What Breaks Creative Businesses When They Try to Scale | Alex Morgan | Part 1

This episode isn’t about creativity or branding.
 It’s about what it actually takes to run a creative business inside real operational constraints.
 In Part 1 of this conversation, Alex breaks down how client work, team growth, and internal systems collide once creativity turns into a business.
 This was not an artistic challenge.
 It was an operating challenge.

We cover:

• Why creativity becomes fragile at scale
• How process debt quietly builds inside creative teams
• The constraint founders avoid addressing early
• What scaling demands beyond talent and taste
• The operator shift that determines longevity

If you’re a founder or operator working inside client pressure, team growth, or creative execution, this conversation will feel familiar.
 This isn’t a highlight reel.
 It’s a practical breakdown of how real creative businesses actually survive growth - under pressure, not in hindsight.

Chief Milestones is a video podcast featuring honest conversations with founders, parents, and investors about building real businesses, staying healthy, and raising families.

New episodes release Tuesdays and Fridays.

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Transcript

Why Workplace Happiness Became The Mission

Alex Morgan 0:06

Focused on supporting business and connecting with people. I felt even more alone and alone like I wasn't supported. I feel supported in what I was doing, but also being alone . So I wanted to create a business model for my thesis and focus on workplace happiness.

Meet Alex + What Chasing Cali Collective Actually Is

Reshma Vadlamudi 0:26

Do you think everyone is built for Entrepreneur- ship? No. Based on your experience today. What's one thing you would do differently if you were to start a little things you had to sacrifice to be where you are at today?

Alex Morgan 0:41

So it makes me sad. I did have to sacrifice. I'm Alex Morgan. I am a mom of three little ones. I am a wife to Anderson Morgan, and I am the creative director and owner of Chasing - Cali Collective, which is a family-friendly wellness cafe where we focus on helping work-from-home parents, caregivers to have a supportive environment where they can connect and take care of themselves as well.

Reshma Vadlamudi 1:16

Yes. So why Chasing - Cali?

The Thesis Idea That Started It All (11 Years In The Making)

Motherhood Revealed The Real Gap: Support + Connection

Alex Morgan 1:20

So it started probably about 11 years ago when I was majoring in fashion design and product development at DAP. I developed a business model that had a different target customer back then, but um I saw the toxic work environment in a corporate fashion. So I wanted to create a business model for my thesis that focused on workplace happiness and that developed where artists could connect with other small business owners and then they could also connect with their customers because in corporate you don't have that connection piece with your customer base. You're just designing and you're you know stuck behind a desk and there's a lot of like toxicity in your work environment. So I developed a business model that kind of focused on supporting artists and small businesses and connecting with people. So that was 11 years ago. Macy's gave me an award for that, and then along the way I realized that parents specifically, because once I became a parent, I felt even more alone and more like I wasn't supported. Um, working from home, doing this design work for our business, our construction business, I didn't feel supported. So that's how Jason Cathy came about, where I wanted to help people and specifically help myself too, because I was lacking that and I couldn't find um a place where I could feel supported in the work that I was doing, but also being a mom.

Reshma Vadlamudi 2:45

So at what point did you know that you wanted to be an entrepreneur?

Alex Morgan 2:51

I've always known since I was a child. Um my dad started his own business construction business when he was 18 years old. So I was always around um that world of entrepreneurship. When I was a little girl, I would like make pot holders or I would make jewelry. I was always like making something with my hands and wanting to sell things um that I enjoyed making. So I guess I've always known, but I just didn't know like what my main purpose in life was. It was always like I was trying to figure that out.

Reshma Vadlamudi 3:25

What point like what led up to Chase and Callie?

