Advent of Computing - Episode 33.5 - Brad Chase Interview, Marketing Lead for Windows 95 and Much More

Episode Date: July 5, 2020

I recently got the chance to sit down and talk with Microsoft alumni Brad Chase. He was the product manager for Microsoft Works on the Macintosh, DOS 5, DOS 6, and the marketing lead for Windows 95 as well as much more. We talk about the Apple-Microsoft relationship, the groundbreaking launch of Windows 95, and what it takes to sell software. Editing for this episode was handled by Franck, you can follow him on instagram: www.instagram.com/frc.audio/ Like the show? Then why not head over and support me on Patreon. Perks include early access to future episodes, and stickers: https://www.patreon.com/adventofcomputing

Welcome back to Advent of Computing. Today, we have a slightly different episode. We have an interview on our hands. Listeners may recall that recently I ran an episode about the early relationship between Apple and Microsoft. As luck would have it, a few weeks after that episode dropped, I got an amazing chance to talk to someone with insider knowledge on the matter.

So today, I'm excited to share with you my interview with Microsoft alumni Brad Chase. During his career, he worked as a product manager for Microsoft Works, an early office suite that was targeted at the Apple Macintosh. But over the years, he'd also spearhead much more ambitious projects, the most well-known being the release of Windows 95. In this episode, he shares a little bit about the Apple-Microsoft connection, a little bit about Windows 95. In this episode, he shares a little bit about the Apple-Microsoft connection, a little bit about Windows 95, and a lot more about what it means to make software marketable. So without further introduction, let's get right into my interview with Brad Chase.

So I have with me today Brad Chase. Now, his resume is a little too long to list here. He's worked with a lot of companies and has a lot of accolades. Most importantly, for our purposes today, he worked with Microsoft. He was a product manager at Microsoft starting in 1987 and stayed on in the company until 2002. He was the product manager for DOS 5 and 6 and the marketing leader for Office and Windows 95. He's also the author of a new book, Strategy First, How Business Wins Big. Welcome to the show, Brad. Hey, nice to be here, Sean. Thanks for having me. Of course. So first off, I think a great question to start with is what exactly does a product

manager or a marketing leader do? I feel like a lot of people who aren't in the tech industry are probably a little bit unfamiliar with those titles. Well, it's different in different companies. So at Microsoft, in my days there, a product manager was the marketing leader or part of a marketing team for a specific product, like let's say Microsoft Office or Microsoft Windows, and worked with development to help ensure that products got built that reflected customer needs and what customers were aiming for, but at the same time also did all the things to market the product to the industry. You know, that related everything from PR to advertising, distribution strategy, designing at that time boxes for the software product and stuff like that. So how did you get into that field?

Well, that's a longer story. So I will tell you the highlights of it. But basically, I was in sales, which was a great early career out of college for me. And my father built a Heathkit computer. Heathkit at the time was a chain of stores where they had do-it-yourself kits, and you could build things like TVs and radios and other electronic devices. And he built this computer, and the computer was gigantic. It had a separate CPU with a keypad. It had a separate large machine, basically, in a way that was hard sector, eight inch floppy disks. And then it had a separate monitor and it ran CPM and hardly

had any memory. And once he built it, he didn't really know what to do with it. And he decided that he was going to give it to me. I stuck it in the apartment I was renting with someone at the time, started playing with it and using it and decided personal computers were going to be the next big thing. But I was kind of too old that time in my early 20s, I thought, to go back and learn how to program. Although I did take a basic programming class just to familiarize myself a little bit more with the industry. And I had taken, believe it or not, a Pascal class in college. The classics. Yeah, the classic. That's right. That's a great way to put

