Jennifer Bower, Fortuna Money

[00:00:00] Sanjay Parekh: Welcome to The Side Hustle to Small Business Podcast, powered by Hiscox. I'm your host, Sanjay Parekh. Throughout my career, I've had side hustles, some of which have turned into real businesses, but first and foremost, I'm a serial technology entrepreneur. In the creator space, we hear plenty of advice on how to hustle harder and why you can sleep when you're dead.

[00:00:21] On this show, we ask new questions in hopes of getting new answers. Questions like, how can small businesses work smarter? How do you achieve balance between work and family? How can we redefine success in our businesses so that we don't burn out after year three? Every week I sit down with business founders at various stages of their side hustle to small business journey.

[00:00:42] These entrepreneurs are pushing the envelope while keeping their values, keep listening for conversation context and camaraderie.

[00:00:55] Today's guest is Jen Bower, a mom of two, a veteran, a grad student, and the founder of Fortuna Money, a financial coaching service based in North Carolina. Jen, welcome to the show.

[00:01:06] Jennifer Bower: Thanks so much, Sanjay.

[00:01:08] Sanjay Parekh: So it's great having you on because I mean, at the root of almost everything that we do is money in terms of being an entrepreneur and startups and all of this kind of stuff. But before we start getting into all those weeds and that crazy stuff, give us a little bit about your background and what got you to where you are today.

[00:01:24] Jennifer Bower: I went to the Air Force Academy and became an intelligence officer, and when I graduated I went to training and learned how to make big, messy piles of information into decision useful recommendations.

[00:01:42] And it turns out that was a skill that I was able to carry with me throughout the rest of my professional life. I was five years active duty, three deployments to Iraq and then four years in the reserve, some of which I got to do in Japan, which was really fun. And then when we relocated to Charlotte, North Carolina, I started working for Bank of America in the financial crime investigation world.

[00:02:06] Which was really fun, really interesting. Not something I necessarily ever expected to get into, but one of my dear friends from my school days was working there and had her resume on her desk at the right time. So I got a really cool insider view of the banking system, and because I was mostly investigating fraud, I got to see a lot of what would go wrong with all of the consumer products that most of us are touching at any given moment. I was I, The hardest part of that job was that I wasn't able to do more to help people who were victims. They were usually coming to me and I was investigating their case well after the horse had gotten out and we were just trying to get that barn door closed. And I, I just, You know, always found myself thinking, wow, if only somebody could have talked to them and helped them when they were at the beginning of their journey before they, you know, built a financial house of cards or before they, you know, fell for a romance scam or something else.

[00:03:07] Right? And so for me, that seed was really planted and I got very passionate about personal finance. A little bit before we moved to North Carolina, my husband and I were newlyweds and he was the super saver and I was the super spender, which is not that unusual, right? There's two kinds of people in the world and they marry each other and and so, you know we had to work through some stuff and we found a playbook that really worked for us and we were able to you know, reconcile our different approaches and make a lot of progress on our financial goals. And so I found myself giving recommendations to friends and family and kind of helping them with my banker knowledge and my own personal experience, the things that I'd been able to put into place that had helped me be more intentional with my money and make more progress toward my goals.

[00:03:57] Fast forward. I left banking for a few years to go work for a tech startup that was doing some defense contracting work, returning kind of to my military supporting roots. And while I was there, the entrepreneurial bug kind of bit me. You know, you're in that startup environment, you're like, well, maybe I could do this. And I just, I knew I really wanted to be back in the space where I felt like I was. I was helping people, I was really making a difference. And I'd been, I'd kind of been searching for that space all along. And when I learned about financial coaching, I was like, well, that sounds kind of perfect. This is something, you know, I studied behavioral science in college, so you know, the behavior plus the finance, I'm like I think this is something that that I can do. And, you know, it's been about four years since I, you know, started practicing and three years since I've been doing this exclusively. And it's been a wonderful ride.

