Cheyenne Crawford, HomeStar Photo

[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 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.” 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. These entrepreneurs are pushing the envelope while keeping their values. Keep listening for conversation, context, and camaraderie.

[00:00:54] Sanjay Parekh: Cheyenne Crawford has always been behind a camera. Taking graduation photos and prom pictures in high school, she knew that capturing moments was one of her innate talents. After Cheyenne realized that a traditional college path wasn’t for her, a chance opportunity to shift the subject of her photography emerged. She began focusing her lens on real estate. Cheyenne now works full-time capturing homes for sale in Atlanta at her business, HomeStar Photo.

Cheyenne, welcome to the show. We're super excited to have you here.

[00:01:25] Cheyenne Crawford: Hey, Sanjay. Thanks for having me.

[00:01:27] Sanjay Parekh: Okay. Tell us a little bit about your background first and then we'll get into what you're doing now.

[00:01:32] Cheyenne Crawford: Yeah I'm Cheyenne Crawford. I'm 24 years old. I own a small photography videography company that specializes in real estate media and I've been doing what I've been doing for two years full time. First year would be my third year getting it off the ground. I'm originally from Thomaston, Georgia.

So about 30 minutes north of Macon, really tiny rural town. And now I serve all of the Atlanta market. I live in the North Atlanta area. And that’s it.

[00:02:05] Sanjay Parekh: Yeah, so, okay. So, background wise, you were at Georgia Tech, you were getting a degree, decided to drop out, because you realized... that's not fun. And then decided to start this up right away? Right afterwards?

[00:02:22] Cheyenne Crawford: There was actually a good year, year and a half, maybe even two years where I was just doing the normal early twenties thing, waitressing, barista-ing, stuff like that.

Trying to figure out what this step was from that. So, as you said, I did go to Georgia Tech. I lived in Atlanta for about five years, and I went to Georgia Tech for about three and a half. And I just decided that it wasn't for me. I knew that there was more out there for me and that I really wanted to do something that I could create myself as opposed to a major-specific program.

So, after that third and a half year, I was just like, okay, maybe I need to take a step back and find something that's more true to what I want to do with my life.

[00:03:05] Sanjay Parekh: So was this the first time you've done something entrepreneurial? Or had you done entrepreneurial things when you were younger?

[00:03:12] Cheyenne Crawford: I would say this is the first time I've really ever ran a business.

All throughout high school, photography was always a huge passion of mine. So, my parents always raised me though, like doctor, lawyer, engineer. I'm a first-generation college student. So, there were a lot of really high expectations on me to do well in school and go get a degree and maybe a couple of degrees.

And I always had this passion, kind of in the background running, that I love photography. So, I was always in high school picking up little side jobs, shooting prom photos, senior portraits, graduation photos, all that kind of stuff. Anytime I could get behind a camera and get paid for it, even if it was just 50 bucks, I was going to do it.

[00:04:03] Sanjay Parekh: Okay. So, you were doing the side hustle thing before and then took a break to go to college and then kind of picked the side hustle back up and started it up again, it sounds like.

[00:04:19] Cheyenne Crawford:  Definitely.

[00:04:20] Sanjay Parekh: So when you made that transition, as you were figuring out what you wanted to do, why did you think about and decide to go into real estate photography videography versus… I mean, you could do anything, right? There's so many things -- you can take pictures of everything. Why that specifically?

[00:04:33] Cheyenne Crawford: So real estate was kind of serendipitous for me. It's kind of surreal looking back because I would have never, ever believed that I could make a living at photography.

It was really a blessing actually. At the height of the pandemic, when we had just started to lock down, my future mother-in-law has actually been shooting real estate for 15 years. So, she was one of the early founders of this industry in this area. And she got to the point where she had more work than she could handle.

And she was actually referring out to her competition and just had more than she could take on. And she also wouldn't cover the Metro Atlanta area. She's strictly outside the perimeter. And she asked me, and I'd been with her son for a couple of years by that point, and she knew I had this love for photography, and she asked me, do you want to learn how to do this?

And I was like, absolutely, yes. So, she took me on a couple of different houses with her that were vacant. Let me get to see the process. And immediately I was like, this is for me, this is absolutely what I wanted to do. I had spent a lot of time actually doing kind of side hustles, working under other photographers.

So, I worked under a big commercial photographer in Atlanta for a little while, helping them shoot weddings, edit photos, all that kind of administrative stuff as well. Learning kind of the process of running a photography business. And then I had also worked for a small creative agency for a little while in college.

