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Ep. 36 Okay Sis’s Mady Maio on Why Founders HAVE to Prioritize Mental Health

Ecommerce Building Blocks · 2022-09-21 · 23 min

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Key moments - from our scoring

Substance score

24 / 100

Five dimensions, 20 points each

Insight Density6 / 20
Originality5 / 20
Guest Caliber5 / 20
Specificity & Evidence4 / 20
Conversational Craft4 / 20

Mady Maio brings a refreshing perspective on founder wellness, challenging the pervasive hustle culture narrative that dominates startup spaces. As co-host of OK Sis - a four-year-old podcast exploring mental health, entrepreneurship, and female sisterhood - and founder of Camber, a travel recommendation app in public beta, she articulates why emotional preparation matters as much as operational planning. Drawing from interviews with dozens of female entrepreneurs, Maio identifies that female founders face compounded challenges: only 2.5% of venture funding flows to women, creating additional emotional and psychological friction when entering male-dominated fundraising rooms. Her antidote isn't spa days but rigorous inner work: weekly therapy, daily meditation and journaling, shadow work, and consistent emotional check-ins with her co-founder Lauren. She actively rejects the notion that successful founders must work 12-hour days or sacrifice sleep, instead advocating that three hours of deep, focused work outweighs nine hours of unfocused effort. For Camber specifically, she discusses niching into Los Angeles recommendations via TikTok, targeting the gap between tourists wanting local insights and residents seeking rediscovery. Her framework for co-founder relationships - treating weekly emotional check-ins with the same rigor as budget meetings - offers practical infrastructure for sustainable partnership.

Key takeaways

  • →Female founders receive only 2.5% of venture funding, requiring emotional preparation alongside operational readiness when fundraising in male-dominated spaces.
  • →Effective self-care for founders means therapy, meditation, journaling, and shadow work - not spa treatments - and directly supports business performance and mental clarity.
  • →Three hours of deep, focused work consistently beats longer hours of unfocused effort, contradicting the manufacturing-era eight-hour workday model inherited by modern businesses.
  • →Weekly emotional check-ins with co-founders should be treated with equal priority to financial and marketing meetings to prevent resentment and communication breakdowns.
  • →Redefining personal success metrics (moving the needle even one centimeter) rather than accepting society's definition creates sustainable productivity without burnout.

Guests

Mady Maio

Topics in this episode

Burnout preventionhustle cultureFemale founder funding gapventure capital fundraisingTikTok content strategyshadow workOK Sis podcastCamber (travel recommendation app)daily meditation and journalingco-founder emotional check-ins

Questions this episode answers

What percentage of venture funding goes to female founders?

Only 2.5% of venture funding goes to women founders, creating a significant disparity that female entrepreneurs must navigate emotionally and strategically when raising capital.

What does Mady Maio mean by self-care for founders?

She means therapy, meditation, journaling, shadow work, and consistent inner reflection - not spa days or leisure activities - as essential tools for mental clarity and business performance.

What is Camber and how does it work?

Camber is a travel recommendation platform that allows users to share favorite places with friends through a streamlined social interface, with current focus on Los Angeles recommendations; it's available in public beta on TestFlight.

How often should co-founders have emotional check-ins?

Co-founders should have weekly emotional check-ins on the calendar to discuss gratitude, worries, and mutual support needs, treated with the same priority as financial or marketing meetings.

How long has the OK Sis podcast been running?

OK Sis, co-hosted by Mady Maio and her sister Scout, has been running for nearly four years and features conversations with female guests about mental health, entrepreneurship, pop culture, and sisterhood.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

6 / 20

The episode occasionally surfaces a useful tactical idea (weekly co-founder emotional check-ins) and a nuanced reframe of self-care, but the overwhelming majority of airtime is filled with platitudes about hustle culture, journaling, and drinking water - advice any founder podcast listener has heard dozens of times. Insight per minute is very low for a 23-minute runtime.

We have emotional check-ins every single week on the calendar. And what these are, you know, We talk about things that we're grateful for in the business, things that are worrying us, things that we need from each other.
I invest very heavily in self-care. And when I say self-care, I don't mean like skincare and like bubble baths. I mean, I mean therapy.

Originality

5 / 20

The anti-hustle-culture position and the 'redefine success for yourself' framing are both extremely common in founder content by 2023; nothing here is contrarian, first-principles, or counterintuitive. The co-founder check-in cadence is a practical suggestion but hardly a novel framework.

I do not subscribe to hustle culture. I do not like to work 12 hours a day
did I move the needle even one centimeter today? Great. I was successful.

