Pioneering Tech and Culture - Donna Dubinsky - Palm & Handspring - Episode #82

Stop kidding yourself and look at the reality here and know what you got. And know that you got a problem.

Welcome to Not Another CEO Podcast. I'm your host David Politis. Every week we talk to inspiring leaders and get the true stories, the ups and downs, the lessons learned and come away with actionable advice for our own journeys.

Foreign.

Dubinski Donna played a very important role in the history of personal computing. She was the CEO of Palm during its most influential years, helping turn into one of the fastest growing and most iconic technology companies of its time. Before that, she was an early executive Apple, during a very formative period in that company's history. After leaving Palm, Donna co founded Handspring where she once again shaped how millions of people interacted with technology beyond her operating career. Donna was on the board of Yale where she attended school and she is currently on the board of Twilio. She's seen technology cycles rise and fall, led through hyper growth, competition and disruption. And she has a very rare long term perspective on what it really takes to build and enduring companies. Please welcome Donna Dubinsky.

Thank you so much. Happy to be here.

I'm so excited. I've been waiting for this one for a while. So thank you for doing this. First question right out of the gates. What is the one thing that you've done, big or small, at your companies that's had the biggest impact? And you do again if you're CEO of another company in the future?

Well, I hope I'm not CEO of another company in the future. Let me start with that. I think I've had enough of that. But look, it's all about the people. It's about recruiting the best possible people from your executive team to your receptionist. I mean, a company is consisting of a lot of people and the better people you have, the better company you're going to have. And even if you have the wrong product idea or you're in a market that doesn't work out, the best people will be able to adjust to that and make a change and pivot. But it's all about finding those great people.

And how did you find those people? When you think about that, were these people from your network, let's say at Apple? Were these people, did you bring people with you along the way? Did you bring new people in? How did you find those great people?

Well, I'm trying to remember early in my career how we found these sort of initial group, but definitely people followed us from company to company and there was a lot of value in that because we you had trust, you'd worked together, you understood each other, you had shared values, and I found it really helpful to have people with us. I'll never forget resigning from Palm and sending out the all company email, and within minutes had a slew of emails from people in the company saying, can I come? Can I come? And it got to the point where I printed them all out and I kept them in a file folder for the day that did come when the lawyers from Palm came to me and said, you're taking too many people started handspring. And I basically said, look, they're coming to us. We're not taking them. I have the file folder full here of emails and, you know, feel free to come on over and take a look at them and read through them. And that ended that conversation really fast.

So.

So, you know, if you build a great culture and people really love working together and working with you, then they'll, they'll go with you to do the next thing. And, and I found that very valuable.

In our case, I think, I think that we take, at least for me, I think, as a leader, you don't realize how many bad cultures there are actually. And so when you create a great culture, it stands out in the minds of those people and they want to follow you where I mean, what you just said. You know, I was talking to a VC and they were telling me one of the things they look for, one of the big things they look for is to understand the team chemistry and the team makeup. And did the team of this company that's looking for investment work together? Did people follow the founder? Because that gives them a sense. If no one followed the founder to their third company, that's probably a bad sign.

So interesting that you say that, because I, I think I. I was really blind to how bad come other company cultures would be. To me, what we did in creating a company culture was natural. It was, of course. So it was confounding to me that other companies and other leaders didn't do it, but apparently it was quite unique. And even just recently, I had one of our former executives reach out to me, who I'm not in regular touch with, just to say, you know, I just want to say thank you. You guys created such amazing cultures. I've copied that in my own company was so valuable, and I don't even realize it sometimes because to me, it just was a part of who we were.

What, what, what were these attributes like? If you think about the best people that you've ever worked with, what was that one attribute or Those attributes that you were looking for in those people.

I think probably number one on the list was flexibility, adaptability. If people are too stuck in what they think and where they are and they can't break out of it, they can't adjust to changing situations. And when you're pioneering something new, the ability to adjust sort of consistently, constantly is absolutely fundamental. So I really appreciate people who could deal with change, change, changing circumstances, changing environment, changes within the company as opposed to people who were rigid. I even developed interview questions along those lines. It was like, tell me a time where there was some big change and how you adapted to it or whatever the questions were to try to get to the notion of change and flexibility.

I think that's interesting because what I say, one of my biggest mistakes was at all the companies I've been a part of is thinking I should go hire people from the big companies that have done what I had done, you know, in the same space or whatever, and go get the CRO who was at Google doing this even when we were a small company. And one of the reasons, actually now that you're saying it, one of the reasons that those people I think did. Weren't successful is that the change was, was constant at Google. They had their plan for the year and they could do that thing and the comp plan was the same and every, you know, and, and we were changing every, I mean, I don't know, week, you know, month. And, and the oscillation was making them crazy. And, and, and so when you, I think that that really, that's a, that's a interesting point for founders. Again, most people listening to this are earlier stage founders. And it's like when you're in any early stage company at any point in history, you are going to change is literally constant by the day. And you need people to go along with that.

I'll give you a little treat, a little gift. Which is my favorite interview question of all.

Oh, I love it.

Okay.

I love it. Okay.

Favorite interview question is just tell me a time when you were really frustrated and if the person responds and says, oh, things were changing constantly, it was, we had one goal one day, we had another goal another day, then I know it's just my person. And you know, if they say, oh, the situation was changing around us and we weren't adapting and nobody was listening, then that's my person. So what? The word frustrating got at people in a way that they didn't feel as tricked by the question and they could answer very honestly about when did they Feel frustrated.

Yeah. Again, I like that. I like listening in the interview for when people talk about, they'll say, oh, my last company, the CEO was always changing their mind and it was so frustrating. Or, you know, my comp plan kept changing. And when you can believe that your company as the CEO, that you're different, but in reality you won't be, and it's better just to look for that person who can go with the flow and maybe later stage, that's different. I don't know. But in that first years, as you're building, that's, that's critical now, mind you.

You don't want to change every single day. I mean, there is, there is a balance here, so let's not go overboard. And some of that frustration would be deserved. But generally speaking, I think for an early stage company, people who are flexible are just critical.

And so when you think about the culture of the company, this amazing culture you built at multiple companies, what was the centerpiece of that? What rituals, what traditions? Where was the core of that? Where did that come from?

