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About Lynda Weinman

Lynda Weinman is a pioneering entrepreneur, educator, and co-founder of Lynda.com, a trailblazing online learning platform. She launched the business in 1995 with her husband, Bruce, initially as a way to communicate with her web design students. Lynda.com quickly grew to become one of the first companies to turn a profit by producing educational videos, helping to revolutionize online learning at a time when the concept was still in its infancy.

Lynda’s leadership and vision led Lynda.com to tremendous growth, bootstrapping the company for years before raising its first venture capital funding in 2013. In May 2015, she sold the platform to LinkedIn for $1.5 billion in cash and stock, marking one of the most successful exits in the edtech space. The following year, Microsoft acquired LinkedIn for $26 billion, further cementing the legacy of the platform she built.

Lynda is now a full-time artist specializing in 3D printing and digital fabrication using mixed media, including ceramics, resin, and plastic. She served as the President of the Santa Barbara International Film Festival for eight years and is the current President of the Board of Maker House in Goleta. She and her husband, Bruce Heavin, have produced numerous films and documentaries, which are listed on lyndaweinman.com.

Lynda is currently focused on making art and playing bridge. She and her husband live in one of the world’s first parametric-designed homes that blends nature, art, technology and architecture.

Episode Highlights

How to stay the course in your life journey and why you should follow your inner compass
How resilience and adaptability in tough circumstances shape personal and professional success.
How to leverage self-motivation and lifelong learning, especially when your formal education doesn’t align with your strengths.
Why understanding and embracing your personal hardships can foster leadership qualities and emotional intelligence.
How personal relationships, especially in entrepreneurship, can significantly impact success when your partners bring complementary strengths.
How adapting to business challenges and taking calculated risks can be the key to your success, even when you have no master plan.
The real truth about taking on investors and the resulting loss of founder control.
Why aligning business practices with your personal values can be a win, even if it goes against conventional wisdom.
How to prepare for and navigate the shift in dynamics when taking on outside investment.
The surprising emotional turmoil involved with a big financial exit.
How to set your own rules for success, beyond wealth and external achievements to drive personal fulfillment.

Links and resources

Summerhill by A. S. Neill – A book about a free-spirited school in England that inspired Lynda’s philosophy on education.
Evergreen State College – A college where students could design their own curriculum, fostering Lynda’s self-motivation.
lynda.com (now LinkedIn Learning)- An online learning platform Lynda co-founded, offering open-ended video tutorials.
WSJ article on Lynda.com exit

Interview Transcript

Navigating The Journey

Shubha K. Chakravarthy: Good morning Lynda, we’re so excited to have you here today.

Lynda Weinmann: Thank you for inviting me.

Shubha K. Chakravarthy: We’ve got so many rich themes to go into but I want to talk about, first of all, just high-level life as a journey. You’ve talked about how it’s an evolving kind of a river and staying true to yourself is another theme I’ve picked up. What is that one truth or theme that you think has been a constant through your life and how has it played out over the course of time?

Lynda Weinmann: I think there’s a North Star for me. I actually think it’s probably for everybody when you like something and you just have that internal compass that tells you that this feels good or this doesn’t feel good.

I know it seems very rudimentary but just as you navigate your career, if you’re in a situation that doesn’t feel good, navigate away. And if you’re in a situation that feels really good, navigate towards. I just have never really stayed in a situation that I’ve been unhappy with for very long.

I was interviewing someone for something and she told me that she’d been in a job for 17 years that she didn’t like. The interview was just over. It’s like I don’t know that I can work with a person who’s willing for 17 years to do something they don’t like. We’re not going to jive. We’re not similar at all.

I think what it leads to is finding more fulfillment and really finding the right fit because there’s that adage that if you like what you’re doing, you either are good at it or you’ll get to be good at it. I believe in that.

Shubha K. Chakravarthy: Great. Has there ever been a situation where you’ve been constrained by circumstances or if somebody is constrained by circumstances but they’re forced to put up with maybe a situation that’s not as good? What thoughts or counsel would you offer in such a situation?

Lynda Weinmann: I think everybody does have those happen and it’s just like you’re making a plan B the whole time and you’re figuring out your strategy to get out of it. You’re not going to just settle to accept it.

There are lots of things in life that are very hard to accept. I don’t talk about this too often but my daughter has a chronic illness and she will most likely have it for the rest of her life.

It means that she can’t do things that she wants to do. She doesn’t have the energy. She’s in pain and it is like a process of acceptance that is extremely difficult because you’re accepting that you’re more compromised. Your mind is soaring. Your mind is creative. Your mind is having you do all these things but your body is restricting you.

There definitely are situations where you do have to accept difficult circumstances. I think it’s probably easier if you accept it than if you fight it. But of course, I’ve been privileged in life to not have to navigate something like that personally except that it’s very close to me with my daughter.