it. So I decided I would go back to get a business degree and get into the tech industry. And that's what I did. I went to Kellogg, which is the MBA program at Northwestern, and then interviewed with a number of companies with my top choices being Apple and Microsoft at the time. And I got a great job in Microsoft. Definitely seems like Microsoft would have been one of the best places to be for someone interested in personal computing in the era you started. interested in personal computing in the era you started? Yeah, it was fantastic because I basically got to watch Microsoft build a strategy for success in the PC industry and then execute successfully on that strategy. So that's where I got some of the most important sort of lessons on strategy that are central to my book, Strategy First. And especially being right in the nitty gritty of it

when Microsoft was working on going more towards direct-to-consumer, right? Yes, it was, you know, I was in the middle of all of it. You know, the early days of the Mac, the early days of the PC, the relationship with IBM, all those early things I was involved with at one point or another. And then of course, the record-breaking sort of iconic launch of Windows 95. So you mentioned Apple, and I think that oftentimes the relationship between Apple and

Microsoft, nowadays at least, is talked about in sort of adversarial terms. So working with Microsoft in that early period, what was your experience of the relationship between Microsoft and Apple at the time? So I was the first product manager, sorry, not the first product manager, but my first job was I was a product manager at Microsoft Works for the Macintosh. And then later I had Microsoft Office for the Macintosh under me as later I had Microsoft Office for the Macintosh under me as well. And we worked a lot with Apple and the relationship was fine. I actually did a number of promotions with Apple when I was the product manager for Microsoft Works. So this was circa 87, 88. And that relationship worked quite well. For example, Apple would want to reach small

business and my product was a small business product. So Apple ran a promotion where if you bought a Mac, you get Microsoft Works for the Macintosh for free. And so we had a lot of promotions that worked very well together. And the issue at that time was more on Apple's side than it was on our side. They were always a little tense about the relationship and sort of the coming of Windows, which they feared. But at the same time, the top three applications for the Macintosh in the early days was Microsoft Word, Microsoft Excel, and Microsoft Works. And so we were big supporters of the Mac and what we called at that time GUI, the graphical user interface, G-U-I. And that led to a sort of a way we could work

together, even though our interests were only aligned some of the time. Gotcha. All right. So then next question I want to ask you is, I read that you were the manager for DOS 5 and DOS 6. Now, it seems like it would be kind of hard to figure out a strategy for selling something like Microsoft DOS because it's not the most exciting software for some. So how did you go about doing that? And what were the big lessons that you learned during that experience? So after my days working on Macintosh applications, I did get recruited to lead the marketing of MS DOS 5. And what made MS-DOS 5 particularly exciting that time were a number of features that at the time for MS-DOS were exciting, but overall, you might not

look back at and say, wow, those were incredible features because they, you know, things like a new editor weren't or aren't very exciting in retrospect. But the big thing that was happening with MS-DOS 5 was it was the first time we did an MS-DOS upgrade. So at that time, the only way to get a new version of MS-DOS was to buy a new computer. With MS-DOS 5, for the very first time, you could buy an upgrade product at then like an egghead store or something. And that product would take your current version of MS-DOS and upgrade it to MS-DOS 5 and then later MS-DOS 6. And that's what was really exciting. And there were, as a lot of your readers will know, a very large contingent of very technically savvy users who love to play with the sort of innards of MS-DOS.

And so the way we marketed MS-DOS at that time was, A, you could upgrade to a new version and sort of freshen up your PC, which was true. And we would go around to user groups and enthusiast users and teach them about all the new features. And it was very exciting. I mean, people ironically waited in line to buy the MS-DOS 5 upgrade at midnight when it launched. So that was pretty exciting. On MS-DOS 6, it was a few more features, disk compression, and some other things probably were the leaders of the pack of new features. And the playbook was pretty much the same. I managed both development and marketing for that release. And that was the last major release of MS-DOS 6. And there was a lot of fun things we did in both those launches. For example, on MS-DOS 5, the launch event was actually held in New York

