S1E1: OVERTHINKING WITH STEPH // CASSIE BROWN

STEPH: [00:00:00] INTRO: Do you have trouble turning off your brain meat at night? I invite you to take a break from your thoughts and listen to ours for a while. This is overthinking with Steph.

INTRO SONG: “Quit overthinkin’ alone… overthinking with Steph is better. We’re overthinkin’ together!” Steph: “That was stupid. Let’s come up with a whole new intro.” Mallory: “ughhhh Steph!!!”

STEPH: Oh, the joys of entrepreneurship. It's something that keeps me up at night. You know, it's very glamorous, the life we lead, Cassie. 

CASSIE: [00:00:29] It's is very, very true. The craziness of entrepreneurship.

STEPH: [00:00:34] So Cassie and I were sitting here after recording, just talking, and I'm like, we should be recording this because this is what is on our minds at all times, even when I'm sleeping. I am having dreams about work and I wake up with nail prints sometimes in my hand because I make fists when I sleep and I'm, like, doing things wrong even in my sleep. It's annoying. 

CASSIE: [00:01:03] Yeah. Yeah. I mean, it plagues me like it's all I think about day and night. I mean, for sure. And I feel like entrepreneurs, I mean, there's, there's this glory around being an entrepreneur. Like there's, you know, all these dreams and everyone wants to be one. Everyone wants to be an entrepreneur and start their own business and do this. People dream about it and you know, they dream about it because they want money, and success, and [the] fame that a lot of these entrepreneurs are getting nowadays.

I mean, the Adam Newman's of We Work and you see, you know, Elon Musk and Zuckerberg, and you're seeing these people who you fantasize about being. These rich and successful entrepreneurs, but truthfully, 80% of entrepreneurs that start a business, they don't do it for the money or the success or the fame. They do it because they want freedom. And I know that, like for me, when I started my business, I hated the nine to five.

STEPH: [00:01:59] Yeah! The cubicles, the office being stuck and tied to something and working for someone. Telling you what to do. I was so desperate when I quit my job to just get out. I didn't care if I made what I made at at Hurley. It didn't matter. 

CASSIE: [00:02:14] Didn't matter. Freedom. 

STEPH: [00:02:15] Freedom is what it's about. Not any type of fame and fortune. It's getting out and doing your own thing, making your own schedule, traveling and being able to meet new people and form these relationships that I felt like I couldn't do when I was stuck. 

CASSIE: [00:02:30] Exactly. And that that is what entrepreneurship really is. And when you talk about freedom, I mean you're bound by your own rules, you know? So it's, it's more what you know, you make your schedule every day. So therefore I wake up excited to do that, if that makes sense. 

STEPH: [00:02:49] I could work 18 hours a day and it goes by like that and wake up the next morning and am excited to do that next 18 hour day, you know? But it is a lonely, lonely life sometimes. 

CASSIE: [00:03:02] Oh, without a doubt. Yeah. It's the loneliest, and especially, I mean, as you know, you're building a team right now. When I started my company, it was literally just me, by myself. 

STEPH: [00:03:13] Yeah when I met you, you worked out of a little house by SMU, right? With what? Two, three, desks, maybe? 

CASSIE: [00:03:21] No, literally like, that's it. It was me and like two others, that was six years ago. 

STEPH: [00:03:29] I remember walking into Smart City Apartment Locating and I was like, this is the cutest little thing. And now I walk in and it's...

CASSIE: [00:03:38] Yeah, it’s massive. 500 square foot office is what we had six years ago, and literally next week we're moving to a 15,000 square foot office 

STEPH: [00:03:47] and casually having a baby. You're tackling a lot, but that's a massive place. How many people do you have working with you now?

CASSIE: [00:03:53] You know, I have 180 people right now.

STEPH: [00:03:56] I feel like I've done your head shots every year for the past couple of years and it went from like “let's take five head shots” to “Oh, Steph, can you shoot 200 people now?” It was overnight almost. How did you do that and what are you, crazy?!

CASSIE: [00:04:12] I'm literally insane. It feels like it some days, honestly. If I could tell somebody, if I could go back and tell myself, I'd be like “Hey, probably don't grow past like 120 people.” But now I'm committed to the growth. I'm here for it now. And I want to talk about your business too, cause it's grown wildly in the last two years since I've known you.

