Linda Abraham. 2 Exits + 4 Kids = 1 Incredible Woman
Episode - 53
Linda Abraham. 2 Exits + 4 Kids = 1 Incredible Woman
Linda is one of the most extraordinary women I’ve ever met. She’s in a class of her own.
She’s been navigating the post-exit world for 28 years, ever since her first exit.
And what an exit it was: a 5X return to investors in just two years!
She went on to lead her second company, comScore, from founding to IPO—building it into a global powerhouse in digital analytics, with offices in 23 countries.
Today, Linda runs Crimson Capital, investing her family’s money in early-stage tech companies, and serves on several boards, including Tiger 21.
But what blows me away most is that she built all of this while raising four children—and thoughtfully nurturing deep, loving relationships with each of them.
This episode is about an extraordinary entrepreneur who managed to do it all—and built a life that’s not just financially successful, but deeply, holistically fulfilling.
There is so much we can all learn from her!
What We Discussed:
00:00 - Introduction and reflections on Linda’s first business exit
03:34 - Selling Paragren Technologies and emotional response
04:36 - Starting the next venture and skills assessment
05:55 - Creating comScore and early funding story
08:11 - Frugality and surviving the dot-com crash
10:30 - Pivot to audience measurement and analytics
11:36 - Selling data to financial institutions like Citadel
11:59 - IPO and financial outcomes for the team
13:00 - Motivations beyond money and public company growth
14:01 - Leaving comScore and reflections on career satisfaction
15:10 - Post-exit transition and board work
17:09 - Realizing need for a break and pulling back from overcommitment
18:19 - Shift to board advisory roles and family balance
18:49 - Motherhood and managing with four children
20:09 - Family-first values and support system
21:48 - Daily decision-making and sacrifices
24:49 - Health and lifestyle improvements post-exit
27:25 - Transitioning from entrepreneur to investor
29:01 - Challenges in board work and mindset shifts
31:18 - Finding joy and variety in board roles
33:42 - Investing in second-time founders and founder motivations
38:15 - Raising children with wealth and aligned values
40:50 - Reflections on adult children and family discussions
43:07 - Delaying wealth conversations and individual approaches
46:21 - Continuing involvement in husband’s new startup
48:04 - Evolving motivations and contribution style
49:42 - Creating balance through mindful time management
52:45 - Focus on impact and strategic contribution
56:12 - Mentorship, support, and satisfaction in giving back
57:60 - Work, family, community: expanded arc of purpose
59:58 - How Linda wants to be remembered
01:01:14 - Conclusion and farewell
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Anastasia: [00:00:01 - 00:00:04]
Welcome to Exit Paradox, where we explore.
Anastasia: [00:00:04 - 00:00:11]
What actually happens after a successful business exit. I'm your host, Anastasia Koroleva.
Linda: [00:00:15 - 00:00:20]
I think my sense of purpose goes well beyond my work. It extends to my family. I would say my arc of purpose has expanded.
Anastasia: [00:00:20 - 00:01:40]
Linda Abraham is one of the most extraordinary women I've ever met. She's in a class of her own. She sold her first company 28 years ago, delivering a 5x return to investors in just two years. But Linda didn't stop there. She went on to lead her second company, comScore, from founding to IPO, building it into a global powerhouse with offices in 23 countries. Today she runs Crimson Capital, investing her family's money in early stage tech companies and serves on several boards, including Tiger 21. But what really blows me away most is that she built all of this while raising four children and thoughtfully nurturing deep, loving relationships with each of them. This episode is about an exceptional entrepreneur who managed to do it all and builds a life that's both financially successful and holistically fulfilling. There's so much we can all learn from her.
Anastasia: [00:01:40 - 00:01:43]
Hi, Linda. So happy to have you here.
Linda: [00:01:43 - 00:01:45]
Hi, Anastasia. Great to see you.
Anastasia: [00:01:46 - 00:02:09]
So, Linda, we just talked about how your first exit was 12, 28 years ago, which for me is. It just excites me so much. You have no idea. Because it means that unlike most people I talk to, you had almost three decades of post exit experience and a chance to process. Process it and move on from there.
Linda: [00:02:09 - 00:02:15]
Well, yes, for sure. It's hard to believe it's 28 years ago, but it was.
Anastasia: [00:02:15 - 00:02:35]
Well, you've done so much since then. So we'll focus on this today because this podcast is all about what happens to after a successful business exit. So if we go back to that moment 28 years ago and you just sold Paragraph Technologies, how did you feel?
Linda: [00:02:35 - 00:03:37]
Well, it all happened, you know, very quickly. It wasn't really expected that we would sell it that quickly. We had, you know, visions of building it into something really big. But we basically got a, you know, an offer that we were not expecting and it was kind of too good to pass up. And so how did I. How did I feel? I felt kind of wow. We built something of real value in a relatively short amount of time. It was about two and a half. We were just about two and a half years in and all of our investors, you know, had like a 5x return, which they were very happy with. And it was definitely great for us personally. My kids were. My son was very young at the time. I Had yet to have my second daughter. But it was a time of kind of great excitement. We felt very accomplished and really very excited.
Anastasia: [00:03:38 - 00:03:48]
So how did that translate into your next business? How did your motivation change? Why did you even decide to do it again?
