Title: A Serial Tech Entrepreneur who Empowers Others to Grow: Debbie Madden '96

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[00:00:06,840] CHRISTA DOWNEY: Welcome to Engineering Career Conversations. I'm Christa Downey, Director of the Engineering Career Center at Cornell University. 

[00:00:14,780] TRACI NATHANS-KELLY: And I'm Traci Nathans-Kelly, Director of the Engineering Communications Program. We are excited to bring you this forum where we will host lively conversations that we hope will inspire you. We are happy to have Debbie Madden today. She's a Cornell Engineering graduate, ORIE, 1996, and she is a serial tech entrepreneur, the founder and chairwoman of Stride Consulting, an  Advisor at Docker, Inc., author of Higher Women, and two time Inc 500 CEO. She is a mother, wife, and breast cancer survivor. Debbie has built and scaled five tech companies from the ground up, and she's been CEO of three of them. Debbie is a sought after speaker and writer, having appeared in Harvard Business Review, Inc Magazine, Forbes, CNBC, Huffington Post, Varney & CoTV and more. Debbie, we're so glad to have you here today. 

[00:01:11,419] DEBBIE MADDEN: Thank you. It's great to be here. 

[00:01:13,400] CHRISTA DOWNEY: Debbie, it's clear you've accomplished a lot in your career. Can you please take a few minutes and tell us more about your path and what draws you to new opportunities? 

[00:01:22,970] DEBBIE MADDEN: Sure. As you mentioned, I am a serial tech entrepreneur. And I call myself the Accidental Entrepreneur because I never set out to be. When I was at Cornell, even in my first job, I worked for one of the biggest companies in the world. I never thought I'd be where I am today. I fell into entrepreneurship accidentally. I got a taste of it. I worked for a very large company, that was Kraft Foods and that is now Mondelez. And oddly, it was actually using my ORIE degree, it was operations research, it was industrial engineering was exactly what I thought I was going to do with my career. And three months in I was like, This isn't for me. And I didn't know why, but I knew it wasn't for me. And then ever since then, every other job I've had, I've either created a business or worked for a very small start up. I think actually knowing what the other side of the coin was actually helped me really be at peace with this idea of entrepreneurship. Because entrepreneurship is scary, it's messy, it stinks, it's exciting, it's so many things all at once. And I think I would have never had the confidence in myself hadn't I worked for a large company first. So that was one thing. I knew for me what not good would look like for me, even before I knew what good looked like. And then from then on, literally since 1999 I think, or no, 1997 so it's been a while. I've been really drawn to this idea that the scarier, the better, the more unknown the better. The more complex the road ahead, the better. And really kind of found that I am at my best professional self when I am solving problems that I myself don't believe I can solve. Not that aren't solvable, but I wake up and I go, I shouldn't be here. Why am I doing this? Who's trusting me to do this? But for some reason that gives me energy and that gives me drive and I succeed in that environment. We could talk more about that, but it took me a while to learn that that was true. 

[00:03:42,029] CHRISTA DOWNEY: I love that. How do you translate that for the students as they think about next steps and the possibility of some day becoming an entrepreneur? 

