Syama: Women don’t talk about money the way we should. Not honestly, not openly, and not with each other. But that’s changing. I’m Syama Bunten, founder of Wealth Catalyst. And Getting Rich Together is where the conversation lives. Every week, a different woman, a different path, and a conversation that will change how you think about your own financial power. This community is growing and you belong in it.

Please subscribe so you never miss an episode and leave us a five-star review so more women can find their way here. Now, let’s get rich together.

I am here today with the fabulous Andrea Liebross. Andrea, when we connected, I was so in awe of your spirit, the way your mind works, and the energy that you bring into the room. That was doubled down and reinforced when you hosted a Wealth Catalyst salon this year. Your ability to bring together intelligent, smart, brilliant women who are heart-centered and curious about the world is an incredible gift. I’m so honored to have you here today on Getting Rich Together.

Friends who are listening, Andrea Liebross is a business coach, keynote speaker, and best-selling author of She Thinks Big. She is the go-to strategic partner for high-achieving women who are already building results-driven businesses that actually fit their lives, not just what society tells us things should look like, but building from our inner being outwards. Through her She Thinks Big podcast and her year-long She Thinks Big collective, Andrea helps established women business owners think bigger and become the women they’ve always meant to be, creating the life of their dreams without burning out. Which is something I felt like I needed just getting on the call with you today. So Andrea, welcome to Getting Rich Together. I’m so grateful to have you here.

Andrea: Thank you for having me, Syama. I’m excited to be here.

Syama: You undoubtedly are so fabulous. Everyone who knows you comments on how well you dress, how articulate you are, how supportive and helpful you’ve been in their business and their growth and their success. But certainly someone like you was also once a little girl, maybe not always dressing so fabulously, or maybe she was. Andrea, take me back to a little girl somewhere around the ages of ten and twelve years old. Where were you in this big, beautiful planet of ours? What was life like and what was money like around you?

Andrea: Well, I was a little girl growing up in a suburb of Boston, Winchester, Massachusetts. My parents still live there. My brother still lives there. Everybody’s still there except me. It was suburbia, is suburbia. Winchester is a town about eight miles north of Boston. It’s on the commuter rail, so a lot of parents and friends were commuting into Boston on the train.

I have one younger brother, four years younger than me. My dad is a CPA and he started his own business when I was five. I literally remember when that happened. My mom taught elementary school, middle school, community college, so she was working part-time at that point. My dad was really hustling and growing his business. He was teaching college classes at night, plus the accounting. I was probably around sixth grade, and I thought I had my act together at that point.

In terms of money, what’s interesting when I reflect back is that money was talked about, but in a very contained way. Almost like it was in a box. I had a bank account and a little quarter collector for Christmas, one of those cardboard collectors you got from your local bank, and every week maybe you’d put a quarter in there. Saving money was something that was talked about. My dad was investing at that point in some properties, and I remember that kind of discussion. But I don’t think I had any real sense of what things cost in the world at that age, what it costs for a family to live day to day. I remember everybody had to shut off the lights and turn down the heat because that costs money, electricity. I remember those kinds of things.

I did not have a great sense of the cost of things, and that really wasn’t talked about. My parents will probably never listen to this podcast, but there were definitely dynamics like my brother should do this and I should do something different. So there was that going on. In another way, I was kind of raised to believe I could do anything I put my mind to, but only to a point, I guess. It’s an interesting thing to think about now. My dad is 87 at this point. He still goes to work every day at his practice. He has an office of maybe fifteen people, but he still goes in every day. And he still talks to me about money as if I’m ten, which is really interesting.

Syama: You’re like, Dad, don’t you see?

Andrea: I don’t know why that is, because I hear him talk to his clients in a very different way. I’ve heard so many of those conversations. That’s what I remember as a little girl too, listening to him talk about the properties they were investing in. I was just in the background, listening. But I was never really brought into the conversation.

Syama: That’s interesting. Do you find yourself turning off the lights today, doing any of those things?

Andrea: That’s a great question. Not really. At this point I kind of feel like I can create money if I need it, so I can create it, and if I want the lights on, they’re on. I do turn the lights off when we leave the house, but it’s not that same run-around-the-house energy of dad’s coming home, everybody shut off the lights, turn down the heat. And you know what, that was probably partly my mom, not my dad, to be honest. Those were things she was telling us to do because she was working part-time in these teaching roles, so she was home with us, my brother and I, much more than my dad was. When he came home, it was everybody has to get their act together.

