Marcus Osborne 0:28
Hello, my name is Marcus Osborne, I work for Walmart Health and Wellness. This is a pretty exciting day for me because I’m getting to turn the tables and do something I’ve always wanted to do, which is interview Miss Alex Drane because, those of you who know Alex, she comes loaded with questions and you’re often the one who gets interviewed. But now I feel like this is the one time to do it in reverse. So it’s my pleasure to introduce Alex Drane who is founder extraordinare, including her most recent adventure, ARCHANGELS, which I’m sure we will get into more here shortly. So Alex, thank you for agreeing to do this. I know this makes you wildly uncomfortable. But it makes me super, super happy. What I tend to find in life is this, that if you can understand what really fundamentally motivates somebody, if you understand what truly sort of drives them, you can use that to find value. And you can use that in kind of relationships and partnerships and other things to find value. What is your motivation? What gets you up in the morning? What keeps you going until late to the evening? What is your motivation?

Alexandra Drane 1:47
Well, I love that you say, what keeps me going until late in the evening because often, for both you and I Marcus, that’s the only time we get to catch up because we are never done working, which I think is a foundational part of being an entrepreneur, which is a foundational part of like, what what gets me all fired up. I have this foundational belief that we are all way more alike them we’re different, that the most important thing we can tell each other is that you’re not alone, that shame is just a conversation waiting to be had. There is nothing I like more than sharing something so embarrassing, so horrific, so unflattering about a company that I’ve tried to start, a project I’m trying to work on, a conversation I had with one of my children, something that happened with my man, that went so horribly wrong. And in saying it out loud, somebody else saying, oh my god, that happened to me too, or oh, you think that’s bad? Just wait. And there’s a thing called The Long Dark Night of the Innovator. And I love it. It’s this graph. And to me, it embodies all of it, which is, anytime you think you know something, you almost definitely don’t. And it’s just beginning a process of you getting beaten up over and over and over again. And it turns out, I love that process. That’s part of my thing. And I also think, I’m 50 now, as you know, Marcus

Marcus Osborne 3:12
You told me 30. You told me 30.

Alexandra Drane 3:15
I love age. I’m 50 baby. I think each of us have like a 12 year old brain. And we’ve discussed this. And then I have my 50 year old brain. And my 12 year old brain, I call my lizard brain, and it lives back here. And it’s very fast to be vindictive, and spiteful, and cranky, and jealous, snd you know, all the unattractive things. And then my 50 year old brain, the older I’m getting, the more it’s like, let’s calm down. What does this mean? What can we learn? Let’s love on people, let’s have empathy. And for me, part of what keeps me going every day is learning to do a better, better job telling my lizard brain to be quiet and getting stuff from my forebrain. And through that process, sharing that entire messy bit to help other people feel less alone as they’re going through it in the hopes that maybe tell me some of their hell also so I can feel less alone too.

Marcus Osborne 4:03
Yeah, and I think one of the things that, maybe I’ll do my own kind of spin on what I heard, is one of the things I think that motivates you is the strong desire for truth, and that I’m sort of mindful back when you did the work in The Unmentionables. The truth there is that, you know, if I’m a diabetic, I sort of know what I need to do to manage my diabetes and I may not really care about – diabetes isn’t my sort of thing. What’s really kind of stressing me out is the fact that work/life isn’t working. Maybe I don’t like my boss or my boss’s boss, right? My sex life sucks or I’m struggling with my kids or, you know, an aging parent that I’m having to take care of. And so, I think your sort of focus on the truth is a motivation. There are people who just, you know, they live to want to get throughs out, so I’ve always respected that in you. Now, I think back to your motivations, if I were to have to summarize you in just a quick phrase relative to the role you’re playing in healthcare and the health system is, you know, you are the hurricane of healthcare. And I think somebody who didn’t know better would would think that was a negative, but I think, you know, the force and energy and passion you bring is huge. And what I will tell you is it’s very uncommon to see people who can sustain that level of energy and passion. So my question is, often then, what I find is that people who have that energy, it’s not just sort of a deep motivation, but they have almost something sometimes that sort of drives them crazy, these and you’re not talking about these kind of theses, this view of either how things are or how they should be, and more about how they should be, this thesis or set of theses around, you know, what should be different? What should be transformed? I’m interested, what’s the thesis or the theses that just compel you? You talked a little bit about it, but what in healthcare specifically, that have compelled you to want to be an entrepreneur, that have compelled you to want to do startups, to compelled you to actually want to work in this industry, that is not necessarily the most fun industry in the world. What are those kind of theses that compel you?

