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Transcripts: Women talk truth about their crucial role in the American economy and the inequitable expectation to ‘carry it all’

Uncommon Conversations: Desiree Vargas Wrigley and Naomi Hirabayashi

Desiree Vargas Wrigley: I was actually working at the Kauffman Foundation when I got my first idea for a business, and that was one of the first crowdfunding platforms in the world called Give Forward. So I moved to Chicago and built that to $200 million in transactions and about 30 million uniques a year, so it got to be a pretty big site and then had a real kind of… woman founder moment and doubted myself and thought maybe a seasoned operator would be able to do a better job and grow it faster. So I stepped into a strategy role that was not a good call at all and then I ended up building my second company Pearachute – also in Chicago and it is a kid’s activity marketplace, so we help busy moms find enrichment activities for their children, and at the same time, help support small businesses who are looking for an efficient and easy way to find their ideal families and customers.

Naomi Hirabayashi: Congrats on everything you’ve built. And the doubting yourself moment and it turns out like you were the best person for the job, no doubt is very real. So I would love to hear more about that.

I’m Naomi, I am the co-founder at Shine. Shine is on a mission to make taking care of your mental and emotional health, easier and more representative and more inclusive. And myself and my business partner, Marah, who’s actually out on maternity leave right now with her beautiful new daughter, our path to entrepreneurship came from really just our own kind of frustration and feeling very much overlooked in the well-being industry, both as women of color and feeling like, in a lot of ways, it’s gotten better but when we started Shine in 2016, feeling like there was an absence in the wellness world or the mental health world to talk about and get support for taking care of your mental and emotional health in a way that was much more preventative, daily, and  conversational.

So, fast forward to where we are now five years later, we actually just celebrated our five-year milestone at Shine. We’re in 189 countries, we were just named best of 2020 by Apple, for the work that we did for more inclusive mental health, particularly in the backdrop of this last year. And so I’m so excited to have this conversation. This is one of those conversations I was really excited about. I think both being female founders, is an underrepresented experience in this space and that’s changing, but there’s still so much change that needs to happen. And then I have a two-and-a-half year-old daughter and just navigating being a co-founder and a mother and all of that – your company is your child as well. So it’s just a very unique experience. And I’m always eager to hear from other women in the journey.

Wrigley: Well, I’m also a mother, and my kids are nine and about to turn seven and then also a step mom to a 15-year-old. So I’m a few years ahead of you, but I’m curious just as a woman and entrepreneur how you navigated this last year with a two-and-a-half-year-old or even  a one-and-a-half-year-old that is.

Hirabayashi: Yes. Well, it’s so interesting because I even look at pictures, I’m sure everybody’s doing this to some degree.Last March feels like a lifetime ago, a world ago, all of the things, and she was still a baby in so many ways then and I think probably for a lot of mothers, it’s gone through different stages. The first three months of the pandemic were incredibly hard – with the qualifier of hard in comparison and keeping perspective on all of it. But we didn’t have any daycare and have any childcare coverage. And that on top of building a business and a lot going on in the world and in our country that deeply impacted our community was just… it was just a hard time to navigate. And I think I tried to talk very kindly to myself about what I was able to get done because it was like jumping between meetings and trying to give her bath and then feed her and then being like, “Well, she’s watching eight hours of television today. That’s just what today looks like, because those are the only options that we have.”

And then also experience. I had an ectopic pregnancy last year. And so there was a lot happening. And I think that’s… there’s a version… everybody has some version of that. There’s been so much grief and loss in this last year and it takes a lot of different ways and shapes and forms. So how that impacts me today is I think just the resilience of all of us, and I think particularly as women who have had to hold so many things together at once to give myself space that some days look a little different in terms of productivity, feeling appreciation for the progress that we have made, seeing her in school and social and getting curriculums and all of that. And then my health. My health as a woman, not taking that for granted. So yeah, what about you? I mean, that’s having a teenager and all kids in school age, that’s a lot to manage.

Wrigley: Yeah, I’m not going to lie,- it was really, really tough. Specifically for me in the business that Pearachute is in. We are a last-minute kids activity marketplace. So, you know  think like dropping into a ballet class to see if it’s something that you want to be doing long-term. And so I suddenly found myself without any inventory to be selling and even… yes, the transition to online was a possibility, but there were so many competitors that were so far ahead of us in the space and we didn’t know how long it was going to last. It didn’t feel like the right move at the right time for us just given the business model. And so we did eventually evolve… not eventually we did pretty quickly but to allow for online class bookings through the platform. But it was.. personally it’s such a hard place to be in because Pearachute hit this really amazing momentum at the very beginning of 2020. We changed our business model from being a class pass for kids to being more like Expedia.

And so we went from about 1500 locations on the platform to 6,000 in five weeks. And so it felt like we’re… as a four year old company, at that point, we were finally starting to hit our stride and it had been a slog… I’m sure you’ve experienced this fundraising, but when you’re building a business that’s unfamiliar,when the problem is unfamiliar to a predominantly white, rich male investor pool, it just takes a lot longer to get the traction metrics that you need to get to the next level. And so most men unfortunately had never spent three hours looking for floor hockey for a seven-year-old. So they didn’t really understand what we were solving. And I did raise money, I raised $4 million. So it’s not like I didn’t raise anything but compared to.

Hirabayashi: That’s amazing …

Wrigley: Thank you. But compared to the $20 million…

Hirabayashi: The money in the market, yeah.

Wrigley: Other marketplaces that are solving less important problems I think… it just… it felt like it was not enough. So, on the one side I felt like, “Okay, we have this business model that’s going to work, and me as a founder, I felt really validated by the changes that we’ve made. And then of course it’s outside of our control circumstances happened, but it didn’t just affect me and my 12-person team. It was the now 6,000 locations that are predominantly run by women and people of color for enriching our children. All of them… we all get hit with the same problem at the same  time. And that time period between when everything shut down and when PPP opened up was tremendously stressful for us as a startup and our partners. And we saw the level of work that fell on mother’s shoulders, because most of those business owners are also mothers. It was just unmanageable.

