Lady-Brains With Anna Mackenzie & Cait Judd

Josh: The Daily Talk Show. It's The Daily Talk Show, episode 536. Special guests on the show, Anna McKenzie and Caitlin Judd, also known as Kate Judd.

Caitlin: Yes.

Harry: Kate Judd.

Tommy: No relation to Kate Judd.

Caitlin: We rehearsed this earlier. No relation.

Anna: Or to be determined.

Tommy: Mr. Chris.

Josh: And so you have LadyBrains and Ladyland. Ladyland being the podcast.

Caitlin: We do.

Tommy: LadyBrains being the business. We were just having a conversation before and we wanted to save it for— it's like there is What is the difference? I mean, one is a podcast, but it's—

Caitlin: Yeah, great question.

Tommy: Thanks. We heard this morning on radio someone asked a great question, what they determined is a great question, but it's just time to search the answer.

Caitlin: It's time to tell the truth. Yeah. Well, so yeah, so LadyBrains is the business. So we're a club for entrepreneurial women in Melbourne, Sydney, New York. Ladyland is the podcast arm of the business. And really we have created a bit of a monster. We probably should have called the podcast LadyBrains, but the reason we didn't simply was because there was already a show in America that was like 3 Texan women chatting about nothing called the LadyBrains Podcast.

Anna: Sure.

Josh: I think that's a good, like, it's good to make sure that you are the only one. Like you see podcasts that come out and there's already one that exists. I'm like, what are you doing?

Tommy: Hard to do now.

Anna: It is hard.

Josh: Yeah.

Caitlin: Well, there is now another Ladyland.

Anna: That's the clincher. So we went out with Ladyland and then someone came out with a Ladyland podcast.

Tommy: How much have you looked into exactly what address they're living at?

Caitlin: Well, funny, they're also in Texas, so I don't know what that's about.

Anna: What's going on over there?

Josh: Would the Nextdoor app tell you that?

Anna: Nextdoor.

Caitlin: Could look into it.

Josh: And so you, um, You've done a bunch of interviews recently in New York. Was that a planned trip where you were just going there?

Tommy: Or pure business write-off?

Anna: Yeah, no, not quite. I had a wedding to attend and then we somehow turned it into a bit of a little cheeky business trip. Yeah, yeah, yeah, yeah.

Caitlin: Well, yeah, so she had a wedding to attend and then I decided, oh, I'll quit my job. So I quit my job and then we went to New York for a month and we landed a few awesome interviews like CJ. Henry, who was amazing.

Josh: So good.

Caitlin: And then, yeah, we just kind of gallivanted around, went out to the Hamptons, went upstate, recorded a whole bunch of content, met a whole bunch of people, and then came home, which was awesome.

Tommy: There's nothing more liberating than quitting your job and then going on this sort of unique experience and feeling like it's new life. And then the step back into reality.

Caitlin: Well, yeah.

Tommy: I think it's just even just stepping back into your your normal life or what you call life back home.

Caitlin: Yeah.

Tommy: Leaving your job, where were you before?

Caitlin: I was at Mecca.

Tommy: Okay. Yeah. And so the venture, you know, going into any venture, business partners, what was that relationship? Was it a friendship or was it a business, purely sort of business first and then you became besties?

Anna: Yeah. So Anna and I, we went to school together, so we've known each other for a very long time. What, we're 12?

Josh: Yeah.

Anna: So yeah, it started out as a friendship. And, um, and, you know, we've had a really strong friendship over the years. We obviously went our separate ways to, you know, go and pursue other interests and work in different places, um, and then came back together. And we always wanted to start a business together, like, that was just kind of the dream, you know. And it never kind of worked, uh, up until, up until—

Caitlin: well, we had many, we had ideas, many failed business ideas. Like, I think the funniest one that I always, like, refer back to is we would 21, and we were actually sitting at a restaurant on Victoria Street, and we were like, oh my God, there's a gap in the market for a divorcee dating app, like a divorcee dating website.

Anna: So it was, it was like, it was the dating, but also like, where can you find like a babysitter if you have kids? Where can you like— it was a whole resource hub for divorcees, right? We're 20, we weren't even probably even 21 years old.

Caitlin: I think we should check, we've still got the domain name, nevertolate.com.

Anna: Yeah, yeah, or second round offer as well. This is why 'Hey, GoDaddy, so much money.' Well, this is the thing.

Harry: What about Ivegotkids.com?

Tommy: So you just know that you've got kids if you're dating.

Anna: Great.

Tommy: Love that. Check if that's around. GoDaddy is probably the best provider.

Josh: Ivegotkids.com.

Tommy: Ivegotkids.com. So it's like the awkward conversation as a single person. Not that I'm pointing to myself. I'm not single.

Anna: I have kids.

Tommy: But I could imagine the anxieties around, I've got kids and I want to date. And so how do you like dating a 22-year-old on Tinder? It's like, do they want to be dating someone who has kids? I don't know. So it's just leading with it. You bring your kids, it could be double date.

Caitlin: I don't know, I thought it was a family vacay.

Tommy: This will be in the language of businesses that didn't work.

Caitlin: That was one of the ones that definitely did not work.

Anna: Yeah, the other one.

Josh: How did you know that didn't work?

Anna: Oh well, I mean, it could.

Caitlin: Well, to be fair, we, well, we weren't, we didn't really understand the target customer because we were 21 and single at the time. We purchased the domain name. I think we did a bit of research and then we gave up and went on to the next one.

Anna: So the next one was like a bike sharing app, which has been really successful in Melbourne.

Josh: Well, Tommy did the O-Bike fishing video that went viral where it was, I think I fished them out of the, yeah, I think I'm responsible for their demise in Melbourne.

Anna: Okay.

Josh: Yeah. It's something he hangs his hat on.

Harry: Yeah.

Josh: And he loves getting business. Was it Lime scooters? You were sliding into their DMs. Anytime there's sort of a share type thing, he's like, hey, I'm the, the O-Bike guy, I'm sort of available.

Tommy: But sharing your bike, but sharing your bike is like you're not using it. Who else can use this thing?

Anna: Correct.

Harry: Yes.

Tommy: That's great.

Anna: Yeah, that makes sense.

Josh: I get that, but I feel like I've got a bike that would be— I'm not in a position. I don't want to sell the bike.

Anna: You want to rent it out.

Josh: Yeah. And so that would be useful.

Caitlin: Side note, I read an article about a really interesting business that has just come to Australia, which like has raised lots of money in the US. Airbnb for pools.

Josh: Oh, that's interesting.

Tommy: Borrow somebody's pool for the day.

Caitlin: Oh yeah, you pay a daily rate and it depends on how, like, whether it's a mansion-type pool or just a normal pool, and you can pool share.

Josh: Oh, that's great. I mean, if you can afford a pool, I don't know if you need to.

Anna: Do you want to rent?

Tommy: Yeah, but I guess like, there's a lot of Bulgarians stretching themselves to get a pool.

Josh: Oh yeah, that's true.

Anna: Yeah, live the lifestyle. Maybe you need to rent it out a few days.

Tommy: Are you a bogan who just got a pool? Have you pushed your debt way up and need to pay it back?

Josh: It's even like when you have, because I had a pool when I was a kid and it was almost like, you're a bogan. Yeah, definitely a bogan. But you already had your friends asking. I remember people would rock up and they'd be like, oh, hey, how you going? And they had their fucking towel.

Anna: They hadn't even called.

Caitlin: Yeah, they're ready.

Josh: 100% ready.

Tommy: My mate did a video, Ryan John, he went around, found on Google like where the pools were, went and asked in summer, was like, can I jump in your pool? Asked enough people and got one.

Caitlin: That's how this guy started the business. He went on Google Earth and he searched all the pools in the area. I think it was in LA. I mean, it's pretty smart. Yeah.

Josh: Well, I mean, an app idea that I had the other day, we were at the airport and I have status. Tommy doesn't, whatever. No big deal. I'm about to lose it anyway.

Anna: Oh, don't, don't lose it.

Josh: Get on a plane.

Tommy: How are they feeling sorry for him now?

Josh: I'm still the loser with no status.

Anna: He's the bogan with no pull.

Josh: It's hard. It's actually harder to get rid of it.

Tommy: When you pay for a pull on your credit card, it usually puts you into status.

Caitlin: Yes.

Josh: But they, and so I could get Mr. 97 into the lounge. Yeah. But we, with gold, you only get one extra person. And so what are we going to do with Tommy? And just, it just so happens I was getting ready to just hustle and say, hey, can you just let us in? Like we're all wearing the Daily Talk Show hoodies. We're part of a crew. You want to just let us in? And we've done that at Sydney Airport and it's been successful.

Tommy: Yeah, right.

Caitlin: Yeah.

Tommy: International is a bit harder.

Josh: International is harder because it was Emirates or whatever. It was like a co-chair, whatever. Tommy then waits out the front and just starts talking to a guy who's lining up to go into the lounge.