Alexandra Drane 6:16
So, I have three ways I’m going to answer that. One is, I think a lot, you know, I’m a super geek. And so data and stories, the combination of those two things, the interplay of that, really compels me. I think, particularly in a moment right now where things are so divisive, I actually think we are way more alike as humans than we are different. And I think the next big industry is love. That would be point number two. And then I think point number three would be, I think we all have two personalities. We have the personality as healthcare industry people that we bring to work, where we’re excited about value-based this and cost-cutting that and, you know, we can scale this, and up into the right. And we use all these words that disconnect the process that we’re doing, the effort that we’re working toward, from who we actually are. And if we come back to the example that you gave, you know, I start work every day. Usually, my very first thought out of bed is I am a complete failure. I didn’t get any of these things done last night that I was supposed to, I’m already behind. Then I try and get my kids ready for school. And every morning, I start beautifully hugging them, snuggling them if I’m lucky enough to not be traveling, which I have been lately. Cuddling them in bed for a second. They’re 15 and almost 17, so they don’t always love that. And then as the morning wears on, as in like the 25 minutes we then have to get to school if I’m lucky enough to be driving them, it devolves into, I’m yelling at them, they’re yelling at me, I’m trying to answer email. And as the day sort of wears on, I get in a fight with Antonio, I’m cranky about an email that didn’t get sent out. And I’m trying to do an unpaid caregiver task. And so when I think about the biggest opportunity in healthcare, I’ll use this silly analogy, which is, let’s say that you and I were in marriage counseling. And you were the healthcare industry. And I’m a human out in the world. And there’s an exercise that marriage counselors do, where they say write down on a piece of paper, what are all the things that matter most to you? And what are all the things that matter most to your partner? And then you compare the two. And you can imagine, I started this by saying it’s a marriage counseling, right? Our marriage isn’t going well. Well, if you did that exercise, the healthcare industry and humanity, there’d be virtually no overlap because what I just described about my insane moment as a human who works in the healthcare industry and is insanely motivated to help people be happier and healthier in ways that impact top and bottom line, blah, blah, blah. What’s really going on every day is the fact that I’m a mess. And it’s caregiver stress, financial stress, workplace stress, relationship stress that’s driving that primarily. And at the core of all of that for me, is this unpaid caregiver reality that’s impacting so many people. And I think if the healthcare industry started talking about it – you talked about sex, you know, self medicating, worrying about the fact that you hate your job, or your think you’re a bad parent, whatever it might be. Those are actually the things that are the most foundational elements of health. Those are the things that are making our telomeres longer or making our telomeres shorter, which is a how long you’re going to live kind of metric. And so I think that for me, I want to meet people with radical transparency, enormous authenticity, with this foundational presumptive close that we as a population recognize that to love on one another, to care for others to be cared for ourselves, is the single most foundational element of humanity, and anything and everything we can be doing discipline that is actually going to result in health. And that’s weird. And for some people we’re like, but that doesn’t say anything at all about your heart rate, or did you exercise? Or what are you eating? Or how much does somethng cost? Or is it accessible or not? Yes, but until you solve that you haven’t even earned the right to do those other things. Does that make any sense?

