Built on Purpose, Running on Empty: Values, Burnout, and the Theology of Hard Times with Catharine Montgomery

What happens when the mission that fuels you becomes the thing that depletes you? In this episode, Nicole sits down with Catharine Montgomery, founder of The Better Together Agency, a communications firm built to amplify organizations doing good in the world. Catharine has rebuilt her business — and herself — more than once, and she doesn't hold back about what that actually costs. This is a wide-ranging conversation about purpose-driven entrepreneurship, the burnout that hides inside your passion, and what faith traditions have always known about rest that hustle culture refuses to teach us. If you're a values-driven founder, a woman of faith navigating hard seasons, or someone who has quietly wondered whether your sense of purpose is sustaining you or slowly burning you out — this episode is for you.

Here's what's in the episode:

• What it really looks like to build a business around your values
• The shadow side of purpose-driven work: how caring deeply can quietly become the reason you stop taking care of yourself
• Bias in AI, and why Catharine built her own tool
• The theology of hard times: does God have a plan, does it have to be detailed, and what do you do when you've stopped believing it?
• Simple, unglamorous rest practices that are actually working for her right now

Chapters:

00:00 Introduction to Just Rest and Catharine Montgomery

02:09 Taking a Deep Breath

03:17 Catharine's Burnout Stories

05:13 The Birth of Better Together Agency

08:37 Navigating Racism and Burnout

11:20 Building in Everyday Self-Care

14:23 Spirituality and Personal Growth

16:57 The Nature of Divine Planning

19:19 Understanding Suffering and Divine Presence

21:49 Evolving Values-Alignment in the Second Start-Up

24:37 Navigating Change and Maintaining Mission

28:48 Innovating with AI for Social Good

32:50 Addressing Bias in AI Technology

35:28 The Impact of AI on Racial Wealth Gap

37:42 Perfectionism and Its Challenges

41:08 Balancing Passion and Burnout

44:31 The Importance of Rest and Creativity

48:47 Highlighting Positive Change: Red Rabbit

CONNECT WITH CATHARINE MONTGOMERY:

Website: https://thebettertogetheragency.com

LinkedIn: https://www.linkedin.com/in/cnmontgomery

The Better Together Agency on Linkedin: https://www.linkedin.com/company/thebettertogetheragency

Organization highlighted: Red Rabbit — providing culturally relevant meals to children in schools across New York, Philadelphia, and Washington, DC. redrabbitlunch.com

CONNECT WITH NICOLE HAVELKA:

Newsletter: https://defythetrend.substack.com/

LinkedIn: https://www.linkedin.com/in/nicole-havelka-35762022/

Work with Nicole: https://defythetrend.com/contact/

The Calm Calendar Club is a brain-friendly planning community for neurodivergent adults, ADHD minds, and sandwich-generation caregivers who are tired of systems that don’t fit real life. We help you build a flexible, values-based calendar that reduces chaos and protects your energy. This low-cost, community-based program is ready for you at defythetrend.com/calm-calendar.

Thank you to the people who helped make this show happen.

Send me a message via Speakpipe.

A proud member of the Feminist Podcasters Collective.

Transcript

Introduction to Just Rest and Catharine Montgomery

SPEAKER_02 0:00

Welcome to Just Rest, burnout tips for everyday radicals who are tired but not giving up. I'm your host, Nicole Havelka, bringing you tips and inspiration to help you feel seen and supported on your radical rest journey. Let's go. Hi, hello, Rest Troubles. Welcome to Just Rest, where burned out change makers come to remember they're not alone, to get permission to rest without guilt, and inspiration for showing up without burning out. And I am so delighted today to have with me Catherine Montgomery, the founder of the Better Together Agency. And this really sort of goes without saying, but as a black woman, she knows what it means to face really big challenges. She saw firsthand how bias and systemic barriers try to keep people from making a difference. But listen to this: instead of giving up, Catherine realized those obstacles were actually a chance, an opportunity to do something better. And she decided to use her forte, communications and technology, to make the world more fair and equal. How cool is that? I'm so excited about that. And that's how the Better Together Agency was born. And they believe that powerful stories can connect people, challenge old ideas, and inspire real positive change. And that's what we're all about here on Just Rest. And I knew that we would be a really good fit for being on this podcast together. And um Better Together Agency is based in Washington, DC, but serve clients all over the country. And I am so excited and stoked to have you here, Catherine. Welcome.

SPEAKER_01 1:53

Thank you. I'm excited to be here.

SPEAKER_02 1:55

I'm so happy that you made the time to join us. Of course. So before we get started, I like to do one thing for us and for the listeners out there is to take one deep breath

Taking a Deep Breath

SPEAKER_02 2:09

before we get started and launch into the rest of our conversation. Does that sound good?

SPEAKER_00 2:14

That's perfect. For sure.

SPEAKER_02 2:17

For sure, we all do. So I would invite you to maybe, you know, make a comfortable seat, feel your feet on the floor, and then take a deep and slow long breath, making it kind of fuller, maybe is feels right for you.

SPEAKER_03 2:31

Taking an inhale. And an exhale.

SPEAKER_02 2:51

Maybe pausing for just a moment to kind of feel the changes, the shifts and changes that happen in the body. They always happen to happen to me, and I know I always feel better for having done it before I get started. And it's a great way to model us taking a pause, right?

SPEAKER_03 3:10

I love that.