Well, I think it's a few different things. We would go through those processes of articulating our values and talking to everybody about what was important to them. I remember when we started Handspring, we gathered all the early employees around and said, let's just talk about what we've loved about our prior companies and what we've hated about our prior companies. And how do we develop a set of values together that enable us to build a culture that we really like. And so really trying to extract from people those experiences is important. But a lot of it has to do with integrity. It has to do with communications, making sure everybody knows what's going on. It has to do with having fun. We were very keen on making sure that we were enjoying ourselves. We incorporated the families. We tried to make sure we had, you know, a family event at least once a year where you'd bring your kids. You know, we. There were just a lot of different elements of it that made it feel like a place you wanted to be in a welcoming place.

I, I want to go on the communication front for a second because I find that there are a number of people, again, founders I talk to who they feel like it's so much work to, to communicate, prepare the communication, do the all hands. Like there's always this thing of. But that's going to take me so much time and that. And I could be doing this and the people don't need to hear it for the 15th time. But I Think communication is when you, you know, when you think about, as any human being, you want to know what's happened. You want to know why you're coming to work every day. You want to know like, can you talk a little bit more about how you would communicate? Would you have to repeat yourself? Would you have to like, how did you, how did you do that?

You definitely repeat yourself. And yes, you do have to do it for the 15th time. It starts even with orientation. I remember I did orientation in my companies even when they got very big.

I didn't care how many you, you met with the new, you met with the new employee.

I personally wanted to meet with all new employees, maybe not one on one. As it got bigger, it'd be with a group, but I personally would meet. I had an orientation debt. What are our values? What's important to us? What's our history? I wanted them to hear it from me. And I continued to do that in my various companies. So it starts right at the very beginning. It includes a regular communication stream, whether that's all hands meetings or updated emails or what have you. There's lots of different ways to do it. I had a very rigorous planning mechanism that I sort of instituted through all my companies the exact same thing because it worked so well, which was we did a yearly, well, I guess a twice yearly planning process. And we would have an off site two times a year and we would do a plan for the rolling 12 months. So effectively you'd be planning the next six months, which was a revision from the prior plan, and adding six months, which was the next six months to take a look at. And we did this both at a strategic level of what are we trying to accomplish, what are our goals and at a budget level, what are all the numbers and how do they roll up and what changes do we need to make? And we would do an off site with our executives every six months to go through this plan. It would give us a chance to remind everybody what our goals are, to scan the environment and say, what's changed? Has anything changed that we needed to adjust to competitively, macroeconomics, whatever, what's changed? It would give us a chance to reflect on our performance. Okay, let's look at our goals from the last time we had this meeting. Did we do them? Didn't we do them? Where did we fall short? Why is that? How do we feel about that? And then to plan going forward the next six months. And I found these extremely valuable. I thought the funny thing about it was every time we were Coming up to one of these meetings, my executives would start whining about not having the time to prepare, prepare for it and go off to it and not wanting to do it. And it was always a little, you know, maybe a little uneasy. And then we'd get to the meeting, we would always have like a tremendous meeting. And afterwards everybody would say to me, that's the best one of these I've ever been to. And this became such a pattern that I learned to ignore the whiners before the meeting because I knew it would work out okay. But it was really just a time for reflection on a regularly scheduled basis. That worked well for me and my.

Team because you don't really get the time in the weekly exec meetings or the one on ones. Like, it's just when you're in the weeds, you don't have the time to really step back and force that reflection to that degree. Right. I mean, when you're doing the off site, people prepare for it, they come there, they're locked away somewhere and like it just forces it. Right. I think, I mean, what you're saying, it kind of fors a different way of thinking, looking at the business in a different way. And, and I think also just the spending time together, right?

Absolutely. I mean, in terms of the forcing to think about things, what happens in the day to day is you get mired in operational details and these are important and you have to deal with those and you don't have the chance or the time to think more strategically and the offsides force that higher level thinking and understanding the implications for operations. And then as to your second point, absolutely. It was also to have fun. As I said earlier about culture, you know, we always had fun activities associated. It was team building. You want to build respect and enjoyment of each other. And I think that that meant a lot to people that we were willing to invest in that and that there was always some fun activity, whether it was bowling or kayaking or whatever goofy thing I could come up with. There was always something fun as a part of those meetings as well.

And would, how often would you actually change.

That?

You know, would you modify your strategy? When you said about looking about the landscape and figuring out what's going on, like, how often were you actually changing that? Was that most of those times or most of the times you were just staying the course, reconfirming, you know, reviewing. Like how often was that adjustment happening?

I'd say there were always tweaks. There were always tweaks in the strategy, some shade of Something one way or another or some organizational change because something needed to be closer to another thing. In terms of major strategy changes, they were less frequent, so they may have been every couple of years.

So you knew kind of that's where we're going three years from today, for example. But on a quarterly basis or every six months, you were tweaking how you were going to achieve that. Is that a fair. Like, you knew where you were trying to go?

Sure. That's a good way to think about it. Yeah.

I want to take a step back and talk about the Palm story, because I actually, I've been reading a lot about it to prepare for this, and, you know, you shared it with me. Can you maybe share, like, a little bit more of the backdrop of that story? And because you really were at the beginning of a. I mean, really something that changed the world, you know, in terms of personal computing, you were at the. Literally at the beginning. And so can you maybe talk about that journey and kind of the arc there of the market and, you know, where you were in that?

Sure. Well, maybe let me start with stepping back a little bit. My own sort of career experience, my career arc. I've been on the forefront of four major computing revolutions. So starting with personal computing, joining Apple in its very early days, then handheld computing with Palm, then smartphones with Numenta, then Intelli. I mean, smartphones with Handspring, and then intelligent computing with Numenta. And each of these has been a massive new wave of computing. And what I learned from my experience at Apple, having worked with Steve Jobs and in the early days of personal computing, is how exhilarating it was to be on the frontier and to be creating new things that changed the world, that changed people's lives in fundamental ways. And I got kind of addicted to that. So after I left Apple and Claris and decided to take a break and then come back in the industry, I was deliberately looking for something that might have that same impact and that same kind of exposure to big ideas. And along that path, I met Jeff Hawkins. Jeff had just started Palm Computing, and he brought out a little Sony Palm Top. I should have brought these show and tell with me, but Jeff brought out a little Sony Palm Top, and it was only available in Japan. It was a handheld, early handheld computer. And he said, this is the next generation of computing. And I felt that same rush that I felt with Steve Jobs of looking at desktop computing and taking computers from the RAISE4 computing room onto the desktop. And this was, wow, now they're gonna move from the desktop into your pocket. That is amazing. That is just amazing. And I got totally excited about joining Jeff on that journey. So that's sort of how I ended up arriving at Palm shortly after it was founded. And at the time there was nothing like that. There just were no real handhelds. There was that little Sony device, but there really was not much of anything. And Jeff had a vision of a software intensive handheld device that could take computing from your desktop into your pocket. And that's how it all started.