It was an unmanageable amount of work. And at the same time, my youngest was in kindergarten and so not yet reading. And so e-learning became this incredible burden. And my husband’s a police officer, so he can’t be home to help. And so I really struggled and I know I wasn’t alone. There were a lot of women who are going through something similar in terms of, “how do I balance what is now a diminishing career or business opportunity at the same time I have all of these personal demands and this general fear of, ‘What happens if I get sick? What happens when I’m not here to take care of my kids?'”

And so, so many of my friends moved to part-time or removed themselves from the workforce and these are high earning women that were, suddenly taking themselves off the path. And it just feels like we have lost a decade and a half of progress as women, professionally and also the stay-at-home moms who were thinking about going back, but now feel like that’s completely off the table, or that their skillsets are that much farther behind now, because of all the acceleration that we had technically and digitally over the last year. So we have a lot of work to do as a society I think to fix things for women.

Hirabayashi: And knowing that we were already behind, there’s already inequity – so much inequity.

Wrigley: I know, a friend of mine wrote this book and I mean she’s borrowing the data but I didn’t realize that the gender pay gap is $564 billion a year, and I knew it was big, but when you talk about it in terms of 18 cents on the dollar or whatever, you’re like, “Oh, it’s 18 cents.” But when you amplify that to  the population or magnify it, that’s the equivalent of one quarter of the first stimulus bill. So every four years women are getting the full impact of the stimulus bill negated against our earning potential. It’s insane. So what can we do about it?

Hirabayashi: I know, I know. And you know, I wanted to give a shout out to Reshma, who was the former founder… she just transitioned… she was the founder of Girls Who Code, she’s been doing a lot of work around this initiative called the Marshall Plan for Moms and it’s around creating essentially stimulus packages specifically for motherhood and recognizing exactly as you said so well, we’ve lost, we were already behind. And I didn’t realize the cumulative number of what that 18 cents represents, which is…

Wrigley: Staggering.

Hirabayashi: Just staggering. And then this happened, this last year happened. Right? And so much of that is obviously outside of our control, but I think it reflects what happens, which is… women are predominantly… we’re obviously, broad strokes, general terms, caretaking more. And the choice of… “What do you do? What do you do?” Having to make that choice between your kids’ education and your salary and your career. Yeah, I don’t know…  I don’t know what we do about it, but I definitely think talking about it and just raising the level of awareness around what the problem is… and I think as women, I’d be curious, like Desiree for you, it also just hits home in that there’s so many different situations that we’ve endured in fundraising or as female founders in a very underrepresented group, in a predominantly white male system, that you felt those inequities. It’s like that number as a representation  has been felt in meetings or times that you’ve been undervalued or overlooked. And we do. We just have a lot of work to do.

Wrigley: There’s so many examples I think of that in my career and I’m sure you have it too, but from when I was leaving Gift Forward, because I couldn’t watch this other person sink this baby that I built. The severance that I was offered was… I started the company first. I brought in a male co-founder. My severance was less than what they offered my male co-founder. And I mean, I just couldn’t believe that they would even have the gall to do it. And then similarly, when fundraising, yes we raised money from a lot of the same firms that some of the cool peers raised. But our check sizes were a third of what they got and the valuation reflected that. Even though our revenue and momentum was the same or better. It’s so hard as a woman to find that out after and feel like you were betrayed in this meeting that seemed like a collaborative partnership, but really, probably just checking the box in some ways, for them to have some diversity in their portfolio. And it’s something that I’m actually working on now.

I’m now running an initiative called TechRise, which is a $5 million friends and family around funding for Black and Latinx founders in Chicago. And it’s non-dilutive grants. And we do 30 pitch competitions a year, and that’s how we distribute the funds. So it’s pretty democratized. We invite VCs and angels from across the country to come and we really are trying to change that narrative at least  locally, and we’re very, very focused too on the intersectionality of women, trans, non-binary with the Black and Latinx communities because Black women only get 0.27% of venture funding and Latino women get 0.37[%] and women as a whole get 2.4[%]. But it’s an embarrassing sum as a country that is supposed to be more progressive.

Hirabayashi: That is amazing that you’re doing that. For Marah and myself, Marah was the first in her family to go to college. I went to community colleges, ended up graduating from a four-year university, but we didn’t really necessarily have the track that was the typical track, and something that we were so thankful for is the democratized open-access forms for getting into what is a very exclusive industry. And shout out to Harlem Capital, who is actually one of our investors and our most recent round. If you go to their website, especially if you’re an investor, they have such a great example of how to do exactly what you’re doing, because they want to diversify the face of entrepreneurship. Here’s what we look for, send  us your deck, and that’s how you do it.

You don’t need a warm intro, you don’t have to have gone to certain schools necessarily. And that’s to me the future of like, “How do we change inequity?” I think one of the biggest things is we get more people solving for problems that they’ve experienced versus people trying to come in and either solve for problems, to your point, that aren’t actually that big of problems, but it’s like a sexy pitch deck, or people that are trying to solve problems in the wrong way, out of what is good intentions but a savior mentality. And when you think about, just the wealth that comes out of the success stories of venture capital. It’s like, “How do we get more people in the door and how many ideas are left on the table because nobody can get in that front door?”

Wrigley: I am convinced that we have this latent entrepreneurial energy that’s locked behind computers or Target checkout stands or at home with kids because there aren’t enough women saying, “Why not me? Why can’t I be the one to bring this idea to life?” Part of it is access to capital, of course, right? You know, you think you need a quarter of a million dollars to start your business, and fortunately, that’s not true anymore, there are so many third-party technologies and light code versions of getting our products into the world. I’m sure if you were starting Shine right now, there’s so many different things you could do that would’ve expedited and taken a lot of the cost, up-front cost off.

So helping educate women about those resources, I think is crucial to being able to take that step, but access to networks and knowledge are the other two pieces. And so I think whether you’re a local funding ecosystem or you’re an entrepreneur that wants to reach out nationally to other women, I think it’s our responsibility to open the door and, and reach back and bring other women through it with us and being mindful of not just inviting women that look like us, but women that don’t look like us to come through.

And then the other piece of it is, I think we need to make sure that as a country, we’re doing a better job of funding early-stage consumer businesses, because as you said, people solve problems that they personally understand really well. And first-time founders, that is what they do. But for first-time founders, they may have succeeded or they may not right? But we can get them through that life cycle and meet angel investors, meet VCs. And the chances of their second company being either an easier to fund B2B SaaS company is higher, or they’ll be much better at that second company and more likely to bring it to evaluation that provides returns for them and for their investors.

