Permission to Do Things Differently with Rachel Romer

1,000 Stories


REID: Okay, Joe, so next guest coming on the show Rachel Romer, who is somebody who has done a lot of really big things, just has, as with many people that we have on the show, very interesting career path. But by the nature of the scale of her accomplishments, she has somewhat of a. Public persona has been in a lot of places.

And so one of the things that we discussed prior to coming on the show is, what can we explore with her that is different than a lot of the conversations that she’s had historically? And so with that context and with that goal for the conversation, I’m curious where your head’s at in terms of where you do want to go.

JOE: Yeah.

Here’s what I don’t want to do is I don’t want to get the story of Guild again. Mostly because it’s been, you can go on Google and type in Rachel Roamer and it’s like, Everywhere. It’s like, how did Guild start? Where’d it come from? And she comes from a family of educators. So there was clearly this seed in her head sitting at the table.

She talks about it sitting at the table with her parents talking about education. And then she has a dual master’s degree in education and in business. So clearly education’s been a big part of her life and I don’t want to like sit in that point. Right. And so what I really want to do is a few things. I wanna future cast with her a little bit.

Like her company focuses on enabling. Employees to skill up and advance in their career. Well, we’re at this point in time for the last, I don’t know, let’s say six months, that people have been freaking out about AI taking jobs. We’re in a moment where upskilling seems very important and career development seems really important, and I’m curious about her perspective on that topic because I don’t think anybody else who we’ve talked to is in the same.

Positioned to speak with knowledge and with confidence about what she could see the future looking like. So that’s one very particular thing I wanna talk about. Another one is she mentions in, some prior interviews that the companies that win are the ones that have a combination of purpose and profit.

So having a mission and having a margin is another way that she put it. And I wanna know if that was learned or. Ingrained in her, like did it feel second nature or did she like get that lesson somewhere? Going back to this idea, a little bit of what we talked about with Nick Melli around like talent versus nurturing or like inherent thought versus something that you, like, a skill you kind of develop and I wanna get her perspective on that.

and then speaking of intuition, so. Already, I can see a few big moments, like in the trajectory of guild that she talks about, like moving the office from Palo Alto to Denver. the way that they give equity to all of their employees. these are some like big, like people moments. And I would love to unpack with her if that’s intuition based, if it’s data database, if it’s both.

Kinda get the hunch from listening to some of her other conversations that. She’s pretty data driven, but also like thinks from the heart. So I’m really interested. That’s a really powerful combination of skill sets. So I really wanna hear how she thinks about it.

REID: I think it’ll be interesting after the conversation to us, for us to actually reflect on. What parallels exist between both her mentality around business and entrepreneurship, and then the business itself with Element three?

Because, as you’re speaking of things like upskilling, you know, we live in an environment where it’s just a place where people are constantly trying to get new skills. there’s no sort of resting on your laurels, right? Yeah. and the combination of. Purpose and profit. Purpose in business is something that is obviously inherent to element three, but also in terms of many of the other podcast conversations we’ve had, the businesses that we like to work with.

So I think it’d be interesting to do some pattern matching after the conversation as well and see what parallels exist there that we could think about.

JOE: Yeah, totally. That sounds great.

REID: be awesome.

JOE: All right, Rachel, welcome to a Thousand Stories. Thanks so much for making the time for us today. Really appreciate it.

RACHEL: for having me.

JOE: Your list of accomplishments is very large, and the scale of them is extremely impressive. What I’m curious about just as to get people off the start line, is your job title says ceo and I think CEO can mean a lot of things even over the course of time and, I’m curious about in, in this moment.

In time and what you’re currently dealing with inside of your company and inside of your life. where do you see yourself focusing right now, and how would you say this is what I’m functionally doing inside of my work at the moment?

RACHEL: I love that question. one of the funny things about being a founder is that you’re supposed to anoint yourself ceo. that’s sort of the ultimate dish of imposter syndrome, right? Because at all times, you just.

You gave yourself that job. nobody hired you or anointed you. And so founder has always really felt more like a familiar and comfortable title for me. and early days I really identified there. And then there was this point as we got a little bit bigger where I felt like, okay, time to be a ceo.

JOE: And I joke that I felt like I had to like, put on my girl boss Blazer and like figure out how to be the CEO that I read about in Harvard Business School cases. Channel your inner Sarah Blakely maybe.

RACHEL: Yeah, maybe. And,it might have fit her better cuz that blazer didn’t fit me well and I felt like I lost some of my authenticity.

I wasn’t playing to my strengths and I was totally playing to areas that were uncomfortable or weaknesses for me during that chapter. This is probably 20. 17, 18, 19 at Guild. and luckily, 2020 kind of knocked us all down in the dirt and to use a Brene Brownism though, like, in the arena, I was face down in the arena summer 2020, and it became pretty clear to me.

and thanks to great executive coaching and mentorship and advisors that I had sort of on speed dial during that time, that if I was going to. Do this job anymore, I needed to figure out how to do it in like a cardigan that fit me, not that blazer. And so I started rewriting the job description of CEO for myself and stopped trying to be the CEO that I felt like I’d read about or that I looked up to.

Cuz we work with Fortune 500 companies at Guild. And so a lot of the CEOs I admire are these folks who did train their whole career. They were executives at every stage of a company. They did, build into becoming, a hired c e o and really getting comfortable. They’re like, that’s not my journey.

I’m a founder ceo. And that comes with a lot of strengths. and so, and it comes with weaknesses and I can hire folks to do those other things that a great hired CEO might do. So for me today, to answer your question, I spend my time, first on, on vision and strategy, thinking about guild’s tenure and three year, kinda think of our tenure as the vision or three year as the strategy.

across, all elements of guild, the, our solution strategy, our product strategy, our financial strategy, and our people and culture strategy. I then spend a significant amount of my time with anyone. We partner with employers, universities and learning providers, future ecosystem partners.

and that’s where my zone of Genius is and we focus a lot on that. On Guild, how do you play to your zone of genius? So I do my best work there, and relatedly in, in our brand space and we just did a rebrand. And then lastly, I spend my time thinking about making sure we have enough cash in the bank.

so I, I manage all our fundraising, I manage our board, and I think about our corporate governance and our financial, near term and long term strategy there in partnership. And then the last is I try and lead a high performing team, and that part felt, That’s probably been the biggest stretch area.

it wasn’t a natural zone of genius of mine, but it was something I really wanted to be good at. And I felt jealous of the folks who had led teams for decades before they had become CEO or become a leader. And I skipped all of that with how Fast Guild grew. And so that’s the fourth area that I focus on a lot. And I’m always growing and learning.

