Lisa Drennon: Hey, hey everyone. Welcome back to this episode of I Date Money. I'm your hostess Lisa Drennan, your Wealth Activator. Today we are with a very special guest. She has been a trailblazing entrepreneur who made her mark on Wall Street at 25 years old. She is named one of Fortune's People to Watch. She's the founder of Mom. a platform empowering women to launch businesses from passion and purpose. I know a lot of you out there are thinking, yeah, I want to do my passion. I want to tap into my gifts and talents and serve my people in the way that feels good. Because if it doesn't feel good, we don't tend to do it. We tend to shy away from it. she's written her newest book, The Life-Changing Power of One Question, which is available now. So please welcome Holly Hurd. Thank you so much. I love this one question and I'm curious to know what is this all about?

Holly Hurd: Everyone says that. say, what's your new book? The Life-Changing Power of One Question. What's the question? I'm like, you have to read the book. But you know, it's not just, it's not one question. I mean, the overarching idea is figuring out what makes you happy. And it's targeted towards women. We have spent the first 50 years of our lives taking care of children, spouses, partners.

Lisa Drennon: You

Holly Hurd: parents, employer, we really haven't had a chance to take care of ourselves or reassess who we are now. ⁓ One of the questions in the book is, who am I now that I'm divorced? Who am I now that I'm a widow? Who am I now that my kids are out of the house and that is not my full-time job? Who am I now that I'm

Lisa Drennon: Mm-hmm.

Holly Hurd: retired or I have a different job. So book guides you towards questions that you to reassess where you are because our lives change over time. Our situation changes. And if you just keep going on, you're going to end up somewhere that you don't want to be.

Lisa Drennon: Truth. Truth bomb, everyone listening out there. You know, we tend to be people pleasers and I know, I think it's at 40. I know when I hit 40, yeah, when I hit 40, things completely changed. I went on strike and I used to make these gourmet meals for my family and then I was like, I'm so tired of you complaining. You're lucky if I even put dinner on the table. So when we think about, you know, a lot of women listening lack the confidence to take that next step to

Holly Hurd: or the end of it. Exactly.

Lisa Drennon: you know, like I used to believe that it was selfish to have self care to have me time to really put myself first. And I think we get, you know, it's ingrained in our brain because we spend so much of our lives serving others, you know, taking care of our families. And there's a lot of, you know, mompreneurs out there ⁓ are in that sandwich generation where they're not only taking care of their kids, but they're taking care of their parents. And it's So when you think about the challenges that women have to take this pivot, what kind of questions can they ask themselves to almost give themselves permission to say, yes, it's okay for me to do this for myself?

Holly Hurd: you're saying. ⁓ Things will go if I don't step up and take control. ⁓ you know, part it's control, part of it's guilt. You know, first of all, if the mom of the family goes down, the family goes down. We as women do ⁓ so ⁓ much. We're We're care of the food, the laundry, we take care of everything.

Lisa Drennon: Yeah. Mm-hmm.

Holly Hurd: And we also feel that it's our job. And if you're a single mom, it's certainly your job. Then let me tell you something, if you don't take care of you, your health, whether physically and mentally, you're not gonna be able to care for those people that you need to care for. So we need to stand up and say, listen, this is as important to take care of me as it is to take care of the people I need and want to take care of.

Lisa Drennon: Mm-hmm.

Holly Hurd: There should be no guilt around that.

Lisa Drennon: Yes, that is so true, but I think a lot of women feel guilty because, you know, like the way that they were raised, how they were, you know, just put others first before you take care of you. And having that balance is so important, especially as entrepreneurs. So what is something that you implemented in your daily life to help that balance and say, you know what, I get what you're saying, but I'm going to take care of me and there's no guilt involved.

Holly Hurd: You know what, over the last two years, I've had three surgeries around my hips and I broke my leg. So I was on crutches for eight months over the last two years. that's actually what allowed me to write my second book, The Life-Changing Power of One Question. but I work out with a trainer now. And it's not inexpensive, it's not super expensive, but that is really important to my health. I'm ⁓ gonna feel guilty about the cost, I'm not gonna feel guilty about the time. That is something that is in my book twice a week, and I go do that for me. It's made me ⁓ strong.

Lisa Drennon: Mm-hmm.