The Pivots: Etsy → Photography → Design → Commercial Space

The 3am Vision: Coffee + Childcare + Workspace + Wellness

Alex Morgan 3:30

So in 2018, 2017, I started an Etsy's Etsy shop. I was making custom apparel items in our house. Um, and then I got pregnant with our first, and I realized I wasn't going to be able to do that 9 to 9 a.m. to 9 p.m. making customer customer apparel items. Um, so I pivoted and I started doing wedding photography. And I got pregnant with our second, and she was exclusively breastfed. So my mom would come to the weddings I was doing photos for. I'd breastfeed her, and it was just becoming a lot, so I stopped doing that. And then Anderson he had his real estate license and he was wanting to flip homes. So he was like, Why don't you do the design work? Because obviously that is a passion of mine, is design. Why don't you do the design work for our homes that we were flipping and we can work together as a team? So I was like, okay, I could still take care of the kids, I could work from home, and it seemed to be like the best fit at the time. But I always told him that I didn't want to be a stay-at-home mom. I always knew that, and not because it's being a stay-at-home mom is a very important job, and it's one of the hardest jobs to have, but I knew within myself that I wasn't, that wasn't who I was to be just home with my with my kids. Um I knew I needed to do other work too, but it started to get to be a lot staying at home and working from home, trying to design things on my computer while I'm they're crying, climbing on me. Um, so then Anderson wanted to transition from residential real estate into commercial real estate. Uh, he joined like a mastermind group and we found the property that now Chase and Cali is in. And when I first saw it, um, I almost had an instant feeling that I wanted to do something within that space that went back to my senior thesis of creating an environment that supported people. So I actually had a dream one night that I was gonna have a coffee shop, temporary child care area, and then I'd have the workspace and have like the small business environment to support people. Um so I woke up Anderson, it was like three o'clock in the morning, I drew it all out and I showed it to him, and he was like, okay, yeah, that like let's do it. Um so yeah, it was just kind of almost a spiritual awakening too of being like, okay, this this feels like my calling in life and just going for it, even though there were so many risks involved and all of our life savings, everything um has been extremely scary at the same time.

Reshma Vadlamudi 6:08

Yes, I get that. How did you find that self-belief, like to take that first action? Because we all want to do something, and then we had to start somewhere. Right.

Alex Morgan 6:21

I started um going to different meetups of other moms that um had small businesses or that were doing different things and just surrounding myself with like-minded people. I don't say I remember going to it was called maternal instincts. I didn't even have a plan set in place. Is that a meetup? It's a local Cincinnati meetup. Um it's run by two different women that both have their own businesses. Um, but I remember telling them I just felt like I had a lack of purpose in my life. Like obviously, I have had that purpose of being a mother. Like, I'm here, you know, um, for my children, but what is my purpose outside of being mom? I was like, I don't even know what that is, but I just need I know I needed to surround myself with people that had that were doing things that were um that I was inspired by. That was my first step.

Reshma Vadlamudi 7:17

Do you think everyone is built for entrepreneurship?

Alex Morgan 7:22

No. Um, and that's okay. Everyone has to be different, or our world would be not the world I guess it is. Like we all need people that are service-based. Um, so for example, our massage therapist, Victoria, who I love dearly, um, I honestly met her from one of those mom groups I had posted in, and she had reached out to me and she was like, I've always had this idea that you have, but I've never been able or wanting to do it, but I want to be involved somehow. So I remember we met up for coffee and we just talked, like I shared my ideas. She was like, I love what you're trying to do and I would love to be a part of it. Um, she was like, but I know that like I don't want to run a business. Because I originally asked her, I was like, Do you want to in one of our spaces just rent a room where you can do massage therapy, you can be your own business owner? And she was like, honestly, like, no. She was like, I just want to provide the service and and help the business.

The Sacrifices: Kids, Time, Money, And “Never Balanced”

Reshma Vadlamudi 8:21

What did you have to like? I know you are talking about it along the way, but there will be so many little things that we're all sacrificing along the way. So, what are the things that would stand out to you when I ask you? What are the things you had to sacrifice to where you are to be where you are at today?

