FROM DELOITTE AND FASTCO WORKS: Resilience in Reality — A conversation with Deloitte’s Deb Golden and Andy Dunn (Part One)
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Hey, Most Innovative Company listeners. It's Josh here. Today, we have the next episode in Lead Through Disruption, our special miniseries from our friends at Fastco Works and Deloitte. Enjoy. Brought to you by Deloitte Cyber and Strategic Risk, helping your organization drive peak performance through crisis and transformation. So no matter where you're at in your journey, you can move forward fast.

I'm Deb Golden, Deloitte's US Chief Innovation Officer, and this is Lead Through Disruption. As businesses look for new ways to maximize opportunities and innovate in a post-pandemic landscape, some of the strongest leaders emerging are those who've had to navigate and endure professional and personal disruptions in their lives. Through these challenging moments, these individuals have embraced curiosity, creativity, and

and the courage to think outside the box and have reimagined the possibilities of what could be. They've forged new paths and have broken barriers that changed the way we experience the world today and see the potential of tomorrow. In finding their resilience, they've been able to turn these bold moves into lasting change and have inspired others at every level.

In today's episode, you'll hear from Andy Dunn, the prolific entrepreneur, founder and CEO of Pi Labs and Red Swan Ventures, and the chairman of Monica & Andy. He's also the co-founder of Bonobos, a men's apparel brand that made its name as a pioneer in the direct-to-consumer business. These days, he's added author to his resume. Andy's memoir, Burn Rate, Launching a Startup and Losing My Mind,

explores his journey building bonobos while navigating his own mental health diagnosis. In today's always-on culture, this conversation couldn't be more important.

One of the things that I find most inspiring about you is not just your own experience of life events that change literally the trajectory of your life, but the fact that you've been so outspoken about not only your journey as it relates to business in the field that you've been leading from that capacity, but also your mental health journey. And so first and foremost, thank you for your transparency.

Thanks for having me. It's an honor to be here. So as we think about your journey, and maybe you could take us back to the early days. And when I think about early days, I mean, it could be all the way from when you were in university, thinking up exciting ideas that you were looking to solve and how you ultimately got to change your life.

the fashion industry, as we might call it today. And so perhaps when did you first decide you had some problems that you were looking to solve? And where was that turning point for you when you said, hey, there's something I think I really got here? What I remember is actually being really bad at developing good entrepreneurial ideas. I, at some point, felt like I wanted to build something. I wanted to create something

I wanted to work at the, you know, at the earliest stage of company formation. And at the same time, every idea I came up with went nowhere. And so I guess what I was good at, at some point was noticing when someone else was onto something. And I had a co-founder named Brian Spaley, who was a classmate of mine, a close friend, a roommate and a housemate. And Brian had this idea that men's pants don't fit well.

which I thought was a little silly. It was like, well, how are you going to reinvent a category that's, I don't know, how old are pants? 2,000 years old, 10,000 years old, older? I guess it depends on how you define it. And he came up with an amazing product and they fit really well for a bunch of arcane reasons that he figured out. The only thing I brought to the party was the humility to realize that I was friends with someone who had invented something really cool and how could I show up in service to that? And then it was a bunch of quirks

of the story that I ended up becoming the founding CEO of the company and being the one to carry it forward when actually I wasn't the person with the product innovation at the beginning. To the extent that there was anything that I brought to the party vision-wise, it was around the channel.

It was around this idea that the internet would be the primary way that brands would get built, which seems kind of obvious now. But in 2007, it was a little bit more contrarian. And I was excited about that. In hindsight, of course, the internet would be the way that we would be doing direct commerce to the world. But in 2007, you're right, it absolutely wasn't. And so what made you realize that digitizing fashion...

particularly in a place where, again, one could argue, well, we were all going to the balls or we were going to stores or we were going to check things out or we needed to see how it fit. How did you think about the transaction of saying, okay,

the physical ability to go in and see something versus online versus the hybrid of the two of them. Because that's a lot back then, but that's even a lot to think about when you think about transformation. Yeah, it's funny. I'm reading Matthew McConaughey's book, Green Lights Now. More specifically, I'm listening to the audio book.

which makes me feel sad about my audio book because he reads it so well. And I have to remind myself like he's a pretty good actor. And the book is called Greenlights. And it talks about these little breadcrumbs that if we're willing to see it this way, that the universe is sort of leaving for us to follow. And for some reason, I was obsessed with the idea that by being internet driven, you could build a better customer service experience than going through brick and mortar retail stores.