Holly Hurd: and feel so good about myself and able to walk again, ⁓ know, ⁓ that's a, mean, obviously being able to walk is a huge thing, but how about just being able to, ⁓ it's a yoga class, maybe it's ⁓ you know, time with your friends. ⁓ Community so important. So maybe you get a sitter one night a week so you can go out and have a glass of wine with your girlfriends.

Lisa Drennon: Mm-hmm.

Holly Hurd: There is nothing better. And I've done a lot of research on community for women. It makes you live longer. It improves your health. It makes you happier. hanging out with a group of women may seem like a luxury. That should be part of your everyday life because it is improving your health mentally and physically. That is a proven fact. Any doctor

Lisa Drennon: and

Holly Hurd: that I was just at a conference yesterday and one of his pillars is ⁓ and how it improves your health. So things like that you need to set aside and make time for. ⁓ what is the thing, your question, what is the thing that I can do for myself that makes my life better? Set aside time for yourself, put it in your calendar, make it as important as the kids pick up.

Lisa Drennon: Mm-hmm.

Holly Hurd: or the kid's doctor's appointment or your work time.

Lisa Drennon: Yes, and that is gold. we put it in our calendar, it becomes a priority and then it is and we are just as important because you can't serve and help others from an empty cup. And if we're feeling exhausted and tired, this affects the way that we're showing up in our business ⁓ it affects our profits. And a lot of women don't understand that. Like, you know, I'm just going to keep pushing, pushing, pushing. They get to the point of burnout. And then that burnout keeps them paralyzed for so many weeks. And then they're looking at their bank account thinking, ⁓ my goodness, I haven't received any money and my profits are dwindling. I can't afford to pay my team. And it creates a domino effect. And I always say health and wealth go hand in hand because if you don't take care of you, no one else is going to and you are your best asset. So when you think about that non-negotiable for your business when it comes to increasing profits. How did you personally discipline yourself to be able to say, okay, this is what I want to do. I want to hit my profit margin goal and these are the steps I'm going to take to take care of myself so that I can run a successful business.

Holly Hurd: that you can't do it all. what, you know, I'm usually sitting at my desk at six o'clock and I have forgotten all about dinner. I haven't gone to the grocery store. I have no idea what's for dinner. And...

Lisa Drennon: Mm.

Holly Hurd: That's not good, right? I mean, you need to eat a healthy meal. It should not be, you know, something processed. But so taking the time because you have to you have to be at your desk. You're called if someone needs you. I'm in a I'm a real estate broker. So when I have a house in play, there's I can't step aside. There's no one else to do it. Certainly, I have associates that could do some of the smaller things and delegating that.

Lisa Drennon: you

Holly Hurd: But some of the bigger things, it comes down to you. And women who are in a service business, they know it always comes down to them. So you need to have things in place, it's, ⁓ I'm gonna plan on doing the shopping ⁓ Sunday for all the meals and even making them so that I don't have to worry about dinner when I can work till six o'clock and know that I have a healthy dinner queued up. because I cooked it on Sunday or whatever day it is. So I think doing some of the prep work so that you're free to work and you're not left with, my gosh, I forgot to get permission slip for the kids ⁓ or that is, organize, get organized so that the important things ⁓ are done that you can focus on your job.

Lisa Drennon: Mm-hmm. Yes, excellent advice. Being organized, know, they say, you know, plan to, what is it, plan. I'm totally lost with words today. Thank you. Thank you.

Holly Hurd: Fail to plan, you plan to fail. Fail to plan, you plan to fail. Yeah, planning is huge. certainly when you have other people depending on you for meals or laundry or whatever it is that you have to provide, those things will be put to the side when you have a client that needs you. ⁓

Lisa Drennon: Mm-hmm.

Holly Hurd: You have to do something for your business, right? And you want to be 100 % focused on your client and what you're providing them. Otherwise you're not delivering your best self to your business. But if you know you've got the foundation for meals or pickups or laundry or whatever it is in your day-to-day life that always comes down to the women providing, right?

Lisa Drennon: Mm-hmm. Mm-hmm.

Holly Hurd: then if you have that foundation, you've organized a system for that, then you can be 100 % for your clients.

