212 | Carving a Path to Financial Independence Through Self-Love with Jenna Banks

Jenna Banks



Welcome to episode 212 of Love, your Money! In this episode, I’m talking with Jenna Banks – an entrepreneur, speaker and the author of “I Love Me More: How to Find Happiness & Success Through Self-Love.”


After climbing to a cushy 6-figure corporate job, Jenna decided it was time to listen to her inner calling. She ditched the cubicle in favor of entrepreneurship, and started a product marketing business that she sold in 2019 for $500K.


Today, you’ll hear Jenna talk about tapping into your internal self to hear, understand and act upon your calling. You’ll also learn about scaling and selling a business, the dangers of perfectionism and the transformational power of independent wealth for women.

Here’s what you’ll find out in this week’s episode of Love, your Money:

  • Leaving a 6-figure job for entrepreneurship
  • Scaling a business and decreasing your hours
  • Why perfectionism might be holding you back
  • How Jenna sold her business for $500K
  • Staying open to the universe’s opportunities
  • Intergenerational trauma challenges women face
  • The power of money for women
  • Internal self-love vs. external validation 

Inspiring Quotes

“Money gives us independence, it gives us freedom, it gives us ability to think creatively without the guilt and the shame and the self-judgments and all of that stuff. We have to learn how to shed all of that and embrace money because with money, we can do so much more to impact the world for good.”

“What the world would look like if it were running perfectly for you and your business. Then work backwards from there.”

“What transformed my business was learning that 80% is good enough.”

“If you really believe what’s meant for me will be, then you don’t worry about the no’s. You don’t worry about the rejections. You don’t worry about the things that don’t go the way you would like them to go. It’s just not meant for you. That’s all.”

Enjoy the Show?​

Hilary Hendershott: Welcome back to Love, your Money. I’m Hilary Hendershott, your host. And with me today is the lovely Jenna Banks. Welcome to the show, Jenna.


Jenna Banks: Oh, thank you so much. Happy to be here.


Hilary Hendershott: I met Jenna, she actually interviewed me for her show and something she said made me think to myself, I need to have this woman on the show. So, let me just give you her media bio, but then I’m going to hopefully get her to tell just a really inspirational money story. She is a speaker, award-winning author, and entrepreneur whose work has been featured in tons of media outlets, including Forbes, ABC, and NBC. In 2012, she founded a home-based marketing products business, which she sold in 2019 for a half million dollars. So, can’t wait to dig in about that.


Today, she helps women live to their fullest potential through writing and speaking engagements. She hosts The Jenna Banks Show, which is streamed on binge networks, TV, Roku, Apple TV, Google Play, and Amazon Fire TV. So, she’s in all of the places. I’m excited to talk more. Welcome.


Jenna Banks: Thank you so much.


Hilary Hendershott: So, when we met, so tell me about this home marketing products business, or if I said those words in the wrong order, tell me how that all got started.


Jenna Banks: Yeah, well, I decided to quit my cushy corporate job and start working for myself. And I just dove in and I really didn’t have a plan. It was unexpected, but I just wasn’t happy. I was making a nice six-figure income at that job, had been doing it for a while, and just was bored and also not challenged. And it just was time for me to go. I knew there was something else in store for me.


So, I just started the journey playing around and started learning about content marketing at the time. So, the business, just to be clear, was marketing products, so think promo items, like any kind of three-dimensional product with a logo. And I had a history in that business in the past, but I hadn’t been in it for many years. So, I thought, “Why don’t I take what I’ve learned from this last company about the Internet, selling products online, SEO, all that stuff, and then learn about content marketing and see how I could do it differently than I knew about the business in the past?”


In the past, the business had been more about selling in person, right? It’s all about your relationships, who you knew, someone in marketing, great, you probably get their business. Well, I wanted to do it different. I wanted to cast a wide net, a worldwide net, and do it online. And so, I just started learning about content marketing, and business started coming in. And suddenly, I started getting busy. And you tell the story about how I sold it in 2019 for half a million dollars. The journey from starting a business in your home on the Internet to selling it for half a million dollars was a whole learning experience that I did not have any kind of master’s degree to figure out, so yeah.


