Episode Transcript
[00:00:00] Speaker A: Hello, and welcome back to imperfectly honest. I'm Kayla, and today's conversation starts with a big question. What does it really mean to succeed as a woman in a world that wasn't designed for us? You see, for so long, Elizabeth and I held the same belief that the path forward was to play by the same rules as the boys, to compete the same way, to show up the same way, to even suppress our femininity and parts of ourselves to fit that masculine mold in the workplace. But lately we've been wondering, what if that's the wrong game entirely. And I am so glad that she brought this conversation to the table with Jane Miller, longtime CEO, investor, and author of the book Sleep youp Way to the Top and Other Myths About Business Success.
Together, they get into the messy, nuanced reality of gender dynamics at work and the similarities of those dynamics that are present when dating. Everything from competition between women to confidence to the question that no woman really wants to ask out loud. Are we using all of our advantages or intentionally holding some back?
This is a conversation about what it looks like to truly show up as your whole self and use your full package, as Jane urges, rather than show up as who you think you're supposed to be. So buckle up for an expansive conversation. Let's get to the episode.
[00:01:32] Speaker B: This isn't imperfectly honest. I'm Elizabeth, and after about four decades, I'm shifting from the person I always thought I should be to the person I really want to be, in part because I've learned to be honest both with myself and just about everybody I encounter. It's not always perfect. Sometimes it's a rocky road. But I'm learning a lot by being imperfectly honest and thought you might learn something, too.
Hey, all.
Today we have a special guest, and just to tee up this conversation, I've been doing a lot of thinking, because thanks to generations of strong women before me, I grew up thinking I could do nearly anything my brother could do.
However, despite all the work of generations before me, I've had quite a few glass ceiling moments that have convinced me that the playing field is not actually equal.
And I've also realized that in my attempt to make it in a man's world, I've failed to tap into the power of my femininity, to use that femininity to my advantage.
And with imperfectly honest, I'm challenging all of my previous assumptions and challenging cultural norms to figure out who I actually want to be. In my next chapter, I'm asking myself three questions on this topic.
Is gender Inequality, a problem, an opportunity, or both?
What can I as a woman do that men cannot, should I, can I and will I use my looks and sexuality to get ahead? As some of you know, I've spent the last decade building a venture capital fund that invests in women led startups to prove the thesis that investing in women is a financial arbitrage opportunity. And I've invited one of my investors, Jane Miller, who happened to write a book called Sleep your Way to the Top and Other Myths about Business Success, to have a candid conversation on this topic. Jane, thanks for being here.
[00:03:54] Speaker C: Elizabeth, thanks for having me. I am so intrigued with your three questions that you're asking yourself and I'm anxious to dive into this whole topic.
[00:04:03] Speaker B: So to start, can you tell us a little bit about you and also the premise of the book?
[00:04:11] Speaker C: I would love to let me tell you a little bit about my career which sort of frames up why I wrote the book. I started my career at Frito lay in Dallas, Texas and had the first 25 years of my career has been with big consumer products companies. At Frito Lay I rose to be the first division president that was a woman.
I went from there to run a division of Best Foods Baking. You would probably know the brands or a Wheat Thomas English Muffins or Intamins baked goods. I went from there to Heinz where I started as chief Growth Officer and then moved to London as the president of Heinz in the UK and Ireland.
From there I was part of a team that got Hostess out of bankruptcy and that was my first 25 years. And then the last 18 years I've been in the natural products industry. I started my first role was CEO of Rudy's Bakery based in Boulder, Colorado. I sold that company, went on to do a couple of early stage startups.
Was the CEO of a company called Lily Sweets that I sold to Hershey's about five years ago and then about three and a half years ago I came back to Rudy's as the CEO and an investor. So you know, 40 some years in business, big companies, small companies, lot of success, a lot of not so much success. On the personal front. I was married for a number of years. My husband passed away in 2003 and I currently am single and I have a couple horses and a little dog named Earl.
The book Sleep your Way to the Top and Other Myths about Business Success was published in 2014. It was right when I left Rudy's for the first time and the concept was this. I found myself giving a lot of advice to young Women who were starting their careers and I felt that I couldn't scale it in a one to one mentoring situation.