I did have a store made out of a cardboard box that we would put out on the corner, kind of like a lemonade stand, except we sold painted rocks. So maybe that was my first entrepreneurial adventure, now that I think about it.

Syama: And then you never looked back, right?

Andrea: Painted rocks. So if Andrew and Laura, my neighbors, are listening, we were the three storekeepers, and we sold painted rocks. There you go.

Syama: I love that. Tell me what you did with the quarters. It’s so cool to think about little you, getting her quarters and squirreling them away. Was it with the intention of I’m doing the right thing? Were you saving for something? How did you think about the act of literally taking the quarters and putting them aside?

Andrea: I think I was really thinking about it more as not buying things for myself, not investing it so it could grow into more money, but saving up so I could give something to someone else. It was almost a gratitude activity, a gifting opportunity. That was how I thought about it. I do remember understanding interest, how I could get some interest on money in the bank account, but that wasn’t of utmost importance to me.

Side note, my brother was totally different. He was all about making money. He would charge me for things.

Syama: That’s so sweet.

Andrea: He would say, well, that’s going to cost you a dollar. He was all about making money, in all sorts of ways, a hundred percent.

Syama: This show’s about you and not him, but is that still part of his identity?

Andrea: A hundred percent. He went into investment banking, and then he was ultimately a principal at a private equity shop. He retired at age forty-six or so and plays golf all the time now, and investing is his full-time job at this point. So yes.

Syama: It’s so interesting to think about these stories from when we were younger, and even getting the chance to know you today and over the last year, this spirit of generosity is still very much alive inside of you and part of what centers how you give and how you lead. It’s wonderful to learn this story about you as a little girl.

Okay, talk to me about Andrea the high school student. Did you keep the entrepreneurial thread going, moving on from rocks to bracelets or other things? Was it heads in the books? Was it sports? What was it like?

Andrea: I was a really good student, so heads were in the books. I played all sorts of sports and I was very into theater. I had summer jobs, but I saw them more as opportunities to explore things I was interested in than as pounding the pavement to make money, even though I was making money. My parents always had us have a job in the summer, though I didn’t work during the school year. I worked in a jewelry store, I was a camp counselor, I was a lifeguard, I did a lot of babysitting, and that all fit in between the other things I wanted to do.

That was who I was, and then I graduated high school and went to Dartmouth College. Again, that was more about opportunities for growth, not financial growth necessarily, but personal or professional growth, creating connections, being exposed to different types of businesses. I think I was thinking the money will come. My brother was all in it for the money, always asking what’s the best financial investment, where can I get the fastest return. But my parents really weren’t like that, and this is something I’ve written about in my own book. I don’t want to say pushing, that’s a strong word, and I don’t want to say encouraging either, but it just wasn’t talked about. Nobody said, hey, you might want to go down this path because financially it might work out better for you. That wasn’t part of the discussion.

Syama: Interesting. So when you were pursuing your degree in history and psychology, did your parents never ask what kind of job you’d get with that?

Andrea: No, no one ever asked that. I find that so interesting, because now I’m a parent of two twenty-somethings who’ve both graduated college, both gone to business school, and both are employed, and that is definitely something I’ve talked about with my kids. What are we doing with this, where’s it going, what’s happening. There’s a little bit where you have to trust the universe that things will evolve, but that was very important for me to discuss with my own children.

Syama: Yeah.

Andrea: Maybe that’s because of my own experiences. I graduated, moved to Manhattan, lived in this roach-infested walk-up brownstone on East 52nd Street with two other girls, in an apartment with makeshift drywall walls, we’ll call them. I worked at a big advertising agency, one of the big ones, DMB&B at that time, and I was an account manager. I didn’t love it. I really didn’t love it. I stayed a couple of years, then I got married and went and got my master’s degree. Things happened. It’s interesting, and it actually kind of makes me mad thinking about it now. Why wasn’t I doing something different that probably would have been a little more lucrative? I don’t know.

Syama: Well, life has turned out pretty good, so I don’t know that it matters.

