Syama Bunten: I am here today with the fabulous Wendy Ryan. Wendy, your beautiful smile shines so deeply through the screen. I am so grateful to have you ladies. Wendy Ryan is a board advisor, angel investor, bestselling author of Learn Lead Lift. She’s also featured and show her the money for her work championing women founders, Wendy, you are prolific.

Syama Bunten: You are known within the community for the ways in which you show up with integrity. I am so honored to have you share your story today on getting Rich together. Thank you for being here.

Wendy Ryan: Oh, thanks for having me. I’m thrilled.

Syama Bunten: Yeah. Oh my God. So before you were looking fabulous with your hair done beautifully and lovely lipstick.

Syama Bunten: You were once a little girl who probably knew nothing about how to do her hair and maybe about lipstick or maybe you did, I don’t know, 10, 12 years old. I feel like I definitely wanted lipstick, but I was still wearing like, remember that Red Chapstick, you know?

Wendy Ryan: Oh yeah. Putting a lot of smackers.

Syama Bunten: Yeah, I’m all the way.

Syama Bunten: I’m putting a lot of it on ’cause I really wanted some color. But Wendy, take us back to 10, 12 years old. Where were you in this beautiful world of ours? What was life like and what was money like?

Wendy Ryan: Yeah, so I had an interesting childhood in that I moved around several times between the age of two and the age of 14.

Wendy Ryan: So a couple of different geographies, but started out, you know, so I’ll have to go back a little further. Started out life in Wichita, Kansas, uh, where, where I was born and I lived till I was two. And then we moved to Fountain Valley, which is those of your listeners who are from the LA area may recognize that’s in that metropolis.

Wendy Ryan: Uh, and then ended up in Madison, Wisconsin for a few years and then ended up in Saratoga, California, which is one of the suburbs of Silicon Valley. And so when I was 10 or 12, 10 to 12, that’s where we were living, was in Saratoga. And we were a middle to upper middle class in the socioeconomic ladder family.

Wendy Ryan: And we, you know, always had kind of what we needed, but I remember. There being some tension around money because my mom worked full-time as a nurse, anes anesthetist. My dad also worked, but he had, he had a little bit of trouble holding down the same job for a long period of time. So I think there was some tension around who was making money when and for whom.

Wendy Ryan: And when I was 12, my parents decided it was time to separate and then it ended up divorcing.

Syama Bunten: Wow. You know, I feel like early modeling of divorcing can also be just quite powerful. I know it’s very traumatic, but also to, to like, I don’t know, to be out of something that no longer serves you. You know, when I was little, my mother.

Syama Bunten: And father, they divorced when I was five and then they got back together when I was nine. And I remember being like, I don’t know if this is a good idea. You know, like, it’s like you’re like, there’s a reason why you’re not together. And um, and it’s so interesting I think as young people to think about like, what are we responsible for?

Syama Bunten: How does this impact us? So as you were kind of experiencing not only being some, somewhat having lived in different cities, which obviously insinuates that you had to learn how to make friends a lot of the time retell your story of like, hi, I’m Wendy, like this is, you know, this is who I am. But then also divorce hits, and then there’s this whole other third thing that comes in.

Syama Bunten: So how did you kind of navigate that divorce and, and what was that like for you and how did you see your parents model decisions and what were some of those money signals?

Wendy Ryan: Yeah, I think as happens to so many families, we were in a situation where the house that we were living in was going to need to be sold as part of dividing the assets.

Wendy Ryan: And I think that was, I remember very distinctly seeing how stressed my mom was about that. I think she was starting to look at condos and where was she gonna live? And I remember one day she broke down in tears and was just crying and I couldn’t understand why. And now in hindsight I get it, you know, she was mourning the loss of the American dream, if you will, of home, home ownership.

Wendy Ryan: And now feeling like she was taking, you know, a big step back. And that was, rightly or wrongly, that was really hard for her. And so I think that was informative for me as far as understanding, oh, you know, people really care about things like. Owning a home. People really care about this sense of forward momentum, and we’re supposed to somehow be moving towards something bigger and better and not going the other direction.

Wendy Ryan: So I remember that, that really, that really made an impact.

Syama Bunten: You know, I think it’s interesting now to think about this idea of, you know, what does having a home mean? You know, I know so many young people today are questioning what that is, but certainly for your mother, that would’ve been smack dab. And also for us, right?

Syama Bunten: Smack dab in the middle of this is what building the dream is for. Right? It’s for

Wendy Ryan: right

Syama Bunten: for these walls, right. For a sense of security. And, and to have that no longer be there means things feel less secure. Right? Like, what can you,

Wendy Ryan: yeah.

Syama Bunten: What can you count on?

Wendy Ryan: So I’m sure at the time, the combination of feeling like her family was dissolving and home ownership was dissolving was just a lot.

Wendy Ryan: And even though she had a job. She could support herself. It was also scary. It was scary to do that with two children because my father was not reliable in terms of a source of income. So I think that pressure and that uncertainty was, was certainly something that impacted her.

Syama Bunten: Hmm. What kind of impacts did this have in your high school years?

Syama Bunten: Was it, okay, I’m gonna work really hard you know, what’s happening to my mom is not gonna happen to me and I’m gonna like double down on this stuff? Like, was it a bunch of, was it a fear cue to like safety and protectionism? Or was it like, okay, we need to carve out this entrepreneurial vision?

Syama Bunten: Like how did you start to internalize and express, like what was going on around you in terms of who you thought you were and what you thought you needed to be and do?

Wendy Ryan: Yeah. So the, this is one of the first of several twists, plot twists in my story, where as soon as my parents decided to separate, my mom went out on a date, so like a month later, and she was set up on a blind date and she happened to be set up with someone who she would instantly recognize was the true love of her life.

Wendy Ryan: And his name was Dan. And they married one month after my parents’ divorce was finalized.

Syama Bunten: Wow. Wow.

Wendy Ryan: So, oh my God.

Syama Bunten: I’m like, cool for her. And how did you feel? You could imagine that’s a whole nother episode, right? And a whole nother podcast on dealing with, uh, changing family dynamics when you’re a, a preteen, so to speak, an early teenager.

Wendy Ryan: It’s a really interesting time for all that to happen. But she the moral of the story, I guess, or the bottom line is she didn’t have to go live in that condo. So she sold that house, and we moved at that time to Los Altos because Dan happened to be wealthy. So that was interesting because mom almost didn’t marry him because she was very concerned about the fact that he earned more money and had more assets than she did.

Wendy Ryan: And she was very worried about the power. Dise the disequilibrium of that, which again, is something that in hindsight I learned and heard and understood more about. But she was so in love. They were so in love and they really were perfect for each other. They ended up being married for almost 30 years until she died.

Wendy Ryan: So the so it was kind of like they were destined to be together and my mom just had to get over whatever issues were in the way, whether it was money or, you know, what are other people gonna think? ’cause I like just got divorced and five seconds later I’m married again. It’s like she kind of had to put all that aside and just, and just follow where the heart was leading so powerfully.

Wendy Ryan: And I think that was both beautiful, but also I’m sure concerning for a lot of people around her.

Syama Bunten: Yeah. And also like, go mom, you know, it’s, it’s really, it’s difficult to hold space, I think, for our own decisions to have things make sense to ourselves, especially when what our heart tells us may not be logical, right.

Syama Bunten: And, and to double down on sort of the information that we receive inside of ourselves. And then to then, and this is the way the world works, unfortunately, but then everyone else seems to have an opinion. And so then it’s like, okay, so it’s hard enough for me to figure out my own shit, but then I have to like, explain myself to everyone else and I am still figuring out what I am doing on this planet.

Syama Bunten: So, yeah, I mean, I get that in, in a lot of different ways. And so when you were in high school, I guess, like things have now materially changed for you, right? It’s like, like you’ve had a very interesting. Life transformation of what you had very little to actually do with, right? It’s like these things are happening around you.