And when you were like to build that, were you having to change the mindset of consumers, like to explain what that was and how to use that? How did you look at the competitors that were in the market at that time or the people coming into the market at that time? I remember those, that, that first Palm Pilot and it was, I mean that was a huge deal at that, at that time. Like you completely changed the paradigm. But was that something that was hard to get people to understand or that was right away you put it out there and everyone's buying it.

As soon as we produced a product that was highly useful, people got it right away. Now let's remember we had a failed product first, so we had the Zoomer first, which was a product we did with Casio and GeoWorks. And that product was a big failure at Palm. And we learned a lot from that product. We learned what we did right, what we did wrong, and then we created the Palm. And the problem was at that point in the market was it was impossible to convince investors that this was a good idea because there had been so many massive failures, including our own, that people basically wrote off the whole category of handheld computing and said, this is stupid, we're not going to do it. So it was never the problem of convincing consumers. I mean, once we shipped a great product, I. E. The Palm Pilot, consumers came on board and drove. It was very, very fast. But it was a huge problem convincing investors. Wow.

And how like you had, I mean, you had experience at Apple, you know, Apple at that point already a formidable company. You're going out pitching people you couldn't get. Like you didn't have any connections. That was, I don't know what the investment landscape was like at that time. Like, were you going to people that knew you, that you knew in the market, or was it all fresh? Like you're showing up out of the blue. Let me pitch you.

When we first managed to get money for Palm, it was not hard. We got quite a few quality investors for Pomp. But after we had this Failure. Then it became almost impossible. In fact, it became impossible. And we came up with the idea for the Palm Pilot. I mean, Bruce Dunleavy, one of our early investors, he was at Benchmark. He came to us and he said, okay, you guys, now that you've been through this Zoomer thing, what did you learn? And what would be the way to do it? Right? And literally, Jeff went to his garage. It's just such a apocryphal story. Went to his garage, created this little model, came back the next day with a model of what became the Palm Pilot, just a wood thing, and said, this is what we need to do. And we all got really excited based on what we'd learned and that this was what the. The right answer would be. And we set off on a path to build this thing, but we didn't have that much money left. We had enough money to get through the development. We just didn't have enough money to launch it. So we kept going down the path, down the path. And then we started going out for money. And at that point, sure, I knew everybody in Silicon Valley, I assume. Yeah, yeah. And I knocked on every door in Silicon Valley. I mean, I. I talked to every single major investor in Silicon Valley at the time, and. And absolutely zero investors would come to the table to support this. Now, part of that was the Zoomer experience, for sure, but another part of it, in fairness to them, was the Internet had just started exploding. I mean, I know it's hard for your listeners, viewers, to imagine a time before the Internet, but there was a time before the Internet, and now, all of a sudden, everybody's on the Internet, all these new businesses are churning, all the AOLs and. And yahoos and so on and so forth, and all their attention was turned there. And hardware felt very retro. Who wants to go build a piece of hardware? You got to be kidding me. That's not the future. That's the past. So it was impossible to raise money for this new device. And. And even, you know, Bruce couldn't convince his partners at Benchmark. You know, it was just, wow. So. So we ended up selling the company in order to finance the Palm Pilot. So that was the bottom line. That was the only way to get the money to bring it to market.

And so once you sold the company, that's really when things. I mean, that was when. Who was it that bought the company?

So we sold Palm to US Robotics, based in Skokie, Illinois, and was sort of the leader in modems at the time.

And then that was when really The Palm took off, was it after that acquisition?

Yeah. Well, we hadn't shipped it yet until we didn't have the money to actually buy the engine.

Oh, you couldn't even. Oh, you couldn't even. Oh, wow.

Yeah, yeah. So we shipped it as a part of US Robotics, and it was really amazing. I'd say we did 10,000 units a month in the first five months, and it just sort of bubbled along, bubbled along, and then it just took off. And every one of those early 50,000 users told everybody they had to buy this thing. They became our salesforce, our early users. And we ended up selling a million units in 18 months or something, which had never been done by any consumer product at that point. It was the fastest product adoption in history at that point. It's been exceeded since then, but it was really a massive adoption rate very early on.

Did you know the entire time not being able to fundraise all the. Like, did you know it was going to be successful? Like, were you. Did you believe with all the no's, with everyone saying, we're not going to do this, like, did. Was there any wavering with you and Jeff at that. At that time?

You know, it's hard to remember what you were thinking at the time, so, you know, easy to look back. I don't think anything was obvious. We'd been through a failure. You know what was going to happen. I'm not sure. I was more embroiled with tensions with my US Robotics executive team at the time that I think that was preoccupying me more than anything else. But, you know, we were using the product ourself and we knew it was great. And that was, you know, really important to really believe it. And you gotta not kid yourself. I'll never forget a story back when I was using the Zoomer and I was demonstrating it to Jean Louis Gasset, who was an early Apple executive, and the Zoomer. One of the problems with the Zoomer was it was super slow. I mean, you would tap something and you'd wait and wait. And I had learned in a demo to, you know, talk over that. So people weren't so aware of the fact that it was so slow. So I would be demoing happily away. And I was demoing to Jean Louis and I was chattering away, and he goes, donna, it's really slow. And I'm like, no, it's got this, it's got that, and blah, blah, blah, blah, blah, blah. And he's like, donna, listen to me. It's really slow. And I remember this moment. You know, there's moments in time that it was bigger than his point. It was like, stop kidding yourself and look at the reality here and know what you got and know that you got a problem. And so I really took that to heart and I tried to be a lot more critical as I looked at our products. I used them myself. Is this a problem? Is that a problem? And not being so, you know, closing your eyes to reality.

That's such a good, when you're saying that I'm getting, I'm thinking of all the moments in my various companies where you have, you have that moment and you do, you either don't see the problems or you force yourself not to see the problems, or you don't want to admit the problems. And the customer is seeing if, if you're, you know, the customer's seeing it and, and you think like, no, no, maybe they're not noticing that that button doesn't work. You know, like, of course they're noticing. Like, it's kind of, it's crazy to think otherwise. But, but you're, you know, I, I, that's a really good, that lesson is such a good lesson of just being really hyper aware and honest with yourself.