Andrea: Things are okay. Things are okay. But in that era of my life, I wish I would have been thinking a little differently. How about that.

Syama: Yeah. I think we’re often products of the guidance and mentorship, or the lack of it, around us. There’s an element of wayfinding where we’re constantly getting back to the children inside of us who were told we were wrong, and constantly reorienting ourselves to who we know ourselves to be. Strong mentors can provide strong direction, but not having mentors is also a big piece of feedback, and it forces you to learn in ways that someone with a lot of mentorship doesn’t have the same capacity to build. You’ve earned your stripes, Andrea. Going to New York after university isn’t easy. I feel like New York is a great place to be broke because there’s so much free to do, but it’s like you either want to be really wealthy or you can be a broke student. Those are kind of the two lanes.

Andrea: There’s only two extremes.

Syama: I think that’s it. And the wealthy people in New York are probably subsidizing the free programming for the broke students, there’s some relationship there. But how did you organize yourself, and what did you think of your young self? You graduate with this degree and go into advertising. Was that something you wanted, like I see myself as a career woman in this industry? Or was it more like, I need a job, where do I find one?

Andrea: No, I did want it. It was interesting to me. In the second half of university I’d gotten much more involved in neurolinguistics, how our brains process things, neuroscience, and that’s sort of how the whole advertising thing came about, because I was very curious how you sell things to someone, how you market or promote them. I was in consumer packaged goods within advertising. It was intriguing to me to figure out how you sell a box of Uncle Ben’s rice to someone in Alaska, or how you sell a Norelco electric shaver, that’s what they were called then, now it’s Philips, to a sixty-five-year-old guy. That was interesting to me, and I also liked how a big corporate structure worked. So no, I did go after it, and I got it. I felt like that was a coup, like I’d won a little bit there.

It was a really good experience. I did decide through that experience that I didn’t want to stay in that industry, more because of lifestyle than anything else. But all in all, I learned so much that I still use in my life today.

Syama: These are such formative years, developing the training ground. I remember in my post-university years, my first job was in the business development program at Macy’s, and it’s so interesting to think about that rigorous training at these big companies back then. When you have these opportunities to work in a corporate environment in New York, in a big industry, at a reputable company, you’re literally making it. The odds are so stacked against anybody, so there’s reverence for the experience, and there’s incredible training. You don’t really realize until after that in these young formative years you’re literally beaten into thinking and doing and performing. I don’t think young people today have the same experience, and I have to say, it was certainly traumatic. I’ve never heard a young person who worked in New York at a big company say it was easy. It’s usually filled with a lot of trauma.

Andrea: It is. My kids, my son’s been working in Boston for two years now, and there’s a little bit of trauma. I’d a hundred percent say so, for interesting reasons too. There was some trauma for me where I’d be sent to rent a car, drive to Stamford, Connecticut, to drop off an envelope at the headquarters for Norelco Shavers, then drive back to Manhattan, return the car, and get back to the office. I remember thinking, all because of this one envelope, there’s all this expense. I was the delivery person in that case.

Or I’d have to be the last person to leave the office, because I had to wait around for the creative people, this is in the days before computers, to finish creating, sketching, drawing, whatever they were doing, then take it from their hands, go down the elevator in the building on Broadway, to the FedEx office on the bottom floor, put it in the envelope, and hand it to the FedEx guy. I remember thinking, this is ridiculous, that I’m staying here for hours just to do that when the creative guys are getting in the same elevator to leave. Those things were sort of traumatic.

Syama: Yeah. Totally.

Andrea: There’s lots of other traumatic things that happened, but those are the memorable experiences for me. What is going on, what is going on.

Syama: What a great opportunity to have that experience of contrast, something’s wrong here, or this doesn’t feel right, even if you don’t know the alternative yet. In these first few years of building your experience, New York is obviously expensive. Were you thinking at that time about savings? Was university paid for, or did you have student loans to pay off? How were you financially navigating those years before your master’s program?

Andrea: I was definitely thinking about saving at that point, that was now in my brain. I was lucky enough not to have student loans myself, but my husband had med school loans, so we had to start paying those off. We also started thinking about where we really wanted to live for the long term. I started to get creative with asking for money in certain ways, and creating money in other ways. We figured out how to get money to pay off the entire student loan at once, and then pay that money back, at a much lower interest rate, to another human, not to the bank. We thought, this is ridiculous that we’re paying all this interest, why don’t we ask family members who might say yes to lending us this money, and we’ll pay them back at a much lower rate. I think that was around when I was twenty-four or twenty-five.