Hirabayashi: And it sets that example. Because there’s who gets the pre-seed money, which is just getting the pre-seed money or seed money is huge, but it’s like 50% of companies get to the five-year milestone. You know, of those 50%, to your point, start doing the math, like the 2% or so of women. And then, you know, as an Asian-American woman, there’s more representation within women than Black or Latinx. But Marah was, I think maybe the 17th or 18th Black woman in the U.S. to raise more than a million dollars in VC funding. Vanity Fair did a really powerful piece on it. And I think it’s where, like you were saying to be inclusive, you have to be specific. If we’re going to talk about what the problems are and what the opportunities are, and the space for more representation, you have to be specific about where we need more representation.

And so, women overall need more representation, but particularly Black and Latinx founders.

Wrigley: In Chicago, we have two Latinas that have raised over a million dollars and I’m one of them. And that quite [was] a while ago, and we’re a big city with a pretty strong funding ecosystem. And most people don’t realize this, but Chicago is actually a third Black, a third Latinx, and a third white. And so we are under indexing by such a huge margin when you think about our overall distribution of race.

Hirabayashi: I have a question for you, and I think Marah probably had the same feeling too, where it’s like, do you feel this mix of like, that’s such pride in terms of what you’re representing, but then like, “Why are there only two of us that are getting that?” just the frustration. What do you think that identity, being a woman, being a woman of color, being a mother, has impacted how you talk to yourself every day, or like risk is such a big part of being a founder?

And I know that’s something I struggle with. Is it’s taken me a very long time to say… just you have to get comfortable with the risk, because I think that’s when we’ll probably have less room for failure. As we have less room for failure and that’s something we carry every single day. So how’s your identity impacted the journey?

Wrigley: It’s such a great question. And I would love your thoughts on it too, because especially as a first-generation college student for your family or a first-generation immigrant, there is a lot of pressure and the opportunity costs of entrepreneurship are actually that much higher because the uncertainty and the risk of failure.There’s no safety net within your family wealth. Right? If you fail, you could really take your family under. Especially anyone that’s invested in you along the way, which is why I didn’t do any friends and family rounds of funding for my companies, because I just didn’t have it within my family.

And I recognize that I present as white and I did go to Yale, and so I know that  I have the privilege of sharing the pedigree, although I’m a woman, that’s still more familiar for a lot of VCs and angels and with that comes a different level of responsibility. I think to get back into, bring my peers that did not go to an Ivy league school or don’t have the CS degree from Stanford, which I also don’t have, but that is a big driver for me and candidly, post George Floyd last year, I just felt like as a founder, who’s had all these opportunities  in Chicago, I went through Techstars, I bootstrapped for a long time, I raised money from Nationwide Insurance as a strategic investor, I raised venture debt, I did an equity crowdfunding campaign on Republic. I was on Shark Tank.

I’ve had all these experiences, and I’m not trying to brag, I’m only saying I need to do something with this because my company is failing because of COVID. And I think my long answer to your question is that there is a tremendous amount of stress around needing to succeed when you’re one of two Latinas that have raised a million dollars in your city. And the pressure to represent is really high. And so the fear of failure slash the reputation piece of this, is definitely something that I struggle with as a woman-founder in Chicago. And I think I’m so lucky to have found and partnered with P33 to build Techrise, because I feel like that experience is not for nothing. That I can now use it and share it and elevate other founders. In a way that they probably didn’t have access to before. So, what about you?

Hirabayashi: That’s really powerful. And I think that the opportunity cost is so real.

Wrigley: Jumping into a business with your friend from work is the riskiest thing.

Hirabayashi: Right, right, right. Oh my gosh I know, and there’s some interesting stat where I think it’s like, if it’s just a friend, stats are low, and if it’s a coworker and a friendship, that’s a very strong dynamic, but Marah and I are really… We say it’s like, we’ve  done more work together than a relationship, we are both married… and it’s like, it’s a partnership and there’s so many different stages to what we’ve done. And I think the thing that was really hard for us in our first year was unlearning a lot of… we came out of a fairly toxic culture in the place that we met. A very toxic culture. And it’s part of why we connected, because we were the only senior women of color on the management team. And there was just… there’s all the work that you do on yourself and with yourself, but then there’s how you go and interact with the world and how the world interacts with you.

And so that was something that we both really struggled with at our old company, and we’re lucky to find each other. It’s been really powerful for both Marah and I to be more open with our experience and our journey. And there’s the experience that we share as two women of color. Then there’s the individual experience. Marah is a Black woman and everything that means in America and then there’s myself  as I’m fourth generation Japanese American so physically,I’m very Asian but I don’t have as much of… because I’m fourth generation, it’s like culturally there’s things that I wish I had a bigger part of my Japanese culture. And so when we first started, from the beginning we were saying, wellness and just talking about what you struggle with, it needs to be a lot more accessible.

And so from the beginning, we put inclusion and representation at the forefront of the company. We didn’t necessarily have an initiative, but it’s like if we can get more women of color in leadership positions, our team is 80% BIPOC and that just happens because it’s just part of our own experience. And it’s when you go to a website and you see people that represent more of what all of America looks like, that’s going to attract a more diverse set of people. And so from the beginning, we’ve said this is really important. What we want to do is figure out how to use our platform, where we’re talking about mental health themes, but there, also… we’re very explicit that that has to intersect with what’s happening in the world. So why we stood out and for example, Apple, one of the big reasons why they gave us that award is because we launched a specific, specific meditations for Black well-being after the murder of George Floyd and in the fight for racial justice.

We recently just did a similar set of meditations for AAPI, knowing that there’s so much happening in our community right now, that is very scary. And there’s just a lot of conversations that are happening for the first time around identity and mental health and all that to say, I think when we first started, the mistake that we made is well… it was always part of the foundation we took ourselves out of it. We said, Shine should be the book, not the movie. We want you to imagine Shine however you want it to be. But we realized that that was doing a disservice. And so in this last year, we’ve put ourselves on the paywall, we launched an About Us page, which is so basic, but just telling our story. It’s like, look, we started this because we were overlooked. Whether it was our body sizes, or past trauma, or dynamics growing up in our families, we just felt otherized in the way that wellness was being sold.