And it was an example of past as prologue. In other words, sometimes if we want to look to the future, we have to understand the past. And maybe it's because I'm wired as a, you know, I was an economics major in college and also a history major. And my dad is an advanced placement U.S. history teacher. And so the breadcrumb was this. Two years out of college, I was working at Bain. This was five years before we started Bonobos.

And I got staffed to spend the winter in Dodgeville, Wisconsin, which was where a catalog retailer named Land's End was based. And so I got to see the power that came with a catalog retailer. And a few things came to mind. One, this pink cashmere sweater. We couldn't figure out how to assort the pink cashmere sweater at the local Sears and Hoffman Estates because there wasn't enough demand for a pink cashmere sweater in that one location.

But if you're aggregating the demand nationally, all of a sudden you can offer more fit, more color, more silhouette, more sizing. And so I remembered that from Land's End and I thought, well, if what we want to do is win on the fit of men's pants, we're going to be able to do more paradoxically if we don't have a brick and mortar store to assort to by aggregating national demand. We're going to be able to offer, let's say, like 35 by 32 products.

And all you 35 by 32 guys out there know that it's a hard size to find. Or if you love...

white denim and you're willing to wear it after Labor Day, not so easy to find. But on bonobos.com, it's always going to be there because we're aggregating demand nationally. That meant we could out-assort J.Crew and Banana Republic in our competition with more sizes, more silhouettes, more fits. And then I remember sitting at Land's End, being in the call center one day and seeing this note on the wall. And it was from a customer to a Land's End customer service rep. And it said something like,

Hi, Elizabeth. Thank you so much for waking me up the morning of my wedding. My bridesmaids wanted to sleep in and my mom was a mess. You're the best. And it just stuck with me as what the heck? Like this Land's End call center rep had such a great relationship with this customer that she called her to wake her up the morning of her wedding, like a wake up call, like a hotel call.

And that stuck with me. And I thought, you know what, we can do that even better in the internet age, because there's going to be better data, we're going to have a better understanding of someone's what they're all about over time. And it was like, well, we know this worked in the catalog era, the internet is going to be so much more dynamic, the internet is going to enable us to personalize the catalog to the human.

of course brands are going to be built on the internet. And so it was looking to the past that lit the future. Well, you certainly were a visionary ahead of yourself if you think about where direct consumer and fashion has come from too. So you definitely were ahead of where the world was, but certainly the world was ready for it. And I believe in one of the quotes I've read, you've talked about startups being a collision of fantasy and reality. And I love that thinking, but also the fact

but it's incredibly humbling. And to the point you made, not only about the breadcrumbs, but also being able to understand, and you mentioned having lots of ideas and not necessarily always succeeding at them, but how can you continue to do it over and over again? And so as you think about the things that you learn around innovation, as you think about the things that you envision, and then to your point, the ones maybe that you notice of those around you versus perhaps ideas that you've come up with on your own,

Do you have any advice on how to balance what you might see as revolutionary innovation with how do you lead with responsibility? Because if you followed every single idea that you had, maybe you might not have executed on any of the ones or seen the things that others were doing around you. So any advice for how to maybe balance those two? Wow, that's such a good one, Deb. I'll tell you, I'm working on a new venture now. And I would say...