[00:04:54] Sanjay Parekh: Yeah. I gotta ask you, so you mentioned you touched on being in Japan. How long were you in Japan and where In Japan?

[00:05:01] Jennifer Bower: I was a little over a year in Japan. My husband was stationed there when we first got married, and so I got to move out and join him. And he was outside of Tokyo, I jokingly call it kind of Tokyo jersey because you're like, you know, not in like the thick of the city. Yeah. But yeah. Have you spent much time in Japan?

[00:05:22] Sanjay Parekh: So I lived in Japan in the mid nineties for about three months working as a part of my first job. And. People don't really understand that Tokyo is massive. I mean, it's like a two hour ride from the airport to the hotel I used to stay at. And it's all still within Tokyo, right? Yeah. And that's in the middle of the night with no traffic and it's still that far. It's just people don't really understand the massiveness of some of these places and just how much stuff there is. But okay let's talk about the business and kind of what you did. So you started this as a side hustle. You got that shine of entrepreneurship on you because you were at a startup.

[00:06:05] Was this the first time that you'd done anything entrepreneurial yourself or was there something when you were a kid or family or anything else like that?

[00:06:14] Jennifer Bower: Oh no. I joked for years that there was not an entrepreneurial bone in my body that I wish there was. because I would have, you know, fun ideas. But I'm like, yeah, but that's. You know I would never do that. And I, you know, come from a long line of veterans, but also employees, right? So my, my mom's a nurse and my dad is he has a job in the government. And so it's in, in law. And so we're really like, like very much not entrepreneurial people.

[00:06:50] My husband's family similar. And so it was really just kind of figuring it out as I went.

[00:06:59] Sanjay Parekh: Yeah. Okay. So I gotta ask then, what was the reaction when you told people in the family, yeah, I've got this good job, but I'm gonna quit it to do this entrepreneurial thing of my own.

[00:07:11] Jennifer Bower: So honestly, I have been so lucky to have just so much support and they're really proud of me. Part of it, I think, is that we as a family had worked really hard before I went out to do this on my own to make sure all of our financial foundations were really well shored up and that this was a leap we could make without necessarily rocking the book too much. And, you know, my husband's a pilot and so he travels pretty extensively. And I think my family was a little relieved that I would be able to work more flexibly and kind of set my own schedule and be able to, you know get a little quality of life back jokes on them. Because you know how it is when you're an entrepreneur. You're like, you're never really not working.

[00:08:00] Sanjay Parekh: It's and I think we'll touch on that in a little bit. It's funny because it usually goes one of two ways with people, right? It'll be, wait, you've got a really good job. Why are you quitting that again? Or Hey, I'm really happy for you. How can we help you? Like it's, yeah, there's no really in between those two things.

[00:08:19] And I've been I've definitely had the former when I quit my first job, to start my first company, like. From my parents, like, wait a minute, so you're quitting your job. We don't really understand why. So yeah, it's it's always interesting to hear, especially from when you in a family where nobody else is an entrepreneur kind of that reaction. Okay, so you, you had this like itch to do this thing. How did you decide like, Hey, I'm gonna take my financial experience background, and that's the thing that I wanted to go do. Like how did you land on that idea as something that you wanted to pursue?

[00:09:00] Jennifer Bower: So at the time I was actually working with a really wonderful coach here in Charlotte. Her name's Carrie Ren. And she was someone who a friend had connected me with and was helping me kind of understand a little bit more about what I wanted to get out of life and you know, what direction I really wanted to build in. And thinking more kind of long term about the things that gave me fulfillment and she gave me homework at one point to take a day off from work and really think about what I wanted. And I had been struggling to take time off and I was, you know, just nose to the grindstone and trying to prove myself at what was then kind of a new job. And finally I listened to her. I took a whole half day off that, that time and spent time thinking about.

[00:10:00] Sanjay Parekh: An Entire half day. You're just crazy over there.