Syama: It dawned on you.

Andrea: Yeah, I was like, huh, this is a better way to do this. So things like that. We did the same thing with a car. We started getting creative, figuring out who to go to, who might say yes, who might say no, and what our case was.

Syama: That’s also a good example of sales. How do you position the case? What’s the language? Who’s the target audience?

Andrea: Yes, it’s so true.

Syama: And on a personal level, it’s also quite vulnerable. Getting over the fact that to get what you want in life, you have to ask. Asking means being prepared for disappointment, and also being prepared for a yes. I think so many people are scared of the disappointment that they never end up asking at all.

Andrea: I see that in my clients right now, the women I work with. I have a phrase I use: are you giving equal airtime to the possibility that someone might say yes? We naturally give more airtime to the no’s we might get, that’s how our brains are wired, to try to avoid pain or disappointment. Because of that, we don’t ask a lot of the time, even when we have a little glimmer that maybe we should. We just shy away.

Syama: It’s scary, and it’s not socialized the same way. I think boys are socialized to ask, and to keep self-advocating, keep going for it, even if you get a no. It sounds like you figured this out at a young age. Twenty-four, twenty-five is a powerful time to realize the power of your clarity and your voice. So you go get your master’s. Was the idea, I’m picking the school because it’s where my husband and I want to live in this region, or was it a specific program?

Andrea: So the change was, we moved to Houston from Manhattan because of his residency. I don’t know if you know how the match works for med school, but it was a choice in the sense that we ranked our preferences, but that’s where the match matched us. So we moved to Houston.

Syama: Yeah.

Andrea: Actually, this is another money decision. I realized at that point I wasn’t loving advertising, and I felt like I wanted to do something more purposeful, this is my twenty-five-year-old brain talking. So I got my master’s at the University of Houston. I was also still working at the same time, but because my husband was in the University of Texas hospital system, I basically went and got all this education for free. I remember working the system hard, getting all the documentation in line, figuring out how to get my tuition at a very, very reduced rate. We used to joke that I was going to school on coupons, like where’s the coupon for the week.

At the same time, I was tutoring for standardized tests, and this is a really interesting money story. It was a very lucrative hourly wage. I got asked, on a weekly basis, to fly in a little private plane from Houston to Fort Worth to tutor the children of the Bass family. I don’t know if you’re familiar with the Bass family. I would fly in this little Mesa jet once a week, early in the morning, rent a car when I got there, be there for the whole day in their home, and then fly back to Houston at night. I don’t think I had ever seen wealth like that. So thank you, Bass family, for exposing me to that, because that was a very formative experience.

Syama: Was your husband just like, who are you?

Andrea: I was like, who am I? So maybe I’m twenty-six or twenty-seven at this point doing this. It was a very interesting experience. That was just one of the families I tutored, the rest were in Houston, at my kitchen table in my apartment. I don’t even know how that all materialized, but it was really interesting because they had a gate, a guy at the gate, a chef, people in their home serving in all these different roles. That was something new for me to experience. I would just sit at the big dining room table tutoring all day.

Syama: What’s really interesting about that is early exposure to things lets you plant seeds, to go, hmm, is this for me, would I like this. When there’s no commitment to it, when it’s not necessarily yours, there’s an opportunity to try things on for size. Maybe I do like the chef component. It starts to scaffold something that wasn’t there before, which is pretty neat to see at a young age.

Andrea: I think so. I think it was neat too to see that they valued education, and they wanted their children to have this experience over the summer, and they were willing to figure out how to make it happen.

Syama: I don’t even know the sales and marketing strategy you must have implemented for this role.

Andrea: I worked for a company at the time, thank you, J Rush, if you’re listening, they’re still in existence, and that’s how it all came about.

Syama: So cool. So you finish university, smart young you figures out how to get it paid for, and figures out how to bring in an income. Then it’s time to relaunch yourself, right? You had one launch into advertising, and now it’s the relaunch. Where was your head at? How were you thinking about life, and what was important to you at that time?