You know, going from just a couple of people, when you find something, when you find that something that actually works, it's like, okay, well now I need to work on something else. So I'm going to write down what this job should be, and here's the job description and here's, you know, here's the instruction manual.

You know what I mean? And now here's the process and the systems, and boom, now you do this job and I'm going to focus on something else. And, and honestly. It keeps going. Like every time that I would hire someone, it would be like, okay, now you do this, which is what I was doing before, and now I'm going to step up and do something a little bit differently.

And now I've got to hire people to manage that. And so, you know, now when you look at, when you look at my team, I'm managing the managers who manage managers, who manage managers, who manage the team. So it's a different world and it is a lonely, lonely place.

STEPH: [00:05:25] You think about it, when you're trusting someone to do something and it's your baby. This is your baby. You built this from nothing, and that's how I feel about my career too. Then you hire these people that you trust, who sometimes end up being your friends, because you trust your friends, right? Without a doubt. You think that's a great decision at the time. I get to work with all of my friends. I trust them, but it gets a little nutty sometimes and can get very, um, it hits close to home. 

CASSIE: [00:05:52] So you talked about two different things, and I want to touch on both of them cause they're both critical. So mixing work with friends to me, I will never, ever, ever do it again. Yeah, I won't ever do it again.

I won't. Even like starting businesses, anything like that, working with friends is an absolute nightmare because people think they can compartmentalize. I can compartmentalize all day long, but you can't.

STEPH: No one can do it as good as you and I.

CASSIE: The truth is, but you mentioned trust, and I want to talk about that separately because that's an entirely different thing.

Trust is critical in business, the people that I've hired and the people that I surround myself with and the people in my company, I trust to the moon and back. I'm telling you, and I have to, I have to trust them because I need to give them the freedom and the autonomy to make decisions.

And to trust that they're doing the right thing. And so I don't hire people based on their experience or their skill set. I hire people on the potential of their skill set, and I hire people on culture, because I know that if you're a good human and you live by our core values, and you believe in the things that I believe in, then I know that you're going to make good decisions for this company.

And if you don't, that's okay. Because I'm going to coach you through that and we're going to talk about it and my leadership team, I expect them to coach their people through that because it's not about making mistakes, because mistakes are okay and they happen. It's owning those mistakes and having responsibility for them and saying, “Hey, I screwed up.”

This is what I learned from it, and here I'm going to go improve myself, or I'm going to go focus on some business books or whatever that is to, to make sure I don't make these mistakes again. I would say probably the biggest mistake I've ever made in business was working with my friends.

STEPH: [00:07:39] Yeah. How did that change things for your business when certain things fell through with those friendships? 

CASSIE: [00:07:51] I mean, it was, it was crazy. The business was growing so fast and I was naive. I was young. I didn't know anything. Shit, I still don't know anything. But, I was trying to figure things out.

You know, I read 60 books in a year trying to figure out what's next, how do I do this? And, you know, I would talk to the people who I thought were my friends who also worked for me, and it was such a conflict of interest that I was like, Hey, I should do this and this and this, and what if I changed the role to be this?

And they're like, “that's my livelihood, my livelihood. You can't change that role.” Oh shit. So I had no one to talk to. I hired all my friends and my wife, love her to death, but she didn't want to deal with me. So it was a lonely place to be because who can I kick these ideas around with?

Who can I talk to? Because I know that I'm not right. I don't know anything. I mean, this is my first time doing any of this. I gotta make sure I make the right decisions for this business and for the people in it, but I can't talk to the people inside the business because it effected them. and there were decisions that effected them. It was a lonely place to be. It's still a lonely place to be, man. 

STEPH: [00:09:02] Kayla was mentioning how she can't imagine how I function because I have, honestly, I come home to my dog and my brain. And it's, it is exhausting. And I was telling you earlier, like trying to rally and go out with people while having social anxiety to the max, which most people wouldn't know about me, but then being completely exhausted from talking to myself in my head and going through all of these situations because I don't have anyone to talk to or I've talked to the wrong people, like you said before, and it comes back to bite me in the butt.

CASSIE: [00:09:37] Yeah. But, and you're growing so fast too. I mean, what's your team look like now? 