JOE: Yes. the summarization is a lot. you do

RACHEL: but I don’t do a lot of the other things that ceo, you know, there are CEOs who do a lot of other things that I’ve really learned to take off my to-do list cuz they’re not in my zone of genius and I can hire great executives to do some of those things.

JOE: the thing that came to my mind is I wanna take us back to 20 17, 18 19, and you being face down in the arena.

RACHEL: what did that look like? Like what was functionally happening in those moments? Yeah. it’s a little bit like a snowball effect. You don’t know the snowballs building until suddenly it knocks you over. a couple different things. One, the company grew really quickly, so we, were four employees when we brought it to Denver in 2016. by the time I went out on maternity leave for a very too short, and that was my own decision and my own, ramification.

In 2018, We were marching towards, 180 employees. And then by the time Covid broke, we were 400. So pretty exponential scale and none of those stages. as a founder, that growth felt really natural. Like I just believed in what we were doing so deeply. The product was resonating the market loved the product.

Like from a go to market perspective, it just felt like firing on all cylinders. But, how to hire the right leaders at each stage, especially cuz we kept growing out of stages. It was like by the time we’d hired the team for the stage we were in, we had outgrown it and it felt so, it was like the growing pains that you imagine a teenager having where their pants keep getting too short.

that was going on. I was becoming a new mom, which both was really complicated and a huge blessing. Think it actually gave me some of the gift to decide I wanted to be more comfortable in my skin and just be the kind of leader that I wanted to be. Motherhood gives you a lot of chance to revisit some of those conversations with yourself.

and then the backdrop of but beyond hypergrowth, than Covid hitting us in 2020 and we were fully in person, 400 people in the Denver office, everyday business. And then all of a sudden we were all sent home. Meanwhile, a month later we closed an acquisition of a hundred employee company out in the Bay Area. So everything changed. Yeah, is the real answer.

JOE: Yeah. Well actually that’s where I wanna sit for a second because one of the things I was thinking about, and one of the things that we unpack on our show is really these inflection points of change.

And so I was gonna ask you what are the maybe top three big inflection points, but I, I think you just brought one up. You were a fully in-person company that then purchased another company outside of your network. So now it was not gonna be all in one space controlling the culture, all the pieces.

and then also it’s very interesting because your, the thing you offer is digitally in, engaged with. And so there’s this interesting piece where if you were to ask me from the outside without asking you, And I’d be like, I imagine that they have lots of infrastructure for doing things remotely and that they were already in that game.

but it sounds like that wasn’t the case. So I’m curious about how you, let’s talk about navigating that point right there, where people are no longer in the office. we have to also onboard a new group of people and get them inside of the guild, what it means to be a Guild employee versus where they applied to work and just all those changes. Like take me through some of

RACHEL: yeah. So the simplest way to say it is that I would say from a hardware and digital perspective, we had all the infrastructure, we had an easier transition than most companies. Everyone could basically do their job from home in April, 2020. From a cultural perspective, we were totally unprepared. we really had a culture that was, very.

I don’t know how to describe friend based, like a lot of people made their friends at work. We had a lot of folks in their twenties and thirties. The office was also where they got a lot of joy. we had a lot of folks who were single and suddenly back in, studio or one bedroom apartments feeling a lot of loneliness in the situation of covid with both work and their social lives totally halted.

and then with the acquisition, we hadn’t prepared at all to do that acquisition fully remote versus bring them all to Denver and incorporate them into our culture and then help their San Francisco office become a guild office. And all this stuff we had planned suddenly was impossible. So it was that cultural infrastructure that we were lacking. That said, it was sort of a blessing because I now think we’ve built this tremendously successful culture that really works for us in that.

dynamic. And I find myself in rooms. It’s something I feel like I can confidently speak about with Fortune 500 CEOs now about how we’ve navigated it and the success we’ve had in building, a fully distributed culture, but with a spiritual headquarters of sorts in Denver. Very few people work there full-time. In fact, almost no one does. But, it’s where we have all of our offsites, all of our events, all of our, ERG leaders are brought there on a regular basis. All of our manager, you know, we’re really building it as the home that we come to gather as teams. So it’s working now. 

JOE: what broke first when everybody went home, where’d you first notice like, oh, this is a challenge?

RACHEL: I don’t wanna call it full blown trust, cuz that’s a heavy word, but sort of the generosity of intent, the assumption that everyone was, doing their best and what I realized was, I don’t think that was just covid. I think that was also the chasm of crossing to 500 employees. And I’ve read a lot about, these sometimes over extrapolated studies of how humans operate in a group of 5 50, 1, 50, 500.

There’s all these sort of truisms that look back at, tribes basically in terms of the size and how we operate. But there’s a lot of evidence that 500 a lot breaks down. And we didn’t contemplate that alongside the acquisition, alongside Covid. And so suddenly, once people didn’t know each other and they didn’t have enough, base and that base we had always built at Guild through familiarity and knowing them and seeing in the hallways and events and social, suddenly, once that was stripped away, we lacked a strong foundation to then build.

JOE: Generosity of intent and trust on hard decisions, and we were making so many hard decisions that summer. So that was where we really had to rebuild and find a new way of how to build trust within the company. Yeah. What came to my mind when you were saying that is, our ceo, Tiffany has a framework she uses for. decision making and part of it is, communicating it to your employees, obviously. And the question for them is not do you like it, but it’s, do you understand it? And what came to my mind when you were talking about that foundational trust piece is like you can stress a system with decisions that people don’t necessarily like when they.

Understand that you have their best intent or they like have that cultural or that like relational belief where it’s like, I may not like what’s happening, but I trust that the decisions being made in our best interest. And when I have that trust, I can take the impact of the decision and bounce back from it very quickly or absorb it and be fine.

And when that doesn’t exist, it feels like a board that doesn’t bend with it. It like snaps and then you have this sort of, Chasm of like, well, why are they making that decision? And I, it’s not good for me. And then it becomes these like, pockets of problems is what I’m perceiving. Is that 

RACHEL: That’s ex, yes, exactly. Exactly. And especially in an acquisition scenario, suddenly there’s a hundred folks who wake up one morning and get told they work for a different company that they didn’t sign up for. Right? Like I, I always think of employment as a two-way decision. I. I’m hiring you at Will and you’re choosing to join this company and then show up every day.

and that’s really, I think, a healthy social contract. And I think Covid has forced us all to reevaluate those. But we were reevaluating them at the same time as these folks were sort of, put into an arranged marriage with Guild. Now it ended up working out quite well in the rear view mirror cuz our cultures were quite similar. But they didn’t know that and they didn’t have any reason to feel like, well I signed up for this. It was more, it happened to them on the onset. 

