TEH 126: Leo’s Origin Story

In This Episode: Leo’s Origin Story: from Geeky to Microsoft to Ask Leo!

This week the TEH Podcast is hosted by Leo Notenboom, the “Chief Question Answerer” at Ask Leo!, and Gary Rosenzweig, the host and producer of MacMost, and mobile game developer at Clever Media.

(You’ll find longer Bios on the Hosts page.)

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Automated Transcript

It’s the TEH podcast episode one hundred and twenty six, I’m Leo Notenboom of Askleo.com, and I’m Gary Rosenzweig of macmost.com.

How is life in Denver, Gary?

Well, it’s unlike the rest of the country, which is all talking about cold and snowstorms. It’s like sixty five and sunny today.

So I hate you. The we’re not talking cold and snowstorm, we’re just talking cold and rain up here. It’s been raining like crazy for the past several days. So when you live in Seattle, is living up to its reputation right now, which is fine. This is this is what all the locals want everybody to realize happens 365 days a year. But but, yeah, things are kind of wet out there. The yard’s kind of muddy. The dogs are, you know, they’re lowriders.

So they pick up a lot of water when they come back in. And so and so.

So we’re going to start we’re going to do something different for this episode. And, yes, a future episode as well.

Maybe next week we are going to delve into our respective origin stories.

I was bitten by a radioactive bitten by a radioactive computer, and that’s how we got to be. It was about where we are today.

No, of course, you know, today we’re going to talk about you and everybody who is in the tech industry has basically an origin story. Oh, I got my first computer or my first interest in computers came because of this or something. And and you and I are no exception to that.

So today, let’s talk about your origin story. As I understand it, you first, like many people of your age, had an interest in electronics for computers. Yep.

Are back in the days of RadioShack actually still existing and Heathkit being a thing? I was I was looking at all sorts of random electronics stuff. I, I wrote up in an article that’s actually on my personal blog I looked at it’s actually a ten year old article that what I was somewhere between like nine and sixteen. My parents had a friend who was, as it turns out, a TV repairman for Sears, actually. And he, among other things, would allow me to play with his oscilloscope and show me some random things.

And back in those days, there were ways you had to make adjustments to your color TV so that the three guns would all line up properly on the screen. He showed me how to do that. So I went home and adjusted our TV for a better picture, you know, those kinds of things. And I was also I mean, clearly, I was one of those those silly kids that took everything apart and was unable to put most of it back together again.

If we fast forward a one one little story that I don’t know that I’ve actually written about this anywhere at all back in I think it was seventh grade, so I probably would have been right in that same age range.

I our class was discussing or learning about the different no bases, you know, like base ten base to base, whatever. Right. It’s an arbitrary thing. Base sixteen. And what we had was instead of a spelling bee, we had we call a base race and each person was simply had to read out or think out the next number in sequence in binary. So we’d start to one person would say one on person would say one zero. The next person would say one one and so forth.

I did not win, I came in second, but it was I took that, especially looking back as kind of a precursor of things to come, because at that point, I didn’t know computers were just not a thing. They were just not something we played with, not something we had, not something we talked about at best. The only thing that got me excited at that point was and we’ve talked about this before, the movie Colossus of Forbin project, where they basically have two supercomputers in the United States and Russia or Soviet Union of the time linking up and basically taking over the world that wasn’t there yet anyway.

So, you know, with that is kind of a background. I was playing with electronics. I knew how to use a soldering iron and, you know, just sort of stuff. Eventually I did, of course, graduate high school in my class of seventy five.

And one of the things that you end up doing at that point, of course, is applying to different colleges. I applied to the four different universities here in the state of Washington, the four major ones. I ended up going to the University of Washington and they in their application basically said, OK, you know, what is your interest? What’s your field of study? What what do you you know, ultimately it’s the question, what do you want to major in which, of course, I wasn’t in any way, shape or form prepared to answer.

So I just put down electronics as being something interesting. Now, this wouldn’t fly today, but what they ended up doing at that time was simply assigning me to the College of Engineering and further enrolling me in their electrical engineers program today. That’s like a separate process that you then have to meet more criteria that I’m sure I never would have met back in the day. But it was just sort of fortuitous happenstance that my use of the word electronics on my application put me in the College of Electrical Engineering at the University of Washington.

I think it was my and again, I still I haven’t touched a computer yet at all.

So, I mean, like at that point I’d be, what, about 18 or 19 and the second quarter of my first year, second semester, I should say, there was this class that was a requirement for all of the engineering students.

It was engineering one forty one introduction to Fortran programming. Fortran, as our listener may or may not know, is fundamentally an engineering programming language.

It has its roots there and was used very, very heavily in the engineering disciplines that especially around that time for doing all sorts of analyses and modeling and so on. So of course it was required for everybody. You just you had to take Fortran programming and I did. And I don’t know if it was like a week or two in or three or four, but it was like that right. There was my light bulb moment.

That was the point at which I realized, oh, crap, I’m good at this, I enjoy it, and people will pay me to do it for them. And ultimately, within a span of a few weeks, my career had been decided, my direction had been decided. It was you know, you often hear about people stumbling into their passion and that’s absolutely what happened to me. Now, Fortran them is not like programming now. I mean, this was still back in the days of I was learning to program Fortran using a mainframe.