Shubha K. Chakravarthy: And that’s very moving. Thank you for sharing that with us.

Impact of Early Life Experiences

Shubha K. Chakravarthy: Moving to things that draw you away from things that repel you. One of the things I’ve learned and I’ve read a lot is that early life experiences cast a very long shadow, right?

Kind of going back, I’m just curious from where you sit now, what are some early life experiences that kind of shape that attitude or that have cast a really disproportionate shadow and in what ways have they influenced your journey?

Lynda Weinmann: Probably. I had a pretty tough childhood and for many reasons. A set of parents who had their own problems and their own circumstances. There’s usually a long story and reason why things happen and why people are the way they are. Often it goes back many many generations.

So in my situation, I had parents who were either too busy or had personal and emotional problems. In the case of my mom, she was born in a time when women couldn’t even have a credit card without their husband signing for it. A very different time.

Understanding their choices but for many reasons, I ended up having a childhood that was difficult and I lived with my grandparents for two years. I lived with my dad and my stepmother, who wasn’t happy about having children when she’d married my dad. She didn’t know she was going to have custody of three children.

I was the oldest and I was always the most responsible. I think that really shaped me a lot. My husband is also the oldest and there is sort of an oldest child syndrome. Not that it’s a bad thing but generally you’re the responsible one and you feel responsible for the world.

That definitely promotes leadership qualities because I was thinking at a very young age about my siblings, their well-being, how to get around angry adults and adults who are misbehaving basically. It made me grow up really fast.

Now, in some ways that was not a good thing because I missed out on a lot of sort of childhood naïveté and a lot of just sitting and watching cartoons or whatever my fantasy of it would have been. But it made me a somewhat serious person.

It also made me a person who’s been a caretaker and a sensitive person because I was around a lot of people with different emotions. I had to kind of learn how to be a people pleaser and bridge different personalities.

I think all of those things are really helpful when you’re a leader in business. One of the big challenges is just when your staff grows and you have a big staff and there’s so many people and personalities and being a person who’s navigated a lot of difficult personalities.

That was something that I ended up getting a lot of strength from. Even though I had a tough childhood in many respects, I think it made me strong and I took good things from it, even though it was not always fun.

Shubha K. Chakravarthy: I love that explanation and that just prompted a thought which is, you talked earlier about being very conscious and intentional about moving towards what you love and away from what you don’t love.

I’m just curious if this forced growing up in some sense made you more sensitive to the value and the preciousness of finding that joy in your life. I’m just curious if you had any thoughts on whether that might have been a contributing factor towards your maybe lower tolerance for things that don’t make you happy.

Lynda Weinmann: Yeah, I think there could be a connection there. I’ve never thought about it too deeply. I don’t have a lot of commentary on it but I think yeah, probably.

Pursuing Passion and Self-Motivation

Shubha K. Chakravarthy: So, the other thread and I’ve done a bunch of research on you. You’re my role model. I have to tell you that. One other thread that I saw as I was doing my research is this kind of love of learning, right?

You talked about the Mac. How you love the Mac and cracking graphic design and kind of the other piece was obviously this love, passion and commitment towards doing things a better way.

I’m just curious about how did you get clarity into these passions and strengths over the course of time? Was there a point at which you kind of decided to lean in consciously into those strengths? I’m just curious how that played out.

Lynda Weinmann: Early on, I was miserable in school. I had such a difficult childhood that I was in my head. I wasn’t in school. I wasn’t able to be very present to learn in a traditional way. I had a lot of inner dialogue, I guess.

When I was a teenager, I hated school so much. Someone told me about a book and it’s out of print but it’s called Summer Hill. It was about this idyllic school in England where kids were allowed to study what they wanted. There were no prerequisites. There was no forcing you into taking math if you didn’t like math or science or whatever.

I just thought this was such a revolutionary idea. I loved the description of this that fostered in people and kids, a desire to learn out of a true authentic desire rather than a forced desire to get a good grade or to please a teacher’s internal motivation which I think is far more precious and difficult to find.

I was very determined to go to a school like this. There were these schools popping up that were private and my parents didn’t have a lot of money but I wanted to go so badly. This probably says a little bit about me that I got a job at a hot dog stand and I earned minimum wage which was very little.

I know it will be different in India. Just the numbers won’t make any sense, that’s just a pittance basically. I went to the headmaster of this private school and said, “I make this much money a month. Can I pay for school? My parents can’t afford it.” And he said yes. He let me in.

I was the only student there that was paying my own way in high school. Now this high school was so unruly and unorthodox. When I look back on it, I have this idealistic memory of it that helped me learn how to be self-motivated and how to foster my own authentic interests and passions.