And I mean that doubled conversion, just so many testimonials from our community being like, “I feel seen.” I feel seen for the first time in the meditation space that has been largely appropriated in a lot of ways by a homogenous, white male culture or white culture. And that I think has been a really powerful experience for us this last year. It’s just to say like, “Let’s just be more open about who we are, what we’ve struggled with and trust that we’re doing it with a community that has our back because they’re joining us to take a different approach and it’s helping us grow. It’s helping us grow in our identity. But that’s a lot easier to do in our community than it was maybe in the investor community starting out. I think there’s a lot more awareness now in the VC space because of this last year and the conversations around race that we’re having, for a lot of people the first time, but when we first started, there was a lot of… “Oh, are you a not-for-profit?” Because we come from the not-for-profit world.

And because we’re both kind women and for some reason that just means charity to people doesn’t it? The idea that that can’t be connected to a really successful businesses is a very big problem I think in our company’s version of alpha leadership. And I think because what we struggled with a little bit was… This is again, not all VCs, we’re really lucky we have great investors that are very partner focused, a lot are from marginalized communities. But there was definitely some more of the antiquated, traditional VCs that we met that it’s like, “Oh, I had my daughter, check out Shine. I don’t know if she likes it.” And it’s like, “Well, I don’t know if your daughter is our target.” And it’s like, if you’re a woman, you either, they want to relate to you through their wife, the secretary, or their daughter. And if you can’t relate, if you don’t look like any of that, it’s like, “Well, where do I put you? You can’t just be a potential entrepreneur. And obviously that’s like oversimplifying stuff, but that’s definitely some of the interactions we had. And so I think it’s interesting. I think if we were to go out and raise, now, I’d like to think it would be different. I think there’s an increased awareness around why our approach matters both from a business and impact perspective, but there’s still a lot of change that needs to happen.

Wrigley: Yeah, no, I completely agree. A few years ago when I was raising for Pearachute, I was talking to an investor who came highly recommended, was on a friend’s cap table. And he said to me, “Is it really that big of a problem? My wife figured it out.” And I was like, so offended for his wife and for me and my business. But I was also thinking to myself, “Yes, your wife and secretary also booked your dinner reservations and bought your plane tickets before, but you still funded the white men that solved that problem for them.”

So, why don’t you fund the woman who’s building the business that’s now going to save your wife and your family hours of time and lots of money? And it’s moments like that where you’re like, “Oh, we have so far to go still.” And then you also run into it with women investors. The social capital that women have within their firms, depending on the firm can be pretty low because they haven’t had a track record yet. Right? So, so many of them are early in their careers. And so to stick their neck out for an ultra-female business, is actually quite hard for many of them, which is why you see so many of them are in crypto and B2B and SaaS and future of work because it’s an easier place for them to cut their teeth and have some big wins early on.

And I think that we just need more consumer-focused funds with diverse decision-makers. And I don’t want to say… “I’ve been supported and I’m so grateful for the VCs that have come to the table and said, ‘yes, we believe in you and this is a problem we’re solving.'” But it took so many “no’s” and as women, especially if you’re a high achieving woman, type A personality, that comfort with rejection is… it’s a very painful muscle to develop and so foreign to how we live our lives, right? And so I do think that that’s one of the areas where we as women need to step up and… this problem, isn’t going to get solved for us by men, right? And it’s not going to get solved for us by exclusively women either.

And so if we want to increase, or narrow the wealth gap and narrow the pay gap, and if we want to have more representation by women, we need to do the work ourselves to get more comfortable with failure, with imposter syndrome, with all the things that I think hold us back.

Hirabayashi: Yes. Yeah. It’s so true. It’s so true. To that point of just thinking about getting more comfortable with some of those daily challenges of imposter syndrome or negative self-talk or lack of self-compassion. How do you feel, like that journey has changed for you? Do you feel like there’s been progress and you’re like, “Okay, I trust myself.” How has that evolved for you in terms of your relationship with yourself and confidence in the game?

Wrigley: Yeah, I think that’s a great question and I’m laughing at myself trying to answer it because I think in many ways I treated that as whack-a-mole, I solved it at work, but then it would flare up at home really bad because I wasn’t using the same tool kit to solve the problem.

Hirabayashi: Yes. Oh, that’s very relatable.

Wrigley: Not so much imposter syndrome at home, but self-doubt and not giving your person across the table the benefit of the doubt in conversations. And so a couple of things happened for me that really changed things. So one – Give Forward hiring the CEO and recognizing the lack of confidence in myself. Was a combination of just that, but also a lack of leadership training. I’d never really had a long-term boss and I’d never been a manager before and suddenly I had 45 people under me, and I just didn’t know how to reconcile my vision for the company, with my obligations as a coach, mentor, and leader.

And so I did invest in an executive coach that was really helpful for me in identifying some of my own blind spots as a leader. And so that, as painful as that journey was to lose that company and the potential wealth that could have gone with it, I gained so much so early in my career because I stepped away and did that forced reflection. But then fast forward, and I think I still struggled with some other things, so actually I started seeing a founder therapist, which I don’t know if they exist all over the country, but I very much recommend women finding a therapist that is familiar with the business line that you’re in, and I think it’s so much easier to get to the heart of what’s bothering you in both your personal and professional life. So I would say that’s where I made a lot of progress.

And then I’m also a huge Wayne Dyer fan. So when I go for walks I’m reading or listening to, but I really love listening on Audible and it just reminds you to think about yourself in the context of the world and like, whatever this drama is, it’s not that big, and what’s the worst thing that can happen? And usually it’s not as bad as you think so I don’t do enough meditating, but I do some Wayne Dyer walking.

Hirabayashi: I feel like walking is such a powerful meditation too, but I think walking is one of the most powerful tools we have, if you’re able to do it. A founder therapist is really smart.

Wrigley: Absolutely. I mean, I hope that someone’s listening and starts a business that spins these off like crazy because we need more of them. But I was actually going to switch gears and ask you about, having a female co-founder. I’m curious, how that journey has been? You said you were friends already, which helps a lot, but in some ways, I think that the negative self-talk can be amplified when two women are together and experiencing the same kind of frustration or disappointment. I’m curious how it’s been a benefit, and then how you’ve maybe had to overcome some of the challenges of two women co-founders?