What do you remember? What type of mainframe was a CDC? Sixty four hundred. OK, and and then they got a second one. It was the CDC cyber seventy five I think it was they were sixty bit machines. They did not use they octal. So I left that class thinking in octal rather than thinking and hacks. Hacks would be much more useful later on.

But you know, basically you wrote things on punch cards, you learned how to use a keypunch you you put your your your head, your deck of cards with all the statements in the right order. And you hoped that they didn’t get dropped because then all of a sudden you’d have to figure out how to resort your cards once again. Anyway, I had a great time.

I literally I just I had such a great time in that class. Of course, you know, I got a 4.0, the highest score there. And as it turns out, maybe it was the seeds of Askleo.com beginning, but I was helping other people in the class. Right. They were they were having problems. They would you know, obviously as a class, we would hang out together and talk about things and and I’d say, oh, yeah, well, that let me take a look.

And that over there needs fixing or, you know, that’s not how this works. So let me explain this concept to you. So that even started fairly early. My second class, actually, I took over the summer.

Normally folks were taking summer. Off, but I, I, I was having fun, so I decided to take my second class, it was also on the mainframe, of course, but it was of all things can even make a guess.

LOL, no, no, actually, I did learn Goalball until much, much later, so it wasn’t so it was another computer language. Was it was just see.

No I don’t think I even stumbled into see until I left the university. No, I learned the CDC.

Sixty four hundred assembly language. Awesome.

I went straight to assembly after Fortran and again I just, I had a blast with it. It was fun. I mean, imagine doing assembly coding on punch cards.

I wrote random tools that would print pretty pictures and do banners and so forth on the line printer at that time. But these were all things that I just ate up.

And it’s funny, the prof, the guy who was teaching it at the time, he said, you know, there’s here’s this sequence of instructions and there’s some magic sequence that let you, I think, do an absolute value as his test. And I can never remember what it is. But there’s always somebody in the class that reminds me and sure enough, you know, come up to him later and say, yeah, you do this.

So like I said, it was just one of those things where things just clicked. So I went on in the electrical engineering program. And of course, there’s various classes that you have to take, some of which were required, some of which were more electives that that basically went in line with, with what I had realized was my passion for computing and computer technology.

So I did really bad in statistical analysis and those kinds of things, even though you were supposed to use the computers to do your analyses.

But the whole concept of the math behind it all just just went way over my head. But when it came down to like working with microprocessors because I had my first introduction to microprocessors there, the eighty eighty, we were tasked with creating basically projects.

You had some kind of a serious project to do over the course of one semester. The first one I did was a cash register. I basically just wrote a cash register. I called it the cash register application program because I thought the acronym was cool. And side effect was that I had just come off of working at a grocery store for four years. So I also had a practical application for what this might actually be used for. So when you want to do the other project that was again, a semester long project was using, I think it was at TI ninety nine hundred microprocessor sixteen bit.

That would be my first sixteen bit processor to control and transept.

Which was kind of fun, I got the train running and, you know, you’re supposed to switch it, it’s a couple of concentric circles with switches between the two. The goal was to get three trains running simultaneously on the two loops.

So you actually had to somehow control where they were and handle essentially what I didn’t realize until later, early multiprocessing being able to handle three independent things happening at the same time. I did well with that, had fun with it. Again, it spoke to me because I already had like a big old train set at home that was used to playing with.

But what was again, I think telling was that before I graduated, I ended up being an assistant for the Fortran class for one quarter, a teacher, even though teachers were only supposed to be graduate students. And I ended up writing what we would now call device driver software for the next iteration of that train set for the students to use so that they didn’t have to worry about the low level stuff and that they could focus on the algorithms that they were working on to get the trains running.

So, I mean, again, you could tell that was just that was a lot of fun. I had I had a blast doing that kind of stuff in in school. And I definitely what I wrote up my first resume, I took care to separate out. OK, yeah.

Yeah, OK, here’s my GPA.

But if you take a look at the courses that actually matter, my GPA is much higher. Right.

You know, I sucked at philosophy and my chemistry teacher was horrible in physics, just didn’t do it for me.

But if you focus on the things that were all about computers and technology, I had it nailed. So I ended up getting my first job interview was actually someone that my one of my advisors at school pointed me to.

I bombed it horribly because they wanted me to do hexadecimal math and I had no experience with hexadecimal. Like I said, everything we were doing was in octal. So it was a horrible experience. But I ended up working at a small company in Seattle, was my first job out of school. I did not go directly to Microsoft. First job out of school was, first of all, company in Seattle. They started out with, well, what I joined there were twenty five people.

I was the third person in their software department.

And I went from twenty five people to five people by the time I left, wasn’t my fault, honest, I was the software department when I left, so I basically outlasted both the guy that hired me and the other person he hired. At the same time. I have I got a lot of fun doing. This was a Zaydi processor based organization. They were doing data entry terminals, basically a keyboard and a tape drive and a little display. And the whole idea was that data entry operators would basically be entering data all day long that would get recorded on the tape drive.