Linda: [00:03:48 - 00:06:57]
Well, it was a really interesting time. It wasn't at all obvious what we wanted to do next at all. And my husband and I did both of our companies together. So one of the benefits of working with your husband is you have a lot of opportunity to talk about it and brainstorm. But the first thing we did was none of that, was just sort of take a breath and think about, you know, very carefully what we wanted to do next. And it was a very interesting time. It was 1999. The Internet was first getting started and we were, you know, sort of collectively taking stock of what we were good at, what we really enjoyed doing, what we were good at. And, and we were both very good with data, very good with analytics. My husband in particular was really great at being a technology visionary and innovator, and I was good at selling products, commercializing things. We had another co founder who we had worked with previously at our previous company, before Peregrine, and he and another investor kind of approached us with this idea that, you know, collectively you have the great, great collective skill set that you could really be. The Internet is going to be something someday. At the time it was, you know, just getting started, but, you know, the notion was that as it grows, it's going to mean it's going to need a third party scorekeeper of some kind. And you guys kind of have the collective intelligence and the right experience to be able to play that role. You've heard of Nielsen for television and Nielsen television ratings, and they have their sort of the currency of buying and selling ads online. We could potentially be that for the Internet. And so we started thinking about it and one thing led to another and we went out to. We put some ideas together and at one point we went out to Silicon Valley to test out the PowerPoint deck and pitch it to a few people. And at the time, this will be very different for you, because you weren't around then. But at the time, money was flowing to the Internet like crazy. It was very overfunded. If you had an idea, you basically were able to get funding. It was kind of crazy. So a lot of ideas that were funded in that period that should not have been, but we had a 26 page PowerPoint presentation, much of which we wrote on the plane between Washington D.C. and Silicon Valley. And we ended up getting a $26 million valuation and all we had was an idea. We had no product, we had no employees, we had no technology. We just had an idea and a vision of how we were going to do it. And we got funded at, you know, a great valuation. So that's kind of how we got started.
Anastasia: [00:06:57 - 00:07:04]
That's amazing. But do you think it was a good thing that you had so much, much money early on?
Linda: [00:07:05 - 00:07:06]
Absolutely.
Anastasia: [00:07:08 - 00:07:10]
In fact, there's a downside to it. Right.
Linda: [00:07:10 - 00:08:43]
Well, you know what we were doing, and keep in mind the time frame here, we were going to build. We were going to basically create a panel of people who were going to volunteer to let us, you know, track everywhere they went on the Internet anonymously. We were not going to collect pii, but we were going to build a panel of a million people from around the world. And this was pre cloud, so it was a very capital intensive business. We had to buy all of our own servers, we had to, you know, manage all of our own technology. So it was extremely capital intensive. So that being said, we. If there was an award for being frugal with how you spent every dollar, we would have won it because we were very, very, very scrappy with the money. We never bought new desks, we always bought used desks and polished them ourselves. We were very, very, very scrappy with, with the money, which turned out to be great because the next year was 2000 and all of our major clients went out of business. And so we really crashed during that was a very tough period. We call it the Internet nuclear winter. And a lot of those companies that were funded ended up going out of business. In fact, of the companies that were funded in 1999, only 5% of them survived 10 years later, and we were among them.
Anastasia: [00:08:43 - 00:08:47]
It was your frugality that helped you be in a different position.
Linda: [00:08:48 - 00:12:00]
Well, that was a part of it. That probably wasn't even the primary position. But yeah, we did preserve cash, and we were glad that we did. But what really helped us was being able to kind of think on our feet and think creatively about how to come up with additional uses of this massive data asset that we had built. Because when we first started, our early vision was that we were going to measure e commerce primarily. And so we had big clients like Pets.com for example, which was a huge company with a huge valuation at the time. They were one of our biggest customers. And when the Internet crashed in 2000, a lot of those early e commerce companies went totally out of business and there went our Revenue. So here we were with this very unique data asset, you know, million people from around the world and we were measuring everything that they, everything they did on the Internet, everything they bought, everywhere they went. And so we had, we basically pivoted from that E commerce tracking model to more of an audience measurement model. What we were measuring full audiences and we were doing a lot more analytics and developing products that helped people basically move their business or be able to compete online using our data. And so it was a period of tremendous creativity, but we were, it was really, there's nothing that pushes you to be creative than the need to survive. And that's really where we were. We were, you know, dangerously close to failing and failure was just not an option. So we kept coming up with new and different creative ways of using the data. I mean, one example is we came up with an application where you could take this data and use it in financial models. There was a major hedge fund whose name I probably shouldn't say, but it's very well known hedge fund. I guess I can say who it is. This is a long time ago. Citadel. We weren't able to say their name at the time. We referred to them internally as Bulldog. They were only like three people who knew the actual company. But basically we sold them exclusive access to our data for, you know, millions of dollars because they were using it to find out on their side, you know, which companies were going to win and lose in the age of the Internet. And we had this very unique early insight as a, as a heartbeat of which, you know, which companies were doing well with regard to reaching people online and which people, which companies weren't. So they were able to incorporate that as one of the inputs into their financial models and do a better job at predicting the health and success of companies in the digital world. So that was just one of many, many kind of new twists on the data asset that we had developed. And we just kept coming up with more and more of them and we ended up coming up inventing kind of new lines of business that really helped us get through that difficult period.
Anastasia: [00:12:00 - 00:12:05]
So despite all these difficulties, you IPO in just seven years after you started.
Linda: [00:12:05 - 00:12:06]
Yeah.
Anastasia: [00:12:06 - 00:12:10]
And that was a much bigger exit for you personally.
Linda: [00:12:10 - 00:12:11]
Yes.
Anastasia: [00:12:13 - 00:12:14]
So I often talk to.
Linda: [00:12:14 - 00:12:23]
Yeah. And in fact, I was just going to say what? Not just us, but one of the proudest things in our lives is we minted, I think, 31 millionaires that day.
Anastasia: [00:12:23 - 00:12:25]
That is huge. And it's very important.
Linda: [00:12:25 - 00:12:30]
That was one of the greatest things that happened. Not just our own personal Success.
Anastasia: [00:12:30 - 00:12:35]
But did you stay on after the IPO?
