Kelsey Ramsden moves the earth, literally, as a serial entrepreneur in civil construction and real estate where her multinational company builds highways, airports, bridges and communities. Twice voted Canada’s top female entrepreneur, Kelsey is also an investor, cancer survivor, mom of three and the author of the bestselling book, Success Hangover. We talk about the ups and downs of entrepreneurship, how to inspire as a team leader and much more.
Melinda Wittstock: Kelsey, welcome to Wings.
Kelsey Ramsden: Thank you for having me.
Melinda Wittstock: I’m so excited to talk to you. You’ve done so many things in your entrepreneurial career. When we think of Wings, you have been a high flyer There are a lot of things that so many women can learn from you. And one of the places where I really want to start is I think so many of us confuse “having it all” with “doing it all.” And we stop short of our dreams because we think we’re going to work ourselves into the ground to be able to have all the things we want. I’m curious in all that you’ve achieved in your life, that conundrum, how have you navigated that?
Kelsey Ramsden: Okay, so I’m going to start with something that most people are going to hate. So let’s start there.
Melinda Wittstock: Sounds good.
Kelsey Ramsden: People are being sold a bill of goods on the steady right now. And it breaks my heart and here’s why. There are so many of us out there. There are legions of us feeling terrible about ourselves. Terrible. Waking up every day, not enough, not doing well enough, why am I stuck, right? This idea that there’s an epiphany moment when the sky opens and the sound, ah, and we have it all figured out, and everything is easy. And this idea of having it all, we think happens like that. But it does not.
Having it all, number one, is impossible. And if it is, you’re probably not set up to be an entrepreneur because it happens incrementally. Right? So let me ask you this. If you said, “I want to have a million dollars,” which is a very common thing. I said that myself. I want to make a million dollars. Do you think that the single day that your bank account rolled over from 998,305 to 1 million and 300, you had this orgasmic ah-ha [crosstalk 00:23:20 moment?
Melinda Wittstock: Well, I know personally that you don’t.
Kelsey Ramsden: You don’t. And it’s the same as [crosstalk 00:23:27 But let’s be candid about it. And it’s not “oh you poor millionaire” kind of don’t diminish the fact that that’s still a heap ton of money. But what I’m driving at is this idea that we’re all living in this kind of sense of having it all means everything is solved, everything is easy, the marriage is perfect, the children are getting straight A’s, the money is flowing in. But the reality of that is when you get to that place, if you’re like us, you’ll find another place to aspire to. Right? People like us are most comfortable in the discomfort [inaudible 00:24:09 we always need something to try and achieve. And so we actually structure our life in a way that the finish line keeps moving. No, but it’s true.
Melinda Wittstock: It is so true. I have just-
Kelsey Ramsden: It’s a sick and twisted fate, isn’t it?
Melinda Wittstock: It really is. I’m just laughing and chuckling to myself because I can’t stop having ideas, or refinements, or improvements, or new things I want to do. There’s always something. When you’re looking to, god, the next quarter, the next month, the next year, right? The next five years. What are all the things that you haven’t done yet that you’re going to go do? It’s constant. And personally, I find that my biggest growth moments as a person happen in those times of discomfort.
Kelsey Ramsden: And so here is the trick though. I want to say this to the listeners who are like, “Well, I can’t relate because I haven’t made a million dollars.” Look, you can because it’s the exact same thing. When your bank account has $7, and I have been in the $7 … I’ve been in the minus many, many dollars too.
Melinda Wittstock: Oh, me too.
Kelsey Ramsden: There’s a feeling of lack, and of battling back, and I’m not doing it right, and I have to do everything-
Melinda Wittstock: Yeah, and I’m not enough.
Kelsey Ramsden: [crosstalk 00:25:30
Melinda Wittstock: Or it must be something wrong with me. All that stuff. All those feelings.
Kelsey Ramsden: Totally. And do you know the piece about it that I wish I could go back and shake myself at 26, which was when I started my company. And tell myself that who you are is not what you do. And just repeat it.
Melinda Wittstock: Yes, please.
Kelsey Ramsden: Who you are is not what you do. Because I attach so much of my own value to that bank account number. So when I was at $7, I felt like I was worth $7. And I thought that if I could make a million dollars, I would feel like I was worth a million dollars. And here’s the sad thing. I made a million dollars and I didn’t feel any different.