And that was really interesting and has helped kind of form my vision for the future as well, because they had the perspective of like, how does this media get applied to businesses? So, I kind of took all that with me. And when she put me into the real estate photography, I was like, this is absolutely what I want to do.

And it's a niche in the photography industry because every photographer pretty much is like, oh, I shoot weddings, I shoot portraits, all that kind of stuff. And I knew that wasn't what I wanted to do. And I knew that was really a grind, really a hustle, and really hard to make money doing. So, when I started shooting real estate, I realized very quickly that this was a niche that was for me and that I could make a living in.

[00:07:06] Sanjay Parekh: Do you miss having people to shoot? Because you're shooting buildings. And they're empty. Usually there's no people there. Do you miss that part of it? Or is it nicer because the house doesn't blink or anything.

[00:07:26] Cheyenne Crawford: I love it. So, I appreciate the best of both worlds. I do really appreciate shooting a subject that doesn't move, doesn't complain about this little piece of fat right here. Doesn't look at it and be like, oh, can we redo that? But I actually have come around in the past year to start to reintegrate a lot of my experience shooting people in more of a way that benefits businesses.

So instead of working B2C, working with consumers, I'm working a lot with businesses. So, I still do shoot a little bit of people. I'm doing branding photography. I just shot this past weekend, a periodontist’s office. So, I helped them get updated headshots, updated staff photos for their website.

So that's been the best of both worlds, but I limit how many people that I shoot these days and the purpose of shooting people.

[00:08:22] Sanjay Parekh: When you started moving into this fortunately you had the benefit of having your mother-in-law show you the ropes and everything, but as you started having to get into this, how did you get your first client?

Was it because of a referral from her? There was extra work? Or did you go out and had to find your own clients? Like how did you do that?

[00:08:45] Cheyenne Crawford: That's kind of twofold. So actually most of my clients now are totally generated by me. She really just gave me the tools to build my portfolio so that I could market myself. So, I started getting my first clients from getting some referrals from her and getting referrals from that. And we're a heavily-based referral business. Most of real estate is. We really, really value referrals in the real estate business. And also through my Instagram, I have gotten a ton of clients from my Instagram. And as much as I hate social media, I can't knock it for how much value it has given me and my business.

[00:09:24] Sanjay Parekh: Let's talk about that. How do you leverage Instagram to help you get business? Are you taking the pictures that you're doing for clients and then using those to highlight your work? Or like, how are you leveraging that?

[00:09:36] Cheyenne Crawford: Definitely. This is a topic I could talk all day about. I'm really passionate about this topic because I try to go in a different direction than most people recommend doing social media.

So, I do use a lot of my work in my social media, but I try to integrate it naturally into my personality. If you went and looked at my Instagram, you would see that it's very personable. It's very me. It's my name on it. It's not a business Instagram. If you comment or message me on there, it's me messaging back, it's me commenting back.

It's a good hybrid of who I am as a person and showing my life and my process and what I am like to work with. And then also showing some of my best work, talking about, instead of just posting a picture that I took or posting a video that I took, I really try to emphasize what that means to a client.

And I think a lot of mistakes that a lot of businesses make, not just photographers, I think a huge mistake people make on social media is just posting stuff out there being like, Hey look at this. Hey, I'm selling this. Instead of explaining, using social media as a really personal marketing tool, to explain to the viewer why this means anything, right?

So, like I'll go through and I'll post a picture that I took and I'll talk about what it was like behind the scenes, right? It might've been chaos behind the scenes. There might've been people hiding on the edge of the frame. We might've moved a ton of furniture around and out of the shot. It might've been a really ugly day and then I did some Photoshop magic to make it look a lot more inviting and bright, and I try to really involve my audience in the process.

[00:11:26] Sanjay Parekh: Okay. That's interesting. Yeah, you can do Photoshop maybe for the pictures, but it's probably a lot harder to do for the videos.

[00:11:37] Cheyenne Crawford: It's impossible. I'm not going to do it. That is not in they’re budget.

[00:11:40] Sanjay Parekh: Yeah. So, you're doing drone videos as well. I've seen those on your site. How do you manage like, hey, I've got to go shoot this house, but today it's raining. What do you do? Do you just reschedule or do you just go ahead and go through with it?

[00:11:57] Cheyenne Crawford: You can't fly a drone in the rain. I have a little bit if it's lightly drizzling.

So, I do make sure that we try to schedule, especially video, like that. Photos we can do a little magic on and replace the sky and stuff like that and make it look as though it were sunny. Video you do really have to prioritize good weather, good lighting, all that kind of stuff. So yeah, I do reschedule.