STEPH: [00:09:41]I mean, there's probably between 10 and 15 of us kind of scattered around the US depending on where the job is. I think that there was a time where I was just terrified of growing and wouldn't trust people with what I could do because there is a point where people are hiring me based off of the experience with me, and that's the case with LGBTQ weddings. So I couldn't just bring someone else on to be me. So that wedding thing, I'm a lone wolf.

The corporate side of things, it's a little bit easier. I match my clients based off of who I think they'll work well with to tell the story. So it's, it's growing. But there was a time where I just stayed very stagnant because I wouldn't trust anyone. 

CASSIE: [00:10:36] And that trust liberates you, and you don't realize it in the beginning, especially as an entrepreneur. If you're doing your own thing and you're like, well, this has worked for so long. If I change it, the risk is to lose everything.

You know, to trust is to lose everything. But it's actually the opposite to trust is to gain everything, you know? And, yeah, there's people who are going to burn you, without a doubt, you're going to make mistakes. You're going to mess up with clients, stuff that people are gonna mess up. That's the nature of human beings.

But the more honest and open you can be and the more you trust people and the more you start bringing on the right people, that is what scales a business. That's what makes you grow. And I think bringing on the people that have been following my work for a while too, I think that is very important because then they see the vision and it becomes real to them and they can emulate that. 

STEPH: [00:11:24] Exactly. Yeah. Yeah. So it's been a wild ride. I'll be celebrating 10 years in February. It's amazing. 

CASSIE: [00:11:31] Congrats. 

STEPH: [00:11:31] Thanks. I'm just, I'm tired. I'm just tired and I don't even, I don't know how you actually function because I have a team of, you know, 10. You're with your people all the time. Mine are kind of scattered about. I'm tired and I'm lonely. Burnout is so, so real. 

CASSIE: [00:11:50] Yeah. The thing is, is that most entrepreneurs, because what drives them is this sense of freedom. Again, 80%. 20% are driven by all the things that I don't give a fuck about, which is success and fame and money and those things.

STEPH: [00:12:05] The fame. Sorry, I cut you off. No, like when I went viral. I mean, you don't make something go viral and you don't stop it from going viral. It just takes off. People like what they like, and they want to share it. I didn't ask for any type of fame or following, but when it happens, you just got to gotta go with it and make the best of it.

But it's terrifying to be running a business and a brand with my name in it, because you say the wrong thing or you offend the wrong person and your whole business crumbles, but it's also my name, you know. I've over-thought that many a time.

CASSIE: [00:12:49] The podcast is called Overthinking. That's normal though. That's scary. And most entrepreneurs do have some sort of, and this is something that people just don't talk about, but some sort of imbalance when it comes to, you know, hypomania or bipolar or ADHD. You know they call ADHD and bipolar, the CEO disease. I mean, because it comes with these highs of highs and lows of lows.

STEPH: Do you take medication for it?

CASSIE: Yes, I do. I do. I definitely take Adderall. I have to, to be able to focus cause I'm ADHD to the max.

STEPH: [00:13:27] I take Adderall XR. So I switched over to the extended release. It's not, it does not work. It does not work or it's not working. 

CASSIE: [00:13:32] I only take it like once a week and only when I hyper work, for literally paperwork, spreadsheets, all of that stuff.

I work in cycles and I don't know if this is similar to you, and I've talked to a lot of entrepreneurs who go through this, but I'll have a couple months of, of just 80 hour work weeks. Like nuts where I am working around the clock.

Nothing can stop me. I'm on top of the world and then I'll have three months of, I'm struggling to get out of bed because I hate myself. I have not achieved enough. I feel so guilty for taking a day off work, 

STEPH: [00:14:08] It’s three months of beating yourself up.

CASSIE: [00:14:09] literal guilt.

STEPH: [00:14:10] even though you just worked your ass off for three months.

CASSIE: [00:14:14] Yes, I, there are days where I literally look at Kayla and I'm like, “I am nothing. I am insignificant. I am a piece of crap for not getting up and going to work today. I have not achieved anything. I have nothing to show.”

And she literally looks at me and she's like, “you're an idiot.”

“I love you. You're an idiot. You have a company of 180 people. We do $20 million a year in revenue. We're scaling at a rate of 50% to 80% a year. You're over your growth average.” I mean, we're growing like a weed and still, I don't feel like I've done enough. 