Linda: [00:12:35 - 00:12:37]
Oh, yeah, I was there for 15 years.
Anastasia: [00:12:37 - 00:12:50]
For a while. You kind of. Your financial situation changed, but you were still very busy working. Why did you continue working even though presumably you could afford not to?
Linda: [00:12:51 - 00:13:58]
For me, it was never about the money. Still isn't about the money. It was, you know, to me, it's really. Money is really a byproduct of doing something that you really believe in, that really motivates you, that you enjoy, that you find challenging. And so, you know, having the opportunity to, you know, play a major role in running a public company was a whole new set of challenges. It involved a whole new set of things. It allowed US Capital, for example, to expand internationally, which is something I spent a lot of time doing. We. It also allowed us to do a bunch of acquisitions, which I was also very involved in, having led many of them. And so it really allowed us to expand in a way that we couldn't have otherwise if we had just been relying on cash flow. So it was really a very pivotal moment of change and an opportunity to turn comScore from a US based company into a global company. And by the time I left, we had 32 offices in 23 countries. So that was quite a journey.
Anastasia: [00:13:58 - 00:14:01]
Amazing. Why did you leave?
Linda: [00:14:02 - 00:14:55]
Well, you know, I kind of subscribed to the Steve Jobs, you know, edict when he talked about if you wake up every morning and you look in the mirror and you're really, you know, excited about what you're doing, then you keep doing it, but when the day comes where you're not, then it's time to do something else. And I kind of got to that point. I had done kind of everything I wanted to do, and I felt like I wasn't really learning that much anymore. It was really becoming more of what I already know how to do over and over again. And that's just less interesting to me. So I, you know, when I got to that point, you know, just picked the person that thought was gonna basically be able to do what I was doing and worked with him to, you know, take over my role. And it was all, you know, all very orchestrated, all very positive. So I had a great team and they, they kept doing what they were doing.
Anastasia: [00:14:55 - 00:15:10]
So that's when your actual exit happened because you suddenly had no longer place to go. You know, a purpose and structure and all of that. How did that feel?
Linda: [00:15:11 - 00:17:06]
Well, in the beginning, it was, you know, I would say, a little bit disconcerting not having the structure of, you know, having a Going to an office every day and having a, A team. But one of the things that I did was at, well, at comscore was a lot of M and A work and that got me always. That had me very. It sparked an interest in learning where technology is going because I was always seeing new startups, new companies, what they were doing. And our challenge at cost was, you know, do we build by our partner? And that was one of the things that I was always thinking about, where's technology going? Could we build this thing or should we buy it? So I ended up connecting with lots and lots of technology startups there all over the world, which was an amazing experience. So that sparked an interest in new companies. Some of those companies I ended up investing in and then once I invested, they would ask me to be on their board. So I did a lot of board work. So it was sort of a very natural transition to doing what I started doing with early stage tech companies because a lot of the companies somehow with my background kind of found me. I didn't really have to go out and look for companies. It was sort of. I had a pretty broad network of people that I worked with and knew lots of people in the venture capital community. And so there was a lot of collaboration. People would bring me in to kind of say, hey, I'm looking at investing in this company. Can you give me your ideas? What do you think? So I had this. It kind of gave me an opportunity to, you know, sort of transition into something else without having to work too hard to find it, I guess.
Anastasia: [00:17:07 - 00:17:09]
Did you take a break?
Linda: [00:17:10 - 00:18:16]
I did take a break and I. But I didn't take a break right away because, well, I kind of jumped into a lot of things very quickly. And I think that's just because part of my personality is that I'm interested in lots and lots of things. And so almost, you know, if I saw something was interesting, I would kind of get involved in it right away. And collectively, I remember, you know, my husband saying to me about six months out, like, I think you're busier now than you were at comscore. And so, you know, that got me thinking. And so then I started to kind of pull back a little bit and my break really came maybe, you know, a year and a half after leaving comscore because I really started saying, wait a minute, I really don't want to sign up for, you know, another full time role yet. I'm really missing out on part of what I should be experiencing here. And so I started backing off a little bit and getting involved in fewer companies in, in bigger ways.
Anastasia: [00:18:16 - 00:18:20]
And what did you do instead if you started working less?
Linda: [00:18:20 - 00:18:28]
Well, I was. Started working, you know, working with, on boards of companies and doing advising for some of the startups that I was working with.
Anastasia: [00:18:28 - 00:18:31]
Yes. So less of day to day work and more.
Linda: [00:18:31 - 00:18:33]
Less of day to day, yeah.
Anastasia: [00:18:33 - 00:18:43]
So. So you have four kids. So I imagine it was quite a challenge to balance your motherhood and business.
Linda: [00:18:43 - 00:18:44]
Yes.
Anastasia: [00:18:45 - 00:18:48]
Helped you. How did you manage to do that?
Linda: [00:18:50 - 00:20:12]
Well, let's see. Yeah, Lots of younger women ask me this question and I guess I have a couple of different answers. One is that it is. First of all, it's not easy, as we all know, but part of the approach that I took was I didn't try to figure it all out at once. When you have four kids, they're in different stages and there's quite an age difference with my kids. So two of my older kids are not mine biologically, but they are very much mine in my heart. And, and then I have got two that were younger. So they're going to be. They all were in very different stages and I really tried to mold what I was doing around what their needs were in a lot of cases. And I had fantastic help at home. That's a key part of the, that was a key part of the ingredient for me. We had an amazing nanny and one of the best decisions that we made was when we first started comscore, we gave her some founder shares when they were worth nothing. And today she owns her own home and drives Alexis. So she, she, so she was, she.
Anastasia: [00:20:12 - 00:20:17]
Was also very interested in the success of the business. Right, Your aligned interest.