City on a large boat, which we coined DOS Boat. And we had Dave Brubeck perform at the launch, and he naturally performed his very famous, iconic jazz song, Take Five. That is fantastic. So just as a side question, how exactly did you guys manage to get a boat for the launch event? Is it just a matter of having enough marketing capital to do that? Oh, well, that wasn't hard at all. There's various places you could just rent them. So that's all we did is we rented it. We didn't buy a boat for it. There was some yacht. I don't even remember the details now, but you could rent yachts and we just rented a yacht for whatever a week. So we could, you know, set it all up and, and have the event on the yacht. So another question that's occurring to me is I

know early on for Microsoft and for Bill Gates, especially the topic of piracy was on his mind. Even as early as the first basic release, Microsoft software was already getting pirated. Did you ever have any issues with piracy that impacted your marketing or product strategies? Definitely. We had a lot of issues with piracy at the time. In fact, in Asia in particular, when I would do trips there, I would be shown all the pirated product that was available for people to buy really inexpensively. So, for example, on the MS-DOS products, we went through quite a lot of anti-piracy sort of protections that we put into the product or sort of the material. So, for example, we did a lot of work on holograms back at the time. for example, we did a lot of work on holograms back at the time. So you could know what an authentic product was and the hologram was very hard to copy and get an authentic hologram.

We did numerous things like that. We never protected the software so that we didn't want to ruin the customer experience, but we did do a lot of things. And also our legal team, you know, would track down people who are counterfeiting or pirating software where we could. Gotcha. This brings us, I guess, naturally to the launch of Windows 95, which is often cited as a groundbreaking event for software marketing. So with all the buzz around it, what do you think were some of the best choices you made when launching 95? What do you think were some of the best choices you made when launching 95? So with Windows 95, you know, if you go back at that time,

computers were still more of a hobbyist machine. They were starting to get used in business. Windows 3.0 and Windows 3.1 were pretty successful. The Mac had smaller sales, but was a good machine. And, you know, I decided that the of trying to hide everything going on with Windows 95 from customers and the industry, I would flip that sort of normal playbook on its head, and we would start telling people what was coming. And the idea was that if we told people what was coming with Windows 95, then they wouldn't be so scared to upgrade to it. And on top of that, we would get the industry building

lots of products for Windows 95, whether it be new hardware, like keyboards or printers and so forth, or new software, like Microsoft Office 95 itself, for example. And then getting consumer enthusiasm would then sort of roll into businesses where consumers would want to run Windows 95 at their work as well. And so the Educate, Excite, and Engage strategy had the ultimate goal to turn Windows 95 into a consumer phenomenon. And the strategy was really successful because the team that worked with me, that worked for me, was just really good. And we had different teams on different customers. So one team worked on, you know, educating and exciting and engaging consumers. And another team worked on with the third parties.

And another team worked with business. And, you know, another team worked with the press and so forth. So that worked out really, really well. and so forth. So that worked out really, really well. And the underlying secret sauce of all this was that Windows 95 was a great product. We built a great product. The development team did an awesome job. You can't market your way out of a bad product in the software industry, but you can take a great product and make it even more fantastic. And that's what we were able to achieve. And I told the team we reached the goal about a week or so before launch when Doonesbury ran a week-long series of strips, comic strips,

making fun of Windows 95. And of course, if you were there then, I mean, Windows 95 was on the cover of every magazine. And it was talked about not just in the computer press, but in the consumer press. And it was sort of hard to tone down all the talk about Windows 95. But that Doonesbury strip, I remember, sort of iconically represented that we had reached our goal to make Windows 95 a consumer phenomenon, which, of course, was topped off by the launch event, which was a circus we built on the campus, on the Microsoft campus, with Jay Leno as the host of the event in the sort of the big tent. And lots of third parties had tents afterwards with their products. And that's also where we debuted the now infamous, well, actually not infamous, famous Windows 95 Start Me Up launch commercial with the song Start Me Up by the Rolling Stones being the background song in the commercial. Yeah, the iconic commercial. So you mentioned that a big shift was making the development process of Windows 95 more open