STEPH: [00:14:50] Is that helpful in that moment? What do you need in that moment when you were at your lowest. What helps? Does hearing that help? Her saying, dude, you're an idiot. Cause I love Kayla and I wish someone would say that to me, but it's so real. I love that about her. I wonder, I know exactly what I need in every single moment and having to be calculated about who I go to for that.

Sometimes I just need a hug. How sad is that though? I don't have physical touch on the regular. Yeah, I have Rusty. Great snuggler. 

CASSIE: [00:15:26] I'm sure there are a lot of girls out there who would give you some physical touch. 

STEPH: [00:15:29] But then that gets complicated. Right? Then you have to calculate your cuddling and like make sure…

CASSIE: [00:15:36] Like, that is the most business owner thing I think I have ever heard.

STEPH: [00:15:39] I'll be honest, like there are times that I'm like, I just want someone to hold me and watch your show. Because I won't watch a show by myself. I won't relax and watch a show.

CASSIE: I don’t think I see a TV and I’m literally here right now in your loft, and there's no TV.

STEPH: I cannot sit and allow myself to. I have to be reading a book about being an entrepreneur or growing or self care. I can't just sit and unplug unless someone is there with me. And then that complicates things because I mean, being a lesbian, you know, it's a very close knit community. You know, so calculated cuddling.

But the loneliness is, it can be torture. I also really like being by myself. So it's this constant tug of war between wanting to be completely private and not completely unplug from social media, but get a pager again, and throw my phone out the window.

I would love that so much. But then there's, “Oh, I got to run my business and I have to be visible and vocal for the people who cannot.” And then it's like this constant war inside of me. That’s where I'm at, I'm so tired. 

CASSIE: [00:16:58] What is your network look like for entrepreneurs? Do you know a lot of other people who are kind of doing what you're doing in this space or, working for themselves or growing businesses?

STEPH: [00:17:07] My favorite thing is when you and I, and Lacey and Kat get together for our meeting of the minds, and we go to Local and we have the seven course meal and we talk about everything. Work, how lonely it can be. I do look forward to that. I know you guys are doing things a little bit differently than me.

Social media looks different for all of you, but those are important to me. Those times are important and I dread a lot of social things and I do not dread spending time with you guys. There are some people that I can call who get it, but it almost seems exhausting to then talk about it when I've already talked about it in my head.

I just want to sit sometimes. 

CASSIE: [00:17:59] Well, sometimes it's nice to know that there's other people who are going through the same thing, you know? You know, I thought I was alone for the longest time in this. There's so many podcasts, so many things that talk about growing a business and how wonderful it is but no one really talks about the darkness of it. Not the hard parts, there are hard parts about growing a business, but the internal mental struggle of never feeling like you've done enough. It's that anxious achievement and it's usually comes from kind of a dark and haunted past.

STEPH: Because you know, it comes from something probably that's personal, in your personal life, that is effecting your business.

STEPH: [00:18:40] Definitely. And if you don't do the work for yourself, personally, it's going to be that way constantly. How do I have time to invest in myself? I'm trying to run this business. Right? It's exhausting. I was reading a book by Mel Robbins yesterday. Have you read any of her stuff?

Talking about busy-ness and being busy for the sake of being busy. It stems from needing to feel valued. That's what I can relate to so much. When you feel like you're in high demand, or you're busy or whatever, then you're viewed as important. People need me, right?

I have nothing else to say about that, but it's true. It's so true. 

CASSIE: [00:19:29] I think that, for me, surprisingly, I consider myself lazy.I know my wife, literally, she's shaking her head right now because she's like, you're not lazy, you know? But I like to consider myself lazy sometimes, and I think entrepreneurs should be a little bit lazy because they think about the easiest way to get from point A to point B. The easiest way to get to a solution.

So, I'm a big problem solver and all I do is think about is “well, what's the easiest way to get from here to there?” Right? So it forces me to step back and stop being busy to sit and think and say, what are the few things that get to the results quicker.

So, instead of focusing on those busy things, I step back and I say, okay, I'm focusing on this, this, and this and this. Truthfully, I could pay somebody else to do those things. And if I pay somebody else to do those things, what are the biggest, most impactful things that I could be doing today to drive the business forward?

