Deep Dive with Laura Mather

Intro: Welcome to The Daily Bolster. Each day we welcome transformational executives to share their real- world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I'm here today with Laura Mather. Laura is a multi- time founder. She has founded companies in cybersecurity and in HR, two really different spaces. She has raised a bunch of money in the valley in venture funding. She is an expert in pitch decks, in board messaging, and working with analysts. She's now an independent director and advisor to startups. Laura, it's great to see you.

Laura Mather: Really great to be here. Thanks so much for having me.

Matt Blumberg: Yeah, so for the Friday interviews, we always walk through someone's career and just talk about the journey that they've had and things that they've learned along the way. One of the things that's interesting for me: occasionally sometimes I will interview someone and I've known them for their whole career, and sometimes that's not the case. So I have to do a prep and back research, which I had to do here. Because you and I met, I want to say something like 2012,'10, '11.

Laura Mather: I was going to say 2011. Yeah.

Matt Blumberg: Yeah. And we were introduced by a common board member, Scott Weiss, one of the all- time great, great board members that I ever worked with. So I know you from that point forward, but didn't know the backstory. So I would love to start at the NSA, the National Security Agency: not a place that you usually see a founder on their LinkedIn profile. But I think it was your first professional job was as a mathematics researcher for the NSA. So I'd love to hear a couple minutes about that.

Laura Mather: Yeah, that was a super- interesting moment in my life. What happened, I was in undergrad. I was applying to grad school and I found various fellowships. And I applied for a specific one that was for essentially minorities in science: minorities being women in science, one class of minorities in science. And I applied for it, and it was sponsored by IBM. I thought, " Cool, maybe I could go work for IBM." It turned out in that year; it was 1994; IBM was not offering any fellowships that year. But another organization was, and it was the National Security Agency. So the fellowship people came to me and said, " You didn't apply for the NSA one, but would you be willing to consider it?" And if anyone remembers the NSA in 1994, you won't, because they weren't even allowed to say NSA. They weren't allowed to say they worked for the National Security Agency. So I had no idea what this government entity was. And I said, " I don't know. I don't know if I want to do this." They got me on the phone with someone from NSA, and we had a six- hour phone call where he was trying to tell me what they did without really saying it. And I wasn't-

Matt Blumberg: Of course, an actual phone call.

Laura Mather: Yes, exactly.

Matt Blumberg: Not an iPhone, not a Zoom.

Laura Mather: An actual phone call, with a little curlicue line and everything. I struggled, because I was in Boulder at the time. And Boulder, as you know, is very liberal. And this was this thing of, " Do I feel like I could go work for this spy agency?" And I talked to a bunch of people. In the end, what I realized was I very much believe in democracy, lowercase d democracy, and we elect our government. A lot of times I vote for someone who doesn't even get elected. And I still elected the government because I participated. That's the way I look at it. And the job of the NSA is to provide as much information for our government so that they can make the very best decisions possible. You only make good decisions with as much information as possible. So I decided, " You know? I'm okay doing this." And I lost one friend over it. There was one friend who said, " If you go work there, I will not speak with you."

Matt Blumberg: Wow.

Laura Mather: And this was Boulder, right? People-

Matt Blumberg: I know, but this was a while ago. I mean, that sounds very 2023.

Laura Mather: Yeah, no, no. Oh yeah.

Matt Blumberg: Wow.

Laura Mather: No, he said he wouldn't speak with me anymore. And so I lost one friend over it. But I went there. I did two summers. What happened at the end of my second summer is I was studying essentially machine learning, natural language processing. These large language models; that's what I was doing back in'94, believe it or not. And I was there for my second summer. And my boss at the time said, " Look, we have a ton of cryptographers and we do lots of code breaking. But we don't know how to retrieve information out of our databases. That's the one thing we're really missing. So will you come finish your PhD here at NSA to bolster our abilities to do search engine technology? And we will pay you to do your PhD." So that's what happened, is I finished my PhD in Maryland. I had a Maryland person on my Dissertation Committee, and then I had the whole Boulder group. I would fly back and forth, and the rest is history. And I did search engine stuff for NSA back up until about 2000.

Matt Blumberg: Fascinating.