JOE: Yeah. That’s so interesting, happening too, versus like self opting in. And the way that changes. but have you acquired any companies since?

RACHEL: we have, we’ve done, one other small acquisition and I think one of the main things we learned, and we got this right about a month after the acquisition. But, a big change we made was, we hadn’t quite figured out. We knew how a lot of their roles would slot into guild. but it was an education consulting and advisory firm. So a lot of ’em had a lot of domain expertise on lots of things we did. And So, the change we ultimately made is we gave most folks more than one option to choose which team they joined at Guild. Rather than saying, here is your new job title, here is your new boss, here is the team you’re on. We actually did an open house, a zoom open house where you could go meet the teams and meet the managers and you were given a list of like, look, if you’re a, education consultant, you’re not eligible for a job on the technology team, but you are eligible for these two different jobs. Go meet those leaders in teams and then rank for us which one you’d prefer to join. And that shifted it to more of an opt-in decision that I think served us really well and is a playbook I’ll use again. 

JOE: Yeah, that’s very interesting. That was exactly the question I was gonna ask. The other thing I’m really curious about this idea of having a center point that is like spiritual center, which I really like your language around that. does it feel like as somebody who’s located in Denver, 

If I’m in San Francisco, And I’m coming to Denver. It feels new. It feels exciting. It’s like, oh, I’m here for an offsite. It’s kind of an event. it’s a big deal. And if I’m imagining if I live in the place where the HQ is and I have the ability to go in when I want to, it doesn’t have that same sort of magic to it. I’m sort of putting that assumption out there. I’m curious about what your experience has been, with creating specialty around the space.

RACHEL: Yeah. You know what’s interesting? We haven’t. Yet made a big investment in changing this space other than we got rid of a lot of the desks and we created a lot of like living room type of settings. Cuz what have we all done in the last three years? We’ve all worked in our living room, but we made like big living rooms where 15 members of a team could all sit on couches.

Cuz if you’re there to do leadership training, you don’t all need your laptops. You don’t need to sit in a conference room or in a, a hall. So we did that. so I don’t think I can say we’ve done a lot to like, make it more special for the Denver folks and about half of our employees do live in the Colorado, region and really in the Denver Metro.

So within an hour. but I can speak for myself, I guess is the best I could do, which is I was just in there yesterday and I go all the time cuz my kids go to our daycare, preschool. So I drop off there all the time, but I don’t go spend a whole day in the office that much. Cuz really as noted, we don’t, like, I don’t go work there.

I only meet and spend time with people there. And it still feels special because it’s the people. So I was there yesterday and our finance and operations teams were on site and they’re from all over the country and I hadn’t met a lot of them in person cause it’s a team we’ve grown over the last six months.

and it still feels special. So the people make the magic. But I think the central home is really great cuz it actually just means you plan more. I think there are companies who are still trying to do a different offsite somewhere every quarter and there’s so much logistical barrier to doing that.

And then when you push that down to a frontline manager, I mean, not so much work for a manager to go plan on offsite, even if you give ’em a budget. We have a team that’s built playbooks of how do you host an offsite or anite as we call it.

at HQ and all the resources, the catering. You need a fun evening activity for team building like ax throwing or a cupcake making, bakery that hosts contests and those kind of things.

And so having that playbook, I think has made it more likely that leaders. Bring their teams together, and that was a high hurdle. People were really nervous to do that for so many reasons in 21 and 22, but we were also just out of practice about how to host. 

JOE: Yeah, that makes sense. and obviously you always hear it about like the bigger companies, the alphabets, the apples, those people with like, their space and, trying to make it a space where people. use it for meeting, use it for like, with intentionality instead of being like, you have to come back to the office and now you see ’em resorting. They’re like, you have to come back to the office. which is a thing in and of itself.  One of the things I’m curious about, when I’ve read other things that you’ve talked about and listened to other things that you’ve been on, you do a really nice job of backing up what you think with data and there feels like a very nice, interaction between what your gut is telling you to do and what like hard fact is telling you to do.

And I’m curious about two things. First, is that how you see it as well? And then second. When you made the choice, to move the office from Palo Alto to Denver, and that felt like a personal decision that you then were like, let’s see if this also works for the business. But I’m curious about which direction that went. It was like, it’s gonna work for the business now it’s personal. If it’s personal first, like, kinda wanna know how your intuition works around that.

RACHEL: Yeah. I think I’m on a journey on that. I have a very strong intuition, but I wasn’t particularly trained to listen to it. and I don’t know that. I was built to, I don’t know if you’re an Enneagram fan, okay, I identify as an Enneagram three, which means I sort of, left to my own devices.

I believe what the world tells me before I believe myself. So I spend a lot of time trying to listen to my intuition. But when I do, it’s actually quite strong. And I often find it by finding data that helps me go, Oh I was already leaning that way, or, oh, it’s in my bones or in my gut, and so in that instance, I knew I couldn’t build the company I wanted in San Francisco at that time.

And I wouldn’t say it’s changed much. But for me, look, for me personally, looking at what it took to hire engineers, the cost, the lifestyle, of. What founders I knew were doing in San Francisco in 2015 and 16. and then the lack of role modeling I had, I didn’t know any other female founders, at the time who were raising kids in the city.

It just felt impossible, but I knew what entrepreneurship in Denver looked like. It wasn’t sexy yet. Denver was, I think might have heard me say this, but if you listen to this, but I literally, tease him to this day, but I had an investor say to me like, it’s the Renaissance and you’re leaving Venice about the idea of moving from San Francisco to ho bump Denver. but that’s how people felt in 20 15 16. Like it’s amazing how fast tech diversified, even in the late, 20 teens. And then of course, COVID blew that all up, but it felt like a really risky decision. but it was my gut. I knew that if I was gonna do this and accomplish, you know, I had ambitious goals for guild, but I also had ambitious family goals.

And if I was going to have both, and not risk putting off the timing of when I wanted to have children, I needed to do it. And then I did go and build data and build the conviction with the investors. But I knew it was out there cause I had spent enough time in the Denver ecosystem to know that there was talent there. 

JOE: Yeah. two places I want to what about San Francisco said to you, this is not going to support the lifestyle. And company style of what I want to build. What was the gap there? What was gonna miss from your vision?

RACHEL: two core things. I’ll start with personal though. I used to be too nervous to talk about it cuz it felt selfish. But I now feel okay cuz I, the choice I made has let many, many women and parents make the same choice at Guild. So I believe a lot of the ease or difficulty of parenting is about the community you’re in. I’m a, it takes a village person in terms of raising children. I sort of believe the village was the ideal way that children used to be raised. and today I live in a, basically a village, though I live in Denver. I live, within, four or five blocks of more than 15 family members. My sister and her kids live down the street.