to the public scrutiny. Was there any pushback within Microsoft to making that move? Yeah, there was some, but everybody got on board fairly quickly. There was a lot of reasons to always be concerned about that. Because when you start talking about a future product early, it dampens your current sales and tells your competitors what you're doing. And so there was a lot of concern about those two issues. But ultimately, we had a goal to make Windows 95 very compatible with pre-existing products. And so doing a large-scale beta helped to make the product quality higher. And then we expanded that also to do sort of preview programs and throw stuff in computer magazines like demo disks and stuff so that people had a very good understanding of Windows 95. So

the downsides that I just mentioned were quickly overcome by all the positives of product quality and marketing that came out of doing the large scale early beta and the preview programs. So with the Windows 95 beta, was that a totally new thing for Microsoft to do on that scale? Or were there smaller scale betas for earlier products as well? There was both. There were smaller scale betas for earlier products, like the MS-DOS products we talked about earlier. But the Windows 95 beta program, which my memory is a little fuzzy, I think it was 400,000 people, was a new scale. I mean, we just went to great lengths to try to have high quality.

One time I remember David Cole, who led development for Windows 95, took his truck and went down to the local Egghead software store and bought one of everything. And then threw it in the truck. The store manager for Egghead probably had his entire year quota made on that day. And David drove all that stuff back to Microsoft and made sure it was all part of the testing suite

for Windows 95. So we just did a lot to really try to ensure product quality. I don't remember all the details now. Here and there, there were probably a few products that didn't work great with Windows 95. But by and large, Windows 95 did a great job of making it easy to move to Windows 95 because it was very compatible with the wide variety

of software products that existed before it launched. Yeah, so basically building up a software solution where there's no downside to upgrading. Yeah. I mean, it was almost all upside. The only downside was you had to learn the new user experience, which was so dramatically easier that most people picked it up very quickly with the iconic start button and just how well it was put together. Some people, for example, a guy like Joe Belfiore, who worked at Microsoft, who still works at Microsoft, actually, did a great job, you know, sort of leading that design. So it was really a really, you know, a wonderful product because it had so many cool new features like, you know, plug and play and preemptive multitasking and this really easy to use experience with sort of headed by the start button. So in the development period for Windows 95, and I guess also in marketing it, were there ever any challenges in trying to make it stand out?

Because by that time, like we've already mentioned, the Macintosh was a big thing as far as competition and it had a somewhat similar user interface but there's also things in the market like the Amiga or Atari computers with graphical interfaces yeah it was the Mac was the Mac and OS 2 were the the main competitors at the time the others were not didn't have significant volume and weren't major or even minor factors, really. You know, the main advantage Windows had, it was fresh and it would be on so many computers. You know, the business model Apple had at the time, of course, and still to this day, is that the Mac's only available on computers built by Apple. And so Microsoft, by having the strategy with MS-DOS and Windows of having those products

available on lots of different computers allowed software manufacturers to know that there'd be a big audience for their products, allowed hardware manufacturers the same. And, you know, there was a lot of innovation too in the Windows 95 experience that even Apple didn't have. I mean, at the time, for example, people loved that you could right-click and do all these things with Windows 95 that you didn't have that option on the Mac. So the Mac was a very good machine. Software is excellent. Certainly Windows 95 learned from the Mac experience and later the Mac from Windows 95.

But the sheer sort of volume and excitement around Windows 95 is what led it to be the leader. And excitement around Windows 95 is what led it to be the leader. So one of the things that you mentioned was you had to market to customers, but also to OEMs and third parties. Was there a big difference in the marketing strategy used for that? Like, did you have something like the Circus release event to get the OEMs excited about the product? Well, OEMs were invited to the launch event, of course, as were lots of partners. And as I mentioned earlier, at the end of the launch event, the back of the tent opened up and ushered you into the sort of the fair with all the tents that were manned by third-party companies that were showing off their Windows 95 products. And oh, by the way, it was really special because the walkway, so to speak,