Tommy: It was perfect timing. I sort of sat back and Mr. 97 was watching me thinking, what are you doing? I saw one guy walking towards us and I was like, fuck, this is, this could be my shot. And as he got closer, I was like, hey mate. Hey, I was like, are you going in here? And he's like, yeah, you creep. I said, oh, where are you flying to? And yeah, he got a bit weird and he's going to Melbourne. He was on the same flight as me. I was like, oh my God. I said, my mate's got status, he can't get me in. Would you mind if I came with you? Yeah, sure.

Josh: But then there was a question of when he— when we walked in, there was a moment where we're like, oh, do you want to come sit with us? Like, I was like, I'm at work.

Anna: Champagne together.

Tommy: I said, yeah, feel free to come.

Josh: He works at Microsoft. Seem like an interesting dude.

Anna: Yeah, I actually think more people should do that. And so the idea is that get a plus one.

Caitlin: Yeah.

Anna: And if you— if they're travelling solo, just kind of go up and—

Josh: yeah, let's see.

Anna: I mean, the worst thing, like, yeah, but— or just stand.

Tommy: You can use this.

Josh: So this is the idea though. There's an extra layer. So it's called Karma. And so it's based on, like, I don't have Qantas, but I've got Virgin. And so it's like, I do it for someone so then when I'm on a Qantas flight, I can then get that. And so it's a bit of karma.

Anna: So it's a bit of litmus.

Tommy: Yeah, yeah, yeah. We did find one problem. Terms and conditions of the status thing is like, you can't do that.

Caitlin: What about, how do you monetize that if it's a karma situation?

Josh: There's a lot of businesses that haven't.

Tommy: Yeah, I mean, some have raised millions with no business model behind them. Yeah, it happens. Anyway, so we're talking about, we're talking about business. Ideas that haven't gone anywhere. And I think that's the easy part, right? Ideas are easy. Execution is totally another thing. And for you, what you've created is working. The podcast is growing and it's got a great audience and the business. So why did you land on this one?

Harry: Yeah.

Anna: So after a few, you know, start stops with ideas, we finally landed on LadyBrains and I I think, you know, there were originally 3 of us in the beginning. Um, Maeve was our, you know, co-founder as well. And the 3 of us just identified this— the fact that we all wanted a network that we could tap into, um, and we wanted to be able to connect with, you know, other women that were starting up businesses or trying to scale a business. Um, and I think, you know, I was working for myself at the time, you know, Anna, again, she wanted to expand her network as well. And so we just— it was it was kind of an easier one to start because we had friends and our friends also wanted to do kind of like a dinner series or a dinner club. And so we started running these supper clubs and that was so easy for us to do. I mean, like we go to dinner anyway, but let's just kind of formalise it, put a little bit of structure around it.

Josh: Was it like tickets?

Anna: It's like a bit of a— Yeah, we didn't start selling tickets.

Josh: Splitting the bill, you don't have to worry about.

Anna: And it's so much easier, right? It's like, yeah, pay us. Come along and, you know, that the genesis was, you know, with these supper clubs and it grew from there because we started inviting founders into these dinners. And so you'd have the opportunity to sit at the table and, you know, talk to and ask questions of a founder who was building, you know, a big business like that's, that's quite unique to be able to ask any question that you want.

Josh: Do you think people have more social anxiety nowadays? Like, is it hard for people to network, take the leap and network?

Caitlin: Yeah, I mean, I think there is a degree of social anxiety with social media and all that sort of stuff, but I mean, the demand for us supper clubs are just crazy. Like, well, we don't run them that often, maybe once a month, but when we do run them, they sell out within, you know, 48 hours.

Anna: We sell the tickets— well, I mean, less than that, but they're available for 48 hours.

Caitlin: Craving that, like, real life connection, especially people who are sole traders or they work from home by themselves and they don't have a team or they have a virtual team. People are dying for it. And I think—

Tommy: Hungry is the word.

Anna: Hungry.

Josh: Hungry.

Caitlin: Hungry to eat.

Anna: Hungry for good wine, good food, and connection.

Harry: Yeah.

Caitlin: Yeah. And also I think a lot more people are now doing that and taking the leap because entrepreneurialism— is that a word? I don't even know if it is. But, you know, building your own business is so much more accessible now than it used to be. And so people see other people doing it and they're like, fuck, I can do that. I'm going to quit my job and give it a crack. And when they do that, you know, a lot of women especially aren't necessarily set up with the networks or the right information to be able to succeed. And so that's kind of what we exist to do is help people, you know, or help women specifically who wanna go off and start their own thing and set them up for success. But I think like it wasn't necessarily a business idea that we had. It was just so— It was organic. Like it was one dinner and then the next dinner, all the people that came were like, oh my God, my friend would love that, can she come? And then the next month it was like double the size. And then the next month it was like 45 people. And that's when we were like, okay, there's something in this. So it kind of just grew from there.

Anna: Yeah.

Josh: What are the commonalities? Like, what are you finding that everyone has in common specifically around problems? What's a common problem?

Anna: It's a good question. I think it's a few things. I think, you know, a network. So just being able to, you know, share your wins and your problems with someone else that understands and cares. I think people were looking for contacts, so suppliers, you know, yeah.

Caitlin: Mentors or, you know, someone that can introduce me to that person or, you know, yeah, the contacts has been a huge piece.

Anna: Contacts has been a big one. And what else were they like there?

Caitlin: I think certain like skills as well, because a lot of people are taking the leap, taking the leap and starting their own consulting business or, you know, side hustle or whatever it is, and you're expected to do everything, you know, especially if you're a single founder, you have to do everything. You have to do PR, marketing, product development, sales, networking, blah, blah, blah, blah, blah. And a lot of people don't necessarily have those skills. And so they're looking to kind of fill in the gaps.

Anna: So yeah, the know-how.

Tommy: Any cool storeys of, you know, people have formed connections, you know, and then created a business together or wasn't the intention of coming to do one thing and they've got something else out of it.

Caitlin: Um, we've had people that have had like secured jobs. Yeah, yeah, that's cool.

Anna: Yeah, so cool.

Caitlin: Um, yeah, we had a good friend of ours who was working at Mecca and got a job, a great job at Thankyou as head of product development through someone she met at our supper club.

Anna: Um, we've had, um, you know, people find a supplier or manufacturer through a contact at the dinner. Um, we've had people connect, uh, in terms of finding a sponsor, like sponsorship deals. So because we do have, we have female founders come along, but we also have people from, you know, the corporate world as well, which is really cool. They're showing an interest in, I guess, intrapreneurship or entrepreneurship, and they bring a lot of value. They kind of see business in an entirely different way. And so it's nice to have a mix of women at the table that have different experiences. And, you know, we do, you know, often use table topics and they guide us. And I get, you know, again, the lessons that come out of the answers to those table topics, because they're quite, you know, they're so fascinating from different perspectives, has been really helpful for for most of the women there.

Josh: The taking the leap thing. Kate, you've had your business for a while. Anna, you've, you know, took the leap leaving Mecca. What's the big misconception, do you think? Because there's something very sexy about the whole idea of just like fucking going out in flames or whatever and starting your own thing.

Anna: Yeah.

Josh: What's the—

Caitlin: It is, it's definitely glorified, that's for sure. And there's this sense of like, you know, be an entrepreneur, be a founder. And even those words for me kind of hold a bit of like, you know. Yeah. I think the hardest thing for me has been kind of moving away from being in an office environment where you're bantering with your mates all day, every day, and you've got a bit of structure. And then so, you know, we live together as well. So we work together, we're best friends, and we live together.

Josh: I guess that would make like travelling and stuff easy, like when it comes to like going to like food on the business.

Caitlin: Yeah, you're travelling from my bedroom to the kitchen table.

Josh: Yeah. And so I mean the, yeah, I guess there's the, those intangible things around the banter and the community. Um, I guess there's co-working spaces that are sort of popping up to try and feed those those missing bits? What do you think is the big misconception? What's the missing piece, do you think? Like, what would you wish that you knew when you decided to make the transition?

Anna: Oh, that's a great question. Um, I think the biggest misconception— I don't know if this is answering the question, but the biggest kind of thing that I've had to learn is that— and it sounds so stupid saying it— but like, you have to work for every fucking dollar, you know? Like, when you have a salary, you get paid every fortnight, every month, and you're doing the work and it just goes into your bank and you don't think about it. Like, when you have your own business, you have to hustle and work for every single dollar, and you might be working the hardest you've ever worked in your life and earning nothing. But, and I'm still trying to get my head around that. I don't know if, yeah, so anyone else can relate to that.

Josh: But yeah, well, it's easy to become like evangelical about the whole thing, like when you see your mates who are like employees or whatever, and you hear what— and like, do you have any connection of like what you do and how that makes money? Like, a lot of people are shielded, especially I guess in the new economy of digital and all that sort of thing, where it's not bricks and mortar. It's not like you necessarily will see anyone.