[00:10:04] Jennifer Bower: Which was it was tricky because this company at the time had an unlimited PTO policy. And you know how those are when you're kind of not sure like how much you're actually allowed to take, right? And so I didn't wanna be seen as abusing the policy, but at the same time, you know I really did need to spend some time doing some thinking and just interrogating my values and the things that kind of lit me up when I was working, the things I wanted to be doing, more of the stuff that shut me down and frustrated me, and I'm like, well what kind of a job could I do where it, it looked like more of the stuff that makes me happy and gives me energy. And, you know, a whole lot of web searches later, I stumble across, you know the different types of career fields that exist in, you know, giving financial advice to people and the advisory field had, you know, different barriers to entry, but financial coaching sounded like something that I was pretty excited to do. I wanted to work closely with people and, you know, help them become more empowered in their lives. And I had the expertise on my own to do some of that financially and give recommendations to people on their you know, their financial choices but with a lens of compassion. That was something that I was, I really wanted to do. I didn't want people to feel shame about their finances. And so, you know, kind of seeing, well, hey there's this field that kind of blends the, you know, care work that I wanted to do with an expertise that I have.

[00:11:48] Sanjay Parekh: Yeah. was there anything that like going through this process that made you nervous about starting your own thing and yeah. So what was that? How'd you get over that?

[00:12:01] Jennifer Bower: This is gonna maybe infuriate any of the aspirational entrepreneurs who are listening, but the only way to get over being nervous was to get out there and start doing it.

[00:12:12] I was really, you know, really great at building the theory and I had made my website and I, you know was doing a lot of planning. But the, you know, telling people what I was doing, soliciting clients, getting people, you know to really. Sitting down and do the work with me. I was terrified. It was just, it was something, and I know that sounds kind of crazy, but I didn't wanna, I didn't wanna make a mistake recovering perfectionist, all or nothing thinker, you know? And it's like, well, if I'm not good at it right out the gate, what's the point? And I didn't know then that like especially in service-based businesses, your clients will teach you what you need to give them.

[00:13:01] And so I, you know, I started helping some people pro bono to get those reps in and you know, I didn't feel as bad about that. because I'm like, well, you get what you pay for. 

[00:13:15] Sanjay Parekh: I'll refund all your money. If you don't like it.

[00:13:17] Jennifer Bower: Yes. But you know, we, when as I did that work and I learned from people and I kind of learned what some of the pain points were and then, you know, it began the slow, beautiful iteration spiral that continues to this day.

[00:13:31] Sanjay Parekh: Yeah. So how did you decide on what kind of clients you wanted to work with and what are those that you like the most working with?

[00:13:43] Jennifer Bower: So the and I was listening to another one of your episodes with the organizer Dene. And I really enjoyed that episode. And, you know, initially the clients you work with right are the ones who will pay you anyone who comes in.

[00:14:01] Sanjay Parekh: Or that will take your pro bono work. Exactly.

[00:14:04] Jennifer Bower: Exactly. And then it kind of became, you know I was really kind of helping whoever came to me, whoever, whoever came across my threshold. Right? Very happy to help them. But then I also recognize that there were, there, there are people who have problems that are beyond the scope of what I can do and there are also people who want to be ready for change, kind of the like sign up for the gym membership and it feels like you're taking action, but like you don't actually go and work out, right? Yeah. And so, you know I have been very fortunate that most of my business after the first year or so when I was taking paying clients it's been just word of mouth referrals and people who send their friends to me.

[00:15:04] And so there's a lot of real but I have had the best results with people who are, very clear on their values. Who have recently, you know, either had kind of an awakening moment where they've gotten a lot of clarity or they've had a financial moment where, you know they've taken a new job and they're making a lot of money, or there's an inheritance or something else.

[00:15:34] Or alternately there's, you know, there's that reckoning. There's a divorce or a loss or some kind of catastrophe, and it's like, well let's get the let's get the train back on the tracks. And so, yeah, you know, people who are open to change, open to suggestion. Ideally couples who like care about each other and communicate well, if I'm working with couples or if I'm working with individuals, people who really thrive with that supportive accountability those tend to be the best environments. And, you know, it's a personality fit thing too. I mean, when you're, yeah sharing your budget with someone like that's about as close as you can get.