Marcus Osborne 10:16
It does. And I think you’ve kind of highlighted, you know, something that I know you and I’ve talked about a lot, which is one of the kind of patent absurdities about the healthcare system is around the design paradigm and the kind of traditional design paradigm. I always say that sounds super academic, and maybe it is academic. But the traditional design paradigm is about this concept of balanced interests, this belief that you have to balance interest. And if you want to create really great solutions and healthcare, by God, you better address the needs of not only the patient, but you also gotta address the needs of the payer, of the provider, of often the product manufacturer. And I think what you’re actually highlighting is, like on paper, that sounds great, like you describe people, like I’ll say, people, that’s the design paradigm, like, yeah, that is a design really? Like no, no, that’s absurd. Health and healthcare is about people, it’s about individuals, it’s about taking care of people, and that the rest of those entities are there to serve. You should be part of the solution. You’re not what we should be designing for. And so I guess, to your point, that I’m sort of mindful of your new adventure. And I use that because I think about entrepreneurship as an adventure and some adventures, as somebody who’s gone on hikes and seen the good and bad, adventures are not always fun. They are adventurous. You go up and down, left and right. But as you mentioned, you’re focusing on caregivers. But you’re also focusing in on them in a way that you are trying to create solutions that are directly for people. But in reality, the system, as much as you hear people in the healthcare system talking about wanting to be consumer oriented, or consumer centered or whatever. Usually, they sort of fall back on that kind of balanced interest approach of like, well, yeah, I’m designing for the consumer. But I’m really also designing for the payer. Well, if you’re also designing for the payer, you’re not designing for the consumer. So I’m interested in, how do you stay true to that desire to be about love, and be about the individual, and be about the family, and the community, and create solutions in healthcare that stay consumer focused, but not get pulled in by the gravitational forces that get generated by the provider community or by the payer community, or by the product manufacturer community? How do you kind of deal with that challenge? I mean, it’s almost the dichotomous kind of reality. I want to build things for people, but I also have a system that has all these other interests, and all these other players that kind of influence that. So, how do you deal with that as an entrepreneur to the extent you’re trying to stay focused on people?

Alexandra Drane 12:49
Well, so to the extent, you know, this is the part with being a bootstrapper. You know, the best investor for us is revenue, like we have to be getting paid for what we’re doing. And it’s very humbling to have to live that over and over and over again. And it reminds you every day, you know, creating a top and bottom line impact in a sustainable, scalable way is about connecting with humans. And to do that, I always think about it like there’s a whiteboard in my office, and it has lots of boxes on it and little lines connecting it. That’s silly. That has nothing to do with, as you and I both know, what the actual outcome is going to end up being. I can draw gorges, I can torture a spreadsheet until it confesses, I can run numbers all day long. But is that actually going to translate into a human doing something differently, better or worse, being supported in that moment of stress? If you dug into that box on the whiteboard, what actually is at the last mile? What is at the latch hinge? What is a human doing for another human, with technology or without technology? And one of the examples I want to give, because I had this experience with you at Walmart Health, when we were watching humans come through the door and observing. You know, one of the things that you’ve talked about forever, Marcus that I believe in too, and it’s continues to enrage me, this just happened the other day, again. Where in healthcare did we forget that we are humans and our job in healthcare – let me use as the example, somebody who was doing intake. And I’ll use the example of my mother in law when she was in the middle of being diagnosed with what ultimately was a terminal diagnosis and we knew it was going to be. We went with her, we were late because of legitimate traffic. She’s not as mobile. Antonio, my man, runs her up. We call to head to say we’re gonna be 15 minutes late. The woman who picked up the phone was so mean, that already I was like, my heart rate is pumping and I’m not even her direct caregiver, Antonio, her son. But I’m already stressed. I’m like, we tear into the hospital. I’m like, okay Antonio, you guys run up so that they know we’re here. I told him we’re not giving up. He gets up there. He calls me while I’m parking the car and says, don’t even bother coming. They said because it’s 15 minutes late. I’m like, are you kidding me? I’m coming. So I, you know, march up there and the woman behind the desk is so mean, she’s so mean, that I said, well, we’re not leaving, actually, we’re not leaving, you can get the manager. We’re not leaving. We just drove an hour to do it. She just flew from Sicily to have this appointment. We’re so stressed out over the others, we’re not leaving, like, please get the manager. The manager comes out. By this point, I’m standing in the middle of the waiting room in a tight little circle. Start talking to the manager, I start crying. I start crying because I’m so angry because I’m like, I don’t understand this. You are in healthcare. Is anybody in this room? Did anyone wake up this morning, like, I can’t wait to go and maybe get a terminal diagnosis? I can’t wait to be the caregiver in this situation. Guess what, I’m not getting paid for this. Right? I’m doing this in love of this person that you’re getting paid to support and you’re mean to her. And you’re mean to me and you mean to her son. This is unacceptable. I thought I was going crazy. Like, where is the concept of customer service? And so, when you’re designing your beautiful, sexy technologies, when we’re designing our beautiful sexy technologies, when we’re, like, coming up with gorgeous whiteboard boxes leading to Wodsworth, if we can’t frickin start with just being civil to the person at the center of all of this, the patient, and then the human and all of those around them, right, when that bad day happened for my mom in law, I had a terrible day. Antonio had a terrible day, my kids had a terrible day, I did an awful job at work. When we talk about cost, think of the ripple effect. Was I protected that day? No. And I’m not mad at that woman at check in, you know why? Because I bet she was having a bad day. She just forgot that her job includes, you’re not allowed to be mean to the people you’re supposed to be serving. And I’d like to go so far to say, actually, you’re obligated to be kind, right? And if she had been kind, she would have had a better day. So to me, if we, whatever we’re building, however complicated, awesomely scalable, unicorn, whatever it might be, start with, are you kind? Is everything you’re doing making people feel less alone? Is it holding them, and loving on them, and supporting them? Is it what you would want? And I think so often we forget about that. It’s like we have this weird little barrier between what we actually crave and yearn for and weep when we don’t have and what we think we’re putting out there for other people.