So I started a career advice website that was called Jane Knows right before I came out with the book. And the premise of the book was to bring the stories from my career to life in a humorous way, an easily digestible way, and also focus on a lot of the mistakes.
Most business books, in my estimation was all about all the things that we do amazing and great and how we moved up the corporate ladder and my career was up and down and sideways. And I just felt that if I could bring that to life in some way for the next generation of leaders, that it would have people have the confidence that you can make mistakes and you can still be as successful as whatever success means to you.
[00:07:05] Speaker B: It's been a bit since you released that book. Has your thinking changed since then?
[00:07:12] Speaker C: Not at all, actually. And I think the thing that I'm disappointed about is that the world has not changed in terms of how a lot of situations that young women are in. And I would say young men too, I think just divert people that are maybe more diverse when they're in the work environment. And I think that's what I found that, you know, the stories that I was, was giving, you know, 12 years ago or 30 years of my career. And what I found immediately after I wrote the book was the how many things that happened to me in the 1980s were still happening, you know, in this century. And so I think. So my opinion of the book hasn't changed, or my opinion of sharing my stories hasn't changed. I think what I'm disappointed in is that the world has not moved forward and be more women friendly.
[00:08:08] Speaker B: So I've thought a lot about that conundrum.
And one of the questions that I've asked myself is, is there a possibility that inequality is just meant to exist? That maybe, maybe because of millions of years of evolution that there's something that we're not going to be able to change and maybe we just sort of need to move with that rather than against it. Do you have any thoughts on that?
[00:08:38] Speaker C: Yeah, I do, and thank you for asking. I would say that I do believe that we can change. I believe that part of the situation that we're dealing with, that I dealt with, that perhaps you've dealt with in your career following me by a number of years, is that more women have to help other women.
That the thing that needs to change is women like myself who felt like I had to have all the answers. I Had no one to go to, and I had to, like, make every mistake along the way and not have a support system around me. And what I saw when I was coming up through my career was that I thought the men did a better job of supporting one another, maybe because there was more of them, maybe they were more comfortable based on just interactions that they were having and the norms and the work workplace. But I really think the thing that changes the inequality in the workplace is whether it's women helping other women or men helping women, but this idea that nobody should be trying to be on this journey by themselves. And to me, that's the hope that I have, that there's going to be much more of a communal support going forward. Because to me, that's. That's the key thing. It's about having community when you're in the workplace and not being by yourself.
[00:09:58] Speaker B: It's interesting that you say that, because I've been thinking a lot about my natural tendency to feel competitive with other women.
So I'm dating for the first time since I was 21 at the age of 44.
And it is really rare that I date someone who doesn't have some other woman in the picture, whether it's an ex wife or someone else that they're currently casually dating or something like that. And my natural tendency is to compete rather than to support or embrace other women.
I've been thinking, is this something that's innate or that I've learned? And do you think that there's some sort of innate or learned drive for women to be competitive with each other rather than to be supportive?
[00:10:51] Speaker C: Gosh, what an interesting observation that you have there. I think that in my experience, and that's really all I can share, I think that the dynamic was created and I'm going to use the business environment and not the dating environment, but in the business environment to create that kind of tension that if there were 10 jobs in senior leadership and one was a job that had a woman in it, that that was the job that you were going for, was the woman's job. And. And I think it was actually created within the environment. So I. I actually think it in many different workplaces. And I do think I just feel very blessed. I did not have any women mentors throughout my career, but I had a number of.
Not even a number, a couple of men who were very, very supportive, including my husband.
And I think having somebody that helps you build your personal confidence allows you to be more confident in helping other people.
It's actually one of my Favorite topics. Because I think if it comes from insecurity, that that competitiveness happens, as opposed to some innate quality that we're born with.
[00:12:06] Speaker B: So one of the things that I always wanted to change about society is that historically, beautiful women, conventionally beautiful women, have had an edge in society. And unfortunately, some women have gotten ahead.