And then at the end of the day or overnight, they would set the machine up so that it would then transmit that data to a data center where it would end up getting processed. My responsibilities were things like the communication software that basically sent that data on. So I was, you know, basically working with the protocols between this little Zaydi processor and a mainframe at some other some other place, managed to get a trip to London out of it to go visit one of those data centers because they were using our machines.

It was fun, but I ended up touching on a whole lot of other stuff while I was there. I definitely ended up walking into that whole jack of all trades thing that that ultimately has served me very, very well over my career.

Because in addition then to the communication software I was also responsible for, they had a cassette basically that they used on the machine. They had documentation that needed to get sent. They I ended up doing a newsletter of all things for the company that talked about the technology and going out to all the customers that all sorts of random things.

Then, of course, they decided they needed a machine that ran with disks and CPM at the time. So they built a new machine on the same processor. And I ended up doing the device drivers, what we would now call device drivers for KPM and implementing all that and getting actually a pretty, pretty nice setup for KPM It’s an eight bit operating system.

There wasn’t a whole lot you could do with it compared to today’s machine. But boy, we really did exercise the heck out of it. A Zaydi processor can really only access sixty four K of memory, but we had some fancy hardware that allowed us to expand that up to two hundred and fifty six k it was you know, there’s some really interesting innovative stuff that we were doing there.

The the basic has an interesting story because of course at that time this would be around nineteen they’ll say seventy seven. Seventy eight.

Microsoft was the name to that basically did basic, they had already made their name Bill and Paul had already done their thing with the Altair and it was Microsoft basic was sort of the pseudo industry standard at that small microprocessor level. As it turns out our company had Microsoft had I’m sorry, we had a cassette basically. And what I didn’t realize until I got there, until I started looking at it is in fact, it was a copy of Microsoft. Basically, what I heard later is that it wasn’t necessarily a legal copy of Microsoft music.

One of my predecessors, someone who had left the company shortly before I joined, actually had reverse engineered it, the assembled it. I’m just not sure exactly what technique he used. I think he actually managed to get source code and he had made Microsoft basic work on our machine. I was promised that the legalities had all been taken care of before I arrived.

So yes, I was working on Microsoft Basic before I even joined Microsoft. What was ultimately ironic is that the guy my predecessor, who had illegally, so to speak, implemented Microsoft basically on our company’s hardware, went on to join Microsoft a few months before I did.

And in fact, I ran into him a couple of times after I was working there.

He was not a happy camper. I’m not sure what his story was, but he had done that.


So Microsoft, I joined in nineteen eighty three again. I’ve got another one of these. You know, there’s a story behind it, of course.

I wrote it up in an article on my personal blog again, that it was one of those situations where, you know, I could see the company was going from twenty five to five people. I’d already encountered Microsoft enough times I realized that they were local. It was a situation where, you know, I should just it’s probably time to prepare some options here in case the company goes from five even lower. The writing’s on the wall. So the conversation I had with a few people was, OK, I’ll send them a resume.

What’s the worst that could happen? They could get back to me. Well, they got back to me. OK, fine. I’ll I’ll I’ll send them the additional information. What’s the worst that could happen. They could ask me for more. They could ask me in for an interview. Well they asked me in for an interview so I said fine, what’s the worst that could happen. I’ll go and interview and have some fun with them. And what’s the worst that can happen?

Right. Well, long story short, of course, is they ended up making me an offer. I ended up sitting across the table. From Steve Ballmer, and he offered me less than I was making in my current job and these things called stock options, which I had no idea what they were or what they were would eventually be worth.

To me, it was just funny money. So I didn’t really think about it that much. I said, you know what, that’s not even as much as I’m making now. At least offer me something more on an annual basis so that I can, you know, justify it. And he did. And I did. And of course, the rest, as they say, is history.

How many people were at Microsoft around that time? Three hundred and sixty, I think, for.

Wow, I remember correctly. Yeah, yeah. It’s funny.

It was just at that cusp where. No, know, not everybody knows Bill. In fact, I was having a discussion with someone just the other day where, for example, because I was joined Microsoft in 1983, everybody kind of assumes that, you know, Bill and I are buddies. Well, the short answer is no.

I’ve actually seen how does this work? I have emailed him twice. I’ve gotten a response once and I’ve been to his house five times. And it’s the house because he uses them for like a new hire events. Or at one point there was an old timers event and we were out at his new house, which is huge of, you know, as you might expect right at that time, he was absolutely the wealthiest man in the world. So, yeah, it was it was a small company, but getting bigger for I think the first 10 years I was there maybe a little bit longer.

The company basically just doubled in size every year. So it was three hundred and sixty when I started. It was seven hundred and twenty. But, you know, the next year it was fourteen hundred after that. And, you know, it was literally an exponential progression in size. We were always building buildings. We were always trying to project, we were always hiring new people. But one of the neat things was that offices were based on seniority.

And after a couple of those doublings, I was the most senior person on, you know, like for the last, I’ll say, three quarters of my career there. It was pretty often that I was the senior person on the team, even more so than whoever I was reporting to. And when it came time to move to yet another office, I got to pick and I’ll take the one over there with the window or the corner window or whatever.