Lisa Drennon: Yes. And that comes from serving from the cup that overflows. You had mentioned that you're a real estate broker, and I'd like to touch base on that because I know there's a lot of listeners that are in real estate, ⁓ that want to invest in real estate. And as real estate broker, you work completely on commission. And one of the things I hear a lot from my clients is ⁓ being entrepreneur or working on commissions brings an inconsistent income. And it's very challenging to manage. ⁓ inconsistent income. So what's your secret to keeping things managed properly so that you don't feel broke?

Holly Hurd: Well, save for the rainy day, but in the real estate world right now, there's a lack of inventory. So if you're in one particular town, there are less houses to sell and there are more brokers trying to sell fewer houses. So I would say expand your market, right? So then if, so you have, you know, if you used to have a hundred houses to sell and now it's only 25, You need to expand your market to 25 houses and three other towns. So you have a hundred houses to sell. know, real estate comes down to relationships and building those relationships. I also, I also like an investment property that throws off positive cashflow.

Lisa Drennon: Mm-hmm.

Holly Hurd: And that may be hard to up with the income to purchase something, but a rental property, the best rental property is the dive on the best street. You buy it, you fix it up, but you've got to be creative in how you fix it up because you don't want to spend too much money. So you've got to get the right contractor, the right supplies. But if you research it enough and follow other people who have done it. And then you get a renter in there that's throwing off positive cashflow. And there's some very creative. So I learned about sleepy hollow New York at Halloween. People move out of their houses and rent their houses for five figures during October. So it could be your primary resident.

Lisa Drennon: Hmm.

Holly Hurd: residents, but they move out and rent them during, because Sleepy Hollow, the legend of Sleepy Hollow, Ichabod Crane, everyone's decorated, the traffic is crazy. People rent the houses to be at that location. one woman said she can make her entire mortgage. She goes and lives with her parents, with her kids, for four weeks.

Lisa Drennon: Yeah.

Holly Hurd: and makes her entire mortgage payment by renting to people who want to be there. yeah. finding unique places like that. Now, maybe you don't want to live in sleepy hollow, but find another place. College towns are great. My trainer, actually, who I go to twice a week to help me learn how to walk again, she and her partner,

Lisa Drennon: Wow!

Holly Hurd: have bought homes next to a university parents the rent and they generally rent to women, young women, and they want them to be safe. So parents are willing to pay high rents ⁓ and they rent those homes out from September until May and then they rent it to a summer crowd from June 1st to... ⁓ September 1st. So they're getting all of this income because it's by a college. It's, you know, university housing. And my kids have been through the process and I know we paid a lot for university housing. ⁓ And want your child, those houses are always rented. So that would be a good investment. So for ⁓ a estate person or anyone who has their own business,

Lisa Drennon: College town. Mm-hmm.

Holly Hurd: try and get a bread and butter gig. Like if you do plants ⁓ you're really busy in the spring and the winter, ⁓ you do gardens or something else that's your bread and butter ⁓ month so that you're not so cyclical.

Lisa Drennon: Mm-hmm. Right. I love that suggestion because a lot of the, you know, the feeling of having that erratic income is inconsistent. But if you manage it properly and then you can create different income streams to supplement that income while it's coming in, but you're not burning out. I know I'm an independent insurance broker, so this is my busy time of the year with open enrollment and tons of things are changing for 2026 in the health care industry. So like I know I plan for this like this is really busy time of the year and just balancing my time and taking care of myself so that I don't get burnt out. And then knowing that like all the income that you know, all the commissions I earn, I don't get paid out until February. So you know, you have to wait for those commissions to come through. And it's the same with real estate. And I love the investment piece because there's there's a lot of people flipping houses, but flipping a house and actually buying a house and renting it is completely different. You know, if you are going to flip the house, you do want to be able to have the skill set to

Holly Hurd: Yeah.

Lisa Drennon: to make it worth your while, because I know a lot of people who go upside down, or they buy land in places that just aren't going to ever sell. You know, so they don't get a good ROI.

Holly Hurd: No, that's tricky and it's very competitive. So you want to definitely do your homework. Here's a better idea to be honest with you. If you're a real estate broker, an insurance broker, or you've got something you do, diversify your income. Maybe you can teach math. And in affluent communities, people will pay you a hundred to $200 an hour to tutor their children. Maybe you're really good at You know, and this is something I talk about in this book. And also this is my first book. Like, what do you enjoy? Who, this is a great question. Who do you enjoy being with? So my sister-in-law loves elderly people. She can be with them for hours. will pay her to ⁓ their mother to the grocery store, to the hair salon.