But when I actually look back at what it was, completely unsupervised, very unqualified teachers, no really important instruction in any way. The gift of it was the freedom to not take subjects that I didn’t want to take. I literally threw pots for almost an entire year. That was the only thing I did.

Are there missing parts of my education? I can guarantee it. But what I did get to do was practice this philosophy of going towards what you love at a very young age. I just found that as I grew older and I also went to a college that was unorthodox, Evergreen State College.

You’re allowed to create your own curriculum. And I did. For an entire year, I ran the art gallery and I took women in business course. I worked just directly under the Dean and had my own study that I had created myself.

I think that did for me set the groundwork for a life of self-motivation and a life of pursuing things that were interesting to me and lifelong learning like you said.

Shubha K. Chakravarthy: That kind of helped you craft a path that was very non-traditional and unpredictable. They couldn’t have foreseen it, right? And ended up in a beautiful place, at least, as I see it.

Freedom-Oriented Approach to Teaching

Lynda Weinmann: I’m jumping ahead but when lynda.com was being conceived and in the beginning, I just taught in this way. When I was teaching, you know, I was very lucky. I got a job at an art college that wanted to hire working professionals, not professional teachers.

It was an unorthodox art college as well. I got a job teaching there and I was able in the way I taught my students to give them open-ended assignments, a lot of agency and not really dictate how they did things and be kind of practice the same way of teaching and of being.

But when we created lynda.com and ultimately lynda.com became a library of videos. The library is a very similar approach to just here’s all this information. We’re trusting you to learn what you came to learn. We’re not telling you how to learn it.

If you don’t pass this test, you can’t get to the next branch of this learning. It wasn’t certifying that you can’t do that with every, you can’t do this with teaching somebody to do brain surgery. You have to have a way more rigorous curriculum but for the types of subjects that we taught, there was a lot of freedom for the learner.

That was all based on this early experience with the book Summer Hill and the unorthodox high school that I went to and then college and then the life that I led.

Shubha K. Chakravarthy: Love it. And was there one thing that guided you in terms of the outcome that you wanted them to experience? What was that thing that kept you knowing that you were on the right track versus not veering off?

Lynda Weinmann: Well, you really don’t know. I did get a lot of feedback from my students. I knew I was a very popular teacher. And I just hopefully a little bit of this special sauce rubbed off on other people.

Shubha K. Chakravarthy: And if you had to characterize the secret sauce, like, what would you say your secret sauce?

Lynda Weinmann: It just was freedom, the freedom to and acceptance. I really tried not to be judgmental to myself. The judgment that I was making over my students was, are you working harder? Are you not? Are you pushing yourself to try new things, do new things or not?

It wasn’t so much, did they learn this one fact or did they make this outstanding project in the end? Again, it’s more of a focus on the journey. Are they growing? Is this helping them grow?

And I think that is the most gratifying thing about being a teacher is seeing in the end where they were in the beginning and then where they are in the end and feeling some sense of involvement in that. They’re doing the work but it’s definitely a wonderful feeling if you like that sort of thing.

Role of Personal Relationships

Shubha K. Chakravarthy: Process over outcome, right? I love that. And just something that you mentioned also triggered one other thought about lynda.com. Again, I’m jumping ahead but I want to bring this up since it’s appropriate.

As a woman, lynda.com was obviously a huge part of your journey. You married Bruce and then that kind of everything came together. That just sparked a thought in my head when I know that for women, at least who you marry or who you end up with as a significant other or spouse can have a much bigger impact than it does for men.

I’m just curious, like how did you learn to navigate that? What were the learnings? You had a professional side and you had a personal side. And in this case, they were both intermingled together. I’m just curious how that played out as well.

Lynda Weinmann: I think I followed the same philosophy in my relationships as I did in my career. Just go towards the people that make me feel good.

I was married before I married Bruce and I think I’ve just always been drawn towards artists. My first husband was an artist. Bruce is an artist. I realize now that I’ve become an artist that the thing that I love about art is the problem-solving side of it. The idea that there are no real rules except for the rules that you impose on yourself. Then you can break those rules.

It’s a lot of moving target problem solving which is probably my favorite kind where there’s no one right answer. I’ve always been drawn towards men who thought that way. I’m still close with my ex-husband. Very lucky, so close to this family and he actually is very good friends with my current husband, Bruce.

So we have a wonderful extended family and it absolutely changed my life and my career to have been married to Bruce. But he was the first boyfriend or partner that I ever collaborated with in a career way. That was a surprising outcome.

I don’t think it was something going into the relationship that either of us planned. But we were sort of one of those power couples that together we equal more than we do separately.

Shubha K. Chakravarthy: You had a very strong artistic strength, right? Both of you had a very strong artistic strength and artistic side.