Laura Mather: It was pretty fun. It was super- interesting, all kinds of... I don't know... interesting things where you have to take lie detector tests. And the FBI goes and talks to all your neighbors where you grew up, and things that most people, I think, don't experience.

Matt Blumberg: So now your first startup in cybersecurity starts to make a little more sense, but we will get there in a minute. We have a couple steps between here and there. So your next role was at Encyclopedia Britannica as head of R& D. So how did you get from the NSA to Encyclopedia Britannica? And what did you bring from the NSA? Obviously you didn't take anything, or they would've cut your fingers off. But what was the lesson you took with you from A to B?

Laura Mather: Yeah, what happened at NSA, like I said, they didn't have people who were doing search engine technology. And in the end, that was to my detriment. They told me, " You're basically not going to get promoted if you don't do cryptography. We only have promotion classes for cryptography. And because we don't know who you are." It was like, " You break our brains." So I decided if I wanted my career to actually go forward, I probably needed to leave the NSA; and it bummed me out. With 9/ 11, the big thing they said is, " We had the intelligence. We just didn't know how to find it." But that's water under the bridge. In'99, when I was thinking of leaving, man, I wanted to get into the dot- com boom somehow. I'm sitting in Silicon Valley now, but I applied to a ton of places out here. I was offered a job at Infoseek. You might remember them.

Matt Blumberg: Oh, yeah. Yeah

Laura Mather: I looked at a bunch of places, and I applied to Britannica. com: not to the Encyclopedia Britannica, but to Britannica. com. It's a little bit of a long story of why I didn't take the job at Infoseek, but I ended up at Britannica. com. Unfortunately it was in San Diego, so I didn't make it to Silicon Valley, but it felt like a dot- com thing. They had a Super Bowl ad that year. In 2000, they actually paid the$ 2 million to have a Super Bowl ad. So that's sexy, right? Or something. And the big lesson I took from NSA: mostly it's really hard for me to work for the government. I would say the culture of the government is about 179 degrees off of the culture of Silicon Valley. It's just there's no urgency. I had an office mate who slept all day, because they couldn't fire him because he knew state secrets. And there was one of those in every group that I went to, and that just drove me insane. I would look at this guy and go, " One one- millionth of a penny of my taxes went to your salary today." It just drove me insane. So I just wanted to work somewhere that had urgency, that had impact. And Encyclopedia Britannica felt like that, right? It's Encyclopedia Britannica. You can influence the educational minds of tens of millions of people every day! It was amazing for me.

Matt Blumberg: Yeah. And what were the years you were there?

Laura Mather: I was there 2000 to 2002.

Matt Blumberg: It's so funny to think about. I don't even know if that exists anymore. Or I think it does, but they stopped printing the books, right?

Laura Mather: Yeah. They don't print the books.

Matt Blumberg: inaudible

Laura Mather: They stopped printing the books a while ago.

Matt Blumberg: You think like Google, " Our mission is to organize the world's information." That used to be the world's information, whereas much as could be publicly transmitted. We had two sets of them in my house, one that my dad got for his Bar Mitzvah in 1953 or something, and the one that I got. And it's just so interesting that, I mean, that whole business was just turned on its head overnight by the internet, as was the case with many businesses. So I wonder if you have; this is a random question, but it's related. I wonder if you have a perspective on the accuracy of Wikipedia and the things like Wikipedia relative to Britannica. I think there's actual data on this.

Laura Mather: Yeah.

Matt Blumberg: But I think schools... I have three kids who are teenagers, and you have one that's close... Schools really struggle with policies around online sources, and even Wikipedia.

Laura Mather: Yeah. It's funny, because I was still publishing papers. And that time I was still a researcher, and Britannica wanted me to be publishing. So I was publishing papers in that time, and of course I would cite Britannica, but Britannica doesn't have the newest stuff. There was nothing on large language models in the encyclopedia. And yet Wikipedia had a page on that, because some expert on large language models did a page on it. So I was even citing Wikipedia in my work, and I got dinged for it. The reviewers were not happy about Wikipedia. But other than other papers, there wasn't much else to cite. But I do think that there's a lot of really great research now that crowdsourcing information is hugely effective. And especially some of the things Wikipedia has put in place as far as making people moderators: there was a really interesting article about the way that they give certain people power versus not. And they've done it really well, actually. At least that's my experience, is it's pretty good. I'm sure everyone has a story of the one thing that went totally sideways. But usually they're pretty good at even reining those in. So I do think Britannica still has a place of the history and almost like unbiased journalism: where you know it's been researched, you know it's been validated. That's an important thing, especially in this age of disinformation and misinformation. And the fact that Wikipedia can be changed even on a whim. And then you're not sure, " Did this one just get added?" I don't look at what just got added. Right?