Hence your book title, sleep your Way to the Top, which you've debunked as a myth. But there are people who have done that, and there are women who have had to use their conventional beauty historically to get ahead.
And I never wanted to be one of those women. And I felt like, because women had fought so hard before me to earn me that right, that I never wanted to use my conventional beauty to my advantage. And I remember one. One of my proudest moments was that I actually raised a lot of the venture capital fund that I ran from the chairlifts of Vail, networking with investors. And I would say, objectively, I have some conventional beauty. I dare say that about myself.
And I always wondered if the men that were investing in me would have said yes if I didn't have those looks. And I remember I had this moment where I was skiing with prospective investors, and I was doing this on a pretty regular basis, and I have a really hard time staying warm.
I would wear this big baggy down coat to stay warm in these baggy snow pants. And I have been blessed recently with a few male friends who are not afraid to tell me their unfiltered truth.
And I'm telling this story to my friends about how I got to the point that even when I was skiing and you couldn't see my face and I was in this baggy down coat, I could get the same results of when I was in a cute, sexy dress talking to those same investors. And my friend says, yeah, I've seen you in those quote, unquote baggy ski pants. Every man knows what you look like under those ski pants.
I thought, oh, my gosh, this story I've held is potentially totally untrue. But anyway, another question I've been asking myself is, have I actually been disadvantaging myself by trying to go against the grain rather than not doing anything unethical, but just sort of using my potential conventional beauty as a competitive advantage. Any thoughts on that or experience based on that?
[00:14:58] Speaker C: Yeah, I love. I love sort of how you talked yourself into thinking that the baggy clothes. Because I have a. I have maybe a similar situation to share. But what, you know, what I would say to start with, Elizabeth, is To me, as a person, you're a whole package. And if you're blessed to have, you know, conventional beauty, as you talked about. It's like, I. I think you use your whole package to your advantage. That you don't.
You know, you're. I know from our experience working together. Or being an investor in your fund 10 or 12 years ago, you're wicked smart. Like, so to me, like, would you want to hide how smart you are too? I mean, like, this is like. It's a whole package. Like, you show up with, you know, with what. What your looks are, how you interact, your energy, you know, your strength of character, your confidence. I mean, all that stuff, to me, is a package. And that all of it is. All leads to the amazing, remarkable person who is you or who's me. And I. And I think.
I think it's super important for your listeners. To really think about that. Which is, you know, show up with your whole self. And use this. The tools that you've got in your toolbox. To help you be successful again. Whatever success would mean. So I'll. I'll tell a quick story that is a little bit similar to yours. So I had started my career at Frito Lay, as I said. And my husband had an opportunity to move to New York and start a business. So I transferred to Pepsi.
And at Frito Lay, I had been enormously successful. And just moving up the ranks. And just, you know, like, everything kind of went my way. When I went to Pepsi, I literally felt like I was a fish out of water. That somehow all the talents that I had at Frito had disappeared when I went to Pepsi. And one day, a senior vice president called me into his office. And he said, you know, Jane, what we'd like to do is, you know, we. We'd like to send you three days, one to one, with a psychologist. To help you work on your style.
And I'm like, what? You know, what?
This style, which is so fabulous, you know? And they're like, you know, we think you have a lot of potential. But you need to work on your style. And so they sent me three days to a psychologist.
To talk about my style. And you know, what I learned, which I think is maybe helpful to some of your listeners. It definitely was to me. Was that the way I was showing up. It didn't have anything to do with my looks. I'll get to that in a second. But the way I was showing up in the workplace, my. My style is super informal, highly energetic. And I'm still that way today. At 60, almost 67, but at 30 years old, probably on steroids to some degree in terms of energy and enthusiasm and passion for being in the world. But it came across at Pepsi as being unprofessional.
And so the problem that I was having and why they sent me to the psychologist was that I wasn't showing up at Pepsi as being this serious professional because, you know, we all know that soft drinks are super serious. So I go, so I, you know, so I go to this, the psychologist for a couple days and I come back to my husband, I'm like, okay, Michael, I know what I need to do here is I'm not coming across professional enough. So at the time I had, you know, really long imagine 80s bouffant hair, you know, big hair, big shoulder pads, short skirts, three inch heels. And that was, you know, the, the business look I had. So I came back from this thing, I said, okay, I need to be more professional. So what I'm going to do is I'm going to put my hair up in a bunch of.