Linda: [00:20:17 - 00:23:14]
Well, we were kind of, you know, we kind of said, look, this is going to be quite a ride. There's going to be, there's going to be lots of unanticipated things. We're going to need, you know, extra help from you. But basically the philosophy was, you know, when I'm with the kids, I want to be 100% focused on the kids. And she would focus on the house. You know, when I, when I was at work, she would be 100% focused on the kids. And, you know, I didn't really care about the house, that kind of thing. So the kids always came first. And, and I think the advice I would give to younger mothers is I think there's a tendency to figure it out all at once. What is this formula? What is this magic formula that I'm going to use for work life balance? And I think that's just the wrong question. It is really a daily question. It's very fluid and you have to be able to be flexible and you've got to have great people around you. And the key thing is you've got to have an amazing husband, which I'm really blessed with because we were 100% aligned that no matter what was happening with the business, family came first and we would just do our best kind of on a day to day basis. And there were plenty of times that I would, I mean, let me step back. I mean the reality is you cannot be in two places at once. You know, you can either be at your kids basketball game or you can be closing a big deal in New York. You cannot be in both places. So there were plenty of times where I had to have someone from my team go and do something that I would frankly, you know, in many ways prefer to be doing. But because of the needs of the family, I did not want to travel or wanted to be somewhere else. And so you have to put your ego aside and you have to say what is the best way to get this done? And everything I have to get done. And so. And that means in some cases you end up not doing some things that you frankly think you could do better than the person that you're sending in some cases or in other cases you just something that you really enjoy doing and you don't get to do and you instead have to do something that you enjoy less. So there are, you know, there are daily trade offs and there's no one right way of figuring it out that you can kind of say, here's the formula, here's what I did, you should do it too. I just don't think that exists. I think every kid is different. The four of mine had different needs at different points in their lives and that applies to their dad too. There were plenty of times where my husband would be in a better position for whatever one of the kids was going through to be able to handle it. So I would pick things up that he was doing so that he could, you know, he could do whatever he had to do with the kids. So very much of a long answer, but I would say it's a, was a daily challenge.
Anastasia: [00:23:15 - 00:23:21]
Yeah, it's a teamwork. If we think about building a startup, it's also very fluid.
Linda: [00:23:22 - 00:23:23]
Yeah, absolutely.
Anastasia: [00:23:23 - 00:23:47]
At the end of the day it's how well people cooperate, how well they gel together. Because also in the beginning in a startup, it's not always clean, clear who does exactly what job. So I personally Think that the family in this sense is not that different. I agree with you completely that it's you, you grow with your children, with your husband, you grow together and learn.
Linda: [00:23:48 - 00:24:44]
Yeah. A lot of people would say to me, you know, oh, how I could never work with my husband, you know, how do you guys do that? And, and you know, I kind of have two answers to that. One is that we worked together before we got married very effectively. So we kind of had pretty strong series of data points that we worked well together. But the second is that when you're both entrepreneurs and you are building the same company and you're building a family, you're very organically and kind of holistically aligned. And if we were both building two separate companies, I think would have been a hell of a lot harder. But the fact that we both had, we were very aligned on what was important, what our priorities are and how we were going to make those trade offs and we helped each other and we had a fantastic team that was just outstanding. So we were really lucky.
Anastasia: [00:24:44 - 00:24:46]
But still, it had to be difficult sometimes.
Linda: [00:24:46 - 00:25:52]
Oh yeah, it was. Well, one of the sacrifices that I made, which I only realized after I left Comscore, was I really did not stop sleep enough for 20 years. I, I was always tired and I kind of didn't even realize that until I stopped. And still I had the luxury of being able to wake up without an alarm clock, which I actually think is the most meaningful sign of wealth that one can have in their life. It's being able to wake up. Yeah, I, I really didn't even realize. So for me, that was, you know, that I was working a lot. You know, as soon as the kids went to bed at night, that was a big time of creativity for me and productivity. And then, you know, if you work till often till, you know, 1, 2 in the morning and you're up at 6, you know, that's just not enough sleep. So that was a big sacrifice, which I only really realized in retrospect. I didn't realize it as much in the.
Anastasia: [00:25:53 - 00:25:59]
Was it that during that break that you slowed down and caught up on your sleep?
Linda: [00:26:00 - 00:26:00]
Yeah.
Anastasia: [00:26:01 - 00:26:12]
How long that, how long of a break did you take and what else helped you transition to a more holistically healthy lifestyle that you have now?
Linda: [00:26:14 - 00:27:25]
Well, I think, you know, the luxury of time and the luxury of focus was really terrific. That was a terrific bridge for me. So, for example, I was able to focus a lot more on my health, which I have been, you know, doing much more so than when I Was building, building the companies I was able to, you know, get involved in exercise, just read a lot more about health, just try a lot of new things that I wasn't able to try before. And that really kind of opened my eyes to a lot of things that I really had been missing. So that was a, that was a very pivotal thing for me. And it also led to, you know, some interesting investments that some of them have not yet worked out, but hopefully they will someday. But I think that that was very eye opening and this a recognition that health as you get older is not something that's going to take care of itself. You kind of take it for granted when you're younger, but I no longer do that.
Anastasia: [00:27:26 - 00:27:35]
Yeah. So most of us find it pretty difficult to transition from an entrepreneurial mindset to an investor mindset.
Linda: [00:27:35 - 00:27:36]
Yeah.
Anastasia: [00:27:36 - 00:27:39]
How did it happen for you?