Hirabayashi: Yeah. Thanks for asking that question because I love the curiosity around it because, when we first started, we’ve got a lot of curiosity in terms of belief and interest and this is one form of leadership, because when we first started… another example of some of the toxic masculinity stuff that we had to deal with was like, “But who will win?” or like, “Who will kill each other?” Like, there was a lot of… I think some of that was maybe where they had seen it gone wrong, but there was just no benefit of the doubt of like, “This is a version that works for us.” And it’s like, when you think about what the product is, it all makes sense.

So, I’m very grateful that with time, as you know, and success, in terms of just time, like sticking around and surviving, there’s so much more in our interest in how we’re doing it versus doubt, which has just been nice, because what we’ve said from the beginning is that like Mara and I are very different people. Similar sense of humor, a lot of resilience, a lot of the same values, you know, and you have to have that. But even when we look at like communication styles, communication types, different colors, you know, there’s like, she’s more read, she’s better at decision making.

And she’s just… I admire so much about her ability to like take complex things and simplify them into what’s most actionable. I’m more of like a yellow-green kind of collaborate… I want to get everybody’s opinion. And then talk about it and then qualify it a little bit and then try to move forward together. And that is great for bringing people together, but without Marah’s very decision-driven definitiveness that I find… and conviction that I find so attractive. It’s like it wouldn’t work, just my style alone.

But I think actually, there’s these interesting conversations around, something that’s been harder in COVID with isolation, is when you’re left alone with your thoughts, they can amplify because often how we work through things, and this is true with stigma around mental health, that the way that you reduce stigma around mental health is repetition and awareness. So it’s like talking about things and breaking the spiral of silence about what we struggle with. And I have found my relationship with Marah, and I think some of that might just be having  a female co-founder, and then there’s just things that are very specific to our relationship. She will help… we both have our times, right? There are times where we’re down and we’re doubting ourselves and we’re able to pull each other up.

And the things that we struggle with are different. And so we can help each other see ourselves a little bit more and that reassurance and that feeling not alone, and having that friendship has been so key for us. When we raised our first round in 2016, part of it was that I wasn’t in the venture world, so it was all unfamiliar to me, but it was very hard to find people that looked like us, as well as diversity of personality.

Like what were the personality types that represent what it means to be a successful entrepreneur. And all the loaded history that that typically comes with. And when I think about meeting someone like you, that… all of these, these seemingly day-to-day interactions, and the more that that network grows, the more that we get PR coverage and a young woman reads about us and hears your story of being born in Costa Rica to going to Yale, to my story of being Asian American and going to community colleges. There’s going to be someone that relates to that experience and is going to think for the first time, “Oh, I could do that too.”

Wrigley: I just had a thought too you while you were talking that I realized something that is fundamentally changed too, is the flexibility of what we’re doing right now. Right? Which is that normally you and I would be on a panel together, maybe because we’re both a part of the same portfolio, right? Of a coastal VC, but not like this. And so I guess that one really great outcome of COVID and what’s happened is the fact that there is the flexibility to do this remote work that is not going to go away.

And so it does open up opportunities for women or fractional work, in doing just their job in a way that’s more conducive to the life that they want to live. And I also think it opens up… the freelancer is no longer the struggling, weaving together hours, but is now often a highly compensated, part-time employee of a company, whether it’s a startup or not. And so there’s so much opportunity for women to learn in that environment and think of new ways to use and refine their skills. And so I do think for the women that are already in the workforce that this new normal is actually going to be a long-term advantage.

Hirabayashi: I totally agree. Like being able to have your full self to like… for me, one of the reasons I moved home was being closer to family. And that’s really important. I want to feel like I can be closer to family and parents with some health issues and also run a business. Oh, the last thing that I was thinking about too, is the power of language. When you look at everything from the Me Too movement to the fight for racial justice, to I think unfortunately what came out of a lot of issues with the Trump administration was America getting a better dialogue for talking about what’s not okay. And for example, we did a Daily Shine on representation burnout, and that’s the feeling of exhaustion from being the only person of a certain identity in a room and whether that ends up with you being tokenized or meant to speak to a monolith, that term was something that I think five or six years ago, people wouldn’t have gotten, broad… everybody wouldn’t have gotten.

I think there’s so much language now for women to speak to why something’s not okay. Why something is problematic or why something is a result of toxic masculinity. And we are in an era of accountability for companies, for people in positions of power to be good actors. And there’s more channels to call out that actors. And I think the language, particularly for women to… we’ve been socialized as a culture to always make people comfortable. I think for the first time I’m realizing that’s not my job. My job is to be kind, my job is to be direct, and my job is a number of things, but right now it’s to build a business. And so if something’s not okay, I feel more comfortable speaking to that and why it’s not okay, I have more education than I did five years ago. And I think that’s going to be… that’s one of the things that makes me most hopeful for the future.

Wrigley: Yep. I completely agree. And we did kind of brush over the Me Too movement and it was such a huge decade and both of our careers just… estimating where we are age-wise, and of course I’m sure you have your own stories and I definitely have mine. But I do… that is another level of optimism that I have that what was once kind of okay and quiet or shameful experiences is no longer okay. And we have allies across the board, right, in other men and other women to make sure that… or as much as possible that what was once normal is not allowed behavior anymore.

Hirabayashi: And how many and how many women maybe stepped out of the game because of that experience? That, I hope will be decreased.

Wrigley: Yeah. Yeah.

Hirabayashi: Yeah.

Wrigley: Wow. This was a really amazing conversation. I hope I get to meet you in person.

Hirabayashi: I know. I was thinking the same thing. I was thinking the same thing. And just congrats on everything you’ve built. You are… I was like, “Desiree is so smart.” You are so smart and talented and it’s just been a joy to talk to you and just a helpful practice of being so in it all the time, just taking a step back and reflecting on this last year. So thanks for the conversation.

Wrigley: Thanks.

Uncommon Conversations: Dr. JaNaé Taylor and Katie Hendrix

Dr. JaNaé Taylor: One of the hats that I wear is I have a podcast. So I talked to Black entrepreneurs really about how they build their business and how they maintain their mental health, and it’s so interesting in having some of the male guest on and having them talk about what their business looked like in the startup phase. What is the common theme is that truly, if they are creating a business, then the whole family then is entrepreneurs.