Melinda Wittstock: Right. And this is the truth because the inner value, when we value ourselves, oh gosh. It’s like a very much an internal thing. When we value ourselves, we’re more able to value others. When we value ourselves, we’re more able to create value for other people, which is the essence, I think, of an entrepreneur.
Kelsey Ramsden: Yes.
Melinda Wittstock: And so where this came around for me is really around mission. If I had a big mission or a big purpose, what’s my purpose in life? What’s my unique ability? Why am I here? Why am I in an earth suit at this moment in time in history? What is my unique contribution? How can I double down on that and how can I serve and create value for the most people? If I’m thinking that way, then I’m fulfilled no matter what’s in my bank account because … And then I also have this kind of surety that I’m working towards something. That it’s a journey. And I’m more likely then to enjoy the journey rather than the destination.
Kelsey Ramsden: Yeah. And I mean, I think … I was listening to a podcast the other day and it said, “You know the truth by how it feels.” And I think that that feeling of not being enough or not having enough or constantly being in pursuit is really about … Like to your point around what is it that I’m actually doing, I spent a lot of years chasing … It’s funny now. But it wasn’t funny at all at the time. Chasing being approved of, being liked by being important and being wealthy. I thought those two things were the same-
Melinda Wittstock: [crosstalk 00:28:24
Kelsey Ramsden: When I got power and wealth, people would hear me and respect me.
Melinda Wittstock: [crosstalk 00:28:26
Kelsey Ramsden: Yeah, of course. That’s what I thought. I very much grew up in this kind of way of if you perform, you’re worthy. If you get straight A’s, you’re a good kid. If you’re the captain of the team, you’re better than everyone else on the team. If you score the most goals. Right? It was all about performance driven admiration. So what makes you loved more than when you were the best? [crosstalk 00:28:57
Melinda Wittstock: Oh, when you’re vulnerable. See, that’s-
Kelsey Ramsden: I didn’t know that. I didn’t know that. It is.
Melinda Wittstock: I didn’t know that either. I did not know that either.
Kelsey Ramsden: Oh. So hard. What a hard reality. Because when you’re built up, when you succeed through this kind of pressure cooker of only when you’re the best, are you loved and valued. The thing you want to be least is [inaudible 00:29:23, absolutely not. That … Whoa, no, no, no. You see, because I am only good because I am insurmountably strong. You will never break me. You can’t … Try me. That used to be in my mind. When things would go wrong, I would just say try me. Try me. And what a powerful statement. And I created a lot of amazing things. But do you know how painful, and isolating, and just destructive that ultimately that was? I honestly merit that to the greatest gift I ever got, which was cancer, I believe with every cell in my body that cancer came to me to save me from myself.
Melinda Wittstock: Gosh, tell me a little bit about that. So you’re diagnosed. How long ago was it? And what type of cancer was it? And-
Kelsey Ramsden: Yeah, cool. So it was seven years ago now. And it was my … Our youngest child was two months old. I went in for his check up. When you have a kid, they check them after a couple months. And my GP said, “We should do your physical.” I said, “I’m busy. I have all these kids here.” She said, “My nurse will watch the kids. We’ll do it. You’ll be busy anyway.” So we did it. And they found some irregular cells on my pap smear. And called me back. Which is a common thing. It’s not a big deal. Called me back. Fine, fair. And they say, “Well, you have cancer. We want you to come in for another biopsy.” So I do that. And I go into the room with my husband for the results. And then the surgeon comes in and says, “Congratulations, you don’t have cancer.” And I’m like, “Start up the car.” I’m stoked. I’m like, “This is the best thing ever.” And my husband’s like, “Wait a minute. Can you just … Because it sounded like it was pretty urgent. Kelsey’s been back for all these tests. Within a week, she’s been at the hospital three days.” And so he goes, and he looks, and he comes back. He says, “I’m really sorry. I read the wrong file. You do have cancer. And it’s not good.”
So the type of cancer that I had is called Glassy cell adenocarcinoma. It can show up in many places. But in my case, it showed up in my cervix. It had a 17% survival rate at that time. And does not respond to chemo or radiation, which is why it’s so deadly. And so you just have to get lucky and find it early and hope that the man on the knife or the woman on the knife does a good job of cutting it all out of you.
Melinda Wittstock: Wow.