My aunt and uncle live across the street. We all live within the neighborhood where my great grandfather used to be the pastor at a local church. So, the fact that when the flight’s delayed, I have 10 people I can call to drop over to my house and let my babysitter head home if I’m gonna be late. That’s such a gift. I was watching so many folks try and raise their kids in what I’d call like the nuclear family of, it’s a mom and dad and just the kids. And both those parents were working and they were drowning. And I, that was the only crowd I knew,in San Francisco at the time. And they just felt like they were trying to do everything themselves. And I wanted to raise my kids in a community that let me fulfill my career obligations, but also feel really great about the way my kids were growing up. was,

JOE: that. That’s amazing. I know there’s a second point, but I want to touch here for a second. my brother-in-law is from a small town in Italy and, he’s more Italian than he is American, although they, he and my sister live in Chicago. we were over in Italy for their wedding and one of the things that struck me very, very acutely was, when you’d walk through like downtown of this smaller town, there were just like kids running around everywhere and.

They were ages, probably everything from like eight to 12, sort of that age group. And I’m thinking to myself, this would not happen in the United States. I’ve never seen this before. I haven’t seen it. I lived in Raleigh, I lived in Tampa, I’ve lived in Indianapolis. Like I has never seen this anywhere.

And it got me thinking about how well we were in their town and my brother-in-law’s. grandma was around his family, his immediate family was around, his aunt and uncle were around, like his cousins were around, and it’s like, that’s probably everybody here, or at least the vast majority of the people here.

And it does create this ecosystem of people who are built around you and. One of the things that it showed to me, and this is what I love about traveling, is that it opens your eyes to like, you see yourself and you’re like, wait a second, this is the only thing I’ve ever thought was possible.

And now there’s a different way of doing it. we are so intent in incredibly independent in the United States, like, and I think there’s really huge benefits. it’s people like you who are willing to take a leap and be like, I’m gonna start a company that’s like an independent movement, but then like, it also eats the positives of community sometimes.

RACHEL: Yeah, I think it’s, I think it’s super complicated. and I think a lot of the, Silicon Valley myth and legend is around being like a single 20 something male and just to even stretch this stereotype further, often heterosexual white male. that profile can, live in a.

Studio in San Francisco and hustle and do what they wanna do, to build their company. And it really works. The system works for that person. Right. But as you think about more diverse founder profiles, whether that’s age or gender or desire to be in a community or even just, cities are less safe for single women who might not wanna live there.

Well, you name it. I think the fact, I think this is a real benefit of covid, I think entrepreneurship is now so much more geographically diversified. This idea that you need to live near the capital. Cuz that was the commitment my board asked me to make is, okay, you can do all this, but the board meetings stay in San Francisco. So I committed to come back four times a year. It’s two hour flight. It’s like as long as a Bay Area commute, right? It’s like the same time I would’ve spent in the car. so I agreed to do that and I ended up. going back even more than that. now nobody cares. we’ve one meeting a year in San Francisco, one in New York, one in Denver, and one remote. And so, so much has changed, but I’m really excited about what it might do for opening up opportunities for more diverse founders to raise capital. 


JOE: One of the things that, you asked if I like the Enneagram. I’m a massive Enneagram 

RACHEL: What are you, what do you identify as? 

JOE: okay. Forever. I thought I was a three. 

RACHEL: And I actually lately in probably the last six months, there’s some real intentional like conversation with some coaches and my own discovery, I think it’s very important, Enneagram, is about self discovery, not taking a test or anything.

JOE: I believe I’m a four 

RACHEL: the thing that I have always, but I have a very strong, like three tendencies. Like a lot of people experience me as a three and. I think that comes from trying to meet perceived expectation from somebody out there that I can’t really identify what has always been impressive to me and what you did moving your company is that, you actually had explicit expectation to keep it somewhere and you were like, I’m gonna do what I think is right here.

JOE: And I’m curious about like, where does that come from? Where does that sort of like confidence or belief or something, where did that come from?

RACHEL: Doesn’t come often. I work so, so hard when I’m going to, make a decision that runs counter to somebody else. I’ve done a fair amount of work to realize it tends to be most. intense. If I have to push back on an elder or somebody I really respect, I have an easier time, being the provocateur or taking, perceived social risks with my peers, I did as a kid. but when moving the company or a number of other decisions I’ve made since where I fear disappointing these board members, I really look up to, or advisors or investors, it really stresses me out. But I think at the root where it, where the, where I ultimately can sometimes find the confidence is, I grew up in a really entrepreneurial family.

and the entrepreneurship was almost always in the public sector, which is so rare. But my grandfather was sort of a renegade, politician. he was very opposed to the Vietnam War while serving in local office. And then he ran for the US Senate and. not only lost, he was actually kicked out of the Democratic party in 68 for his anti-Vietnam stance, which now, like, you have to remember that one year of history to remember that the Democratic party was also anti Viet or was pro very pro Vietnam in 68.

And then he left the party for 10 years before rejoining. But he talked a lot about, like, then he just went and was an entrepreneurial lawyer and started all these businesses. He is like Forrest gum almost in how many businesses? He started a ski hill and,he taught people how to fly airplanes and opened a school to teach flight, and invented a competency based teaching model that them, he put into a university later in his life.

Like he did all these crazy things, but like if you had just said, oh, he is gonna take all these risks and then get kicked out of the party at the moment of trying to achieve his dream of serving in a broader office, US Senate. That sounds like the end of a story, but he actually was like, no, guys, like, you take risks and then you figure out if it, you don’t take risks on your livelihood.

Like, you don’t, you make sure you’re alive and well, and you make sure you can feed your family and pay the bills. But beyond that, like, go figure out the next thing. And he did. I think that gave me a lot of comfort that as long as I was staying true to my values,I could risk losing a company even if, like I, I have never operated as though Guild is, the only thing I stand for and that gives me some comfort. 

JOE: Yeah. That sounds like you’ve been able to separate your identity from the company. 