[00:16:18] Sanjay Parekh: Yeah. Is there, like, so thinking about the clients that you've worked with and the things that you've learned over time, is there something that you would say you've learned about entrepreneurs and small business owners? That would help them identify some of the challenges that they're going through or like bad habits that they've got that you'd say like, Hey, you should really think about this and figure out how to solve these issues.

[00:16:44] Jennifer Bower: Yes, absolutely. And I think, you know, entrepreneurs little bit different than the individuals. With entrepreneurs, I would say the biggest mistake I see people make is continuing to mix their personal and business a lot. When you mean on the financial side? On the financial side, yes. Yeah. Yeah. And I don't know if you see that, you know, you talk to a lot of entrepreneurs, but that's one of those things that, you know it's very easy to kind of slide, especially when you start out as a side hustle and you just kinda like slide into it and then before you know it, you're sorting through your entire year of bank statements trying to figure out what you need to talk about on your taxes, right?

[00:17:26] Sanjay Parekh: Yeah. No, that, that's definitely I have seen that before. Just as you have that is something that, you know, a little bit of pre-planning helps with that because it makes tax season and just, That much easier and then less risky that you're gonna do something wrong or Yeah, whatever. Is there something, so beyond that, is there, you know, like any other financial stresses that you've seen either with people or especially with entrepreneurs that you've got strategies around about how to help them avoid those or at least manage them a little bit better?

[00:17:59] Yeah. One thing that, that comes up a lot with individuals and it can come up with entrepreneurs, which is kind of the opposite problem is adding more complexity than you actually need. And so you have a system that doesn't, that's not very resilient to when life happens. Sometimes I have clients who come to me and they have been doing so much work.

[00:18:26] Jennifer Bower: They have, you know, read the books. They've watched the YouTubes, they've listened to the podcasts and they've opened up like multiple different bank accounts and they're trying to pay, you know, bills out of these different accounts and spend out of this account. And their spouse gets a special account, but their life isn't really set up for high complexity management. There isn't some like magical third person who's making sure all of that happens. And so really like we, we need the least complexity that gives you decision, useful information. And so for people, you know I tend to vector them into a budgeting app where it doesn't really, it's kind of a account agnostic.

[00:19:11] But we can understand where the money's going and what's happening in your finances. And it doesn't really matter what account it's coming into or going out of, and that can really help kind of calm things down because there aren't these mysterious things happening here or there, and you have to quickly transfer money because, you know, the auto saving app scooped out $50 and you know, you forgot that was set up and all of that. I just, I have people who are constantly stressed out and my whole thing is like, what can we subtract so that, you know, you don't have to be as hands on because as much as I love this work. I don't want you or whoever I'm working with, to have to spend more than a few minutes a day and maybe like an hour of planning on, right? Managing your financial life. It should be like brushing your teeth.

[00:20:04] Adam Walker: Support for this podcast comes from Hiscox committed to helping small businesses protect their dreams since 1901. Quotes and information on customized insurance for specific risks are available at Hiscox.com. Hiscox business insurance experts.

[00:20:25] Sanjay Parekh: Okay. So far we've kind of painted this as kind of rainbows and ponies for you, but I would, let's pull back the covers a little bit. Has there been a financial mistake that you've made as a founder that taught you a lot? And how did you deal with that?

[00:20:41] Jennifer Bower: Oh man. I don't wanna say my biggest mistake was not as a founder. My biggest mistake was buying a house in Florida in 2007. Okay. I was, take that I was a baby lieutenant in the Air Force. And so I got a lot of learning in you know, upfront and recognizing like, okay some of these things you know, that we trivialize as like minor financial decisions are in fact the biggest financial decisions you're gonna make.

