Transcript — S2E4 — A Weird & Wonderful Gift

Rhyd: In today’s episode, I’m talking to Debbie Madden. Debbie’s the founder and chairwoman of Stride in based New York City. Debbie, thanks so much for joining me today.

Debbie: Yeah. Anytime. Happy to be here.

Rhyd: Debbie, what are you rethinking about at the moment?

Debbie: Like many, I run a tech company and the marked shift between the relationship between profit and revenue is very real. And so I’m thinking about that. How can Stride as a professional services company be the most valuable, the most relevant to our clients when growth at all costs and market share at all costs has been replaced, at least in the short term with growth, so long as you’re profitable? So that’s what I’m rethinking about every day.

Rhyd: Every day! Wow okay, so are you finding at the moment that the economic conditions are tough? In the UK there’s cost of living crisis, and. I’m sure in the US there’s talk of the debt problems with the Senate and the President. So are you finding that people are watching their outgoings and they’re struggling or people are investing?

Debbie: So what I’m seeing is finally I’m seeing a movement in innovation. But what I was seeing for about three months was innovation was coming to a crawl where people were thinking very near term and solely about efficiency gains. And usually there’s a healthy mix of efficiency and innovation and the balance was—I’ve been working in tech for 25 years and I’ve never seen it—this drastic shift towards thinking about efficiency 95% of the time and thinking about innovation 5% of the time, which is not sustainable long term. But finally I’m seeing… And these numbers are, I made these numbers up so… outta all of the thousands of conversations I’ve had with tech leaders, but finally the conversations are shifting. So I’m seeing a 10 to 15% shift back towards innovation, medium long-term thinking. It’s still the majority about efficiency, which I think it will be for some time, but I think the balance is becoming a little bit healthier, and I hope that trend continues.

Rhyd: Let’s hope so that’s definitely good news. Is that all from the result of the after effects of the pandemic, do you think? Or was too many? Is that too simplistic?

Debbie: I don’t think so. I think the people had come back towards more innovation in 2022 and now in 2023, and I do think the Silicon Valley bank situation shifted. The relationship between the money and the innovation and in a way that still isn’t done. We’re still in the middle of this and nobody has a crystal ball. But I think the relationship between private equity and venture capital even for enterprises has really been the current catalyst, if you will really focusing on making the fundamentals of a business more long term healthy, which means making profit in the near term. That’s those, and that is based on, again, that is based on hundreds of conversations that I’ve had, things that I’ve read, things that I’ve listened to, people that I’ve spoken to across industry. So I think it’s more that than the come, coming out of the pandemic. But people are, were wounded, but they were healing from that. But before they were fully recovered, they were hitting with the one two punch. And so I think that is what I’m seeing stifle a lot of innovation. But again, I am seeing it start to have a little bit of life, which is really encouraging.

Rhyd: Yeah, it’s really positive. Show your the founder and chairwoman at Stride, what’s the hardest thing about being, the founder of a successful company that listeners might not realize, do you think?

Debbie: So I think that, people ask me a lot about, tell me about why you founded Stride. Tell me about, did it, did the success surprise you? Like, how are you feeling about the future of the business? And the thing that I think confuses people, surprises people is two things. Most days it’s about just doing the thing to get you through the day. There’s a lot of stress for me personally. And the other thing is that people don’t understand or not understand, but people don’t realize the enormity of that. I’m not taking a million small bets all the time. I’m taking one or two outsize bets and then in every other area I’m act of my business. I’m actually being quite conservative, right? I’m not taking outsize bets on the salaries or benefits I pay my employees. I’m not taking outsized bets on the clients I work with. I’m not taking outside bets on the number of innovative products we have at Stride. I’m taking one large bet that I’m running privately held business that’s gonna succeed. That like there really, that really is one enormous bet. And I’m betting pretty heavily on that, but everything else underneath that to support that bet is actually very sound, actually very conservative and something that, that needs tending. And a lot of TLC every single day in very small ways. And many people do understand this, but it’s something that is worth pausing on and reflecting on, because that’s the hard part to make is those micro decisions that you make every single day.