So family members are packaging orders or answering the phones or helping them get to meetings or prep for meetings. I don’t hear that same community support in terms of the household, when it is the woman who is starting the business. So I don’t think it’s because the family doesn’t want to. I think there might be an assumption that she has it. So she’s got it and she doesn’t need this level of support.

Katie Hendrix: Yes, that is it. I think that is it. Let’s just call it. That’s the thought.

Taylor: So they just kind of watched her do all these things and continue to be a mom and partner are is as teacher and all these other things. So I’m always struck by the difference in that, and then when it’s the male led that they really kind of hoist him up to get him to where they need to be in all kind of pitch in. There is this incidence of, I need to kind of manage this to kind of alleviate for women to alleviate some of the strain from my household.

I’ll make it happen. I’ll sleep less. I won’t go outside. I won’t have breakfast. I’ll kind of manage this. I’ll do this when they’re asleep. So I don’t want to disturb the nature of the family to get this done. So there’s a lot of isolation in that. There’s a lot of anxiety that people are facing as a result of some of those things.

Hendrix: You actually kind of made me tear up because it is, I would say just that impact in the way that at least I know for me and I know of some of the women entrepreneurs that I work with too. It’s the way that they, and we juggle our lives is to be able to get it all and carry it all. So as I think through what would these women need? What type of support would they need? How can we care for them? I think there is some, willingness on the woman to say, please step in or be transparent and be vulnerable.

I know that I struggle with letting go of that because I wonder who’s going to pick it up. And so there’s a tension for me, so if I knew that, someone could pick up my child or could help me in this way to apply for a loan or do something that would then take that one thing or one thing a week just to feel that support.

It’s very simple in that way. It’s not even a huge ask. Maybe it should be a huge ask. Maybe that’s what I should figure out. What could that look like to let go?

Taylor: I hope that what we’ve learned from COVID, this pandemic is that the lines are more blurred than we think. So the person who’s leading the meeting is also maybe a mom or a caretaker or a nurturer, but also is doing these other roles too. Having a level of grace and forgiveness as we kind of blend in and out of these roles and ensuring that our children, our families have what we need so that we can show up and be present in the way that we need to.

Hendrix: I would say that’s been definitely some of my most stress is being able to show up still well, in all those arenas. I mean, some days it’s like we’re eating peanut butter and jelly for dinner. I can’t do anything else. And I’m going to answer emails at 10 and then maybe I’ll go for a walk at some point.

Taylor: Right, and eventually go to bed at some point.

Hendrix: Yeah, it is. I felt during this pandemic, working moms with toddlers kind of had it, which I am one of those; had it one of the worst because they were fully reliant on you and then working moms or any moms that had kids who had to homeschool and do the virtual learning. I’m like, “Can I just give you a hug?”

Taylor: If you didn’t feel like you were doing 15 roles already. Here, a few more.

Hendrix: I know, so then think about it. How am I supposed to write a grant or figuring out what a grant is or how do I go to my banker and figure out how to apply for a loan in the midst of juggling I don’t know, fourth grade math. I don’t know.

Taylor: I am a member of our area, Black Chamber of Commerce, and that continues to be one of our biggest discussions. It’s about getting access to capital. How do I even get started? I need money to make money and as you know, kind of that circular… In some ways it can feel like quite a defeat.

Hendrix: Right.

Taylor: That this activity is not going to be able to launch off the ground. And fortunately, or unfortunately, I don’t know how to really phrase that. But over the span of COVID, there’s been these push [00:06:00] to fund small businesses to push minority businesses and women led businesses either through the Small Businesses Association, there’s been the Idea Fund, all sorts of things.

Hendrix: Right.

Taylor: But money is huge. It’s so huge, and I bring that up because I was able to get one of those small grants as a result of this past year.

I did not realize the level of stress I was walking around with and trying to manage the money part as well as do the other pieces until I got the money. And I was like, “Whoa, this is a game changer”, and it wasn’t even a lot of money. It, created a level of relief that I didn’t know I was burdened with it. I didn’t even know it until I got the financial relief. So I think that not only feeling like I need money to make money, I don’t even know where to get money or feeling like I don’t have the proper package to be able to be considered someone worthy, to invest in.

Hendrix: Right, and that’s actually been what I’ve grown to do at CO.LAB is really have that access to capital because, and backing up is that education side of things. I mean, you actually knew about the IDL or the PPP. There’s so many people that might’ve heard, “Oh, it’s a federal loan, I’m probably not going to qualify”, and not go further than that. So, one of the things I represent at CoLab is a crowdfunding loan platform called Kiva and Kiva provides 0% interest loans, a thousand dollars now up to 15,000 and their focus is female and minority business owners, and I’ve had people go through the only needed $5,000. There’s a woman, I mean, she’s one of my… thinking of this topic, she was pregnant right before the pandemic. So I think she had her little girl in April of last year and she has a chocolate business with chocolate from her home country of Ghana, but she’s a teacher in Chattanooga.

So she’s both full-time teacher and also launching this, it’s called Coco Asante, this chocolate truffles, they’re so good and so she did a $5,000 loan with Kiva at the end of 2018, which got her photography, website, and product boxes. That doesn’t sound like a ton when you think about it, both the money and what it paid for. But that then her product boxes, then she was able to bring her chocolates and get them in front of boutique hotels and some other places and have photography that makes her look, while she is still a full-time a complete, amazing business owner that then she was able to get another loan and then she’s been able to go through one of our accelerators. So to your point, that to me is people knowing about it and that’s my heart is that people understand.

So I think you’re right. What does that look like to start a business? Ella still I think she’s finally now, I think at the end of this school year, going to finally be able to move on from teaching and go full time with her business. She does have a husband who does work too, but just having a new little baby and figuring out that balance, of course being a teacher, having a baby, having a business is a different.

I’m the only have the one child and our daycare was able to open at some point and we were able to move forward with that and have him there because my husband and I were both remote at home. But it was hard when he was home because my husband works in sales and had just started a new job. And so it all fell to me when he was home for those few months to basically juggle all of it. So just kind of that fact that childcare for two children and a mortgage for some homeowners is just kind of incredible.