Syama Bunten: So how did you find a sense of control in your life? You know, what did that look like?

Wendy Ryan: Yeah. So I think to really illustrate how that felt in a tangible way. I remember very clearly during the divorce or leading up to the divorce do you remember, I don’t know if you ever had or your family ever had, but they were like these sleeping bags that you would wear and then all these snaps and they were kind of like slugs.

Wendy Ryan: And I think they came back a few years ago. There was some version of those that came back. We literally had those because my mom wa was like, we can’t afford to leave to like have the heat on all day. So we were, you know, in, in a fairly nice house in a nice neighborhood, but I remember going, oh, there’s a limit to what we can afford.

Wendy Ryan: So we went from that to then living in a very nice house in Los Altos near the country club. And it was like, we never had to again, where those snugly and my mom probably wanted to go burn them somewhere, I don’t know, have some sort of cleansing ceremony. But that, that was a real kind of tangible experience and it, it taught me a couple things.

Wendy Ryan: One is that what’s going on appearance wise is not always what’s going on behind the scenes. I, and I think that’s true for a lot of people. They’re, we think they’re doing well, but maybe they are making some sacrifices. And mind you. We never had like, not enough to eat or anything like that. So I cannot not acknowledge that.

Wendy Ryan: But these are the things that really stick with you, I think. And so when you asked me about how then I navigated money in high school, I was very motivated to work. I always felt like I wanted, I, I wanted to be independent, you know, I wanted to be able to support myself, rely on myself. And I think some of those experiences probably I’m hardwired that way to some extent, but I think some of those experiences really reinforced it, watching my mom kind of struggle and navigate different circumstances in a pretty short period of time.

Syama Bunten: That’s incredible. And so during those young years, as you were preparing yourself then to think about things like. University, right? Was it okay, I am gonna go study something that’s gonna guarantee me the job. Right? So if you’re going after security, it’s always, you know the false narrative is that the corporate man is the security.

Syama Bunten: But you know, that’s the thing that we’re all raised to think about, right? Is, is like, that’s what security is, at least when we’re younger. How did you start to think about what you wanted to study, what you wanted to be and how you would start to go about doing it? Because Los Altos is, is a beautiful area.

Syama Bunten: You’re close to Stanford, there are some really great schools and, and opportunities there. Um, but how did you start to think about exporting yourself into the world?

Wendy Ryan: I wish I had been more thoughtful about it at the time. So as you’re asking the question, I’m thinking. Yeah. Wouldn’t it have been good if I had been able to focus on that a little bit more?

Syama Bunten: Says no, 17-year-old, by the way, like no, 17-year-old is like, and then I thought strategically, actually, maybe not. Maybe there are, especially today. I think there are, but go ahead.

Wendy Ryan: Like, I was kind of bored in school, and so I started working at Nordstrom. There was a, a kind of an internship program through our high school.

Wendy Ryan: So I would go to school senior year for half the day, and then I would go and I would work half the day. And I just liked working. I wanted to work, I wanted to earn, I and I, I wasn’t really strategic in terms of thinking, well, what would be the best path to guarantee security? It was more like, and maybe this is a Midwest, you know, the, the Kansan in me coming out.

Wendy Ryan: But it’s like I’m just gonna work hard. It really doesn’t matter at what I’m just gonna I work and therefore I am okay. I understand that. I mean, that is like a, I feel like there were so many times in my life where I was like, as long as I know how to do something that’s of value, like I will always have that paycheck and uh, and that will help me feel secure.

Syama Bunten: As you found yourself, I mean, obviously and, and you know, working retail, I think some people underestimate the things you learn on the ground, right? And like what you figure out. And, and I remember just like thinking about the experiences in retail where, you know, you get to be responsible for such large volumes of, of money, right?

Syama Bunten: And like things are, are turning and you have such influence in so many ways no matter where you are, you know, in the, the labor chain of working in retail. But as you went to, to university then, like what did you end up studying and how did you sort of. Navigate the selection process of, um, your future alma mater.

Wendy Ryan: So I really didn’t have any idea what I wanted to do in high school, and I was really envious of my mom, who from the day she was born, always claimed I, I just wanted to be a nurse. Like that was just, I always wanted to be a nurse. Fortunately, that was one of the three choices that were actually on the menu for her, because when she grew up in the as a young woman coming of age in the fifties she was told very lovingly and sincerely by my grandfather, Kay, you can be anything you wanna be.

Wendy Ryan: You could be a teacher, you could be a secretary, or even a nurse. Fortunately, one of those was already kind of on her menu. Since that was apparently the extent of the menu. And so how that then evolved for, I think my mom and, and Dan at that point, my stepdad really stepped into the dad role full force.

Wendy Ryan: They said, you can do anything you wanna do. And they meant it both literally and figuratively because it was like, you can, we can afford, you can go wherever you wanna go to school. You can study whatever you wanna study. But that wasn’t actually very helpful because no one was looking at me and saying, you know what?

Wendy Ryan: You’re really good at this. Have you thought about that? You know, no one ever said, have you thought about being a CEO? Have you thought about being an investor someday or an educator? Any of those things. So I’m not sure. While I appreciate that the menu went from three courses to. Now it’s almost

unlimited.

Syama Bunten: Yeah, totally.

Wendy Ryan: There was no guidance with that. And I think it’s important for young people to, for us to be mirrors for our sons and daughters and the youth in our lives and to be able to notice things like, Hey, you know, when you said that thing or did that thing or gave that presentation, you did a really good job and here’s why.

Wendy Ryan: And to be specific. So I think that would’ve been helpful. And the proof I’m gonna cite for this is that I, I did go to uc Davis. I got in I, I’m not sure I would’ve gotten in now because things have changed a little bit. But I got in and I changed my major three times while I was there because I was still trying to figure out what my lane was and what I wanted to do.

Wendy Ryan: And I ultimately. Landed on psychology and Spanish because those were two things, frankly, that I found really easy for me and I enjoyed.

Syama Bunten: I love that. You know, it’s also interesting because some people study some things in college and then they never use those skills again. But you my love, have been implementing what you studied in school your whole

life.

Syama Bunten: It’s like, which is really incredible, right? To be like, some people are like, yeah, I didn’t need to study that. Never looked at it again. And you’re like, oh yeah, that college degree. Like it’s, I’ve been juicing it for all that it is worth. I love that. And so as you were starting to think then, you know, obviously there’s this interesting point I think of, of contrast, right? When you know that you’re family. Has a, like in your young mind unlimited resources though, they would probably not say that, but you know, in your young mind it’s like, I can, you know, do anything or can you help with this?

Syama Bunten: Or is there this like, you know, I think that there are constraints that are oftentimes self-imposed constraints. There are constraints that are imposed by others. And there are stories and things that sort of define how we think about ourselves, regardless of like our financial situation. Right. And, and I think that our young needs to sort of prove ourselves is probably one of those, right?

Syama Bunten: Like, I’m gonna prove that I can fill in the blank as you are graduating. College and starting to think about working and like what that would look like. And obviously whatever you get paid outside of college, like right outside of college is usually not shit. It’s usually like, like not great.

Syama Bunten: So how did you kind of navigate that? Like what was your first job? Like, how did you navigate being like, my parents could easily like really help me here, but I’m like trying to do this on my own and there’s tension there. I imagine. What was that like?

Wendy Ryan: Yeah, they, you know, it’s interesting because since I didn’t know what I wanted to do there they said you can do go anywhere, study anything.

Wendy Ryan: You know, it’s kind of like we, we have no opinion in the matter. But since you don’t really know, why don’t you just consider going to a uc school, right? A uni, a public school, because that way, you know, and then if you later land on something. Then go to the best grad school you possibly can in that field kind of thing.