The first two years, we have failed to find product market fit. And it's helped me develop more humility around just how hard that is. It's like one thing to go from zero to one and then another thing to go from one to 100. And I think I was fortunate in that the first time around,

My co-founder had taken us from zero to one on the physical product. I had some work to do to take us from zero to one on the distribution mechanism. And that was really fun to see if that would work. But in our new venture, I had this really great moment. We recently raised money from a storied consumer internet entrepreneur project.

brought him on to be the chairman of the company, and we were having a conversation, funnily enough, down in Brazil, which is where my wife is from. We're on Ipanema Beach in Rio. It's Sunday, and I made some comment about this new venture and about how it's gonna be great for Gen Z. And he went, "Will you stop talking about Gen Z? "We are old men. "We don't know anything about Gen Z.

You need to figure out how to take this idea and make sure it's solving a problem for you because I don't think we can solve problems for other people. I don't think that's how startups are formed. And he gave an amazing example from his background where it appeared from the people that adopted the product that he built, which is now a

$40 billion company, it appeared that they had built it for young people, but actually they had built it for themselves and it happened to be adopted by young people. And it was so freeing to do two things. One, to stop trying to understand people that

I don't understand. And also to have a roadmap for how to make every product decision on the journey to product market fit, because it's like, all right, let me build something I want. And what's really humbling about this, Deb, is like, I should know this because that's what we did the first time. And so it's been fun to see, as you brought up, it's fun to have fantasy and reality colliding again.

Because actually, I've had to unlearn and relearn some things that you would think I would have picked up the first time. And that very much keeps me

I think to your point, the thing that if you could find areas to solve that keep you interested, you're going to be 10 times more vested to want to solve for them because they're things you're looking to solve for. So, you know, I've spent a lot of times with, doesn't matter the age, but any age group, when you think about the, why did you solve that problem? It's usually like, well, let me tell you the story behind the problem I'm trying to solve. And I just find that that gives people so much more

personal energy to want to try to solve for the problem. So obviously you've done that throughout your career. So, you know, again, one of the things when you have to balance is are you trying to solve everybody else's problem or are you looking to solve something that is not only that resonates with you, but you know, it'll resonate with others who are sitting in similar shoes of yours that may not have thought about how to solve the problem differently.

Yeah. And by the way, I'm having some wild orthogonal thought about maybe this is what we need to do in our personal lives too. Like stop trying to solve other people's problems and just be better listeners and ask good questions and focus on ourselves. But we can save the lessons for entrepreneurship on marriage and family life for another conversation. We'll be right back after this short message from Deloitte Cyber and Strategic Risk.

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I fundamentally believe in calculated risks when you sit there and think about particularly

coming up with ideas. And I think if you can see the path, some of it is how do you understand where that calculated risk is? Because if we take no calculated risk, I feel like we're not pushing ourselves or our thinking in ways that help us come to these conclusions on very, very complicated problems. And sometimes it's really difficult to see how to get from A to Z, or sometimes it's really easy, but it means you have to take a calculated risk somewhere in the middle. And certainly as you've already even talked about,

you know, when you think about innovation and being an entrepreneur, a lot of it is about trial and error. And so is there anything when you think about being too risky or how do I know to encourage others to take risks or perhaps listening to others as they communicate challenges they're having and encourage them through your own motivation to be able to help influence them to take calculated risks? Because I think it's something that,

we often don't do enough of because perhaps we're so worried about the failure side of what a calculated risk means. Such a fun topic, risk. I think there's two contrarian ideas that I have about risk. One is that when we talk about career risk, we often think about it with a narrow aperture, which is it's the risk, let's say, financially to not having a steady income.

or it's the risk of failing and that being a setback in our career. And we forget to factor in a third sort of risk, which is spiritual risk.

which is what is the risk of feeling dead inside because we don't love what we do every day? What is the risk of not coming alive in our jobs? What is the risk of not being around people that we love and belonging to cultures that we're proud to be a part of? What is the risk to not developing as leaders if that is our calling or our path? And I think if we were to factor in spiritual risk,

then all of a sudden we can reframe and think about financial risk in a different way. And then I also think we do a disservice often to people who are actually enduring higher levels of risk in their personal lives. And for me, I got to take a trip to East Africa while we were in the ideation phase of different startups. And I had this moment, you know, I was living in a brick house for a couple of days where you dump the cold bucket of water over your head.