[00:21:15] Buying a house is huge. As a founder, I think my biggest mistake, and I do see a lot of founders making this mistake, was not paying myself early on. I was just kind of hoarding all my cash that had come in because I was like scared that. Something might happen, or I thought maybe I'd, what if I wanted to, you know, invest in something for the business and I didn't have it. And so I, I went a really long time not even paying myself a token amount. And that was kind of silly, but I see a lot of entrepreneurs do it.

[00:21:46] Sanjay Parekh: I, yeah. Did you did you accrue for yourself. Like what you should be paid. Do you think about it that way or you just didn't pay yourself at all?

[00:21:56] Jennifer Bower: Anytime someone sent me money, it went into the account that I was using as my business bank account and it stayed there.

[00:22:03] Sanjay Parekh: Yeah.

[00:22:04] Jennifer Bower: I didn't, I, if I had a business expense to pay, I paid it out of that account, but I wasn't calculating how much I would spend. I was just like, I'm just holding onto this money.

[00:22:15] Sanjay Parekh: Yeah. Yeah. Interesting. Okay. Let's change gears a little bit. You talked about, and we talked about how the fact that you're a mom as well and you've got kids. So we all know entrepreneurship is not easy. It's not like a nine to five job necessarily. It's not this four hour a week thing that some people think it is. So how do you balance running a business like this and having kids and having a husband who travels quite a bit? Like how do you manage that for yourself? And then how do you account for kind of sleep and wellness for yourself as well?

[00:22:56] Jennifer Bower: That is so the question of the moment especially as we're recording this now, you know, summer is starting and we're, we are just headed into the season of everything changing. I am really, really, In love with my Google calendars. That has been the best thing for me. And I finally got my husband to start using one too, which has been I'm Thanks, honey. I really appreciate it. It's been huge because for me I have, you know, several days a week where I allow clients to self schedule their appointments.

[00:23:35] I can manually schedule outside of that time, but that really helps me keep certain days and times clear. And when I have other appointments or other commitments picking up the kids, doctor's appointments, whatever that gets blocked in. If I am working out when I was at a gym that, you know I would book a specific workout time and it would automatically, semi automatically populate into the calendar so it would make sure, you know, somebody couldn't book into that time.

[00:24:05] That was really helpful. And so yeah that's been huge. I, By exception only, I work outside of the school day. And so I try to really keep, you know the weekends and evenings at least, you know, notionally available. I can sometimes, you know, sneak some extra work in there. I really love sleep so much.

[00:24:34] Sanjay Parekh: This is. This is a very interesting comment from somebody who used to be in the military. because y'all are very regimented in that.

[00:24:43] Jennifer Bower: Well, I'm not in the military anymore, which should tell you something. It wasn't really a fit for my personality in a lot of ways, not least of which is that I'm not naturally a morning person.

[00:24:57] I read on the internet recently that, having kids turns you into a morning person the way that getting chased by a bear turns you into a runner.

[00:25:10] Sanjay Parekh: Sounds right and. Yeah. I identify with that comment completely. So I think we, we figured out why you're not in the military anymore now. Yes. With sleep, it was all sleep. It was other than that, it would've been fun. Yeah. So thinking back kind of now over these years, three years that you've been doing this full time, four since you started as a side hustle. Do you think about anything that you've done that you're like, man, if Could go back and do that over again. I, this is how I do it now.

[00:25:44] Jennifer Bower: Oh yeah, absolutely. I was really fortunate I worked with a business consultant Jessica Lackey. She's really fantastic. And she had a group cohort program. And in that program, I learned to think about what kind of business I was actually running. Prior to that point, I'd been, you know, running things on my own for about a year and a half and, you know, kind of muddling through and didn't really recognize that there was a big difference between a lot of the one size fits all advice that I was getting from the, you know.