Linda: [00:27:39 - 00:29:00]
Yeah, I learned some hard lessons with that transition when. So in my journey, when I started investing, one of the things that you notice is that, you know, when entrepreneurs want your money, they tend to agree with you on a lot of things. And so I would look at a company and I would sort of, I would, you know, evaluate the product, evaluate the technology, and develop an opinion on, you know, what I thought it could be and, you know, talk with the, the CEO about these ideas. And you tend to get a lot of yeses during that conversation. But what I really learned is that, you know, there is the things that can make you a very good entrepreneur or a reasonably good entrepreneur can make you a terrible investor, because if you bring with you the, you know, optimism or vision that you think could be, and the end of the day, the CEO doesn't either agree with you or they can't execute on what it is that you're both discussing that ends up not working out. So I learned some hard lessons there. And I also learned that there is a, you know, the transition from being an entrepreneur to being a board member is something you have to be very, very mindful of in that context.
Anastasia: [00:29:00 - 00:29:07]
And so can we talk about this in more detail? Why is that difficult?
Linda: [00:29:08 - 00:31:17]
Why is it difficult? Well, because, you know, when you are very operationally, you know, experienced as I was, you tend to, in a lot of cases, go right to how you would fix the problem if you were involved and, you know, if you were operationally involved and you don't have that same, you know, you're sitting on a different branch, looking at a situation from a different point of view. When you, when you are a board member now, in some cases, you bring A perspective, expertise that the, that the CEO, you know, can't see. And you're able to kind of add value that way by, you know, having him or her think about things a little bit differently. And that's really the, you know, the hope, you know, in terms of one of the ways you're adding value. But you know, initially my head always would go to what I would do if I were in that situation. And the reality is I'm not in that situation. I'm not running the company. So the most productive thing I can do is translate that into more of a strategic question and more of a strategic discussion about what the options are and think about things from a higher level with also for the full recognition that, you know, I don't have the same familiarity with all of the day to day details of how the business is being run. I'm looking at it at a much higher level. So it took me a while. I would say that took me, I would say I probably had about a two year learning curve of being very, very conscious of that and also, you know, asking other who I was sitting on boards with for feedback on that regard in terms of how it was that I was presenting myself, how it was that I was adding value, the kinds of things that I was raising, the way that I was having conversations. And I learned a lot in those two years about how to be a better board member and advisor and the difference between that and being the entrepreneur.
Anastasia: [00:31:19 - 00:31:33]
Many people find sitting on boards quite boring after an entrepreneurial journey because there is not as much control or a chance to channel our creativity into our business.
Linda: [00:31:34 - 00:32:46]
Did you feel that I've enjoyed it? I, I think that, I mean, some have been more interesting than, some roles have been more interesting than others, obviously, as is always the case. But I really like the variety of thinking about something different every day. Every day for me is different and I have, I really like that variety. I also like, I operate, I personally operate best in cases where I have one foot in something that I don't know anything about and one foot in something that I'm, you know, expertise and I'm really leveraging from, from my experience. And so a lot of these board roles are cases where I'm, I'm learning a lot about a new business that I know nothing about. And so no, I don't find that boring at all. I, I find the, the variety to be really stimulating and it really leads me to, you know, brand new areas of learning that in, in a, in a sort of a firsthand way that I would otherwise never have an opportunity to understand. So I enjoy it. But it's a very personal thing.
Anastasia: [00:32:47 - 00:33:42]
It certainly is. And I found that understanding this about ourselves is extremely important when we, at this moment, when we're thinking, okay, what do I do now? I have all the freedom, I can do all these different things. And committing to something that is not natural for us is quite dangerous. We waste a lot of time, sometimes money as well, and energy. But it sounds like for you it was a good choice, which for me is fascinating because most people I talk to give up on sitting on boards out of boredom very quickly. But it's great that you found something that stimulates you for a long time. Now, Linda, do you, when you invest in companies, do you prefer to invest in people who already had successful exits before?
Linda: [00:33:44 - 00:34:17]
Yeah, I think, yeah, there's definitely. And that's another thing that it took me a little while to learn when I was first not as judicious about that, I would say I tended to fall more in love or get more interested in the product later on. Working with people who have done it before is definitely preferable for sure.
Anastasia: [00:34:18 - 00:34:19]
Because of the experience.
Linda: [00:34:20 - 00:35:21]
Because of the experience, because of the maturity also. And you know, I tend to want to work with people who are really solving problems that they really, you know, they really believe in their solutions. And you know, when I, if I hear the first pitch from someone and this happens in a lot, in a lot of first time entrepreneurs, you know, they start talking about their exits in the first presentation, that's an immediate no for me. I want to hear what problem you're solving, why you're solving it, how you're solving it, why you think your solution is unique. And second time entrepreneurs tend to be doing it because they have good answers to those questions and they're not, you know, just doing it for the money. If I get, if I get any kind of a sense that someone is only in it for the money, that's a real big turn off for me.
Anastasia: [00:35:21 - 00:36:47]
But oftentimes when I talk to exit founders, they have this. Those who exited recently, especially if they're quite young, they actually are very afraid that they will no longer be hungry financially to start another business because it does take time for that motivation to evolve. And I know exactly what you're talking about second time founders, when they are genuinely not motivated by money, even if they were in the first business. But that transition in motivation does take time. What I found, for example, was I started angel investing a lot after the first exit and I had this Idea that I'm going to only give my money to people who built businesses before successful businesses. And I thought it was such a great idea. But it soon turned out that I underestimated just how risky it is. If people who had successful exits jump into a new business too early and then they realize they haven't done this exercise yet, what it is they actually care about, what it is they want to do, they may jump into a new business for completely wrong reasons like getting the identity back, and then it becomes dangerous. Actually, there are risks out there that are very specific to repeat founders that don't exist for first time founders.