[00:03:53,929] DEBBIE MADDEN: Over the last especially decade, there has been a lot of sexiness built around this idea of entrepreneurship. So I think a lot of people say, oh, well of course I'm going to do that, of course I'm going to try that. But then we realize that, number one, you're not born knowing how to start businesses. And number two, I think 99.6% of startups fail. It's not the thing that most people want to do nor should do. I think what I realized early in my career and what I mentor young engineering and other graduates on, is the fact of every opportunity you have in your life and your career I find is best viewed from no matter whether I think I'm in the right spot, whether it's perfect, absorb the good, the bad, the unknown, the stuff you like about it and the stuff you don't like about it. And just really lean into the experience of the path. Because I think a lot of people say, oh, well, I'm going to be an entrepreneur, so I don't need to know how to become a software engineer. Oh, I'm going to start a business. So I don't need to know how to run the back office of the business. And my advice is, take every team you work on, every boss you work for, whether it's good or bad. Appreciate the learning. To this day, and I graduated decades ago. To this day, one of my most valuable lessons that I use in my career actually came from Cornell. I was in a course where we had to break into teams of four. And we had a semester long project where we had to start a business. I think it was the best I ever did in a class in my four years at Cornell. And it was because the team was a high performing team and the four of us just, we gelled. We divided and conquered. We showed up for each other when we said we were going to show up, we pulled our weight, we asked for help, we did all of the things that today I measure a good team on. At the time, I didn't know why are we doing so well in this class? Why is this so easy? When none of us have any knowledge or experience of what we're doing. And the reason why I knew that is because then the next semester I was paired with a different team. And we did terribly. And then I was like, wait a second. What was special about that very first team that I was on? And no one told us to behave that way. We got lucky. And to this day, I actually keep in touch with one of those folks on that team and we reminisce about how amazingly wonderful that opportunity was at Cornell Engineering where we got that chance to be on a team starting a pretend business, 

[00:06:38,450] TRACI NATHANS-KELLY: An immediate follow up. As I think about this, I have a lot of teams in the classes I'm with this semester right here at Cornell. I loved your words about absorbing everything that's going on around you. You identified that you had a really good running team. You jelled, everything was done fairly, then you had a team that wasn't quite so great. Well, now that you apparently are the master of all teams, because it sounds like you just enjoy them so much. Can you highlight for us what makes a really compatible team member? 

[00:07:13,329] DEBBIE MADDEN: There's lots of things and actually there's so much written about the power of a good team. I have actually talked about this in lectures that I've given over the years because any entrepreneur knows that VCs, private equity, anyone that's going to finance your crazy idea, they don't really care about the idea, they care about the team, right? Because it really is the best teams that win, not the best ideas. And you can look at any industry, you can look at any social media giant, any retail giant. You can look at their team. And it's not just the head of the team, it is the team. The best teams truly do win time and time again. And Google actually paid tons of money. I don't know how much, millions, to actually answer this question over years, and psychological safety was a big factor. Do I feel that I can show up and speak my mind and be myself, my real self, my warts and all, self and be a respected member of this team. When I have a dissenting opinion, is that incorporated? Does the team do things like disagree and commit? Which is critically important? Which means, listen, I do not agree with you and I'm going to commit to the path forward truly until we find that that is no longer the best path, right? It's this idea, teams cannot disagree and commit if they don't trust each other, if they don't feel safe. And how you get that team, we talk a lot about diversity, which is a whole thing that we could do a whole other podcast on. But it's not true that having a diverse team means a good team. It's also not true that a homogeneous team makes a bad team. You can have a team of ten that look like me, right? Middle aged white women from New York. And we could be a great team, or we could be a bad team. You could have a diverse team, different races, different ethnicities, different values. Could be a bad team. Could be a good team. That key is that you have to feel safe to show up as yourself. Dissenting opinions have to be heard so that you can disagree and commit and move forward. Or else you just, we've all been on teams, whether it be a sports team or a project team for Cornell, or a family even, is a different type of a team where you either have the same conversation over and over and over the same disagreements over and over and over, even in relationships. Or you feel we're really good at solving problems, we're really good at moving forward. And you can be a tech team, you could be any type of team in the world. It could be, again, a two person relationship, a family, a team for a school project, anything. Those are what I've observed and that is what I've read and I do a lot of reading because that's how you learn. 

[00:10:24,059] TRACI NATHANS-KELLY: I loved that nugget that you had right in the middle of there and I wanted to amplify, when you said that, it's not the idea that it's the team. I can't emphasize that enough. I always teach using the same Google study outcomes. There's two things. Be nice and listen to each other. That was really what they came up with and they admit that they expected much different outcomes than that. 

[00:10:54,309] DEBBIE MADDEN: I think the thing that people misunderstand, because they sometimes don't take the time to ask is the outcomes of this Google study, and of all successful entrepreneurs and successful business folks, is we don't talk about these things because it's nice to have nor a fluffy thing. It's actually tied to outcomes. It's tied to measurable dollars and cents and success. And whether you measure that by happiness, by health, by money, by status. Regardless of how you measure your own success and your team's success, having a high functioning team is a measurable outcome. It's not just a fluffy. That's a really important thing. 