Wendy Ryan: So, I mean, Davis is a great school, don’t get me wrong. It’s not like, oh, I, wow, I only, I settled for uc, Davis. But there, there really, it, it’s interesting ’cause there was some efficiency in strategy in their thinking there of why overpay for a private school. Right. Even if I could have gotten into a school with, let’s say, an even more robust reputation, they didn’t really see the point and they didn’t encourage that.

Wendy Ryan: And because I was a teenager, I was like, oh, good, I only have to fill out four applications or whatever that, so I, I applied to four ucs, I got into two and I chose Davis. Wow. And that was that.

Syama Bunten: Oh, it’s so great. I mean it’s, I think it’s really like, it’s wonderful. Even though they gave you no boundaries, they did have pragmatic.

Wendy Ryan: Yes. They were pragmatic people at the core. They, and they were that way their whole lives. They were not they were not frivolous with their wealth.

Syama Bunten: Yeah. I think that’s, uh, it’s really powerful modeling as well, right? It’s like this idea of, especially, you know, in, I remember watching the early like nineties, what is it?

Syama Bunten: Like Robin Leach, you know, and it’s like, you know, and you’re like, oh, it’s

Wendy Ryan: lifestyles are the rich and famous,

Syama Bunten: you know? And all of a sudden things get very real and it’s like, all right, but actually, where does the money go? And actually, like, what are the trade offs and, you know, all, all of that. What does that actually look like?

Syama Bunten: And so talk to me a little bit about some of these early jobs you had, right? Was it a need to negotiate on salary? Was it something more like, I’m excited to prove myself? How did you start to build your career? Because also. There are so many folks who have, let’s say, different career jumping off points and different strategies, but you’ve also had a, a fairly linear path in terms of your interests and your contribution to the world.

Syama Bunten: And in an era where everyone’s doubling down on let’s say technical skills and being engineers, like, you’ve also really sort of doubled down on people, right? And on the core of what I think is essential for humanity. So talk to me a little bit about some of these like building block days of your career and some of these pivotal moments where you started to understand both your own sort of zone of genius, if you will, the things you’re uniquely good at, but then also building up a life because like that’s hard.

Wendy Ryan: It, it took a while. I coming, as I approached the end of college, I. Had sort of two, two paths in mind. Finally, the first path was, I’m gonna become a therapist. I’m gonna become a psychotherapist, I’m gonna go get a PhD, and I’m gonna do that track.

Wendy Ryan: The other path involved business, because I figured out that I really enjoyed business and some of that was through the retail experience. I, I just kind of had a, a natural affinity for it. I enjoyed it. I thought it was fun to figure out how do you make something work? So in a way it was like engineering, but for me it was like, it’s just always been very easy and intuitive to look at a business and be like, I can tell if it’s working or not working.

Wendy Ryan: And it’s not about the numbers because I’m not necessarily a numbers person. It’s a systems, it’s a way of being able to see systems that I’ve always had, I thought about those two paths, and as I started looking into PhD programs, I went, wait a minute, I’m gonna spend another five years in school and then I’m gonna, and then I’m gonna be a therapist, but I won’t have had any like, or much real world experience.

Wendy Ryan: And that bothered me. And I thought I think I wanna give this business thing a try because I could go back and do that PhD thing later, but I really wanna see what that’s like. But since I, I really am drawn to people and to systems around people, why don’t I do human resources? Because. That seemed on the face of it to be like where those two things intersected.

Syama Bunten: I mean, they do, right? I mean, it’s so like, I mean, it’s also, it’s like organizational design, psych, it’s like taking psychological principles and like figuring out like, I mean it’s so like, it’s really such a important, I feel like sometimes people don’t really understand like what it means to, to like link up, not just like skills on paper, but actual like psychological assessments of like how people can handle pressure and work within teams.

Syama Bunten: And that’s also super messy too, because it’s like, you know, now if like people have problems, it’s like you are right in the middle of it. Wendy.

Wendy Ryan: Yes. So unfortunately for me, I graduated in a year when we were in a recession. And it was impossible to get a job in human resources, an entry level job.

Wendy Ryan: So I, I do feel a lot of resonance and empathy with people going through this today that are new grads that have worked hard, who have done well and cannot find a job and at least an entry level. So it took probably four months, which at the time was really long. And this was back in the day where, you know, you printed your resume, it was on nice paper and you did the, all the in-person interviews.

Wendy Ryan: And I finally landed a temporary job for $10 an hour. And it was, I bet you used

Syama Bunten: some nice, I bet you used like nice resume papers.

Wendy Ryan: Such nice paper. Like

Syama Bunten: wasn’t it a really good resume paper?

Wendy Ryan: Yeah. Like, it was like, it was solid. You know, I was, I was proud of it. It was like the linen. Finish, you know, it was like nice.

Wendy Ryan: And so and it was with a temporary placement agency. And so what we would do is basically every morning at 7:00 AM we would come in and we would get calls from all the local companies in Silicon Valley who were doing like light assembly, like circuit boards, soldering doing light packaging kind of thing.

Wendy Ryan: There was more of that in that time. And they would say, okay, I need Roberta would call and say, okay, I need 15 assemblers, you know, at 9:00 AM and then we would just start, you know, dialing for those people. We had our database on a mainframe of people who had come into our office and interviewed and we’d qualified, and then we would send them out and I mean, it was.

Wendy Ryan: It was fast, it was the pace was just kind of insanity.

Syama Bunten: I mean, how crazy. I can imagine being like, alright, I got this one, I got this one. Yeah, it was like

Syama Bunten: the, like trading stocks on the, on the exchange like

Wendy Ryan: yes. It was a lot like that, I imagine. And then the rest of the day, people would be coming in and we’d be interviewing, right.

Wendy Ryan: And building that database. So I did that for about a year. I felt like five. I worked my ass off it. I worked 12 hours a day, 10, $10 an hour, and we had to wear, I’ll never forget, and I tell people this now and they’re blown away. You know, like my daughters are like, what? I can’t believe this.

Wendy Ryan: You had, we had to wear suits. Skirt suits. That’s right. Like Jays New York, the suit with the blouse that match whatever pantyhose, high heels four days a week. So Monday through Thursday and then on Friday, the big thing is that we could wear a pan suit. Woo. Woohoo.

Syama Bunten: Woohoo.

Wendy Ryan: So, you know, you could wear pants, it was like Wow.

Wendy Ryan: Casual Friday. Um, and I had to, I had to afford that on $10 an hour.

Syama Bunten: Wow.

Wendy Ryan: And when I think about it now, I’m like, what a mismatch. I mean, we should have been able to wear whatever.

Syama Bunten: It’s so funny, I remember when I graduated college, the first thing I did was I opened up a Banana Republic credit card and I bought two suits and like four shirts that were like cropped.

Syama Bunten: You know, just like stuff that was like of that time. I wore the hell out of those things. I mean, it was like, that was like the Bible, right? It’s like,

Syama Bunten: oh my God. Okay. So you were there for a year and then, and then where did you sort of find yourself launch padding into the next things? Was it like, this is not for me, this is like yeah. The sucks. Like, how, how do I find my next thing?

Wendy Ryan: I was like, wow, if I’m gonna work this hard, I’d like to get paid more, because I was living with my parents and I was like, I can’t afford to move out because I, you know, it was kind of a tough situation.

Wendy Ryan: So I, and it wasn’t that they were tough to live with or didn’t want me there, I just was very much in the. I should be living on my own.

Syama Bunten: Well, yeah. It’s also tough to be like, oh, I’m out, I’m in, in my twenties and, you know, I’m having this date. Pick me up at my parents’ house. I get it.

Wendy Ryan: Exactly. Yeah.