Linda: [00:36:48 - 00:38:15]
I think that's a very good point. I definitely agree that it takes time. And that's one of the other lessons that I learned because like you, I, you know, I did some in the beginning, I did a lot of angel investing and, and I was too quick to invest in the beginning. And now I take a lot of time to get to know someone. I take a lot of time get to know someone, you know, the team. And if, you know, if, if the question is always, oh, well, are you going to invest or not? We need, you know, we need an answer by Friday. The answer for me is always no. I would, I would much rather, you know, miss out on the next big opportunity than then think that, you know, be forced to invest in something before. I'm really, really convinced that the person's motivations and skill sets and where they are in their life, et cetera, are aligned with what it takes to build a company. Because it, you know, it's not easy, as we both know. But I also feel that when you're an entrepreneur and you're a real entrepreneur for all you really want to solve problems, that you often have a couple of them in you, a couple of bites of the apple in you, and if you can be lucky enough to find those people, it can work out great.
Anastasia: [00:38:17 - 00:38:41]
So, Linda, a completely different topic now. You and I had this wonderful lunch in Sunny Isles, Florida, and we were talking about how to raise kids with wealth and raise them as good people. And I would love to bring this conversation to my audience. So how did you go about raising your kids and not spoiling them?
Linda: [00:38:42 - 00:40:37]
Yeah, that's, that's a, that's a really tough thing and something that we all struggle with. I can say that it's another area where my husband and I, fortunately were, you know, 100% aligned. We tried to be really very, very careful with not raising our kids in a way that they, you know, were entitled you know, expected things. We gave them, you know, they're all thankfully doing well now. They're all kind of naturally, you know, independent. But when we were growing up, we just tried to help them make day to day decisions that really reflected our values around money. Then you contrast that as they got older, we were able to take nicer vacations. Our kids are smart, all kids are smart. They figured out that there was money involved. But we just tried to basically live our day to day life in a way that really reflected our, our values. And we're both still, I mean, my husband still likes to buy his shirt sometimes from Costco. So it's kind of, I think when you have values and you didn't, you know, you didn't come from money, you don't give that up easily. You know, he grew up on a farm in Lebanon picking apples and looting them on the backs of donkeys and bringing them into town and selling them. And, you know, I grew up in a very modest household, so I don't think that ever leaves you. And I think you just sort of naturally pass it on to your kids. But there were plenty of cases where their friends were getting this and that, this other thing. And you know, our approach was always, well, we'll give you what we think is appropriate and then the rest is up to you.
Anastasia: [00:40:38 - 00:40:42]
Yeah. So there are doubts now. Do you feel it was the right choice?
Linda: [00:40:44 - 00:40:45]
I'm sorry, what?
Anastasia: [00:40:46 - 00:40:47]
So your kids are adults now?
Linda: [00:40:47 - 00:40:48]
Yes.
Anastasia: [00:40:48 - 00:40:50]
Do you feel you made the right choice?
Linda: [00:40:53 - 00:41:55]
I think we did the best job that we could. Again, I think the best evidence of that is that they're all out of college now. They all recently got married to terrific people. They're all financially independent, supporting themselves. We recently first got together as a family for the first time and really talked about some of this. We didn't really talk about money a lot, in fact, kind of at all during their whole upbringing. It was just not something that we kind of talked about. So I think we did the best job that we can. I think it really starts with your personal values. And so I feel good about where all of our kids are. And I think we had a very healthy conversation about it for the first time as a family recently. And it was kind of cathartic to kind of confirm that some of those values had really made their way into the minds of our and hearts of our kids.
Anastasia: [00:41:55 - 00:41:59]
Why did you decide to have a family meeting and talk about these things openly?
Linda: [00:42:00 - 00:43:08]
Because, you know, we're getting to an age where anything could happen and, you know, we we actually, we've done all the estate planning things that, you know, we've been advised to do by people at tiger21 and others. And. But we also felt that there was something missing, you know, other than the mechanics of how. How money would transfer. And that was a discussion around what we really hoped to accomplish with passing down wealth. And when we put it into a letter, actually, which took us kind of a couple of months to write, we went through sort of several rounds of revisions. And we wanted to talk about it with them and talk about what our values are, and we wanted to get their input on their values and basically make this an ongoing conversation around how this money would hopefully improve the quality of their lives, how we would hope it improved the quality of other people's lives outside the family. And we had an opportunity to do that. So it was a very positive discussion.
Anastasia: [00:43:08 - 00:43:58]
So there is, of course, a different school of thought that these discussions should start as early as possible with little kids. And lots of entrepreneurs feel uncomfortable doing that because we are afraid that if our kids expect to get wealth from the parents, that they will never have the necessary motivation to become financially independent. Entrepreneurial or not, but financially independent. And if you talk to someone in this situation now, given your experience, would you recommend the way you did it, which is, I understand, waiting until kids grow up, or you think it is a good idea to start talking about wealth materially?
Linda: [00:43:59 - 00:46:22]
Yeah, no, I'm definitely in the first camp. I mean, our kids range in age from 28 to 1 just turned 39. So most people would argue that this is very, very late to start having this conversation. But no, we absolutely had those concerns, particularly because there's a big age range with our kids. And, you know, we were afraid that, you know, perhaps not afraid, but we wanted to make sure that the younger ones in particular, because, you know, they weren't as mature or experienced as the older ones, wanted to make sure that they. They knew that, you know, they had to work hard for, you know, their own development and for their own success. And we didn't want to. We didn't want the knowledge about what might be waiting for them financially to be a detriment to that. So, again, but I also think that, you know, every child is different. Every family is different. I think, you know, my older son who went on to become a very successful entrepreneur, you know, his. His view is probably different. His view is that, you know, having, you know, having some financial freedom early on gave him the confidence that he needed to go off and build a company and I think that was right for him, and that's so why we did part of what we did with him. But with the other kids, we're different. You know, every kid is different, so I don't think there's one. But in our case, we wanted to make sure that we weren't treating any one kid differently than the others. And, you know, that this was our. The best way of doing it was just to sort of hold back, not talk about it until everybody was really ready. And so for us, I think that's the right. That was the right answer. At least we all feel really good about it. The kids, you know, kids are very, very appreciative of this meeting that we had. And I think it was a very productive meeting. So we feel good about it. Is it the optimal answer? You know, should we have started earlier? I'm not sure I would see the benefits of that now, but I did see some risks earlier on, so I'm glad that we did it the way we did it.