You know, I mean, look, it's totally understandable. You want to be a cheerleader, you want to be a champion, you know, and you want to be a salesperson and all those things, but particularly if you're the CEO, boy, you gotta be real. I used to read every email I get from customers and it drove my team a little crazy, honestly. I would respond to these random consumer emails where they were usually complaints about something because people don't take the time to write you, to just say how wonderful you are. So I would escalate these things over and over and it drove my team crazy. But I will time and time again, I found problems in the field before they were reported up through the regular networks because somebody took the time to write to the CEO.

Wow.

And so I just became totally convinced that that was listening posts that I needed to have. And, and often, I mean, I couldn't solve them. I would just say, I'm going to look into this. So, and it was really funny for a while. People started, there were little chat boards and stuff where people were saying, oh, that's an automated system. She can't possibly responding to those things. Like, no, I was really responding to those things.

That's a good that, I think when you talk about culture, by the way, that that's probably a part of the culture. When people see the CEO doing that, even if it annoys, I'm sure it did annoy some people on your team. They also see that you're doing that. And if that means customers are important, I think that says a lot. I don't know, Jeff, but I'm assuming based on the products that he's built and that you've built with him, he sounds like a product genius and just a visionary. And then you, you mentioned you worked at Apple, obviously with Steve Jobs. Like, how was it to work with the, you know, to be the counterpart to that side of the brain? I don't know how much of a product brain you have or how much more. Clearly you're the operator. But, like, the question is, how was that? Like, how. How did. What. What challenges that did. Did that bring? And, and what. What was fun about that?

Well, you know, people like Steve Jobs and Jeff Hawkins, who are very different people, so it's hard putting them in the same box there. But, you know, it's totally inspiring. You know, they have. I have found there's just a certain set of people have a unique ability to challenge conventional wisdom, see things differently than the rest of the world, go to core principles and not to what sort of has been layered onto things. And that's what Jeff did with the PalmPilot. You know, the prevailing wisdom on the Palm Pilot when he about handhelds at the time was a handheld should be a small version of a big computer. And that was what the Zoomer was. That was what the Newton was, Apple's product. And those were all failures. And Jeff looked at that and said, well, maybe that assumption is wrong. Maybe they shouldn't be a little computer. Maybe they should be an accessory to a computer. They should be the little piece of the computer you take around with you. And the implications of that change in mindset were enormous. The example I like to give, because it's just so easy to understand, is that, you know, at the time, everybody thought handheld should print right from the device. And actually supporting printing was extremely expensive. There were a lot of printers. You needed a driver for each one, you needed to test each one. You'd need an updating mechanism for it. It was actually a very expensive capability to have in your device. But Jeff said, hey, let's not print. Let's synchronize really well with the computer. The computer prints beautifully. They can print it from the computer if they want to print it. It's a device in a relationship with a computer, not as just a standalone. And let's partition applications. So certain pieces of it go on the device, certain pieces of it go on your desktop. And let's think about that. And it was that design philosophy that enabled a much smaller and cheaper Palm Pilot. So instead of this massive zoomer that was slow, as I said, that cost almost $1,000, we ended up with $199 small fits in your pocket device. And a lot of that was because of the design decision of what it did. But that was not conventional wisdom. That was a whole new thinking. That was what enabled the pump and then developing the syncing software to make sure that that syncing was seamless and worked well. That became core. So everybody would look at the hardware and think the magic was in the hardware, but really the magic was in the syncing software.

And yeah, when you say that, I mean, I could think about SaaS products, AI products, all have the same thing where you just. You say, well, I'm just going to do this thing a little bit better. I'm just going to. This is what the customer is asking for versus, like, what is actually needed. What's possible with the technology that exists. What's going to really change this, this paradigm, you know, to the customer, business, consumer, whatever. I think we all, I mean, except for those few people who really can just look at things from a completely different angle. It's hard. It's hard. You know, I. And that must be fun. Like, I've never worked with someone like that, but I can only imagine it's probably scary sometimes. They're probably coming up with all kinds of great ideas, but I'm sure it's a lot of fun.

Well, it's fun sometimes. It's definitely challenging too, but it's fun.

So you were there, how long were you at US Robotics after the acquisition?

Well, I stayed at US Robotics, and then surprising to surprise to me, one day I got a call that U.S. robotics was going to be acquired itself. It was acquired by 3Com, a Silicon Valley company. This surprised me because I was not involved in the discussions, even though I was on executive staff. So that alone was a bit of a surprise, obviously. And it also surprised me because at that point I'd really become quite disillusioned with USR and some of their strategies and what was going on in the company. And it surprised me that even though I immediately looked at three Comms board of directors and knew personally several members of their board of directors, nobody called me to do due diligence on usr to say, hey, what do you think? And here I was the one Silicon Valley person on that board. And I've always wondered about that. It was such an interesting miss. And when I've asked people there, why didn't you call me? I could have told you these things because it ended up destroying the company. It destroyed, really three conversations. And I said, why didn't you call me? I would have told you these things. And they said, oh, we couldn't go around the chain of command. And I've had this to several. Happened to me several times in my career where something didn't happen because somebody was unwilling to go out of the chain of command. And I talk about another cultural thing I've become a big believer in is letting people go around the chain of command because sometimes somebody's blocking a message that needs to get through, and that message did not get through, and it destroyed the company as a result.

Wow. And so you. So. So you. Did you go with the acquisition? Did you go to 3Com?

I went with the acquisition. So now I was a part of 3Com, and I immediately went to Eric Benimo, was the CEO and said, you need to spin us out. We don't belong here. This is a communications company. This Palm thing is something totally different. It needs its own path. And he agreed to have a review of that. We brought in bankers. We had a whole, you know, strategy thing. I was very committed that we needed to spin it out. Our bankers recommended that as well. Eric decided in the end that he didn't want to do that, so he didn't spin it out. And then I decided to leave and volunteered Jeff to leave with me. And we left and we formed Handspring. And that's when I started getting all those emails, as per earlier in the story. Go with us.

So how. How good did it feel to leave and start. And start a Handspring at that point?