Matt Blumberg: Right. And did someone police it? Yeah.

Laura Mather: Exactly. So I think both have a place, for sure. And who knows how Britannica's business model is going to do. I think they're struggling, but some things definitely need to be re- innovated. But at the same time, it's a little sad when some of these things that clearly had an amazing part of our history maybe aren't quite as relevant.

Matt Blumberg: Yeah. All right, so you leave Britannica. Why don't we talk about the next two roles together? Because I have a feeling they had more in common than the ones before and the ones after. You were Director of Trust and Safety for eBay, and then you went to work at MarkMonitor. So talk about that, that sort of combined chapter.

Laura Mather: The eBay one was super- interesting. I was at Britannica in San Diego. They ended up moving me to their offices in Chicago. So I was now at the mothership, and that was great. I loved living in Chicago, having the opportunity to live in a big city. But then I really wanted to get back into Silicon Valley and the dot- com stuff. This was 2002, which was the downturn, the bust; things were not good. So it was a hard time to find a job in Silicon Valley. eBay was one of the only places that was still growing and was hiring. So I applied for three different roles at eBay. They brought me out I think twice, and they offered me all three roles. One was in the Research Group, one was in a Policy Group, and then one was in the Trust and Safety Group. And the thing about the Trust and Safety Group was online crime was just sort of getting going. The criminals had been attacking AOL for a long time, but they were just figuring out that eBay and PayPal were pretty profitable. So they were really starting to turn their focus to eBay and PayPal. And the people in Trust and Safety at eBay said, " We need someone who can fight these criminals, so we need someone who's law enforcement-y and knows online stuff. How many people in the world will do that?" It's like, " Well, me." So they seemed to think that that was the right combination, which worked out great for me. That was the one I took because it just seemed so cutting- edge, so interesting. And you really had to forge your own path. That got me really excited, so went and did that for eBay. My main job was fighting phishing for both eBay and PayPal, because they were the one company at the time. And then when I left, MarkMonitor was doing phishing fighting. So I went and did a bunch for them too, which was fun and awesome. But it was this strange thing where my career really like... NSA, Britannica. But it just lines up to go to do Trust and Safety at eBay. Holy cow, am I lucky that that's how it happened?

Matt Blumberg: Yeah, it's interesting. I do these every Friday, the arc of someone's career. And what I'm really curious about the Taal Vista experience, which I actually don't know very much about. But we'll get there. But it's really easy in the rear- view mirror to say, " Oh, I understand how someone got from there to there, to there; that all makes sense." But when it's in the windshield, you have no idea.

Laura Mather: Yeah. Yeah. And it was so scary. I actually quit Britannica a year before I went to eBay. I decided to take a year off and work on some personal stuff. That was terrifying, because it was during the bust and nobody was hiring. And yet looking back, I go, " Man, I was so stressed that whole year. Am I ever going to make another dollar in my whole life?" Yet it was totally fine and awesome, and I shouldn't have been worried at all.

Matt Blumberg: Let's talk about Silver Tail. What was the business? Where'd the idea come from? How did it go?