Andrea: I’d say the relaunch was when I finished all the graduate work, and it was time for my husband to figure out where he’d get a job after residency. That search took us to Indianapolis, Indiana, which I had never been to before. We looked at opportunities from San Diego to Portland, Oregon, to Boston to Florida, all across the whole country, nothing was really off limits. We realized the best financial opportunity, honestly, was in the Midwest. Even though we had no family there and had never lived there, we took a chance and said yes to the opportunity. We’ve never left. We still live here twenty-six years later.

That was scary, moving somewhere knowing zero people. We were also in a different financial space, because now he was actually earning income, and so was I, though at a lower level than what I was making in Houston. We go to Indiana, where some things cost the same and some things cost a lot less. We buy a house, we buy another car, I start a new job with my degree in hand, and then I get pregnant. It was planned, but it was the next chapter, and a whole other set of decisions.

Syama: There’s an identity shift too, right? You move to a new place, and it’s who am I, who are these people, what’s my social capital. Maybe you have some built-in social capital because your husband’s a medical professional, so there’s some community there, but there’s still this need to reestablish who you are. It’s also a great opportunity, right, who am I now. Different places let you represent different parts of yourself. When you think about these bigger inflection points, it sounds like this move to Indiana was a big one, maybe the first signs of financial growth rather than just making it work. Were you guys thinking about investing? Was it, we’re doing the 401k matching, or thinking about the stock market, or real estate as a foundational investment? How did you start to think about ways to grow your money once you felt more stable?

Andrea: I think the first thing was that we said yes to any built-in opportunities that were part of our work situations. Before, we might have hesitated, do you really want them pulling that out of the paycheck every week. But now we were all in. If you’re going to match something, let’s go for it. That was very clear. I think at this point too, we pulled away from using our parents’ connections in the financial world to help manage our money. We made our own decisions about who we wanted involved in managing our money. Up until that point it was kind of just whoever dad recommended, and we went with it. Now we wanted a clean slate there.

We also quickly had kids, so putting money away for them was a new endeavor. Around the same time, my brother, who’s in private equity, started giving us opportunities as friends and family investing in some of his funds, which wasn’t your traditional stocks and bonds, it had more risk to it. So did we want to do that? There were a lot of questions, and I think we answered them mostly with let’s go for it, but maybe out of naivete more than anything. It probably wasn’t as calculated as it should have been.

Syama: But you were being yeah.

Andrea: Yeah. I think too, when you make a move into a new community, you realize you have to ask for things, and that connections and relationships are so important. I learned so much from the other spouses, my husband’s partners’ spouses, who were a lot older than I was. I would call them and ask questions about things I didn’t know, especially about what was available in our community, since I hadn’t grown up there and had never lived there before. I asked a lot of questions, and I think I grew a lot in that time personally, in my confidence, and in not feeling dumb to ask questions.

I’ll also say this is actually kind of funny, and funny not funny. We realized that the medical benefits did not cover pregnancy. So I was like, hello, we just assumed that would be part of this. Can we put that in there as a benefit? And we got it. We got it. But we had to ask for this stuff. It seems crazy that I had to ask for that, but that’s just an example.

Syama: That’s a powerful ask, and it’s something that sets a precedent, right? All it takes is one person to show some self-awareness and self-advocacy, and that’s how movements and things shift.

Andrea: Right, a hundred percent. The female spouse of one of my husband’s partners said, I knew you guys were coming, and you were a young couple, everybody else was older, and I pretty much assumed that at some point you’d want to have children. So when that occurred, I kind of said to these guys in the group, I told you so, and don’t ever think about not having that as part of your benefit package again. These are just little things, but they’re stepping stones.

Syama: And again, back to self-advocacy, feeling like you have the power to shape your own life, to push boundaries, to be the first. When did you start thinking about this next level of self-expression, becoming your own business owner? That’s not easy, it’s certainly terrifying. I tell people, you want to meet God, go start a company. What were some of the conversations you had to have with yourself, and then also as a family, to decide, all right, this is something we want to take on, that I want to take on? How eyes wide open did you go into that phase?