So that was always, always kind of fun. Anyway, that’s where I learned COBOL.

I didn’t learn COBOL until I actually joined Microsoft because they when I started they said, OK, we’ve got three positions that are available. There’s one and basic, there’s one in basic and there’s one in COBOL. And of course I said great basic. I have experience. Let me take that one. And they said, well, no, how about this other one? I said, OK, great, give me that other basic I don’t know. How about this COBOL thing over here.

OK, fine. I’ll go work on COBOL and of course to work on something you don’t necessary to work on a programming language, you don’t necessarily have to know the programming language.

In other words, clearly it wasn’t a requirement requirement that I know COBOL in order to be able to work on COBOL, certainly for the tasks that I was initially assigned, that just wasn’t part of the part of the requirement. But of course I did.

I learned COBOL and in fact wrote one of Microsoft’s first internal bug tracking tools using COBOL just as an experiment to see how it would work. And it worked out really, really well.

But I spent I think I was about two years on COBOL. I moved on to I did finally end up joining the basic group at that time. Management training was here. You’ve got some reports. Good luck. There was no training. It’s funny. The I often hear from people who are joining the company these days and they say that a new hire orientation is like a full day exercise where they’re, you know, pummeling you with documents that you have to sign and giving you all this information.

No mind you are. My new employee orientation was a half an hour sitting in the manager’s office, filling out a couple of forms and being shown to my office. And that was the same thing for management training. There just wasn’t any. It’s like, here’s the deep end. Hope you can swim. And of course, I learned how to swim. I ended up managing individuals or writing software, going back and forth for my entire career at Microsoft.

One of the things I really appreciated about the company, even though it was, you know, on the order of fifty thousand people when I left, many aspects of it still had that small company feel. I’ve often described it to others as working as as a number of small companies that just happen to share a campus. And it was a really, really good feel for many, many of those years. A lot of fun doing that. Still that small company kind of thing, making decisions, pivoting quickly in ways that large companies really can’t do.

Oh, let’s see. So like I said, I had a course through, you know, programming languages I worked on. I went on to work on. Microsoft money for a while, I worked on Windows help for a while, I worked on the character Mode Help Engine for a while.

That’s where I got my first patent, which was kind of fun. I lost a lot of respect for the patent process in the process. I was just it was too easy.

It was too easy to me. One of the criteria for getting a patent is that it be how do they put it? It should not be obvious to someone practiced in the art.

In other words, whatever sphere you’re working in, somebody else who’s familiar with that sphere should not consider what you’re doing as being obvious. Now, of course, I considered what I was doing obvious, but then I was knee deep in it.

I was neck deep in it. And Microsoft at that point especially, was was working on building their patent portfolio. So, yeah, I got a patent fact. I’ll dig up a link to it because it’s available online. You can still see my name on it. It’s long since expired, of course, the seventeen years long gone. It was about compression tech.

Basically the reason that I lost the respect is that, you know, to me it was if you develop a new type of compression, that’s awesome.

I mean, you you’ve come up with some incredibly difficult mathematical algorithms that, you know, are one percent better than anything else on the planet. That’s patent worthy. That’s not what I did. What I did was I said, OK, I’ll take this type of compression and then do this type of compression and then do that type of compression.

In other words, I’ll just run these three already known well-known compression algorithms in sequence. And it applies really, really well for the application that I’m working on. And somebody said, well, yeah, we should patent that. And it’s the combination of the three. That’s the patent. It’s not any one of those three. Those are individual technologies. But the fact that I strung them together the way I did was apparently patent worthy.

Huh. So fun times. Let’s see.

So let’s see what else I mentioned. Money.

I mentioned Windows help and text help. And I was the ended up working in Visual Studio for a while, the development platform.

I ran the build lab where we got to actually build this humongous project, you know, every night for the developers, because at that time these were these are huge projects. But we shifted.

I’d like us KD, we didn’t fit on floppies anymore.

So, you know, that all happened eventually. You know, things were comfortable enough that I was working part time. And then when that part time opportunity went away, the cat was a kind of one of those administrative cool things where, you know, you could work part time, but that the group that you’re in has to spend a full time headcount on it.

So rather than have somebody part time, they didn’t want to do the part time thing anymore and they wanted to get someone full time. And I said, OK, you know what? I would like some more time for myself, and that’s when I decided to leave, so that was 2001. It was an awesome career there.

I really, really look back on it fondly. Of course, there were horrific moments. I definitely have Dilbert’s pointy haired boss. There is an individual who I refer to as the Dilbert’s be incarnate.

So there were certainly the rough times, but there was some awesome times. And I really enjoyed there for someone doing and loving what I love to do, it was the right place to be for the time that I was there.

So what happened after Microsoft is that I ended up taking a poly. Oh, gosh, I did go back for a few months as a contractor working on a project. But about that time, my parents got ill. So I ended up taking about a year and a half off, was very grateful to be able to do that, but basically take a year and a half off to just sort of deal with all that in. I want to say, well, moments after I left Microsoft, I got invited to join this mastermind group.