into the sort of heart of the circus or the fair had on either side of it, all the Windows 95 developers wearing t-shirts that were the colors, the four colors of the Windows flag, the Windows icon. And so you walk through the developers to sort of celebrate what they built with Windows 95 to get to the fair. So that part was all the same. But of course, leading up to the Windows 95 launch, we worked in many different ways with third parties. You know, for example, we had to work with PC manufacturers on both the timing and the technical aspect of Windows 95 to make sure they could preload it and have it ready on their machines when we launched on August 24th. And to get them excited about it, we did many presentations to them. You know, they were sort of leery to have a new

software product on their machines the day of launch. But again, the consumer excitement sort of forced their hand. In terms of software developers, we had numerous events to teach them about Win32 and writing 32-bit programs for Windows 95 and how that would all work and getting them excited about it and evangelizing them. So there was definitely, you know, working with hardware software developers, training, people doing training videos and books. You know, one training company actually came out with a training video for Windows 95 that had Matthew Perry and Jennifer Aniston as the people teaching people, the viewers of the VHS at that time, how to use Windows 95. So, you know, people did a lot of creative things and we had to market differently

to educate and excite the industry than we did with, say, consumers or technical leaders in companies or technical savvy users or just plain old consumers. So that release was a lot different from your earlier projects, right? Well, yeah, because it was so broad. I mean, being the product that ushered computers, arguably Microsoft and Bill Gates into the mainstream was just a very different animal. Though we had consumer elements of launches for like MS-DOS 5 and MS-DOS 6, you're talking a single A level of

effort and reach versus being in the major leagues with Windows 95. So was there a lot of carryover from earlier products like the DOS releases into 95? From the marketing aspect or from the into 95? From the marketing aspect or from the development aspect? From the marketing. There was some carryover, but mostly it was a new playbook that we were, you know, sort of implementing for the first time. All the stuff we did about Educate, Excite, Engage, the E-Strategy I talked about earlier, a lot of that was innovative and new at the time. We had never done anything like it. That was the first time the Rolling Stones had ever allowed one of their songs to be licensed for a commercial. And that whole deal is an

amazing story and fun story, which I revealed finally just this year, sort of the real story of what happened behind the scenes. And getting Jay Leno and building the launch event at Circus on the campus and all the marketing programs we did. I mean, it was just, you know, a new playbook and a whole new level of scale for software marketing. It was the iPhone launch of its time. If you're sort of weren't around then, a Windows 95 was bigger than I would would argue, probably than the initial iPhone. And the only difference is we didn't have the breadth of the internet that we have, you know, sort of with the iPhone launch and today with other launches. So after 95, did that change your relationship with Apple considerably?

Because now you're, of course, there are already editions of Windows out, but with 95, it's a whole other level, like you were saying. Well, I mean, our relationship with Apple was always complex. I mean, sure, it changed the relationship at one level, but on the other hand, Apple had more serious turn it around with Jobs' great strategy to refocus the company, Apple, I'm talking about, on devices and sort of consumer entertainment devices. So that relationship was always up and down. Bill and Steve had a good relationship, though, especially most of their time anyway.

And while there was certainly tension and competition, there was also sort of cooperation and Microsoft helped keep Apple alive. I think that's probably the best way to put it. All right. So that's all I have for you today. Thanks so much for coming on to the show, Brad. You're very welcome, Sean. And if you want to hear more from Brad, you can get his book out now, Strategy First, How Businesses Win Big. It should be in all booksellers by now, right?

Yeah, you get it at Amazon or your local independent bookstore, Barnes & Noble, wherever you want to get it, it's available. And people could also follow me on LinkedIn. I'm on LinkedIn as well, so they could follow me there. And my website is bradchase.net. All right. Well, thanks for coming on, Brad.

Great talking to you. All right. Thanks, Sean. Thanks for listening to Advent of Computing. I'll be back in about a week with another regularly scheduled full-length episode. And hey, if you like the show, then there's a few ways you can help support it. If you know someone else who's interested in the stories of computing past, then why not take a minute to share the show with them? You can also rate and review the show on

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