Lynda Weinmann: No, he was always the artist. I was intimidated to be an artist because he was so good. That was one of the big hurdles for me deciding to become an artist that I had to get over was comparing myself to him which is a big hurdle that most artists have to get over comparing themselves to other people. It’s actually a big part of becoming an artist. But he was always the more artistic partner in the partnership.

Shubha K. Chakravarthy: And how would you characterize in that context, how would you characterize kind of your strength versus the artist’s strength in him?

Lynda Weinmann: He’s a dreamer and he’s like the idea factory. He’ll come up with like 1,000 ideas and a few of them are real gems but not all of them. I’m probably the more pragmatic of the two and the more grounded. Also, I think because Bruce is on the spectrum of Autism and I’m a normie, I’m very good at socializing and always have been.

That’s been one of my special powers just to get along with all kinds of people and things like that. I was in many ways a conduit to a world that he might not have connected to without a conduit. He was absolutely a conduit for me as well because of his incredible creativity and also the strategy.

He was always the big strategizer in the company. I would have happily written books and taught and not ever thought to have expanded it into a video library or a company or any of the things that he pushed towards. He was pushing me the entire way to take bigger risks than I was probably wired to take.

I was probably reining him in because he could take such big risks that maybe he wouldn’t have worked out or it’s hard to say. But he’s a really amazing mind and a creative problem solver. So that I have benefited greatly.

Shubha K. Chakravarthy: That’s fascinating. It’s not what I would have expected you to say. That’s a good insight. So then, which brings us to this.

You’re the pragmatic person and you have the skills. He’s the thinker and then you come together in this mix. You’re teaching, like, where does this idea come from? What’s the spark and what’s the motivating factor for you?

Lynda Weinmann: An evolution, it was never one idea. It was never thought out from the very start. It was again being on a journey adapting, I started as a classroom teacher.

I met Bruce. He was my student actually. We never dated when he was my student but we got to know each other when he was my student. I then wrote a book that became a national international bestseller on web design. It was one of the first books on web design which I was just getting to know Bruce at the time. He was helping me with some research.

I’d sort of gotten to know him outside of school and he had been extremely helpful in helping me with research with my book. Then the book was really successful. Then our relationship took off. We got married. When we first were married, we were living off book royalties. And that was our income.

It was his idea to start a classroom of our own. A kind of a private trade school to learn web design. We started in a very noncommittal way. This was his idea to rent a local high school’s computer lab for spring break when school was out and offer classes on the new internet.

Somebody came from Vienna, Austria, which pretty much blew our minds because it’s the very beginning of the Internet. It’s international but you don’t realize you’re going to, you’re going to publicize a class and someone’s going to come from another country. You just don’t realize the power of it.

So that success gave us the encouragement to rent a space and start an ongoing classroom. Then that was very successful and I was still writing books and I hadn’t even started recording videos yet. And then 9/11 happened, which was the twin towers and the big attack that we had in the US.

Then people stopped traveling and our business dried up. We had to figure out another way. It was really a little bit out of adaptation to how do we stay alive to think about publishing our own materials which ended up being to publish videos at the time VHS cassettes. That doesn’t even exist anymore.

Putting the videos online was also another huge risk and nobody had done that. All of our competitors were selling physical VHS tapes. We’ve created this library idea. You subscribe and it was very early on in subscription businesses. There were so few of them.

Today there’s subscription fatigue. Everything is a subscription. But back then, nothing was a subscription. We just pioneered a lot of things out of adapting to our circumstances. It was not a big master plan that was going to lead to selling our company ever.

Adapting to Challenges and Growth

Shubha K. Chakravarthy: It’s easy in retrospect to write your story and say that this is how it worked out and look, there are all these forks in the road and we took the right fork but as you are living in the day to day, right? You have the next decision come up. Should I be even creating a video? It’s painful. It’s very uncertain.

You don’t know if anybody’s going to buy it. What was the metric, what was the rule you used to say that this is how I’m going to decide, what did you use? Then were there things that didn’t pan out and how did you react to those? I’m just curious about that process.

Lynda Weinmann: Well, absolutely. We’re just not a typical startup at all in that. We never took that. We never even sought investment. We bankrolled our own company from book proceeds. We were making royalties on the books and that was what we reinvested in starting a classroom and starting a video publishing company.

We were not ever really even aware of some of the things that you learn in business school and metrics. But we were looking at our own metric. Our own metric was, can we pay our bills? Can we pay our employees? When the attack came, it really changed our travel in our country. It pushed a lot more people probably towards online.

It had a really enormous impact, definitely on us. We had to adapt or die. We had to lay off. We were 35 people just from our live classroom business. We had 35 employees and we had to lay off 17 of them. We did it all in one day. It was really awful.