And chickens running around the yard and in a country where it's whatever, $2,000 or $3,000 GDP per capita. And I thought, gosh, what an insult it is to talk about risk from a perch like Stanford Business School. Like, are you going to take a risk? You know what? Not really. Even if you go and start something and it fails, you're just not subject to the same kind of risk.

of roof over your head, nutrition, healthcare, all these things that we take for granted in let's call it elite circles, college graduates, let alone MBA graduates, let alone Stanford graduates. And so I thought, I'm actually gonna stop listening to my classmates' assessment of risk and think about it from a more universal perspective. And then, wait, am I doing a disservice to my forebears by not trying to go and build something?

Right. My grandparents who emigrated from Pakistan to India at the time of the partition where two million people were killed. My paternal grandparents who my grandfather was a navigator in a B-17 where two out of three men were killed in his squadron. My grandmother was a surgical army trauma nurse who landed on the beaches of Normandy on day eight. Those people took risk.

They fought in a war. They were refugees. So, okay, am I going to start Bonobos or go work at a venture capital fund? It's almost the wrong way to think about risk if you bubble back. I think that's kind of the first thing.

And then I think the second thing is, I guess it was a Tony Hsieh interview where it's like, what's the difference between a perception and a misperception? But let me just experiment with misperception. I don't even know if it's a word. There is a misperception that entrepreneurs are risk-seeking. And I actually think that a lot of entrepreneurs are willing to take the risk of starting something, but then are very risk-avoidant in order to succeed, right? So for example, in my new startup...

We had an outsourced engineering firm for the first year, and we decided to make a big move for $75,000 out of a million-dollar cash balance, so 7.5% of our cash on hand, hire or retain search firm to find a VP of engineering. Now, was that risk-seeking or risk-avoidant to vaporize 8% of our capital on a search firm?

And I called a mentor of mine, a guy named Mark Laurie, who's an entrepreneur that I admire a great deal. And I said, have you ever done a retained search on like a million dollar cash balance? And he goes, I do it all the time. And we ended up with a woman named Jen Greenwood, who had been at Airbnb and Asana and Hotel Tonight and BuzzFeed and who's a remarkable leader. She's now our CTO and COO.

And the logic was, we're not going to win if we don't have a world-class in-house engineering leader, even if it's less expensive. And it's going to be painful, you know, to move from this engineering firm in Europe over to the U.S.,

Well, what was that? Was that a risky bet or was that risk avoidant? And for me, it was I was worried about the risk of not having hired that person. And so once you've got a venture off the ground, I think you're actually fundamentally looking at all the ways you could fail and looking to diminish risk, which is what leads to action of who to hire, what strategy to pursue, who to raise capital from, how much capital to raise, all of the above.

And I would think because of the fact, too, that you've got a pretty strong vision of the things that you're looking to accomplish, that you can solidify some of that. Because when I think about your first point around specifically all the career risk and how those things change.

Tied together intuitively, people do create their own biases, whether that's in career risk or that's in execution risk as an entrepreneur, you build up certain biases. And so whether that's a bias of I can only live on X dollars a month, could you really? I don't know. Have we ever tested that balance? If there's something more important to you in terms of seeking a

a greater good? And I would argue the same for technology as we think about just the evolution of entrepreneurs, of innovation, of where tech is headed. Can we use tech for a greater good? And I know that sounds really myopic as we think about, of course, technology is going to help us solve really complicated problems, but are we pushing the way that we're thinking about them? Because I often think maybe we ask the wrong questions. So when we think about how risk is measured,

Are we actually really thinking about it, how the risk is measured, or are we asking the right question to make sure we're getting to different outcomes? 100%. And that's where I like to challenge people, like, what's the question we're trying to solve? Because sometimes I feel like we get hung up in, we've already answered it based on something without actually taking a step back and saying, wait a minute, let's ask the question differently. And I think the more...