[00:11:41,669] TRACI NATHANS-KELLY: You're singing my song, you're singing my song. 

[00:11:45,510] CHRISTA DOWNEY: Absolutely. I agree about the high functioning teams for sure. Then thinking about your work, what's the broader vision you're working toward in your career? What type of impact are you hoping to make? 

[00:11:57,150] DEBBIE MADDEN: I ask myself that often and two things. Number one, as a human being, I have a very strong personal value driven compass that wants to answer that question. To say, I think it's important that I do right by everyone that I interact with whether or not any other human being will ever find out about the conversation that I'm having. Right? And how this turns out is if I'm having a conversation with one of my employees and they ask for a raise, I tell this as an example all the time. What I'm not going to do is I'm not going to give them more money that is then going to be viewed as unfairly to any other employee should they find out one day, regardless of whether I think they may or may not find out. So I'm not going to cut corners. Whether that be, again, like bringing you back to being a student. Whether that be treating a classmate unfairly, giving someone an unfair grade, giving someone an unfair advantage, even if you think it's going to stay between the two of you. So the impact I want to have is that virtuous circle of treating people as if every single conversation I'm having is going to wind up on the front page in The New York Times. And whether I think it's going to be a difficult conversation when the whole road finds out about it, it's still defensible, right? So that's the impact, number one is like really use that because if you show up in private like that, then I think that will set the tone and model the way for others. Right? And this is how I interact with my children, with my husband, with my friends, everybody. Then from a business perspective, this ties into my business Stride Consulting. We build software products, we create custom web applications, mobile applications for the world's biggest brands. We build the technology for Disney, for Pelaton, for Spotify, for IBM, for NBC Universal, all these wonderful brands. But why we do it is because we do want to have a positive impact through engineering better systems. And again, it starts with people. It starts with having the conversations one on one. Then it ends with the big, broad impact. We are a national organization. The bigger we get, the longer we stay in business, the more tech teams we touch, this idea of building software to unleash the power of the companies that are having a positive impact on the world. We want to be like that tool inside that gives you time back, those cycles back, to have those personal conversations. To put product into the world quicker, more efficiently, to have better outcomes. It's all connected in this weird way because the more and more technology is at the center of the world, whether it's through AI or Chat GPT or machine learning or software engineering. You can use those skill sets for good or for bad. There are people using them to drive bad outcomes, like misinformation. I think today's students are so critically important because they're the ones that are learning the future of all this technology and these toolings. If I run an engineering company today that impacts IBM, Disney, clean energy, education, health care, mental health, all these tools and things that we touch. How can I use efficient software to make those things have bigger reach? That's what excites me, that's why I stay in technology. 

[00:15:55,139] CHRISTA DOWNEY: I love that aspect of it's sometimes behind the scenes approach, you're having impact in so many ways and touching people's lives in ways that might not be obvious, but it's a huge impact. I'm curious then to know who have been some of the most important partners and collaborators over the course of your career? 

[00:16:13,379] DEBBIE MADDEN: When I'm asked that question, my immediate response is it's not that there has been one massive influential collaborator, but rather the world is my tutor. There was a movie and I can't remember the name of it, about this woman that was studying for a spelling bee. And she was really stressed out because she didn't have all the advantages that all the others had. She didn't have money or resources. And she found this tutor and the tutor said like the whole world's your tutor. Every single person that you interact with can help you achieve this goal. And that is how I've lived my life. Every conversation I have, every person I interact with, whether it be someone 20 years my senior or 20 years my junior, I really, I go through life taking these mental notes. It's funny, like I tend to instantly and unconsciously put people into two buckets. Either I can learn from that person or I want to spend not so much time with this person because they put toxic energy into the world. And they're not open, and honest, and vulnerable. And it has nothing to do with their intelligence, it has to do with their attitude. And most people fall into the former. For me, it's been those small moments, those comments that people have made throughout my life. And sometimes it's with people that I barely know that say something and I say, oh, I'm at a crossroads and you just helped put me on the right path. I will also tell you that if anyone listening doesn't have a mentor in their lives, that is not someone that you need to pay, that is not someone that needs to have more experience than you. Ideally, it's someone that's different from you in some way. If there's one thing you take away, please go find one. And oftentimes, the best way to find a mentor is to become one yourself. And it could be going out to lunch with someone, helping someone study for finals, helping someone get that first job, helping someone study for an exam. It doesn't have to be a big lift. And it's the mentors in my life that have been the most important collaborators in my career and in my personal life. 