Kelsey Ramsden: Yeah. It was totally a different experience. But the reason that I say … It was about the same time that I was named Canada’s Top Female Entrepreneur that I found out that I had cancer. It was the second time that I won the award that I found out I had cancer. And I will often tell when I’m speaking, I’ll say the best and the worst thing happened to me within the course of a week. And I’ll say this award and the cancer. And people often assume that the award is the best thing. But the award was actually the worst thing, I think, that ever happened to me. And the cancer was the best thing. And the reason I say that is I have spent all of my career life chasing, biggering the money, and driving, and working myself to death. Our first two children I had on a Thursday and a Friday. And I was back at work on the Monday with those children in my office. I never took a day off.
And the cancer was such a gift in that it reminded me of two things. Number one, how ultimately tremendously insignificant I am. In the grand scheme of things, 6000 years from now, the fact that I lived will not even … Who knows their great great great great grandfather’s name and what he did for work? So why am I killing myself? What is it I’m doing here actually? So if I’m tremendously insignificant, how about I spend my days doing something of purpose that matters to me as opposed to this idea of what matters in the grand scheme. What a gift to be given the recognition that I am totally insignificant. It was amazing. And at the flip side, how ultimately important I am to a very few people. To my children, to my husband, to my family, I am so valuable. So why am I wasting all my time and energy and not really being serious about what am I doing with that time and energy?
Back to the very beginning of our conversation when we were talking about doing all the things. What are all these things actually doing for me? If I’m at my computer, am I delivering results or am I lost in some Facebook thing?
Melinda Wittstock: Well, here’s the thing that so many people forget in all the doing. They forget the why they’re doing it. But what’s the actual outcome?
Kelsey Ramsden: [crosstalk 00:34:47
Melinda Wittstock: I do a lot of mentoring. And I was mentoring a woman not so long ago who on every call, she would come with new ideas of things she was going to do. And it was all doing, doing, doing, doing. I could do this. Or I could do that. Or I could do this. Or I could do that. And I kept hearing it over and over again. And I don’t think she was really hearing me because I’d keep coming back. And so like, “Okay, well, why are you doing those things? What do you want to do? What is the outcome that you want? Can we think about outcome?” And you know what? All these ideas were all things that she could do, but she had no idea. No idea what she actually wanted. Or why she wanted them.
So for … Entrepreneurs are like idea factories, right? There’s billions of things we can do. But sometimes in the doing, we’re actually avoiding. But with real work, the real inner work that we need to know to really find what that purpose is. And then be able to choose the activities and the doings that are going to actually have the most leverage in our lives. Right? Like what’s … If we do this thing, how many great impacts will happen from this thing as opposed to doing this other busy work over here which will just keep you on a tasks treadmill all your life.
Kelsey Ramsden: Yeah. Cool. Can I approach this from two different sides?
Melinda Wittstock: Oh, gosh, yeah.
Kelsey Ramsden: [crosstalk 00:36:15 two things. So one is this idea that there are a lot of people that I know who are very capable. Have great ideas. That what they could do is amazing. But they sabotage themselves in a very explicit way that is super obvious to many of us. But to themselves, they’re in the dark and they wonder why I never scale, or why I’m stuck, or why am I not growing? And the reality is, they take everything to the 80 yard mark. There’s 20 yards to go. Whether it’s making the sales call or actually showing up prepared and not winging it or whatever. Because they either do not want to prove how good they are, because that demands a whole other level of professionalism. Or they don’t want to prove that they’re not that good. Having a dream sometimes is a lot better. Having a dream sometimes is a lot safer. And so if you’re an 80 yard mark person, you’re either really amazing or you already know that this is 80% of the work you could be doing and it’s not that great but it’s easier to have a dream. And that’s a terrible thing to say. And I feel a bit like Kevin O’Leary on Dragons’ Den or Shark Tank. But it’s true that a lot of that kind of getting part of the way is a result of one of those two things.
Melinda Wittstock: Do you think a lot of women in business have a fear of success?
Kelsey Ramsden: Yes.
Melinda Wittstock: I want to flip this around because you were talking about you thought for a long time, as did I, that I would be liked, and revered, and all this sort of stuff if I was super successful. So that kind of propelled me through my 20s and 30s and even into my early 40s. Until I realized that actually, no, that was just isolating.
Kelsey Ramsden: [crosstalk 00:38:08
Melinda Wittstock: And no, it did not make me … It did not … Right, it just … It was completely wrong. And so I wonder though whether there’s a lot of women who kind of know that intuitively already on some level that they think that by succeeding, they literally will be cast out of the tribe. Like other women won’t like them, men will be intimidated by them so they won’t find a partner or a great lover. Or [crosstalk 00:38:39 all those sorts of things. So it’s actually fear of success for a lot of women that holds them back.