Hilary Hendershott: Well, one of the things you said to me was that you found that once you decided to turn things around in the business, maybe it was headed kind of downhill or maybe you weren’t profitable and you kind of had an aha moment and said, “No, I need to turn the dials until this thing is actually making money.” Can you talk a little bit about that? How did that happen?


Jenna Banks: Yeah, okay. So, my pain point was I really wanted to scale. I realized that, all right, the business is doing great now. I’m working 12-hour days. I can’t take a real vacation. A couple of years had gone by, and I’m like, “This is not going to work. This is not what I signed up for. So, how do I scale?” Well, the profit margins were what they were.


And then doing the math, I’m thinking, “How am I going to hire a workforce here in the United States with workman’s comp and insurance, 401(k), and all that? How am I going to afford that?” So, I didn’t think it was doable. So, then I just started getting creative. And this is where my MacGyver skills come in. I’m starting to write a talk about thinking like MacGyver.


Hilary Hendershott: Be careful. I think some of our listeners may not know who MacGyver is.


Jenna Banks: All right. I’ll tell you who MacGyver– I think they actually were shooting a new version of MacGyver here in Atlanta, if I’m not mistaken. It might have already come out. But MacGyver was a show, I think, back in the 70s or 80s, about this guy who basically, something was going to happen and the world was going to explode and he needed to save humanity and he did it all with gum and the paperclips in his pocket.


Hilary Hendershott: Yeah. Kitty litter. He always had kitty litter.


Jenna Banks: Yeah. Duct tape, Swiss Army knife. Yeah, somehow, he could stop the bomb with this paperclip.


Hilary Hendershott: Women everywhere just found it completely hot.


Jenna Banks: Exactly. Well, I’ve learned how to use MacGyver skills, and so, I think, “What can I do to make this work?” And it’s about thinking outside the box. This is what I know. It’s hire people in the US, but is that really the way to solve this problem? So, I started thinking differently and I was like, “Well, how does Microsoft do it? How does the virtual phone company I know that I’m using do it? Because I know their workforce is in the Philippines, how are they doing it?”


So, I just started to work backwards from there. So, that’s my way of approaching my MacGyver skills is envision your best-case scenario. What would the world look like if it were running perfectly for you, your business, if it were running perfectly, and then work backwards from there? And so, I thought, “Okay, I want to have a team overseas. That’s a fifth of the cost. How do I make that happen?”


And so, I ended up going through trial and error, figuring out how to hire a workforce over there. It cut my overhead by– if I were to hire the same team members here, it would have cost me five times more. That’s what really led me to selling the company for half a million dollars because I learned how to make the company work with very low overhead.


And so, my issue was, remember when we started out, I was working 12-hour days and no vacations, right? I said, I don’t want to do that anymore. I got to the point where I was working two-hour days and made the company sellable. I devised it in a way that I could walk away. And then I will add one more thing to that, is your audience mostly women, Hilary?


Hilary Hendershott: Mostly women, yes.


Jenna Banks: That’s great, okay, because this was an issue that I was encountering, which was perfectionism. And your listeners might relate to this. A lot of us…


Hilary Hendershott: That’s what we do.


Jenna Banks: Tend to be perfectionists and we think that that is an attribute. I did. I thought my perfectionism was what was making the business work, was what was making the client stick with me, was what was making all the income come in because I did it so perfectly.


Come to find out after being so burnt out one day, I turn on an episode of Shark Tank. I love that show. And Barbara Corcoran is talking to an entrepreneur and telling her why she’s not going to invest. She says, “I think your product is great, but you worry too much about doing everything perfectly,” she says. I used to do the same thing and it was killing me.


And what transformed my business was learning that 80% is good enough, done is done. You have to go, “You know what? It’s good enough. I need to move on.” And that’s the way you’re going to be able to scale. And she says, “You can’t let go of perfectionism. Therefore, I can’t invest in you.” And that really hit me like a ton of bricks. I was like…


Hilary Hendershott: I can tell, yeah. The universe is speaking.