Wendy Ryan: So I, and I thought to myself, you know this is close to hr, but it’s really recruiting. I’m doing recruiting and I’m doing sales. ’cause the other thing we would do is go and go to potential clients or go to clients and drop off candy. And, you know, I did a lot of sales calls with my manager and that was, again, lots of learning, great experience and not really what I had envisioned in terms of like doing organizational design or Yeah.

Wendy Ryan: Those things.

Syama Bunten: I understand.

Wendy Ryan: Yes. So I left there, I got a job as an HR assistant. So I’m like, Ooh, I’m moving from recruiting into actual hr. And I was there for about four months and I was doing affirmative action plans. That was all I did all day long was to, because back in the day, this was a, a government service contractor, um, and they needed to report all this.

Wendy Ryan: So it was looking, gathering all the stats, putting it together in these reports, putting it in a binder, all those things. And one day my boss called me into the office and I really liked her. Her name was Renata. She was amazing. And she said, I think you should look for another job. And I was devastated I just thought the world is coming to an end.

Wendy Ryan: This is the worst thing that can possibly happen to a person. And, uh, she said, my, my friend has a job. Over at her company. I, you know, I think you should go apply for it. And I was like, I didn’t know what to do with that. You know, I thought, well, is this like a, is this a test? Am I supposed am being

Syama Bunten: demoted?

Wendy Ryan: No, I can’t. Like, I can’t, I wanna work here. You know, what am I supposed to do with this? So I went home end of the day, went home, thought about it, and then there was this little voice inside of me that said maybe the next morning, Wendy and I actually talked about this in, in my book as well, but, um, now if your boss tells you, you, you should think about looking for another job, it’s probably wise to listen, regardless of the reason.

Wendy Ryan: And so I did take that advice, I applied for that job, and then I went to work for a, a company, a medical device company in hr and. Really enjoyed that. I was there two and a half years. So for me, comparatively a long time.

Syama Bunten: Yeah, I mean, at that time, I mean in terms of your adult years, like you’re, you know, you’re

Wendy Ryan: really, I was like, wow, dedicated.

Syama Bunten: I mean, it’s, so were you able to move out? When did you move out? Like what, what?

Wendy Ryan: And then I think I moved out. Okay. I’m not exactly sure of the timing ’cause it’s been a minute. But I think that finally then I was like, Ooh, I’m making, you know, $24,000 a year or whatever, like big changes.

Wendy Ryan: And I really enjoyed that job. It was, I got to do a little bit of everything. So it was really learning a training ground for me of how to become an HR generalist and really appreciated that opportunity.

Syama Bunten: That’s so cool. You know, I feel like, um, what’s also interesting about, about human resources is the different kinds of companies you get to see into, I mean, it is.

Syama Bunten: Really like this. And then also the salaries people are getting paid and all the benefits and who negotiates and who doesn’t and like, and how this shakes out. So spill the tea on this medical company. Like what did you notice? Like, you know, like were, was there anything interesting that came up for you?

Wendy Ryan: That was the first time that I had exposure to stock options and they were ISOs instead of incentive stock options back in the day. And I was actually part of my responsibility was preparing the list of, ’cause this company was growing fairly rapidly and I got stock options. Every new hire got some, some stock options and we had an employee stock purchase plan, which I did participate in.

Wendy Ryan: So when I left there two and a half years later, I actually ended up. Selling that stock and I made money on it. And that was a powerful lesson in the value of having, being in that asset class. And also, I remember by then I was married at the time and telling my husband, well, we could hold out for the stock to go higher, but it’s already appreciated quite a bit.

Wendy Ryan: I kind of feel like, you know, we should just take the money off the table and then go do something else with it. And I think that set up a practice that I follow to this day, which is kind of, for lack of a better word, don’t be greedy if you’ve made a decent return on something, get harvest that so you can now go create something else with that resource.

Syama Bunten: How old were you when you had this wisdom? 27, maybe 26.

Syama Bunten: That’s pretty, that’s a lot of wisdom.

Wendy Ryan: Not too bad. 27

Syama Bunten: too girl. Like

Wendy Ryan: that’s

Syama Bunten: give yourself some big credits here. Like, that’s like young and savvy. And so did that just come from your own, like Wendy, Ryan Wisdom or was that something you had picked up from like, you know, professor, I mean, it sounds very intuitive, right?

Syama Bunten: It sounds like something that was probably like my, in my gut, my heart, my soul is telling me this is the right move. Can you attribute that to anyone else or was it sort of your, your inner guidance that was leading you?

Wendy Ryan: I think it was inner guidance. I think it ultimately comes back to what I have come to understand is fundamentally how I relate to money or the relationship that I have to money, which is that in my worldview.

Wendy Ryan: Money has no intrinsic value. It only has value when we actually exchange it for something. So if I am saving all of my money, right, saving a ton of money, saving, saving, saving, putting an account there is something that helps us feel more secure about that or good about ourselves because we all wanna think that on a rainy day we’ve got access to something.

Wendy Ryan: But the reality is it’s sitting there isn’t benefiting me right now. And so I think that what that has done, I’ve always seen money as it’s a, it’s a secondary currency. It’s actually not a primary, primary resource, it’s a secondary resource. I forget what the technical terms are for that, but that always made a lot of sense to me.

Wendy Ryan: And so I think it has. Helped me have a really healthy respect for the value of money and capital, but also not be hooked emotionally. I don’t like, my ego doesn’t go, Ooh, wow, my bank account is up this month or down this month. Somehow I’m able to sort of stay detached enough from that, and I think that was true back then as well.

Syama Bunten: Powerful. It’s also, I mean, to be so aware of your own values, right? Like what is important to me, what is not important to me. Also at 27, to have some income come in that materially changes some things, right? Where you’re like, oh, I can now make a different kind of a decision or, or I have some more agency over my capital.

Syama Bunten: What did you decide to do? I mean, obviously you probably sold off some of that stock, but like where did you start to, what did you then do with your money to start to build your young life? You know, was it buy a home? Was it like, you know, we’re working towards these goals. How did you start to exercise your capital?

Wendy Ryan: Yeah, so the person I married, his name is John, we’re still married today, very happily. Uh, we’re just very fortunate to find each other and he is very frugal, just inherently, biologically, genetically, however we want to think about that. So when we got married, I had a little bit of money. He had saved money and we were able to buy a house immediately, which again, is something that is rare for very rare in the Bay Area for anyone that age.

Wendy Ryan: So. We took advantage of that and we bought our first home, which we still have today.

Syama Bunten: Wow.

Wendy Ryan: Yeah.

Syama Bunten: Oh my God, that’s so cool. I love that.

Wendy Ryan: Yeah. It’s not where we live now. Yeah. But we still own it.

Syama Bunten: That’s

Wendy Ryan: also, yeah. So now it’s an income generating property

Syama Bunten: that’s really fantastic. So then at this sort of early thirties, late twenties, like you’re, you already have a home, like how, how savvy, obviously you have exposure to equities because of your work experience, um, which is also something that I think not a lot of young people automatically get that sort of exposure to.

Syama Bunten: At what points and how did you start to, you know, build either in that capacity with, you know, continuing to understand equities or starting to think about, you know. Oh, I can have an income producing house or, oh, there are other things that I can do with my money. When did those light bulbs start to go off for you?

Wendy Ryan: I had the opportunity after I was with the medical device company for about two and a half years. Shortly after I got married, I went and worked for a different company and that company was doing outsourced HR because I was starting to feel like I couldn’t really do what I wanted to do at the medical device company.

Wendy Ryan: I wanted to apply for a job that came open that was two levels above me. And my boss said, no, but you’re doing this over here. And that was sort of not the right, that was not the right thing to to say to me. ’cause I saw that as a challenge that yes, I could do the thing I was applying for. Plus, and I was gonna go find somewhere else to do that.