Actually, I have three shoots tomorrow that all need drone on them and it's raining all day tomorrow. So, I have to take my day off on Thursday and reschedule them all for Thursday so that we can get the appropriate weather for them to get the service they need.

[00:12:39] Sanjay Parekh: So, it looks like you're taking tomorrow off instead then?

[00:12:44] Cheyenne Crawford: If you work for yourself there's really no days off, unfortunately.

[00:12:48] Sanjay Parekh: Yeah. That is one of the not well-kept secrets. I think everybody knows this about being an entrepreneur is that you're always on, you're always the one on call. So, let's talk about the company now. So, you've grown it somewhat over the last couple of years. Is it still just you and do you have contractors or do you have employees?

How are you managing the company right now?

[00:13:11] Cheyenne Crawford: I am currently working on bringing on my first employee. It's grown so much to where my partner Kay, is fully booked. I am now fully booked. And growing the business even more of a production kind of scale. So instead of just photos, we're moving into more holistic marketing, if you will.

So, photo video, how do you put it out? How do you use it on social media and your website? Stuff like that. Branding photography. So, I have definitely needed some help in that regard. I'm bringing on my first photographer who's going to take over some of that workload day-to-day. And he's also just graduated with a degree in graphic design. So, I'm really excited for that because that's going to help me add another facet to our business and services that I can offer to my agents to make more of a complete picture of their marketing.

[00:14:36] Sanjay Parekh: Right, right. That's awesome. So you're thinking about just kind of then expanding the offering suite. Is this something that you've heard from clients that they'd like to have? Or is this something that you just realized that they need, that they don't realize that they want or need?

[00:14:55] Cheyenne Crawford: It’s a little of both. So, I pay really close attention. I'm plugged in with a network of real estate photographers, videographers, and also agents nationwide. And so different things are happening in different parts of the country right now. Down in Georgia, we're still a little behind the curve in terms of how many people are utilizing more forward-thinking, tech-driven marketing like video. Video is still pretty new in this market. Whereas out in California, they've been doing it pretty heavily for the past three to five years.

Same thing with New York City. So, I do have agents that are forward thinking and know that it's something that they need to start adding into their business. It's still at the cusp. So, my agents right now that are thinking about the next five years are definitely starting to double down on those extended-out services.

Whereas I think in the next two to three years, the agents that are just deciding to get into it then are going to be late.

[00:15:37] Sanjay Parekh: Ah, that's interesting. That's interesting. So working in real estate and then also being a founder essentially, right? So, you're different than just like a real estate agent and thinking about listing houses. It's a job where you've got to be self-motivated about things. And thinking about what do you want to accomplish on a day to day, week to week, month to month, year to year basis. So how do you think about those in terms of your business? And how are you setting your goals and priorities? You're just now realizing, Hey, we need to hire an employee because the two of us are fully booked.

What did it take for you? Did you realize that was coming before it hit?

[00:16:19] Cheyenne Crawford: It came way faster than I thought it was going to be honest.

[00:16:24] Sanjay Parekh: What was it that, you said, Hey, we got to pull the trigger. Was it a certain amount of revenue that you got to? Or was it you just didn't have the time? What was the deciding factor to that?

And then looking forward, how are you thinking about what are you going to try to accomplish in the year? Like, how are you planning for those things?

[00:16:41] Cheyenne Crawford: I think for us, what kind of tipped it over to make me think it's time to bring on another team member was actually not necessarily revenue driven.

The way that we're functioning right now is it's like our time for money. So we can only make as much money as we have hours in the day to go out and shoot. That's our highest income generating activity, the best and highest use of our time, as real estate agents like to say.

And I think it became the right time because we started having people reaching out to us, wanting to work for us, seeing what we were doing, seeing what I was doing on social media and being like, that looks so cool. I really want to get into that. So I've had a few people reach out to me, do you have extra work. Either photographers that are already experienced in this niche or photographers that do it on a hobby basis that are like, I really want to move into this professionally.

Can you teach me? Will you bring me on as a team member? And to me, I'm a big, like quality over quantity person. So, I would have been happy running this business, just me, for the next three to five years. And that's what I really thought it was going to be before I ever felt prepared to bring on an employee.

But I had people come to me at the right time that seemed like such a perfect fit. And I think it's so important for the sustainability of your growth to bring on really quality employees that are going to stay with you for the long run. And that's what I knew I wanted for my business in the long run.