Jenna Banks: “What?” Yeah, I never heard anything like that before. So, I said, “Okay, I’m going to try this. Something has to give. This perfectionism isn’t working for me. I’m not able to scale.” So, at this point, I had already started hiring employees in the Philippines. But guess what? My perfectionism was causing me to lose them after three, four, or five months of training, a lot of time and energy. And I was expecting them to work at the same perfectionist level as I was because that’s what we do. And you burn through employees that way. So, that was the next thing I had to learn was to let go of that.


Once I was not so hard on myself, when I learned that and implemented that 80% is good enough rule, I could then be forgiving with my workforce too. Okay, so that email wasn’t perfect. Okay, so they lagged behind on this, but they’re doing all these other things, great. It’s 80%, and we’re doing great. And no one’s going to hold it against them if I don’t. So, we didn’t lose clients and we were able to scale. So, that really, those two things really allowed me to scale.


Hilary Hendershott: And then, when did you start thinking about selling it? Or was that always your idea from the beginning?


Jenna Banks: No. Well, I was building it to eventually sell, but from what I have learned about selling a business much later on, I realized from what I had been told, which was wrong, I had been told that it’s like some percentage of your EBITDA. And it was like…


Hilary Hendershott: That phrase, EBITDA, it’s so funny, people throw it around. It doesn’t mean anything for small businesses. It’s like– but everyone says it. Go ahead. Thank you.


Jenna Banks: Yeah, yeah. And so, I thought, “My God, all the time and energy that I put into it, and now, I’ve made this company to where it’s working for me. I make a good income and I don’t have to work that many hours. I’m not going to get what it’s worth to me, so why even sell it?” But then, I got this flier in the mail, and it was a free seminar on how to sell your business. Okay.


Now, I usually throw all that junk mail away, but I was like, “Man, this is like a power broker here in the city I live. It’s free. Why not take a couple of hours out of my day and go?” So, I did. Come to find out they had a whole different technique for selling. It didn’t have anything to do with some multiple of profit. It was based on selling not to competitors, but selling to synergistic businesses who have a similar client base, who can monetize not only the clients that your company has and integrate the two together, but cross-sell your company’s products with their current client base. So, it’s an instant win-win for both businesses. So, you sell based on the future income and also the trajectory of the income.


Hilary Hendershott: You’re essentially selling them a customer base.


Jenna Banks: That’s right. A whole different way to think about selling. So, I thought, “Huh, this could be interesting.” All right. So, the reason why it was on my mind is I’d gotten the opportunity to speak in front of an audience that I’ve never done before. I was freaked out about speaking on a stage, and this was at the L.A. Convention Center, and I took it. I said, “You know what? I’m going to face that fear. I’m just going to go for it.”


That turned out to be one of the best decisions I made because I got on stage. And while it wasn’t a perfect presentation, I really enjoyed seeing people light up and motivating them and inducing some kind of action where they came to my booth afterwards and they listened to every word I said and they were making a transformation in their business because of what I was telling them about how promotional products could work for them. And I thought, “Wow, if I could do this with marketing products, I could maybe do this on a bigger scale.” And I really want to do more in my life. I want to touch people on a deeper level. I want to have an impact. I want to live in my purpose. And promotional merchandise is probably not it.


So, I just wanted to be stretched again in new ways. And I’ve been doing it for about seven years now. It was a long time, so I thought, “Okay, universe, if I put my business on the market and if I put a price tag of a half a million dollars on it,” which is what I wanted, “I will sell it and I will take this as a sign that it is time for me to move on to this next phase of my life and pursue that. If you give it to me, I will do that.” And 30 days later, I had an offer on my business for half a million dollars.


Hilary Hendershott: I feel like your life is the book by Gabby Bernstein, The Universe Has Your Back. Do you know this book?


Jenna Banks: Yes, I do.


Hilary Hendershott: And I actually am shocked that I was able to come up with her name. I think about the book title semi-frequently, but it’s somewhat remarkable that I actually thought of her name because I have that disease where I can never remember people’s names.


Jenna Banks: I’m the same, I’m the same.


Hilary Hendershott: But I mean, and if we could tease apart, because most of the people listening, they don’t have a promotional products business, but there’s some of these things that you did. I mean, for example, we’re all bombarded with messages. We’ve all watched Shark Tank, but it hasn’t changed our life, right? That poor woman who had to get on Shark Tank and hear that message from Barbara Corcoran, I mean, just imagine the cost of that in her life. She has to sit with that forever. I was rejected for being a perfectionist. And I’ll never have that opportunity again. They’re not letting her back on Shark Tank, right? But you didn’t even have…


Jenna Banks: But she learned a valuable lesson.