Wendy Ryan: So I ended up at a outsourced HR company, and that was drinking through the fire hose. All of our clients were VC backed startups, about 99%. We were growing very rapidly. We were the first to market with online benefits, enrollment, uh, a lot of things that were very innovative technologically. And this was the late nineties.

Wendy Ryan: It was the.com boom. There was new companies being created right and left every single day. And so my job was really to work with a portfolio of companies and work directly with the CEO. Mind you, some of these companies were two people, some were a hundred people. They varied in size. But really to work with them and to be their HR generalist and handle everything from, you know, helping their new hires get enrolled in benefits and understand those choices.

Wendy Ryan: But also I think more importantly, to make strategic decisions about what, what they were going to offer people.

Syama Bunten: Oh my gosh. So at that time you were basically already, you were like an active board member for like all these

Wendy Ryan: different

Syama Bunten: kind of

Wendy Ryan: Yeah.

Syama Bunten: Startups.

Wendy Ryan: Yeah.

Syama Bunten: Who are trying to navigate what’s going on.

Wendy Ryan: And I just kind of figured out how to do it. ’cause there wasn’t like enough time or people at headquarters to kind of teach us how to do it. They were just like, oh, you seem pretty smart. Pretty with it. You’re pretty good with people. You’ll figure it out.

Syama Bunten: It’s so fun. And did you start to then get exposure?

Syama Bunten: I guess I’ve imagined to the. Like funding rounds and what some of the, you know, what these funding rounds potentially did in terms of growth and scale of employees and starting to correlate maybe some of these different components.

Wendy Ryan: Yes. And having, you know, direct insight into compensation packages, all, all across the board and stock options.

Wendy Ryan: And then what happened when you wanted to fire somebody that had a significant amount of stock or was an executive in your company. And then we had the, the.com, we had the crash and then all of a sudden it was, okay, now how do we lay all these people off and having to go through that side of the equation as well.

Wendy Ryan: So I got a pretty early and robust exposure to VC funding to. How do you do a startup and how do you think about all the people pieces of that?

Syama Bunten: That’s so fascinating. ’cause it’s also talk about something else that’s really informed the rest of your life, you know, as far as like how you now engage and support companies and invest in them.

Syama Bunten: I think it’s so interesting to think about also human resources as this like pathway where you are deeply needed when businesses are scaling and then deeply needed when businesses are downsizing. Like there is, there is like always a need for someone who’s willing to, um, oftentimes I feel like, do the things that sometimes CEOs and founders don’t wanna do, you know, which is like deliver the news and um, do so in like a, in a compassionate, kind way that has people’s best interests at heart.

Wendy Ryan: Yeah, and listen, most of them do it poorly and not because they’re all. Uncaring self-centered people. I’m not suggesting that, but it really is a, it’s a skillset and it’s knowledge. And as much as I did not enjoy having to support that or see people lose their jobs, I did, I was appreciative of the fact that I could kind of reduce the amount of unnecessary suffering because stupid things weren’t being said to them because the company was orchestrating things in a way that was, that insured a lot more dignity for people.

Wendy Ryan: And without that kind of guidance and coaching I know a number of times it, it really would’ve been a far different experience for the people impacted so.

Syama Bunten: Wow. Had you at that point yet, Wendy done any venture investing. You know, now you’re CEO you were seeing sort of how like the sausage is being made and, and I feel like if most people saw how the sausage is being made, they’d be like, oh shit.

Syama Bunten: This is how this is how it works. Oh my god, this is wild. So had you, it’s

Wendy Ryan: pretty messy.

Syama Bunten: Yeah. Mm-hmm. So had you done any, any angel or venture investing at that point yet?

Wendy Ryan: No. I had stock options again with that company that I was with, and they actually tapped me to to lead kind of a new part of the business.

Wendy Ryan: So they were standing up a different service model and they wanted me to lead that. And I actually said no. And I said, I said no because I said, I think you’re over your skis. I don’t think you’re delivering, like the company had grown so fast. And was adding customers so fast, I said, I don’t think we’re gonna be able to deliver what you want me to promise to deliver.

Wendy Ryan: And I, I’m, that’s, I can’t be in my integrity and do that. And so I walked away and had I stayed this company later did get purchased by a, a strategic so my stock, you know, would’ve been worth more.

Syama Bunten: it’s fun to like, follow the stock,

Syama Bunten: and so obviously, you know, you and your husband had children and you know, there’s, there’s like a family that’s also emergent. Obviously knowing that your children have grown up differently, at least before the age of 12 than you did, right? So there’s like some real differences.

Syama Bunten: How did you start to approach. What life would look like at home. You know, I, I find that there’s often a, a bit of a, it’s like, how do I give them everything in the world but not give them everything in the world and like, you know, allow for constraints to happen. And certainly I think when things have been so different when we’re young, right?

Syama Bunten: When we have such contrast, there’s a desire to protect and nurture and care take. How did those things start to show up as you were raising a family?

Wendy Ryan: Mm-hmm. So, yes. So for, for us, we started having kids in our early thirties. So our whole kind of decade of the thirties was launching the family and figuring out how do we do childcare and work?

Wendy Ryan: Does one of us stay home? Does one of us work full-time? Do both of us work part-time? And we, we pretty much went through every potential. Configuration you can imagine. So at one point in time I was working full-time. My husband was working one days, a day, a week, and being as we would say in the day, Mr.

Wendy Ryan: Mom the rest of the time and everything in between. And so we tried a lot of different things economically. We were not you know, my parents were not giving out money. Like they, it wasn’t that we did have to work and we had to save. And we were very concerned about how are we gonna send our kids to college?

Wendy Ryan: How are we going to make sure they get the best education and life experience? So we, we had to, like most people, really be mindful about that. And we, I never viewed my parents’ assets as my money ever. I always thought about it as that’s theirs. They might live to be 120 and spend it all, like I, I had no claim on it and I really chose to live life as if that didn’t exist.

Wendy Ryan: So aside from getting to go on some nice vacations with them, we really operated, again, much as a kind of typical middle class, upper middle class family would.

Syama Bunten: I think it’s really, um, it’s, it speaks also to your I’m gonna do it on my own. You know, like I’m gonna, you know, don’t tell me I can’t do that.

Syama Bunten: ’cause now I’m gonna go and show you that I can do that. Plus, you know, which, which I think’s, um, something that I think a lot of women do. You know, it’s like very much around like I will figure this out. I will show you. And and, and no matter how scary it is, I’ve got this under control no matter how scary it is, you know?

Syama Bunten: And, and, and what some of the uncertainties look like as you developed your career into in the consulting world, right? And, and sort of starting to build business and, um, have your own business and, and start to sort of move into these different realms of. Of career progression, but also of curiosity.

Syama Bunten: You know, I think it takes a, a great deal of, of risk and faith in oneself to say, you know, I’m going to move into different stages of, of not being employed by the man, you know, and, uh, and, and sort of build something on my own. What unfolded for you? Like what were some of these pivotal moments or, or inflection points where you were like, all right, my heart is telling me something else and I need to listen again.

Syama Bunten: And as you decided to listen to yourself, was it, you know, a family conversation and decision? Was it, you know, I’m listening to myself and like, and I’m gonna make the case for it? Or how did you sort of figure out these different inflection points that started to unfold your path?

Wendy Ryan: Probably more the latter as you were asking.

Wendy Ryan: I was thinking my hu husband probably wish it was more the former, but that’s not who he married. Yes, and, and you know, thank goodness he’s, he’s always been very, ultimately very supportive of all of my creative career directions and, and choices and so forth. So I did move out, move from the outsourced HR company to independent consulting, but I did that with firm. And so it was similar to other career transitions that I’ve made in that I basically was thrown into the deep end of the pool and said, okay, now you are an executive coach.

