Is it difficult to hear yourself talk and watch yourself? I I get that a lot. Um it's not for me. Like I I I have like I'll watch myself over and over again. Like I don't know what it is about me. Maybe I'm a narcissist. Um uh but like when I get when I do a practice run for a speech, I'll you know my speech is an hour. I will record myself for an hour and then I'll listen to it for the hour while taking notes. Um sometimes I'll listen

to it a second time. Uh sometimes I'll play it again on audio while I'm on a plane. Um I'm listening to myself a lot of of the week. maybe 10 hours a week I'm listening to tape. You know, if you were playing sports, I'm not a sports guy, so I shouldn't use sports analogies, but if you're playing sports after the game, you watch the you watch the tape with a coach and you try to figure out what could you have done better. And if you didn't do that, you'd be a worse sportist.

Yeah, I'm not a big sports person also, but I do like biographies and reading about it. I think one of the things I read about I think you know Tom Brady and Bill Bilichek that set them apart from others is that they spend hours reviewing footage of themselves playing where the team can do better and also watching other people play you know in recordings and seeing like how they're operating. So I think there is something too you know may not be the most fun thing to do for them but there is something that gives you an edge in just having more data on both what you do and how others deal with similar situations and how they react to things. Yeah.

Yeah. Yeah. Totally agree. So, so in speak in terms of speaking to audiences, what is the most fun audience to speak to?

Wow. Um, I think the the kinds of audiences that I really enjoy are the the the kinds of um uh like middle middle range technology audiences that are not super technical, but they're also not completely non-technical either. Right? somewhere in the middle. Like a a a fun example, one of my most fun events this year was a bunch of people that are salespeople at a cyber security software company. Now, I first signed up for that and I was like, what am I going to tell a cyber security company about AI? Like, I'm sure they got it figured out. And what I actually learned is that I'm not talking to the engineers. I'm not talking to like the senior, you know, security ops people.

I'm talking to the salesperson that just has a deck that somebody else wrote and they're trying to like explain what this highly sophisticated thing does and they're not the developer and the customer doesn't understand it either. And that those are the kind those are the kinds of people that I like I give them a way of explaining something that they are so grateful for. Uh because now they can use that way of explaining that thing to um to their customers too. And they're they're just so grateful and they're um it's such a a a binary switch where they just all of a sudden understand something that that was super confusing and threatening before. And um that's the most fun group for me

when it comes to speaking. You know, we described a lot of things that you're very good at. One of the things that I've always found, you know, working with you in real life specifically is that you have a knack for simplifying very complicated things. And I wonder if that indirectly shows in how you present material because we just mentioned right now where the security the sales team was able to suddenly get it. It might have a lot to do with, you know, not that the material was new to them, but the way you kind of simplify some of these abstract concepts and the things they can relate to. I wonder if that played a big role. Yeah, for for sure.

And and that's in that's in my stage intro, right? It it literally says Dan's superpower is making complex things simple and useful. I was about to exactly ask like what do you think your superpower is? And he just, you know, read it from your actual biography.

Yeah. Yeah. Yeah. Yeah. It's it's um it's because I because I started at a very non- tech company like that first company that I described at the beginning of this call was a was a coupon printing company like they print coupons for the newspaper. Um those people didn't know anything about PCs or the internet or what Java even was. And quickly out of necessity, I became a translator between non- tech people and tech people. And I just had 30 years of practicing that over and over again with like plopping myself in in a new industry with a new piece of software that I just learned three days ago. And I had to try to explain that to my VP of of operations, whatever. like that that

just was a thing that that I just got good at. And maybe it was practice or maybe there's some of that about of that that's inherently um you know in my DNA. I'm not sure. But that's for sure the thing I'm exploiting now as a speaker.

Do you get stage fright?