So every single morning when I wake up, I look at that because I get into the realm of busy-ness as well, because then I'm just busy. I'm busy, I'm doing stuff. And then when I really, really look and analyze what I'm doing all day, none of those things actually push the business forward. And that is critical.

So looking at that, I feel like that when you're looking at busy-ness versus productivity, because they are two different things, you have to analyze the day and say, okay, I'm going to push towards that, but it's not always easy to do. I think that we easily slide back into the realm of busy-ness in order to feel value and to feel like you were talking about, to feel that sense of recognition and being needed, but it’s the opposite.

STEPH: [00:21:13] Yeah. What are your friendships looking like now that, well, you've been successful in business since I've known you. This is a completely new level, I feel like for you. How how do friendships change and how you maybe have to be more selective? The reason I ask this is because a lot of my friends give me a hard time for being a bad texter. I mean, I am.

CASSIE: [00:21:47] you are a bad texter.

STEPH: [00:21:48] I'm a horrible texter. I also hate phone calls. I hate phone calls. With social media, have you ever dealt with, you probably haven’t dealt with this, but, if someone texts me or I step away from my phone for an hour, there will be texts and texts and texts and notifications. It's overwhelming, you know? But I still have to keep running my business, so I'll post something on social and then the texts keep coming, “I saw that you're posting on social and you're not getting back to me.”

I can't do that anymore. I might have to cut this whole part out of the podcast because I can't do needy friends. That stems back, going back to personal things, growing up, someone always needed something from me.

I was the source of my mom's joy and happiness, you know. I had to be the bubbly one who was on at all times and couldn't have any type of negative feeling. So now if someone needs something from me in any capacity, I'm almost just spent.

CASSIE: [00:22:49] Do you think your parents listen to this stuff? 

STEPH: [00:22:52] No. 

CASSIE: [00:22:53] You really don't think so? Secretly, you don't think they go and look? 

STEPH: [00:22:57] I would, I would completely doubt it. I came out when I was 24 and I don't think my dad has ever even talked about me being gay or addressed any of it. There are times like my mom will, I mean, I haven't talked with them since last year. I had to put up a few boundaries for my mental health and sanity, but, it's very exhausting. That part of it too, because I feel like for a decade I spent so much time and energy trying to get them to love me the way that I felt like I should be loved.

I finally had to come to terms with the fact that that's not going to happen. It's not going to happen. And now my energy has to be invested in me, you know? Going to therapy and, and all of that.

I know my mom, I've flown her out here a couple times. She saw my last loft and she cried because she had no idea that I was successful. I've been interviewed by fossil in the face of their campaign. I've been recognized on the California Senate floor.

They probably don't even know about it. 

CASSIE: [00:24:10] Wow. Yeah.

STEPH: [00:24:11] It's, it's very disappointing that religion could keep them from the person they brought into this world. 

CASSIE: [00:24:20] It's sad because they're really missing out on a good thing. 

STEPH: [00:24:24] I now know that before I would beat myself up cause I'm like, you know, if my parents can't even accept me, how am I supposed to even love myself? How someone else supposed to love me? Right? I just get used to beating myself up on the regular, it's almost like part of the schedule, you know? So to finally be taking care of myself. After 36 years of some extreme trauma and religious abuse. Yeah, I think that that does affect business.

CASSIE: [00:24:58] The personal side of things completely effects my business. I think it drives you to be more successful, because you don't have that safety net, and it drives you to achieve and achieve and achieve because that's satisfying a need that you didn't have a before.

STEPH: [00:25:16] Yeah, and, if you don't mind me asking, since we're talking about parents, do you feel like your parents were, were proud of you when they were alive? 

CASSIE: [00:25:30] So, I had a very interesting upbringing. I'll do the one minute run through. I was actually raised very, very wealthy. When I say very wealthy, I mean like lear jets, helicopters, bodyguards to school, limos.

So like freakishly wealthy like that. My father was in bonds before the internet. So they were able to take like really high rip offs of trades before the internet basically told you what the price of the stock was. So something happened with his company where the Wall Street Journal said something negative about his company and it basically tanked his company.