Kelsey Ramsden: Yeah, which is totally unrelated. And I will say that’s all true. More men will be intimidated by you and more women will dislike you. And that’s … In my experience, that’s been actually very true. But the men who do like you will be able to handle you [crosstalk 00:39:02
Melinda Wittstock: Exactly. They’re better [crosstalk 00:39:03
Kelsey Ramsden: They’ll be the man you want, right? And the women who can handle you will get you. You’ll finally … You’ll be at the dinner party and be like, “I want to talk about these things. Oh my god,” it’s not like [crosstalk 00:39:15
Melinda Wittstock: Oh man.
Kelsey Ramsden: [crosstalk 00:39:15 we’re talking about the same. Do not be afraid. Go fearless into the dark night of … We’re on the other side and we’re waiting for you. And it’s super bad ass over here. And we have a great time. There’s not as many of us. But if you’re like us, you’ll fit right in.
Melinda Wittstock: Oh, I love how you said that. I mean this has been so true of my life. Just in starting this podcast for instance, I have created the most amazing relationships with women that I never thought possible. Like earlier in my life when I was harnessing my inner dude.
Kelsey Ramsden: Mm-hmm (affirmative).
Melinda Wittstock: Right?
Kelsey Ramsden: Yes, totally.
Melinda Wittstock: Because I thought I had to be a dude to succeed and all of that. And I didn’t have a lot of women friends. I mean, I’ve always had a few. And so it’s so interesting for me to end up with this podcast and do all this work. And my whole mission now is around women which [crosstalk 00:40:11 wow, that’s kind of funny. How did that happen? And the more … Yes. So I’m just going to pick up there. I found that … Well, again, I love, Kelsey, what you said about this come over to the other side because on the other side, there are these really badass amazing, amazing women. I just feel so connected, so empowered, better than I have ever felt in my life for those relationships.
Kelsey Ramsden: And here’s the thing. And to your point around kind of the fear of success. I think it’s actually not that we fear success in and of itself. I think what we fear and I think this is where that conversation has turned so many people away. Because I always [inaudible 00:40:59 who fears success? That’s ridiculous. Everyone wants that. It’s that we fear what happens to our relationships, which is usually what matters most to the feminine. We fear what will happen to our relationships when that happens. Will this stress test my marriage? What will this mean for my time with my children? What will this mean for how my current group of female friends engage with me? Think about me? Talk to me?
And I think that … If I may take this moment to talk about relationship and we touched on it at the beginning of the show. I think a lot of people, if they’re honest, and if they’re suck in their business at whatever level. I don’t care if you’re making $300 a month in your business and you still have a job. And you’re kind of just trying to get this thing off the ground. Or if you’re making $300,000 a month in your business and you’re seemingly doing okay. Everywhere in between, we have a network of people around us. And we have relationships with them. And for a long period of time, I think most of us don’t really look at those relationships under the lens of two things. How can I serve you that actually benefits you? It doesn’t benefit me. How can I actually serve you not in a martyr type of a way. But in a is there something I can do to better your situation? And if I think about this in a really obvious form, when you think about a child relationship. If your child comes to you and says, “Can you find my socks?” The correct answer is, “No, because you can find your socks.”
So serving them in saying no sometimes is still the answer. So I don’t want people to get overwhelmed by thinking, “Oh, I’m just going to do everything for everyone else.” No. You’re going to do the appropriate amount of work for all the people that you’re in relationship with. That includes at work. Whether it means sending the email back that says you can find that here as opposed to answering the question for them. Or in your personal relationships.
The second piece, that was the leverage piece. So now once you’ve streamlined your time and you’re serving all the people in the appropriate ways, if you want to leverage your time and your relationships, which is particularly what women do well, I want you to get a piece of paper, draw … You know when you throw darts, it’s a dart board. Like concentric circles. There’s one right in the middle and then some that go out from that? You know what I mean?
Melinda Wittstock: Mm-hmm (affirmative).
Kelsey Ramsden: I want you to draw that and i want you to think about … And then make some pie shapes around the outside. One can be career, romantic, health, faith. Whatever. Break your life into the things that it’s comprised of. And then in each of those things, draw the relationships that are closest to you. So in my career, the relationships that are closest to me are probably my accountant, my assistant, whatever. And out you go. Same with my regular life. My husband, my closest friends, my family. Out you go. And the reason that this is valuable is for two things. One, don’t listen to the sound that come from the people on the furthest circle out. Their voices probably shouldn’t be heard. And oftentimes, we let those people be a critic. And the second thing is look for the holes. Because more than likely, there are people that you know who you could actually make an ask of, who you can lever off of appropriately who are in those circles.