Tommy: They're users, they're all these, you know, it's these content roles as well, especially because you, you, you know, creative roles where you're just meant to be creating stuff or videos, and then it's like, how does that connect to a dollar?

Harry: Yeah.

Tommy: And how, yeah, how's that impacting how you make— how you don't care about cash flow when all you, when all you need to do is work out what's a cool video or something like that. Yeah, it's disconnected. So I feel the pain. Like, I know it's— and so how have you lent into it?

Caitlin: How have I lent into it?

Tommy: Does Kate take care of it?

Anna: Yeah, it's just me.

Caitlin: Yeah, it's just, it's just, you know, just running on the treadmill.

Josh: I mean, did you, Kate, did you have that experience having had your own business in regards to cash flow and all that sort of stuff?

Harry: Or—

Anna: yeah, yeah, absolutely. So I worked, um, I've been working, you know, for myself for about 5, 6 years. So I know what that's like. And it's hard because you can, you can share, like, I can tell you all the things, you know, but it's until you really step into that position and you go, holy crap, you know, I don't have someone putting money in my account every week or every month, you know, I have to work for every single dollar, then it becomes the reality. And so, yeah, it's hard to kind of— hopefully, you know, I've kind of imparted as much advice as I could. And, and like, you know, I think it's kind of softened the blow, the fact that I've been through it. Um, but, you know, it's just more ongoing challenges. We're a startup at the end of the day, and, you know, we have to figure out a way to make money and survive.

Caitlin: Yeah. And I think it's also being really strategic about what you go after and what you don't. Like, when I was working at Mecca, if there was an opportunity, it would be like, yep, let's do it, let's do it, let's pursue this, let's you know, you know, develop this, whatever. But when you're in a small business, you have to consider the value of every single thing that you choose to do, because if you say yes to something, then you're saying no to something else.

Anna: Yeah, it was kind of a double-edged sword because, you know, when you're working for yourself, you have— you've got the freedom, right? You have the freedom and you can say yes to anything. But there are so many opportunities, right, out there that you have to kind of whittle them down and say no and focus on what actually, you know, is the most valuable at the time. So yeah, you've got all these opportunities, it's like shiny object syndrome. You wanna go after everything, but really what's the most sensible thing to pursue? And that's what we're trying to figure out at the moment.

Caitlin: Yeah, right now.

Tommy: Well, it's not for everyone, is it?

Anna: Yeah, it's hard, it's a hard balance.

Tommy: I think you said like the entrepreneurship or being an entrepreneur is a fashion accessory to some degree nowadays. Yeah, it's a very hard thing. And so that doesn't get you through the hard times.

Anna: No, it's not for the faint-hearted. I mean, God, I mean, both of us are like, let's just throw in the towel and go get a job. Like, you know, and a margarita. What is that?

Tommy: Because we talk about that.

Josh: Tommy wants to become a cop.

Tommy: Yeah, I heard an ad this morning. I was like, a cop?

Anna: A cop?

Josh: I don't know.

Tommy: They got— they get 10 weeks off a year.

Anna: Well, you could do that now because you— Anna was telling me the other day you have to have life experience to apply.

Tommy: Yeah, of course I have to have Year 12.

Josh: I don't have that.

Tommy: Can you actually look up Mr. 97? That's not a task for today.

Josh: You'll have to do some other— he could do it now.

Caitlin: Can he?

Anna: Like, yeah, has he had enough podcasting experience to be able to apply.

Josh: Surely you can just have Grammarly and you'll be fine.

Tommy: I mean, how much is, how much writing, how much shitting?

Anna: Yeah, yeah.

Tommy: How much writing is there?

Josh: You just need to know how to use a gun or whatever and a taser and all that sort of thing.

Tommy: It's not that, sorry.

Josh: What is it? What are the biz?

Anna: What are the?

Josh: Yeah, do you think about the bit of the jobs if you were to have a job? It's a fun process. It's like, it's the equivalent of, it's the opposite of thinking about what you're gonna do if you like win the lottery, right? It's like if I was to give away all my dreams, Oh my God.

Anna: Oh, I don't. What's yours?

Caitlin: I do know what I do not have one because I'm like, no plan.

Anna: There is no plan B. Yeah, this is it.

Caitlin: Yeah. You know, and you know, I'm quite lucky in that Mecca has said to me, you know, if you ever want to come back, you can. So that's great.

Josh: Like a plan B.

Caitlin: Like that's a plan B. Yeah, that's exactly. It's a plan B. But I just know I can't imagine experiencing the freedom that we've experienced going back and being in a 9 to 5. But, you know.

Anna: Yeah, the joke is to go back, but You just couldn't. It's too hard. And we really believe in what we're doing. So I mean, even if we won the lottery tomorrow, bloody hell, that'd be great because— but we'd know where to put the money and it would be into the business and we keep working.

Tommy: So yeah, so straight into a bar in Mykonos.

Anna: We might change where we work from. You know, we've got one-way tickets to—

Caitlin: take a cheeky vacay in there.

Tommy: I mean, what we're talking about is like the fear of of the unknown entrepreneurship and doing and creating something from scratch. It's like no one knows if it'll work. All the good businesses, no one necessarily knew because there's all the ones that didn't and they all thought it was going to work.

Caitlin: Yeah.

Josh: Yeah.

Anna: Well, most fail. Like, that's the reality.

Josh: But I guess the other thing too is it's like, I think sometimes we ask for advice from people, but it's like they're not doing it yet. We're expecting them to be like across why we're doing it and getting that sort of value from them.

Tommy: What's the consistent pattern across the people you meet that come to your events that is like, they believe in something and like, they truly believe it whether it'll work or not?

Anna: Yeah, they do. And I think it's really important to have a vision and to understand what your why is, you know, like what's your reason for being and for, you know, blindly pursuing something. You know, we're pretty clear on our why. And I think most of our guests have been too. Definitely, you know.

Caitlin: Yeah, yeah, I think it's been one of the consistent things across everybody that we've interviewed is everybody has had this like vision and they have been uncompromising in pursuing it. Like, you know, CJ is a great example of that, and you know, Joe Hogan, who will release next year, also has the most clear vision, but they're, they're willing to do anything to get there, you know, and they're willing to pivot and change and sacrifice this and, you know, get there in a million different ways, but that never changes.

Anna: Yeah, and I think, yeah, so often you can get stuck in like day to day, right? It's like you get bogged down by what do I have to do today? What do I have to release tomorrow? And you know, that can kind of, you can start to just, you know, float around. But I think if you're really clear on your vision and where you're heading, it kind of pulls you through. And so every decision that you make, you know, every decision you make is really kind of getting you to that, to that why.

Josh: What about compromises? Where does that fit in a grand vision?

Anna: You have to compromise, and sometimes you have to pivot based on what you learn. You know, it's like you're validating an idea. You know, we were talking to Sarah Friar, you know, not too long ago, and she taught us that Slack, you know, which a lot of us use, used to be a gaming application. So, you know, it started out as a gaming application and they had the chat functionality for all the gamers to kind of connect. And then they figured out, oh, well, everyone's actually just connecting through the chat thing, like, and they completely changed their product. So you have to compromise, you have to pivot. And, you know, sometimes that does get you to a better outcome. So it's kind of listening to what your customers want and listening to— yeah, it's, it's taking in all these different— all the information and trying to figure it out. And that is probably the most difficult part.

Caitlin: Yeah.

Anna: Yeah.

Josh: Doing it as a team, creating that alignment, how hard is that?

Caitlin: Look, it's been, it's been a challenge. I think Caitlin and I work in very different ways, which is great, but it also can be a challenge. But I think one thing that has held us together is that we have the same vision and we have the same values. Like, we want to help women. We, you know, we are passionate about this, and, um, it's just about having good communication.

Anna: Yeah.

Caitlin: But, you know, yeah, like, Caitlin's very, very, very considered in all of the way— like, in all of her decision-making. She'll think through everything. She'll take the time to think through properly, whereas I'm really trigger-happy. I'm really gung-ho.

Anna: She's a shiny object.

Caitlin: I'm a shiny object syndrome. And, you know, that has been a point of, you know, it's been been a point of tension and frustration for both of us, but ultimately it's great because without her consideration, I would probably have gone off in a million different directions. And without my kind of like pushing, pushing, pushing, we might not have taken the action on XYZ. So it's all about kind of balance.

Anna: We kind of balance ourselves out, each other out, which is really nice. Yeah.

Josh: What's the difference between the duo, the partnership, and say having Mavah, like in that sort of 3-person? How does that change dynamics, do you think?

Anna: Um, yeah, I mean, I guess you've got that third person, so if you ever have a tie, a tied decision, you've got someone that can go one way or the other. So sometimes, you know, we may—

Tommy: someone who's very thought out would say something like that. Yeah, so that sounds like it was straight out of a contract, like a shareholder's agreement.

Anna: That's because we've been doing a few of those lately. Yeah, yeah, yeah, yeah, yeah, obviously. Who combs through the contracts? Yeah, um, uh, but you know, obviously she's Yeah, she would help us kind of make the decision. So sometimes we're tied up and we might just throw it to our other housemate or we'll throw it to someone, the dog. I mean, anyway, I'm just like—

Josh: What does your other housemate do?