Hilary Hendershott: And you did, too.


Jenna Banks: And I did, too. That’s right.


Hilary Hendershott: Yeah. And this one flier that came to your house where, with the opportunity to go learn from a business broker, I mean, how would you describe your, I guess, courage, gumption? Where does that come from? What is the mindset that leads to that?


Jenna Banks: It is being open to opportunities. That’s what my life is all about. Just staying open to opportunities because that’s how you work with the universe. I am 100% in the flow of the universe. We can be in resistance, right? We can be in resistance. We can have a mindset of this is the way things should be, and then you will be resistant to every opportunity the universe brings your way.


But if you put an intention out there and you say, “You know, I think I’d like to go here,” and then the universe starts bringing things your way, okay, and then it sends opportunities your way, you just have to notice them. And that’s how it works. And so, that is being in the flow. And so, I just stay in a flow state and that’s what works for me. And it always has.


If I look back on my life since I was a child, and in my book, I write about how I did not have it easy, it was a very rough childhood. And I came from a very– you’d be surprised to know where I am today as opposed to where I came from. But I look back and I always see that I’ve always been taken care of. No matter how bad things were, we were always taken care of. There’s always something looking out for you in your best interest. And it’s all here to serve us. We’re here to learn. We’re here to learn and blossom into our full potential. And I really take that literally. That’s how I try to live my life. How can I make the most out of this life?


And we can get comfortable and we can say, “Okay, I’m working for this retirement. I’m on track.” That’s what you help people with, Hilary. And I love that you help women live to their full potential financially. But I could just sit back on that and say, “Okay, great. I sold my company for half a million dollars. I’ve invested in these rental properties. I could take that money and stick it in the bank. And you could help me with a plan to retire comfortably. But is that why I’m here?”


Hilary Hendershott: No. It’s clear you’re living your calling. And so, I think, many of the conversations I have with women, and then you have a lot of conversations with women as well. So, I’m interested in your experience. Many women are afraid to ask for what they actually want, to sort of demand to be paid, to raise their prices, right? And I see you over here. And you did share with me. You never had a full-time employee. So, you don’t have someone who’s right there with you, someone to whom you’re accountable. You’ve always been the one that people are accountable to, right?


So, are there days when you wake up and you think, I’m terrified to make this phone call and you find you avoid it for a week or a month? Or are you just completely self-determined? What can my listeners take from– I’m imagining there’s a thousand times you’ve taken an action and you thought, I didn’t get the result that I wanted, but who cares? I’m going to do it again. Tell me about that mindset in you.


And I know you’ve already said, you’re out to create a narrative with the universe where you’re living your one precious life. But in that moment, when you were pressing send on that email or picking up the phone to make that terrifying call, what is the voice that’s guiding you?


Jenna Banks: I mean, what’s the worst that could happen? They say no, right? I mean, truly, and I do a lot of work with women. That is where I’m called to work and to serve. We have a lot of limiting beliefs, a lot of self-doubt, a lot of imposter syndrome. And I was talking to this amazing woman on my show yesterday, Nina Simons. She is the co-founder of an amazing organization called Bioneers. They’re affecting the world and they’re making massive change.


She wrote this really incredible book for women leaders. And she talks about how– she mentioned something in her book and we talked about it on my episode yesterday about how something she watched changed her life forever. It was an old documentary called The Burning Times. I’ve yet to watch it, but I’m going to. And it overviews how we were, as women, burned at the stake for a long time, being accused of being witches and whatever. And this was across massive swaths of land.


And the impact, if you look and if you know anything about epigenetics, or if you don’t, I’ll give you just a brief summary of that, what epigenetics is, and I’m not a scientist, so I’m probably going to butcher this. But in essence, what it means is these traumas are passed down through us genetically.


Hilary Hendershott: The idea of intergenerational traumas, yeah.