So they sued the wall street journal for the highest libel case in its time. It was like a $200 million case. It was unheard of. And all this crazy stuff happened. A warehouse full of files burned down. This pilot who had all this information died in a plane crash, like crazy, crazy shit happened.

Ultimately, my parents were spending millions and millions of dollars fighting this lawsuit, hoping to get this settlement, and they kept fighting, made some bad investments, fought some more, did all this stuff to where by the time I was 13 years old, lost everything. We were on food stamps.

So I went from extreme wealth to homelessness. Our house was foreclosed, the cars were repossessed, the boats were repossessed. The boats were repossessed. Everything that we had was gone. My father became a heroin addict. My mother became an alcoholic. I was forced to get a job at 14 to help support my family.

At that point, I had moved out at 16, took my brother with me. He also deals with some addiction issues, but I don't touch it. I don't even drink, because I have that in me because both of my parents are addicts. So both of my parents have passed now both from their addiction. And recently, my dad passed a year ago, but I hadn't spoken to him for two years. I mean, we could go deep into this, but my dad gave me drugs when I was 15 years old, he got me hooked on methamphetamines.

So I mean, just crazy shit. Like I don't do any drugs now. But he got me hooked on stuff, gave me weed, gave me pretty much everything. I had a really, really rough upbringing, but going from being very, very wealthy to very, very poor. I like nice things, but I am driven by frugality.

So it's this thing to achieve. It's very, very hard to achieve what my father achieved, you know? Because he achieved very much in his life and then lost everything. So the constant fear in my life is I'm going to be just like my parents, I'm going to lose everything and die alone. And that is where it gets really fucking dark.

That's where it gets deep and dark. And so when we talk about entrepreneurship and all that stuff, yes, I want my freedom. I want my dream. But I also don't want to lose everything and die alone from an addiction. And so I always talk to my, my wife and I'm like, Kayla, you know, if we're broke tomorrow, do you love me still?

And she's like, of course. And, it doesn't really have anything to do with money, it just has to do with losing everything that I have. Those fears drive my success. And so there's a lot of guilt that comes when I take a day off work. I have no problem working 60, 70, 80 hour weeks, and when I take a day off… I just took one off a couple of, couple of weeks ago.

I took a day off, like a Thursday.

STEPH: [00:29:00] did you feel guilty? 

CASSIE: [00:29:01] Oh my God, I felt so guilty. It just, it was just so awful. 

STEPH: [00:29:05] Did you read teen fantasy books?

CASSIE: [00:29:09] Teen Fantasy books? Yes. Um, no! I hung out with Kayla all day cause we were, we're about to not have time for us, so I'm like trying to spend as much time as possible.

Anyways, we just went down a dark rabbit hole. But, I think that our, our past lives like, how we're raised, do they have a part in that? Absolutely. Have you heard of the grit scale? 

STEPH: [00:29:31] No. 

CASSIE: [00:29:31] So grit is like how hard you'll keep going.

How hard you'll persevere. Even in the face of obstacles, right? Sorry, not as a grit scale. You either have grit or you don't have grit, right? When you look at how someone was brought up, 10 being having the most opportunities in the world, and zero, having no opportunities, zero is like homeless, orphan, the worst of the worst.

The people who have the most success are the threes and the sevens, because sevens weren't handed everything, whereas tens were handed everything. Then the threes had a really hard life, but not the hardest. And then the fives and the zeros and the tens do the worst in success and in business.

So it's really interesting to look at that and see where I would put myself on it. I would say I was probably a three or a four, because I had a really rough upbringing. I know people who had a pretty good upbringing, upper middle class sevens ,not handed everything, but they're also extremely successful as well.

So anyways, dark rabbit hole. 

STEPH: [00:30:35] So what keeps you up at night when you are laying in bed? What's that one thing that haunts you? 

CASSIE: [00:30:44] The fear of losing everything. It's not the financial aspect of it, because I don't care about money because I know my skill set is very unique and I can go start a company again.

So, it's not the money aspect. It's my wife, my kid. What if my kid hates me? What if? What if I've done something wrong or I work too much and they hate me? What if I’m losing friendships, just losing everything. You know, and ending up alone, that's why I want like 19 kids.

Not really, my poor wife's body, 

STEPH: [00:31:18] Kayla just passed out in the corner. 