So, you were talking, asking about setting goals, which has really shifted. My whole thought process on setting goals has really shifted for me, actually being in business for a little over two years now. When I first started out, and I'm a big forward thinker, I'm a big, big goal setter, and it's hard for me to see the day to day in the big picture.

So, I definitely lose the trees in the forest sometimes. And it was a big shift for me because I started out thinking, oh, like I want to have a creative agency. I want to have all these big commercial properties and everything to do. And I had all these big vision dreams and really no practical knowledge to apply to it, that would get me there. And I have realized how much I don't know by actually doing. So, it helped me to take those really big goals and break them down into okay, I have to just keep going every day. Like I just have to keep putting in the work every day and it's going to get me where I'm wanting to go.

And that has really shown itself to me in the past. Because so many of the seeds that I planted early, and I'm a big believer in like manifestation and stuff. So if you set the goal and you keep talking about it to people and you keep thinking about it and you keep centering the work of what you want it to become around.

You're planting seeds the whole time. And when I first started, I was like, oh, I want to have all these full package clients that are doing photo, video, drone, Matterport, branding on every single property that they do. And it took me having those clients for two years, putting that bug in their ear and slowly building up the value in their minds about that and showing them the evidence that I saw, other places of other people doing that, for those agents to finally, even now, even just this month, coming around and telling me, this is what I want to start doing.

And it's kind of crazy because they say that's when you're in alignment, is when all those things start to pile up and start happening and set into motion. And it's been a lot of momentum-building the past, I would say, six months.

[00:20:51] 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, the business insurance experts.

[00:21:12] Sanjay Parekh: How are you balancing work versus your actual personal life?

[00:21:19] Cheyenne Crawford: Well, I am super, super fortunate to have a fiancé who works damn near as much as I. He's a car salesman, so he gets like every Thursday off and then every other Sunday off. And even with him, it's kind of the same deal. If he's got clients coming in and he knows he's going to close a deal and he's like, babe, I know it's my off day, but I’ve got to go in and close this deal. And it's the same way with me, like we were going to take Thursday off to be together. But I told him today, I'm like, sorry, babe. I’ve got to take these three appointments on Thursday and he's like, that's okay. We'll make it work. I don't have kids. So that is a huge help. I know that takes a lot of people's time, especially running a small business.

This is a good question. Cause I don't know if I balance it that well. I'm working on it. I'm getting better at it all the time. The benefit has been, actually, I would say last year was probably the hardest year of my life, but for personal reasons. And just this business was growing and working out all the kinks and learning my clients and stuff.

So, I think last year was really, really, really challenging, but now I've got the systems in place that help me to manage it and help me to manage my time better. And I know the workflow like the back of my hand now. So, everything that I do doesn't take nearly as much time. However, there is a caveat. I am adding a lot more video this year and video is much, much more time consuming both onsite and in post-production.

Whereas I might send my photos off to an editor and have my evenings and have the photos back first thing in the morning and send them off to my clients, where the video it's much more meticulous. I have to be very involved in the editing process to make sure we can deliver a consistent product.

And it's much more time-consuming in the backend.

[00:23:26] Sanjay Parekh: Yeah. So, you've mentioned systems and tools a couple of times. What are some of those tools that you use that you could like not run the business without?

[00:23:37] Cheyenne Crawford: I would say my delivery platform. I'm actually an ambassador for them. It's called Aryeo. So, my partner, Kate, did a lot of research on what we could use to actually get those big files to our agents.

Dropbox was not cutting it. Dropbox, we have a lot of agents that are older and have been in the biz for a long time. And they don't have any idea how to like even unzip a file, much less go onto Dropbox, find it, unzip it, download it, all that kind of stuff, and then get it into the MLS.

So, we found a really amazing particularly dedicated platform for real estate photography. That has changed everything for us. The workflow is so much simpler now and it makes it a lot easier for our agents as well as brings to them a lot of value. Other systems I can't live without: my editor.

Like you're talking about time management and how do I have a life outside of my business? It's my editor. So I have a really great overseas editor, that handles most of my workload when it comes to editing. And we went through editors with a fine-tooth comb. We've been through dozens of different editors to try to find one that fits our need for consistency, our turnaround time and our style.

I'll take that secret to my grave, who my editor is. ‘Cause you can’t have him. That has saved me.

[00:25:14] Sanjay Parekh: How did you find this editor?

[00:25:16] Cheyenne Crawford: There's a bajillion of them. So, there's ones in the Philippines. There's ones in India. They're all over and there are some stateside editors that are pricier, but their turnaround times are never as fast.