Jenna Banks: Yeah. So, it lives in ourselves, it lives in our genes. And I’m sure there’s some evolutionary reason for that, and perhaps, it serves us in some good ways, but it also serves us in some bad ways. And so, as a result, as women, we have this trauma that sits in us still to this day that makes us believe these things, like we’re not worthy, who am I to do this? We doubt ourselves.


And also, there’s another amazing book called The Genius of Women by Janice Kaplan, where she talks about we haven’t had these women geniuses to look at as role models. Not that we weren’t it, we just weren’t given credit when we were doing these genius things because we’ve been in a patriarchy for so long. And so, we doubt ourselves, right? We think, “Oh, my God, what if and what if I fail?”


And again, here we go into that perfectionism. It has to. If it’s not a yes, then it’s I failed in some way. And we have to get over that and just go, you know what? Okay, I might not get a yes this time, but again, being in that flow state with the universe, every no kind of redirects you to the place where you are supposed to go to get that yes. If you really believe what’s meant for me will be, then you don’t worry about the nos. You don’t worry about the rejections. You don’t worry about the things that don’t go the way you would like them to go. It’s just not meant for you. That’s all.


Hilary Hendershott: What you just said reminds me of something that I’ve said. I think I did a podcast episode about it a couple of years ago. This idea that when you hate on other women for being successful, oh, that’s too much, I would never want to be that successful. Oh, she’s an executive. She’s probably not a good mom, right? These are some of the things I hear said or thought because I spend so much time talking to women and it’s not often the women who are talking to me, but these women have heard from their so-called friends. And I said, “This is us essentially foisting the patriarchy on each other.” We’ve embodied this voice, that’s like women shouldn’t be too big, shouldn’t be too powerful, shouldn’t receive too much, definitely shouldn’t want to be rich, right? And so, that’s why I call finance the last frontier of feminism. It’s like we’re taking ground everywhere else. It has to be okay for us to be multimillionaires.


Jenna Banks: Can we just talk about that for a minute, Hilary?


Hilary Hendershott: Yes. Interview me.


Jenna Banks: Because it is super important. Okay. No, but honestly, I mean, this is what you do to help empower women. And I talk about this as well in my book, and I want to do more episodes about it on my show because it’s so important that we be in our power, and having money is power, is freedom. In the patriarchy, we look to men to be the money earners and put all our energy into the men. And the men earn the money and they take care of the family and all of that.


But if we’re going to do what we’re meant to do in this world and have a feminine impact on the world, we need money to be able to do it. If I didn’t have the money from selling my business and having rental properties and being independent and having my own money where no one else, I wasn’t accountable to anyone else for how I spent that money, I wouldn’t be able to do what I’m doing now.


I’m getting on stage in a couple of months in front of 500 women leaders to talk about the power of self-love. I wouldn’t have been able to afford to do that if I hadn’t invested in myself like I had, if I hadn’t followed the flow of the universe. We haven’t had that kind of money as women to be able to do these things. And money gives us independence, it gives us freedom, it gives us ability to think creatively without the guilt and the shame and the self-judgments and all of that stuff. We have to learn how to shed all of that and embrace money because with money, we can do so much more to impact the world for good. And that is a different way of thinking about money.


Hilary Hendershott: You’re speaking my language. You and I, we’re telling the same message. I look around and I hear women say, and I talk about it a lot, “I don’t need to be rich. I don’t need to be a millionaire.” I sent out an email a couple of months ago that said, the subject line was, “Yes, you actually do need to be a millionaire,” because it’s like, first of all, logistically, financially speaking, a million dollars is really not enough to retire in most places in this country, so yes, you do need to be a millionaire, but also, why not, right?


If we’re going to emancipate and free ourselves from the remaining amounts of misogyny and patriarchy we do suffer from, we need to be self-determined. And that I feel like, and I do want to talk about your current messaging and what you’re doing now, but I mean, when I hear your story, it just screams self-determined to me. I just see you as this force of, “No, I’m going to do it. I’m going to get up on time. I’m going to do the things. I’m going to take care of myself. I’m going to build a business a couple of times.” I’m just impressed with your embodied energy. You must have a lot of energy to keep doing this.