I'm going to. So I'm not going to have this long flowing hair. I'm going to wear glasses, which I didn't need at the time, and I'm going to show up to work with pants on, not a skirt. And just, you know, to, to make a strong statement that I can be professional.
So I show up the first day and I have the hair in the bun and the glasses and the pants on, not the skirt and the high heels. And I walk into the office and literally everybody starts laughing at me, like laughing out loud. And one of the people that worked for me said, seriously, like, you think this is gonna be the thing? It's kind of like your snowsuit thing. Like this is the thing that people are gonna all of a sudden say, oh, she's super serious because her hair is in a bun.
You know, And I just love that story so much because what came out of it for me was not how I dressed, but was how people were reacting to my energy showing up in this environment.
And what I needed to learn in that was I could either be myself, which was this all out, passionate, high energy person, or I could adapt to what they were looking for at Pepsi. And I always equated it to like, I spoke French and they spoke German, and the more I spoke French and the louder I spoke French, the less they paid attention to me. And so I always think about that in the workplace, which is hopefully for many of us that have the great luxury of having Wonderful education and good career experience. You have choices and, you know, if you have a choice, choose not to be in an environment that doesn't tap into your natural skills.
[00:20:20] Speaker B: What you said about the bun really struck me because I used to be in much more of a hurry than I am now, and I went for maybe three years without actually drying my hair. I would go to the gym in the morning and I'd throw my hair back. And what my mother deemed to be the perma bun, she called it.
And it was just not that feminine and sort of strict looking.
And although making a small change doesn't change who you are as your core personality, it does change things.
And so I guess I'm just kind of wondering on that, that note, how do you think about the level of quote, unquote, change you want to make to your hair and your body and all those things, to adhere to conventional beauty standards and to feel good about yourself?
[00:21:25] Speaker C: Well, that's. That's again, such a great question. I mean, to me, this again comes back to personal confidence.
I honestly believe that that is one of the most important criteria for anyone's success. And I think going back to the whole, you know, men versus women dynamic, I think that men, what I do think men are, they're innately more confident than women. And I don't know why that is, but I do think that that would be a fair statement to make. And to me, confidence is the thing that allows you to show up with your best self.
And if showing up with your best self means that you are going to do your hair in a certain way or you're going to dress in a certain way, and whether that means you're going to make alterations on the look that you have or whatever, I really think it comes down to it has to start with you and not doing it for somebody else, or not trying to do it to fit in, but to do it to make you feel better in the world. Because I do think that when you are confident in yourself, you show up in a way that allows you to bring more of yourself to the world. And I think at the end of the day, that's part of what our roles on this earth are, is to show up in a way that's meaningful.
And I think you do that if you have more confidence.
[00:22:52] Speaker B: Yeah, I think that's right. And I have gotten to the point recently that people will no longer say, wow, you look great. They will say, wow, you look great. I never would guess that you're 44. It's like there's a caveat. I can't just look great. I have to look great, quote unquote, for my age.
[00:23:14] Speaker C: Well, wait till, wait till you get to be my age, Elizabeth, where nobody ever even says you look great because of your age.
And honestly, it's a, you know, it really is. It's. This is, is such a hard thing as you get older. And again, nobody ever said this to me because I didn't really know anybody that was more senior to me in the business world or, you know, other than my mom, you know, that much in life. And it's, the, the aging process is, is so hard because I think about myself. As I said a couple of times, I'm going to be 67.
In my mind, I'm 35.
And then I like, I am 35 every day and I look in the mirror and I'm like, oh my God, there's a 67 year old woman looking back at me, you know, so, so it is, it's really, it's, it's a, it's a difficult, it's a difficult transition to go for, whether you're in business or not, just in life.
[00:24:13] Speaker B: How do you feel about plastic surgery and augmentation for your age?