Look, if I need help with something … Let’s say I get into a sticky situation at work and I need a lawyer. And I don’t know one. And da da da da. I’ll bet dollars to donuts there’s someone that I went to undergrad with who I can reach out to who I now know is involved in business. And say, “Hey, I have this situation. Do you know a good lawyer?” And they will tell me. And it will be a referral. And it will be someone they trust by someone I trust. But instead we hide out making small. Making ourselves the center of this world. Not allowing any other people to be the hero. What if you let someone else be the hero? Imagine that.
Melinda Wittstock: Ah, it’s beautiful.
Kelsey Ramsden: Honestly, that’s how I scaled up my … That’s how I even got started. If people think I showed up as this big success story, I showed up being $112,700 in debt. When I quit my consulting job, that’s how much money I owed from my MBA. And the only thing I knew how to do was build roads. And I reached out to someone that I used to work with … For, actually. And I said, “You know that I work hard. Will you bond me to take on jobs? I’ll do all the work. And I’ll give you half of the profit.” He said, “Yeah. Of course.” So I made him the hero. He was the hero. But nobody takes the time to ask the question about how did you really get started. Who did you have to ask for help? Where did you have to check your ego?
Melinda Wittstock: You have to do that to succeed as an entrepreneur and it’s so important in terms of building a team. You have to make your team heroes. Especially when you’re starting and you have nothing. I mean, we all start companies often with nothing. You start it with debt. I mean, I started a company with an incredible debt from a previous … From a marriage that was toxic for me that I got out of. At post-2008 where I lost everything. Right? And so sometimes you just have to start from negative. And the only way you can do that is yes, you do have to check your ego at the door. You do have to ask for help. And you have to reward it. And you know what? You’re creating a bigger pie that way. And so maybe you have a smaller proportion of that pie, a smaller slice. But the pie is much bigger.
Kelsey Ramsden: Totally. And you look at the people you surround yourself with and you say who can I ask for help? In a way, that makes them the hero.
Melinda Wittstock: Yes, exactly. Because then that way, it gets out of that kind of thing where you feel like you’re showing up with a begging bowl.
Kelsey Ramsden: Yeah. And you’re doing all the things. And you have to do all the things. And you’re the only person who could do it. Look. No offense to anybody. We’re all … If I look at my bio, cool? And you say, “Kelsey Ramsden, MBA, Top Female Entrepreneur,” all the things that you list about who I am-
Melinda Wittstock: Mm-hmm (affirmative). And you’ve done a lot in your life. You’ve achieved so much.
Kelsey Ramsden: For sure.
Melinda Wittstock: I mean, your bio is extraordinary for anybody to read.
Kelsey Ramsden: For sure. Yeah. I’ve done a lot of things. But guess what? There’s the million other people who’ve done all those same things. That even though you can … There’s only one Top Female Entrepreneur of the year in Canada each year, there’s another one this year, and there’s another one next year, and there’s another one next year. And so the point being is that for years, I created a business out of this very kind of masculine sense to your point of duding up. Of being so required, so needed, so absolutely the only person who could do it the way that it needs to get done in order for it to be right. And I let that hold me back. And I think so many people I talk to who started out and they’re stuck in that first level. They just can’t … They’re like, “But I can’t leave. I have to work. I have to …” It’s that little moment where you realize there’s a lot of other people that are really capable who want a chance. Why don’t you just let them do it?
Melinda Wittstock: Right. Oh, gosh. Yes. This is so true. So I had a question though for you. Specifically about building roads. There are not a lot of women in road building, I imagine. Or are there?
Kelsey Ramsden: No, there are not. [crosstalk 00:49:39
Melinda Wittstock: Were you really often the only woman in the room and tell me, what was it about road building that caught your imagination that you wanted to go build roads?