Rhyd: So you were a CEO in the past, and you’ve handed over. Is it, do you find it difficult not to try and step in and let the CEO run it?

Debbie: Oh yes. For people that know me, they’re having a large belly laugh at that question. I yes, let letting go and truly delegate, delegating with autonomy to people that I truly trust and are truly brilliant and amazing in every way. Still as a founder of a, again, stride is still relatively small and we’re privately held and because I care about it, because I love the people and love what we do and love the business so much. I’m very emotionally involved. And as the founder, I’ve made the the choice to step away from the CEO seat. And it was for me and for the business, the right decision and continues to be. And so any hesitation is just something that I need to work on. Nothing more than that.

Rhyd: So Debbie, what event made you pause and rethink your approach to work life?

Debbie: The one event is, in my case, pretty easy to think of because it was when I got breast cancer in 2015. And it literally was a forced and very acute. It was more than a pause. It was your entire life at a momentary standstill. And I’ll share with you a story that, that some folks at Stride know, but not many know. I got the unfortunate call from my doctor, okay, you actually have cancer. And I was, 40 at the time. So fairly young. No history in my family. And Stride at the time was only one year old. It was a very small, young, new organization. And my husband and I were in a taxi on the way to the doctor and I said, “oh my God, I’m worried about the kids”. And he said, “don’t worry, they’ll be fine, I’ll do whatever I need to do”. And then my next thing was “I have to shut down Stride”. I have to end the company that I work so hard to create. And for whatever reason in that moment, he looked at me and he said, “do you love Stride?” And I said, “I do”. And he said “don’t stop doing it”. And that was it. That was it. It was that brief of a complete pause and that quick of a certainty, and we restarted and we never questioned it ever again. But what it did was, it made me rethink the title of this entire podcast “was what does work mean? What does life mean?” And in that moment, I knew in my heart that I loved Stride. And I also loved my life. And from that moment, from that, I remember the taxi cab. I remember the question, I remember my answer and it felt so right then. And 8 years later, fully cured. Stride is thriving. My life is thriving. And I think funnily, if I didn’t have that wake up call, I don’t think I would be as happy in my life or in my business, which is very strange thing to, to realize.

Rhyd: Yeah, that’s amazing. It’s like the, it’s like the perfect answer. I should end the podcast now cuz no one’s gonna beat that. No, I thought you might mention it. I didn’t know, I didn’t want to second guess it, but I didn’t expect almost that almost 10 years ago it happened. I imagine there are lots of people who get that awful diagnosis and must think “stop everything”. But you carried on, you kept your company going. It’s incredible.

Debbie: I did and it’s, it was such a real moment where I was asked a question of all the questions my husband could have asked. Not, “do you think you’ll have the energy? Do you think we’ll have the financial means? What else should you do?” He asked me, “do you love it?”. And I instantly knew that I did. And it was such a weird wonderful gift that I got. And that he got, because all this time later I… The one thing that has changed for me is, and again, what you said is so important… most people you have this like fight or flight instinct and either people get paralyzed, they run away, or they run towards, and I’m the type of person that runs towards my instinct is always to run towards, and that’s what I did here. And so when someone says, “oh, do you wanna go on out to a Broadway play?” “Yes, I do”. “Do you want to take that really hard sales call when someone might be really upset with you”? “Yes, I do”. “Do you wanna walk into that really large conflict?” “Yes, I do”. It’s always I’m it really has eliminated that hesitancy of doing hard things. And I’m, I’ve always done it, but I had never quite done it with such confidence that no matter the outcome, I’m going to love the journey and that is the, that is was the light bulb moment for me that sometimes it’s funny, 8 years later, I do have to pause and remind myself though that I had that moment. I never forget it, but it dims sometimes. Which was unexpected but yeah, really it was really cool and there’s no other way to describe it.