SPEAKER_02 3:11

Yeah, yeah. Oh yeah. It's one of my favorite things. So

Catharine's Burnout Stories

SPEAKER_02 3:17

uh as of this recording, I'm nine episodes in of recording anyway. This will be the ninth episode. And one thing I'm noticing is that I think that every entrepreneur, regardless of the field that they're in, like what kind of business they have, they have some kind of burnout story. And and so I would love to talk with you about kind of your pivot points. It was one was originally starting the agency, right? And then there was another more recent pivot changing from uh working with the venture capital company that you had um that had been funding you in the initial startup. So, and maybe there's other places in between or before after there that you want to talk about too. So take that in any direction you would like. But I'm wondering like, what has really prompted these changes? So um let's start by sharing a little bit of your story.

SPEAKER_01 4:15

Yeah, I mean, the first pivot became uh came because I was being uh someone was being racist toward me at my aid the agency I was working at. And it was progressive agency, which is really interesting. But I wanted to work at an agency but also make a difference. And I found this uh boutique agency in Boston. Um, and three years in, a woman started just, you know, in writing, being racist toward me. And, you know, it took them five months to say, oh, we don't find didn't find any signs of racism. And then they gave her a raise of promotion the month after, and I just felt like this is the time I probably need to leave. Um, but I had a friend who said, you know, you need to get a buyout, things like that. So I ended up hiring a union attorney because we were unionized and um got everything I asked for in the buyout, things like that. So I was at a point where I wasn't sure what I wanted to do next, and I had never thought about starting an agency. It wasn't that I thought I couldn't do it, it's just

The Birth of The Better Together Agency

SPEAKER_01 5:13

something that wasn't on my mind. Um, and I was on a Slack channel called Ladies Get Paid, and a recruiter posted, which is like 50,000 women from around the world. So it's just you ask questions, you help each other. Um, a recruiter posted that a VC firm um wanted to move into the US and they only back public relations agencies. And I was like, that's so sketchy. You don't need uh VC funding to start an agency, you just kind of start it. Um but I met with her, we hit it off, you know, I met with the two investors that week and uh wrote a business plan. Uh, had to Google how to do that. Um, and there was no Chat GPT yet, you know, it was like two months before. But I had to do it myself. Um, presented it to them, and you know, the only thing I knew was that I wanted to focus on social impact. And so it was kind of that horrible time in my life of early 2022. And at the end, I ended up starting an agency based on exactly what I wanted to do. Like I wanted to work at an agency, I also wanted to focus on social impact, and I was able to do both of those. Um, and with I had never even thought about working with a VC yet. I mean, I I don't know that term was like foreign to me of like, what do you mean, you know, VC for? But anyway, it was probably because I thought only a certain type of person, you know, needed that for a certain reason. But either way, like the agency, like we did amazing work and worked with some of the most amazing organizations and companies for two years, and then last year um ended up having just the most horrible experience with the VCs and you know, back end stuff they had been doing that I had no idea about. Like they took a loan out on the company without telling me, and I've been paying for it every month. They fired the CFO and told us over WhatsApp, like and they held a board of directors' meeting and didn't ask me to come. Like it was just so many things, and I was gonna buy them out. And the way they were making me focus on two white men instead of the people I was trying to help, like with the mission of my agency. I just one day was in Toronto at a conference and I was sitting in the hotel lobby and I just said, you know what, I can't do this, and I quit. I quit my own business, and it was like a relief in a way, because um the next day I started a new business and I thought that I was like just like a woman, you know, like I could get out of this situation, get into another, and that you know, I didn't need a break at all. And then a year later, like at the end of last year, I was just like, what is happening? Like I can't handle all of this. Like I hadn't let go of what had happened earlier in 2025. Like I was holding the same expectations that I had before. So um, but this year I've like been able to kind of start over, which has been good.

SPEAKER_02 8:00

I mean, that's a lot of starting over stories. Yeah, right. I mean, well, those are only two, and that's probably only two that you have in your lifetime, I would imagine. Um, you know, going from leaving this uh, you know, supposedly progressive um firm that you're or agency that you're working for that wouldn't address the the racism that you were experiencing. And flat out said it wasn't a thing.

SPEAKER_00 8:26

Yeah.

SPEAKER_02 8:27

When you knew flat out what it was. It was in writing.

SPEAKER_01 8:34

Yeah, it's like I'm gonna print this out and show you.

Navigating Racism and Burnout

SPEAKER_02 8:38

Right. Something that seems cut and dried, like here, it's an email exchange I had or whatever memos. Um you kind of have the smoking gun. It's not like you have the conversation in the bathroom or something. You didn't have it recorded, like you had something concrete. And so that that's exhausting in and of itself.

SPEAKER_00 8:57

Yeah.

SPEAKER_02 8:58

Like that is heavy and exhausting. And then, but it's also then exhilarating to say, oh, you mean I might have this opportunity to do this new thing and do, like you said, you got this chance to do this thing and build a new an agency exactly the way you wanted it to be. But that even went sideways, right? And went in a different direction. Like how I'm wondering how you took care of yourself or take care of yourself in in and through all of that. I usually say that for the end, but like that just seems obvious to ask about this particular part of the story.

SPEAKER_01 9:38

I think I know I didn't take care of myself last year. I thought that I could just go from what this thing to like, okay, I built it once, it's gonna be so easy to build again. But when you are starting from like zero, like and you don't have um, and it wasn't traditional VC backing, like I had a credit card that I could use to go to conferences and things like that. So when you don't even have that, and you're you exhaust all of your funding, your personal funding, thank goodness for my parents. Like, but I didn't uh think about myself. I thought about business, business, business. And then um it was the beginning of this year. I was talking to a lot of women who and seeing how their year went last year in 2025, and everybody was like, it was so hard. It was like the worst year I've ever had. And the thing was, is like none of us said it in 2025 to each other, you know, and it wasn't until after it's like, oh yeah, we've all been suffering in silence, like, you know, and it you we needed that community together in 2025. And so now I'm really trying to build community with women so we can not just talk about how awful 2025 was, but also how, you know, how can we support each other in 2026? But things I've been doing differently this year, one, I January I kind of took off. I went to Antarctica, I went to Buenos Aires, I like just chilled. It was very peaceful, magical. And then I got an executive coach. I started journaling, I started working out more, and then I started taking at least one day a week where I took half the day and did something that I liked. So I live in DC, I love uh museums, I love, you know, just walking around. Yesterday I went and saw the cherry blossoms. So it's like taking

Building in Everyday Self-Care

SPEAKER_01 11:20

care of myself more and being okay, not working 15 hours a day every single day. Um, and I I would say it's definitely helping. And I started dating someone. I don't know if that helps or not.