Caitlin: He is a strategy consultant for a sports marketing agency. Okay, great.

Anna: Yeah, yeah. So he's smart.

Caitlin: Yeah, he's smart. Yeah.

Anna: So I mean, the poor guy, you know, he's run a few strategy meetings. Yeah, he's like, I feel like I'm, I feel like I'm living in a startup environment. And it's like, yes, I'm like, boards in the living room.

Mason: Put your hoodie back on.

Anna: Yeah, yeah, yeah.

Josh: Yeah, get out of your suit, mate.

Anna: What are you doing?

Josh: It's a stand-up.

Harry: Get up.

Josh: Yeah, get out of that gear.

Anna: Oh God.

Caitlin: No, he's a legend.

Harry: Yeah.

Josh: The thing with like going to New York or whatever, or even having that in the whole strategy, like New York always comes up, Melbourne, Sydney, New York.

Caitlin: Yeah.

Josh: Why and what does that do in regards to the vision or how you look at the whole, you know, business?

Caitlin: I think we went to New York partly because of the wedding, but also partly because, you know, the podcast space is becoming quite saturated, especially in Melbourne. There are a lot of podcasters in Melbourne and there are a lot of guests who are sort of cycling through the same, the same guests who are cycling through those podcasts. And, you know, one of the points of difference for us is like we want to be able to get the guests that other people can't get. And so part of that was going international. And, you know, we had a mutual friend with CJ Hendry. I used to live with her ex-boyfriend. And so we landed her and it was like, like, yeah, like, we've got to go. She's like, does no press really ever. She's only ever done one other podcast interview. So we were like, yeah, we've got to go for that. So I think that has been, that has been important in terms of differentiating the podcast. But with LadyBrains, like, we want to build a global business and we want to build global communities and sort of connect these startup hubs of the world. And so Melbourne, Sydney, New York, that's kind of just how it's evolved.

Anna: And, and that's just the start. Yeah, hopefully, you know, I think, yeah, we want to connect all of the startup hubs. Um, and I think that's quite exciting, you know, we're kind of all doing, we're all doing the same thing, right? We're all starting businesses and we've all got the same similar challenges. Um, so how can we connect founders globally, um, and learn from each other? I think that's kind of also the next piece.

Tommy: Yeah, I was thinking about the, you know, rich people's problems, people who don't have much money, and the similarities of the struggles that we all have. Yeah, it's, it's a, um, it's a comforting piece to understand that everyone is going through. I've said that before. It's like I find some solace in that, like we are all going through our shit.

Caitlin: Yeah, and it's interesting, like we interviewed someone a couple of days ago, um, who we're going to release next year, um, Kate Morris from Adult Beauty. She was amazing and she just sold 60% of her business for, you know, hundreds of millions of dollars. And she was telling us that in 2014, they almost went under and they couldn't pay payroll because they didn't have the cash flow. And she'd been in business for almost 15 years. She was a multimillion-dollar business and she's experiencing the same problem that we are, that small businesses do. And so that was kind of, that was quite powerful for me.

Josh: But she rents out her pool.

Anna: So she's like, yeah, she rents out her pool.

Caitlin: Yeah, that's it.

Tommy: But she can fund the app, to be honest. I love it.

Caitlin: She can now, yeah. Yeah, yeah, it's—

Tommy: and so it's, um, it's a funny one because it's— but we all— it feels like we've got the biggest problem in the world, you know, when it's your own, right? How do you get perspective? Uh, how do you girls— because I have an idea of how I gain perspective on the situation I'm in. Is there a tool that you use that makes the big things seem smaller?

Anna: Yeah, great question. Um, I'm pretty high in my strengths in perspective. Um, so I think just kind of just checking in. I think gratitude, gratitude's a really good practice, whether you just kind of figure out what are you grateful for this week, this month? Some people journal, I just kind of have a think about it. I think being grateful for what you have is, and the experiences that you're going through, like holy crap, I get to try and build a business with my best friend. We get to travel, it's freaking cool. And I think, yeah, it's hard. There are definitely challenges and you don't know where the money's coming in from. But at the end of the day, we've chosen this path and I'm grateful for that. So gratitude helps me personally.

Tommy: There's a piece of self-development in starting any business 'cause you need to work out, like, so for instance, yesterday, Michael Bungay Stanier, who was on, mentioned something around him being more risk adverse when it comes to money. So he holds it in a bit closer. And so he's identified that. Is there something you've identified in sort of how you approach it in a difference? You mentioned the,, you know, thought out or seeing how it all plays out. You're a bit more gunge.

Josh: What's the personal values, personal values that end up really translating? Like for Tommy is very specific on where are we spending money, expenses, how can we cut? And I'm always like, let's just get bigger clients so we can service my dumb things I'm buying.

Anna: What are you buying?

Josh: Yeah. What have we got?

Caitlin: What?

Josh: Harry.

Tommy: Harry, no.

Caitlin: This is microphone.

Josh: Harry literally just did this. I don't know if you saw that. No, these are—

Harry: I gestured at everything for those.

Tommy: Yeah, yeah, yeah. Playing at home. Yeah, but when does it—

Josh: $3,500 in these, by the way.

Anna: Well, I did ask before. No one wanted to answer how much it was.

Tommy: You need to answer the question we asked.

Anna: Oh, well, guess not.

Josh: I can't remember. Anyway, go on.

Anna: $3,500.

Josh: Yeah, that was a lot. But no, so the— what is that for you? So yeah, I guess it's the whole thing of, for us, it's the expense. And working together works really well because it means that I've actually dialled in And like Tommy does a lot of the, like the stuff goes on his card or whatever. And so he's across it all and stuff. And, but then I'm able to bring the other side, which is the posture of asking for more money or working out ways of generating more. What is that for you two? What are your strengths?

Anna: Oh yeah. Well, so just on that, I think we're pretty lean. We don't spend a whole lot of money. Like, I mean, Yeah, which is good. Not yet anyway. We'll see what 2020 looks like. So in terms of figuring that out, we're pretty, we're across.

Caitlin: We're both across.

Anna: We're both across what we spend.

Josh: Is there a way or a formula of determining whether you should buy something or not? 97, what's some dumb shit that, or what have you put on? Well, 97, you got the tattoos.

Caitlin: Oh yeah.

Josh: He decided to get, what are they called?

Mason: What, the temporary tattoo?

Caitlin: Yeah, just temporary.

Mason: Yeah, temp tattoo.

Josh: He ended up putting that on his ING because he didn't want it, he couldn't be bothered bringing it to us.

Tommy: I was actually going to blow up then. You asked him, I didn't approve that.

Josh: You did approve that?

Tommy: No, no.

Josh: How much was it? So 97 couldn't be fucked asking how much did it cost?

Mason: It was $30.

Josh: $30.

Caitlin: What was the ROI on that $30 spend?

Mason: Well, we'll have to see in 2 weeks. They're going to be on the show in 2 weeks.

Caitlin: I say. Yeah, you heard it here first.

Anna: Can we steal that? What do you reckon? Temporary tattoos?

Josh: It's a good idea. Yeah, I mean, you could have a henna station or something at one of your—

Caitlin: Well, we actually, a good friend of ours, Phoebe, has a brand called The Memo, which is a baby e-com site. And at her launch party, she had a tattooist. So Gem Watts got a tat there.

Josh: Queen Gronkh, she got the tattoo.

Caitlin: Yeah.

Josh: And the funny thing is she had a can of Coke, a bottle of Coke. And I thought she said, oh, it was to keep her sugars up. And I was talking to her and she actually, she brought the Coke with her. I'd assumed that they had it on standby.

Anna: She knew she was getting a tat.

Josh: So I thought, I'm still trying to work out what this is. I don't know what's the tattoo got to do with the Coke.

Anna: To keep her sugar levels up.

Tommy: For what reason?

Caitlin: In case she faints, I guess.

Josh: It's a good excuse for a Coke.

Tommy: Yeah, that's what I was getting at.

Josh: I don't know how it connected to the natural complexion.

Anna: I mean, it was BYO. I don't know.

Josh: Does that actually not help?

Tommy: I don't know why that would help. Blood sugar relating to a a little tattoo. I don't think there's anything. I don't know. I don't think there's connection. But what did it say? Do you know?

Caitlin: I can't remember.

Anna: What did she get?

Josh: I can't remember.

Anna: Was it words or a symbol?

Mason: It was, it was, it was something for a dog.

Caitlin: Oh, it was, um, good morning, I think. Good morning. Yeah, I think so.

Anna: What did Phoebe get?

Caitlin: I can't remember.

Tommy: Did you get one?

Caitlin: No. No, I considered it but didn't.

Anna: So you would never Yeah, I considered it for a brief moment. It's for a split second.

Josh: And so the formula of working out what to spend money on when push comes to shove, how are you going to work that out?