You might be familiar with a Gary High maybe. Yes. And, you know, because now I was effectively working for myself, even though I like I said, I was taking about a year to to deal with some personal issues.

And that led to ultimately the day you and I met for the first time.

I think you you went to Vegas, didn’t you, at first?

No. No, I didn’t. But it was somewhere around there.

I mean, we both went about the same time. I mean, it’s fair to say, though, that I mean, the term mastermind hadn’t yet been in use. So we thought it was lively group.

Yeah, it was it was odd group. That was hard to explain, but it was. Yeah, yeah.

The term mastermind certainly been around for a long time, but yes, we weren’t really referring to it as a mastermind group that I mean do you do hear the term a lot more now. So you must have been like the conference after that.

Or maybe I mean, we definitely met online at Leo. Yeah, we met early in an email. Yeah. So we already converse, already knew, knew you through that. But boy, I don’t know when the first time we would met person it would have been around there.

Yeah. Yeah. I think the next Congress was in a year or so.

I don’t know if you were, if you went to that was probably that was I was definitely at that one.

Yeah. At any rate. So at the even at that point I didn’t really have a clear idea of what I was going to be doing next. I just knew that I was going to be doing it solo. As an entrepreneur, I’ve been helping my wife’s doll shop out. So I already had a lot of Internet on my under my belt. I forgot to mention that I spent a year and a half working on Expedia before it spun off from Microsoft.

I was the guy in the data center when they actually released the product on day one.

So I had you know, I had some Internet experience and I had a motivation to to, you know, be my own boss and just sort of do things at home and have fun with it. And I got hooked up with this Internet entrepreneurs group, this mastermind group.

And from that group, there are there’s a confluence of about three or four people that all started and ask kind of site at roughly the same time.

And we were actually modeling someone else who joined the group with an ask kind of site.

And it was like, oh, I get asked questions all the time.

I could publish those. Oh, there’s advertising.

You mean I can make money doing this? People will pay me to do the stuff I love. That sounded kind of familiar.

So that’s ultimately where Askleo.com started. The conference was in May, late April and May of 2003. Askleo.com first answer got published on August the tenth and it had to deal with Internet Explorer Version six. That article is still out on the website just because nobody uses Internet Explorer six anymore. But it’s kind of fun to have it there for for retrospective.

And technically, when I left Microsoft and certainly when I left the contracting position that I was in for a little while, I considered myself as having retired. I was at that point, I would have been like forty five, forty four or forty five.

And I pretty much expected that I would do this thing, this Internet thing for a while and have some fun with it. But it wasn’t necessarily going to be a job.

It’s still not a job, but it certainly takes the time because I’m still having that much fun with it. It’s been, gosh, this year will be the 18th year that Askleo.com been in existence. And, you know, a lot of technologies changed. As you can imagine. When I left Microsoft, I was extremely well versed in Microsoft technologies and not much else. It didn’t take me long to discover things like Linux. My servers were on Linux.

Then almost immediately I ended up, as you know, I ended up purchasing a Mac not long after you showed a couple of interesting features in the final cut pro that I thought were worth getting. Yeah. So, yeah, it’s been an interesting ride since then. This is this is if this is retirement, I’m swear I’m busier now than I was at Microsoft at times, but I’m having just as as much fun today as I was back then. And the commute is a lot easier.

And that’s something that I’m sure a lot of people have figured out in the last year, that this whole commuting thing, now that it’s it’s a bunch of time out of your day, I’m not sure I want to go back to work in person. But that’s the kind of stuff that, you know, people like you and me have been doing for years.

So, yeah, that’s that’s kind of sort of the origin story, there’s all sorts of, as you might imagine, random details and things going on. I’ll see if I can’t, like I said, dig up a link to that patent. And I’ve got links to those couple of articles that I talked about where I’ve already discussed some of that. The the one article that I think people might find most interesting is the one called How It Began and Ended, because it includes but the the ad I responded to from the newspaper, which I discovered not that long ago, the my resume in nineteen seventy in nineteen eighty two and a bunch of letters from people like Steve Ballmer.

And what was then, what did they call it. Old Mail Gram from Bill Gates welcoming me to the company. You know, those kinds of things. So yeah, it’s all very interesting historical curiosities at this point.

When when do you think you got your first email address that would have been made?

The third of of nineteen eighty three. I was Leo n and that was before Microsoft was doing a lot of stuff on the Internet directly. But it was my first email ever. Right. I hadn’t even used email since then and I was introduced to it on at that point it was Zenimax Mail. So it was a Unix variant. Yeah. But that Leo n and again in hindsight, had I known, I would have just said, hey, could you please give me Leo?

Because you know my my name is Leo. I don’t typically go by Leon, but of course everybody seeing that as my email address would call me, that I learned to live with it. And it wasn’t until a couple of years later that they finally got themselves more completely hooked up to the Internet with their own domain. That Leon, at Microsoft Dotcom came into existence.

Interesting. Do you remember would have been when you were at Microsoft, obviously, like when you first became aware of the Web.