[00:18:39,490] CHRISTA DOWNEY: We're always talking with students about mentorship and the importance of it. That's fantastic. What would you say has been the most significant challenge you faced in your work? 

[00:18:49,190] DEBBIE MADDEN: You had asked me this question in advance of today and I read it and I'm going to tell you what first popped into my mind. Because then I tried to zoom out and answer it in a different way. And then I kept coming back to this answer. You mentioned at the top of this conversation that I'm a breast cancer survivor. So when I got diagnosed with breast cancer, Stride, my business, I'd only just started the company. And it wasn't my first business I'd started, but it was only a year in and it was very small, a dozen people or less. And here I am facing a year long treatment. And I had two young kids and, and I was about to go through chemo and I was like, oh boy, this is going to be tough. The interesting thing about what I'm telling you, which I realized while I was going through it during that year which was seven years ago now. And by the way, I'm fully cured and fully healthy. So happy ending. The hardest part was not my own treatment because maybe it's my entrepreneurial like, let's go get it brain. That I was like, okay, we have a plan, let's go. We've got this. And my doctors told me this is highly curable, you're good. That was not the challenge. The challenge was actually, I'm A-type person, right? And I'm an entrepreneur and I like to like stand on a wall and tell people, we got this, follow me, I'm going to protect you. And now, I needed the help I needed to let go. I needed to delegate. The single hardest thing I've done in my career is actually learning how to truly and holistically delegate everything, all at once, with no opportunity to really take back. That was the hardest thing. My team was junior, my kids were young, my company was brand new, and I had to be like, all right, executives at my tiny little business that I didn't know if I was going to make it through, you've got to run this company now. They were like, what are you talking about? We can't do it. You can do it. And to my kids, they were in like elementary, grade school. I said, you guys have to get yourself up in the morning. You have to make lunch for yourself. You have to do your own homework. They were like, wait, what? We can't do that. And I was like, I'm going to be right here, but I'm going to be not doing those things for a while. And so I had to completely let go of everything all at once. That was huge. And seven years later, one of the best things that's ever happened to me in my entire life was being faced with that. Non negotiable. If I wanted all of the things, this was my path to it. It was the scariest thing. Scarier than starting my companies. Scarier than going through chemo, scarier than having kids. Scarier than all of that. And I've thought about this, it's is not just an off the cuff statement, but truly letting go in order to embrace that fear and achieve what I really in my heart, wanted to do. Impossible, terrifying, and the coolest thing. Because I saw people grow in a way that I wasn't enabling them to grow by controlling more. And my kids were ready, my team was ready. They did it, they did it and that was the coolest thing and made me a better person for it. So it was really great and really hard. 

[00:22:32,760] CHRISTA DOWNEY: That's, that's an inspiring story. I'm glad that you are healthy and what great role modeling for your children, for your team, and anybody else who is in your life at the time. 

[00:22:47,310] DEBBIE MADDEN: I want to say one more thing. For anyone that has this in their life or maybe has someone that they think they need to go to when maybe they're ready to expand their wings. Because when you're in college and you're away from home, you are like, okay, wait a second. I'm grown up now, I have fend for myself now. I distinctly remember the morning that I regained the strength to make breakfast for my children. And I remember clearly, because I went up into the kitchen and I went to do it for them, but they were already doing it. And I said, wait a second, I am not going to make breakfast for my kids this morning just because I can. I'm not going to, because they don't need me to do that for them anymore. But yet I was ready to just jump right back in. And I literally sat down and had a cup of coffee. And I sat next to them and they didn't ask me, didn't even need, they were happy to talk to me. It was so cool. Like I think if I would have just jumped right back in and made the breakfast, we would've gone back to old habits. And it was just a really cool moment where, especially you're in college a lot is changing, you're thinking about your future, you're growing into who you are as an adult. Sometimes you have it in you, even when you don't realize. That was really cool. 