Lisa Drennon: Mm-hmm.

Holly Hurd: to go over there and play cards with them for an hour, to take them to a well visit. So come up with something that's maybe outside of real estate, which might be so cyclical or whatever your business is, something that's different, tutoring children, caring for elders. But if you don't like children, that's not, you you need to ask the life-changing question, who do I like to be with?

Lisa Drennon: Mm-hmm.

Holly Hurd: Maybe you like to be with dogs. Let me tell you, I know a kid in college who makes 250 grand a year dogs ⁓ walking dogs. People will pay a fortune to have their dogs cared for. So there's so many side gigs that can give you ⁓ income, you know, mostly in the service area.

Lisa Drennon: Mm-hmm. Mm-hmm.

Holly Hurd: but you have to match to where you are. So if you're in Arkansas, you know, the hourly rate may be 75 an hour. If you're in Greenwich, Connecticut or Palm beach, Florida, the hourly rate is more like 250 an hour. An overnight dog sitter gets 125 a day. So those are things in Connecticut. Yeah. That's a lot.

Lisa Drennon: Mm-hmm. Wow. And Connecticut? Yeah, that's a lot.

Holly Hurd: So figure out, and that's so easy to research. I have an article I wrote, six hours to a side gig. know, figure out, ask the question, who do I like to be with? And then figure out, is there someone else out there doing dog sitting? What are they charging? well, here's my number. And then you say, I'm Susie Smith dog sitting, ⁓ you set up a one page website, you do it yourself, and you send your, I'm Susie Smith dog.

Lisa Drennon: Mm-hmm. Mm-hmm.

Holly Hurd: dog sitting, you send that to your friends and family and say, spread the word. then you just start telling everyone you know, you've got a business card, anyone need a dog sitter, dog sitter. Because as a broker, all points, ⁓ get at all points. Does anyone know a dog sitter? My sitter is sick this weekend, I need someone tomorrow for three days. So there's many opportunities to make extra money.

Lisa Drennon: Mm-hmm. I love that. Well, what's the title of your first book?

Holly Hurd: So my first book is Venture Mom from idea to income in just 12 weeks, but you can do it in six hours. But I give you 12 weeks to the first three chapters are about, you know, the life changing questions, figuring out what you really enjoy doing and who you like to be with. Maybe you like to be in an antique store. So maybe you become a personal shopper for

Lisa Drennon: Beautiful. Hmm.

Holly Hurd: women who don't like to shop and have no idea what knickknacks to put in their bookcases. There are women here in Fairfield County that charge $2.50 an hour to decorate your bookcases. Maybe that's your jam, but it's gotta be something you're really passionate about, right? Then people will use you and see your love for it. If you love dogs, they're gonna see that and they're gonna say, ⁓ my God, this woman loves my dog and takes the best care of her.

Lisa Drennon: Thank you. I love that. That's such wonderful tips. For those of you listening, get those books and visit Holly. She's going to tell us the best place to connect with her at. But these are really good things. You already have gifts and talents in which you can utilize those skills to earn money while you're building out your business or if you're working on commission. you can fill in those points where you're waiting for that commission to come in. So you always have that steady income stream. You always have that financial freedom that you desire. It'll be there and it'll help boost that confidence that you desire so that you don't feel broke, but you feel empowered and you feel like, money and I, we get along really well. So Holly, what's the best place for our audience to connect with you?

Holly Hurd: VentureMom.com and I sign up for my newsletter once a week. I do a story of a woman who has started a business out of thin air. So I talk about how she came up with the idea, how she came up with her name, how she got clients. So the idea is that I'm sharing the story so that other people can get inspiration on how to start their side gig or their business.

Lisa Drennon: Beautiful.

Holly Hurd: And then the other newsletter I do is what would VentureMom wear? And feature women-owned products. So she would wear this shirt from this vendor, this necklace from that vendor, these earrings. Maybe she gets her hair done from this, ⁓ female vendors. my my mission is supporting ⁓ female-founded

Lisa Drennon: I love that. That's beautiful. Well, thank you so much for being here and sharing your expertise. those of you listening, visit venture.com, get those books and start thinking. Venturemom.com. Thank you. Visit that website. The link will be in this show notes and really start thinking about how can I serve using my gifts and talents? Because remember, it doesn't matter how much money you have, it's what you do with it.