I mean, because the Internet was a rally and it started technically 1969 and ARPANET and all of that.

But but when the worldwide web first hit, which was a little bit before, was kind of public, said Microsoft, you might have had access to to it to the early stages.

We had a lot of of of access to stuff for sure. I don’t know that I’d necessarily call it the Web at this point. I mean, we were definitely doing things with.

Well, for example, do you remember tell no. Oh, Syntel was a shareware repository out somewhere. I’m not even sure where anymore. And but there was no web. So how do you get at it? Well, you send a specially formatted email to a specific email address and it would return you a listing of everything that they have. And then you’d send a different specially formatted email and it would return whatever you asked for as an attachment. So that’s how a lot of shareware in that kind of stuff was getting distributed.

We were, of course, you know, doing things like running the old Internet utilities, Gopher and Archie and those kinds of things, which I never had a call to use. The closest I ever got was doing something like like I said, you know, fetching software remotely or getting documentation remotely using the email responder’s, the Internet itself, the true web.

I don’t think I personally really got exposed to it very hard until I joined the Expedia group, actually, when we were ramping up Expedia. That’s when I really got a taste for what it meant to to have an application on the Internet, to write software that people around the world were going to access in real time and and just sort of play with it. Yeah, it’s you know, of course, you know, I caught onto email pretty quick, but again, I don’t necessarily think of that as much as the excuse me as much of the of the Web, as much as I do just you know, that’s the Internet that’s been around forever.

Yeah, how so is your original domain, your original domain? A little different than the one you have now? There’s a date. There was a Daschner original domain.

When did you what did you grab that?

Oh, years after I should have. So, yes, right now I am Askleo.com and that was expensive, but it was going to be expensive no matter what.

When I started Askleo.com, I originally ran it off of a domain that I had already purchased myself called Puget Sound Software Dotcom. That’s the my corporate name.

Even some consulting that I had done prior to joining Microsoft.

I had business cards with Puget Sound software on them, and I had a business license so that I could actually get paid for some stuff. When it goes to Microsoft, I realized I was potentially going to be doing the same thing again. I was able to get the same name, company name and registered the domain and so forth.

So I was actually askleo.com Puget Sound software dotcom and I think that may have been a server in my closet here running. I think Microsoft is.

But the when I finally saw the light probably shined on by some of those entrepreneurial friends, I realized that I really needed my own top level domain. But Askleo.com was taken and it was frustrating because it was taken by somebody that wasn’t using it. Right.

He was just parked on it. So, of course, you ask, how much do you want for it? And he said, ten grand. And I said, hell no.

That was a hard, fast. And that’s an answer that I probably would have changed now in retrospect, along with a couple of others.

But given that it was taken, I just said, OK, let’s do ask Dasch Leo dotcom, which I still have today, and it’s actually got an old copy of some old old stuff on my site. So I ran with that for a long time.

I ended up also getting askleo.com info with and without the dash. And I think there was one other one. Ask Leo with and without the dash dot net, mostly because at one point I started doing podcasts and I wanted to be able to have something that was easier to roll off the tongue, easier for people to type in and less likely to be mistyped.

So, you know, I have I still have, like, all of those silly type of domains or other other top level domain domains.

Some years ago, I want to say, four or five years ago, I reached out to the person who is on the same person. He’d been sitting on it for a good ten years.

And I said, OK, what do you want for it? He said, Ten grand. And I said, no.

So a mutual friend of ours offered to step in and act as a third party just in case the guy realized that I now had it was clear I had a vested interest in that domain.

I, I now had a footprint on the Internet. If he just Googled, ask Leo, he would find me a no. OK, that domain might even be worth more. Right.

But the third party went in there and basically purchased the domain on my behalf and I reimbursed him the the ten grand that I ended up paying for it. Like I said, I probably should have paid originally, but but that’s where we are today is finally on askleo.com the way it should have been from the beginning.

Yeah, indeed.

The other change the other thing I’ve mentioned this in a couple of different venues. The other thing I would have done differently with Askleo.com specifically is I would have started my newsletter earlier. I don’t know if you remember, but in those early days I said, I’m not a publisher, I’m not a newsletter. I don’t want to be a newsletter. No, no, I don’t want to do that. So it took me a good two or three years to to actually, again, see the light as gently imparted on me by the other members of our of our group.

And that’s when I started doing the newsletter. And I like I said, I should have done that from day one as well, because I really do now see the value in having that. And in fact, now that I’ve got that one going, the Askleo.com confident computing newsletter every week unobstructed, I’m up to like I think it’s episode or issue number eight hundred and ninety six.

Now I’ve got, you know, a couple of other askleo.com newsletters. I’ve got a couple of other non tech newsletters, heroic stories. Not all, not all news is bad. My news, seven takeaways. Those are all newsletter based because. Oh yeah. Newsletters. They’re a great thing. They’re a great way to do things even for managing your own time. The whole seven takeaways thing is there simply to force me to have a deadline every week so that I actually, you know, do something that I want to do.

So, yeah, newsletter’s.