[00:26:25] Internet and from some of the business books versus from, you know, like what I'm doing is really running a, you know, small client retainer, you know, individual. Like, I need deep relationships with people I need. I'm cultivating long-term stuff. I don't ever need to place a social media ad that's just. That, like, who's gonna randomly start talking about their money to someone because they saw a Facebook ad. Right? Right. And so really understanding more about what it takes to build your authority as a thinker in the space. Not to try and get clients necessarily, but to kinda, you know, shore up. People's trust in you once they've found you, once their friends have said, Hey, I've worked with this person. She's great. And then they go to your website and they read, you know, how can you get your voice and your knowledge through in a way that maybe helps them? A lot of what I find myself writing now is, you know, something I can send to somebody who's who I've already had a conversation with, to just help guide them through a recommendation I've made. And just kind of understanding like there's a beauty in that depth, but a lot of the advice that's out there isn't for people who are running those like small, deep soloist businesses.

[00:27:49] Sanjay Parekh: Yeah.

[00:27:50] Jennifer Bower: So I wish I had understood the business that I was running and that I wanted to run a little sooner. That would've been, that would've been a really a really great thing. But, you know, you find the teachers when you're ready for them. I don't know if I would've understood it, if I had found it, found that, that knowledge earlier in my journey.

[00:28:08] Sanjay Parekh: Yeah. You might not have been ready for the lesson Exactly. Before you actually were. So okay. Last question for you. If you're talking to somebody that was thinking about doing what you did and launching a side hustle, or taking their side hustle and making it a full-time business, what advice would you give to them?

[00:28:28] Jennifer Bower: If I were talking to someone who wanted to take a side hustle and move it into that full-time space I would encourage them to take their, they're a really comprehensive audit of their personal financial life as well as their business financials, and understand what they need their business to do and how consistently they need their business to do it in order to maintain the lifestyle that they're currently in.

[00:29:04] They might not need their business to do anything if they have adequate savings. Or, you know, a reasonable cost of living or a partner whose income can kinda shoulder the main burdens of the household while they build. But there's a lot of this like leap in the nutshell up here. Recommendation engine out there that I don't love because sometimes you, you actually do need to like more, have more of a gradient shift away from having a full-time job and a full-time income into like your business supporting you or you may, you, your business model may never be able to support. It's not a question of growth, but it's just a question of like, you'd have to work, you know, a hundred hours a day to make this work right?

[00:29:48] As you know and keep. Keep all of the things in your lifestyle the way you want it to. And with that knowledge you can make those decisions, but without like really understanding how those two pieces play together, your personal and your business finances it's gonna be really challenging for you to feel confident because like the great thing about the way that I feel, I did it not to brag, but you know, I was very cautious about.

[00:30:16] When the time was right for me to take this and do this as my whole thing. And so I was able to say no to things that didn't feel aligned. I was able to say no to things that felt yucky or stressful and really say, you know, plugged into my values. And I don't want anybody to have to feel like they're doing something that, that isn't aligned or that doesn't make sense or taking on debt or any kind of what any kind of unnecessary risk because they have fear and they don't have enough information to make a good decision.

[00:30:53] Sanjay Parekh: Yeah. Yeah. Great. Great response there to that. Jen, this has been fantastic. Where can our listeners find and connect with you online?

[00:31:03] Jennifer Bower: So, I am not very active on social media. Occasionally, when I write something, I'll share it online. But my main outlet for communicating with people, I have a substack. And it is fortuna money on Substack. So that would be the best place to find me and stay in touch. I have a newsletter that I write, I try to send out once or twice a month and share personal finance tips and some stories about, you know, things that have happened and just, you know, try and help keep everybody informed and plugged into their to their best and calmest financial life. Linkedin.

[00:31:43] Sanjay Parekh: Awesome. Thanks so much for being on today.

[00:31:45] Jennifer Bower: Thank you, Sanjay.

[00:31:50] Sanjay Parekh: Thanks for listening to this week's episode of the Side Hustle to Small Business podcast, powered by Hiscox. To learn more about how Hiscox can help protect your small business through intelligent insurance solutions, visit Hiscox.com. And to hear more Side Hustle to Small Business stories, or share your own story, please visit Hiscox.com/side-hustle-to-small-business. I'm your host, Sanjay Parekh. You can find out more about me at my website, SanjayParekh.com.