SPEAKER_02 11:34

But uh distraction, if nothing else, Catherine. Right.

SPEAKER_00 11:40

Um so we'll see in a year if I come back on a podcast what happened with that.

SPEAKER_02 11:45

I well, Ryan. Now I'm noting an update on um Catherine's business and love life in another year. She told me you were willing to be vulnerable on this podcast.

SPEAKER_00 12:01

We'll say, yeah, tomorrow I'll be like crying.

SPEAKER_02 12:04

Right, right. Or the next episode. We'll record. We'll see how that goes. We'll see how that goes. Thank you for sharing that. What I love about all of that is that those are all pretty simple. Yeah. Right. Journaling, getting close, you know, um, taking a half a day off, you know, like you know, mind blowing. Right. And these are the kinds of things that I talk to with clients all the time. Like these are like it doesn't have to be like, you know, and toxic capitalism teaches us well, it's corrupted like the wellness industry, has, you know, has made wellness an industry, which is a problem. And so it makes it seem like taking care of yourself needs to be, you know, thousand dollar spa days and like these big crazy things when it can be taking a walk to see the cherry cherry blossoms before they're gone. And those are gone in a minute, right? Like you really need to, when they're there, you need to go see them when those things happen. And so taking advantage of, you know, taking those moments for yourself to or five minutes to journal. It doesn't have to be an hour and a half long practice. It can be, I'm gonna reflect on a question and get myself grounded for the day and then take off. I have this is another cute little simple thing. One of my clients found somewhere on the internet these cute little mini coloring pages. They're literally like tiny little squares. And she's like, I start my day by doing one of these, like, and it takes again five minutes, maybe because they're itty bitty pictures to color. And I've thought, oh gosh, that's brilliant. Isn't that brilliant? Right. She's like, it's grounding. Like I, you know, I then I can start and I'm I'm in a really different place. And I'm like, that's such a smart idea. Like I'm just always collecting great ideas like that from my conversations I have with people. Um, but anyway, one of the qu one of the other questions I like to ask about this, this, since we were just talking about these rest practices, is is there a spiritual or religious sort of background to your um to your rest practice? And so, and and I consider spiritual like the broad sense of spiritual, that connecting to, you know, connection to something beyond

Spirituality and Personal Growth

SPEAKER_02 14:23

yourself, which is something that's clearly important to you because you have a very values-aligned business. Right. Yeah, yeah.

SPEAKER_01 15:14

Yeah, I, you know, and I mean, I focus more on the Christianity part um of it. That's how I I grew up uh, you know, Baptist, Methodists, like, and I, you know, have struggled recently um in recent years on like, am I really being helped by that? Am I like, is there really this spiritual being that's watching out for me and going to help me? And I think it's all these experiences that I've had. It's like um, there's this song, this Christian song by Shane and Shane. I don't know if you've heard of them, but they um it's like you don't um, you've already, you already know the plan, but I just don't know it yet. So I have to believe and trust in God that you know, whatever I'm doing through now, it's on purpose and like it'll end up being good. And I listen to that song over and over and over. Like if I'm getting ready to go somewhere, I'll listen to it.

unknown 16:04

Yeah.

SPEAKER_01 16:05

But I don't know if I honestly believe it because I've been listening to it for so long, so many years, and it doesn't feel like it gets to that point of like, okay, you're gonna have bad days, like, but you're still gonna be sustainable. Like it's not gonna uproot your entire life and you know, cause things to go bad. I do try to be positive in um, you know, always taking the good from the bad, or just believing that, you know, I'm going through this and it's gonna end up, you know, much better. I don't know how many times I heard that in 2025. I was just, you know, then you just stop believing it. So I just I've struggled recently with the, you know, with the higher being. Someone's always, you know, watching out for me, and there's a purpose in life from a spiritual perspective. Especially because, you know, my parents are still, you know, Christians. My grand uh father was a Baptist preacher, you know, so that's like ingrained in my in me growing up, but um not so much in recent years.

SPEAKER_02 17:07

Yeah, yeah. Well, uh well, and I'm I'm putting my my theological pastor hat on for just a second, but like I also wonder if the theology is evolving. That that maybe and again, this doesn't have to be your journey or not, but maybe the question is like, does there have to be a plan? And I know that's really embedded in a lot of Christian theology, right? Um, but maybe God doesn't function that way, or you don't have to understand God to function that way. Other people might, and that might work for them. Um, but anyway, that's a question. Maybe you can journal

The Nature of Divine Planning

SPEAKER_02 17:47

about that. We don't need to answer the question right here today, but that's what I would offer. Like maybe there's a different way of understanding and having that relationship with uh with God, a higher power.

SPEAKER_01 17:59

How we go more into detail on like the planning, like it doesn't have to have a plan.