Um sort of but not really. um before I speak, like 20 minutes before they call my name and I'm in the back of the room and I can see all these people and they're all like rumbling and and I hear the the president of the company speak about all the stuff they're trying to do. my, you know, my stomach's in knots and I'm, you know, uh, uh, nervous for sure, but then as soon as I'm like in my content, as soon as I'm just thinking about the stuff that I've rehearsed hundreds and hundreds of times, I it's it's not that it's not that hard. I I just really am not thinking about it. I'm thinking about the content and just trying to be myself on stage. I'm talking like I talk to

you, right? I'm not really thinking about the fact that I'm in an arena and there's like 4,000 people out there. That's uh that's a little scary sometimes, but um but I'm mostly I don't

think about it. And I think as product managers, you get a lot of presentation, you get practice presenting as well. Might be a large group, but being able to think on your feet, having to suddenly have an hour to come up with material and present to people. you have definitely more time in as a as a public speaker in some of these cases, but I feel like a lot of opportunities you get because you all these surveys still you people ask like what is the thing that terrifies them the most? It's always public speaking that always comes up, you know, to me in some ways I'm like yeah it doesn't bother me. I you know you know I the same nervousness comes up if I like talk in a real life venue and

so on but not too much but then you go back also every as a PM almost every week you're just like constantly doing this and when I think back when I was an intern I give my first presentation to like my larger team my intern project like the night before the day before that I was just like dreading it you know the way people describe it to me is kind of like I never you know I never been skydiving it's on my bucket list of things to do but absolutely terrified of it they're like yeah you're terrified you know getting on the plane or you're terrified like you know you look out and you're about to like jump on and so on but once you jump it's just it's fine

you once you reach terminal velocity you don't really feel I'm like that's not comfortable comforting to me in any way shape or form but I'll take your word for it I think public speaking is the same thing to a lot of people because most people I think don't ever get the opportunity to practice public speaking or speak in any kind of a venue that is larger than like that's people are familiar to them and so going up in front of strangers to talk about something and they don't know you you don't know them and and all of that. I can imagine that actually is a terrifying thing for a lot of people. I can still see where the surveys keep

mentioning that. Yeah. Yeah. It for sure is. Um but like you know now that I've done it a bunch of times I um one thing I I think is that audiences are usually really nice. Like if they don't like you, they're just going to not be engaged. They're not going to yell. They're not going to get heckled, right? They're not going to stand up at the end and grab the microphone and say, "You suck." they're just they're going to be really nice. And so you're right, as a product manager, we're used to pitching things. And about half the time as a product manager, you pitch your thing to the team or the VP or the whoever and they don't like it and they tell you

they don't like it and they send you back to the drawing board and they make you do it all over again. Your audience is never going to do that. Mostly you'll get three people that come up and say, "That was really great. Thank you." And then all the other people, whether they liked it or not, they're just going to fade off into the distance and you never see them again.

Yeah. Do you prefer speaking in venues where you can see the audience or do you prefer speaking in venues where the illumination is only on the stage, so all you basically see are just darkness and occasionally the light from a phone

that just like turns on and off? Yeah, I love being able to see the audience. It's really hard for me when I can't see um the the people. I can't see the head nods. I can't see, you know, every once in a while people take their phone out and take a picture of your slide and then, you know, oh, this is resonating and that's that keeps happening. I must be doing okay. You know, a couple times the light on me has been so bright all I could see was light. Um and I have no idea who's out there. And that um that definitely makes for better video because you got a nice big spotlight on you, but I I I would much rather see the

audience's eyes and their head nods and their phones taking pictures.

You know, I have a few more questions on the same vein. when you're speaking, I've seen speeches where people are often just on stage and then I've seen also situations, you know, this is mostly I've seen in like I think at Salesforce actually a lot of the presentations and speeches there where the speaker is actually walking between the tables and like going around the room in like a zigzaggy like like a Roomba in some ways do you which is your

preference? I think I'm generally not a walking around the room kind of speaker. I think there are contexts where that's helpful. Um, where you're more engaging, where you're getting stuff out of the audience, asking them a bunch of questions, asking them what they feel like. One of my mentors, his name is Seth Madison, and he is a master at that. You know, he he jumps down off the podium or off the off the stage and comes around the audience and like sits down with people and says like, "What do you think? What was what was your favorite thing about today?" and he's just great at that. And as a as a conference closer, like when you're trying to like leave the audience with like a comforted

um recapped, you know, right amount of energy level, when you're trying to do all those things as a closing speaker, coming down into the room and and pulling everyone else, meeting people where they are is really, really helpful. I uh don't do that yet. Maybe someday I will incorporate that into my stuff. But um but uh right now I I don't do that at all. And um maybe maybe I do ask people things. I I pull the audience and get hand raises and stuff like that, but I don't I don't come down into the