Jenna Banks: A lot of energy. I’m so glad you bring this up, Hilary, because I do want to talk about that. It will transition to what I do now. It is self-love, talking about self-love and the power of self-love. There’s this really amazing book, and the reason why I keep referring to books is because these are books that have impacted my life in big ways. There’s this book called The Seven Spiritual Laws of Success. I probably read it 40 to 50 times.


If you’ve never gotten it, go on to Amazon right now, everybody, and get a copy. It’s tiny. It’s seven simple laws of the way the universe works, written by Deepak Chopra. And it is quite profound, super deep, very simply explained, but it’s a lot to absorb, and you can read it in an hour or two. So, it’s really beautifully written.


One of the things he says really hit me hard was that we look externally for reference about who we are, whether being liked. Are you validating me? If so, then that’s okay for me. What happens is when we look externally for approval, we end up changing who we are. We’re actually not authentic. We are not even really who we really are because we’re always looking outside of ourselves for answers. Like, do you like me? Oh, you don’t like what I’m doing. You like my hair better blonde? You like it better short? Oh, you don’t like that. Oh, you like my boobs big? Like, what– we change ourselves based on what we see other people liking, and then we just become a version of ourselves that we don’t even know. We don’t even know.


So, switching that to being an internally referenced, just reference your internal self. It takes years of practice. It took me years of work to learn to do it. And I still catch myself, finding myself, going, “Oh, do they like what I’m saying? Maybe I should change my messaging a little and water it down.” But that’s not being true to me. So, when you look inside and say, “Well, what do I like? What do I want to do? What’s calling me? Even if nobody relates, what is it that’s true to me?”


And then when you can start to go and start to say, “You know what? Yeah, I’m going to leave this corporate job that’s paying me six figures because I feel called to do something else. Who cares if my grandmother thinks I’m crazy? And now, she’s going to go, unfortunately, into a deep depression because I’ve made a financial decision for myself.” See, that’s another example of looking externally. We look externally with our family, and then they guilt trip us, right?


Or my dad put all of his time and money into me to send me to this school. I don’t want to let him down. We have all of these obligations and things that make us look outside of ourselves and we just don’t question it. We just do it, unquestionably.


But unfortunately, what happens is we learn to deny who we really are. And that’s what’s missing today, I believe. If we can just go inside and learn to just reference ourselves and say, “I’m sorry, mom and dad, I’m sorry, grandma, you’re going to have to go through your own adjustment, but this is me being me. This is how I’m going to be happy.” And that’s how I have so much energy to do these things because I have my energy back.


Hilary Hendershott: So, to the extent you’ve managed to become self-referenced, that is I feel like a whole course on living. So, that is amazing to hear. Thank you for talking– we’ll mention the book in a link below show notes for today’s episode.


As a segue to that, your current website is full of messaging about both self-love and power. So, talk a little bit about how you’re spreading the word and how you’re making money. What are you doing in the world today?


Jenna Banks: Today, I am an author. This is my book, I Love Me More.


Hilary Hendershott: I Love Me More, nice.


Jenna Banks: And I wrote that during COVID and it came out last year. So, since then, what I’ve been doing is focused on what I promised the universe I would do, which is get out there and speak, get on stages. And so, I’m doing a lot of speech preparation right now for my talks. Yeah, and that’s led me into doing moderating and MC’ing, and slowly but surely, that is becoming my source of income, but it’s taken a lot of investment into myself to get there. But that is where I feel called to go and grow. So, I talk a lot about self-love.


My website, I would highly recommend if you’re interested in learning more about all the details of self-love, it’s very nuanced and a lot deeper than most of us think about. It’s not just bubble bath. It’s a lot of deep work.


Hilary Hendershott: No.


Jenna Banks: Check out either my book, or I’ve got a free email series called Love Notes to Myself. You can sign up right on my website, totally free. I send it out a few times a week. And it just helps people learn all the nuances of self-love.


Hilary Hendershott: Amazing. Jenna, I feel like our meeting was so serendipitous. I’m so in awe of what you’ve done and what you’re doing. Congratulations on being– I just keep thinking of you as self-determined. I’m just like, Jenna is a force of power. So, definitely, we’ll put links to all the places to find you, including Love Notes to Myself, and your, of course, YouTube and video series, which is amazing.


Jenna Banks: Thank you.


Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.


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