Guest Caliber

5 / 20

Mady Maio is a podcast co-host and early-stage app founder whose product is still in public TestFlight beta and pre-seed fundraising - she has not operated anything at meaningful scale and speaks largely from lived feelings rather than proven operator experience. She is closer to a content creator than a B2B practitioner.

we are in a public beta right now on Test Flight
Never been a product manager before.

Specificity & Evidence

4 / 20

The episode contains almost no hard data; the only concrete figure offered is the well-circulated '2.5% of funding goes to women founders' statistic, cited without a source. The app description, growth claims, and mental health advice are all kept at a vague, anecdotal level with no metrics, timelines, or dollar figures.

something like 2.5% of funding goes to women founders
we built this awesome app that allows you to share your favorite places with friends

Conversational Craft

4 / 20

The host asks broad, open-ended questions, consistently validates rather than probes, and at several points hijacks the conversation to share his own experiences at length. There is zero productive pushback and the episode closes with an irrelevant 'hot take' about food leftovers, squandering the final minutes entirely.

I love that. And really build at your own pace.
I love that. And, you know, I've gotten the pleasure to meet with so many amazing female entrepreneurs

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

founder18founders15female14building13show11feel11build11love10hear9podcast7mental7whole7health6entrepreneurs6process6trying6

Episode notes

In this episode of Ecommerce Building Blocks, Jason is joined by Mady Maio, host of the popular business and lifestyle podcast Okay Sis and co-founder of the travel recommendation app Camber. Jason and Mady talk about mental health for founders and entrepreneurs: why it’s so important and what all of us can do to make sure we use our well-being to show up for the projects we love and ourselves every day. Jason and Mady start their conversation by talking about the particular challenges that face female founders and entrepreneurs, and why preparing mentally and emotionally is crucial to balance and success. Mady shares what self-care looks like (NOT bubble baths) for her and how this plays into her definition of success. In the second half of the episode, she and Jason talk about Camber app, what it has to offer, and how Mady has navigated her relationship with her co-founder through inventing, building, and finding investors for this project.

Full transcript

23 min

Transcribed and scored by The B2B Podcast Index.

Being able to connect with other female founders is what has saved me and also what propels me forward because you realize how you are not alone. In order to avoid burnout, I invest very heavily in self-care. And when I say self-care, I don't mean like skincare and like bubble baths. I mean, Hello, everyone.

Welcome back to another episode of the Building Blocks podcast show. Today, I'm joined by Maddie Mayo. Welcome to the show. Hello, Jason.

Thanks for having me. You've been busy. You've been building, right? I've been building.

I've been building. Yes. And I did a little research, a little homework on you. You have also a very successful podcast called OK Sis, where you talk about mental health issues with female entrepreneurs.

Am I getting that right? You are getting that correct. I've had a podcast. I do it with my sister, Scout.

We're coming up on four years. So it's been a long time. And yeah, the premise is we bring in a rad female guest every single episode to join in on the sisterly banter. And we believe that women should be multifaceted individuals.

So we talk about anything from pop culture, mental health, female entrepreneurship, and sisterhood. I love that. I love that. And, you know, I've gotten the pleasure to meet with so many amazing female entrepreneurs, actually interview a lot of them on the show.

And a lot of them really felt that this space need more of them. You know, like there wasn't really a platform for them. They kind of had to fight a lot harder to get the same attention. and mental health in general for both sides really just was really not talked about.

And I know a lot of founders who struggle with mental health. So those are some of the points I want to touch on on today's show with you because you obviously have a lot more exposure. Tell me a little bit more about like all the female entrepreneurs that you have interviewed so far. What has been like the most common topic to talk about?

Yeah, I mean, you know, although we bring in a lot of female founders, similar to kind of how your show is like it feels more of a conversation than like an interview um obviously we get into things both me and my sister are entrepreneurs we have our own companies so we'll ask things like selfishly from like business standpoints but really it's mostly about them as individuals a lot that touches on mental health lifestyle and the way that they're navigating this like very, very unique and intense experience that is entrepreneurship.

And across the board, I think, and something that I've experienced also being my own founder, my own right is being able to connect with other female founders is what has saved me and also what propels me forward because you realize how you are not alone in the process. I think as a founder, it can be very lonely. You feel like, holy shit. I, Oh, can I cuss on this?

I hope I can. Yeah. Yeah. Yeah.

Yeah. Okay. Good. It's going to come out a lot.