Look, I loved Palm, and I loved the people at Palm, and I loved what we had accomplished. But it had been very painful. I mean, I'd been through one painful argument with U.S. robotics after another. Oh, my gosh. I just don't even want to relive those days. It was so difficult. I felt like I was always half resigning on every airline trip back from Skokie, and then I'd be back with my team, and after a few days, I'd be fine and happy again. But it was very difficult, and I just didn't want to go through that again with somebody else. And I remember once complaining to the guy who bought us at US Robotics, and he just looked at me and he said, next time don't sell. And it really struck me as one of those hard truths, you know, you sell and you got to be prepared to live with it or to go. And I just didn't want to go through this with another company. I mean it was tricky. And US Robotics and 3Com were as polar opposite of companies as you could imagine. US Robotics was very cowboy mentality, very seat of the pants. Whatever goes, goes. And 3Com was very bureaucratic, structured, rigorous company. I would get these@3com. This would crack me up as an executive. I'd have to do this monthly report and they would call me for this monthly report every month, which involved how many customers visits I'd had, how many corporate presentations I'd given, you know, blah blah, blah, blah blah. All these statistics that they were collecting because of their dashboards and stuff. And I never did any of those things because they didn't apply to my business. I was selling through retailers. I wasn't doing direct presentations. I wasn't selling modems and communications gear and switches and routers and hubs and so on. So I would just say 000 fill, right, just fill this spreadsheet right and don't call me again. You know, but they would call me every quarter. And it just that drove me as crazy as yours revives drove me. Which was, you know, all about the opposite. It was like whatever, whatever. And so I just found. And then I've decided maybe I'm just not very good at being an employee and I just need to be the CEO because I'm as frustrated with these two extremes as you can imagine.

It's so, you know, I've talked to so many founders who have sold their companies to bigger companies and this is, I would say 90, not 100, but 90% end up in this situation. I mean 90 end up in this situation. I talked to a guy who sold his company to Cisco and I met him a couple years later. I went to the office and I was talking to him and I said, how is it to be in Cisco? He's like, well, I'm just waiting to get my earn out and everything. He said, but I have good News. I have two EAs. I said, why do you need two EAs? He said, well, one does my scheduling and all that. Another one clicks the button in the systems that I need to do to approve vacation and to approve expenses. He's like, so I have one who does just the button pressing for them and then the other one, I mean that's a you Know, and he said, you can't get any, like, literally to do anything in this company. It takes forever. You know, somehow those companies are still, in that case, you know, still big, still scaling, still. But it's just so many founders, I think, founders, CEOs, like, you go and build this company and then you go into the behemoth, whatever the behemoth is, and you just. You're like, is this how business is done? Like, this is. This is crazy. That's. At least that's what I hear from people.

You know, some of that goes with being a big company. And, you know, my experience with people at small companies is a lot of them can't tolerate that. You know, I became interested in the question of how do you build a big company that doesn't. That has a certain amount of structure, but not too much structure. And that became to me a very interesting management question of how do you do that? Because, you know, I used to say, like I said, I saw U.S. robotics, which was the opposite, had like, no structure, no clarity on things, no clarity on roles. I mean, I remember one of my favorite USR stories is we needed a modem for the Palm Pilot. We wanted to put a modem in it. And we're owned by the number one modem company in the world, so. So this is logical. They should make us the modem. So we go to the division that makes the smaller size modems and say, you know, will you make me this modem? And they're like, okay, you know, how. How are you going to pay us for that? And I'm like, well, we have to have some sort of a transfer pricing mechanism or something where we pay you. And they're like, okay. And I go to my boss and I say, we need to put transfer pricing in place so we can pay them. He says, well, we're not going to do that. And I said, why not? We said, well, that's a big company thing. We're not doing big company things here. Yeah, but those guys are actually. They do need to get paid for developing as well as selling it to us. I fully expect to pay them for it, so we should do that. And he's like, we're not doing that here. You know, they should do it because it's the right thing to do. So they wouldn't do it. And I couldn't get them to do it, and I was refused. So I ended up buying a modem from outside the company.

What?

Yeah, Seriously. So, you know, there. A little structure would have helped. So, you know, how do you find the right balance of enough structure but not too much structure? That is a challenge and I think it's an interesting challenge personally, and it's one that I was, as my companies grew, that I was constantly trying to work on what is enough structure but not too much structure.

Now when you, when you went, you started Handspring, what if any changes did you make from Palm, like specific, like deliberate things where you said we're going to do this thing differently?

Well, the number one thing when we started Handspring was it was becoming very clear that these things needed to be communications devices. So already right at the very beginning, I think our employee number seven or eight was a GSM X, which none of us had any expertise in communications at that time. And so that became the product focus of how do we start envisioning these things as communicating devices? And mind you, this is when the networks are very immature. You didn't have data networks like today. You had kind of an SMS style thing with little bursts, but you didn't have full data channels. And so things were quite immature at an infrastructure level. But the cell phone business had been exploding, Nokia and so on. And so clearly seeing that these things were going to be coming together again was part of Jeff's genius to say that's where we need to focus from a technology perspective. And the biggest, one of the biggest disagreements I'd had at Palm when we are part of 3Com strategically, was they wanted us to license the operating system of Palm, the Palm os. And we did not want to license the os. We saw it as a highly integrated device. The OS was highly integrated with the apps, was highly integrated with the hardware. It was one product. And they felt this was Apple thinking and they wanted to be Microsoft, not Apple. Now remember at the time Apple was failing, it's hard to remember this. And you know, Microsoft was winning. So they're like, that's the losing strategy, so you need to license to everybody else. And we didn't think that made any sense at all. We had this, this argument went on and on and finally when we left, I said, okay, well we'll take one of those licenses if you think that's such a good idea, so license the Palm OS to us. And that gave us an ability to get going fast and letting us focus on communications rather than trying to rebuild that whole part of the architecture, which didn't really sense to us to rebuild. So I spent the first, you know, six months negotiating a license.

Wow.

With my. For the guy who used to work for Me in business development. And then we took 30% of the market from them super fast. And then they stopped licensing. It was pretty fun. Then they decided it wasn't such a good idea. So that was sort of how we put together the early hands and we got to market in, I think, I don't know, a year or 18 months with a basic. The first visor, the first handheld device without communications. But the big deal was a slot. We put in a slot with the idea that we could plug in communications devices. And that was the whole idea, was that we could learn more about communications and we could plug in a GSM device or a CDMA device. So the fact that one of those people who sent me those emails that first day of saying with you was the guy who wrote the whole Palm OS helped us enormously in being able to work so quickly here, because we knew the Palm os, so he could design a slot strategy that fit in with the Palm os and we shipped that product very, very quickly.