Laura Mather: Yeah, Silver Tail was our cybersecurity company. My husband and I started it together. He worked with me at eBay before we were dating or any of that. And what happened was when we were fighting phishing and online criminals at eBay, the Anti- Phishing Working Group had these stats where they would track all the phishing emails they knew about, and what brands were being targeted. When I was at eBay, 85% of all phishing emails targeted either eBay or PayPal. So I was fighting 85% of all the criminals. As usually happens, we got pretty good at fighting. You didn't even have to be all good. If you could just be a little better than the other guy, then they would just go target the other guy. So we would get better at fighting them, and they would start to diversify. They would go after Sears or Lenovo or Citibank or whoever, because they didn't have people who had law enforcement and online experience. So the criminals started to diversify. When I went to MarkMonitor, I think at that point, eBay and PayPal were something like 18% of the targets of all the phishing sites. My husband and I, at the time we were dating and we were looking at this going, " We know how to fight these folks, and these brands need help. They need a lot of help." By the way, at eBay we could never build exactly the tool we wanted, because we were fighting with marketing folks for blah- blah. But we knew the tool we wanted to build, and we said, " Why don't we just go build that tool we wanted to build, and sell it to all these brands that are being targeted now?" We were able to pull some people out of eBay, some engineers, we pulled a couple of engineers out of Google. Some of the eBay people had gone to Google, so we pulled them. They knew how to build systems that could process lots and lots of data. At the time, E- Trade Market Open was the highest traffic that any internet site saw. And then E- Trade Market Close was the second- highest traffic that any website saw. And our system was able to process E- Trade Market Open and E- Trade Market Close after many iterations. Not the first time, but after many iterations.

Matt Blumberg: Right.

Laura Mather: So what we could do is we could look at all the traffic across a website, and we could detect when there was some new interesting behavior happening, which is what the criminals are always doing. They're always probing. " Can I put something in the cart and not check out? And later put a coupon in, and get it to where I have so many coupons that my laptop is negative$ 20?" They would figure stuff like this out. And that's not what normal people do. So we would just be looking at, " Are there flows on a website that look anomalous?" And we could identify those. We love to have these meetings where we would get the traffic for a website, we would present it to people. And every once in a while; actually, in a lot of our meetings; we'd say, " And then this is happening." And someone in the room would go, " Oh, shit!" And they'd get up and they'd run out of the room; it was like, " We've got to go shut this down. It's like, " We'd probably get a sale out of this one." So those were the types of moments we were always looking for. And to our benefit, the criminals were happy to target anyone who they thought they could use to make money, and we could go protect those people. That was pretty amazing.

Matt Blumberg: Yeah. And how did the business do? I know you had the great exit to EMC. How big did the business get along the way?

Laura Mather: Yeah, we got to about 20 million ARR. Not stellar, but as you know, going from zero to 1 million is like-

Matt Blumberg: Zero to 1's the hardest.

Laura Mather: 1 to 5 is the next- hardest.

Matt Blumberg: Yep.

Laura Mather: And then after that it gets a little easier. Though each stage of that is a very different company also, as you know. And so those were the big lessons was the zero to 1 million is a very different company even than the 1 to 5 million company. But we did well. We had lots of banks as customers, we had lots of e- commerce. I think it gave people comfort: the fact that we had already fought these same criminals. And we knew what to look for, because they didn't. Again, there were so few of us in the world who had done this cybersecurity thing, that the fact that these brands could outsource it to us made them really trust us.

Matt Blumberg: Yeah. All right. So I want to ask one question about Silver Tail, which you probably get a lot. There are a lot of questions I could ask you, but I'm going to ask one just because I haven't had anyone on The Daily Bolster yet where I could ask this. What was it like starting and running a business with your husband?

Laura Mather: Ah! Yes, we are weird because it's fantastic. I talked about how I like impact and I like urgency. And when you're running a business with your husband, you literally can work 24/7. You're making dinner and you're talking about the board deck. Or driving the kid to preschool and you're strategizing how you're going to interview this salesperson who's coming today. And for us, we loved it. There's definitely downsides, too. I mean-

Matt Blumberg: There are downsides to working 24 hours a day, for sure.

Laura Mather: There's downsides, for sure. And we struggled a lot with that. We ended up having to make the rule that Thursday from 7: 00 P. M. on and Sunday from 4: 00 P. M. on, we were not allowed to talk about Silver Tail. But we literally were working 80, 100- hour weeks, which was good and is what we needed. But we love working together. We are so complementary. We're very aware of how complementary we are. As an example, I'm not the one who's going to take the team out to lunch once a week. That's not my thing. And so I outsource that to him, and he loves doing that. We very much balance each other on those things, and we're really good. I think maybe another thing is neither of us have an ego. When I'm not good at something, he can tell me and I can be like, " Ah, crap. You're right. You should do that, and vice versa." And so it was fantastic.

Matt Blumberg: Well, that is a great story. And I will talk to you about that more offline, too.

Laura Mather: Okay, great.