room that much. Yeah. Last question that you know in that same train. I know some speakers like to have music playing when they are coming up on stage. And it's often the music that they typically get excited by and and do all of this all this work. And I actually asked this question to you know when I was in college one of my AI professors name is Patrick Winston. He always would play Rolling Stones before he would get up on why do you do this like why do you play Rolling Stones music? And these were like large lectures like 400 500 people there. So it was definitely a large enough thing and then he do this like mult three times a week for however the semester

long it is. It's like, yeah, for me that helps me get into the zone because I do this day in and day out like talking about AI, teaching about AI and so on, but I can't be in that professorial research mode where I'm like completely disengaged. Putting this music on triggers something where I'm now suddenly doing something where I'm like, this is not my norm. I need to now put on a performance and do a good job teaching. And I've seen public speakers often do something similar. So I'm curious to know where you stand on that.

Yeah. Yeah. So, um, generally it will matter if the event people are set up for that or not. Like, how's the audio in the room? Are you in the, you know, are you in a a 150 person room in the basement of a Marriott or are you, you know, in Vegas with, you know, 1,200 people there? That that matters a lot. So, a lot of times I go to an event and the event people will say, "Do you have a preference for walkup music? And I'm still I'm still finding the right song for me. Um for a long time I've used a cover of the Beatles song uh uh uh re Revolution. Yeah. Say you Want a Revolution. That that song. That's my that's my sort of go-to song. There's a

cover of it by uh uh the Mona Lisa twins that I think is cool and a little bit more modern. Uh I like Imagine Dragons or Okay Go. Like those are the kinds of like they get the they get the audience like thumping a little bit before you get up there. It just brings the energy in the room up a little bit and that can be super helpful. But finding a great song that has the right beat that also has the right message is hard. Um and I've struggled a little bit with some of the more modern songs to find what that

song might be for me. What is your dream venue to make a speech in?

Wow. [Music] Um, I don't know. I think my favorite venue last year, uh, was was really amazing. I loved it. It was, um, the Cleveland Public Auditorium, uh, which is just a venue. It used to be like a basketball. Probably the Cavs played there originally. Um, it it, you know, really really a hundred-year-old thing. The stage is all ornate. Like it's it's amazing. There's like two decks. It's just a really really wonderful uh place to be. The stage is cool. The backstage is epic. Um that was really fun. The the mostly by the time they like outfit the room, they all look the same. You know, they're put they're putting the stage there. The wider screens are are great. Like if you get if you get like um cinematic wide

screens um for those are that's super fun to to play in. Um, yeah, as the room gets bigger, I think that's fun. The the room I don't want to be in is the one where there's people all around you and you have to keep turning as you as you speak. That's so awkward and hard. Um, I don't want to do that. But specific venues, I don't know. Um, somewhere in Vegas, those be those are always fun. They're big and they're What do you

think of the sphere in Vegas? Um, I

think that's really cool. I think um I think that would that would be neat to speak in for sure, but I I would it would take I would spend months on figuring out what my graphics were going to be for that presentation. Like it would be a massive massive because they do have the opportunity there to do something very different where it's not just going to be a rectangular screen, but actually take advantage of the full, you know, 360°ness of it. Yeah. Yeah.

That would be amazing. In fact, now that you planted that seed, I'm going to start working on that already so that when it does happen, I have the I have the slides ready because that's going to create some work. Dan, is there anything else that you would like to share with

the world? Uh, no. I think just I really enjoy having conversations with people that care about the stuff that we're talking about right now. So, if you are on LinkedIn or Instagram, find me. I'm pretty easy to find. My name is pretty unique. there's only like 20 of us in the world. So, you'll find me uh and connect with me on LinkedIn or Instagram. I'd love to follow you back, have some conversations in the future, and uh I I wish everyone the best of luck and and I want them to let me know

how I can be helpful. And I'll make sure there links to all of that in the description in the show that you can see as well. Dan, thank you so much. It was great catching up with you and best of

luck. Likewise. Thanks, man. I'll talk to you later. Bye.