RACHEL: Slow so slowly, but 

JOE: Yeah. Well, I mean, very impressive though. Like what’s that pro, how have you done that? Because that is very hard. I don’t own element three and there’s a large chunk of me that is somebody were asking me like, oh yeah, who’s Joe? Like, part of my response would be a lead sales for Element three. Like, that’s part of who I am. and I’m curious about how, like, has it been very intentional to get that separation or how have you 

RACHEL: hugely intentional. So I’ve had an exec coach since the day I started Guild, and that work has been, and I’ve had a couple different coaches, but I’ve had, one consistent coach near weekly for now, eight plus years. I’m really dedicated to that practice, and find it? really grounding for me. And I bet in, six out of those eight years, the identity work of Rachel v and Guild has been on the table. The things that have helped most beyond the consistency of self-awareness and knowing that I’m, as a three or as a entrepreneur or as a founder, all these things make me very likely to intertwine my identity with my company.

starts with the self-awareness, then you do the work. But, the things that have helped most,well, motherhood helps hugely, cuz you actually have to do the same thing as a parent. when you’re pregnant and when they’re infants, you really, you feel like they are yours and you start thinking about these choices. I think it’s why you see millennials do a lot of like really crazy kind of intense stuff with their kids. It’s cuz our, it’s like if I don’t buy the best stroller, am I showing that I’m the best parent And we wanna win gold stars cuz is there anything more true about a millennial than that? we know we’re gonna get the participation trophy either way, but we’d really like the MVP trophy too. but I got such a blessing. I think I would’ve been more of a Type A mom had I not been raising gild and my girls at twins at the same time. my best friend always says this.

She’s like, what a blessing that you just had all of that all at once. Because I had to do really fast, hard work to think like what matters to me in my motherhood journey and where do I really wanna leave an imprint and be most involved and where am I gonna have to let go a little bit more than a stay-at-home mom might or somebody with one baby instead of twins.

And these choices, All that work immediately paid dividends in my work in separating my identity from Guild. So I really think, parenthood or any journey in your personal life that makes you do that same thing, it can happen in romantic relationships it’s the same process of separating your identity from your parents that most of us do in our teens. All that work really gives a lot of, benefit to not letting your identity be your company either. 

JOE: Do you think it’s something to do with like just having other things that really matter as much or more?

RACHEL: that’s a great question. Yeah. It has to, I couldn’t do it if I’d been in a intramural kickball league or something. That never could have been the thing. it has to be something that you hold in your heart, the way a founder holds their company in their heart. 

JOE: Yeah, it’s, interesting, that I have like two big things that I feel like failed in my life and in both experiences it was from like squeezing the bunny too tight, like wanting and needing it so much that, actually that’s the thing, like needing it. I heard this framework a few weeks ago.

I was reading a book and they were talking about moving from, like needing to wanting, and they were using really simple, trivial examples of like, when you think you need a car, it starts to com like be everything for you. And then when you just like, oh, I just think I want that cool car, it starts to be less important in your world.

But I think that like, that difference between, like, I like to use your example of like, I need guilt to be everything. And then it’s like, oh, it’s so tight and hard to make it work, where it’s like, I want it to be a great company and I want it to make an amazing impact and I want it to do all these things, but I am still whole. Whether or not that happens and like the way you show up is different.

RACHEL: Absolutely. And do you know something interesting? I wanna say this in a really delicate way to not make light of the disparity about what, but I have found in my work with America’s workforce at really all levels, we aim to serve the most marginalized employee and design for them so that we can serve every employee in the workforce.

But that’s our design thesis. I have found that folks who have, Had hard, I’ll just describe harder challenges in life outside of work, often have a more healthy relationship with work. I have found that the,I’ll pick on the environments I grew up in. The folks who are in elite higher ed institutions for college, places like Stanford, folks who are earning MBAs in the, kind of, I’ll call it gold star accumulating 20 something life.

frankly, a lot of us had an enormous amount of privilege and of course we had difficulties, but nothing like growing up in very often not growing up in poverty, very often, not having the same sort of difficulties that, I see more commonly on the frontline workforce.

And, there’s a danger for when nothing has been hard. You feel like you need work or these other kind of manufactured difficulties more and you cling to them more. and I’ve always been quite impressed That on average the frontline workers we work with, they often have their priorities a little more straight. And that freedom actually lets them explore what they want in a different way about work.

JOE: the question of what you want is like one that I wrestle with a lot. you know how to answer it?

RACHEL: No, this is a good, now you’re gonna have me puzzled on this one for a while. 

JOE: I think your point is really well taken. it is the ultimate of first world problems, but the world feels to those of us who, and I grew up with an incredible amount of privilege. wasn’t like rolling around in mansions and Rolls, rolls Royces, but like I didn’t want for anything. And I’ve always felt like the world is sort of an oyster that is there for. Exploring and it in a way is like almost overbearing pressure to make sure that you explore it really well.

RACHEL: yes. It’s like if the only thing I haven’t accomplished yet, or the only part of my Maslow’s hierarchy that is left for me to navigate is this self-actualization and the avenue. I’m asked to do that in current modern society is through work. That’s a really tricky thing to do. 

JOE: Yeah. How much of a difference do you see with your, like, frontline workers versus like, what is used the MBAs as a title to use the group? do you see that, like do you see a difference in the way that one group thinks? I have to find that through work and one group maybe finds that through other channels. Cause I think everybody’s searching for that.

RACHEL: Yeah. I’ll put it this way, I think, maybe not in every generation, but certainly in the two or three most recent privilege can be an, non-productive buffer for failure. if you won all the, got all the participation trophies, won some others along the way. Got into the elite college, got the hot job, went to the hot grad school, You’ve been trained to ignore all the failures cuz you keep them off the application and you keep them off the resume and they’re not in your letters.

It’s all about, all the things you’ve accomplished becomes your identity. and you see that in elite higher ed, in a way that really bothers me, because failure is the great teacher, right? Whereas in the frontline workforce, when you talk, it’s so fascinating to hear Bri Brown actually talk about this in one of our conversations.

But, 85% of Americans can point to a moment of educational shame. And we know that moments when they often stop giving up on themselves as a learner, which is a horrible thing we all wanna fix. The flip side of that is that the folks who then persevere and go find that mentor who believes in them, find the class that they feel successful, et cetera.

Overcoming those failures in your earlier years makes you such a more self-actualized adult. And I think there’s a real, difference and it’s, I won’t say it’s perfectly causal, but a lot of correlation between privilege and that protection from failure, that’s really problematic cuz you, it shouldn’t be 30 before you’ve had your first face down in the arena moment.

Right. and so I, I do see so much resilience in the frontline workforce that I think is distinct from, and it’s, these are all generalizations. So, It’s, not to say there aren’t wildly resilient MBAs either, but I think as one I can pick on them, but there’s so much resilience in the frontline workforce, and we think all the time about how to harness that resilience. 