But had we not done it, we wouldn’t have ever survived and been able to do the next thing. Those are all really tough business decisions that you have to make at the time. But if you don’t make them, you won’t have a business. It’s just very black and white. It’s your own survival, I guess. That makes you act unless you’re self-sabotaging or something which some people are.

Shubha K. Chakravarthy: Is it fair to say that you start off in a certain path. You’re driven by the art or the skill of teaching people how to do web design. You experiment with a few things.

Is it fair to say that by this time, 9/11 happens and you’re pretty much running a well-sustained business as challenging as it is? Have you transitioned at this point to like a business person? How would you look at that evolution yourself?

Lynda Weinmann: I think both my husband and I were business people but we were unorthodox business people. We also cared about art and I think almost anybody who worked for us in the early days would tell you that we were just really great employers and cared a lot about our employees. We just believed we could do this the way we could chart our own course.

I don’t know what gave us that confidence but it was helpful to have each other. That was to have a partnership that isn’t just a business partnership. It’s also a marriage. There’s a little bit more. I know plenty of marriages probably fall apart as business partners but there’s probably just a little more impetus to hold it together, even when you disagree.

I think that we disagreed plenty but we were absolutely looking at our bank account, looking at if we could afford to do the next thing. Then when we got big enough, we started to hire business managers and eventually we hired a CEO and we hired people, a CEO, a COO, CFO etc.

When you get into the C-level stuff in the beginning, we were so small. We didn’t have all the hierarchy but we did not see our core strength as number crunchers and sort of MBA-style business people. We’re very down-to-earth and just driven to run our business the way that felt right to us and sort of matched our values and matched our goals.

Shubha K. Chakravarthy: This point that you mentioned of hiring like professional help so to speak at the C-level, it’s a very big transition point, right? Because until now, you’re the boss, you decide what’s right.

Then suddenly, even though they’re reporting to you, it’s still a different dynamic. How did you transition through that? What was your guiding principle? What kept you through and what kept you focused?

Lynda Weinmann: We’ve really lucked out in many ways. We were actually interviewing our CEO as an advisor because we had so many companies and investors sort of knocking our door down. I guess when you hit a certain revenue number and you’re a small business, I think it’s 10 million revenue a year.

Suddenly the phone was just ringing off the hook and all these different offers. We want to give you a valuation and we want to invest in you. So this guy was actually a business consultant and he was somebody we were thinking he would just guide us through this dilemma. After hearing our story, he said, “I’ve evaluated thousands of businesses. I’ve never really encountered one with as much potential as yours. I don’t think you should take money but I think you should hire a professional CEO and I’d like to volunteer myself.”

It could have not worked out but it did work out very well for many years. You said the CEO is reporting to you and you’re the CEO’s boss and that is exactly right. That kind of kept it following our values and following our strategies and everything even though he definitely had a huge hand in expanding the business and helping us navigate all kinds of things.

The Impact of Investors: Losing Control

Lynda Weinmann: But then when we did ultimately take on investors and then he was beholden to them. That’s how he viewed it, not beholden to us. I think you’ll talk to any founder who’s been through that process and it’s founder syndrome where suddenly you’re not in control even though you’ve kept the controlling.

We had kept the controlling shares and really didn’t realize when we took on our first investors that we were going to lose control over our CEO. And you know, really his goal at that moment, once we had investors was to have a spectacular outcome. Either go public or sell the company.

That became the driving force that had never been the driving force of our company. It really changed the ethos and the entire organization. It was very hard on myself and Bruce because I just don’t think we had seen that coming even though we probably should have.

We knew when we took on investment that they’re not doing it out of kindness. This means you’re going to have an exit but we didn’t realize it was going to mean that we lost control and we did. It wasn’t fun but no one was going to cry us a river.

We had a company sold for a spectacular amount of money. We were able to move on to our next chapters and it was very clean. As much as we didn’t enjoy the process, our outcome almost couldn’t have been any more ideal. You just have to sort of take it all.

You’re very attached like your business is your baby and especially when you’ve been running it for almost 20 years which is how long we had run lynda.com. It was a super hard and emotional transition to sell and go on. I would say we’re in a really good place now but those were some hard moments.

Shubha K. Chakravarthy: Were you ever tempted right at that point, you’ve taken on the investors and one day you wake up and realize that decision X is no longer yours, right?

So hiring some new person whatever. At that moment or in the months following, were you ever tempted to second guess? Maybe we shouldn’t have done this. Maybe there’s a different path. And if so, how did you navigate that?

Lynda Weinmann: Yeah, at the time I had regret that we had put someone in the position of CEO but when I really look back on it, he helped us. There’s just absolutely no way we would have grown the way we did without his expertise. It was very compatible, friendly and really magical for many years.