I would have done them earlier to get newsletters are not only, you know, do we both have newsletters that are, you know, continue to be valuable, unlike other things on the Internet, which kind of go up and down, you know, how valuable is your Facebook following? How valuable is now? Our newsletters never seem like the gold standard almost right.

They never seem to like lose their value, plus the whole idea of newsletters. I was just telling somebody just this morning who emailed me for some advice, you know, stranger that just asked me some things about how I’m bored. Oh, you’ve got to get a newsletter. And I’m like, oh, boy, here it is in twenty, twenty one. And I’ll be repeating the same talking points about why you should get a newsletter that I would have used back in two thousand.

It’s interesting because for a while newsletters worked really on people’s radar. So I mean you and I and many of our friends kept doing them. I mean, there’s a reason I’m up at eight hundred and forty six, but they weren’t really all that sexy. And what I’ve noticed is over the past, I’ll say two years, they’re bringing sexy back there.

When you take a look at a lot of Internet marketers and a lot of Internet publishers, they’re all saying, you know what, all this social media stuff that we have no control over, I control my newsletter. People want my newsletter. That’s a relationship I can that I value and they value and that’s something worth investing in. So, yes, email newsletters are definitely, you know, email is not dead, which is an inside joke for our group.

But email newsletters more than anything else are just as popular as they ever were, if not more so.

Indeed, indeed. And definitely for both of us kind of secrets of our success. I mean, I don’t know if it’s number one, but it might be number one on both of our lists.

Yeah, I think it would be number one for me is the biggest secret of my success newsletter so far. Yeah.

So, yeah, that’s that’s the honestly that’s the short version. I mean I’ve been talking for what about forty five minutes. That’s the short version of origin story. It’s been, it’s been, it’s been a fun, fun stuff.


You definitely, you’ve got some good years of experience working end kind of the ultimate corporate, you know, computer environment. Microsoft know one of the top companies and all those years of experience you always have, but then switching over to entrepreneur on your own and creating that whole journey.


Yep. Yep. So next week or the week thereafter, your turn. Exactly.

I think we’ll have to find out what your origin, my origin story that what radioactive computer bit me. Exactly. Exactly.

Oh, by the way, that’s the one thing I forgot to add to my list or mention the first computer I ever owned or the first computer I ever used, of course, was this KTK. Sixty four hundred punch cards.

Rohlfing First computer I ever owned an Apple Apple two e. Hmm. And I had fun with that.

I was doing what, a sixty five 02 assembly language and playing. I think they had a version of Star Trek that you would load from cassette tape and all that kind of stuff. That’s one of those things. And this is one where K would be very, you know, we would be waggling his finger at me because of course my machine’s long gone. And now I wish I’d kept it because it’s a collector’s item now.

Well, my my first computer was not an Apple product as a teaser for next week. Here you go.

It was kind of interesting anyway.

Well, cool. Well, let’s wrap up with some, ain’t it. Cool stuff and. Yeah. Self promotion and all that.

What if what if what have you seen. So I just want real quick, we a couple of episodes ago and I didn’t take the time to look up which one it was. You and I talked about the x y problem.

Yes. And I actually ended up using our episode as a reference to go back and find the link to Wikipedia or whatever it was we were talking about to make sure, because as you might imagine, I am a member of a of a of a group of so-called Microsoft old timers on Facebook. And all of a sudden people were talking about getting asked X, but where why was the answer?

They really wanted kind of a thing. I just thought it was a hilarious callback to one of the episodes that we had where this is such a common problem in the in the computing industry, in the computer support industry especially. And you saw a lot of people at Microsoft still or people who are supporting their families who are just regularly coming up with the up. They’re asking me X, but what they really need is Y.

Yeah. And actually, I, I still am working on my process that I talked about in that episode of trying to get people to to give me a good question so I can answer it for them. And even even this week I made some adjustments. Even today I had to send a question back to somebody who did not give me the real reason why, which prevented me from actually coming up with a solution. I said, you really got to tell me why.

And then there’s probably an answer. I just can’t guess at why you want to do this. So I can’t give you an answer.

If you and I were supposed to be prescient, we’re supposed to was supposed to be able to read people’s minds through these wires. Yes. Yeah. The other thing I wanted to mention in terms of just, you know, cool technology, I have been playing with otterbourg A.I. Now it is essentially. A voice to text service, but it’s its primary use case is if you and I were having a face to face meeting, we one of us will take out our phone, turn on order to set it on the table between us.

And it would in real time transcribe what you and I are saying and apparently also distinguish enough of the voice to be able to attribute it, attribute the text to the right person speaking. I have been incredibly impressed by its ability to just listen to what I’m saying and transcribe it correctly, even, for example, while I’m driving my use case. So I’m still trying to come up with a perfect solution for this is I want something ideally on my phone that I don’t have to look at that will allow me to get randomly at any time, take a voice memo.

And this one has come the closest so far. And so I’m just having been having fun with it.

There is a free version for Otter’s Ehi. It allows you to do something like 600 minutes of this kind of transcription every month. It resets every month. And of course there’s features for the paid version. And if it turns out to be really useful, if it works into my use case, then I may end up spending the money. But for now, the free version is actually pretty cool. Having fun with it.