[00:24:19] Speaker C: I think it's every woman's prerogative. I mean, I love one of my, like, role models is Jane Fonda. And she's amazing and she is very forthright about, you know, what she's done. And she's absolutely beautiful. And I think she's probably 82 or 83 now, something like that. You know, for myself, I don't know that I would really do it. It's probably more of a fear factor that, you know, you always sort of see these pictures of somebody where it went really terribly wrong.
I'm like, all right, would I rather look my age, you know, and be kind of wrinkly and be, you know, in my 60s, or do I want to look like a botched horror movie that still looks like I'm in my 60s, but I've lost whatever little beauty I still have left between the wrinkles?
[00:25:11] Speaker B: Well, I asked that same honest friend that I mentioned before who made the comment about the ski pants. I asked him, I said, so if I was going to do something to make myself look better, what should I do? And without even blinking, he said, Botox. Right away I thought, wow, we've thought about this once or twice, I guess.
Yeah, I am going to report that I am going to get Botox. And I'm thinking about how I want to approach plastic surgery as I age. But I used to have such strong judgments about people who did that stuff. And then when I got to that point, it's just a good lesson that you just can't make judgments until you walk in somebody's shoes.
[00:26:03] Speaker C: Isn't that funny? I know. No, that's exactly right. That's exactly right. And I say kudos to you for asking the question because I don't think I would ever, ever or have the courage to ask somebody that question because I really don't want to know what the answer is because I. Because I don't want to do anything about it. So.
So that takes a lot of credit. That takes a lot of courage to say, what, you know, what should I. You know, what should I do? And then. And then be open, you know, be open to doing it. So. And again, I think as you talk about that, what I love is, I think it's. It'll make you feel better about yourself. And I think, again, that's. That's really, really, at the end of the day, the most important thing. And I know I've said that a couple times during our conversation, but it's really, how do we have that confidence and feel comfortable in our shoes, however that plays out for each one of us? And I think respecting people that make those decisions and not being judgmental about it, you know, it's because everybody's journey, like you said, until you've walked in somebody's shoes or you've been in that situation where you're like, oh, never would have thought about this when I was 20, you know, it's. It's hard to. It's hard to judge or. It's easy to judge. It's easy to judge.
[00:27:11] Speaker B: Well, it's hard to judge what you'll do in the actual situation, but it is very easy to judge people, unfortunately.
So we talked a little bit about making it in a man's world. And one of the things that I've realized as I've gotten older is that I've tried so hard to be like a man because I thought that's what I needed to do to get ahead because all of my role models were men, that I failed to really leverage the good things about my femininity. And I'm wondering if you've had a similar experience and how that has played out for you.
[00:27:52] Speaker C: You know, I. I never tried to be masculine in any way or to hide my feminine nature, but what I did do was I picked up a very bad habit early in my career from the men that I saw in the workplace. And that bad habit was that they worked all the time, and they always had a spouse at home that took care of their kids and herself. And they could travel and they could work, and they could do whatever they did, and work always came first.
And so the bad habit that I picked up was not to act like a man in terms of my physical presence, but in terms of my disregard for my home life life.
And I always put work first.
And it had a very, I would say, devastating impact on.
On my. My marital life. And, you know, my husband, as I said, he died in 2003. But that was after we had gotten a divorce, and we got back together when he was diagnosed with terminal cancer.
And I had just prioritized my career so much that he had found somebody else that he wanted to spend time with.
And it was a really hard lesson to learn.
And now, so many times when I mentor people, I just always say, there's always going to be another job. There's always another promotion. But if you have an important relationship with somebody, whether it's a spouse, you know, partner, children, that is really hard to replace. And so that. That was the bad thing that I did early in my career was pick up the habit of disregarding personal and always putting work first.
[00:29:47] Speaker B: Wow. Thank you for sharing that. That is a whole nother podcast in itself.
[00:29:52] Speaker C: Yes. Yes. Yes, it is.
[00:29:55] Speaker B: Wow.
Wow.
So what advice do you have that you haven't shared already for women and also for men who want to be inclusive of women?