Rhyd: I was gonna say, what does it mean for you today? But I think you’ve covered that, brilliantly. I think the one thing there you said was the fact that you mentioned the hesitancy. You don’t run away from things and certainly, I’ve, been selfish. I’ve done a lot of things where I think, oh, I won’t bother doing that. But maybe that’s, maybe I don’t need, maybe I, no, I think I need to be a bit more like you, Debbie, and perhaps stop being so nervous or hesitant about doing stuff that’s perhaps difficult or problematic.

Debbie: Yeah. I did when I got through all my treatments, I did a triathlon at 43 or I’d never done a triathlon before and I did an open swim in the ocean and that was the one of the top 5 scariest moments of my life, but also one of the best. And I did terrible. I didn’t finish well. I finished, on the bottom, whatever I did terribly. But I like so enjoyed that moment. And it’s just, it just things like that, and again, it’s, it comes back to what we were talking about before about success. It’s not about being reckless. It’s not about being reckless, but it’s about taking a few calculated bets, and doing a couple of outsized things. And then at the same point, I’m not gonna say, “oh, I’m gonna leave my home and be a nomad and travel for the world and, my kids still have to go to school”. So it’s not about being reckless, it’s about taking, fewer larger chances, things that, that, your heart flutters a little bit and then you still move forward. So that’s what it means for me today.

Rhyd: I was gonna say that, anyone who could finish a triathlon, I don’t think you can say did it badly. That’s quite an achievement in itself, right?

Debbie: Oh, yes, I was yes, I was quite slow, but I enjoyed every minute.

Rhyd: Nice. Where were you? What ocean were you in the Atlantic. Near you? Near New York.

Debbie: From the Atlantic. Yes. Yes.

Rhyd: That’s very impressive, Debbie. It’s very impressive.

Debbie: If you saw how slow I did it, you wouldn’t be as impressed, but.

Rhyd: Do you mind if I ask you a question about. If someone else had, listening, has been diagnosed with this a serious illness, what advice you’d give to them?

Debbie: Yeah. No I actually, one of the things that I really enjoy doing today is speaking with people that are newly diagnosed with - Often it’s cancer, but it sometimes can be other things - and because I think there’s sadly two types of conversations that newly diagnosed people have, one with doctors and one with people that just feel bad for you. And I think those are both valuable but I think, the thing that I’ll tell people is “try to find that third type of conversation”, which is, people that are neither that can talk to you with some tough love and some courage and some things that make you opt, cautiously optimistic about your own future. Because I think that once you get that scary news, you’re no longer a number. You are just yourself and the numbers don’t matter. Okay, how am I going to move forward? And then also, like the people that feel sad for you are going to, I got a lot of, people that love me saying, you’re not well enough to do X, Y, and Z. Oh, you don’t wear yourself with A, B, and C. And to, to me, that wasn’t helpful. I much rather prefer the Okay, do you think you can do it then do it, and if you can’t don’t. And I went trick-or-treating with my kids during Halloween while I was doing chemo, and turns out I couldn’t do it. And I swear on my life, I sat down on the streets of New York City cause I couldn’t continue walking. And all my kids remember is that I went trick-or-treating. They don’t even remember that. I was like, you don’t remember that? I couldn’t make it. They’re like, no, what are you talking about? They have no recollection. And and I, that’s that, that’s my advice. Like there are no, rules like, of oh, Have to do this, can’t do this, should do this. You do what you can and no more, no less, and that’s if anyone’s listening and if, if you’re going through this please do reach out because I really do love having that, that, conversation type three or something better that I feel like has a book title in there. I don’t know. You can think about it after this.

Rhyd: That’s brilliant. Thanks Debbie. That’s such a perfect answer. You took me aback there.

Debbie: Thank you.

Rhyd: You’ve been working in, in technology for 25 years running Stride since 2014. How did you get started? Where did you start at?