So real estate is very different from a lot of photography in that I shoot it today and my agents get it in the morning tomorrow or at the latest tomorrow afternoon.

[00:25:35] Sanjay Parekh: So, these editors that you found, you just went out and hunted them down yourself? You didn't use like a platform? You didn't go to Elance like a place like that to find them?

[00:25:46] Cheyenne Crawford: It's a specialized field. So, the way that we have found them a lot is there's a lot of real estate photography groups on Facebook and stuff like that. And then I have a lot of friends that do this across the country that I made online, which has been amazing, my network there is, I'm really grateful for them. So, I have found them through those kinds of platforms by talking to other people in different places that do this.

And that's how we found our editor because it's very specialized. It's not something you can just go find on Fiver and get a consistent product.

[00:26:23] Sanjay Parekh: Okay. Last question. What advice would you give someone who's curious about the real estate market, but is just overwhelmed about where to start and they know they want to do something in real estate, maybe it's photography, maybe it's videography, maybe it's something else. I don't know what. But how would you recommend somebody like that start and get involved?

[00:26:48] Cheyenne Crawford: So, I would start with a disclaimer. It's not what you think it is. It is not the glamorous thing that Selling Sunset and HGTV and all that stuff makes, it's not even close to that.

It's not just seeing pretty houses and making big fat checks. There's a lot of blood, sweat, and tears involved, and there's a whole lot of skill that it takes, even just beyond going and getting your real estate license. If you're interested in getting into real estate, I would say it's different whether you want to do photography or if you want to be an agent or if you want to be in the mortgage business or insurance or something like that. I will say it's an amazing industry to be in it's full of all different sorts of people.

Not all of them are savory, if you catch my drift, not all of them are the best example of the industry. But at the same time, I would encourage you if it's something you're interested in, to really do your research, and reach out to other people that are doing it in your area that you would like to be doing business like they do.

It's a very mentorship-heavy industry. It's low barrier to entry, but to be successful in it, it's actually very high barrier to entry and it takes a lot of time, takes a lot of investment. It takes a lot of skill. So, you need to have a mentor that can help guide you along and tell you the mistakes that they made so that you don't have to make them on your own dime.

Or you need to really invest in a good source of education for that. There was one more thing I was going to say about it too. Oh, also this is just like my little kind of ethical thing. I really, really love being in real estate because it's really making a difference in our communities and in a world, especially post-pandemic, that we're more disconnected than ever.

And we have more disconnection from our communities than ever. I really love that I do what I do, like, I’m getting chills right now. I love to do what I do because I get to meet people that live in my community every single day. And I get to be in touch, like I have my finger on the pulse of what people are really feeling like what people's lives are really like. It's very intimate.

So, if you don't like getting hyper personal with people and being in people's space, don't get into real estate. If you're a judgmental person, do not get into real estate. Because this is an industry that you're getting really, really involved in people's lives. And some of people's greatest asset that they will ever have in their lives.

And while that's really wonderful, it's also something to be taken really seriously and guarded really closely and with care.

[00:29:51] Sanjay Parekh: Yeah. That's great. That's great advice. It sounds like also patience, if you're going to get into real estate have lots and lots of patience, because it's going to take a while to really get to the top of your game.

[00:30:02] Cheyenne Crawford: I was going to say, patience with people.

[00:30:04] Sanjay Parekh: Patience with people. Cheyenne, if people want to find you, where can they find you and your business?

[00:30:09] Cheyenne Crawford: Yeah, you can find me on, Instagram's probably the best place, @cheyennecrawford.photo. That's C H E Y E N N E C R A W F O R D.photo. You can check out our website at homestarphoto.com.

HomeStar Photo, all one word, dot com. And then you can also check us out on Facebook at HomeStar Photo. Homestar is one word.

[00:30:37] Sanjay Parekh: Awesome. Thanks so much for coming on the podcast.

[00:30:41] Cheyenne Crawford: Thank you so much for having me.

[00:31:15] Sanjay Parekh: Thank you 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 if you have a story you want to hear on this podcast, please visit Hiscox.com/shareyourstory. I’m your host, Sanjay Parekh. You can find me on Twitter at @sanjay or on my website at sanjayparekh.com

[00:34:15] Sanjay Parekh: Thank you 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, if you have a story that you want to hear on this podcast, please visit Hiscox.com/shareyourstory.

I’m your host, Sanjay Parekh. You can find me on Twitter at @sanjay or on my website at sanjayparekh.com.