Um, so, you know, as a founder, it can get really lonely in terms of, uh, you know, every day you're faced with something that you have absolutely no idea how to do and that you're trying to figure out. And when you look online and you look around, you're like, everyone else has everything figured out. Like, am I doing something wrong. Whereas when you tap into that network of female founders and of women, they're so willing to help one another.

And there's this incredible support system that comes with it. So that's kind of what I've found. People are so quick to help one another and build each other up. There's so much room at the table for us.

There's so much space. And I've been just so fortunate connecting with these founders because it feels like this amazing network that I can tap into for any question that I have about building a business. I love that. And what would you say is like the most common hardship facing female entrepreneurs that aren't really talked about?

I mean, raising money, I hear a lot. I'm kind of starting that process. We're going to be raising our pre-seed round for Canberra. And I'm honestly, like, obviously I'm preparing from a like operational standpoint and a logistical standpoint, but I'm also preparing emotionally.

And I don't think a lot of people talk about that. There's a ton of limiting beliefs and rejection that comes with it, of course. And then there's also just, you know, there aren't a lot of female founders that are raising money. I think something like 2.

5% of funding goes to women founders. So there is, there is definitely a lack. And so when you're, entering these spaces that are heavily male dominated, it's very emotional and it's very taxing on, you know, yourself and yourself as a leader and trying to convince people that, you know, your, your business is something separate from your gender. So, um, I hear that a lot.

I hear that that process is pretty grueling and pretty intense. So I kind of, as I prepare for that, I'm not only preparing like, you know, for the deck and the pitches and all this, like I'm actually preparing internally, which I don't think people talk about that. The emotional side of business and of entrepreneurship is usually not as highlighted. I think it's one in the same.

I think you cannot have one without the other And people need to know that before they jump into this type this type of a career path No I I totally see that And it a whole it like an invisible battle Like you come into the pitch meeting, knowing that you are somewhat at a disadvantage statistically, you know, and you kind of have to fight for your own position there. Um, let's talk a little bit more about, you know, how founders in general can, can improve their mental health.

And I feel like recently that's been talked a lot more about a lot more founders are getting burnt out i want to hear your thoughts on from all the conversations that you've had and even yourself personally what are some things to avoid burnout yeah i so i've been like very which i'm trying to destigmatize i'm trying to speak more about because i think it's really important but there is this glamorization of the founder journey and definitely uh you know there's this hustle culture mentality that has enveloped the whole founder space.

And I, I do not subscribe to hustle culture. I do not like to work 12 hours a day or even fit. Like I do not like, I like to have my sleep. I can't, you know, I like to be like prepared and mentally there in order to work at my optimal efficiency.

And I personally, I think that there's this narrative that founders have to, you know, there's like a stereotype, they have to pull all nighters and eat ramen noodles. And it's like, I don't, I don't feel that way about my lifestyle and about what I'm building. I also don't think my, my company would be successful if I were operating like that. So to me, in order to avoid burnout, I invest very heavily in self-care.

And when I say self-care, I don't mean like skincare and like bubble baths. I mean, I mean therapy. I mean like deep inner work. I do like a very intense manifestation and like shadow work process.

I go to therapy very, very regularly and consistently. And it's not fun. I'm not, you know, I think people have misinterpreted what self-care is. And they think it's like a fun, like restful, like spa day.

That really is not what I'm talking about. It's like actual reflection and taking time to restore yourself. And that doesn't, again, that doesn't mean sitting on the couch and watching TV. That means going on a walk meditation.

I meditate every morning. I journal every morning. I drink a shit ton of water. Like I, I move my body and I don't, I don't work out for like physical things.

I work out for like the mental clarity. So there are just ways that I make time for all of these building blocks that allow me to show up for my business, my business, show up for the podcast and show up for myself. I just personally, I love to read. And, you know, I stopped work and I read in the evenings.

Sorry. Like I'm not, I'm not spending my whole evening working on my business. And I think that's really true. It's like, I even feel I'm like getting like schvitzy and like sweaty, even saying that because I feel like people are going to come for me and like you're a bad founder where it's like, no, that's the way that I recover from a day of intense work and focus.

And that's just how productivity is to me. I think something I'm learning, I definitely do not have the answer to this, but I have been trying to redefine what success and productivity mean to me. I think I've been heavily influenced on what society means of success and how they define it. And, uh, the money aspect that is attached to what success is, But lately I've just been like, look, did I did I move the needle even one centimeter today?

Great. I was successful. That was it. Like, I think I thought before, if I'm not exhausted at the end of the day and my eyes are like bleeding from looking at screens all day, then it wasn't a successful or productive day.