JOE: it’s really interesting. I was actually listening to that conversation with Brene Brown today as a matter of fact, and, remembered that 85% comment. And I, so immediately of course, I start racking my brain and I’m like, did that ever happen to me? Like, I’m going through it and I different and not really, but I think the reason it never really happened to me is that it happened when I was in kindergarten. so now I like love books like Voraciously love books and really have liked to read for as long as I can remember. But when I started school, I was in the lowest tier of reading capabilities and I’m the youngest of four. Both my older sisters are like very specialized doctors. My brother has higher IQ than both of them.

it’s like weird. I like. I graduated, like whatever the highest thing in college is summa cum laude, something. And I feel like the black sheep academically in my family. And I remember that moment I was like, oh my gosh, I’m not good at this. Like, oh, so, but my mom was a teacher and she was like, eh, we’ll get you good at reading. And by the end of that year, I was in the top tier of reading and that, like, I hadn’t thought about it ever before. Literally listening to your episode with Brene Brown and thinking to myself about, Oh, like I learned very, very quickly early that like when you are bad at something or you fail at something, it’s just a chance to get better at it. So 

RACHEL: That’s amazing to learn that at five. That 

JOE: I’d never like it until you had put doing the show. I’d never identified that. I was like, why does that always, and it’s one of these things very fascinating. Cause it is. It’s a huge gift.

RACHEL: Wow. That’s unbelievable. And you know,I don’t remember if we talked about it in the show, but just to zoom it out, 56% of folks in the United States read, above the age of 17, read below a sixth grade reading level. 

JOE: Really 

RACHEL: Right? 

JOE: is that because they stopped reading, or why is

RACHEL: whole variety of issues. we are country of immigrants and we don’t do a great job always providing resources for folks who came here with a second language. So the, that I would say is a huge category, and those folks tend to be working on it. Just where they are today is like my Spanish would score way below that? but then a huge percentage are folks who were mis served in the K12 system. and, you could say, you could make them I, or they statements For me, I tend to think about them as systemic statements.

in, in most cases it’s the system. I’ll give you one more beyond K-12. the average community college in the US has a five to 20% graduation rate. That means 80 to 95% dropout. But we label that on each human. We’re like dropout, dropout, dropout. But like, if a system is failing, 89 to 95% of people, Do you call every customer a dropout?

Or at what point do you say like, this is a dropout factory? This is a dropout system, right. Like, I think there’s a lot of systems challenge and I always try to be careful about the language I use. but we gotta fix that. because it, both of course, I’m sure has created tremendous resiliency in those folks who’ve had to overcome those situations. But it’s also not the equitable society we wanna live in. 

JOE: Yeah. you do such an incredible job of looking past, like looking at like, okay, what’s the actual reason? For this, instead of getting lost in the, like the frontline, whether it’s you need to build your company in, in the Bay Area, you’re like, why is that? And is that true that it’s the Bay Area or is it doable somewhere else?

Like, oh, well look at all these people who are dropping out now. They’re dropping out, now they’re dropping. Like, well, is it the person’s fault or is there something happening beyond that we haven’t thought about yet? and it’s a gift. I admit myself, I’m a believer that like most gifts are actually. Somebody working really hard to develop a capability to do something. so I’m curious, like have you always been that way or have, have you always been really good at like looking past the surface and finding the deeper thing? Or is that something that’s been cultivated over time?

RACHEL: that’s a good question. 

JOE: I had a really great experience in, Middle and high school of having great humanities and social sciences teachers. And I think that put this love in me of asking, the five whys or, learning that like cultures have developed in very different ways for very different reasons.

RACHEL: There’s like one human experience, but perhaps the most powerful one that I think is now really well known because of that book, homo Sapiens. But is something that,studying John Locke and the early philosophers in debate class really taught me was the power of telling a story is the uniquely human differentiator.

But all these things that we accept as fact, a lot of ’em are stories. Democracy is fiction. Someone made up the concept of democracy. Justice is an invented concept. It’s not to say I don’t believe in them, I believe deeply in both of those, but those were conceptions. Of a single human and then a group of humans, and then a community, and then a society. And so I try to always look at anything where people say, well, that’s how it’s always been done, or that’s how people do it. I don’t often accept that. but I would attribute it to these really great early teachers I had, 

JOE: Yeah. Oh, I love that. I don’t know if you’ve, if, are you familiar with the concept of category design?

RACHEL: like category creation, the same concept. Yeah. Like play bigger the Yes. Yes. I, oh, I love, I love that Yes. 

JOE: Yes. Because really you just identify democracy is a new category of politics or of societal structure that was invented, forever ago. it’s so fascinating. I hadn’t really thought about it before, but you’re so right. That’s exactly what it is.

RACHEL: Yeah, It’s that concept. and the way Yale writes about it in homo sapiens and anybody,I think that is the most interesting thing about being human. 

JOE: Yeah. does it feel very empowering to you? To me, it feels incredibly empowering.

RACHEL: Yeah. Completely. Yeah. It’s why I feel confident. I would otherwise feel, honestly, I think like, a total imposter with the mission statement and vision we’ve created at Guild every day. If it weren’t for the permission to believe that there’s a way to do things differently, even if we never have. Cuz our belief at Guild is that, talent is equally distributed throughout the world. Opportunity just hasn’t been, and so I’m not, I don’t 100% subscribe to the version of meritocracy that we’ve subscribed to for the last, at least a hundred years in America. I’d argue 400. that, it’s just these people who have and haven’t pulled themselves up by their bootstraps purely based on merit.

I’m pretty convinced that situations matter and yeah. And so that ability to like imagine a new future or imagine creating a dent in a future is, I think the only way you can do entrepreneurship at scale. 

JOE: I wanna leave with that note. The ability to believe in a different future, which is so hard, and to be able to see it is so hard. And, I love what you guys are doing at Guild. I really identify with that as well. I’ve always felt like we tell ourselves people are talented to alleviate the burden on ourselves to be better. Like, that’s the thing that I truly really believe in. Oh, Steph Curry’s just great at shooting basketball. He’s just talented. Like, no, he’s done like a hundred thousand reps. Like if you did a hundred thousand reps, probably be pretty good too, But you won’t do that work. It’s kind of the energy. I do have, I have one more thing, before I let you go, I know that you love books. 

RACHEL: My wife and I have a, our habit at night is to turn into 65 year olds and sit in these two chairs that are our favorite chairs in our house, drink tea and read. that sounds amazing. 

JOE: Yeah, it’s actually quite nice. but I’m curious. Book recs, what do you got? Maybe top five. They could be just your five favorite ones. They could be five that you like recently have been into or that you’re interested 

RACHEL: What a fun question. Okay. Of course, I’m one of those people who keeps lists, so I’m gonna pull up my most recent list of ones I’ve been loving. let’s do this. let’s do top two. Maybe like most impactful. You’re like, oh, I read that and it changed the way I view things. I think I’ve made on one of them, maybe top two for like, let’s go with like, I dunno, business or self-development or something of that nature.