Marcus Osborne 17:18
Yeah and that would be, I want to kind of put a pin in that. I mean, I think if I were to think about advice that I give to any entrepreneur in health, if you’re going in and you don’t love people and you don’t love the people you’re trying to serve, and you’re not committed to do everything you can do to create solutions that fundamentally make their life better, you should probably go be an entrepreneur somewhere else. I will acknowledge there are a lot of companies and startups that have been created that, I don’t think that was their original intent. But I think, relative to what we need now, that’s what we need more of. So that’s my, I’m getting on my high horse.

Alexandra Drane 17:55
If you are not coming around to a place where you’re loving what you’re doing or loving on the people around you, there’s not a lot of long term success for evil and hatred. There are some short term examples, but not many long term. So whatever industry you’re in, and this is a call out to employers and any consumer focused, like, make sure that the people who are working there are happy in whatever they’re doing and that you’re loving on them in that role. Sam Walton, what did he say? Take care of the associates, the rest takes care of itself. That was actually a very foundational healthcare, call out health-related call-out but that’s not why he was doing it. He was doing it while he was building the best retail, like a huge retail operation. So, amen to what you said. And I think it should actually be even beyond people in health care.

Marcus Osborne 18:36
Yeah, no, I agree. Okay, so I’m gonna do a little pivot, I’m going to ask you a question that part of me, actually a good part of me, absolutely hates asking you this question because, as I thought about it, you should never ask somebody a question that you shouldn’t be comfortable with somebody asking you. And I can be confident no one, no one, no one is ever going to ask me this question. So that’s the problem. It’s not that I wouldn’t be comfortable in answering, it’s that I’m never going to be asked ever and it’ll be obvious here why. Let’s, you know, be very blunt. My sort of sense of, given my engagement with many of, you know, many, many industries, the industry that is the most dominated by old white men, like myself, I will have to acknowledge and be self actualized. I’m old now. You know, I have two sons who are in high school, I am white, and I’m a man. I’m in an industry that there’s just lots of us, way, way more, I think than we need. And I understand the challenges of that. I’m interested in the process of being an entrepreneur in an industry that kind of looks that way and is dominated by kind of a single group in the way that it feels like the healthcare industry tends to be. How have you dealt with those challenges? What are those challenges and what’s the advice that you wish somebody had given you when you dove headfirst into this industry?