Check it out. Mine’s a on tech thing. For the last several months, I haven’t mentioned a book really on our ancient call section because I’ve been reading a massive three volume biography that’s just taken me months to get through on Theodore Roosevelt.

So I will link to the first of the three books.

I found the first book to be amazing, which is his life up to the point where he was elected vice president in nineteen hundred. And then the second book to be very boring, mostly in the middle because he becomes president.

No spoilers there. He should know that the Roosevelt was president of the United States. And then it gets really boring, which actually is kind of a neat thing to like, you know, fascinating, amazing life of a man that and that he gets to be president. And then it’s like dealing with like labor disputes and legislation and stuff, and it’s really boring. And then the second book is basically his life as as president and then the third is after president, which then gets fascinating again, because he starts actually doing so many things after he’s president because it was a very young president.

So then he goes on an African safari and he’s now going to the Amazon. And he tried running, creating his own political party and running for president again, all sorts of adventures post presidency.

Anyway, I had no idea. I always liked him because of his accomplishments. And he’s a well regarded president. I had no idea. He basically seems to me that you could somehow measure it from afar, that he was probably a genius. I mean, so well, it seemed that he devoured more books than anybody I’ve ever heard of. It just devoured libraries full of books, in different languages, spoken, read many languages, was a philosopher, wrote a ton of books.

I mean, I can’t even imagine with today how today’s politicians are somebody like this who wrote books on, like natural history, like while he was president. Right. Right.

You know, I mean, so he was like and half like a kind of a scientist, really, and explore and wrote these books and also wrote biographies of other people that had come before him.

So it’s just I just had no idea he was so brilliant and obviously an extremely deep thinker and made me kind of sad that, you know, we no longer have, you know, politicians that kind of, you know, go up to the Theodore Roosevelt level.

Yeah, yeah. But anyway, it’s great, great stuff. Really well written by one person. The audio book. Unfortunately, each audio book is read by different person.

The first one I found the the reader to be way above average, like excellent. And the others are fine.

But the first one was like, oh really, really makes that’s how you consume the audio. Yeah.

Audio. But I don’t think I could have consume this any other way. Three really. I think it’s audio book. It’s twenty five hours each.

OK, so each. Each.

So you’re talking like seventy five. Seventy five hours. I’m about sixty five hours into it. Wow.

So yeah. But anyway I’ll save that for my next cross-country trip. Yeah. Or I mean maybe I’m just recommending there are other shorter biographies but I mean some of the details, I mean the details of when he went out west, you know, I’ve heard folklore stories about him in the past that you think that can’t be you telling me after he was governor of New York, he took off.

The West and then, like, lived with a couple of guys in a cabin and hunted in the middle of North Dakota and yeah, he did and it was real. It wasn’t like, oh, you know, kind of did it, but it was all for publicity.

No, no. He just did that, you know, that kind of thing. Even his whole, you know, the war in Cuba, you know, but the Roughriders, that whole thing, reading about it and finding out that it’s not you know, it seemed the legend was too good to be true.

Did he actually do all that stuff? And it’s like, well, yeah, apparently he did really do all this stuff that would just be unheard of by anybody today.

So anyway, that does sound like a lot of fun. Yeah, let’s see.

So on my side, I want to let people know about an article that just released a couple of days ago called What’s Up with what’s terms of Service? There’s a link to it in the show notes basically. I think it’s been a couple of weeks now, but WhatsApp had a big old kerfuffle about their privacy policy changing and people feeling that they were being almost threatened if they didn’t accept the privacy policy somehow change that was going to somehow expose more data to Facebook.

And I think a lot of people this is how they found out that Facebook owns WhatsApp anyway. There’s more to it than that. It’s not as as scary a deal as a lot of people seem to make it out to be.

So if you want some amount of clarity or confirmation that WhatsApp either is or isn’t as good or as bad as you think it is, WhatsApp, what’s up with WhatsApp? Terms of service is the article.

About a month ago, we had Kay was on the show as he appears some times, and he talked about the Raspberry Pi for hundreds, though all in one looks like a keyboard computer that you want to sit next to me.


So I got one, too, and I did exactly what I think I might have mentioned in that show or maybe afterwards kind of planned to do was to see how it works with the Apple ecosystem. I basically just, you know, can I access iCloud Dotcom with it and look at all the files? Can I do other things? You know, you have a house full of Apple computers and iPhones and iPads. How can you use this to fit in with that?

You know, can you do screen sharing, for instance?

So I, I got one and I tried all those things and I did a video on what I found. The answer is yes.

But you know, it it’s a yes. But it’s a qualified qualified. Yes, qualified.

But so I’ve got a video on the Raspberry Pi and how it will work with your Mac. All right.

Well, that sounds good. I got pretty much wraps us up for another week, don’t you think? Yeah. The show notes for this week.


If you’ve got a comment or a question, be sure and hit us up on Facebook and Twitter @thetehpodcast. Or you can always leave a comment on the show.

Notes page. Thanks, as always, for listening and for listening to me blather on about Leo origin story by history. We all love to talk about ourselves. Next week will be Gary’s turn.

Thanks again and we will see you next week.

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