That's just not how I want to live day to day. So I've just been fine tuning that a little bit to what feels good to me. I love that. And really build at your own pace.

You know, I'm not sure how long you've been in business. I assume many, many years. Early in my career, I also thought that I need to be grinding 18 hours a day. This whole Silicon Valley tech hustle culture that I was trying to fit in.

And I wasn't in tech. I was in CPG. But at the end of the day, you look back and say, was it worth it? Like, did I move the needle?

and you're so exhausted you can't even think about that right um and i would say like you know three four hours of really deep valuable work beats way much of nine 12 hours of work that you feel like you just have to work on and then you look back and said did i do the same or did did i actually make incremental changes and oftentimes you find that many of those hours are wasted. The whole eight hour day week is, or a work day. It's, it's something that was created back in the day for, for manufacturing automobile.

It was not meant for today's generation of work. So, you know, I love that you are able to set your own pace. You, you know, that what you want to manifest and you write that down every single day. Um, I think that's wonderful.

It's good to hear more entrepreneurs talk about that. It's good to be vulnerable, really, um, lay all your quads out and say, this is who I am, this is how I'm going to build my business. Whether or not you like it, that's up to you. But that's how I'm going to build my business.

Speaking of building businesses I also did a little bit digging You also are currently working on amongst many different things a new app Can you tell me more about that Yes So I am currently building a platform called Camber It's a travel recommendations platform. Basically allows you to share your favorite places with your friends. And the way that this idea came about, my co-founder and I, she was actually my first boss out of my first job out of college, which is really funny.

And so we worked really well together and we knew that and stayed in touch. Always knew we wanted to build something together. I think I've always had this like entrepreneurial bone within me, but I just didn't know what that idea was. And so she, I was always that friend that she would text for recommendations.

She'd be like, Hey, I just saw that you went to Austin on Instagram. Can you send me a Rex? And I'm sure you and everyone listening has either like received or sent a text like this. And I would send her a shared notes screenshot or like a Google doc.

And it was just this completely disjointed process. And we just thought, like, why isn't there a more streamlined way to share these like amazing places and create more of like a social component? Like a lot of our generation might have Google Maps lists or have things saved or even screenshot things of like Instagram. And there isn't this beautiful interface to organize all these places.

And then also that social and community added element to follow your friends and see where they recommend. So we sought out to build Camber. This was about almost three years ago, which is wild. Yeah.

So we worked with an agency to do the UI UX and the development and kind of product managed this whole thing. Never been a product manager before. Again, you'll kind of hear this common theme that anything I've been doing with Gamber has been like the first time doing any of this. Like I'm like HR, I'm a product manager, I'm a marketer.

Like just everything is a brand new experience, which is very fun and also very humbling. But we built this awesome app that allows you to share your favorite places with friends. And we are in a public beta right now on Test Flight. So anyone can download the app, test it out, have fun, add your favorite places.

And we just wanted to create this awesome community that really values cool spots. And the biggest growth I think we've seen has been the TikTok. So I think either people listening probably have seen my face on TikTok. It was funny that you said, like, it's good to be vulnerable.

Like I have been very open on the internet for a very long time. I think it started with okay. Sis. And then I feel very comfortable opening up on the internet, putting myself out there.

I think it's not, it's really not something that it's something I talk about a lot that when you are a founder, you're suddenly a content creator. Like you're suddenly a brand in your own right. And on top of actually building a business, you're now like having to build this personal brand. Um, especially as a female founder, I think every female founders basically expected to be the face of the brand to be their own personal like leader or, you know, thought leader, if you will.

So we started building the tick tock and niching down into Los Angeles specific recommendations. And that is where we really started to become like a trust, trustworthy resource for people in LA to find cool things to do and places to be. And that's going to be really our strategy. Cause I think we, we definitely hit, hit like scratched a niche that I think people in LA have been missing where it's like, where do I go to find these cool new hidden gems, but also like cool spots.

Um, there's such a great discovery element that happens in LA. So once we finalize that formula here, then we'll roll it out to other cities. But you can still use the app in other cities for sure. But definitely the content, the community is LA based for now.

I love the tagline. I'm just gonna read it here from the website. It's for tourists that want to feel like locals and locals that want to feel like tourists. That's that's beautiful.

Yeah, we call our community local tourists. There you go. Yeah, I feel like when you live in a place for so long, or you like you grew up there, you don't really explore. Like I remember like being, you know, when I was in Toronto, people were like, Oh, did you go to this place?

I'm like, Oh, never, never heard of it. But apparently everyone talks about it. So I love that this is a bridge between the two types of people that often come to LA. There's a lot implants, and there's a lot of locals.