JOE: And then, I don’t know if you’re a fiction person or not, but if there’s like a All right. Favorite category and then title in the category.

RACHEL: Okay. I’ll try and blend and some might overlap. My mind first went to the red tent, which I read in middle school, but have read many times after. And it. get, it isn’t explicitly the Bible from a woman’s perspective, but it is parts of the biblical era written in the voice of women rather than men. And it is one of those experiences where you suddenly get to see a reality from a different angle, right? I didn’t grow up hyper religious, but did grow up as a part of a church and a grandfather, great-grandfather in a church and, kinda only had one view of the Bible and it sh it shook me up in a really powerful way.

so that would be the first, I’ll get to, I’ll come back to see if I can find like my second ever favorite one that comes close, but tips into the self-development and business development. Brene Brown’s gifts of imperfection hit me at a time. the book often meets the reader at the moment you need it.

I had been given that book many, like three years prior to reading it, but I read it in 2019 when I was reckoning with my both perfectionist habits, but also just who I wanted to be as a leader. I was getting a lot of tough feedback at work. I was reconstructing that from that girl boss blazer to that cardigan wearing founder, ceo and it, that book hit me deeply.

I read it at the same time as two girlfriends on a kind of mom’s weekend where we were all trying to refresh and plan for the year ahead. And it really, it was powerful. okay, now we’ll go to more fiction and other kind of broader, I’m, girling my list cuz this is so fun for me. I hope we’re not in a rush cuz I’m just having like the best time. Viktor Frankl and, Edith Eger, it’d be hard not to mention their books. they’re both Holocaust survivors. I. think the flip side of my belief that, most of the things we believe like democracy and justice are created by humans. the Holocaust was also an idea. 

JOE: man. Search for Meaning with Victor 

RACHEL: may, may, yes, but I also love his other book. And then Edith Iger wrote The Gift and The Choice, and they’re very, they’re sort of all complimentary together. though they would be very hard to read back to back to back to back cuz they’re emotionally exhausting memoirs of their journeys.

but, studying the Holocaust has always been a really,I don’t know, call it, interest of mine. I, it’s my favorite museum in the United States and the books that I think I’ve learned the most from, but they’re also both books about yourself, like the Edith Iger is The Gift Is really about, how to reframe your own mindset and how she did that as a survivor, obviously, Victor Frankl’s book.

Same. So I would put those four as kind of a category, but they’re all really a mix of history and thinking differently. okay. That was fun. I’m scrolling through seeing which other ones I wanna highlight. Best book I read last year was Body Keeps Score. it’s about, well, so, gosh, I’m gonna seem like I have dark reading habits.

I swear I read lots of fun fiction, but it’s, based on the study of trauma. But about how our bodies carry both. it touches on the ideas of? intergenerational trauma and how trauma can be passed down, but also how our individual stress choices are, very related to our physical health and kind of the whole body system, and how our body absorbs stress, trauma, happiness, joy, et cetera. the reason it’s heavy is a lot of the research in this space has been on truly devastating trauma victims, often ptsd, child abuse, et cetera. But the insights from the book are about? lowercase T trauma. and about how you can better understand your body and your relationship with stress and other microtraumas.

And so that book really rocked my world. I’d never read anything like it. there’s a great book by, Oprah and I, a gentleman who I thinks last name is Perry, that gets similar to that, that I read afterwards and loved. And so I’ve been very interested in learning about how we all handle stress. and then let me pick one more.

Well, I said homo sapiens earlier. I mean, That is just one of the best books of all time and I’ve given that book I give books every year for Christmas, to both the guild team and then to a lot of my, friends and family and that’s one of my favorite to give. So, how’d I do,

JOE: one has. Oh, it sounds amazing. that one, actually, homo Sapiens is the one that has been on my, like it was on my list and then I didn’t get it, and about it. You know what I mean? So it’s, now it’s on, I’m about to order it cuz it’s, It has to be done. I just finished a book and it’s like, all right, I gotta do another one. Like, gotta 

RACHEL: Oh, it, I’ve reread it a couple times. It never ceases to amaze me what that book, where it sends my brain. Cuz it’s one. of those, you read it at night and then it pops up in your day as you think 

JOE: Yeah. Yeah. You let your subconscious sit there and stew on it. Have you read any Richard Rohr? 


JOE: Okay, 

RACHEL: Oh, book rec. That’s my love language. you. just, ugh. Okay. Thank you. 

JOE: I got you. Oh, I got you. There’s a couple that, especially if,I’ll ask this delicately. I don’t want it to come off as, critiquing if somebody is, but are you a, are you an Enneagram like Deep Diver or are you like, I take a quiz and I read what it tells me about myself.

RACHEL: deep diver. I’m nearing the completion of a conscious leadership coaching training that’s rooted in Enneagram and conscious leadership. So I’m, show me the bottom of the pool and I’ll head down there. 

JOE: I’ve got some stuff that might actually not be deep enough, but there’s some Richard Ro stuff. That would be All right. Cool. there’s that, and then there’s one other one that, I grew up in the Catholic church, and it was, I’m very good at just showing up and checking boxes. So it was two like, oh, I can show up and like, take communion and then forget about this for a week and then come back. So my journey in spirituality is a little bit like undefined in the moment, but Richard Rohr has a book called The Universal Christ, which is one of the more,reinvigorating and also like, it made me look at the world in a very different way. Like immediately upon reading it like, oh, these things that I have felt for a very long time have. Like backing to them, which was 

RACHEL: I can’t wait. Cuz I think, if you believe in the diversity of things that humans have invented in stories, there’s something so interesting and puzzling about the concept of a God or a Christ that nearly every culture has found. And that makes me constantly curious, right? because There are so many other choices where cultures have gone left, right, center, upwards, downwards, different, and then there are these common threads of the human experience and religion or spirituality is, one. That’s so fascinating.

JOE: There is,I wanna let you go cause I know we’re a little bit of past time, but there is a, have you heard of the Dow Jing? I think I might be not pronouncing that correctly. It’s a Eastern, eastern text. And, people say I haven’t read it, but people say that it has almost the exact same. Messages, stories, everything is the Bible  sands like Jesus, right? so it’s like, even that, which is not like a formalized world religion necessarily is like a thing that mirrors the same story. And so every time I hear things like that I’m like, yeah, there’s something that is so true to who we are that we, that everybody seems to discover. Every 

RACHEL: Yeah, 

JOE: to discover. It’s just fascinating to me. 