Taylor: It never ceases to amaze me to hear about… in some ways it sounds like college tuition, the price for childcare.Then to add on the space we’re in now in terms of the pandemic is so if I’m furloughed or if I’m already having my own issues with my own employment, how do I then engage with childcare? The level of things in which we’ve had to navigate and maneuver as it relates to childcare and parenting while building businesses.

Hendrix: Yeah. I know of people, it was just, it felt like, maybe after about six months, their bosses were kind of like, “All right, really ?” It’s kind of like, wait, no, nothing in the world has changed. So please continue to care for me with my career and my child. I mean, I had a friend who was working, she has a son that’s a couple months older than mine and just really the stress of her job and trying to care for him, and didn’t want to put him in anywhere and wanted to keep him home in some capacity. So she was one of those numbers. I think, how many women have had to leave the workforce? Are we at 40% over than that I think? So she left just to be able to kind of maintain her mental health and actually be a mom for a child. And it’s just been, it’s just so stressful. Just those pieces of it. So what would it look like for support with careers and childcare.

Taylor: Yeah, I think that it’s interesting how agencies and environments sort of like to think of us compartmentalize as opposed to the whole beings. And when we talk about women who are in these, in these roles in institutions, or even building these agencies, I think we tend to think more holistically that way.

Hendrix: The stress, in some ways of moms and entrepreneurs, just, you’re still trying to run a business, or maybe you have employees. There’s another entrepreneur work who has a cleaning business who, who has had a full-time job as well, but has had a crew she’s had, I think she has maybe up to 30 people and so they definitely had to switch to be able to clean for COVID and then that stress of that. But her business has actually boomed. She’s been seeing such success. I did a panel during, we have startup week in Chattanooga in October, and she was one of the working mom entrepreneurs that did a panel with me. And she told us that her littlest son is six and that he basically, her husband worked third shift and so she just said, she’d be working, he’d be sleeping. And they just kind of rolled together. It was just a good mix. I appreciate her positivity, she just kind of it’s all right. If my child’s sleeping from one PM to 10 PM, this is how I’m working right now.

Taylor: Exactly, the level of flexibility and relieving herself of the mom guilt.

Hendrix: Have you had any conversations with any of the entrepreneurs that you’ve worked with, what they would need?

Taylor: I have earlier this year, I ran a wellness group for a service-based black entrepreneurs called Mind for Moguls. It was not at all about building your business. It was about attending to the entrepreneur behind the business. So we were working on increasing confidence, community, and managing compassion fatigue and two thirds of the participants were working moms, and one of the things with one participant that’s ringing into my head right now is that we spent a lot of time encouraging her and getting her to draw boundaries because she truly felt as though she had to… Her life was not only second, it probably was like fourth or fifth down the line. So she runs a company in which she has to kind of be on demand, people could call her at any moment to respond.

So that was her priority as well as making sure all the kids were fed and taken care of at home and making sure her husband had what he needed. She even highlighted a moment when she was taking a shower and somebody wanted to ask her a question. So she stopped her shower and got out of the shower to answer the question. We spent a lot of time just kind of nurturing her about another 30 seconds in your shower would have been okay. You can finish that shower. And so making herself a priority, figuring out the things that are most important to her. But I think a lot of that had to happen in a space where she felt comfortable sharing some of those very vulnerable parts of herself. Being able to sit with people who are kind of in the same space of building a business, because being an entrepreneurship is still very different from being an employee.

Hendrix: Right, yes.

Taylor: So she felt like, okay, these women understand what this space means. And so they’re saying these things at a space of love and not out of criticism. And so she was able to hear it employ some of those things. And she was also feeling quite isolated. She didn’t get a chance to kind of have a break from being partner from being mom. And so this was her space. We incorporated like meditation and deep breathing. It was truly a healing moment and as a result, they’re now meeting monthly to continue to on that space. I think community is big for women. It is huge. It is huge to be able to sit and talk about your needs as a business builder, your role as women, and then even some of the things that are also popping up in a larger context.

Hendrix: Can we do that in Chattanooga?

Taylor: Yeah!

Hendrix: I already have some entrepreneurs and in mind. I just think when we did that working moms panel I kind of had a variety of some single moms, I had some moms that were full-time entrepreneurs, I had some whose husband kind of ran the business, but she had the full-time job. So we all found community in that regard. We all look differently in the way in what we did, but then we all felt, oh, you get this, and kind of what you’re saying, as far as that space of feeling cared for, because I think our minds attack us enough of, how can I juggle this one more thing? I mean, even last night we had our first kind of in-person event that we were able to attend outside.

I was supposed to have some help with my son and picking him up. And on my way to the event, I get a call for the day it was, “Are you coming?” I was like, “Oh, other people were supposed to come.” So I brought him with me and I walked in insecure a little bit to be, okay, bring it in and everyone was gracious and kind. I was thankful to have that support even as I kind of was unsure, and he was fine. It was outside. So he could do whatever, he got to know everybody. But it is that I think that community and sport. I have another friend I just met with, that’s looking to help. She’s launching a business to help entrepreneur moms, either both professional or personal with all the things, she’s like, “You need me to go pick up your child” or “You need me to get your dry cleaner, and you need me to balance your books”? “How can I be support to you so you can breathe?”

How are those sole providers for your family if you’re doing all the things? How can you have support?

Taylor: Absolutely.

Hendrix: Yes, so even what you talked about with your Mind for Moguls, can we bring that down to Chattanooga? I’ve got people. I think that’s the part that at least in Chattanooga, I’m thankful we have a great entrepreneurship community where resources all come together, but we don’t always get to everybody, and I want more people to know that they’re not alone. There are resources just in general, not just about capital and things like that, but how can we as a community come around you?

Taylor: Mm- hmm (affirmative).

Hendrix: Are you plugged in to other, I mean, you talked about the Black Chamber of Commerce?

Taylor: Yeah, so I’m plugged in there. I’m connected with some of the other black therapists in my area who have, and a large chunk of them have private practices. So monthly, we do a meetup and that really is to be a space where we support each other. So I have my little pockets where I kind of go in and out of staying connected with black entrepreneurs and one of the pieces, we’ve been talking about like the role of women and being a parent in an entrepreneurship, even when I just said, in terms of being a mental health therapist, doing this pandemic as an entrepreneur, this is a whole, another thing.