Alex Morgan 8:41

So it makes me sad. I did have to sacrifice um that one-on-one time with my kids. Um, I knew it wouldn't be forever. But like I said, like I was a stay-at-home mom with them while working. But the but while creating businesses, I couldn't do that. Um so it's been a major transition for myself and for them. But it's like I know I want to get back to that where I'm not having to be at JC Cali seven days a week from opening to past closing. Um, but to get it to the point that it needed to be at so that I can start to delegate more. I had I felt like I had to like fully understand my own business. Um, so like my kids um over the past year have said that mommy, we don't get to see you much, like you're never home, or like you're always on your phone. But I know that's something that I have to like work on, like being able to balance for balancing is hard because it's never when you're owning a business, you're never gonna be fully balanced. But how can I flow better and still be there for my kids because and be there for myself and for my husband at the same time? Like, where do you figure out what what you need to focus on? That is important. Um, because obviously I don't want to miss my children's childhood. Um, I want to be there for them. So learning how to delicate better is something I'm currently working on. But I have had to sacrifice this past year of spending as much time that I was with um and cutting back on our spending. Um like we we like to take trips. Um, this past year we haven't taken any trips just because it, you know, all of our time and money has gone into the business. But eventually, like that's it's not gonna be like that forever, you know.

Reshma Vadlamudi 10:46

Like hardest part about the business and how you are overcoming it.

Alex Morgan 10:52

I say the hardest part is learning how to manage it. Because I know I can be a pushover, but you can't do that when your business is online, too. You know, like I want everyone to be happy. But if the business is if the business doesn't survive, then no one has a job. So there has to be that level of like yes, I want to take care of your needs, but what are the business needs too? And how do we meet in the middle?

Reshma Vadlamudi 11:35

Based on your experience today, what's one thing you would do differently if you were to start over?

Alex Morgan 11:44

Um differently is in the beginning, I wish that me and Anderson had our exact roles set in place. Um in the beginning, he was like, This is your thing, you figure it out. I'll be here to support you, but it's it's your thing. Um and that caused a lot of like not resentment, but almost like, okay, I guess I'm in it alone. Um, but I didn't voice that to him. I was just like, all right, I'll I'll figure it out. Um so I wish I would have been in the beginning, like, I want to do this together because that's what I wanted. But at the time I wanted him to like prove it to me that he wanted, so it was like in my head, I was like playing this game instead of just being very vocal to him, like, hey, like, we're in this together. Like, if you and he wanted to be, but he also like thought that I wanted to do it by myself. So it was like this, like the miscommunication between us. I wish I would have handled it better, and just like us be upfront about like, okay, what are we doing? How can we both like add our specialties and like work together instead of like thinking that we were against each other? I wish I would have done that better.

Why Each Self-Care Service Exists (Sauna, Massage, Nails, Etc.)

Reshma Vadlamudi 12:58

So, what are some self-care services that you guys offer? And I saw that you guys have sauna, and I know you can talk about others that you have. And can you also tell me why each of those is in there actually?

Alex Morgan 13:11

Sure. Um, so we just added nails a couple months ago. So we can do manicures, pedicures. Um, why I wanted that was I always loved getting my nails done before I had kids. Um, I remember I would like text Anderson, like, hey, what color should I get my nails done? And he'd be like, I don't care, whatever color you want. Um, but that was always something that I loved doing because I loved like you know, my my feet look good, my hands look good because like I feel like I use my hands so much and talk with my hands. But after I have kids, like that was the first thing that that went away. Massage-wise, again, it's just like being able to take care of your body and reminding yourself that like your body deserves love and your body deserves to feel good. Um, so Victoria, she's an amazing massage therapist, and um just releasing that tension in your body that we carry, especially as moms. Like, we carry so much that we don't even realize. So that's why we have massage. Um, we also are offering couples massages now so that couples can reconnect too, and um, both mom and dad, both partners, um, can get massages at the same time. Um, that's something like me and Anderson like to do when we go on like vacation, or um, we've done it on like anniversaries where we get a couples massage together. Um we have the infrared sauna, so it's not a dry sauna, so infrared it goes on a cellular level and it helps to release you know toxins. Um, it also helps like in the winters, especially like with you know, when you can't be outside and in the sun, even though like you still have to think about being in the sun with cancer and whatnot, but um the infrared does help with um inflammation and uh immune boosting, so that's why we have that in there. Um we have a hairstylist that's her own business, so she just rents space from us, but she's amazing. That's another thing as moms, we kind of put on the back burner as like getting our hair done. Um, but it again it's another like thing that helps you boost your mood and helps you feel better when you look in the mirror. I remember looking at myself in the mirror one time and just hating how I looked, you know. Um and even though it feels like a superficial thing, because you still like have a love that you are on the inside too, but it was like I did I started to hate looking in the mirror and I hated that feeling. Um so yeah, getting my hair done does help me feel better. Um, we will have someone that's renting a space that does facials. Um, so to help with like skincare, uh we have um someone that's renting a space to do embroidery, so it's not necessarily self-care, but um just to create those like memories. Uh she does like sweatshirts where she takes like a onesie from like when your baby was an infant, and obviously they're a toddler taller now, but you have that memory, she can make a sweater where it says like mama on it using that like onesie that you like cherish.