Kelsey Ramsden: Yeah. You know what? My family was always involved in construction whether it was they had a trucking company or my dad was involved in construction so I worked construction for him. Then my parents retired in the late ’90s. Well, they moved off shore and they did construction work in the Caribbean. So I went and worked for other people. Because you can make a lot of money in a short period of time. So I liked that job. So I’d go to university and I would do my undergrad. And then in the summer, instead of working as a waitress or whatever else, I’d go and work construction and I’d make three times the amount of money in the same period of time as other people. Well, I like that. And then I went and did my MBA and all these kind of things. And then I can remember walking in … So after my MBA, I became a business consultant. And I walked into my office and I looked at my boss and I thought if I had $100 to put on her or me, who would I put it on? And I was like, “Ugh, put it on me.” So I quit.
And I called my now husband, but we were dating at the time, and I said, “I quit my job today.” And he knew I was unhappy. He said, “Congratulations. So what’s the plan?” And I said, “The plan is that you don’t quit your job because I don’t know what the hell I’m doing.” And so I just looked and I thought, what is the one thing I know how to do? I could do it with my eyes closed. I know how to build a road. Okay. So who do I know? Okay, I used to work with all of these guys. What if I called them and I said, “Do you want to work with me? Except I’ll sign the checks. But we’ll work together just like we did before and we’ll build something.” And so that worked out. And then they needed bonding. And I called somebody I used to work for. And just like I explained. Said, “If you bond me, I’ll give you half.” And kind of just piece together this idea of a thing and that’s what led to what is now today a decent sized construction company.
We just opened offices in the Caribbean too. So now we’re expanding it all by virtue of, and in fairness, very much my family’s support. Whether it’s my mom and my dad and the experience they gave me or them supporting me even now. When I had cancer, I called my dad and said, “Can you come back and work with me?” And he worked with me. And my brother who’s an amazing entrepreneur who’s founded [Zack’s 00:52:03 underwear and did a bunch of other things. And he works with me. So really, surrounding myself with these amazing people and never … For me, oftentimes I had to get to the place where I had to learn a hard lesson. I had to get cancer to realize I was wasting my life chasing after something that would never fulfill me anyway. I was hoarding all the work trying to make myself feel important when there was tons of people around me who could’ve done just as good at a job or better.
And so now, we’re at this place where I learned the hard lesson, I had the success hangover, and I’m so much better for it. I still run the businesses. And I’m so grateful for having really been a woman in an industry where there weren’t many because I was ignorant to that thing. I didn’t realize how much it was playing into a lot of the things that were going on. I just always thought if you did a good job, no one could deny results. And so I … Because I was always different, I had developed an antibody to judgment a little bit.
Melinda Wittstock: I love that. An antibody to judgment.
Kelsey Ramsden: Yeah.
Melinda Wittstock: What an intriguing idea. I mean, I think that what’s interesting about the concept of judgment and how funny that this should come up today because I was just talking about it with a colleague of mine yesterday. How people are very prone when they’re not conscious to judgment. And of course, judgment is we put our own kind of judgment on other people’s activities or whatever. And often it’s a chance to … When we’re judgey or we’re feeling judgey, it’s really an opportunity to look within. What is it about this that’s triggering me because I probably have something unresolved that I need to let go of. Some sort of belief or whatever that’s leading me to that judgment.
Kelsey Ramsden: I think one of the benefits though of that … Look, here’s how I developed my antibodies to judgment. I didn’t recognize the culture. So let’s just say I go to China and I’m unfamiliar with Chinese culture and I do a bunch of offensive things but I’m ignorant to that’s offensive, I don’t even notice it. And so for me, being a woman in a man’s business, I was ignorant to their culture. I just went ahead and did my thing. And they were offended by it and I didn’t even know because I was winning. I was like, “Well, this is all good. I’m making money, everyone likes working here, this is all good.” And I was disrupting their culture without even knowing I was doing it. And so I think this piece around developing an antibody can happen in two ways. Either it can happen through ignorance or you can decide that you’re indifferent to their opinion. How does it actually … Do I have to take that personally? What I was talking about before with the concentric circles and those people on the outside we allow to be our inner critic. We open the door and we’re like, “Hey, you’re way out there on the periphery doing nothing. You’re lobbing tomatoes at me from the far reaches of the effort here. Welcome in. You should stay with me all the time. And get right in my head. And tell me how I’m wrong.”
It’s insane. But we allow that judgment in. So to me, the antibody is just really being clear on who the critic is. Is the critic valid. And I think back to that thing about we know the truth on how it feels. Sometimes they can say hurtful things. But it hurts either for a reason because it’s true a little bit. Or it hurts because they’re judging. And actually that hurt is not about me. It’s about why is it that people have to tear other people down? I live in a paradigm where we build people up and you’re disrupting my paradigm by being just a critic. So it’s really not about me or the thing they’re criticizing. It’s about my belief that … Play on your own field, man. You’re welcome on my field if you’re playing.