Everything worked out the way it was supposed to but it doesn’t mean it was all fun and pretty. That’s probably the story of every company that sells and we tend to romanticize times. Memory is an odd thing. Just like I was saying about the school, I had this romanticized view of the school that I went to but realized I got together with some of my classmates about 10 years ago. We were all comparing notes and we were being raised by wolves. This was actually not okay. We were actually in danger. How did our parents let us do this?

Our memory is kind of tainted. Again, with my philosophy of trying to be very much in the present. Forgiveness is a big part of that with empathy and understanding. Everybody just kind of did in hindsight.

I don’t agree with the decisions that he was making. I didn’t like the way it happened. It just didn’t end well unfortunately. But I can’t really hold that much fault for anything that happened or regret because it all turned out the way it was really supposed to.

Shubha K. Chakravarthy: So if today’s Lynda had to set the earlier pre-CEO Lynda aside and have a little talk with her, what would you tell her today?

Lynda Weinmann: Oh, I don’t know because I don’t think I was cut out to be the CEO. There would have been a time where I would have answered that. I would have never hired a CEO but I wouldn’t answer it that way now.

I actually think things worked out the way they were supposed to. We were sheltered from a lot of the parts of business that neither of us would enjoy. We were sheltered because we created a company that was successful enough where we could hire the people to do the things that we weren’t good at. We didn’t want to do it.

It’s not like we were sheltered by some magic potions. We created the sheltering on purpose because that’s what you really should do. You should do the things that you want to do and you’re good at. And let other people who want to do those other things and are good at those other things, do those things. So that’s the way, ideally, the world works best.

Shubha K. Chakravarthy: It sounds like it turned out to be a good thing that you didn’t know what you didn’t know.

Lynda Weinmann: It’s a little bit like my childhood. Would I have wished that I went to live with my grandparents for a year, that I didn’t get to live with my mom when I missed her.

All these things, I have a stepmother who I didn’t get along with in the beginning and at the time I would have wanted to change all of those things. But when I look at the story of my life and how every single thing was a building block that brought me to the next level as a human and allowed me to evolve as well as improve, I don’t regret any of it.

Shubha K. Chakravarthy: I’m just curious. Do you think it’s possible for a founder like you to remain friends with a professional CEO?

Lynda Weinmann: I think it’s possible. I have a whole different life now and a whole other chapter but I don’t blame. I don’t harbor resentment. I really do not. I believe that resentment is poison.

I think to have that in your body is not a healthy thing. I always kind of strive to figure out a way where I can hold in my heart, forgiveness, empathy, kindness and love. Those are the things that are important in the world.

Shubha K. Chakravarthy: If a founder is in a position where she might need to hire the CEO from your experiences, what forward-looking counsel would you give to smooth that transition?

Lynda Weinmann: If you’re the CEO’s boss, that’s one dynamic. If you bring on investors, it will be a different dynamic. The CEO will report to the investors. I didn’t know that.

Even though you would call me an entrepreneur. I would call myself an entrepreneur. I had no education to be an entrepreneur nor did my husband. We winged it the entire way. So all I would say is just go in with your eyes open.

When you take on investment, you are going to lose control ultimately whether you do in the very beginning or you do towards the very end. The decision is that you’re going to let your company be either sold or you’re going to go public. You’re going to ultimately lose control. That is the decision.

Shubha K. Chakravarthy: Is that something that happened gradually or was that like a flip the switch moment where you realized that today is not yesterday and “We’re not in Kansas anymore” so to speak?

Lynda Weinmann: Yeah, it’s maybe a little bit gradual but not very. You know, pretty obvious. It gets to you pretty quickly.

Shubha K. Chakravarthy: One other thing, you brought up this issue of values and how you would have chosen or made choices versus somebody who’s driven by investors’ interests and so forth.

I’m just curious to understand personal values and how they play into your journey. What do you consider your top values? What are the sort of the non-negotiables and how have they shaped your entrepreneurial and professional journey?

Lynda Weinmann: That is a loaded question. I shared some of my values in the last conversation but one of the things that I loved about lynda.com was that it was open-ended.

It was very much this idea that you entrust your customer to know why they’ve come to go where they want to go. And yes, at times they might want some guidance. I don’t even know the first thing about web design, where should I begin? That sort of thing is very helpful. But there were so many online.

At the time online education just meant something completely different. It meant that you were going down these little pathways and they had been predetermined for you. That’s how a lot of in-person education is too. It’s very prescriptive.

So it was super important to me that lynda.com be this library where you could serendipitously go into a physical library and you’re pulling out a book. It’s on history and to the right of it is costume design. You’re like “Oh, that looks interesting too.” It’s related to history and you go to something adjacent that you weren’t expecting. You’re stumbling on it. It’s sort of natural and I wanted the library to be like that. The way that the library was envisioned was maybe a little special in that regard. So that was important to me.