Wendy Ryan: You’re gonna facilitate team development. You’re gonna use these assessments, you’re gonna give feedback, you’re gonna coach people, and good luck. And so I kind of feel sorry for the first people I worked with because they didn’t know they were Guinea pigs, and I did not know what I, you know, I, I mean, I had some idea of what I was doing having worked in hr, you do develop some skills like that.

Wendy Ryan: But I mean, these were executives, you know these were people who probably rightfully had high expectations. And I it took me a minute, but

Syama Bunten: I bet you over-delivered. I bet. I bet. They were like, we have never experienced a woman like this who’s like,

Wendy Ryan: I was good

Syama Bunten: bringing all these Yeah, I bet you really crushed it.

Syama Bunten: And I bet like no one had any idea.

Wendy Ryan: I hope so. I was very good at it. And what I have. What I talk about now is I figured out the common denominator in all the things that I’ve done is that I am a, a very good integrator, synthesizer educator, and now investor. And those things will, you know, get, you, get you pretty far.

Wendy Ryan: A lot of the essence of coaching is you’re just trying to integrate a lot of information quickly, put it together and package it in a way that someone else can understand and then they are compelled to do something.

Syama Bunten: I think that’s really, yeah, no, I think that’s a wonderful it’s a wonderful life skill to learn that, you know. So it’s coming to my mind. I’m like, yeah, you gotta like package it and make ’em do it. You know? How do you keep, like, how do you keep doing that? At this time as you were sort of building this consulting role did things start to emerge for you around like, wanting to be the boss?

Syama Bunten: You know, like it sounds like being the boss was always in your future and it was like slowly coming out. Um, when did you realize that, that you wanted to be the boss?

Wendy Ryan: I came to that realization, it was 2014, so I did take a career break. I actually took seven years. I thought it was gonna be two years, maybe three years, because we had three children in, it was crazy town for a while and.

Wendy Ryan: I thought, okay, I’m just gonna, you know, step back from consulting for two, three years until these two get in, get into preschool kind of thing. Like, you know, it was, all of, it’s as so many working parents understand, it’s all about the childcare and how that how you fit all that together.

Wendy Ryan: It ended up being seven years and during that time, I, you know, I did volunteering. I always stayed kind of busy and people would constantly ask me like, well, you work, right? So I guess I always came across as somebody who was working even when I wasn’t working, which is interesting. You know, I, I joined the, the nursery co-op and then I ended up running it, right?

Wendy Ryan: So I always found myself throughout my life a theme husband. Yes, I have ended up being the boss and not because I crave. the spotlight necessarily. I just kind of know like how things need to happen and get done. And people tend to have confidence in my ability to do so. So they’re like, why don’t you lead?

Wendy Ryan: You know, why don’t you be, why don’t you run this? And so that happened. And so then I was like, okay, it’s time to go back. This was about 2011 time to go back and I could not get a job. So in hr, in consulting, everybody said the same thing, which is like, you’re great. Your background’s phenomenal and we’re gonna hire this person instead who has more recent experience.

Wendy Ryan: And I remember feeling such cognitive dissonance because I thought, gosh, I am so much better than I was before I had to do this. Seven years of like parenting and. Figuring all these other new things out. I don’t understand that. it took a minute and then the second that the, my old boss principal at the consulting firm heard that I was looking, she’s like, oh my God, you have to come back and work for me.

Wendy Ryan: ’cause she knew what I was capable of doing. And so she didn’t hesitate. She’s like, oh my God, I need you yesterday. Come back. I’ve got plenty of work for you. And I was like, great. I didn’t really wanna go back and work for her though. I wanted to, to, you know, take that next step. And so I think that was wow.

Wendy Ryan: Frustrating. That was valuable because she now had started partnering with a private equity firm and working with their portfolio companies. So in the four or five years that I. Was working with her firm again, I got to learn, I had learned about venture, I knew about startups, and now I was looking at what happens with middle market companies and private equity and how does that whole game work?

Wendy Ryan: And so I had a front row seat to that and I worked with the leadership teams at a dozen of their portfolio companies. And it was intense and it was a really good learning curve. And then I started to get restless. So after about four years of that, in 2014 to 2016, I thought there’s new things coming out.

Wendy Ryan: There’s new models like neuro leadership, um, there’s new theories and things. I wanna try some new things. And at that time, the firm that I was working with, they weren’t interested in changing. You know, it was like what we’re doing is working for us. It makes our private equity partner really happy, and so we don’t wanna try new stuff.

Wendy Ryan: And I thought, well, if I, if I wanna do that, I’m gonna have to build my own sandbox. I’m gonna have to take a risk with my own name and reputation. And I also had this like, burning desire to say, why is leadership development so hard? Why is most of it so not effective? And can I just create the blueprint for what great leadership is?

Wendy Ryan: I wanna work on that. And so that’s what I did and that’s why I launched Cadra, my firm. And so was that like, so did you guys talk about it at home, like, we’re gonna launch this business and like, you know, I mean, most people think, you know, working for someone else, you work long hours, but then it’s like you work for yourself and like, you know, the, you can be the worst boss you’ve ever had.

Syama Bunten: So there’s like, you know, there’s also some dissonance here between like what people think it is and then like what it really is. So what were some of the ways in which your family and you guys experienced together the building of your business? It’s interesting because I made the decision to start building this business, but it was a soft launch.

Wendy Ryan: You know, I continued to work for the other firm alongside of that, which was fine. There was no conflict there. I was an independent contractor for them. And it is not. Atypical in the leadership development business for people to be working for several different brands, if you will, or for us to work for each other under different brands.

Wendy Ryan: It’s kind of a, there, there’s just so many boutique firms and, and there’s so many different specializations that are needed at some point that you kind of need that. The labor supply is very fluid that way. So I kind of made that decision. So it wasn’t like a I’m gonna stop working for this firm and start my own firm.

Wendy Ryan: It wasn’t a heartbreak. It was kind of a, a soft launch alongside. Yeah.

Syama Bunten: Well that’s easy.

Wendy Ryan: So I don’t think, yeah, so that was pretty easy. About four months after that I decided, okay, I’m gonna soft launch this. We had started to remodel our current home that we live in now. So we had moved out of our house.

Wendy Ryan: We were living with my dad at the time. And then he unfortunately passed away. Our remodel wasn’t done. We were living in his house. We had no signed lease, we had no documentation. It was all a verbal agreement and neither me nor any of the other siblings were were executors. So there was a moment, and I think that’s a, a teachable mo moment to share is even when his family get your documentation.

Wendy Ryan: So then my husband and I were looking at each other going, shit, we have three little kids. We don’t have a home, and they could come along and throw us out anytime. Now what do we do? Ouch. So it was a real, not a good feeling. And I remember my husband also turned to me and he said, do you, you realize like.

Wendy Ryan: Now there’s probably gonna be some sort of inheritance. And I’m like, well, what are you talking about? Because like I said earlier, I literally had never thought about it. Uh, I literally had never thought about it.

Syama Bunten: Totally.

Wendy Ryan: So it was like I was, I was in shock, you know, I was in shock that he died. I was in shock at the timing, and I was in shock even just thinking about, oh, now we may have money that we haven’t had before, and now a whole bunch of other decisions are gonna have to be made.

Wendy Ryan: So I wasn’t, you know, frankly working too hard on the new business at that time. I was just trying to kind of process all of this, you know, and, and, um, we were able to accelerate the remodel, get into our house. JP Morgan did not throw us outta the house. Thank you, JP Morgan. And all, all was well.

Wendy Ryan: And then that. Changed the trajectory of, of my financial life and my family’s for sure.

Syama Bunten: Wow. It’s a lot to process. I don’t think people really give, give these big moments enough space, you know, like it’s, it’s a lot to say, you know, these big life changes are happening. Someone who I love and care about is no longer in my life.