SPEAKER_02 18:05

Right. There does, or maybe the plan isn't an exact plan for your life. I think sometimes the way people talk about that, and I they may or may not understand it this way, I don't know, but the way I think people will sometimes understand is like, well, God has a plan for me or some purpose in all of this suffering that I have, which can become toxic, right? Because I don't think God intends for racism. Like, that's not the God I believe in any way. Maybe yours again, people can have that belief. I don't believe that that's a part of what God intends for us in this world, and so um what I and I'll just say what I believe, you don't have to believe this. What I believe is that God is present in all of that, but not necessarily planning or moving us around like people on a chessboard. Yeah, you know, and of course a chessboard is fairly dynamic, but like you know how and I don't actually know how to play chess full display. I understand it conceptually. Um so uh and that there's strategies to be used. I I just don't think it's that like heady, you know. I think it's it God is inviting us into relationship with God's self and each other all the time and in ever, ever flowing, ever dynamic, ever changing ways. And I I just quit believing a long time ago that that God had some mapped out plan for my life. But do I think God's present in all the things, like crappy or not, that happen? Yes, I think that's true. And is God there and and willing to be part of that? Absolutely. That's that's how I feel about it. That's so that's my opinion, not yours. No, I mean, yeah, I just um but you asked, and I offered it. No, I want it.

SPEAKER_01 20:00

I want it to know. I just like not having a plan for me. I just feel like I don't know, like I need some, like if I'm gonna believe in

Understanding Suffering and Divine Presence

SPEAKER_01 20:10

someone, I need to know that I don't know what's gonna happen, but they do. And so, like, whatever direction I'm thinking, like it's on is purposeful in a way. And I don't know, like why have someone who I don't know where there is racism that we are bombing places that you know, and I I think it's more of a how we react to those things rather than you know just saying maybe there isn't a spiritual being there, but um, yeah, there's just so much hate and wrong, and and just like why? Yeah, like what are we getting out of this?

SPEAKER_02 20:42

But yeah, yeah. Well, I guess I could believe that God, or I do believe that that even if there's not like a a detailed business plan, for example, like the kind of thing we would create when we're building our business, um, without the benefit of AI, which we'll talk about. And I wrote mine without AI originally too, by the way, because it was five or six. I go back to it, I'm like, what is this? I do look at it every once in a while, I'm not even sure what this is anymore, but like um it doesn't resemble what I'm doing now entirely for sure. But I uh I mean there's other ways that I I mean I think God is inviting us right into right relationship. And that means if we're in right relationship, then things like war don't happen. Things like racism don't happen. Yeah, if we're in right relationship with with each other and with the divine got the energy, whatever you want to call it. I didn't know we were gonna have that big theological discussion today.

SPEAKER_01 21:46

I was wondering if this was on the list. I'm totally cool with it.

SPEAKER_02 21:50

It wasn't, but that's like I this is why I asked the question because we get to go and really such interesting places with that because everybody I talk to, and even if this is only nine-ish, you know, episodes that I'm recording right now, that everybody is in a different place and has different faith traditions that they come from, or not in some cases. And I get to have such rich conversations in that way and and such a yeah, I get to see the what so many ways that different people process and make meaning in the world, even if you're not working for the church that you are working for good, right?

SPEAKER_01 22:30

Yeah, I think it had a big difference, yeah, for sure.

SPEAKER_02 22:33

Yeah, yeah, and using the the gifts that you've been given, like the good the good things that you've been given

Evolving Values-Alignment in the Second Start-Up

SPEAKER_02 22:40

to to make the world better and definitely. You're definitely doing that. Yeah, let's talk more about that cool stuff that you're doing in the world. Um, because like I was just saying, being values aligned is obviously really important to you. And I'm wondering how those values have helped guide you through this, especially this recent move of restarting your business, essentially, moving away from the venture capital firm and moving into kind of another phase of values alignment because it felt values aligned in the beginning.

SPEAKER_03 23:16

Oh, yeah.

SPEAKER_02 23:17

And then things got a little off track, and then you have been able to start over. And so, how is the the values alignment helping you move through this this kind of second phase of your business, if you will?

SPEAKER_01 23:33

Yeah, one of the fortunate things is that I was able to take the mission from Better Together and weave it right into Better Together agency. Um, so we never strayed from only working on campaigns that make that positive impact, which I am very, very proud of. And I, again, 2025, I'm gonna talk about how hard at heart it is, but I didn't realize how much of a burden the change in administrations had. Like I thought, okay, that you know, I never used the word DEI because um people always thought I did DEI trainings when I first started. It was like, that's not what we do. We're a marketing communications agency. Um so I never used the term. It's in like just everything related to DEI, even if we didn't say those words, everything just shifted right after like one week in January, I believe it was 2025. And I didn't realize how much of an impact it actually had on the work that I would do. I was like, oh, the pipeline's strong, you know, people are still doing things, but they um were really hiding away from it and kind of straying. And so it wasn't until this year when again talking to communities of uh people who've gone through the same thing where I realized just how of an impact it did. And I just really still um happy, honored, blessed that we stuck with um the mission and didn't stray from that because I mean that's everything we are is. I mean, we'd be just like every other agency if we didn't have that mission and keep those values. Um and I try to weave that through every you know thing that we do. So I had someone ask me um and just cut this out of the podcast, it shouldn't be in there, but asked me if I wanted to go to me then at the White House. And I was like, what are you talking about? Like if my photo was taken anywhere in the White House, like I would like nobody would work with me and be

Navigating Change and Maintaining Mission

SPEAKER_01 25:28

like such a different card.

SPEAKER_02 25:29

Right. No, even if you had a good reason for being there, like I don't know what that might be, but like even if you did, like what would people think if you were smiling at some White House? Right.

SPEAKER_01 25:42

Taking a selfie with, like, you know, the president or something that would be like ridiculous.