[00:24:08,450] TRACI NATHANS-KELLY: We talk a lot on this campus about leadership and followership that goes with it. But I think that this is really an extraordinary flavor of leadership. To lead is sometimes let go. And give other people the chance to shine, to empower themselves, learn those skills, even if they're kids cooking breakfast or it's your whole team trying to run this business that your leadership moment was saying I'm going to trust all of you. It's funny because I had read all the books. I thought if you had asked me seven years ago, am I good at delegating, I would be like absolutely! But not so much. I wasn't. I wasn't. It's also like that relationship between what are those internal things that you can control combined with your external realities like where do you fit within the world that influences how you show up. Sometimes that's saying, like when life gives you lemons, make lemonade. Sometimes those external forces are opportunities. Not always, sometimes they're just bad things. Not everything's an opportunity, but sometimes you can really take advantage of external things that you can control. 

[00:25:24,909] TRACI NATHANS-KELLY: One of the things that we are asking folks that we're interviewing is to go into a time machine. These thoughts about leadership and taking your chance and finding your place and trusting yourself. But time machine we're asking them, what would you advise when they were sophomores that's just on the cup here at Cornell of declaring your major. And being a little bit more official about those intentions that you have going forward. It's probably hard, it's hard for me to remember back when I was a sophomore, but given that general flavor, what do you think might be some good advice for those students? 

[00:26:03,109] DEBBIE MADDEN: Yeah, I really love this question and I appreciate you asking it, because when I was a sophomore at Cornell, I do have a very vivid memory of the way I felt in relation to my peers. And I was a smart, successful high school student like everyone at Cornell Engineering. And then I got to Cornell and I instantly felt lesser. than. It wasn't because of anything anyone said to me. I looked around and I instantly felt I definitely had a little bit of imposter syndrome. There was definitely not that many women. It was a very male dominated school at the time. And I know Cornell Engineering has done a lot of work and made a lot of progress and equities of many kinds. And even back then in the '90s they did as well. But the reality was in my classroom, I looked around and I said, I don't look like everybody else here. Most of my peers are men. That gave me a little discomfort. And then further, a lot of folks in my classes were smarter. They were a lot smarter than I was. And they put in a lot of work studying all hours a night, on the weekends, and really understood a lot of the material. Again, right at that sophomore year is when I think was the hardest, because it's before we really broke out into majors and we were in those big, giant classrooms with hundreds of people or dozens of people. And I felt scared. I felt alone because none of my friends, like the folks that I live with and the folks that I spent time with, none of those folks were in engineering. So I was, you know, everyone else was writing essays, I was doing problem sets. You know, it was very this is going to sound funny, but in 1992, I think I was the only one I knew that had a computer like everybody else didn't. 

[00:28:00,530] TRACI NATHANS-KELLY: I feel that deeply. Yeah. 