Andrea: So I dipped my toe in a little bit. My first venture into owning my own business was really just being an independent contractor for a larger corporate organization, a 1099. I didn’t have any benefits, I only made as much as I made based on performance. I saw that almost more as a convenience than anything else, because if I didn’t want to work, I didn’t have to. It was all performance based. That was a decision made a little bit out of fear too, because I felt like if I locked myself into some larger corporate role, and I’d been working in a hospital before that, I wouldn’t have the flexibility our family wanted me to have, since my husband had zero flexibility. Someone had to be the flexible parent, and this 1099 thing gave me the flexible parent card.

Through that experience, though, I became a little disenchanted. Yes, it was performance based, but there were a lot of handcuffs. There were things I thought might create more financial gain for myself that I simply couldn’t do. There were a lot of rules, you had to play by them. I didn’t like the rules, Syama. At some point I said, if I come up with one more big idea that they say is great, but I can’t act on it, I’m going to quit. And that’s what I did. Eventually I just quit, and I didn’t know what was next.

That was the point where I hired my very first coach. We were in a conference room with a big whiteboard, and she said to me, why did you stay there so long, what was it? Because you’re telling me a lot of things you weren’t happy about in that role, but what did make you happy? So I started explaining the things I actually did like about it, and through that conversation she said, I think you really need to just start your own business doing what you want to do. I resisted, because I felt like there wasn’t security in that, and it felt like a lot of work. Joke’s on me, because there was no security in the other thing either. But it felt less secure, it felt like a lot of betting on myself. Now I always say, if you’re not going to bet on yourself, how can you expect anyone else to bet on you? But at that point my brain wasn’t there yet. We took the risk anyway, and I quit that 1099 thing and started my own business. I was in my low to mid forties at that point.

Syama: And you coach. How did you find, I feel like admitting you need help isn’t easy for any human, how did you admit you needed help?

Andrea: Well, that was through, I kind of put out an SOS. I said, at this point I’m just open for conversations, I don’t know what’s next for me, I want to learn from other women, what are you doing, how are you using your skills, what’s going on. I felt like a professional coffee-date person for a little while. There were two people in particular who said, have you ever considered working with a coach to unpack some of this. And I said, hmm, no, not really, I didn’t really know what that meant. But I got referred to someone and said okay. That felt like a risk too, because of what might be revealed, and what I was getting myself into in terms of cost. But it turned out to be the best thing, and that’s kind of what spurred me to start my own business.

As a 1099, I was kind of my own business at that point too, but this was different, I was still sort of under a corporate umbrella. What I’ve been doing for the last ten years is truly just my own. I have people who work for me now. But I didn’t know where it was going to go at the time. What’s interesting now is that I’m working on what I’ll call a fundamental question, what does it actually mean to build something that exists beyond me? In the beginning it was, let’s build something that is my own. Now I’m asking what it means to build something that exists beyond me. That’s kind of the stage I’m in.

Syama: Those are big questions. You were beginning to say something earlier about the time it took for you to actually make the move, the time between the idea and the leap. Based on how you just scrunched your nose, I’d say it was crunchy. Tell me about that self-knowing, and then the move to actually do it. How did you prepare yourself, financially, in terms of a budget?

Andrea: So I tested the waters a little bit. I had a coaching business already at that point, and I said, I don’t know if I want to do this, I’m going to go work for someone else. That was my pledge to myself, and I got this advice that I still give to this day: set a time frame. I said, I’m going to give myself three months. I’m going to work for this other entity as a coach for three months and see if I like it, see if I like what having your own practice is really all about. During that time I also got officially certified, and I realized I’d actually been doing coaching in that 1099 role for ten years, it just was never called that, which is the irony of the whole thing.

By week eight, I remember thinking, I really like this, I like this type of work, but I don’t like working for the person I’m working for, and I don’t like the actual clientele I’m working with, I liked the clientele I had prior, in that 1099 role. So I wasn’t even going to finish my twelve weeks, I was going to get out of it. That was around April 1st, and I said, by June 15th, I want to have my own first client. I gave myself, whatever that was, seventy-five days.

I got a new credit card, in my own name, one of those zero-interest-for-twelve-months cards, which I’d never had before, because I’m someone who pays off all my credit cards every month. I said to myself, I am not paying one ounce of interest on this, I will make all this money back before I have to pay any interest. So let’s use this carry-a-balance, zero-interest thing, but once that interest kicks in, I’m not paying any of it. I’m going to have it all paid off. And that is what happened.