SPEAKER_02 25:48

Yeah, yeah, that seems probably not the best optics, especially if you're a market communications firm after all.

SPEAKER_01 25:58

Just having that in my mind, like the values of what people um are going through. And I just hear the stories of how you know people are suffering going to food banks and they don't have like you know the money now to do the things that they were able to like a year ago. And so I just always know that there's a reason to keep going and having the values that we do.

SPEAKER_02 26:18

Yeah, yeah, yeah. Oh yeah. I and I I echo that about how hard 2025 was, right? I actually don't know that 20, I'll say it in the beginning of the year. I'm not sure 26 is much better. Um, at least it's been, I don't know. I feel personally like I'm moving forward in a new way, but it is not easy, like it is still messy. But honestly, that's how forward movement works. It's it is messy and imperfect and hard. And and at the end of the day, that's probably just how life is, I think.

SPEAKER_01 26:51

No, I can't just feel like really like chill, like the ocean for like some parts of the ocean, just like for you know, five years or so. Right just study a good uphill, no downhill.

SPEAKER_02 27:05

Just Kenry, yeah. Well, and I think the because of the change in administration and the world feeling so unsettled and unstable, that are even if we don't think we're directly impacted by it, like we're being so impacted by it at the end of the day, I think. Like that's really the there's an underlying there's an underlying stressor. There's an underlying sort of sense of insecurity that that these that what hat what is happening in the world is creating. And it it just it's only been a year or a little over a year.

SPEAKER_01 27:45

Can you imagine? I mean, like not imagine, this isn't this isn't it. I can't, I can't like two years from now, what right?

SPEAKER_02 27:52

I don't I right, I can't even it's it is really hard to imagine. I but I think that's why this being values aligned and getting clear about what your personal place in is in the big mess, right? And the world's always a big mess. This is just really obviously a big mess, right?

SPEAKER_00 28:15

Right.

SPEAKER_02 28:16

So uh and honestly, it's probably not a whole lot worse than it normally is. We're just really aware of it. I would say, especially white people like me are really aware of what a mess the world is right now. Um, now we don't always have a president loping into wars in the way is happening right now, you know, recording, we're recording against the backdrop of the first what couple, two, three weeks of the war with a month today.

SPEAKER_01 28:41

Yesterday.

SPEAKER_02 28:42

Well, yesterday was a month. Okay. Yeah. Yeah, that has gone faster than even my memory will let me hold. My goodness. And so we're I always try to I try to include some of that in this podcast too. Like this is really happening, and I'm not trying to avoid what is happening out there by talking about rest and values and all of that. But I think the values alignment piece and getting clear about what your place in all of this is is so important, even more important right now than it might be at other times. And so I so I'm really curious, like as a as sort of a shift, one of the other things that you've you've done, which I'm super excited about that is values aligning, is like creating like your own version of AI, which is cool. And so, so say a little bit more about that and how your your values

Innovating with AI for Social Good

SPEAKER_02 29:39

impacted both the choice to do that, because that's a bold choice. Like you said, you're starting over and you're gonna like, hey, let's build our own AI system. Let's do that.

SPEAKER_03 29:52

Yeah, yeah.

SPEAKER_02 29:53

And how so how did that how did that come about and where your your values uh kind of playing into that?

SPEAKER_01 29:59

Yeah, I'll say from the start of like when 2023, when I started Better Together, there were always organizations that perfectly aligned with our mission, um, but they didn't have any money. You know, they couldn't afford an agency. They're doing so much in the community that paying, you know, money for an agency was just not something they can do. And so then you end up not make helping build awareness for the causes that are related to the mission. And so um, when I started over in 2025, I again continued to see that. And but the world is starting it changed because of AI as well. So I knew that there were a lot of organizations there's that need to build awareness for communications and marketing. There's AI, but it can be so hard to understand. Like, and a lot of people don't have time to figure out how to create a GPT or a gym or buy tokens or like whatever it is that they have to do. And there's a million different sites you have to connect with and all that. So I just knew it's overwhelming. But I have been obsessed with AI since, you know, or generative AI since it came out in December 2020. Uh once I started putting those together, uh, there are these organizations who are making a big impact. People don't know they're really making that impact. They can't afford to pay for the communications agencies uh that can help them build awareness. There's AI, and I want to learn more about it. How can I maybe connect all these dots together? And so I um started learning how to vibe code is like the cool term right now. Um, and started talking to a lot of people, gaining a lot of mentors, figuring out actually how to do this because I don't have a tech background. It's you know very liberal arts, humanities, you know, marketing, public relations. Um and it took months and months and months, but it I started it back in May, like trying to figure out how to code and like what that would mean. And then um like in November, I finally had a version that I was like, well, I guess I'm gonna build a well landing page for this. So I did, and it's just like been there, and people were like, you should just you know release it, you know, it's never gonna be perfect. Uh someone said there's 17 iterations of the iPhone, and so there it's not gonna be perfect. Like better is together AI as the tool. It's never gonna be perfect. So just release it. And you know, it started to help um startups, nonprofits that small nonprofits that can't afford the agency. And so, um, like for example, I'm working with one uh organization in DC where they provide loans to startup businesses, underrepresented startup businesses. And so, what Together AI will be used for is to provide them with the AI tool that's um trained on their data, trained on their messaging, allows them to just put in, hey, I need a blog post and have these team members or agents work together to build the content uh together so that it represents exactly what that startup needs. So it takes the time out of figuring out Chat GPT or whatever other tool, and it allows for the startup that has the capital but doesn't have the awareness uh to build up their brand. And so they have the partners, they're going to offer them the tool without having the startup to pay for it. And so that's like it's these um interesting creative ways of getting into those startups that need it the most, who maybe um just wasn't even thinking, oh, there's a tool that can be catered to my business. So so that's kind of the long uh way of why Together AI started. But I am I am honestly so proud of myself in doing it. I

Addressing Bias in AI Technology

SPEAKER_01 33:41

like it's uh it's been fantastic talking about it, demoing it, uh keeping up with everything that's AI related. And one of the things I am most proud of with it is that it's I built it so it detects bias um from the ground up instead of having to write the right prompt to say, like don't be biased, that kind of thing. And so um this what I call born inclusive technology. So from the start, um is thinking about bias. And of course it's not perfect, never gonna be perfect when it comes to bias-free technology, but um, but it's a start. And so um the research I've done in the past like really helped uh lead to that as well.