Reshma Vadlamudi 16:15

What do you think is working with uh attracting and retaining customers?

Alex Morgan 16:21

What do you think is working with attractive customers? Um, social media has been a huge help. Um, and people think that I do it all on my own and I don't. I have people that do help me with that. Um one person that has helped me from the beginning. Um, her name is Courtney Plut. Um, she helped me during the day, kind of like managing it, and then at night is usually when I get on there. So if you see any like responses that are at like 8, 10 p.m. at night, that's usually me. Um during the day, obviously I'm busy doing other stuff, but um, she has done an amazing job um helping with social media to um get people excited about new things that we're doing and just like day, like you know, just what's going on during the day, too, of like what's going on in the coffee bar or what's going on in the play space. Yeah, social media has been a big help for that. Um, and then keeping customers, um I give any of our like members that have like a play space membership, they get discounts on any of our services. Um, and then we always try to like check in with people of like how'd your service go, or like what do you think we could change? Um, and just accepting that feedback to make sure that like if they did have like see something that we needed to change or that we could do better is like listening to them.

Reshma Vadlamudi 17:41

Yeah, what does your business provide? The mobs.

Alex Morgan 17:43

Yeah. Um I mean, the main thing is the childcare. Um so we have I think 50 members now, and their main thing is like they're trying to get stuff done at home, but they can't. Um, and that was my main thing of why I wanted to open Chase and Cali was to give that like sense of relief for them that their kids are right next to them, really, it's just in one room over. They can peek in through the windows and see how their kids are doing, but they can still get their work done. They can catch up on emails, they can even just meet with a friend for coffee to talk about their ideas, or even meet with their partner, and like because that's one thing that me and Anderson are still working on, but is like touching base without the kids screaming in the background, you know. Like, we love our children no matter what, but obviously, like it's hard to kids just finish the sentence, yeah. Yeah, so that's like the main thing that I would say, like that we're giving moms that they're saying that they need help with, like, you know, for even just that two and a half hour window of like just getting some emails done.

Reshma Vadlamudi 18:49

One self-care practice that has had the biggest impact on your well-being.

Alex Morgan 18:54

Alone time. Um, I'm an introvert by nature, so for me to recharge and me to feel okay is I need like an hour of just alone time, and that's something that like me and Anderson struggled with really like in the beginning of opening up Chasing Cali is like how do I still get that alone time? Because by the time I'm done working, you know, I have to get home to the kids and I need to start, you know, making them food and dinner. Um, but one day a week we kind of agreed on like I would have an hour where I could just be by myself, and usually like I'll get into our sauna at Chasing Cali, or even just like sitting by myself in silence helps me um just to be able to like recalibrate and then get back into it with the kids, and you know, I like to listen to audiobooks a lot. Um people make fun of me, and it's okay they can make fun of me, but I love listening to like like um not sci-fi, but like fairies and dragons and like stuff that has nothing to do with work, you know, it just takes my mind into a spot where I can like feel kind of creative and take my mind off of everything.

Reshma Vadlamudi 20:06

Challenges that you faced particularly, and how do you guys overcame those? Like maybe related to real estate, like flipping houses are particularly to Chase and Callie or whatever.