Melinda Wittstock: So this is so wonderful and so important for all entrepreneurs to really understand. And I wanted to dive in a little bit to what made you write your book. It’s called Success Hangover. What was the hangover? Why hangover? What was the success hangover and how did you get kind of out of that hangover, if you will?
Kelsey Ramsden: Yeah. So here’s the thing. And I’m okay with talking about it because no one has been. And anyone who hears those two words together who’s had one, understands it inherently.
Melinda Wittstock: Mm-hmm (affirmative). Yes.
Kelsey Ramsden: But there’s this idea that because you set out to accomplish a thing and you accomplish a thing, you should be happy and grateful. And this idea of the success hangover, people shamefully don’t talk about arriving at the place post-peak. Which is I got there, I climbed, I overcame, I’m standing on the mountain, so now what? And a lot of people in that so now what can have a really hard time either coming down the mountain gracefully and finding a new mountain or deciding that there even is … Which mountain next? Never mind that.
Melinda Wittstock: Oh gosh. You remind me of something that Ping Fu told me once. So for those of you who don’t know Ping, Ping invented 3D printing. And before that, she invented Netscape working with Marc Andreessen of Andreessen Horowitz. I’ve actually hired Marc. Way, way back. So Ping is a badass. She’s now on the board of Burning Man. She’s amazing. And she’s from China. She arrived here with only kind of like $10 in her back pocket and no English as an 18 year old. So extraordinary story. She says the problem with walking to the top of the mountain, as you get there and you only have one view. You have to come back down again to be able to climb the next one. So it just reminded me so much about what she was saying, which is so true. And so part of the success hangover, I mean, to go full circle in our conversation is if we confuse the destination with the journey, that the destination isn’t the thing. It’s the journey. So you achieve success and you feel this kind of emptiness. Oh, oh. Well. There were supposed to be fireworks, I was supposed to feel different. Something was supposed to happen to me.
Kelsey Ramsden: Yeah. I was supposed to feel whole. This was supposed to be it. I was supposed to be done. It was supposed to be good. It was supposed to be obvious. [crosstalk 00:59:41
Melinda Wittstock: Right.
Kelsey Ramsden: Enter every single thing. And so what happens for most of us is we have this immense feeling of nothingness actually. We’re quite numb after that. Like I would ask … So anyone who’s listening, thing of that time. Whether it was you graduated high school, you got the promotion, you got your undergrad, you made the first $10,000. Whatever. And then the first thing was so now what? And you have this real kind of antithesis feeling as opposed to feeling accomplished and like the “succeeder,” you feel in lack and lost. And so the book was really written … It’s a book I needed someone to write for me when I had my biggest one, which is when I won that big award the second time. And I thought, right, so how do I follow this damn act? What now? How much bigger can I get? How much more money can I make? What’s more successful than this and I still feel terrible? What’s going on? And it took me three years to come out of this funky fog. It was terrible. But no one talks about it. It’s not politically correct to … Oh, poor successful you.
Melinda Wittstock: Right. You feel you have no right to …
Kelsey Ramsden: [crosstalk 01:01:13
Melinda Wittstock: This is so interesting though because in a number of my different entrepreneurial groups, this is all morphed into right, what’s your purpose? Can you … Perhaps you built a great product or a service, perhaps you built a platform. But now, what can you do? Can you create and catalyze an ecosystem? Right?
Kelsey Ramsden: Right. So many of us walk around calling it burnout, but it’s actually bore-out. We’re bored as hell. And no one wants to admit it. And no one wants to change what we’re known as because we started this show. What if I don’t want to write another New York Times Best Selling Book but that’s who I am? No, that’s not who you are, that’s what you do. What if you don’t want to be the leader at Netscape anymore? That’s who I am. No, that’s what you did. So this idea of attaching our ego so closely to what we succeeded in is one of the worst things of all time. And [inaudible 01:02:15 to find that purpose, the thing you’re talking about that really drives us, you have to arrive at who you are. Well, that’s frightening as hell isn’t that? Who am I really? And so that’s what the book was all about was my journey in that and a bunch of the neuroscience, a bunch of other colleagues who’ve arrived at places that we would call success. Found the hollow place afterwards or the shady side of that. And then realized that success is not singular. We can do it again. And there’s a really specific way we can do it to either eliminate or abbreviate that post-success hangover.