What’s interesting too, financially, is that I did not discuss this with my family. I just did it. They knew I was starting my own business, so I guess joke’s on them, what did they think, how did they think I was funding this? But the credit card thing, I just decided, this is how we’re going to do this. I needed capital, and I didn’t ask other people for it, I just used the credit card, and it was motivation too, to pay it all off before the interest kicked in, so that really lit a fire under me. I could have gone and asked for capital at that point, but I didn’t, and in retrospect that might have been a mistake. But that’s how I did it.

Syama: I love that. There’s a point in business where I feel like, and I especially see this with women, we keep investing every dollar we make back into the business, and then there’s a point where it’s appropriate to start paying yourself, and it’s important to start building your life and thinking about taking distributions. In the beginning it’s like the money goes straight back to you, then you start to invest and hire, and it’s a funny shape that happens as you’re building something. Everyone tells you to keep your personal and business finances separate, but when you’re the business owner trying to make everything happen, that’s very difficult. So when was the inflection point, after you started to hire people, where you felt like you could pull money back out of the business, or felt more stable and confident with the business model?

Andrea: This is a huge topic for anyone starting a business, paying yourself, and figuring out when that tipping point is. I think too many women especially wait too long to start paying themselves in a way that feels good. They pay themselves amounts that feel like seconds, whatever’s left over, we’ll call it, versus recognizing, no, I am a primary resource in this business, and if there wasn’t me, it wouldn’t be happening, and I need to be compensated for it. I was pretty good early on about paying myself something, but it probably wasn’t until year three that I got really deliberate about paying myself a salary and then taking regular distributions, not just waiting until there was enough.

There were two reasons for that. One, it didn’t feel good to be like the least paid employee of my own business, and I became bitter about it. Two, I really looked at what I wanted to pay myself and contribute to our family, that was a strategic decision, these are the expenses I want to be covering, and I also want to be investing, which is a whole other thing, what am I taking from the business to go invest in things outside the business, other personal investments. I had to get really good at understanding cash flow in the business, projecting, and it took my financial acumen to another level. If you don’t have that, or you’re not willing to ask and learn about it, you’re missing out on opportunity. That’s part of why people sometimes think, I don’t know how much longer I can do this, because you’re basically the least expensive but most overworked employee in the business. That’s not good, it’s not sustainable.

Syama: No, it’s not. You’re in the business of women and their businesses, so you get to both support and help, see how other people are strategically growing, be an active part of their success, and undoubtedly learn at the same time for yourself. What a wonderful mirror, to see how you’re evolving and changing as you’re supporting others who are evolving and changing. Can you share a few of the inflection points, things you’ve learned as a result of working with so many powerful women and their businesses? What are some of the themes or insights you’ve noticed in these high-performing women that you think are valuable?

Andrea: Great question. A couple things come to mind. Number one, family-owned businesses are very tricky, for lots of reasons, but finances seem messier in those businesses, feelings and finances become very intertwined. So anyone considering a family-owned business, just think about that. I’ve observed it numerous times, and it’s rare, I’ll go as far as to say almost never, that things are clean decisions. Our feelings are intertwined in all of our decisions, but extra so in a family-owned business.

But on a more positive note, when a woman I’ve worked with has taken what I’d call a risk, investing in properties, owning properties connected to their business, purchasing or acquiring another business and merging it into theirs, mergers and acquisitions, those are risky and scary in the moment, but most of the time it brings a lot of joy in the long run. It may bring some headaches, but the opportunities that come once those risks have been taken would never have happened if they hadn’t taken the risk. I always say, what’s the worst that can happen? Everybody goes to, well, I lose all my money. Okay, but you could gain so much too, and you’d figure it out. I trust that you would figure it out if it got to a place where you felt financially strapped. Some little light bulb would go off in your head and you’d figure it out.

I think taking those risks is really important, and not waiting until all your ducks are lined up in a row, as someone said to me recently. There’s a theory, Colin Powell had this 40/70 rule. I don’t know if you’ve heard of it. Colin Powell said you need to make a decision when you have between forty and seventy percent of the information you think you need. If you wait until you have all your ducks lined up, or over seventy percent of the information you think would be great to have, it’s too late. And if you make a decision without having at least forty percent, then maybe you’re making it prematurely. But between forty and seventy is when the best decisions get made. I kind of go by that. I can think of a few times in my own life where it was, okay, we know enough to know, and if it doesn’t work out, we’ll figure it out. A lot of the most successful women I see fall into that forty-seventy range.