Alexandra Drane 19:57
Again, I’ll come back to this particular moment in time. There are so many examples of how I don’t think you or I have earned the right to speak on behalf of the populations who need the most support. So I start by saying that and I know you’re living that right now in all the work that you’re doing. I’m living that in the work that we’re doing. We know the extent to which unpaid caregivers, which is my particular focus, have been disproportionately, those populations most at risk, have been the most disproportionately impacted by COVID in every metric, on every measure, in every way possible. I think that the single greatest scar I would offer, you know, learning I would offer, is not related to being anything, any of the categories we can put ourselves in. It’s just related to being an entrepreneur and being a human, and being somebody who is always curious. And that is, the second you feel comfortable, be afraid. Challenge yourself, get out of your own bubble. Every time I’ve made the biggest mistakes, it was because I thought I had the answer. Not only did I not have the answer, because maybe for one second, I did have the answer, ut that second passed. And if you think you know what you’re doing, then somebody else is already doing better than you. And that right now, in a time where – there’s a wonderful quote. No humans – the quote is no man – no man steps in the same river twice. He’s not the same man. It’s not the same river. If that was true before COVID, oh my gosh, is it true now. So there’s a risk always in making presumptions. I think that the only truth we have right now is we have no idea what’s happening, we have no idea what’s gonna happen next, we are in totally uncharted territory. And for entrepreneurs, if you are feeling really, really confident that you got the answer, and you got the solution, I think you should be afraid. And I’m not saying in a bad way, I’m saying in a beautiful way, like, immediately say to yourself, hold on, let me go back and revisit things. Let me get myself out of my bubble and expose myself back to the elements. We do this thing, Marcus, you know, called wing walking. We strap on wings and we go out into communities, and we talk to anybody on the streets, and we specifically put ourselves in communities that we are not very familiar with. And it is so scary to do it. I can’t even tell you. And I always don’t want to do it until, once I’m out there. you know we did this at Walmart, we have the most beautiful conversations with people. And humans are so freakin smart. Like the people who are out there walking around doing their best to survive day to day, they got all the answers that we need. And so, get out of your bubble, challenge your assumptions, go put yourself in very, very uncomfortable situations in ways that set out to prove or disprove what you think is true. And you’ll be amazed what you learn and how wonderful it feels to have challenged yourself most foundationally in something that you were like, oh, yeah, we got this, like, maybe we don’t.

Marcus Osborne 23:04
I actually love that. There was a key theme and I want to kind of push on just a little bit more with just what time we have left. There’s this mythology of the innovator and the entrepreneur of, you know, usually it’s two people, they’re in a Starbucks, you know, that sort of idea of, they pull out a napkin, and they write down a business plan on the back of that napkin. And then they are dogged about that. And like, they won’t take no for an answer. They won’t let anybody get in their way. They will come out and fight every day. What you sort of highlighted is, I don’t think that’s real. I think what’s real is being an entrepreneur and being an innovator is about being open to learning, and learning fast, and figuring, and screwing stuff up and making changes and being pragmatic and being okay to say, I’ve evolved, I’ve evolved, I’ve evolved, I’ve changed, I’ve changed, I’ve changed, and that if you did do a napkin in a Starbucks, that you can sometimes put it up on a wall and say, well, that’s really fun, because I’m not doing anything that’s like what I thought I was going to do that day in Starbucks, right? Maybe where I’d love to kind of close is just to get your perspective a little bit more on that because I think that’s the greatest insight that you can give anybody who wants to, who has an inclination to say, I think I want to go start something up myself, which is, that seems a little scary. It seems like, hey, you’re going to go into something and you are going to create a concept, you’re going to create a plan or an idea, and it’s going to be wrong. So, just go ahead and assume it’s going to be wrong and that it needs to evolve. And if you have an entrepreneurial bone in your body, that actually feels scary to me. And so I’m interested in, if you were to give advice to someone given what you just laid out, how do you make that not scary for someone who is inclined to take that leap?