Wow. I mean, I could probably ask you stories for like many hours because this, I. I'm literally, for me, this is very. I could listen to this for forever. There's so many lessons in everything you're saying. There's so many lessons and so relevant. I mean, it's just running a business is running a business. You know, it kind of like these stories. What I ask every guest this question. What. What is the biggest challenge you've ever faced across all the companies you've been part of in your career? What is the biggest challenge you ever face? And. And were you able to overcome that? If. If you did? How?

Well, I would say my biggest mistake was at Handspring when I did a lease for some massive new buildings in Sunnyvale. At the time, we were the fastest growing company in American business history. We were growing that Fast. We did $100 million in our, I don't know, six quarter of doing business, quarter, not year. So it was an absolute rocket ship. We were growing like crazy, hiring people like crazy. And we needed space. And I had been through the space wars at Apple, where we never had enough space when we were growing quickly. I'd been through hypergrowth before, so I was very familiar with it and I wanted to get us that space. And so I, I took a lease for these two new buildings with the idea that I would go in one, I would sublease the other one. It was really much more than we needed until the point at which we needed it. Then we would have a campus, we would be set for the Future, man. I was thinking far ahead, we would be set for the future. What I neglected to notice was that the environment was changing and that we were, like on the cusp of a major market crash and recession. And suddenly we ended up with a massive problem, which is that the recession hit, sales slowed. Palm had a lot of inventory. They started dumping it. We started having a price war with Palm. We had to. I resisted for a long time, cutting our prices because I said, I don't want to go there. It's not good for either company. But then I started getting inventory problems and I had to meet them. And so it ended up really, really making the company struggle. And then I had. If I didn't have this big debt on our hands, I could have survived that. But. But I had this enormous debt and I had to get out of it. So it was an awful, awful time. It was the worst time. I mean, I was riding the biggest rocket ship and the most amazing experience ever. And then I was, you know, really in the dumps because I had to get out of this lease. Good old Bruce Dunleavy, same guy as earlier, called me and he said, the only way to get out of a lease is to declare bankruptcy. You're going to have to prepare a bankruptcy filing. And I just couldn't believe it. I couldn't believe that I was going from the fastest growth company in American business history to this door of bankruptcy here in the space of months. How could this be possible? But I had to do it. And I hired bankruptcy counsel and I steered a. You know, figured out how to get a bankruptcy petition going, which was the only way to put leverage on the landlord to negotiate out of the deal. Because what a landlord gets is 15% of the value of the lease in bankruptcy. So you can negotiate to roughly 15% or you can pull the trigger, and that's all they get. So in the end of the day, we settled. We gave them a big payment. It was after we'd gone public, so they got most of cash from our public offering to get out of that lease. And then we were really in. You know, we were really weak financially at that point, and it was very difficult to recover from that. So that was just a huge mistake.

So I think when you share that story, you know, I think there's a lot of AI companies today that are the fastest growing companies of all time. You know, 0 to 100 million in two days. I'm exaggerating, but, you know, in. In a. And they're raising money that's never been, you Know, amounts of money that's never been seen before and they're spending money as if, you know, it's, it's unlimited. Is there something you learned from that lesson that you would share with those who have built amazing companies, amazing products and all that stuff? But, you know, I would argue that we're maybe in a bubble, you know, it's to some degree, you know, is there something you learned from that that you would share with the next generation?

Well, I think one always has to do some downside planning and have some, you know, somebody around the table who's arguing, but what if, what if the economy collapses? What if this happens? What if that happens? What is our backup? What is our. Do some scenario planning? I once heard Meg Whitman, the former CEO of Hewlett Packard, speak, and she talked about when she did, I think it was acquisitions or something, she would have a white hat and a black hat where somebody was appointed specifically to argue the opposite side of a trial.

Love that, Love that.

Why we shouldn't do it. Even if they didn't believe that they were. It was like being a defense attorney and a prosecuting attorney. You have to have somebody playing that role, arguing what's the worst that can happen here? What's the downside? And forcing people to think about that. Now, would that have changed my view if I'd done a better job of downside planning? I don't know. I don't know if it would have. Remember again, fastest growth company in American business history. $100 million. Real product sales to real customers. These.

Right, right, right.

These were real customers. So I'm not sure how much it would have changed my mind, but maybe I would have done if I'd done one of those buildings rather than two of those buildings that might have made a big difference. So, you know, I think certainly that having, making sure that somebody on the team is trying to push worst case scenarios to make people think about it is a very, would be a very good practice that I would advise.

What is your view right now on this macro on the market, on AI? Do you think you've seen all the shifts you just mentioned at the very beginning? You've seen all these shifts? Is this the biggest shift ever? Is this the biggest technological advancement that we've seen in our lifetimes will ever see? Like, well, not maybe we'll ever see, but at least up to this point, like, how, how do you feel about how the market is talking about AI?