RACHEL: the best way I’ve ever heard it described by a leader, I, I don’t identify as one particular religion, but go to a church that identifies as, multidimensional and, multi-denominational, but they’re, the way they describe it is many paths to God. Colon, semicolon mean God is love.

Like simply like they’re like when you pull the roots out of any of these, you know what was best intended in any of these ancient texts, in any of these spiritual traditions. So, that always 

JOE: That’s awesome. I could have a whole other conversation just about that. next time. Yeah. Rachel, tha thanks so much. I really appreciate your just like, willingness to share and talk about deeper things and, 

RACHEL: Oh, this is wonderful. Thanks so much for having me and for letting me have such an authentic and deep conversation. 

REID: Okay, Joe, so Rachel Romer, who we knew there was a lot of places that we could go walking into that conversation and had some. Perhaps like assumptions just based on the vastness of her experience and the accomplishment around like some errors that be, might be interesting to pull from. so I’m curious now looking back on the conversation, did you go where you thought you did? What were some of the main takeaways for you from your chat with Rachel?

JOE: Yeah, we went in some of the directions that we talked about beforehand. some just weren’t natural to bring up, so we didn’t go to all of them. But, It was interesting. we talked about her intuition and how she like got the courage to do the things that were like opposed to the people ahead of her. one of the places the conversation went was she had her board telling her, you can’t build a company outside of Silicon Valley, but she knew she could.

And what is the. Bravery to go beyond, like basically rebel against what authority is telling you to do. we talked about the Enneagram a little bit and she talked about how she identifies as an Enneagram three That is particularly difficult for threes who want to be seen as successful and need other people to think they are successful.

And so doing something that is counter to being successful is really weird. And so just, we talked about like that process and it was very interesting just to hear how she does that. And she’s, she said, I’ve come from a line of people who are entrepreneurial and kind of think a little different, and I think that gives me a little bit of confidence to do it, which was an interesting point. but honestly, man, more than anything else, my takeaway with her is just like her emotional availability the way she makes you comfortable in the room was like, An incredible lesson.

REID: Mm-hmm.

JOE: Because here you have somebody whose list of accomplishments is like really big and her own, she could have a really high degree of self-importance and it would be merited. But you feel like you’re talking to somebody who’s just a peer when you talk to her. And hypothesized that her success has far more to do with that people to people relational ability. I. Then it does any like tactic that you use when making a decision. It’s like you get the vibe that she’s there, she’s present, you’re important for her, and that makes you really like, want to work with her.

Like you just feel like this is great. Mm-hmm. And when she talks about a lot of her role as a CEO is to, build partnerships with universities and platforms and all these things, her ability to emotionally connect in that way, so, Is huge for doing that part of the role. So it, that was a huge takeaway.

REID: It makes me think of, a. A piece from Simon Sinek that was shared with me recently around what good leadership looks like and that one of the important pieces of that puzzle is authentically and genuinely caring about the opinions, feelings, whatever of the people that you’re around.

So if you think about the context of you having a conversation with Rachel, there’s a world where you speak with somebody who has achieved great things, and you can tell that when they ask questions or whatever they’re. Doing it for you for the sake of the content you’re creating or whatever that is, versus what it feels like you got from Rachel, which was an actual genuine openness.

Yeah. That was not a like position as a leader, need to show up this way, but it was authentically the way that she goes about interacting with different people, making decisions, participating in the things that she participates in.

JOE: Well, I think we take, sometimes we take these like concepts, leadership, right? And we extrapolate them into tactics and techniques and things. And the reality is like it, it could be a good person. Which is way too abstract and way too, like what does be a good person mean?

REID: That’s why you get to the tools of like, how do you make that tangible, tactical. Yeah. But yes.

JOE: But yeah, like she just is a good person and it comes through and you don’t feel any sense of inauthenticity. You feel like this is just who she is? which was like a lesson in leadership by simple example. Which was a huge takeaway.

REID: I think there might also be a piece that’s related but not the same around vulnerability. We’ve had a lot of discussion recently around vulnerability, and I actually am going to not do, I’m going to do a disservice to where this originally came from.

It might have been on scared, confident with Tiffany, but this idea that. You must lead with vulnerability and the vulnerability that you express sort of sets the ceiling for the conversation. And so when she comes in and you have the experience of her that you do, and that vulnerability, that sort of feels like it came through in that conversation as well, that is also a key to quote successful leadership, but that it allows you to have a much more thoughtful conversation with. Whether it’s making a podcast or leadership decisions or anything that like that management decisions and conversations, is that leading with vulnerability is the thing that allows that to be 

JOE: well. I’ll give a good example of it. Rachel has had Brene Brown on her show. And she referenced that Brene Brown is like a hero for her in her own life. And for the first time ever on this show, and this probably won’t make the episode, so I’ll share the story right now.

For the first time ever, I just had a complete mind blank on the show. Like I had a question that had come up into my head while she was talking, and then she finished what she was saying and my mind just like lost it. And I was like, I’m sorry, I’ve, I have completely lost the question I just had in my head.

Then I sat there and I expected it to come back cause it normally does. And I was like, yeah, it’s not coming back. I’m really sorry. This is not the best experience for you as I sit here and search for this question I had. And this is the moment of vulnerability. She goes, she kinda laughed. She goes, don’t worry about it.

I had the exact same thing happened to me with Brene Brown, who’s like my hero. And it’s like, oh, you’ve just made this experience I’m having right now. Normal, relatable. You’ve made me not feel self-conscious about it. Normally that sort of thing would happen and I would like beat myself up about it from a performance standpoint for at least the rest of the day, if not like weeks on end and like, yeah, I still wish I hadn’t had that moment of just like complete brain fog, but it didn’t matter and it didn’t mess up the conversation and we just like jumped back in because it wasn’t.

I didn’t sit there and in the back of my mind wonder if she was judging the fact that I didn’t have a question ready. You know what I mean? So that’s like a great example of what you just said of like, leading with vulnerability. Let me show you where I had the same problem. Like let me show you my falling, like my self falling short because everything that gets published about me is 30 under 30 hall of fame and look how great guilt is and like all those things, So it was just like this incredible human side juxtaposed with.

Tactics and clear results that show the human side is also working. which was also interesting to think about from the intuition side. And like she has a clear gut that tells her what to do, but then she’s very data driven and you hear her talk about numbers and rates of dropouts and all these things that they work on, and it’s like she has done a nice job of like really finding balance to support, Both sides, if you will.

REID: Yeah. Some really interesting. It’s like leadership in tangible lessons just from consuming the conversation that there are to carry forward. Awesome. 

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