[00:30:11] Speaker C: I think it goes back to something that you said about being competitive and whether it's, you know, with other women or other, you know, peers that you. That you're dealing with. But I. I think what I would say is, how do you figure out what's important to you and run your own race? There's a great book by Cheryl Strait, who did Wild. It's called Tiny Beautiful Things, and it's a book of short stories. And in that, she has one short story called Run youn Own Race. And it's this whole concept of trying to figure out what's important to you and comparing yourself to you yesterday, as opposed to me comparing myself to you, Elizabeth, I'm comparing to, am I better today than I was yesterday? You know, have I done something more spectacular or run the race faster?
And I think, you know, the. The advice I would give is, is one really just try to understand what your priorities are and compare yourself to yourself.
And then the second thing is really, whether you're a man or A woman really reaching out and helping somebody that could use some help.
And again, when I was in my 20s, I thought I was supposed to know all the answers and I didn't know any of the answers. And I don't know why I thought I had to know all the answers. And I wish that someone would have said to me, ask for help and it doesn't show weakness, it actually will eventually show strength that you can be vulnerable enough to say you don't have all the answers.
[00:31:44] Speaker B: Wow, that's great advice.
And to build on that theme of competition, I heard a quote from Dolly Parton, who by the way, I had serious judgments about her and now I am fascinated with how she used her femininity to become a force in business and in art.
And she has this quote that goes something like, figure out who you are and then do it on purpose.
And I love that because back to this theme of competing with other women. I had this experience the other day where this man that I was dating, he was interested in this other woman who was totally different from me. She was somebody who would like to go on a 14 day rafting trip. And being in the woods for one night is like really a stretch for me.
[00:32:47] Speaker C: I'm with you on that. I'm with you on that. Yeah.
[00:32:50] Speaker B: And she just was totally into adventure and carefree lifestyle and all these things and just really different from me. And I found myself feeling so competitive. And then I figured out that if he really is not going to love me for me and he wants that, then it's not meant to be.
And there's something that I could probably learn from that woman who's totally different from me. And if I just allow myself to look at things through a lens of abundance rather than scarcity, there's always something complimentary or something that I can learn from people who I am intimidated by or who I feel intimidated by.
And I love that theme of supporting other women.
[00:33:44] Speaker C: Well, I would just want to build on your last thought because I think it's such a powerful one, which is looking at things from abundance versus scarcity. And I think a good friend of mine gave me some advice a few months ago.
When you have something happen to you, try to understand what the lesson is that's coming from that. So like you're trying to understand like, you know, like what do you learn from this situation about yourself? And I think that that's, that that sort of really strong self awareness is. I think that's what Dolly Parton was saying, which by the way, love Dolly Parton, I think she's amazing. And she is. She's such a huge proponent also of literacy, which is, I think, a really important, important topic that she's a big supporter of. So I would just say really trying to have that self awareness of who you are and try to say when things happen, not, oh, why did it happen to me, but what can I learn from that? So again, as I'm running my own race, I can be better every day.
[00:34:45] Speaker B: I love that. That is a great place to close. But before we close, tell us a little bit about your podcast.
[00:34:54] Speaker C: Oh, thanks for asking. So my podcast is called Jane's Place, and it's shot at my home in Boulder, Colorado. I really wanted to have the vibe of only being in person with people. And so you can watch it or you can, you can listen to it. And it's, it's really exploring different topics that are important to me. So season one was all about. It was called the Confidence series, which I talked a lot about with you today. And it was really exploring people's passions because I believe when you talk about and you're spending time on something that you care about a lot, it brings out this great confidence in you. And season two that we're right in the middle of right now is called the Strength series. And it's really talking to a number of individuals about resiliency and how they deal with times when things don't go our way because it's only a matter of time before things don't go your way. So it's super exciting. Just Janeplace.com and you can watch or listen. And as I said, we're just in the middle of season two.
Love it.
[00:35:59] Speaker B: Well, we will link to that in the show notes. And Jane, thank you for being here.
[00:36:05] Speaker C: Thanks, Elizabeth. This was so great to have this dialogue with you. I really appreciate the opportunity.
[00:36:11] Speaker B: So fun.
All right, listeners, until next time, bye.