It was important to me how we treated people. Bruce and I both came into being business owners from being gig workers basically. Neither of us had really had full-time jobs. We had done a lot of different kinds of things. I’ll work for this much per hour for a month doing this and then I’ll do this other thing.

He worked for Disney and they were yanking his chain. It’s an expression just to pay him this pittance for them. They’re a giant corporation. From 90 days to 120 days, just stretching out this payment. Meanwhile, he’s trying to pay his rent. We knew that a lot of our instructors were the same and a lot of our vendors were the same.

So we sort of made this philosophy. If we can afford to, we’re going to pay everybody’s bills when we get the invoice. We’re not going to wait 30 days. We’re not going to game the system. We had always done that.

It was actually a great business strategy because if you pay a legal bill faster than the next customer there, next time if you have a problem they’re going to give you some preferential treatment. It’s just smart business. If you want people to want to work with you, you treat them right. You pay them fast. You do things. That was a philosophy.

When we took on investors, we got a CFO. All of a sudden we’re paying our bills 90 days or 120 days. We’re getting people writing to us personally. You’ve always paid quickly. Like what’s happening?

This is all to make the books look a little better. At that moment, that’s what investors think about. That’s the entire mindset of how do you make the profit look bigger. How do you make it look like you’re doing even better than you are? It was just so sad because our business was very successful and we didn’t have to do it that way. That had never been the way we did it before. It was against our culture. It really kind of hurt our hearts.

But on the other hand, we’re naive sort of non-MBA types. There were lots of profits that we gave to other people because we just felt like we didn’t need them. For example, we would give outrageous holiday gifts. We’d have a good year, we’d give every employer a laptop. We did that and nobody does that.

That would have been money Bruce and I could have put in our personal pocket and we didn’t. It just felt really good to us to treat people right. It made the whole experience so fun and so loving. This idea of generosity is like generosity of knowledge and we’re sharing with you in the good times.

When bad times unfortunately we have to lay off 17 people in a day. But when you’re having good times I would say, if you’re not going to do these things during good times, when are you going to do them? How are people going to really believe you when it’s a bad time?

But this is the sad thing about our world. It’s just the profit, just being the primary goal and not really thinking about quality, not really thinking about interactions and how people interact with your company.

It’s like a 360 thing. It’s your staff. It’s your customers. It’s your vendor. It’s your administration. It’s above, below, to the side, to the right and to the left. It’s everything you have to walk the walk or people you’re not going to be believed.

Shubha K. Chakravarthy: Listening to you, I get the sense that first of all that you wouldn’t do anything different if you had to go back and redo it is the sense I get.

The other sense I got as I was listening to you was that that value system infused or contributed to a lot of the joy that you felt. That you talked about earlier, you said, “Hey if it feels good, I’m going to do it.” And it sounds to me like this was like one of the threads of what that experience was. Is that a fair statement?

Lynda Weinmann: I think it’s very fair.

Defining Success Beyond Wealth

Shubha K. Chakravarthy: That brings me to the question of success, right? You talked about success and is it profit? Is it wealth? How has your view of success evolved over time? What was it starting out and what would you say? It is today. And what has driven that evolution over time?

Lynda Weinmann: That is such a big good question. I feel successful because I like the life I’m leading. I feel that I am being good to the people in my life that I want to be good to. I’m making the world a better place than I found it. I’m always learning new things.

I’m personally activated and have personal happiness. I don’t worry about earning a living. I’m retired. We’ve been able to be philanthropic and support many causes. But success is such a loaded word. In some ways, it’s a word that sounds like you’re succeeding over other people. There’s something about it that’s hierarchical that I don’t love.

But having witnessed people dying and at death, the things that matter to you are not how much money you have in the bank or how many possessions you own. It’s if you live a good life. Did you do the things you wanted to do? Were you good to the people that you wanted to be good to? Did you foster the relationships you want? Are you loved? Did you put love out?

Obviously I don’t have a written list of what these measures of success are but I know that real success just has nothing to do with selling your company or being wealthy or anything to do with money whatsoever. It doesn’t hurt.

Of course, it’s a wonderful privilege to have financial freedom. It’s a wonderful privilege. I’m not saying there’s anything at all wrong with it. I’m very happy to have it. I’m grateful to have it. But I’m not sure that it’s the measure of success at all.

Advice for Aspiring Women Entrepreneurs

Shubha K. Chakravarthy: I love that. The one thought that prompted me, especially as for myself and for other women, right? There’s this tension between being wealthy, successful and being a woman. You’ve kind of been all three. From the perspective of looking back, how would you recommend that women handle this especially if you’re starting a business?

You want to create an impact, make a difference but you don’t want to be naive about handing. I get the point about generosity and I completely take that point. Keeping that in mind, what’s your thought and what’s your perspective on how wealth plays a role, especially for a woman starting out? How should she think about it? What are some things you’ve learned or observed over the course of your journey?