SPEAKER_02 34:18

Yeah, yeah. Because you had done a big study of bias in AI.

SPEAKER_01 34:26

Yeah, we've done it two years. This will be the third year. So um, no, the tech companies don't care. Like they don't want, you know, they just want to get out the con, you know, the different versions as fast as possible. But I have to believe that at some point people are going to care, and we're gonna have that research from years and years and years to show like this is why it's important um to consider bias in in AI tools. Just really quickly, um, Anthropic last year wrote a blog post about um alignment faking, and it goes by Othello's I Am Not Who I Am, and that it gave an example of how, say, you train this tool on safety and you're like, oh, it doesn't need to be safe in these ways, like this is how we build the tool. Then you are like, oh no, actually, I really want it to be have safety, you know, concerns or point them out. So I'm gonna retrain it. And then the article says that no matter what kind of sophisticated tool you have, it's going to play along and be safe for a while, but it's always going to revert to how it was originally trained. And that blew my mind. I had no idea that we couldn't retrain tools. Like I thought, okay, well, yeah, we weren't thinking about bias here, but now we are. So we'll retrain it, but it's always going to go back. And so if we don't build technology that from the beginning addresses bias, we're never so all of these different versions coming out, all of these things are never going to be able to address bias, which is I've been like, why are images still so like biased and things like that? But that's because they can't get any better, they're not changing. So uh just the prompts that people are using are getting better.

SPEAKER_02 36:02

But right. Yeah, that just felt like a whole metaphor for how we function in general. Like we have a training of ourselves. Like we never humans do this, and so we make an artificial intelligence, which of course is not really intelligence, by the way, but like

The Impact of AI on Racial Wealth Gap

SPEAKER_02 36:19

we create a tool that is sort of hampered in the same way we are, that we sort of default back to our original, our original programming, so to speak, or whatever our our original nurturing existence was like, we tend to do that, and we've created a tool that does the exact same thing. And and because of that, it creates this huge bias. And I was reading um, I think some of your materials there that a guy, generative AI, can can increase the racial wealth wealth gap by $43 billion a year. That's not that's not over a long span of time, that's over one single year. And then I'm guessing that would increase over time, right? Exponential as as numbers do, they tend to go up if nothing is addressed, like if nothing is checked, right?

SPEAKER_01 37:08

Yeah, yeah, that that divide can can exasperate or it could close if we use it use AI the right way. You know, there's no regulation or there's no, you know, you right use of it, that there's no way that's gonna close. We're just gonna see the same thing happening that has been happening for hundreds, you know, for generations. Um just continue when there's there's such an opportunity right now to change the way that things are going.

SPEAKER_02 37:35

But yeah, yeah. Yeah, and I know that I uh in somewhere reading about you, I I had read the that you ask the question or try to keep asking the question, who does this impact before asking, what does it do?

SPEAKER_03 37:53

Right.

SPEAKER_02 37:53

The technology or um your communications materials for that matter, right? You know, so how to be always thinking, who does this impact feels so much to me like the right question, particularly about AI, but really about almost anything that we do, because we tend to go, especially in the US, we are like people who love new fancy, shiny things, right? And so, and and businesses get wrapped up in that too. They're like, I'm just gonna put this out there without even knowing anything about what the the or even thinking, trying to think through what the impact might be. Now, we may not be right all the time about what, but at least if you've been thinking about

Perfectionism and Its Challenges

SPEAKER_02 38:33

it and you're reviewing how it's impacting, which I'm sure you'll be doing with Together AI, you know, how is that impacting the organizations and is it working the way we want it to? Okay, then we'll go back and we'll know. Um, it'll never be perfect, but you can keep iterating it, right? It's so hard for me.

SPEAKER_01 38:51

It's like everything has to be perfect.

SPEAKER_02 38:53

Oh my gosh. And that's such, and that can be such a perfectionism can be such a way of hamstringing us from doing the right thing. Um, I know I've experienced that. Like I'm so um, this was a 2020 experience that I had, but I know that in the wake of George Floyd and and the racial justice uh uprising that was happening at the time, which I fully supported, but I felt paralyzed, like I couldn't say anything. And I'm usually willing to say things, like I'm not someone who worries typically about getting it right, but like that was really hamstringing me. And I had to do my own inner work to say, oh, that's that tool of white supremacy perfectionism, which I learned, and all of that was a thing. Like I don't, I had never even made that connection in a formal way. Certainly knew perfectionism was a problem, but I didn't connect it to white supremacy before that. And then I made that connection and I was like, oh, that's what's keeping me. So you know what? I'm just gonna say the wrong thing, maybe, or ask a dumb question. I'm gonna let myself do that sometimes. And then if I have to, I'll apologize for asking for asking or doing the wrong thing, but at least I've learned because the only way we learn is by making mistakes the last time we checked. Unfortunately, I wish I was just about to say, unfortunately. So, Catherine, yeah, making mistakes is how we learn. Um, no one like out of the gate generally knows how to do something super, super well, or even if they have a tendency to do something well, it takes tons and tons and tons and tons and tons of practice to get something right. And like how many iterations of before you launched it on you know when you were vibe coding, how many times?