[00:28:02,350] DEBBIE MADDEN: Like I had to go to the Cornell Engineering Computer Lab to do all of my work, so I couldn't even like all my friends who had like the library like writing. And I was like, well, I got to go to the computer lab. That's where my work is. And so that felt lonely. I just felt different everywhere I looked. I couldn't bring the computer lab to the library, it didn't exist back then. I couldn't make myself into different race or gender. I couldn't do that. Looking back now, I know that, you know, what makes me happy, what makes me successful is my grit, is my humor, and is my empathy. It's not the color of my skin or who my friends are, even my intelligence. My favorite peer groups are the ones that I'm constantly learning from and feeling like I'm getting from the team and giving to the team. And you have to surround yourself with people that are smarter than you in order to grow. If you're listening and you're at Cornell, whether you're a sophomore, freshman, sophomore, junior, or senior, find the courage to have that confidence even if it's in small pockets. Even if it's a little bit, even if you're scared, even if you don't have it all figured out. Like I still don't have it all figured out and I'm in my '40s, that's okay. And there is a lot of support and you have so much time. That's time, so much time. And there's so many paths where you can be happy, you can be successful. There is no one right answer. So really show up as a good human being and it goes back to that team, do what you're saying you're going to do, show up for people the way you tell them you're going to show up. And it's okay to be unsure. It's okay to be scared. It's okay to feel like you're not the smartest person in the room. I'm not even close to the smartest in the room. And it's been okay. And it's been more than okay. It's been great. It's been so great. The other thing, the last thing is to this day, my very best friends I met at Cornell. I met my husband at Cornell. My sister went to Cornell, she met her husband at Cornell, all four of us. We met our spouses our sophomore years. It was a big year for all of us. Not to scare anyone, but sophomore year at Cornell was a big year. No pressure, no pressure. 

[00:30:46,030] CHRISTA DOWNEY: Okay. So we're going to wrap it up with a speed round. Are you ready? 

[00:30:50,370] DEBBIE MADDEN: I'm ready. 

[00:30:51,410] CHRISTA DOWNEY: Okay. Debbie, what do you do to relax, have fun, and re energize? 

[00:30:57,229] DEBBIE MADDEN: I love to exercise. I love to lift weights. One of my favorite things to do is playing strategy board games, we play with my family. Anyone listening out there that likes board games, El Dorado is my current favorite. Those are some of the most energetic ways I do to relax, things I do to relax. Yeah. 

[00:31:15,709] TRACI NATHANS-KELLY: What's one place you go for information to stay current? 

[00:31:18,629] DEBBIE MADDEN: Interestingly, podcasts. I listen to a lot of podcasts of all different types current on business, fitness, mental health, anything from Freakonomics to The Daily to the Hidden Brain. I make sure to listen to podcasts across discipline. As I'm exercising, as I'm walking, as I'm having my morning coffee. Yeah, I love it. I absolutely love podcasts. 

[00:31:45,569] CHRISTA DOWNEY: If you were not doing this work now, what would you be doing And which is closest to what you dreamed of when you were a child? 

[00:31:53,010] DEBBIE MADDEN: When I was a kid, I never had like I'm going to be X, I never had that. But I always thought that I would work with children. So I always loved kids. Like little kids, my parents always thought I was going to become a Dr. or a pediatrician, which I think that time has passed. If I wasn't running a tech company, I would probably be doing something to mentor kids. Because a lot of what I'm talking about really starts with helping kids feel confident in their place in the world. And that has a lot to do with their environment and where they feel safe to fail. And I think one day I probably will spend more time with that in some shape or form. I don't know how yet. But still to this day, it does give me joy. Just just working with children from all over and all different types of kids to really give them that, hey, listen again, I felt different parts of my life. You might not, you might, and either way, it's okay. And what gives you joy and where do you feel safe? Maybe one day we never know, we'll see. 

[00:33:01,269] TRACI NATHANS-KELLY: I have no doubt you will figure out exactly the right way to go with that dream. I love it. We appreciate having you here today. My gears are spinning in several different ways right now and I just really find your outlook about how to work with other people and showing up authentically and fully for your teams, it's just so wonderful. Inspirational. Something that you can really build with that should be a cornerstone. 

[00:33:30,219] DEBBIE MADDEN: Yes, absolutely. And anyone could do it. I just want to say I have had and always will have a real love and appreciation for everything that Cornell gave me in my life. And the memories, some of the fondest memories, problem sets and all. I loved every minute of it, looking back. Thank you for having me. It's been a real honor. 

[00:33:52,540] CHRISTA DOWNEY: It's been an honor for us. Thank you so much. Thank you for listening. If you are enjoying these conversations, please follow, write and review on your favorite platform. Join us for the next episode where we will be celebrating excellence and innovation among engineers whose impact contributes to a healthier, more equitable, and more sustainable world. 

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