Lynda Weinmann: I don’t know that I’ve really given that ever any thought and that I have an answer for you. I definitely would not call it wealth. I would call it confidence.

I would say that when you’re starting off, you have to fake confidence before you have it because you’re not going to walk in having wealth. You’re not going to walk in the door having monetary success. There are many other things that you need to have but one of them is confidence in your ideas.

I think maybe that’s something I’ve always been good at is sort of faking confidence before I had it. They call it fake it till you make it. I used to think that I’m just to have this memory of when I was just out of college and kind of struggling in my thirties.

I used to think that if I woke up and I was feeling really down, I’m just going to really get dressed up and kind of fake that I feel good and really try to put forward a better appearance than how I’m feeling inside. I don’t know why I had that instinct but I do think that women have to.

What I have observed in my own career and I hope it’s not as true as it once was is that I’ve always felt like I had to be better at men. Better than a man to even be at the level playing field. Especially being a woman in tech in the early days, I felt like I had to dazzle and impress them with my knowledge.

Not just be knowledgeable, not just be on the sidelines but really demonstrate that I understood the language, what the concepts were and what was at stake. I think that confidence also was really fostered by the unorthodox education that I had because I found at least our schools in the U S have become very rote.

And really focused on test taking and what your test scores are. And everything about that. The carrot is the test score versus the knowledge. Just like the carrot is the wealth versus or this thing of success versus making something that’s sustainable, actually works, is good for others, helping and somehow benefiting others.

For me, the thing that I would advocate is to build confidence. I actually had a few women in our company that I suggested who to me did not exude confidence. I suggested maybe you should practice going to a class in giving a speech or in communication and pitching or something. It’s very important to present yourself with confidence. I don’t know, maybe that’s my answer.

Shubha K. Chakravarthy: How did that work out? I love it. I love your take. How did that work out for them?

Lynda Weinmann: A lot of them didn’t take my advice, sadly. Maybe it’s not sad. Maybe it just takes all kinds of people in the world and some are timid, some are daring, some follow and some lead.

It takes everybody to make this whole thing work. Maybe it’s not a bad thing. Maybe we don’t all have to be confident. It’s just finding where you fit and that makes you happy and you feel like you’re contributing and you’re good at it.

Legacy and Life After Business

Shubha K. Chakravarthy: Which brings me to the question of legacy, right? Looking back, clearly you’ve added a lot in terms of learning contribution to the world and so on.

How do you think about legacy and how have your thoughts evolved in terms of like at least all the women founders that I’ve met, there’s some technological innovation, whatever the case might be.

But at the core everybody wants to make an impact, right? Everybody wants to make the world a better place. I’m just curious how you’ve thought about that impact over the course of time and how you think about it today.

Lynda Weinmann: Today I don’t think about it at all. I feel like I made my impact and I am still making an impact in my own way. I have become a full-time artist. I’ve been learning bridge which is extremely hard. I have an aging parent. I have responsibilities. I have my child. Even though she’s grown, she has a lot of health challenges and I’m there for her.

I just kind of have a big life that I’m balancing and I’m doing my best. My husband created a piece of monumental architecture. We live in a house that he designed with an architect and I think it will become a legacy for him and maybe for us and then it will last beyond us.

But already people don’t even know what lynda.com is. It doesn’t exist anymore. I think this experience of having watched people die. When we’re gone, we’re gone. All the people who were rich and famous in the 1700s, we barely know who they are.

300 years from now, no one’s going to know who I am. Nobody’s going to know what I did. And to me, it doesn’t matter. I don’t care. I don’t need them to know.

Shubha K. Chakravarthy: I love it. There’s real wisdom in there, for me and for a lot of us.

Final Thoughts and Words of Wisdom

Shubha K. Chakravarthy: So on a concluding note, what would you say to other women who maybe are a younger version of you who are burning up with, I don’t want to say ambition, but a desire?

Lynda Weinmann: Yeah, I was burning up with ambition. I definitely am.

Shubha K. Chakravarthy: Fantastic. I love it. Then what words of wisdom would you leave us with?

Lynda Weinmann: It’s a journey, not a destination.

Shubha K. Chakravarthy: And your guide when you wake up in the morning, how would you suggest? I wake up in the morning and do what?

Lynda Weinmann: Gratitude.

Shubha K. Chakravarthy: I love it. Is there anything that we should have talked about that you would have loved to talk about that we didn’t bring up?

Lynda Weinmann: No. I think this was a great conversation. Thank you so much.

Shubha K. Chakravarthy: This has been amazing. I have learned a lot and I know that many other women will. I really appreciate your generosity and taking the time to do this.

Lynda Weinmann: Thank you. You asked great questions. It was really wonderful to get to know you and be on your show.