Syama Bunten: And there’s this other component that in many cases it’s like, okay, how am I supposed to feel about this? You know? Yes. And, and like, what does this mean to me? And, and am I worthy or deserving? Or what do I do and what, how do I stay responsible? So how did you start to answer some of those questions around inheritance and, and what they would start to mean for you and your family?

Wendy Ryan: Yeah. It was. It was a really interesting journey, and I’m really aware of the fact that we are in the middle of the biggest wealth transfer in history where more money is being inherited by women for some period of time. It’s about a 10 year stretch than ever before in history. So, as we talk about this, I just wanna acknowledge like this is gonna happen to a lot of women is happening to a lot of women in particular where you have a windfall, which is what an inheritance essentially is regardless of the size, but there’s so much grief around it, you know, so if the reason that you’re getting a windfall is because you’ve just lost your husband or your parents, it, it’s, it is very complicated because you don’t, it’s very hard to feel happy about a windfall when you’re, when you’re deeply grieving.

Wendy Ryan: At the same time, having a windfall can also give you some feelings of relief and a little bit of excitement about now what’s possible. Like for my husband and I, one of the really tangible changes that it made is that my parents had set up as part of their estate plan you know, trust funds for all of the grandchildren to be used for education and so forth.

Wendy Ryan: So what it meant is all of the, the money that my husband and I have been trying to save for years to send our kids to college was no longer needed for that purpose. Wow. Which is huge. Huge. That’s huge. Huge, huge. And so. There was appreciation around that, you know, and a little bit of excitement like, Ooh, now maybe we can do some things we didn’t dream of Dr.

Wendy Ryan: Dreaming it. I think the best way to describe it is enormous grief with a tiny sliver of hope for the possibility of dreaming.

Syama Bunten: So what were some of the early dreams that you started to piece together? All of a sudden now you get this, as you say, breathing room, right? To like, uh, okay, I can step out of these like, primal parts of the brain that are worried about safety, security, family, like, like real things that, that so many humans today are, are living with without being able to give themselves the ability to dream bigger.

Syama Bunten: And now you have an opportunity to actually say, wow, I can think of a, of a world now. For myself, for my family, is maybe a little bit more sparklier or a little bit more, you know, there’s something more magic, right? That happens when you can start to like move away from the primal brain and, and start to move into dreaming states.

Syama Bunten: So what were some of those early dreams that you started to have?

Wendy Ryan: Remember? I think first it was, oh, now if we really wanna take a trip somewhere, like if we wanna go to Japan or we wanna travel to X, y, Z, we actually really can do that without it being, uh, a huge trade off for the budget without having to sacrifice something else. We can go do that. Which felt really indulgent and wonderful.

Wendy Ryan: And we, we did take a couple of trips. We haven’t gone totally crazy that way. But, it was wonderful to feel like that was possible. And really what it meant for me as an entrepreneur is that I could continue to self-fund my business and I didn’t have to worry about am I, what is my revenue?

Wendy Ryan: It was, it gave me the luxury of building at a pace that was sustainable for me and my family and I didn’t have to worry about how am I going to access capital if I need it. And that is not something I appreciated or realized at the time was I really took that for granted at the time. ’cause I didn’t know, I didn’t know that that’s not most people’s.

Syama Bunten: Yeah. You know, it’s wild to think about the conditions that have to be right to become a founder and what are the sacrifices most have to make to be able to see. Something come to reality. And, and it’s, um, it’s something that I think is, you know, some people have to take deep sacrifices.

Syama Bunten: Others have to really leverage friends and family. Some don’t have friends and family to leverage. Like, there, there are so many different things at play into this world of being a founder and entrepreneur. And honestly, it gets really over glamorized. You know, it’s like, I don’t think enough people are like do you know really how long it will take for this business to, especially if it’s your first right?

Syama Bunten: If you, if you’ve been in doing businesses for some time, I think there’s like some levels of like, I do understand how hard this is gonna be but in the beginning, for your first one, it’s difficult. You know, it’s challenging to think about customer acquisition, but then also paying for kids education at the same time as thinking about customer acquisition and.

Syama Bunten: Holding so many different things in your mind all at once that, um, certainly having some financial pressure relieved right, sort of gives you the opportunity to let your business become the thing it’s going to become on its own time.

Wendy Ryan: And, you know, we were able to build a really beautiful special business and team because all of those things were available to us, and I am forever grateful for that.

Syama Bunten: That’s powerful. At what point did you start getting more curious about the different asset classes you would start to invest in? Invest and sort of starting to think about what your capital could really be and do and create in this world?

Wendy Ryan: I thought about angel investing. I started thinking about it in early 2018, and I, I cannot remember exactly why.

Wendy Ryan: Except that I remember the idea came across my brain one day. ‘ cause I knew that some people did that it was a thing because again, I, I knew about VC and I knew about private equity and I knew there were such a thing as angel investors too. And it immediately scared me. And I thought, oh no. Yeah, no, that’s not for me because I am an HR person, I’m a leadership person.

Wendy Ryan: I’m not, I, I’m not a investment banker. And I remember very distinctly kind of stopping myself in my tracks and going, that’s exactly why you need to go do that. ‘ cause it’s something that, that scares you, makes you nervous, it’s gonna challenge you in a new way. And I’m a person that apparently likes to get thrown into.

Wendy Ryan: Or if I’m not thrown into the deep end of the pool, I will just jump in. Uh, apparently that’s how I roll. Yeah, and I’ll just figure that out too cause that’s something new for me to figure out. Um, and so I did, I joined Golden Seeds. I, I researched who was investing in women-led companies because at that point in 2018, I was really clear that women had a very different career and leadership journey than men did.

Wendy Ryan: And I somehow was waking up to the fact that it was also harder for them to access capital. That my ability to access capital was very unique and not common practice. And I thought, oh, if I’m gonna do this I’m gonna invest in other women founders, right? Other women entrepreneurs, and help them succeed in their business.

Wendy Ryan: And that started, started my journey as an angel investor and as an LP in venture funds.

Syama Bunten: What was it like to write the first check? How did you feel? And like, so

Wendy Ryan: much fun. Yeah. Was it just like, oh my God, I can’t wait. Like, and who, like what was, yes. The first check, as an LP in a fund was the first check as an angel.

Syama Bunten: So what was the first check and like what went down? How did you do this? You know, I was fortunate because I had chosen to join a group and of angel investors and I could watch and learn and had some, some mentorship, some examples. So I wasn’t really, even though I was, I was in the deep end of the pool for sure.

Wendy Ryan: I, there were a few buoys or floaties I could grab onto once in a while to kind of help me orient and figure out what the hell I was doing. And I. I remember writing my first check and it was like, you know, it was $12,500, which is not a ton of money in the angel sphere. It’s a whole lot of money for a lot of people.

Wendy Ryan: I wanna acknowledge that. But in the angel sphere, it’s not necessarily a huge amount of money. And I was like, oh, I didn’t miss it. And it was fun. And I immediately thought, oh my God, I wanna do this like 20 more times. This is so much fun because I loved hearing about this founder story. I loved hearing about her business and what she was trying to do, and it was so cool.

Wendy Ryan: And I thought, the world needs this and why isn’t it here already? And all the things. And it was really interesting as I was observing other new angels in the group, and some people just, they kept waiting to write the first check and they kept waiting to write the first check. And six months later they were still waiting to write the first check.

Wendy Ryan: And I was just like, what’s going on? Like, why aren’t you writing checks? Aren’t we here to write checks? ’cause I’m here to write checks. So there was definitely some judgment there. In my part of, I’m a fast decision maker. I, again, I integrate, I synthesize, I make a determination, and I go I don’t take a long time to do that.

Wendy Ryan: And it’s not right or wrong. There’s some good things about being a little more. Deliberate and some good things about not waiting too long, but I, I write checks like the way I do business, which is pretty

Syama Bunten: Yeah. And you also have a strong connection to your intuition, right? And, and sort of like what feels right and what are the right moves.