Caitlin: Look, it's just on a case-by-case basis. Like for example, with our launch of season 3, we had a marketing budget. We were like, we're going to spend X on this. And we just figured out how to spend it. And yeah, you know, we did an activation in Cremorne that was super successful. It went sort of bonkers.

Josh: That was at Cohen Co. Yeah.

Caitlin: Yeah, that was a cheap activation. We literally stood at the front of Co+Co and we told our audience and we were like, you get a free coffee if you share on socials. And who's going to say no to a free coffee? And also strategically, it's in amongst all of the creative agencies and a few big media publications.

Josh: Close to ball games. The basketball scares me sometimes.

Caitlin: Yeah.

Josh: But Bree, my girlfriend, she got a coffee and I was like, oh, you posted on Instagram. She goes, No, not yet. I was like, what are you doing? You got to post on. So I, yeah.

Caitlin: Did you make it?

Josh: Yeah. Yeah. Thanks.

Anna: Follow through. Watch, she just took the free coffee.

Josh: Outrageous.

Anna: So outrageous.

Tommy: Putting yourself, putting yourself out there, creating content. Yesterday, young Harry was coached on the show, you know, and it was about the confidence to put things out into the world that, you know, really put your name behind something. What is it for you? What's your feeling around putting stuff out into the world that you've got your name on? Oh, how does it make you feel?

Caitlin: Do you know, it's a really tough one. And we have been speaking about this for so long because obviously we've got the podcast, but, and we've got LadyBrains. But for us, where we like, we are the face of the brand, I guess we're the face of the podcast a little bit, but the LadyBrains is not about us. It's about the community. And we want to build a brand that is so much larger than just us. And so I think we've kind of held back from putting our face out there and doing video content. As a really good example, we haven't really done any video content, um, because we're like, it's not about us. On the flip side, you know, brands grow so much quicker when there's a face to them that people can connect with. And so we're trying to, we're trying to find that balance. It's, I don't know, what do you think?

Anna: Yeah, definitely. I think, you know, personal brand is a big one and you need one, and you guys have done so well building your personal brands.

Josh: Um, what do you think our personal brands are if you were to describe us as individuals.

Caitlin: Um, now I know Bogan.

Anna: Um, yeah, and so like it can be really hard putting your—

Josh: I won't push it.

Anna: Um, it can be difficult to put your name to it for sure. I mean, I think what, you know, putting the brand name to something is one thing and then putting your own personal names to something. This is our first podcast interview.

Josh: Oh really?

Caitlin: Right. I know it's not. Oh yeah, it is.

Anna: It is a kind of first podcast interview.

Caitlin: Yeah, it is.

Anna: Sorry. So now it's not.

Tommy: Kate just punched Adam in the stomach.

Josh: This is what happens. This is the problem with having a duo. Like you get like this bullshit, like calling it like, but it's also this call-out culture on show. Like Tommy's always calling me out for things. That's fine.

Caitlin: Well, we have actually been interviewed.

Anna: We've been interviewed once, but it hasn't released.

Josh: Hasn't been released.

Tommy: It doesn't count. There's only one daily talk show. The Daily Talk Show.

Caitlin: Yeah, there is.

Anna: Yeah.

Tommy: I think like what you're describing about deciding on whether to to pursue building a brand that lives beyond the people behind us and then building your own personal brands. I mean, some piece of advice someone gave me is like when I was having that exact conversation was, who do you think of when you think of Apple? Who do you think of when you think of Virgin? And really, you could reel off a bunch of Boost. You think about the founder, Janine.

Caitlin: It's like, it's true.

Josh: And so do you remember Janine's favorite? There was a specific, like she had her own smoothie, but they've taken it off the menu.

Tommy: Too naughty?

Josh: It was real naughty. That's the thing, you look at Janine and you're like, she's healthy as fuck.

Caitlin: Which part of naughty is not healthy?

Josh: It's called Janine's Favorite, and so I'd be like, fuck, she's lean, I'll go that. It was like fucking 2,000 cals. It was like the mango— it was, it was mango ice cream. Yeah, but there is that whole thing Christian Hull said, uh, to us, people follow people. Yeah, there's a, there's a bunch of tree Truthfully, 100%.

Caitlin: I mean, connect with people and people's storeys more so than you connect with like a faceless brand. So that's actually a really great way of thinking about it.

Anna: I haven't really thought of that before.

Josh: Say it again. I've forgotten.

Tommy: So when you say a brand, what was that?

Caitlin: Yeah. So you said, you know, when you think of big brands, when you think of a brand like Virgin, you think of Richard Branson, Apple, you think of Steve Jobs, Boost, you think of Janine. It's like they have, they have been able to build their brands beyond themselves, using themselves as a bit of a tool.

Tommy: But let's dissect it. Is it that the business behind the thing that they're doing is so strong? So the business model behind Jeanine Ellis's business would survive regardless of her. So if she actually was a silent person within it, or is it the fact that she pounded the pavement, started the first and got it out there and then sort of gets behind it, inspires other people to you know, you can create a business, I can help you do that. So the franchise model, I'm just, I don't know the answer.

Josh: What about organic media? If you think about if you're a journo and you're writing something, the first thing you're going to be like is, who do I have access to? For July Luggage, it's Ethan Tedaskalou. For Hey Tiger, it's Scientaid. Like everyone needs a contact to face off, really, the brand. Yeah.

Caitlin: Yeah.

Josh: I guess that because if you're just talking about brands, at that point it's sort of like just advertising, I guess, versus like the people storey that people are going to connect with.

Tommy: And then I try and work out, so, you know, the cheekiness of Virgin. So it comes from Richard Branson, who himself is cheeky and he's that guy pushing the boundaries and doing all this wacky shit. And so it then the personality of the founder, like becomes the personality almost, or the tone of voice. Like, yes, I think like the Frank girls have done Frank Body.

Caitlin: Yeah, they've done that one.

Tommy: They've done so amazingly because they've created this pseudo, you know, this.

Caitlin: But then what about brands like Red Bull?

Tommy: Yeah, who the hell owns Red Bull? Who the fuck owns Red Bull?

Josh: But if you think about it, they're still, it's still got the people focus, media content, all like adventure, exploration stuff.

Anna: The ambassador program, but all the girls that drive the cars around.

Tommy: Yeah.

Anna: And they're in extreme sports, you know, and they're extreme sports.

Caitlin: And all the athletes that are just plastered But even like, you know, Nike, like, okay, yeah, Shoe Dog is a book now and people know who— I think his name's Bob. But like that brand grew without the founder being the face. So there are examples of both. But I think there was a stat that one of our friends told us the other day that was like brands that have a founder as the face grow 800% quicker or something like that than brands that don't. And I think that's true.

Tommy: You know, it's an easier it's an easier conversation because I think Josh and I were talking about this. It's like when you're starting out, most people try and seem bigger than they are. Yeah. To try and—

Josh: We're saying, yeah, what makes something seem a bit povo? And it's when you're trying to be big. It's when it's like, yeah, we are this and we're doing this and we're on a thing.

Harry: Sorry, I was thinking about the email the other day.

Caitlin: What email?

Harry: The Cat Cafe. And I said, one of Australia's largest podcasts.

Tommy: No, that was exactly right. That's exactly who we are.

Josh: Harry did— how did that go, by the way? So Harry did a—

Harry: they can't do it.

Josh: You don't yell, remember?

Harry: Oh, sorry, I don't have headphones.

Josh: They were so far away.

Harry: They can't do it. Something about the cats, not enough cats or something. But I thought, I thought, I thought, what about if we do it at 97's sauna outside broadcast?

Josh: Wait, hang on, he doesn't have a sauna.

Anna: Are you renting saunas?

Mason: No, no, no. Just at the gym. At the gym there's a sauna.

Tommy: Just to bring you up to speed, we sort of tasked Harry to organise an outside broadcast at a, you know, a shelter outside.

Anna: Can we come?

Josh: Yeah, well, it's not happening anymore.

Anna: Well, find another one. Yeah. Was it the one in the city?

Harry: Yeah.

Josh: So what did they say? Not enough cats?

Harry: Yeah, there was something to do about cats or—

Josh: But how can a cat—

Harry: I remember endangering cats.

Anna: Oh, endangering cats is different to not having enough cats when you're a cat cafe. Yeah, it doesn't make sense.

Josh: You did a strong sell.

Harry: Can you get— we could go to Japan. There's an owl cafe.

Josh: An owl cafe?

Caitlin: That'd be awesome.

Anna: Yes. I saw 3 owls last night, just randomly.

Josh: 3?

Anna: They were all together. Yep. I was at home having dinner and walked outside and like 3 owls. And then he's like bobbing his little head and then he flew down in front of me. It was quite— I felt like I was in Harry Potter or something. It was quite amazing.

Josh: And you live in the same building?

Anna: I went back home for dinner.

Caitlin: She's like, where's my housemate?

Anna: She's out the front hanging out with ours. But yes, I'm on board with that idea.