Alexandra Drane 24:46
I’ll go back to that quote I had of, like, if you feel safe, be afraid. You know, like, secretly I want to be racecar driver and I’ve been to racecar driving school, and that’s actually a racecar driving quote, like, if you feel safe, feel afraid. I’m gonna say something that maybe people like to hear, maybe they don’t like. Not everybody should be an entrepreneur. They really shouldn’t, right? Like, there’s lots of different roles for people to play. I love the Art of War book by Sun Tzu years ago, like different personalities, different skill sets avail themselves of different roles in society. And it’s so hot and cool to be an entrepreneur right now, like what you just said is the reality of being an entrepreneur. And if you don’t get jazzed, if you’re not turned on by, if it doesn’t make you all fired up to know that today, you might fail 18 new ways, then you might not want to be an entrepreneur. And I was thinking when you were talking, we had something, I wrote down “Wall of Pain”. At Eliza, by the end of the 15 years I was at Eliza, we had this wall of pain. And it was just documenting all the things we kept learning and learning and learning. And we kept learning them because we did something wrong. Our assumption was wrong. And we’re like, oh, we thought this. Nope, that was wrong. Nope, that was wrong. And so, every time we went through one of these processes, we evolved and got better. But then, by being better, we made another mistake. And so we just learned to celebrate, capture and celebrate, those things. And I think one of the other things I used to believe in the early days at Eliza was that there was going to be a moment where things were going to get easier. Once we reach this, you know, when we have our first big national customer, you know, once we have our first profitable year, once we have signed X, Y or Z, once we get, you know, noticed by somebody. And what you realize, and I’m still realizing this at the ripe old age of 50, it never gets easier. And if it does get easier, you should be afraid because you’re about to get hit from behind by something. Like, that is what you’re signing up for is this, you know, constant whiplash between, oh my god, we just sold this, we are going to be world famous, we’ve changed what happens for an entrepreneur in the span of 25 seconds. Like, we are the smartest people I’ve ever met, I can’t wait to call my mom, right, I’m gonna be on the cover of Life Magazine. I’m aging myself with the phone and the Life Magazine, but you get the point. And the next thing, you’re like, everything is over. I’m fired. We’re terrible losers. And we’ll probably be on the front page of the Wall Street Journal for the biggest disaster example ever in healthcare. That wild swing is a foundational part of being an entrepreneur. And I think it’s part of what keeps people raw, it’s part of what keeps them focused on the edge, earnest, and there’s nothing that bands people together more than facing common adversity, a common enemy, which is all the things that battle you as you’re trying to change the world. And so if you turn all that on the positive side, you find people who are completely aligned with you, want to make this extraordinary impact, are humble in the fact that there’s going to be a lot of ups and downs in the process. And you become the very, very best of friends in working towards that, who also kind of can’t stand each other. But you keep working through it in the process. And I think for me, I would just say, number one, really question whether or not you want to be an entrepreneur. You might not want to be. And if you do, then when you have that moment where you’re like, I’m the most horrific example of failure ever, I literally can’t get anything right, just calm down. Have a red phone. Marcus, you’re one of my red phones. Marcus, I suck at everything. And what do you say? Probably not everything. I think we could find something, you’re like, keep going, right? And that’s the key.

Marcus Osborne 28:15
I think that’s the most brilliant advice ever. And so I want to thank you for agreeing to do this. I know you’re probably gonna have to change your shirt now because you’ve sweated so much from having to have me ask you questions, but I just want to, you know, not only are you the hurricane of healthcare and you are a force of nature, but I think anybody who is feeling, if you’re doing work, trying to do the right thing in health and healthcare and you’re ever not feeling it, all you need to do is get within a few yards of Miss Alex and the energy and the love will transfer. So I appreciate all the energy and love that you bring. And what I would say is, if I could copy you a million times over, or 100 million times over, I would do it because I feel like, if we could do that we would have already kind of addressed all the problems that we have and things would be wonderful. So I hope you keep going. And again, thank you for agreeing to do this, as painful as it was for you.

Alexandra Drane 29:16
I would follow you to the ends of the earth. I love you and everything you just said to me is actually really for you. You are all the things I just described. You know, I think people who suffer/exalts in that, it’s so lucky when we find each other. So let’s just keep finding other people and lifting them up and helping them go through the same stages, right, like, next big industry is love.