I don't agree. It's the biggest shift ever. I feel like it Is a big shift for sure. But boy, look at these shifts I've lived through. I mean, going from no computing to desktop computing. I lived through that one. I mean, that's pretty amazing. I know a lot of your younger people won't realize this or remember it, but there was a time when you didn't have access to to computing at all. Pretty big shift. Going from desktop computing to handheld computing. Pretty big shift. You know, we have these things on us all the time. We can't imagine a life without them. There was a life without them. That changed everything. Everything. Getting them communicating, that changed everything. The Internet, I mean, we didn't have an Internet before. I remember the day that one of the guys on my team showed me the Internet And I bought Palm.com the same day because I got it. I was like, wow, this is going to be huge. Everybody's going to be on this. The Internet is easily one of the most major transitions in our lives in the whole world of what has happened. When you think about how it's impacted communications, how it's in entertainment, how it's in politics, it's just hard to say something it hasn't impacted. So, you know, I don't see how you could take what's going on in AI and say it's vastly more than these massive changes that have happened on our industry. I think it is faster. I mean, these other changes took place over some periods of time. But you know, a lot of this transition with AI, it seems fast now. Now mind you, I've been working in AI for 20 years, so it doesn't seem so fast to me, but it seems it is. The acceleration has happened very fast. You know, in terms of. Is there a bubble? Isn't there a bubble? I'm not sure I know anything better than anybody else, but I started to think about it myself in sort of two different layers. One layer of it is the LLM based models and the battle going on between perplexity and ChatGPT and Gemini and blah blah, blah. And that is where those big bucks and that big investment and everything is going in a lot, to a great extent. And the data centers and the blah blah, blah, blah, blah. I feel like that is a bubble and that is partly because it's a race. Everybody knows it's a race. There's going to be a couple of main models that survive. We saw this with the Internet. You know, we had Yahoo, we had aol, we had Google, you know, we had. And it ended up settling to a few. And a lot of Them went by the wayside. I believe that'll happen with these LLMs, and I believe they believe it'll happen, and that's why they're investing so much to win that race. The second layer is the apps that are going to build on top of those. And I'm kind of less concerned about that as a bubble. I do think there will be a lot of AI interesting capabilities that will be built into applications. And I know there's ten thousands, tens of thousands of companies there, so there'll be a shakeout, but each one of those is not a massive capital investment. They're much lower investments than at the layer down. So, you know, and there'll be some winners. There'll be legal AI company, they'll be a nursing AI company, they'll be whatever. They'll be a bunch of winners with a bunch of verticals along there and almost on a feature level, rather than a sort of a new app level, but incorporating features. So I've started to look at it as these two very distinct layers with very different dynamics.

I really like the way you put that. I agree with all of that. I think at the application level, the only thing is that I think those companies, there's a similar race going on in some of those big categories and people are putting, you know, billions of dollars to work, which is, which is a lot, you know, and of course for the winner, then it's not going to be a lot because they're going to be the standard. But for the 15 other people or 20 or 100 other people, you know. But thank you for that. I want to transition. I want to be respectful of your time. So again, I could do this for hours. I want to transition to your own personal background and talk a little bit more about your background. Where, where are you from originally?

I was born in Cleveland, but I grew up in Benton Harbor, Michigan.

Okay, and did you kind of growing up, did you have some exposure somewhere in your life that you knew one day you're going to be a CEO of a company, a founder? Like, did you, did you have that exposure somewhere and is that in your DNA or was that something later?

Well, my dad was a business person and I, you know, loved hearing about it, you know, going to his plant, he worked in an aluminum smelting plant. So real hard and hard industry, not consumer products. And I remember finding it fascinating. I literally remember those, you know, visits as a small kid. So I think I was, you know, interested in it, but I wouldn't say it was as well formed a Thought as saying, I'm going to be a CEO one day. In fact, you know, I think I kind of always assumed that I would become a lawyer because that was what, you know, people did who had sort of an intellectual bent at the time. So I thought I would become a lawyer. I went to Yale, I studied history, and then I went to. I really didn't know if I wanted to do that or not. I felt like I just didn't know enough about the world in general. So I decided to go to work first. And my first job was at a bank. And I just fell in love with the business world. And that was it. I'm like, I'm not going to law school. I was bossing around lawyers at the age of 21, with no experience. I was asking him to draw contracts for me for these deals. And I said, well, I like this side better than that side. So that was when I decided to not be a lawyer, but to go into business. And I worked with entrepreneurs. I was at the bank. I ended up in this group called Regulated Industries, where my focus was cable television, which was just starting at the time. They were just stringing the first cables. And so I was a part of a growing industry with amazing entrepreneurs building these things from nothing. And that was when I really got the entrepreneurial bug. And I just totally fell in love with the idea of creating something and. And building something new. What.

What was the biggest break in your career? Was there, like a moment in time in your career you can go back to and say, that was like the moment. Like that. That was my big break?

Well, I. It's funny how you. I'd have several different answers to that. I mean, probably the biggest general break in my career, and then maybe I'll talk about a specific thing of an insight. But my biggest general break was just I had great bosses one after another. I mean, this boss I had at the bank, Bob Murray, he gave me incredible opportunities. For a kid out of college with zero experience experience, you know, presenting to executives, taking on accounts, calling on them. I mean, the guy was just amazing. When I got to Apple, Roy Weaver was an incredible mentor to me. Then Bill Campbell was a mentor to me. And I mean, one after the other, I've had phenomenal bosses who've given me tremendous opportunities to learn to make mistakes, supported me. And, I mean, that's kind of my biggest general break. I think I've experienced experience, and I tell a lot of people when they're looking at their first jobs, I tell young people, you know, pick your Boss. Well, you know, you think they're picking you, but you want to make sure you're working for a great boss because that is going to make the biggest difference in your career as anything working for a great boss. So think hard about that. In terms of insight, I would say that the biggest insight that I had that changed my career was when I was in business school at Harvard and I took this basic IT class and they had some visitors and in walked Dan Bricklin and Bob Frankston who had created VisiCalc, which was the first spreadsheet. It was on an Apple 2 48K. You've seen pictures of it with the little display, eight column display, very rudimentary at the time. And I saw VisicalCity and that like rocked my world, changed my life because I'd done those spreadsheets by hand as a banker over and over and over and presenting a loan committee and doing all sorts of things. And I was like, I got it in that instant that this was going to be a huge industry and that's what got me in the computer industry. I had no computer background, I had no technical background, but I saw that demo and I said I, I've lived through cable TV as a big girl. That gave me tremendous opportunities. I was the youngest promoted officer in the history of the bank. And it was because I was doing these DE deals and they were interesting and profitable. This is the next cable TV personal computing. It's going to be on everybody's desk. Everybody's going to have one of these things and I just sort of got it. And that was when I went into the industry.

The, the, the call out of the boss. In all, you know, I've interviewed, I don't know, 80 something CEOs so far. When I asked people about this, breaking this, this, this, this moment in their career that gave him that big break. It always comes, not always, but most of the time comes down to the boss that they usually mention this person. Usually it's something to the effect of this person let me punch above my weight or let me do something I probably should not have been allowed to do. And almost everyone has some story like that of that, that was the catalyst, you know, like, and they're like, I don't know why they chose me to do that, but they gave me that job or they gave me the opportunity to do that and that kind of accelerated my career or let me, you know, see that I was, I could do that. And so when you say that I, it's good advice actually. No one has said that specifically. Like, think about the boss you're choosing, but the other side, when you ask them their big break, it comes down to their boss.