Anastasia: [00:46:23 - 00:46:26]
So are you still in business with your husband?
Linda: [00:46:26 - 00:46:51]
Well, I am on his. He is doing another startup in a totally new space in the pharmaceutical space. I'm on his board and of course we were invested, investing heavily in his company, which is why I'm not doing any other new deals right now, because I'm really investing in him. But. So I still work with him in that capacity, but I'm not operationally involved in the company anymore.
Anastasia: [00:46:53 - 00:47:05]
So he decided to go back to pure entrepreneurship. Yes, quite want to be an investor. So that's fascinating how you ended up taking a different class.
Linda: [00:47:05 - 00:47:45]
And his journey is interesting too, because after he left comscore, he went out to teach at the Stanford Business School for a few years, which is something that he had sort of thought about doing for a long time and did that for a few years. And then he really realized that he kind of wanted to be. That being an entrepreneur was more interesting than teaching entrepreneurship. And so he wanted to kind of be in the arena again. So he took a totally different path and he's enjoying it as well. So I'm, you know, playing that role on the board for him, which I play for other people, which is helping at a strategic level. But I'm not involved operationally. I'm certainly rooting for him.
Anastasia: [00:47:45 - 00:48:04]
That's fascinating. If you, if you think about your motivation, ever since you first started the first business and up to today, do you think it has changed, it has evolved or it's been very stable, basically focusing on what you love doing as.
Linda: [00:48:04 - 00:49:15]
You mentioned before, I think it's evolved, certainly in terms of the content of the motivation, in terms of the problems that I'm solving, I would say it's evolved into a mode of contribution that is quite different. Less intense, but hopefully higher, you know, high impact, less intense, you know, day to day. But I also enjoy being able to have, you know, more control over my schedule. I also really enjoy picking and choosing and being extremely selective about what it is that I do and how I spend my time, and also being able to take an afternoon off and play golf. So does that mean my motivation has decreased? I guess in some sense maybe it does, but I don't feel that way. I feel like on the things that I'm involved in, I'm very committed to helping them be successful, but I'm just not doing it 247 in a way that the weight of all of the responsibilities on my shoulders, and that's very, very different.
Anastasia: [00:49:16 - 00:49:42]
And this is exactly what I'm trying to understand better and learn from you. How did you create that balance or that integration in your life? What it is we could kind of learn from your experience on how to balance entrepreneurial drive with the desire to sometimes play golf. Where do you draw the line? What are your rules, maybe, or your tips?
Linda: [00:49:43 - 00:51:32]
Well, I tend to. I tend to think very consciously, you know, usually on Sundays, about kind of how I'm going to spend my time that week, what the next couple of weeks looks like. And when you're on boards, you know, particularly public companies, some of those things are set. You know, most of those meetings are set a year in advance, so you don't have any flexibility on those things. But other than that, I really do. And if I've got a lot of things coming up, say, in earnings season, where a lot of the board meetings tend to stack together, I am just very conscious of not overloading myself, not committing. And if I feel like I. If I. If I need a day, for example, to just not have anything on my calendar or want to go play golf with my husband, I just block the day, and I proactively do that. And that's something that my husband and I have started doing in about the last year or so, and it's really worked very well. One of the things that's been great, and I would really encourage other people to do when they get to this sort of stage of their life, is be a part of a community where other people are in the same stage of life, because they tend to pull you into things that are fun and different and outside of business. And I tend to live in a, you know, you saw where I lived in this great building in Florida. And there's a great community of people here, many of whom have worked for, you know, many decades like we have, and are in a similar stage of life. And so part of what's great about it is that, you know, we get pulled into a lot of fun things. As an example, we're all going to the Galapagos in a few weeks. Like ten couples in my building. And that's not something.
Anastasia: [00:51:32 - 00:51:33]
Ten couples. Wow.
Linda: [00:51:33 - 00:52:46]
Yeah, that's not something I would have, you know, proactively done. Not necessarily, but so I think that's, that's a part of it is, is be involved in a community of kind of people who are at a similar stage of life, who you can, who will help you, kind of tempt you with kind of fun things that, that get you and then you. So that some of it happens naturally. But I think you just have to be very mindful of how you want to spend your time. Because in my case, and I've, I've been guilty of this over and over again because I'm interested in lots of things having to do with technology and companies and where they're going. If I'm not mindful of it, I will have a full solid week of meetings and I will feel like I'm working full time and I just will not let myself do that at this point. And I think over the last two years I've really gotten to a great balance that way. And, you know, learning new sports, I'm really building in some, you know, lots of time for exercise, lots of time for health related things. And then the rest of the time I'm very invested in what I'm doing and really, really enjoying it. So it's a nice balance.
Anastasia: [00:52:46 - 00:52:52]
So you mentioned also before that you're more focused on impact instead of working a lot.
Linda: [00:52:52 - 00:52:52]
Yeah.
Anastasia: [00:52:52 - 00:52:57]
So walk me through that thinking. Is it about efficiency?