Tommy: Can we use your company card to get that?

Anna: You guys have status, don't you have free flights by now?

Josh: Yeah, we should. But just on the sauna thing, I know we don't normally get into dreams, but 97 was saying you had a dream that involved this. What happened?

Harry: It ends with a great idea.

Tommy: Oh, wow.

Harry: I'll only say about half of it.

Caitlin: Oh, is this safe?

Tommy: Sure.

Harry: I assumed that the cafe would just go kapunk, so I had the dream that we were having it at 97 Sauna.

Josh: It was an actual dream?

Harry: A dream, a full-on dream. And then I went, when I woke up, oh, that's a good idea. But Tommy was freaking out because the lens was fogging up and all sorts of shit was going on.

Caitlin: Also quite a small space. How many people are you expecting?

Josh: Well, there'll just be us.

Tommy: And it's not happening in a sauna, to be clear.

Harry: I want to know why I'm not reading the I need another.

Josh: Next summer.

Tommy: Kate wants to know what happened to the other half of the dream.

Anna: I want to know the second part of the dream.

Harry: Well, it was actually one of those Japanese onsen. Yes, yes, it turned out to be one of them.

Josh: So you're all tying up stuff? No, no, no.

Tommy: What's the Japanese thing that you did? Shibari. Japanese bondage.

Josh: What was the funny bit? What was the Japanese bit?

Caitlin: It's just a Japanese onsen, the spa where you go in naked.

Anna: So you were all naked.

Josh: So why? So it was because we were naked, is that why you couldn't say?

Harry: Yeah, it was really— well, I didn't know how far you wanted me to get, but it was just a bit— it was just— it was a strange dream.

Josh: Yeah, it was. Yeah. What do you think about— so 97 always comes to me with all the dreams. He is like very specific with these dreams. Do you have vivid dreams?

Caitlin: Um, yeah, I have a few vivid recurring dreams.

Josh: Okay, so like constantly traumatic.

Caitlin: Yeah, I have Constantly have the teeth falling out. Oh, dream.

Tommy: What does that mean? Can you look that up, please, Mr. Nice Hands?

Caitlin: I'm pretty sure it means that you're going through change or stress or something, and that happens on the regular.

Josh: Look, all your teeth?

Caitlin: Yeah. Oh, sometimes it's part of my, part of my teeth. Sometimes they crumble. Um, the other day actually I had a dream that I lost a tooth and it was full of diamonds.

Josh: That was a good sign.

Caitlin: That's great.

Tommy: Mr. Nice Hands, did you find it?

Mason: It makes so much sense. So the dream could indicate that you're dealing with some kind of loss an abrupt end of a relationship or a job change.

Josh: Job change, that makes sense.

Anna: What about with diamonds? Diamond teeth?

Tommy: Is there any others?

Anna: Um, yeah, so I had one the other night. It was so random. I remember I told you, um, I was in a— I was in a restaurant which also had a public pool. Pools seem to be coming up. Um, and I went to the bathroom, and in the bathroom were— was a It was a big black bear and all these tiny bear cubs just hanging out in the bathroom. Bear cubs.

Josh: Were they staring?

Anna: Why am I dreaming about bears and bear cubs?

Josh: The diamond thing, 97.

Tommy: What are you at?

Mason: The diamond thing is a symbol of wealth, power, love, and attraction.

Caitlin: Oh, great. Hello.

Josh: Good. Great. Yeah, I think that's positive.

Caitlin: Need a bit of that.

Mason: And bears symbolise strength, power, and independence.

Caitlin: Oh, great.

Josh: Oh, that makes sense. So strength within the context of it. You say it was a bathroom?

Anna: Bathroom. Yeah, I don't know why they're in the bathroom and why I was in a restaurant that also had a public pool.

Tommy: But anyway, are you into, you know, I guess people call it woo-woo thinking, like looking at the meaning behind dreams or things that are, you know, superstitious?

Josh: Horoscopes? I read 97's horoscope on Sunday.

Caitlin: Oh, good.

Josh: No joke. It said you have a new job on the horizon. So that's awkward. Yeah, it was.

Tommy: Well, the clinks We did a clinker game where you bite it and it tells you the colour relates to a question. So, yeah, will you stay in this job? And it said maybe for me. Fuck science. Yeah, so they're good.

Josh: So the— yeah.

Tommy: Are you into anything?

Caitlin: Yeah, I mean, look, we sage our house.

Josh: Um, just smells good though.

Caitlin: Yeah, it smells good, but you know, we'll do the whole ceremony, you know.

Josh: Oh, that's good fun.

Tommy: What's your housemate doing?

Josh: Yeah, it's strange.

Harry: Asthma.

Tommy: Girls!

Mason: Seriously?

Anna: Yeah, he probably doesn't appreciate that. But, um, yeah, what else do we do? I mean, we've got this app called Pattern, um, and that— what does it actually tell you?

Caitlin: Pattern is basically you put in your birth date and it gives you daily indications of like what's going to happen or where your head's at or what you need to focus on. But you can also like link up with other people's patterns so you can kind of see what's happening within your dynamic of your friendship or partner or whatever.

Josh: I unsubscribed from Bree's period the other day because I got— was getting like Flow, I think is the app or whatever.

Caitlin: Yeah.

Josh: And so I was getting constant emails and they're so long.

Caitlin: Oh my God.

Josh: And so it's just like, can that be— I was like, I hope it doesn't— I hope she doesn't get notified that you've unsubscribed.

Caitlin: Yeah, that is classic. I didn't even know that was a feature.

Tommy: Yeah. And so are you, uh, making business decisions based on this app?

Caitlin: What's the deal?

Tommy: Like, what's today?

Anna: Oh, I should have a look at our phones.

Josh: Harry can go through.

Caitlin: Oh dear.

Josh: Podcasting. What is the biggest misconception? Like there's so many people that want to start a podcast. Where are people completely wrong, do you think, when it comes to podcasting or their perception of creating a podcast?

Caitlin: I think, I mean, I don't know whether there is a perception that it's easy, you know, just get a microphone and press play and upload.

Josh: Because if you miss the recording bit.

Caitlin: Yeah.

Anna: Of course. Well, we have done that. Don't worry. We've lost some audio before. That's all right.

Caitlin: But yeah, I just think like it's so much work. And also, you know, if you want the quality to sound good, which you have to have great production quality because otherwise people will automatically just, you know, listen and then tune out.

Josh: Yours sounds so good. Like I reckon, yeah, it's one of the best. And it's like it doesn't take like you just need people getting close to the mic. Like I saw the behind the scenes with CJ and she's just holding it.

Anna: She's holding it. Yeah.

Josh: But it's good. That's all. Like it's actually not that hard if you get the fundamentals.

Anna: That's it. And we invested in like you guys have, we invested in, you know, a good travelling kit. And now obviously we can also record in the studio, which is like amazing. Prima quality. But yeah, I think, you know, you have to, the sound quality has to be good. And, you know, I think you've you've just got to figure out like what's your point of difference. What's your— like it's kind of saturated now and it's, you know, everyone's kind of launching a podcast, which is great because I think that's the future of audio. But I think you really have to consider how are you different? What's your point of difference? How does it fit with your brand? Like if you've got a brand already, what's the strategy behind it? Don't just like go and launch it. Like put some thought behind it because I think you're going to perform a lot better in the long term.

Tommy: And, um, the shiny object, object, uh, view on the podcast thing, what's yours, Anna?

Josh: Um, uh, as in like what people—

Tommy: I know, because it's the— that's—

Caitlin: put a lot of thought perfectly.

Tommy: Yeah, put thought behind the podcast.

Anna: Oh yeah, that's definitely it.

Josh: Did you just go, did you buy the gear? And was it like—

Anna: we all, we all trotted off to, uh, well, it's actually the store's just around the corner.

Josh: Store DJ. Right. They've got some decks as well.

Mason: Yeah, yeah, yeah.

Anna: We built it over time, didn't we? We got the mics and we got the stands and we got the headphones. Oh my God, the headphones make such a big difference.

Josh: Yeah. You know what the actual—

Anna: what it sounds like, you know, because you're like, oh my God, yeah, you're just kind of like, you're moving away and the guests don't know because we obviously, we know to stay close, but your guests have no idea. So the headphones were a great addition to the kit. Yeah, we just, we trialled it. Trial and error. Yeah, really?

Caitlin: Yeah.

Anna: Yeah.

Tommy: I like to look at sort of industries as, you know, they gain games. If it's— you're in the radio presenter world, you're— you need to be up for playing a certain type of game. It could be in the corporate environment. Environment. It's like there is a game.

Anna: Yep.

Tommy: That you play in the corporate environment. It's not one for me. What do you think are some of the things that happen in the podcasting game that you have to be up for? One being an example, forgetting to press record, because that's like, if you know, you're signing up for that essentially, that there's an opportunity, there's a potential of it happening.

Caitlin: Yeah. Um, what else?

Anna: What else is there?