So being a Black entrepreneur in this space has been really interesting because we are in this environment now where we’re having to manage safety on multiple levels. So, COVID is one thing, but then the physical safety of the incidents of police brutality and racial justice, and sort of watching these cases happening and having to sit with people, if you’re a service-based businesses, having to sit with people who are, who are really suffering too. And so it has been a lot and trying to manage all of those heavy, heavy, heavy.

Hendrix: Right. You mentioned this kind of monthly, but where do you go to be able to care for people as your own? I would assume your own emotions too, that you’re-

Taylor: Right, right.

Hendrix: You know, who cares for you in that regard?

Taylor: I appreciate you asking that. So, I’ve employed a lot of strategies and some of the strategies that I employed last year are different for new ones this year. And so I’ve changed my schedule in terms of when I carry client hours. My day is not as long as it used to be, which is nice.

Hendrix: Yeah.

Taylor: So that has been really helpful and last summer for about two or three months, I went back to therapy. That was really nice to kind of deal with the multiple levels of grief that was happening as a result of the world changing.

Hendrix: Right.

Taylor: Then, I of course have my own support system, my family and friends that I tag in as needed a lot of video calls or even, meeting six feet apart and a lot of that happening. Most recently, what I’ve decided to do is be more intentional about taking breaks. So like a quarterly break where I just kind of stay up to step away from the business with three or four days. Last week I got to go to Williamsburg, which is about 45 minutes north of me. And just kind of being with the cherry blossoms. And I saw a family of deer, and I was like, “I forgot outside was like this.”

Hendrix: Yeah. Oh my goodness.

Taylor: So that did wonders. And I was like, “I can’t stay here. I have to go back and make money so I can come back.” But –

Hendrix: The crux. [inaudible]

Taylor: Right, so I’ve been trying to employ as many things that I can, and I now have this. I’ve gotten more houseplants than maybe I needed at this point.

Hendrix: Me too! Yeah that’s funny that you say that. I’ve got a lot of flowers.

Taylor: So, you know, I just kind of do what I can given where I am today. You know, we have been talking about some of the things that women entrepreneurs manage, moms managed, mompreneurs I’ve heard that word. So in terms of the mom guilt, the what I like to call an entrepreneurial anxiety for some of us who are struggling with a lack of community There’s a large group of people who are running small businesses, who are not at all connected with other small business owners and so sometimes they’ll minimize their own stress and struggle because they don’t realize that they’re in a space where they’re kind of operating unhealthily there.

So I would suggest, I’m completely biased and I recognize it that I think everybody, all entrepreneurs, particularly mompreneurs, women, entrepreneurs need to get connected with a mental health resource. For some people, when they say, when I, when they hear me say that they think, oh no, I’m suggesting you go to counseling.

Ideally, yes, but I also know there’s some barriers to that too. But some therapists are working to create systems where you don’t necessarily have to come to therapy and still get support and resources and education. So whether that means listening to the podcasts, whether that means attending a workshop that they do, or something where you get an education about how your emotions are impacting your ability to think and stay motivated and to have energy, to do the things that you need to do.

So I think there’s a lot of like self-discovery or even reconnection because we’ve changed by the pandemic. We’ve all been changed. So that’s kind of the inward and then getting connected to the entrepreneurial spaces. That’ll be really helpful cause that’s going to help lead us to that education that you do, Katie, to help, to help people manage and maintain their business.

I think it’s important to talk to your family about what you need and to not try to compartmentalize that in a way that don’t worry about it. I have it, no, let them help package the orders.

Hendrix: Right.

Taylor: I remember my mom’s an educator and I remember going to her office after school and sitting in her office and watch her do her thing. And they gave me such an appreciation for what she does because I was watching it. I was seeing it in real time. Now I couldn’t help her. Well, that’s not true. She had me staple.

Hendrix: I staple things.

Taylor: Look, I even played with the Scantron machine, I don’t know if I’m supposed to, but, I felt connected to what she was doing and I don’t think that moms have to live that way that things are so separate. I see some beautiful examples of where other mompreneurs are, taking pictures of their kids and their workspace with them, helping them do these things. So you don’t have to do that. So asking for help is not a sign of weakness, it’s a sign of strength. And so we are already sort of extending ourselves and a lot of ways beyond capacity and that’s not necessary. I think when we business builds, sometimes we feel like it needs to happen in certain pace and fashion and we get caught up in comparing ourselves to others and feel like we need to go faster and faster and faster. And that’s not necessarily the case. Sometimes you do need to slow down and pause, get some support. Don’t try to do it by yourself.

Hendrix: Yeah, I totally agree. I think that place of coming to appreciate yourself and know yourself and take that 30 seconds more in the shower, maybe take a shower and make that a priority. You know, don’t just be living out these titles of these roles that you take on, but, be who you are and I think what I’ve seen in the workplace, I was the only mom, I am the only mom out of my organization. So one of the things that we’ve talked about in leadership is seeing other leaders be able to say, Hey, I’m going to go pick up my child right now, or I’m going to go to a baseball game but just being able to show that transparency, that family matters and that then you’re empowering the others in your organization to feel. Because I literally on my calendar have a time where I can’t have meetings after, because I’ve got to get to the daycare to get my son to do all the other things, some of the other job.

I think seeing that in support that people know, this is not something we have push up, it’s still happening. Let’s be transparent in that and I think just coming with community and knowing that you’re not alone. I think that piece as I’ve gotten to talk with more working moms and entrepreneurs, and we’ve all just been like, this is where I am.

Taylor: Mm-hmm (affirmative).

Hendrix: And that vulnerability I think has just happened way more in this past year than I’ve had in other seasons. So I hope that people are finding that community and being able to lift people up and support. I had someone yesterday at the school be like, “Well, do you want me to take him? Cause I know you have your event?”, and she’s a single mom and if we had had an extra seat, she probably would have taken him, but we couldn’t figure that part out.

I was humbled by her generosity to help me in that moment. And she had two kids she already. I think that everyone coming together in a way that’s just beautiful and generous and that people can do. I mean, we’re all affected this way. In a unique, awful way. As you’ve said, I love how you phrase things kind of for unfortunately, but then fortunately the positive way of it.

Taylor: Yeah, I agree.