And, you know, sometimes you just want to make the switch. um exactly i i want to talk a little bit more about working with a founder you know at early stages what are some of the challenges that people should be aware of when they have co-founders there's obviously a lot of ups and downs of having co-founders what are some things that you feel like have surfaced so far and how how are you combating them yeah a co-founder relationship is to me it's been the driving success of what camber is um there is a as i mentioned being a founder and starting a business is incredibly taxing um emotionally and mentally so having someone there to either bounce ideas off of or debrief after a call or be able to just like be like, what the fuck was that?

You know just there just all these little moments that happen and I get to experience and share them with my co Lauren So that has been I mean I wouldn have started it if I didn have this person. Like it's just been so integral to, to the whole success of, of what we're building. And then I guess like a challenge is just dividing up tasks and you know, in the beginning, we kind of did everything together and made decisions together, which is obviously, you know, in the beginning, when you don't really know what you're doing, it's, it's great to have that person.

But now we're at the stage of the business where we're kind of figuring out, okay, like, actually, you probably don't need to come on every podcast with me, you know, maybe I'll be more of the forward facing founder, and you're more the operation. So it's been interesting to divide up those camps and realize our strengths and realize where we can lean on each other for support or come together when needed. But that's been just a new shift, I guess, in the dynamic lately. But other than that, it's been an incredible support that I think, again, as female founder as a founder in general like to have that person like along for the ride with you to celebrate wins to also like like process losses anything like it's just it makes the journey more exciting I love that and you seem so happy to talk about your co-founder which is really really good to hear yeah it's like a marriage right like you're you're gonna go up and you're going to go down together.

So make sure you find a good partner for it. And then also, I mean, for anyone listening who has a co-founder, I, again, I keep talking about the emotional side of business only because I think it is as important, if not more important than like any part of the business. We have emotional check-ins every single week on the calendar. And what these are, you know, We talk about things that we're grateful for in the business, things that are worrying us, things that we need from each other.

And the reason that this has been so important is that it doesn't let anything build up. Any resentment, any little thing, maybe like a communication error or something, relay it all out on the table during that week and don't let it build up to the next week. I think that is such an important practice that if you are in a co-founder relationship, putting that on the cowl and it should be treated with the same respect as a like financial, you know, looking at the budgets meeting or like a marketing meeting.

Like it should be something that you guys really, really commit to because it's allowed us because you, again, you don't really know. Like there are moments where she'll be like, hey, the way that you said this or like maybe I need your support on this area. Like you wouldn't have told me that just in a regular day. Right.

So I just think it's really it's a practice and a thing that we've been we've been doing that I really recommend. and and really like the downfall to any type of relationship whether that's romantic or business it's not having communication channels opened up and things bottle up and there's resentment and there's like oh i thought you were doing this how come you weren't doing that and then and then things fall apart so it's good that you treat that one-on-one as important as a finance meeting because truly it is and that's really why i want to bring you on to the show is to talk about the side of business that people don't really talk about it's not the sexy side of the business, but it's the bloodline of your business if you do it well.

So I appreciate you giving that tip here. One last thing before I let you go, I want to give you 60 seconds to tell me your hot take. Okay. This is going to be really hot and I hope I don't get canceled for this.

I hate leftovers. Like food? Like food leftovers. Why?

everyone's like what are you talking about you're the best i just it's never as good as the first day you have it and it just like tastes funky i don't know i'm just like everyone loves leftovers and my hot take is that i i don't i mean you have standards for your food and there's that no one's gonna fight you on that there we go that's what i like to hear that's that's what i didn't expect but one that i love to hear because that's so new um well maddie thank you so much for coming on the show i wish you the best and your podcast show um and your new app it looks amazing i'm traveling for the next few weeks so i'll actually be logging in and see if i can you know make some content around asia i'm going to singapore oh my god please yes because because you're right like i'm tired of screenshotting i'm tired of like saving to my collections and like sending links to people that I'll never discover again.

And then like just hours ago, I was asking my friend to send me an itinerary for this country that I've never been to. And it's still very not streamlined. So you're right. I see the problem.

I'm your customer and happy to download on test flight. Amazing. Thank you so much for coming on and hope you have the best week. Have a good week too and enjoy your travel.

You just heard an episode of the Building Blocks podcast. If you like what you heard, subscribe below to keep hearing conversations that I have with brilliant marketers, founders, and innovators on how they build their best ideas. Now, if you want to learn how you can turn your best ideas and build something massive out of it, visit my website bbclass.co or follow my Twitter at aggro.

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