Yeah, well, and then you think about how you do that for other people. And so when you're in an organization and leading it, then you start thinking about yourself, okay, where's the next Donna Dubinskis? Where's the people who have this sort of talent, this sort of capacity? How do I enable that capacity? What experiences do I give them? How do I move them through the organization? You start becoming very conscious of the need to do that within your own organization.

What is it at the core? Look at your real core. What is it that drives you? I mean, you've been through all these companies, ups, downs, everything kept going, kept driving. What is it deep down that drives you, that motivates you?

I don't know. I mean, I guess some of it is inherent in you. I mean, I, I've, I've often wondered that. Was it, you know, seeing Steve Jobs early and getting inspired by bicycles for the mind and changing the world and, you know, he talked a lot about that sort of stuff and, but you know, I was one of those people who was, you know, setting up lemonade stands. So, you know, I was having this mindset very early on, long before that as well. So I think for me, the through line is been impact. I like having impact. I like doing things that make change in the world. I mean, Steve Jobs used to say, make a dent in the universe. And, you know, I feel like I've tried to make a debt to the universe. I, I, I like to do things that matter and you know, one after the other, I've been a part of things that mattered and that's been important to me.

So you've spent time, you know, kind of post running companies. You've done a variety of other things, been on boards. You know, you mentioned, I mentioned the Yale board that you were on. Is, is this what you're spending your time like to make an impact is you're kind of doing. This is a variety of things. You know, a public company, technology company board, then a school. You've done some stuff in the government, like you've done a variety of things. Is this where you're spending your energy now?

Yeah, I mean, I'm spending my energy on a lot of those things, you know, right now, sort of reassessing and thinking about some new projects I might do. So we'll see. I'm 70, so I have to be, you know, reasonable about what I can and can't do. But I should talk for a minute about this government service, because I do think that's really important. Back in 2022, I think it was, I actually joined the federal government working for Secretary of Commerce Gina Raimondo. She asked me to come to Washington to be the first person to implement the CHIPS Act. She had people on her team who were doing the legislation, which I would have definitely not been qualified to work on. But she had nobody on her team prepared to implement it if it passed. It hadn't passed yet. And she said, would you come for six months and work on this because you're an implementer and you know how to do it? And I got very excited about that because I just felt like I was incredibly privileged to be a part of this great nation. I feel that every day. It just was amazing to be born in this time and place with the opportunities I've had, and I don't give myself so many pats on the back. I think a lot of that was the good luck of my grandfather getting on a boat and coming here and, you know, at the turn of the last century. And so I've had these enormous opportunities, and I've never served in any way. So when she asked me essentially to serve, I said, yes, I'm going to do that. I'm going to take and apply what I know and serve my nation. So I rented an apartment in Washington and I went to Washington and I worked in the Commerce Building and, you know, to and from my little apartment in Washington every day. And spent. I spent almost a year, not quite a year, working on getting ready to establish the CHIPS act, establish the implementation of the CHIPS Act. It did pass. While I was there, I got to go to the White House for the signing ceremony and the East Wing. Yeah. And managed to, you know, be a part of something like that, which was exhilarating. And then I. There were sort of two parts of the Act. One part was to build fabs. You've all read about that, 39 billion to help build fabs in the U.S. and then there was the R&D part, 11 billion. So I spent the first, more or less year working on getting ready to implement the first part. We hired a team. I transitioned it all over to that team. They did an excellent job of implementing that program. And then I spent. Turned my attention to the R and D part, which was always even more interesting to me, and how to structure the R and D program envisioned by Congress. So I have spent the last couple of years then since then, I ended up leaving the government and being on a nonprofit board that was implementing part of the act. And that's how I've spent a lot of my time in the last few years, is what. What I view to be national service. Wow.

And. And, you know, I like the. The story about Yale, you know, you mentioned to me. Story about Yale and kind of your grandfather, you know, could you maybe share that. That story?

Yeah, sure. I mean, my grandfather came to this country, you know, and I don't know, maybe 1908 or something, as a child, and with nothing, you know, I found the records in the Ellis island records, and this family was, you know, poor as could be, and he actually worked and lived near New Haven. He sold advertising for the local Jewish newspaper. And he used to, you know, peer in through the gates of Yale as this, like, amazing place. And never imagined that, you know, a grandchild of his, let alone a granddaughter, because, of course, it was all male at the time, could possibly go to a place like Yale. And so when I got into Yale and decided to go to Yale, you know, my grandfather was still alive, and he was quite overcome with what an incredible thing. And it's a lot of what gave me this feeling of wow, you know, what. What other country and what other time in human history could we have gone in the space of two generations from arriving penniless at Ellis island to being at a place like Yale? And then when I got on the board of Yale, I thought, oh, my gosh, if only my grandfather had lived to see this. And then when I got appointed senior trustee, which is like the equivalent of board chair at Yale, I mean, to be bored. Chair at Yale, coming from that, it was really an overwhelming feeling to say, look how. What the incredible opportunities I've had.

It is amazing. I mean, you and I talk about this, like, even in my personal life, and my dad coming to the country with nothing, and, you know, again, one generation, two generations, what can change is literally crazy. I mean, it's really not that much time, you know, and to completely change entire tree of a family, you know, that's been around for however long, and. And it's amazing. I love that story. So thank you for. For sharing that. Okay, last question. For you. Knowing everything, you know, today and all the experiences you've been through and everything, what is the one piece of advice that you would go back and give yourself before you started your first job at the bank? You know, what. What would be the one piece of advice you go back and give yourself?

I think I would just tell people or tell myself to, you know, treat everybody with respect. And you just never know when people are going to come around again and it's just the right thing to do. And even if things are not going well, you have to terminate somebody or you have to do a layoff or you have to change direction. It just. Just do it with dignity, you know, respect for the person, the individual. I mean, I just think treating everybody respect. When everybody said how much they love working for my companies, when I tried to figure out why was that, I didn't feel like I was doing anything magical. I think it really came down to that, was that I just. Just really believed that every person who was there was doing something of value for the company. Otherwise, it shouldn't be there. But, you know, even the receptionist, I'd know her name. I'd go in, you know, how you doing today? What's going on? What do you see? You know, what's your opinion on things? And I think just that very simple idea of listening to people, treating them with respect is just so foundational because that's. That's what makes a good life.

Donna, thank you so much for doing this with me. There was so many, so much gold in this conversation. Thank you very much for doing this with me, and I really appreciate it.

My pleasure. It's great that you do this. I think people can learn a lot from it, and I'm very happy to share my story.

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