Alex Morgan 20:21

I think the main challenge is finding time for me and him. Um I tend to when I am passionate about something, I go all in and that's what I focus on. And I don't really think about other things, but I know that I should be. So one of our uh trigger points is that he thinks that we don't spend enough alone time together, or you know, we don't go on date nights enough and and I don't think about his needs, you know, which is hard, you know, because when you're first starting a new business, all you think about is all the needs that the business needs or all your all the needs for your kids because they depend on you fully. So your husband, or me at least, he became on the third back burner that um it was kind of stressful of like maintaining our relationship even outside of you know working hours. Um when I came home, I was still in work mode, I was still like mom mode, but I was never really life mode. So we have tried to like make where Friday nights are our date nights, and we just connect, we try not to talk about work, but it gets really hard because that's what our lives are all about. Um but finding ways where we can like just be together and appreciate each other and value what the other one brings to the table is what we're like working on. Because if you let that go and you then it's like, well, why are you doing that? You know, like we're building this, so our families and like our Are in a better spot. But if we don't focus on that, then why are we even, you know, doing what we're doing?

Reshma Vadlamudi 22:06

One lesson you have learned about communication with the spouse.

Alex Morgan 22:10

If you have not figured out what your love language is, do that first. So I feel like that has helped with me anderson's communication of like how do we each understand how the other one wants to be like loved and communicated with. So like my love language is um uh words of affirmation. So when he starts off a count conversation with like complimenting me or making me feel like he notices me, is when then I can have a more hard conversation with him. His love language is um physical touch. So when I know that I want to have a hard conversation with him, it's usually like I'll give him a massage first, I'll rub it, like rub his feet, um, and then like then leap into like having a hard conversation. Um so it's like understanding what the other person like needs to feel safe in that like in the relationship and in the environment to like have a hard conversation. That's what has worked for us.

Reshma Vadlamudi 23:18

Do you set any like boundaries between like I mean uh with the business?

Alex Morgan 23:24

We do not, but I agree that that does probably need to happen. Um we had a friend when we were first starting building out Jason Cali, and he warned us that he was like, you are going to hate each other. Now, is that the best advice? No, but it made us realize that we were gonna have some extremely hard times that we were gonna have to figure out what those boundaries were that we didn't hate each other. Um so I would say the boundary that we've been working on is figuring out like what days are we not physically working. Because right now I have been working seven days a week for the past eight months, and that's not um sustainable, you know, for our marriage, for for the kids, even for the business itself. Like if I'm constantly working seven days a week, then I can't properly delegate where other people can then do their jobs properly because I'm fixing everyone else's mistakes. Um having days off that are consistent, I feel like are is like our current boundary that we're trying to work on. Like right now, I'm trying to make Sundays where I'm not working and being strict with myself. I'm like, okay, I want to go in and check right now, make sure that it's running properly. I have to know myself, I have to tell myself, no, we're not doing that because that's we're setting boundaries for ourselves, we're not necessarily setting them for other people. It's like, okay, that boundary within myself is that I'm not gonna go into work because I know that my family needs me to be present, you know. So the past couple weeks I have been good with my boundary within myself. Um, but yeah, it's like a work in progress, you know. Like eventually I would love to have the whole weekend off. Um, and then maybe one day during the week. So it's like I'm only working four days. Um, so yeah, but it's like baby steps.

Reshma Vadlamudi 25:29

Yeah, what are the biggest advantages of working with your spouse?

Alex Morgan 25:34

The teamwork aspect for sure, because no one can do it all. Um, he has certain great qualities that I don't I am not a numbers person, I am not good with managing finances. Um, my creative brain is amazing, and I will be very proud of myself and will admit that. His brain doesn't work that same way. So, like knowing that he's really good at certain things and I'm really good at certain things and being able to work together. So, because if I was just doing it by myself, I wouldn't be able to do it. Um, and then appreciating that like connection between the two of us, and then setting certain boundaries that like okay, I'm not gonna step over onto his his lane, and I expect that same thing of him setting setting it up within himself, like I'm not gonna step over into her lane because that's her zone of genius, and that's his zone of genius, and how do we work together to make sure that it's all flowing together?