Debbie: I did actually go to college for engineering. the nineties, so it wasn’t software engineering. For those that are young, we did have computers at college then, but I did go to school for engineering and instantly fell into this at the time somewhat, path-less travelled, which was, I loved being around technologists, but I did not like being a technologist. And that was that was hard to navigate cuz there weren’t a lot of scaling startups back then. There were, but not like today. And so I very quickly found ways that I could be around technology helping with the business of running business that, where technology was a key differentiator. And then started very early on, on an entrepreneurial spirit. Some by accident, some by intention. And it was actually my husband that, that started being an entrepreneur before I still had a, a day job, if you will. And he got me hooked on this idea of entrepreneurship, and I really found a taking to it and then started. Matching up, finding problems, solving them, finding bigger problems, making mistakes, and I just really love that, that that uncertainty, the unknown. That that messy middle between ideation and success. And so just kept, and I’ve scaled five companies. Many have failed, some have been mediocre. Stride is the one that I’m most proud of by far. And so just constantly trying to improve and trying to solve bigger problems than the company before.

Rhyd: For the other companies then were they in consulting?

Debbie: One, one was a consulting company, the one before Stride. The one before that was a DVD delivery business in Manhattan, which lasted for two years and was something I had no business starting and. We never made any money and we shut down. But I did learn the value of marketing. So that was the big takeaway from that. And prior to that a very short-lived business where we sold, it was like a very early e-com company that lasted about a year and we sold tire repair products. Again, knew nothing about tires nor tire repair. And then before that I was a hired employee for MicroStrategy, a business intelligence company that is a public company to this day and helped grow that in its pre-IPO days.

Rhyd: Nice. Tire repair. Did you just think, I know tires? I People need to fix the tires. That’s it. I’m gonna do it.

Debbie: It was, I don’t I, it was not my idea. I was like a co-founder in the early days and I do not know where the idea came from. Someone said, do you wanna do this? And I said, sounds great. Let’s give it.

Rhyd: Let’s sell some tire repair kits. Oh, I love it.

Debbie: I think, I think that’s the beauty of being an entrepreneur is that, that I have cautious optimism, but I think back then I had just undying unrealistic blind optimism. And I think you need a little bit of that to be an entrepreneur.

Rhyd: What’s the biggest upheaval you’ve seen in that time in the last sort 25 years?

Debbie: The biggest upheaval? I. I know it’s, I know it’s a bit cliche or over talked about, but I really think where we work where you and I are having this conversation from our homes that I think is the largest and most impactful. And I think there are a lot of benefits and I also think there are a lot of negative impacts that we haven’t realized yet. From not being together in one room solving complex problems. And so I think where we work has been the largest and the most impactful that I’ve seen in 25 years.

Rhyd: That’s a really interesting answer cuz I thought you were gonna mention the pandemic or something like that, but actually it’s almost like the after effects of the pandemic.

Debbie: Exactly.

Rhyd: And having been like a long-term commuter into London for many years, quite a long time on the train one of the, you can’t really say the word benefit, but one of the things from the pandemic was that, my commute stopped and that was amazing because of all that time back. But I realized recently is that yes, working from home is possible and I can get a lot done, but sometimes not being with the people you’re trying to work with, it’s actually it’s a problem because it’s just a little bit more complicated and sometimes you just need that spark. Someone to draw something on, a whiteboard, someone to come up an idea there, and then the room. And that’s, that hasn’t been solved. All the digital tools are great, but sometimes the in-person collaboration, you can’t beat it.

Debbie: Yes. So I agree and we can have a whole another podcast on that. But to me, yeah, that, that is the largest one by a lot. And I think a lot of people don’t believe that it is as big an upheaval as I believe it is.

Rhyd: Yeah. And I think the me of 2 years ago would be like spitting feathers, the idea that I was saying we need to go back to the office for, for certain things. But I think I’ve realized that never…

Debbie: And I think the answer is we don’t know what the answer is, but I think this, the dust has not yet settled on this debate.

Rhyd: You wrote a book back in 2018, “Hire Women: an Agile Framework for Hiring and Retaining Women in Technology”. I’ve recommended this book to a number of people. If you were writing the book though today would you, would anything be different do you think, based on what you’ve learned over the last few years or does it still all apply?