CASSIE: [00:31:20] Kayla was like, no, I'm not having 19 kids. I want a big family because I didn't really have one. I didn't really have that. And I want inclusivity and I want love and I want to talk about the real things that are going on and I don't want to just shove everything under a rug and let's pretend like nothing exists.

Like especially when it comes to religion. I was fortunate in the way that when, when it came to religion, my parents put all the books in front of me, the Bible, the Qur'an, they literally put everything in front of me and said, you choose. You know, you choose what you want to be. 

STEPH: [00:31:48] Picking bits and pieces from each one, as long as it is teaching someone how to love and be a better person. I'm for it.

CASSIE: [00:31:55] Create your own reality. Your own spirituality. And the people around you, Steph, you inspire me. Every time I come over and talk to you, I'm so inspired by what you're doing and the people that you're helping. I don't think you realize how much of an impact you're having on the people around you, not just me.

STEPH: [00:32:13] So I'm going to have my single tear come out once every two months.

CASSIE: Calculated tear is happening now.

STEPH: I Really appreciate that. I think that It's important to have these conversations and to let people in. And I don't do that very often. You know that, we'd been friends for a good amount of time. And it's hard for me.

It's hard for me to let people in, but also I think about being alone for the rest of my life and am I going to be alone for the rest of my life? And did I do that to myself? 

CASSIE: [00:32:45] Does that keep you up at night? 

STEPH: [00:32:46] Oh yeah. 

CASSIE: [00:32:47] It's kinda the same thing.

STEPH: [00:32:47] It's everything is a little like a trigger that reminds me that I'm alone.

I can keep myself busy and distracted and work, but then the second a tornado hits or we're having weather, I have no one. I'm like, it's my family even going to check on me. We just had nine tornadoes in Dallas. I didn't hear one thing and I was talking to my therapist about this, 

CASSIE: [00:33:11] Do they even know if you're alive?

STEPH: [00:33:15] I mean, maybe they'll check social media and like maybe my sister? I don't know. I have no idea. If they even know. 

CASSIE: [00:33:23] It's so hard because you live that fear every day, and you have so many people who aspire to be you and who want to know you because of where you're at and how much success you've had, especially in the lesbian community.

And yet you still feel this deep fear of being alone. 

STEPH: [00:33:41] Yep. That's true. I do believe you need to work on yourself and love yourself and put in that time and energy. There's a point where I'm like, I'm 36 and what I long for, that connection, is so hard to have in my life, even though it seems so easy for a lot of people.

I’ve watched that happen, and I’ve watched people meet and they fall in love. And then I document it, and it's great. I love those love stories, but there is a time where I'm like, will that ever be me? Do I want that? I've really changed my view on marriage and a lot of things that really held me back in the past from connecting.

Connecting is hard. But working on it, working on it. And your wife was just looking at her belly in the mirror and it was the cutest thing. That's why I was distracted. I couldn't even get my thought out. This is adorable!

Thank you so much for being on here, and just being you. Being my friend, being willing to get real about stuff that's hard to talk about sometimes.

CASSIE: [00:34:50] And I appreciate you creating this opportunity to be real. And I hope that somebody listens to it and wants to, you know, become an entrepreneur or somebody who is dealing with this, is just starting their own business and you know, understands that they're not alone in this, this whole thing.

And, you know, I appreciate you having the medium to be able to kind of share that with the world and know that people aren't alone.

STEPH: [00:35:15] Thanks for hanging out with my brain. 

CASSIE: [00:35:16] Thanks homie. I appreciate you.

STEPH: I love you and I will talk with you soon.

CASSIE: So let's overthink this.

STEPH: [00:35:21] OUTRO: Well, Hey, thanks for Overthinking With Steph. Can't wait to hear from you on the social. So make your way over to @Stephspodcast on Twitter, and tell me your thoughts. Catch the breakdown on Patreon where we get into the nitty gritty, and overthink the conversations in this episode. Till next time, keep creating scenarios that will never actually happen and live YOUR ONE DAMN LIFE. 

OUTRO SONG: “Don’t you hate it when you wake up first thing in the morning? Mind is stirring. It’s a wreck. Overthinkin’ with Steph! Cool your jets. Go to bed. Get out of your head!”