Matt Blumberg: But let's move to Talent Sonar. I actually don't know much about Talent Sonar. So that was your next startup. Was that with your husband or by yourself? What was it?

Laura Mather: Yeah, I started by-

Matt Blumberg: How did you get from cybersecurity to HR?

Laura Mather: Yeah, it's the usual story: which is, as you know, when you're doing a startup, there's a problem you wish someone had solved for you. And you decide that maybe lots of people will need the problem solved. And that's what happened. When we were hiring for Silver Tail, 1), it was hard to find diverse folks. But it was because we didn't go outside of our network. I realized that later. And I had a very clear memory actually of being at eBay and interviewing a gentleman. I walked into the conference room and this gentleman was somewhat older. He had a gray beard. And my first thought was, " He's not a culture fit." I realized later that was a bunch of crap. I really wanted to address that problem, and I wanted to address it within myself. So I spent a bunch of years after Silver Tail researching why people don't hire diverse teams. Is there science around how you can hire diverse teams? And aha! There's a lot of science on how to do this. That you take the names off of resumes. You make sure that in interviews you ask the same questions to every candidate. It's not hard.

Matt Blumberg: Like the schools; take the schools off.

Laura Mather: Exactly. The schools, or anything else that could be indicative. It's not hard to do. So we exited Silver Tail late 2012. By 2015, I'd actually spent maybe 18 months really digging into this. And early 2015 was when Apple and Google and Intel all said they were going to put tens or hundreds of millions of dollars towards diversity. How often do you hear of a startup where all of these big brands are saying, " We're going to pile tens or hundreds of millions of dollars on this space"? And I thought, " I have nailed the timing of this." That's hilarious now, but I thought I had, right? So it was very much me wanting to solve a problem within myself, hearing that lots of people said it was important, and understanding that there's actual science that solves the problem. You just need to operationalize it. So that's what we decided to do. I raised the money by myself and then Mike joined later with engineering and as the CTO.

Matt Blumberg: How did the business do? Actually, I've never heard of Taal Vista, which was the ultimate acquirer. But how'd the business do and grow? And what was with Taal Vista?

Laura Mather: Unfortunately, we never even made one sale. We got really far with lots of giant brands, because I'm really good at selling into giant brands. And what I learned is... I learned a few things. You shouldn't sell into shame. So if you go and you're selling a diversity product, what people hear is, " I'm biased. And therefore, I need to pay money to deal with my bias." They don't like that. That makes sense. The other thing is these companies were happy to talk a lot about their value of diversity, but they weren't willing to actually do anything about it. Essentially, the hiring managers really wanted to hire people who they felt comfortable with. And that is not what diversity is. Diversity is you actually need to hire people who push you a little bit, who get you out of your comfort zone. And when the HR people went to the hiring managers and said, " We said we want you to hire people who don't look like you and who push you a little bit," the hiring managers would say, " No way. I'm just going to hire my best buddy over here, and that's going to be the best for the company." And then the HR people had no power to say anything different. So it was a failure. Let's just be clear. I feel like it was important to have done it. Because if we hadn't, all these companies could have said, " Oh, we really cared about this. We were going to do stuff." Yet they had the opportunity, and they didn't. So we were able to show that they were willing to talk about it, but they weren't really willing to take the actions that were required. And I look at some of these giant companies who have 27% of their engineers are women, something like that. And if you look at these companies, if they were to say, " All of our hires for 2024 will be women," they would find enough qualified people, these giant companies. Because they could take the cream of the crop. They could easily hire enough. And they could probably get to 45% women if they did that. And yet they're not willing. So let's just be clear: that's fine. But it says a lot about what they actually value.

Matt Blumberg: Yeah, that is so interesting, your thought on the timing. I mean, look, obviously the timing of starting a business has an infinite amount to do with the success of the business. And if you don't believe that, talk to the people who started MySpace or anything that came before Facebook.

Laura Mather: Exactly. Yes. Or anyone who did AI in 2001. Right?

Matt Blumberg: Yeah. Yeah.

Laura Mather: How dare you in 2001 do AI?

Matt Blumberg: Yeah. Yeah. That's super- interesting. So when you think about the comparison of your first lap around the track and your second lap around the track, even though you had very different outcomes, what did you bring into that second startup that you're like, " All right, I've done one. Here's how I'm going to approach it differently"? Did that work? Are those things that you wanted to do? We definitely all do that.