Linda: [00:52:59 - 00:55:13]
It's about efficiency and it's about picking companies where what they need is something that you are uniquely qualified to give. And that's, you know, back to my comment about taking a lot of time to really get to know the entrepreneur and the team and the company and the space. You know, I've just had conversations with three different companies where I spent a couple months thinking about it, talking about them and then just sort of said, I don't think this is a good fit for me because I didn't think that what I was good at was really what they needed or wanted. Sometimes people want you to join a board just because they want you to help them raise money. That's not interesting to me. Okay. And so I kind of. And sometimes it takes a long time to kind of figure out exactly why they want you on their board. And so that's a. You know, that's definitely part of it. But if somebody is really interested in how they build and grow and scale a business, and I get them to talk a lot about the kinds of challenges that they have, and, you know, I like working with CEOs that are very open, very honest, and are going to, you know, just know that I'm. I mean, I've been through a lot as a. As an operator. I'm pretty unflappable. So I'd really rather know. I need to know kind of the full scoop of what's going on before I can really give you an honest answer and try to help you. And if I sense that that's really what people want, they really want someone that's going to help them build in a very kind of, you know, strategic but positive, constructive, decisive way, that's something that I can contribute to. And if it's really not that. That they're looking for, or I conclude that it's not that, regardless of what they might say, I just. I just pass on it. And I feel like that's a wonderful luxury to be able to have. I don't. I don't need to be building a resume. I don't need to be doing anything for any other reason other than I think that my time is going to be well spent. It's going to have a positive impact on helping this company grow and scale.
Anastasia: [00:55:13 - 00:55:21]
So it sounds like you don't just want to contribute. You want to contribute in your very unique way, which you are very aware of.
Linda: [00:55:21 - 00:56:18]
Yeah, I think that's a good description. And I also think it's important to let the entrepreneur get to know me and have conversations about, you know, examples of some of the things they're struggling with. So they can see kind of how I might, you know, approach them and how I might help them, because I do. I do get a lot of satisfaction on problem solving out of, you know, helping. Helping. You know, it's very lonely being a CEO, as I'm sure you know. And in a lot of cases, you know, people, trusted people that you can really talk to honestly and openly are kind of hard to find. And so if I sense that there's really that kind of a connection that I Can that might. I might be able to leverage my experience or, you know, my skill sets in ways that could be very helpful. I get a lot of satisfaction out of that, and sometimes that, you know, works out financially.
Anastasia: [00:56:18 - 00:56:40]
I can see how this awareness and this high standard that you have with respect to. To the board positions you accept is the reason why you are enjoying them so much more than many other people I talk to. You're just very careful, very selective, and very aware of what you want to get out of those positions. That's how I hear you.
Linda: [00:56:41 - 00:58:01]
Yeah, I think that's right. And like you, I know a lot of people that they kind of rush onto boards because they think that's the next thing. And I would caution them to say that board work can be terrible when it goes wrong, it's terrible, like really bad. And I've had some really bad experiences being a director. And why would you do it? So, again, you can't necessarily predict some of those when they're coming down the pipe. But it is not all glamorous, and sometimes it's very, very unpleasant and nitty gritty. And when, particularly if the board is a public company, you know, getting off of the board, you can't just say, oh, I don't like this anymore. I'm going to quit. You really have to. You have to think about a lot more than that. And so it's really worthy of studying the nature of the work and not over glamorizing what it is to be on a board. Private companies are a lot easier to get on and off of, but still, you know, you want to make sure that, you know, you're getting into. And I've seen a lot of people just rush onto boards because they think it's the thing they should be doing at this point in their career. And I think that's a real mistake.
Anastasia: [00:58:01 - 00:58:05]
So would you say your work today gives you a sense of purpose?
Linda: [00:58:06 - 00:59:35]
I think it gives me enjoyment and satisfaction. I think my sense of purpose goes well beyond my work. I think that it extends to, you know, certainly to my family, certainly to my extended family, which I've been able to spend more time with. You know, to my. I've got. I'm really blessed with some many longtime friends that I've had for decades, being able to spend time with them, in some cases, help them with some of the things that they're struggling with. I've also gotten involved in some other things beyond that, in terms of my community, some other nonprofit initiatives that are very meaningful to me. So I would Say my arc of purpose has expanded. When you're building a company, you're an entrepreneur. All I thought about for, you know, those 15 years I was building comScore was kids and the company, the kids and the company, and, you know, my extended family, of course, but. But now I feel like, you know, having lifted my head up from that. You know, I do a lot of mentoring of. Of entrepreneurs, a lot of mentoring of younger people who are, you know, early in their careers or different stages, struggling with things. And so I just feel like my arc of purpose has expanded.
Anastasia: [00:59:35 - 00:59:58]
Fascinating. So it sounds like you get that sense of purpose from all different types of contribution, from contributing as a mother, as a wife, as a business leader, as a director. And that feels much broader to you than maybe what used to be when it was just work.
Linda: [00:59:59 - 01:00:01]
I think that's a good summary. Yeah.
Anastasia: [01:00:02 - 01:00:14]
Brilliant. Linda, this has been so amazing. And I need to ask you the same question I ask everybody at the end of the interview. How do you want to be remembered?
Linda: [01:00:16 - 01:01:08]
How do I want to be remembered? Well, I actually just did my PD at Tiger and I did a life defense, and that was one of the questions in there. You know, at your funeral, what would people say about you? And after giving it a lot of thought and writing down a lot of things that I decided weren't really correct, I came up with something very, very simple at the end, which is that, you know, what I want people to say about me at my funeral was that that I showed up, that I, I couldn't solve every problem, but for the people and the, you know, the. That I, in my life, that I care about, for the things that I care about, I tried to show up and be there and do the very best I could and try to add value to others lives and other businesses in any way that I could. So that's kind of my quick answer to that.
Anastasia: [01:01:09 - 01:01:14]
I love it. I love it. It's so beautiful. Linda, thank you so much.
Linda: [01:01:15 - 01:01:17]
Thank you, Anastasia. Really great talking to you. I appreciate your.