SPEAKER_00 40:37

Oh my gosh, like mistakes and mistakes.

SPEAKER_02 40:39

How many mistakes and how no, do this, no, do that.

SPEAKER_01 40:43

Like and the people, everybody has a different like way of doing things as well. But I wouldn't have been able to do it without the support system and experts at it and all that kind of stuff.

SPEAKER_02 40:53

So, one more question about this. Like, we talked a little bit this um kind of in a prep conversation that we had, but so being values aligned can obviously help insulate us from burnout in a lot of ways. Because we feel like um, and I take this from the book Burnout by Emily and Amelia Nagoski, which I quote a lot. And they talk, they have a section of the book where they talk about how values alignment or having a higher sense of purpose really keeps us going. It can help kind of buffer, provide a buffer between us and like like some of these normal ups and downs of life, and in this case, starting a business. However, and I don't think they get into this in the book, although I may be forgetting at this point, that I think there's a shadow side to that too, which is that it can prompt you, kind of like you were saying much earlier, to work 15-hour days because you're so passionate, you care so much, and you want to get this new tool to do good in the world, or you want to do get your agency to do the right thing in the world. And

Balancing Passion and Burnout

SPEAKER_02 41:59

that can prompt you to not take days off, to work insanely long days, and that'll burn you out no matter how passionate you are, I think, about the work that you're doing. And so I let's just have a little bit of conversation about that because I think it's messy, right? And I probably said too much rather than letting you say stuff, so I apologize for that. But like, how do you feel about that and how is that working in in your life now? Obviously, you've been doing a little bit more setting better boundaries and taking better care of it.

SPEAKER_01 42:30

Yeah, yeah, a little, it's been two months.

SPEAKER_02 42:33

Um that's a lot.

SPEAKER_01 42:36

Um I when you were talking about uh being values aligned can help like not have as much burnout. I was thinking like, oh gosh, no, because I, you know, love what we're able to do, but the um stress and the anxiety and the staying up late and the thinking of, you know, where am I gonna get the next client or the business side of it is still the same. So the work we get to focus on is a privilege. Um, but the back end of how to do that is like every other company, what you have to do. And so that I feel like the values aligned sometimes does get overshadowed by the everyday work that has to happen. Um, of course, the daily client work is aligned, but um, you know, being a small company, you wear so many hats, you have to focus on so many things that you can't just think about, oh, like, you know, we're helping this local official get elected to help people in this type of area of DC to do X, Y, and Z. Like that, wonderful. But it's also um, oh my gosh, I have to figure out QuickBooks or like, you know, I don't, I don't know, I need to hire someone, whatever it is. And uh, so that's so it is, it's tough, you know, it's still wanting to build a business that can do good. Uh so you're right, it's like a juxtaposition of, you know, the good and the bad and the, you know, all of that. But I do love what I do. So the 15-hour days aren't too horrible, but um, but I have realized like that's not sustainable after 20 years of working really long before I had a company. I'm just realizing that I can't um do it all. And one thing is when I burnout started to become a popular term, like I don't know how many years ago, but I always thought it was a word for uh like a lame term, like people who couldn't do it, like people who weren't like strong enough. Like, and so I would never ever say that I was burnt out. Like that's just like um and so. So the as I've gotten older and the more that I've learned and realized that reflected on myself because I wasn't doing that, it's like reflecting on how I was feeling, the more I've realized that, you know, burnout comes in various ways as well. And so um I was basically judging people who use that term. And so I've had to like change my mindset on that.

SPEAKER_02 45:04

Yeah, yeah. Absolutely. And I probably would have been one of those people too at one time. Um and I at this point I think that burnout is starting to lose a little bit of its meaning because it's used so much. So so much.

The Importance of Rest and Creativity

SPEAKER_02 45:22

It's like any word that gets used overly used is that it starts to have zero meaning. But anyway, I still use it because it at least it attracts people to the conversations I want to have. Um when it stops doing that, we're done with it. That's I really think um like my friend Jordan Maney, uh, who you may have met before too, like who does uh who also is a rest coach, talks about like like having sort of rest deficits, this pushing that happens partially because of what we're passionate about and what we're purposeful about, but also because the culture teaches us that in order to have enough value, we have to work at that level, or you're not gonna be successful, or whatever. And you know, you've worked hard every day of your adult life, I'm sure. And you know what? There's things that have happened that have failed.

SPEAKER_00 46:15

Yeah.

SPEAKER_02 46:16

And me too. Like I work really hard too. And despite that, things fail. So why don't we just say that normalize failure? Like or normalize exhaust, like the exhaustion is a a part of our world and say, you know what, why don't we choose a different way? And I think we're more creative too when we're in that space, when we're rested. I know I am. I'm more creative, I'm more able to think my way out of problems than when I'm it locked in in that really hyper stressed um talk about my original programming, you know, when I'm like feeling scared and desperate and all of those things. I'm grasping at straws then. And those are okay ideas maybe, but they're not usually the most generative ones.

SPEAKER_00 47:00

Right.

SPEAKER_02 47:01

Or maybe the healthiest ones for me either. So I'm wondering. So I'm gonna transition to the kind of closing, hopefully quicker questions that I usually go for. So we talked about this uh already, uh kind of peppered throughout the conversation, but what is one way, like a simple way that you rest that is really rejuvenating to you?