Caitlin: Um, oh God, I don't know. Oh, I like, you know, we have people cancel on you. Yeah, you know, we have been trying to get Pip Edwards forever, and we had her locked in for an interview, um, probably a year and a half ago now, and she had to cancel, which is fine. Never got her back.

Josh: I keep getting retargeted with Estée Lauder. She's talking about Sriracha mayo. I don't know if you saw, like, it's her favourite moment. Yeah, that's cool. For whatever reason, it just kept hitting me on Instagram. Sriracha mayo. Like, I'm like, um, next one.

Tommy: What about connecting with guests? So yesterday we talked about the first sort of 25 minutes in any conversation is like, is this kind of trying to build rapport to find and find your thing? Got it.

Caitlin: Yeah, yeah.

Tommy: What is there something around that for you?

Caitlin: Uh, it's been interesting for us because majority of interviews that we've done have been offsite. So we'll go out to the offices and we'll, you know, be in their environment. And so they're automatically kind of at ease and we'll have a bit of banter and a bit of chat.

Anna: And, you know, we tend to show us around, you know, like it's very different when you're going to someone else's environment. Yeah. Because then naturally they're at ease.

Caitlin: Yeah.

Anna: They're like, oh, come into my space, I'll show you my warehouse, I'll show you, this is my intern, you know. And so it's like, it's great because you, you know, you're in their space. So their guard's already down. And then yeah, we'll have chitchat. I mean, we'll banter. It's, you know, women, we know how to talk, right? Like we just, we get going and then we'll like do a little record.

Caitlin: Yeah. I mean, we have to work a little bit harder in the studio because when we're at PodcastOne, you know, they're coming into the big, you know, Fox FM building and we've got our producer there and there's frankly not as much time to banter because we're in the studio and we're there for an hour.

Josh: How does it change your performance? Do you think?

Anna: Um, I think it's— so we've done a few now, 2 or 3. Um, I would say that it's probably more formal.

Caitlin: Yeah.

Anna: Um, we're, we're probably cleaner in asking the questions, which is, which is good, but you kind of miss the banter. We— I think when you're off, when we're offsite, where we just like— and we'll chat for a lot longer.

Harry: Yeah.

Caitlin: So like, which CJ, we were with her for 2 days. So you couldn't do that.

Anna: Yeah, we recorded for 8 hours. 8 hours of content.

Mason: Not all of that.

Tommy: You were on the floor?

Josh: You were on the floor.

Anna: With my stand on an Hermès box, you know, and she's guzzling Coke and it was just great.

Tommy: Yeah, I did read that status of like 8 hours of recording.

Caitlin: Was it? It was an hour. And to be honest, there is so much gold that we're thinking about how to release some more, but you can't do that in a studio.

Josh: So everyone says, oh, why don't you start a Patreon? Like, if you're going to start a Patreon, you you're gonna suddenly be making like heaps of cash.

Caitlin: What's a Patreon?

Josh: It's like the people subscribing and they give you a show. Yeah. So, it's like, we'll pay you $5 a month and you give us almost like Kickstarter, but a subscription type of model. Do you think that people are primed to pay for content? Do you think people are going to?

Caitlin: I think we're in this like machine of free content. There's so much good content out there that's free that the standard has been set. I think it would be a really hard— it would be a hard job to convert people, I think, to paying for a podcast, even if it's good. Yeah, even if it's good. I don't know.

Anna: Yeah, I mean, there are those services, but I agree. I think, you know, there are so many free platforms, but that's where, you know, ad revenue is going to increase. Like, you know, obviously brands can advertise, and because ads have kind of been a part of podcasting from the beginning, thing. We're used to it, you know. It's not like, um, you know, we used Instagram for a long time and there were no ads, and then it was quite jarring. But I mean, obviously you adapt, right? Users adapt. But, um, I think, you know, people are used to listening to ads on podcasts, and more and more brands are going to get on board. And, and that's where the spend is, I believe. So it might not necessarily— people might not necessarily pay to listen to podcasts, but I think they'll be fine with ads. And I think more and more brands are going to start spending there.

Caitlin: You do bring up a good point though, is like, how do you actually monetize this audience that you're building? And how do you commercialise this asset that you have? That, you know, I mean, that's hard. And I think everyone's trying to figure that out at the moment because it's such a new space and there's no kind of like set business model attached to a podcast show. Everyone's trying to figure out where to take it and how to make money. And is it this, is it that? So yeah, it's, it's, that's kind of a challenge.

Anna: That's a question. How are you guys monetizing your audience?

Tommy: Um, I'll take the fifth 5th. Because I mean, you guys would— from the Bikram documentary, and he was being interviewed. It's so— the Fifth Amendment means you don't have to answer the question.

Josh: That was so nuanced though. I mean, that's a very specific joke. I watched Bikram, great.

Tommy: I wanted to talk about it a lot. Yeah, I wanted to throw it in.

Caitlin: I found mine.

Tommy: So the Bikram documentary, that is outrageous.

Anna: It's gonna kill me because she's It's like every night the whole last week, she's like, I really want to watch it. I really want to watch it. I'm like, I'm just not in the headspace for that right now.

Caitlin: Now we have nothing to contribute because we haven't watched it.

Josh: It's worth watching.

Tommy: It's good. I don't need to get into it with people who don't understand. Oh no, no.

Anna: All right, man. Give us a little overview.

Tommy: He's crazy. For one, I didn't know that Bikram, the yoga, was a guy named Bikram and he still lives now. It's not some old, old yogi.

Josh: Documentary made by an Aussie lady named Eva Horner. Eva, she was awesome. Yeah, such a good film.

Tommy: Yeah, you will love it.

Anna: Watch it.

Mason: Great.

Caitlin: We'll do that.

Tommy: I wasn't really in the headspace too, and I was like, whoa, this guy is fucking a freak.

Josh: He's quirky as fuck. It doesn't have too much of that. Like, it's not super— because I never brought myself to watch, say, the Michael Jackson thing.

Caitlin: I just can't.

Josh: It's not as dark. It's not super dark.

Anna: Okay, so it's not dark. So we'll just watch it.

Josh: It's still got— it's definitely got dark elements.

Anna: Does it make you feel more normal?

Tommy: I mean, Oh, because he's a freak.

Caitlin: Yes. By comparison.

Josh: Very much so. Monetization, leveraging audience.

Tommy: Yeah. I still choose to take that. No, I think like it's a— I think we've done quite a bit of—

Josh: I thought you fucking took the fifth.

Anna: Yeah, come on, you can't take it, man.

Tommy: She asked how you are, so I'm not telling you.

Anna: How are you monetizing your audience?

Tommy: I think there is another look at what monetization means. So you can reframe monetization. What's the first thing that comes to mind for a podcast? Ad sponsorship. So it's like literally reading out ads and getting money in exchange. And so that's one way. There is a heap of ways to work out how to make money through this thing. And that's what we've been exploring. It was like, you know, partnerships, advertising, you know, work that comes from our brand that we build within this. So it's like, yeah, I think if you're comparing to the big podcasts that are are making a shitload of money from reading out a script, then, you know, it's, it's a losing game.

Josh: I don't know if I took this from like a brand or something, but I heard it's like an influence without the influences. And I like that idea of like, we never want to go into like the influencer territory.

Caitlin: Yeah.

Josh: However, we would love to have a community that believes in the stuff that we're doing. And so in turn, you have some form of influence, and so you're very protective of that. And so I think that And I think that's part of it, which is like, if, how did, with everything that you're doing with LadyBrains, it's connected to networking, it's connected to, you know, making those connections. And I guess that's what we get to do every day with the podcast is it's as much about us having a reason, excuse to chat to you two than it is to communicate to the audience as well. So I think that that's, it's the very long game. Yeah. Doing great work. And hopefully that great work turns into cash, maybe.

Tommy: Diversifying your income too. It's like it can, there is other ways.

Caitlin: Totally.

Tommy: Within the business. I mean, look at you guys, look at you girls. It's the supper club.

Harry: Yep.

Anna: Events.

Tommy: Yeah. You could see that's like, you know, the size of those and the scale of that. It could be a direct reflection of how big the brand Ladyland becomes, you know?

Josh: Events in every single— I could imagine Melbourne, Sydney, New York, all simultaneously, all happening like at the exact same time. Have you done that yet or have they all been local, like hyperlocal?

Caitlin: They've been hyperlocal. And I think the challenge with that is like we personally are there driving everything and we can't be, you know, in 3 places at once. And so we've run events in all 3 cities, but never sort of at the same time. And we're trying to think through how we connect like the startup pubs digitally as well.

Anna: And also we've spoken about doing kind of Ladyland Lives on a bigger scale. You know, we've done some with like 30, 40, 50 guests, but how do we kind of go on tour and, you know, do them in Sydney, Melbourne, Perth, Adelaide? That's, that's another, you know, opportunity.