Debbie: It the title would be different cause, which is unfortunate for me because I think the content of the book is so much more than a gender debate. And I think that this idea of diversity inclusion and really creating a psychologically safe place for different types of people to work and be heard and be impactful together is really what the book is about and was about under the veil of there’s not enough women in technology. Which, which is, still a relevant topic. However, yeah, I would, I think I would’ve focused more about like really harnessing the power of differences of thought. Cause I think that’s really what it’s all about. People’s life experiences add up to how they show up to their current theme. For how you interact with your friends when you grow up, how your parents disciplined you, how you got rewarded in school. All of these things completely regardless of gender, race, age, where you grew up, but like your actual experiences, your interactions with people of authority around you make you who you are. When you have a conversation, when you debate, when you innovate, when you try something for the first time. And as we build teams and enable those differences of opinions to to come to the surface, that’s how we build great teams. And that is what is the book, but that is not what the title says. And so there we have it.

Rhyd: Yeah I see what you mean and I no, it’s good. And I think one of the things that I realized over the last few years, it’s not just about gender. It’s much more than that. But again, I think a lot of companies say we’ve gotta hit our targets of hiring a certain number of people, of a certain gender, of a certain race. But it’s not about that target. It’s about, as you said, it’s the diversity of thought and the culture of the company that you are involved in having different people and not, middle-aged white men or whatever. It’s having those people have input because it gives you such a better opportunity to deliver more interesting work with more interesting people. And so I think that’s the thing that’s, that people should be focusing on.

Debbie: Yes, and I do think people are the conversation that I have matured significantly over the last, 5 years. And a lot of tech leaders and a lot of tech teams are really putting effort into embracing diversity of thought. So I feel really good about what I see in our industry.

Rhyd: Yeah, same here. I think hopefully there’s more to come and more positive news to certainly to, yeah, to come in the future. And having spoken to a couple of people from movements like Women in Data, women in Tech, is, it’s all worth force for the good, I think.

Debbie: Yeah. Awesome.

Rhyd: and Debbie, you’ve got a podcast you and Stride have released to a few episodes out. Scaling Tech. Tell us more.

Debbie: So Scaling Tech is a fairly new podcast, and the concept behind it is with us—meaning technologists working hybrid and largely remote—we have lost the ability to network as we used t and so if we can’t bring the person to the network, I thought we’d bring the network to the person. And so scaling tech is my answer to that still, and as is this podcast. So it’s really along in the same vein, I think it’s critically important to always be learning from your peers. Of their successes, their lessons learned, and their failures. And so that’s what scaling tech is all about. I interview a tech leader, a first-hand story of something that they have seen, done, been a part of what they could have changed, what they’ve learned, their failures, and it’s been really great so far. So thank you for asking about it.

Rhyd: No worries. I’m enjoying it. I haven’t got through them all yet, but I will do. And what’s coming up next for you, Debbie?

Debbie: I am, I’m really interested in taking Stride to its natural next step. We expanded from New York City to national and we’re really working on yeah, making a national brand for ourselves, right? Many know us in New York City and folks are starting to become familiar with our impact and our work within the technology scenes across the country and across the globe. And I’m having a lot of fun kind of bringing our message of helping make sure your technology process is a true competitive advantage by having non dogmatic yet progressive engineering best practices. So really focused on that. I’m really loving it.

Rhyd: Oh, sounds brilliant. Best of luck in that.

Rhyd: And Debbie, if anyone wants to get in touch with you, what’s the best way for them to do that?

Debbie: You can always go to stride.build, which is the company’s website, and you can also email me. And I do respond to emails. I do love having conversations with people. You can email me at debbie@stride.build. Of course you can find me on LinkedIn, Twitter, all of the things like that. But yeah, the website and the email are the best.

Rhyd: Awesome. Thanks so much for your time today. I really enjoyed talking to you and I was really taken aback by your answer. So appreciate your time.

Debbie: Thank you. It was a pleasure.

Rhyd: That was Debbie Madden, Founder and Chairwoman at Stride. Thanks, Debbie.

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