Laura Mather: I do think the thing I had going into the second one was that I had a little credibility to raise money. I'm not sure I could have raised money on the diversity play if I didn't have the credibility behind me. Because VCs didn't believe in the diversity play, and probably they shouldn't have, right? Because we failed. That was probably the right decision. But it did give me the credibility to raise money. The other thing is the culture of a company is so important. And the culture of Silver Tail had started to slip a little bit near the end. I was very clear that I wanted to maintain... My culture is very transparent, it's very positive. It's very anti- political. Again, my husband and I don't have egos, so we should have probably gotten rid of a couple of egos at Silver Tail, that kind of thing. So I really wanted to build the company that I built. Because at Silver Tail we did hire a CEO, and that was by far the best thing we could have done. Zero regrets on that. But I wanted to see what kind of CEO I could be at the later stage. I was CEO for the first couple of years of Silver Tail, but I really wanted to see what kind of CEO I could be when the company started growing. Obviously we never got there, but that was my goal.

Matt Blumberg: Yeah, I think the lesson about culture and making sure the right people are on the bus and moving people off the bus; not just figuring out how to move people onto the bus but move them off the bus; is one that you cannot learn fast enough in your career.

Laura Mather: Absolutely.

Matt Blumberg: Yeah. All right, so last question for you. Now you advise startups and you sit on boards. How do you think about the impact you have as an advisor or a director where you don't get to own the problem? Your hands don't get nearly as dirty as they do when you're an operator. How do you think about that? How do you balance those things out?

Laura Mather: What I've found really interesting, having sat on the other side of the table, having been the executive, having been the founder, is that I really understand what it's like to be in their shoes. With Silver Tail, I had lots of advisors. We were super- fortunate to have really great people, and the most awkward thing was when someone would say, " You really need to do A." And then the next person I talked to would say, " You really need to do B." And the next person would say, " You really need to do C." I felt like I was letting them all down. Because usually I did B, which was some combination of all of them. But it would get awkward. And some people with egos would be offended that I didn't take exactly their advice. So I think it's a place where I have a real benefit when I work with founders and with boards, is that I understand what it's like to hear all of these different opinions. And I'm not offended when someone doesn't take my advice. And I actually want them to go get lots of different data points. I'm all about data. I'm very scientific. " Go get lots of data points and then see which of them mesh with what is in your head." And I'm okay with that. It can be challenging to work with a founder and say, " If you go down this path, here's what's likely to happen." And they go down that path anyway. But we know that sometimes we just have to learn the lesson ourselves, and I get that. So I think that that really set me up well to have a lot of patience, to feel like just because they didn't take exactly this advice, that doesn't mean they don't value what I do, and I can still help them. Sometimes even just having someone to talk to can open up a problem for you. And as an advisor, that's very much the way I look at my role. As you know, Matt, being a CEO is the loneliest job. You have to tell a certain story to the board. You have to tell a certain story to the company. Usually, the truth isn't either of those. It's somewhere in the middle, but it's usually only partially the truth to both sides. And that's super- lonely. So as an advisor, I just try to be a person they can just be honest with, instead of having to do the dance, having to smooth out the curves for the employees. Because you don't want your employees riding the roller coaster. You have to ride the roller coaster? You want them to ride the nice smooth rollercoaster, right? So that's what I try and do, is really be that person. Because I know how lonely that can be.

Matt Blumberg: I am sure you are a great advisor, if that's the approach that you take on the way in, because it is a tough job. You'd like to think your board members are going to be helpful, and they are on a bunch of things. But they have their own bias and perspective on things. And getting truly unbiased feedback is hard to come by.

Laura Mather: Yeah, exactly. And trying to manage all of those egos. Most board members have egos; they do. I don't think that's going to offend anyone... Maybe it will. But trying to manage all of those and maintain your own sanity as a CEO can be really, really challenging.

Matt Blumberg: Yeah. All right. Well, I think we should wrap it there. You've had a remarkable career, and it was great to learn more about it today. Thank you for joining me, Laura.

Laura Mather: No, I'm thrilled. This was super- fun. Thanks for having me.