And look, I lost a friend to it last year. We’ve seen very public losses. Anthony Bourdain, Kate Spade. There are people literally dying from arriving at the top and not having a place to go. Experiencing the hangover and not knowing how to move through that. Or feeling like is it even okay to talk about? Or anyone wouldn’t understand.
Melinda Wittstock: Right, this is so, so, interesting and such important work. And thank you for writing that book. I know from working with entrepreneurs who are working towards exit of their companies and then after they’ve sold, that kind of emptiness. And in fact, the work I do with Steve Lit … So in fact, the work that I do with Steve Lit … I can’t even speak. God, what’s wrong with me? In fact, the work that I do with Steve Little at Zero Limits Ventures is very much about this. Because when he’s doing valuation growth, he’s one of the sponsors of this podcast. When he’s doing valuation growth work with entrepreneurs to get them to exit, increasingly he’s working with them to help them find their purpose and their mission as part of this whole exit strategy. Because if you don’t look at it in that holistic way, you can end up exactly what you’re … Exactly where you’re talking about. So I see him do some incredible work with founders. And having sold so many of his own businesses and many other founders’ businesses, that without that purpose, it’s very, very, difficult-
Kelsey Ramsden: To sell.
Melinda Wittstock: Yeah, to kind of sell your baby first of all. But then to oh my god, now what? So I have this money, but I have no purpose. Right?
Kelsey Ramsden: But here’s the thing too though. Because I don’t want people to get dissuaded by thinking I’m not that successful. Because the reality is this same thing happens to us at all levels of success. It happened to me … I can’t remember the first time it happened to me, I was 21 years old. Second time it happened to me I was 27. Next time … This happens on multitudes for people who are achievement driven. If you’re an achiever and a driver, you understand this, and you don’t have to sell your company in order for this to be a real experience for you. Just has to happen the first time you hit your mark and realize now what? Now what? Now what? And so, yeah. To me, the book was not only about being the person for someone else that I needed when, which is I think what a lot of these kind of pursuits are about. But it was also a little bit about recognizing the creative pursuit in all we entrepreneurs. And really helping people like us feel like and understand that there are legions of us going through the same processes. You know how I opened about how is it that you get out from the bottom and arrive at the top and choose to do another mountain?
And so the book is both a good read and then there’s a bunch of exercises that I put in there that I just created myself. I mean, I’m not a guru or a knower. I’m just a person who did okay and had to go through a bit of work to come out the other side. But I will say there are about five things in my life I’m proud of. And of which, the book is one.
Melinda Wittstock: Beautiful. Kelsey, it’s such a delight to talk with you. I would love to have … I mean, I think we barely even scratched the surface even though we went so deep because I think there’s so much to talk about. So you’re going to have to come back on the podcast later in this wonderful New Year of 2019 and share where you’re going. And let’s just leave off here with what’s new for you? What are some of your big new goals, missions, whatever looking forward to in 2019, and to 2020, and beyond?
Kelsey Ramsden: So 2019 and 2020 for me are three things. Number one, we just expanded into the Caribbean. So a huge focus on building that business, which is a great opportunity to do it again. It’s really enlivened me to be at the start, which is awesome. The second thing is really staying in this pattern of being clear about where I need to be of service and making sure that I do that across my life and my business. So not creating this kind of co-dependency of need for those things I think I could maybe do better. And being reminded of this idea that I have notoriously high expectations and being okay with that. And then the third thing is being of service to the book. I thought I would write the book and be like, “Oh, that’s good. It’s done.” But what I’m learning is that the book demands of me an attention and that is only worthy of the kind of response. And so when people take the time to pour their hearts out and tell them about life changing things, you got to show up and receive that. And so I’m booking out … Yeah. It looks like I’m doing a world tour, which is cool. So I guess that’s what’s also happening next year.
Melinda Wittstock: Oh, that’s awesome. So how can people find you and work with you and get your book?
Kelsey Ramsden: Yeah. Right on. So they can find me predominantly on Instagram @KelseyRamsden, R-A-M-S-D-E-N. They can check out the book at successhangover.com. Or just use the old Google. Find Kelsey Ramsden. I’m out here and always interested in engaging in interesting conversations.
Melinda Wittstock: Oh, that’s wonderful. Well thank you so much for putting on your wings and flying with us.