different types of humans we bring to the table to ask those questions, we're going to start to see different types of questions come up as opposed to biased answers that really help get us to think differently about the challenges that we have. And to your point on personal, what we all love to call grit and experience, I do fundamentally believe that that drives who we are and why we make decisions. And I do think it gives you a different sense of

My mother passed away when I was young, and I personally almost passed away twice in my life. I also come from a veteran family of individuals who have lived and also those who have migrated into this country. And so when you think about the lives that we lead today,

In general, it is very privileged. However, it's those experiences that you can decide how you want to invoke, how you live your life is what's going to be, what's going to impact, I think, the view that you have and that you bring to the table. I totally agree. Yeah. And often, you know, and thanks for sharing those anecdotes on your side. What I've noticed is when we have faced issues that are higher stakes, right?

which tend to relate to things like living and dying and health. You know, we don't have anything without our health. My mom's always reminded me of that. When we have faced more existential risks

than those that might face a corporation that we're a part of, right? The Limited Liability Corporation was a good invention, which you read about, I read about at the beginning of Yuval Harari's book, Sapiens, and actually how brilliant it was that we created a structure where you could totally bungle something up and not endure financial ruin.

Those risks to our health and our livelihood, our very existence, are so much more profound that if we have been, I don't know how to say it, but on some level, at least in some circumstances, I feel this way, fortunate enough to have been through really formidable personal health crises, then all of a sudden, actually, the hard stuff at work gets reframed. It's just not as hard. It's not as bad. The stakes...

are different. And I'll tell entrepreneurs sometimes, because I've gotten a chance to back a lot of entrepreneurs, hey, just remember, it's just work. It's just business. Everyone's going to be okay. Your team is really talented. They're going to find jobs. Your shareholders, by the way, this is one of my favorites, your shareholders are already rich.

Otherwise, they wouldn't be shareholders. They're going to be okay. So the only person I'm worried about is you and your sense of self-worth. And that's a real thing to think about. So I'm with you on the importance of cultivating grit and resilience and how frequently that often comes from other domains. And I think the more we can try to figure out how to, like your word, cultivate that, because...

I will take grit and particularly resilience any day over a book resume, meaning like you came from X college or you went to X graduate school, et cetera, because I do think you get a different sense of not just your own mortality, but again, the things that drive you, which potentially are very different than,

I'm just being driven by a paycheck. So obviously having compensation may be an important factor for many different reasons. But again, I think having resilience and different life experience truly does just, you come to the table with a different perspective on how you approach a problem. I mean, for me, I look at things and I'm always like, well, why can't we solve that? Like the positive and the negative to that, right? The positive is I think of things very vastly and I say, we absolutely can solve that.

The negative of that could be like, I'm pushing up a hill 24-7. So how do you figure out how to bring the things along that you need to? And at some point, every complex problem you have to decide might not be able to be solved. And so I think to have those different vantage points come to the table, because I just think in the world that we live in today, the problems are only going to become more complex.

And so the ability to perhaps string together different fields of thought based on resilience, if there's a way that we can figure out how to teach that, I think it'll be great. If there's a way we could pull on that thread a little bit. Totally. It's a hard one to teach, right? Life has a way of teaching it to us that's hard to transmit without life doing so.

Wow, there's so much to discuss with Andy. One episode truly is not enough. So head over to part two to catch the rest of our interview. We cover more on the intersectionality of mental health and leadership, talk about the critical role neurodiversity plays in innovation, and discuss Andy's commitment to shift the way mental health is perceived and addressed in society and in the boardroom.

Lead Through Disruption is produced by Fasco Works in collaboration with Deloitte Cyber and Strategic Risk. Our show was produced by Avery Miles and Matt Toder, as well as editor Nicholas Torres. We'll be back with more incredible stories from disruptors who are positively impacting change in business, culture, and society. We hope their journeys filled with curiosity, courage, and resilience inspire your own as they have countless others. I'm your host, Deb Golden. Thanks for listening.