Caitlin: Well, yeah, I think the hardest thing, the great thing, but the hard thing is like there are so many ways that you can take it. This, you you know, the podcast is merely the platform and the brand platform and a marketing tool really. And you know, you off the back of that build a community, whether you're driving that or not. There is a community of listeners who are like-minded because they're listening to your podcast. And then it's like, well, what do you do with that? And, um, I think Jo Horgan from Makeup just was so amazing in her advice to us. She's like, the art is not in generating the ideas, the art is in the editing down of ideas. And that's the process we've been going through for the last months. It's like, how do we edit down all of these ideas in a way that makes sense?

Tommy: To then execute on the ones that really mean something?

Caitlin: Exactly. To choose the one or two that you execute and go after.

Josh: Can you execute and edit at the same time? Is that what iteration is?

Caitlin: Yes.

Anna: Yep.

Caitlin: Yep.

Harry: Yep.

Josh: You can.

Anna: Definitely.

Caitlin: Yeah.

Josh: Ladyland, the next episode, who's joining you? You know, next week?

Caitlin: Next week we have Sasha Benz. So she is an Aussie Bondi girl who lives in the Hamptons in New York.

Tommy: Two horrible places.

Anna: Bondi, the Hamptons.

Josh: They're beautiful. What are you talking about?

Caitlin: That was an experience. So we went out to the Hamptons and interviewed her, and that was—

Josh: is that 97 Laughing or Harry?

Caitlin: Sarcasm at its finest.

Anna: Oh yeah, great.

Caitlin: But she's got 4 or 5 businesses. Yeah. So she's like got 2 kids, 5 businesses.

Josh: She's got—

Caitlin: she's building a tech business. She's got 2 retail stores. She um, has a blog, has a blog that she, yeah, makes money from.

Anna: She's the creative director of the Surf Lodge, which is this kind of like crazy venue in the Hamptons where like all the kind of celebrities go and they have, um, you know, performances, music performances over summer.

Josh: Amazing.

Anna: So yeah, it's pretty—

Caitlin: we saw Lupe Fiasco. Yeah, it was pretty good.

Tommy: Is this like a big venue? I was thinking like an old-school lodge style.

Caitlin: Well, it's not It's an old school sort of lodge in look and feel, but because it's in the Hamptons, you can imagine the clientele. So it's like a hot pot of celebrities and they have, you know, the best acts. Like Beyoncé was there when we were there.

Anna: Yeah, no big deal.

Caitlin: Just drop that one in there. We actually were recording the interview with Sasha and she had to go because she was getting a call from Beyoncé's people saying Beyoncé is like coming to your store.

Anna: She's like, quick, wrap this up, mate.

Josh: What did that do to your headspace? Because like even us being in in LA, like you have this sort of idea and you get into the rah-rah and all that sort of thing and then you come back. People are living big, really big. So what does that do? What does that do psychologically? Like, does it stretch your minds? Does it?

Anna: Yeah, I think it does stretch your mind. I think, you know, you kind of, you get used to working in your own town, city, and then you kind of go overseas and you're like, wow, like there's just, people are living large. I think of it more in terms of like opportunity. You know, there are people over there that are also building incredible businesses that we want to talk to. And yeah, like getting a call from Beyoncé's people, it's just like, yeah, that was a bit of a what the fuck moment, not gonna lie.

Caitlin: Like being interrupted because Beyoncé's in town, that was a moment where I was like, how did we get here?

Anna: Yeah, seriously. Like, how did we get here?

Caitlin: How did we get here?

Tommy: Where is Beyoncé going?

Anna: Because we jumped on our bikes and we were cycling around the Hamptons for a little while. We didn't find her.

Tommy: She came in on the chopper.

Anna: Yeah, yeah, yeah, exactly. But yeah, it's, it's, it's a kind of a pinch me, like, what are we doing? But, but at the same time, it's like, everyone's the same, everyone's normal. Like, you know, she's an Aussie, like, she's an Aussie over there, and you know, she's, she's, um, built, you know, some successful businesses, and you know, Beyoncé wants to get in touch, and it's kind of like any— it's anyone's game. Anyone can do that, you know. So yeah, there's a part that's It's like, you know, it's aspirational and it's unattainable, but then at the same time you're like, holy crap, that could actually be anyone.

Josh: Yeah.

Tommy: I think that's the learning for me going overseas is seeing the possibility and reevaluating what possibilities look like for us and what we're doing. So it's a good perspective shifter.

Caitlin: Do you think that it has made you realise you're thinking too small? Like, is that what you came? Yeah.

Tommy: It's what happens a lot of the time. I think about, well, it's also the, the size of this country and the amount of people here is so small in comparison. So a small piece of the pie over there is bigger than the whole pie here.

Caitlin: Yeah.

Tommy: And so that's where it's like, yeah, maybe you do start looking internationally. It is that. Yeah. So, but then it's the hard bit is how do you bottle that and And bring it back.

Josh: Yeah.

Tommy: How do you bottle that and call on that feeling?

Josh: Like, but also like, Anna, to your point before, it's like you have to work for every dollar. And so the idea of having these big dreams, you actually need to think small. You need to make like a dollar before you make 10 and, you know, 10 before 100 and 100 before 1,000. And so it's very easy to see these big things and try and create a roadmap to that, whereas like it is the painful truth of you just have to like start small and keep going even to get to the big thing.

Caitlin: Yeah, totally. My mum has built a business for the last 25 years and that was her one piece of advice. She's like, start small but always think big. Because if you get, if you're thinking big, you can get caught up in that and you're like, how the fuck am I going to get there? And then you don't do the small things. Whereas if you focus on the small things, one foot in front of the other, it's kind of like the balance between the two.

Anna: And I think we're what we're really good at is goal setting. So the goal setting is the day-to-day or the small steps that we're just talking about, like, okay, what do we actually need to achieve? But all those small steps, as I said before, are getting you to that endgame, and that's the big vision. And we have big visions. We've got, we wanna build a global business, but you can't go there straight away. You have to take all the smaller steps, and we do that by just having really strong, strict, clear goals.

Caitlin: Yeah, we work in 3-month blocks.

Anna: So we work in 3-month blocks and then we do 2-week sprint cycles.

Josh: Where are you at in the 3 months?

Anna: We're starting just December, January, February. So we've just started an entirely new, um, 3-month block. And yeah, we're into the 1 week, first week of the 2-week sprint cycle. So right at the beginning, pretty clear. Like, you know, I think you have to, you have to have some kind of accountability. You have to be setting goals because otherwise you're kind of shooting from the hip and you're not getting anything done.

Caitlin: And it's been good because with that 3-month plan, it's like, for me anyway, you know, it stops me from going off in a million other directions, which is my natural state.

Anna: Bring it in.

Caitlin: So she's like, Anna, we've got 3 big things we want to do.

Anna: It's on the goal setting plan.

Caitlin: Like, fuck, all right.

Josh: Yeah, I think it's awesome what you're building, especially like Ladyland. The other day I was listening to it on the way to work and then came back, and before the guys were talking talking, I had to write down all the notes of the things I was learning because it was— I think you've done a great job of packaging it up. But also I think the ending where you talk about these are the takeaways, I think is like really powerful because sometimes we don't synthesize, we do a shit job of being able to do that. And so I think that's really powerful too.

Tommy: I think we throw it over to Harry to get his takeaway from the episode.

Caitlin: Yeah.

Josh: What's the takeaways, Harry?

Anna: Harry? I don't know, he's been asleep.

Harry: No, I haven't.

Josh: No, I haven't.

Harry: Um, I don't know.

Josh: What have you found inspiring about Anna and Kate, do you think?

Harry: I think the goal setting and how if you have your goals, you're more likely to achieve them rather than not putting them down, like listing them. Yeah, if that makes sense.

Josh: Yeah, it was the last thing they said.

Caitlin: Yeah.

Harry: No, no, like, that was what I was thinking about.

Tommy: Work experience is all about pushing yourself.

Caitlin: One other.

Tommy: Yeah, come on.

Anna: I'm happy if you take that away. Great. Yeah, go write down some goals.

Josh: What about you, 97?

Harry: You're not?

Mason: No, probably, probably the whole building a global community and connecting all these central hubs. Yeah, I think I felt like that really resonates with what we're doing and we're super inspired by that. So I was really stoked with that. That was awesome.

Josh: All right, there we go. That's a daily talk show. Yeah, definitely cheque out Ladyland. Apple Podcasts.

Harry: Your phone's buzzing too. I think it's Beyoncé.

Josh: I can't tell.

Anna: Yeah, I was expecting a phone call from her.

Josh: Actually ringing, or was that all banter? Okay, so how do you know whose bag's whose?

Harry: Yeah, well, Caitlin put hers there and she said it had the mints, so, so I eyed it off.

Tommy: Yeah.

Anna: Oh, he's been going rummaging through the bags. Hey, we were all a bit distracted over here.

Tommy: His breath is fresh though.

Josh: It's the Daily Talk Show. If you've enjoyed the show, feel free to share it on Instagram. Otherwise, we'll see you tomorrow, guys.

Tommy: See you guys.