Syama: That is really powerful, that will definitely land with me, I’ll remember that, Andrea. So now you’re thinking about the bigger picture, what does all of this mean, what’s next, how does it turn into, let’s call it legacy. One of my favorite ways to wrap up our conversations is around the future, and how you think about a life well lived. Assuming we’ll all be living much longer than we likely anticipated, let’s put you at a nice young age of a hundred and ten, you’ve got a lot more living to do, girlfriend, there’s a lot more ahead of you. As you put yourself into your future self and look backwards onto the body of work that is your life, what comes to you? What is this body of work that you’ve been building?

Andrea: I feel like what I’ve been building, at the deepest, most theoretical level, is the idea that identity really precedes strategy. What I want my legacy to be is for women to understand, or learn, or explore, that being drives feeling, and feeling drives knowing, which drives doing. You don’t get clarity by gathering more information. You get clarity by deciding who you are first. I’ve been applying that to my own business, and I’ve been excited to see what this brand of She Thinks Big can bring to others. If more women can think bigger about what’s possible, and who they need to be in order to become what they want to become, I think I will have done a good job.

As I evolve into this next phase, I mean, a hundred and ten is a while away, so who am I going to be in the next fifty years or whatever? I don’t know. But I think I can be the next best version of myself. I’m not sure what that will entail, but it’s exciting to think about. I get energized by that thought.

Syama: That’s a powerful thought. Okay, last two questions. We’ve talked a lot about money from the lens of savings and investing and opportunities and strategizing and what you pay yourself, the more technical, operational side of money. But we both know money can also provide us a tremendous amount of joy and can be really fun and fabulous. So tell me, what has been one of your most favorite recent ways of spending your money?

Andrea: Well, very recently we spent money to go on a trip, myself, my husband, and my two twenty-somethings. We went to Jackson, Wyoming, we’d never been. We stayed in a fabulous home there for the week, did private guides, went through the Grand Tetons, a real adventure. We hadn’t traveled like that in a while, and it didn’t involve visiting any family. We have no family here in Indianapolis, so a lot of our travel is attached to some family function or visit, but this one wasn’t. I just decided, we’re going to do this, we’re not holding back. All the groceries were delivered and put away before we got there, we had someone come one night and make us a meal, I had it all planned out. It wasn’t the most extravagant trip in the world, but it was worth it to get everybody together. That happened a couple weeks ago, and I’m glad, because now my kids are off in the world, onto their next eras of their jobs and lives.

Syama: I love that. And my final question, Andrea, the women who listen to the show love to rally around the women who are on the show. What is it that you’re calling in right now? What do you need, what do you want, how can we support you?

Andrea: I am calling in more opportunities to share what big thinking is all about, whether that’s getting in front of an audience or being on another podcast, I’d love those opportunities or introductions. I’m also welcoming more people into my world. We were talking about this before we pressed record, aggregating all of the content I’ve created over the last ten years or so and putting it out there in a new way, and soon I’ll be welcoming people to dive in.

Syama: Andrea Liebross, the woman, the myth, in the flesh. You are brilliant, heart-centered, curious. You are my kind of woman. I am so honored to be in community with you, to have you share so openly and vulnerably your life story, and to really see what thinking big can do for all of us. Today has certainly been inspiring for me. Thank you so much for being here.

Andrea: Thank you for having me, and for trusting me in the conversation.

Syama: Thank you for listening. This is the conversation we come back to every single week. Real women, real wealth, and what becomes possible when we stop being silent about money. If today’s episode moved you, don’t let it stop here. Wealth Catalyst is where women go to take it further. Our Freedom Tour salons are gathering women in 32 cities this year, intimate evenings in homes and private spaces where women talk honestly about money, risk, and what they’re building.

And if you’re ready to go even bigger, join us at the Wealth Catalyst Summit, a full-day event in San Francisco this October. Find your city and claim your seat at wealthcatalyst.com. We’ll see you there.