Syama Bunten: And, you know, that seems like it’s been really consistent over time. You know, how you’ve chosen to make decisions and show up with integrity in, in your values. You have been an important part of, show her the money and that is a, a film that many of the folks who are listening to the show are, are familiar with.

Syama Bunten: But I’d love to just double click a little bit more on how you decided to go from being, let’s say, behind the scenes and learning to in front of the scenes and being like, you know, someone who’s. Out there talking about these things and activating people with their capital and starting to evangelize, right?

Syama Bunten: And, and being like, Hey, if I can do this, like you can do this and, and here’s how we do it. How did you make that crossover from back of house to front of house?

Wendy Ryan: I think because I, I’ve always been at heart, a bit of an educator. It’s natural for me as soon as I feel like I kind of understand something to want to explain it to someone else if they’re interested.

Wendy Ryan: So I think that is really, for me, where the evangelization comes. It’s like I want everyone to, especially if women to be investors, I want for so many reasons, right? And that’s a whole nother episode. But and anyone who’s ever met the indomitable, Catherine Gray knows that she’s a force of nature.

Wendy Ryan: And so when. She and I met, we were both speaking at a panel for a, a Women’s advocacy summit. And I remember her, you know, following up later and I was on her podcast and ’cause she knew I was an investor and she said I’m working on this film project and have you ever invested in film?

Wendy Ryan: Would you be interested? And I said, never invested in film, dunno anything about entertainment. It’s the one industry I really have no experience with. But tell me about it. And as soon as I learned of what the film was about and, and the mission behind the film, I said, well, I’m in because this film has to get made.

Wendy Ryan: Like in this case I don’t, I don’t care if I make money, it just has to happen. So it felt to me like good stewardship of. My wealth is to make sure this film got made. And that’s how, that’s how I got involved.

Syama Bunten: I love that. I I love that. It was also like a calling, you know, like hire like really, like I don’t know what I’m doing here, but I know I’m supposed to be here and I know that what, whatever unfolds is exactly.

Syama Bunten: You know, so I’m just gonna show up and do the thing that feels like the right thing to do. I love that so much, Wendy. So thinking, you know, obviously we talked a little bit earlier about living long lives and you know what it’s gonna be like when we’re in our early one hundreds. I’d love to fast forward us to this young age of 102, 105.

Syama Bunten: Where you’ve had this prolific opportunity on this planet to change so many people’s lives through not just what you do with your money, but also how you show up in this world. You know, I think that integrity matched with capital alignment is really modeling of a new era. You know, like we, we need more role models like this.

Syama Bunten: But if you could please play for me, in your mind, this vision of legacy and this mark that you’re leaving on the world, what might that look like from this vantage point of your young one? Hundreds?

Wendy Ryan: I think it would certainly, access to capital would be like very easy. You know? So if you, if you are someone with an idea and grit and the motivation to follow that through and the ability to do so.

Wendy Ryan: That no matter how you identify yes, and where you are in the world, you can access the capital you need. And it’s not such a struggle. And we are just not there yet for many reasons. But to me what that does is it democratizes so many things and we know that it’s actually better when more people are economic value generators, right?

Wendy Ryan: And not fewer. And so I really see that as being a big dream because I believe wholeheartedly in human potential and human creativity. I’ve worked with people and people systems my whole career. I’ve seen what people are capable of, both incredibly wonderful creative, out the box thinking, and also incredibly destructive.

Wendy Ryan: Small closed thinking. And I just think that we need more of the former clearly, and the access to capital is probably the hugest piece because that’s the system we have.

Syama Bunten: Yeah, that’s right. That’s right. Well, we’ve spoken so much about different kinds of things with money, investing, money, saving money, what it’s like to not have much of it, what it’s like to have money to change the world with.

Syama Bunten: And what I am most curious about as we sort of wrap up our conversation is around maybe some of the most fabulous or fun things that you have been able to do with your capital recently. What has brought you joy through exercising your capital? That’s a great question. The first thing that came up is we were able to make.

Wendy Ryan: But it’s not so recent. But Al also, around the time I started Angel investing, my husband and I made a, a leadership gift to Notre Dame High School to create the Center for Women’s Leadership. And we did not fund the whole building. Let me be clear people. I wish I had that kind of capital.

Wendy Ryan: I don’t, but just the fact that we were able to make a gift of a size that was considered a leadership gift. And and actually there’s a, a room in that building that’s called the Career and Life Success Center, and it is dedicated to my parents. So it has my parents names on there. And that was probably the thing that I have felt most proud of in a way because it was like, not about me, it was about acknowledging the gift they gave to us and.

Wendy Ryan: My mom volunteered in education for many years after her nursing career. And I know, like she, she would’ve been just, if she had been alive, like she would’ve made the gift, right? Like she would’ve just been all about it. So that’s the thing that I, I come back to is like, okay, even if none of these other investments ever work out, which some of them have, okay.

Wendy Ryan: So I don’t want anyone to think like, oh my God, she’s like, invested all this money and, you know, nothing’s happened. No, I, yes, I have, I have made money. I’m happy about that, but to me that’s almost like the most impactful investment because that’s investing in high school and girls, right?

Wendy Ryan: That’s investing in the next generation of leaders and entrepreneurs and innovators and people that are gonna save the world. And that’s gonna, that there’s so much that happens in that building now that’s just was unimaginable, you know, before it existed. And that’s gonna, you know, when I’m 102, that’ll still be there.

Syama Bunten: Oh my God, Wendy.

Wendy Ryan: Yeah.

Syama Bunten: You’re so good. You’re like, and I mean good, like you’re good on, you know, like through and through in your heart, like you’re a real good one. so happy to know you. I just wish I could give you a big hug. It’s like, so, so beautiful. My last question Wendy has to do around the things that you’re calling in right now, it’s clear even now, more than at the beginning of our conversation that you stand in service for others and you are showing up always as servant leadership and really helping others unlock, have opportunities and see a vision of themselves and in the world that they want to create.

Syama Bunten: But this last question really has to do about what you’re calling in. What do you need right now? How could we support you? What, what could you use a little more of in your life?

Wendy Ryan: Hmm. Wow. I mean, we can all use more grace, right? It just we can. And so I always, I always ask for that first. I think that the second thing is, you know, you mentioned servant leadership and I, I would love to gently correct you that it’s learn lead, lift leadership, because that’s my leadership blueprint, which I don’t wanna knock.

Wendy Ryan: Servant leadership has a lot of things going for it. But one of the things I’m calling in right now is I made the strategic decision to close my business cadra in June of this year. And the reason I did that is because I found that I was no longer swimming in the deep end of the pool when it came to running the business, that it was time for me to jump into a new pool and into my third act.

Wendy Ryan: So I’ve done that. Learn lead lift is still alive and well. And it, it still, I think, has just barely begun to do its good work in the world. I feel like it’s something that, that came to me in all of my experience, and it also encompasses the wisdom of so many other amazing people and leaders. So I think just intention around if people are interested in that, if people can see that there’s synergy between that model and their program.

Wendy Ryan: For example, if you, if you’re trying to develop leaders or founders or investors or what have you yeah it’s just I wanna, I wanna talk, I wanna find out what’s possible for us to create together, because I don’t want. Even though Cadra has gone off into the sunset, I don’t want learn lead lift to go off into sunset because I don’t feel like its work is done yet.

Syama Bunten: Mm. I love it. It’s still, it’s still like holding its torch and creating something brighter and weaving its way through the world. I, I think that’s so beautiful. Wendy, thank you for sharing your spirit, your time, your energy today for being a wonderful role model and example of what it looks like to activate your capital and, and have so much agency and purpose and meaning.

Syama Bunten: It’s been such an honor to have you here today. Thank you so much.

Wendy Ryan: Thank you so much.