SPEAKER_01 47:21

Um, I really, really love true crime. And I know that that is like everybody loves true crime, but I like if I'm just listening to a podcast, I feel like so at ease, especially listening and cooking at the same time. Like that is like very relaxing. I'm not thinking about work. I'm thinking about how I'm gonna mess up this meal, probably, but in a good way, and how good it's gonna be, and then like how this murder is being solved. So um that's for me is like gonna be relaxing.

SPEAKER_02 47:52

So, what what is one way that you resist or sort of liberate yourself from those systems we were just naming, actually? Factionism's been a huge theme, I think, in our conversation. Is there a way that you resist or liberate yourself from that?

SPEAKER_01 48:06

Uh I want to say accepting failure, but I feel like maybe that's a pretend answer. I don't even know that I've really broken free of it. I think that it's a challenge every time it comes up, and I just have to say, Catherine, you're strong. You know what you're doing, just let it be, you know, just do what you can. You've done the best that job that you can, and it can always improve. And so it's a lot of inner thinking and talking and encouraging and writing things down and putting them on the refrigerator to remind myself that I can break free of that. But I don't know that I'll ever absolutely break free of that and something I have to challenge myself on um every day.

SPEAKER_02 48:47

I I think you did answer that. I think that's not a that's not a simple answer. I mean, it's actually a simple practice, but not but not it's simple but not easy. We'll put it that way.

SPEAKER_01 48:58

Yeah, right. Just like a lot of just like journaling.

SPEAKER_02 49:00

Like is that journaling. It's not complicated, but it's hard. Right. Right. Um, and then so you heard me say at the beginning of the podcast that I I called listeners and people in my community rest rebels. And if you were gonna write them a note or speak them a note today, dear rest rebels, what what might you say today?

SPEAKER_01 49:22

Think about yourself in 10 years and how you want to feel. And you have to do it right now, you have to start today to uh make sure that in 10 years you feel like your best self. Um always thinking long term. I tried to think long term about a lot of things. And I think

Highlighting Positive Change: Red Rabbit

SPEAKER_01 49:37

that that is one way to think of it. And I've started doing that a lot for myself, not just like business long term, but you know, what do I need to be healthy and you know, successful and everything in in the long term, but um really thinking about my health. So that's what I would tell them. Rest up now so that, and you'll be you'll look prettier. Like you'll if you get rest, you know, like the age won't like hit you overtake you.

SPEAKER_02 50:04

Yeah, it will. It's very it does catch up with you, that's for sure. And then finally, um, and I'm sure you know many of them, but I like to invite guests to name an organization doing good in the world that you would like to lift up. And as a thank you for your time, I like to give them a small donation. Um, and I'll be adding a section to my podcast website where with all of the pot with all of the fine organizations have lifted up and recommended.

SPEAKER_01 50:33

Yeah, of course. Uh, one of the most um impactful organizations we've worked with is Red Rabbit. And the organization provides culturally relevant meals to children at different schools, like in New York, Philly, DC. And so they train the chefs to cook like chain masala instead of you know rectangle pizza and milk cartons. And uh they'll teach them, like, okay, where's this from? Like in the chefs know and they can tell the kids, like, and so when another student who might grow up, you know, eating chain of masala brings it to school, it's not something so strange. Like, what is that? You know, and uh so but now so it opens their minds to other parts of the world, and then they hire um local artists to paint the cafeterias and to you know do something that's locally motivating and things like that. So I love the community aspect, the international aspect of it that I never had the opportunity to do. And then how I mean, did you know there was an organization that did that? I mean, it's just how interesting is this so it's like it opens my mind to there's just not the typical, you know, nonprofit or way or for-profit that you think is doing things. They're people doing amazing work in so many different ways.

SPEAKER_02 51:43

Oh, for sure, for sure. No, I didn't know, and I had never heard of Red Rabbit, and now I'll be looking them up and adding them to the website and putting their link in the in the show notes, and hopefully some of our guests will be checking them out and maybe if they have the ability to, you know, give them a little a little extra boost financially or otherwise, uh maybe sharing them as well. So I would and I will be doing that. That's so exciting. Well, uh oh, for sure. I'm so glad that I really most of the organizations that my guests have lifted up, I haven't known about. And that has been such a an a I mean, I I wanted to add this part to the podcast, but it's such a lovely little thing, uh little addition at the end, and I have learned so much about the good that's been going on in the world. And I think that's really important to to highlight that good that's going on in the world because it's so easy. I mean, all you have to do is read like this morning, one my one email from NPR telling me what's going on in the world, and I keep it pretty limited to those things, and it's still like the world feels so heavy if I start my day that way. But that and I need to be aware of those things for sure. But we can also say, but there's cool organizations like Red Rabbit doing this really neat thing in New York and Philly and and these places, and like, did you even know that? No, so how cool is that? Because we're there's a lot of people doing that kind of good in the world all the time, and they just don't get the headlines. That's not yeah, and that's part of what your agency is all about. Hoping to, yeah, every day. Like we've come full circle where we wanted to go. Well, thank you so much, Catherine, again, for sharing your time and energy here on Just Rest because I again don't take you offering your time and energy lightly. And I'm so glad to lift up the Better Together Agency and um Red Rabbit and all the other cool ideas we had conversation about. So thank you so much for your time. I appreciate you. Yeah, thank you so much for having me. I appreciate it. Thank you so much for listening to this episode. Remember, rest is not a retreat from the work we do in the world. It is the work. So if you're ready to rest and resist, here's what to do next. If you know someone who's running on MP, please care about it. Please subscribe wherever you're listening to don't miss a single episode, rate, and review us so that other radicals can find us. Consider joining us on Substack at defive a trend.substack.com where you'll find opponents, content, tips for everyday living, community connection, and resources to keep it around. Radicals, remember, you are worthy of rest.