Chynna Clayton worked in the personal office of Barack and Michelle Obama as their Director of Travel and Event Operations. Her career also includes administrative roles at Disney and the White House where she served as “body woman” to Mrs. Obama during the Obama Administration.
Chynna is the founder of Matriarch Made Development, a consulting firm that helps organizations develop administrative teams.
In this episode, Chynna tells us how she wound up working in the White House with the Obama Administration. Chynna also shares tips on navigating high pressure situations, managing stress and burnout, prioritizing self-care, and more!
Service is the price you pay for the space you occupy.
CONNECT WITH CHYNNA
Empathetic, strategic, and meticulous about the details, Chynna Clayton has built a career enabling some of the world’s most influential leaders to excel in high-stress environments.
Chynna is the founder and CEO of Matriarch Made Development, a consulting firm that helps organizations develop high performing administrative teams and identify and address overall operating structure and events logistics inefficiencies. From helping leaders figure out their onboarding, communication flow, event logistics and how to further develop the talents of their teams, Chynna supports leading organizations in creating a systematic approach to tackling business/events challenges and bottlenecks.
Prior to Matriarch Made, Chynna worked in the personal office of Barack and Michelle Obama as their Director of Travel and Event Operations. Her career also includes administrative roles at Disney and the White House where she served as “body woman” to Mrs. Obama during the Obama Administration.
Chynna graduated from University of Florida with a B.S. in Event Management and Political Science and a minor in Business. She currently resides in Washington, DC with her wife Katina Hoyles.
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Chynna Clayton 0:00
Hello, my name is Chynna Clayton I’m the founder of Matriarch Made Development and my favorite quote is service is the price you pay for the space you occupy.
Podcast Intro 0:08
The Leader Assistant Podcast exists to encourage and challenge assistants to become confident game changing leader assistants.
Jeremy Burrows 0:29
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Chynna Clayton 2:14
Thank you, Jeremy, thank you so much for having me.
Jeremy Burrows 2:17
So you gotta tell me, you know, I know you worked for former First Lady, Mrs. Michelle Obama, and worked in the White House, but you gotta be honest, for just a second tell me was it more fun to work at Disney or the White House.
Chynna Clayton 2:34
It was definitely more exciting to work at the White House than Disney. But, you know, Disney is an amazing company. And you know, they truly are about creating the family friendly atmosphere. And that’s even within their offices, there was very much this team oriented spirit. But you know, just having the variation in your day to day the White House was where it was at.
Jeremy Burrows 2:57
Nice. Makes sense. Makes sense. So okay, let’s learn a little bit about you personally first before we dig into your career. Where do you live? And what’s your favorite thing to do in your city?
Chynna Clayton 3:11
Oh, goodness. So I live in Washington, DC. However, I’m originally from Miami, Florida. So I’m a Florida girl through and through. Although these days, I’m definitely making the distinction between being from Miami not necessarily the state of Florida. My favorite thing to do is try new restaurants with my wife here. Like you know, DC has an amazing food scene that I think a lot of people take for granted. And you know, there’s just always something great popping up.
Jeremy Burrows 3:41
Nice. What’s your favorite type or genre of food these days?
Chynna Clayton 3:45
Oh, my goodness. Um, you know, I’m a big seafood person. And I also love Italian, a good authentic Italian restaurant too.
Jeremy Burrows 3:57
great, actually, I can’t remember the name of the restaurant. But I was in DC in December and went to a pretty fun restaurant there. And the guy I was with was telling me all about the scene there and seems pretty, pretty lively.
Chynna Clayton 4:13
It is. it is.
Jeremy Burrows 4:15
awesome. Well, what’s, what’s your favorite Movie or Documentary?
Chynna Clayton 4:22
Yeah. So, you know, I actually I really do love documentaries. You know, I like facts. And I like raw information and you know, obviously learning through stories and firsthand accounts. So you know, the idea of like, chronicling experiences and events, it really intrigues me because I feel, you know, the best way to prevent things from reoccurring is to know the history of things, right, especially the wrongs or at least I hope, right? If we’re paying enough attention to our history, we should not be repeating a lot of our mistakes from the past. But my favorite is Slowburn it was on Netflix. And it was about the Watergate scandal, and essentially the series is an adaptation from the first season of the podcast. And it goes beneath the surface with all these, you know, with all this in depth research and footage to uncover things that I personally never knew. And you know, and as I’m watching, I’m like, I wonder if the people who were living through this knew any of these facts or details, and I ended up I watched during COVID. And, you know, I’m sitting there, and I’m thinking, how will everything that we’re experiencing right now be explained, right? So like, how will the documentaries produced 50 years from now recount Trump and the pandemic and all these things that we were, you know, going through in the moment, you know, like, will that generation judge our choices, right, because as I’m watching, I’m low key judging some of the choices that were made back then. But clearly, you know, I had all the facts and access to all the facts right in front of me. So it was a little easier to cast that kind of judgment. But, you know, I’m just curious. I’m like, How will people perceive what we are going through now and the decisions that we made and about dealing with it, you know?
Jeremy Burrows 6:04
Yeah, very, very fascinating. And, you know, speaking of Netflix, and political documentaries, or even shows, you know, I have to ask, Have you have you watched the show House of Cards?
Chynna Clayton 6:20
Jeremy Burrows 6:23
Is there any is there, okay, so I gotta tell you funny, funny story. So I interviewed someone who works in the Premier League in English football, soccer. And I asked, I had her on the podcast, and I asked her if Ted Lasso was any, you know, was it at all like working in the Premier League? And she’s like, what’s Ted Lasso?
Chynna Clayton 6:50
Oh, my God.
Jeremy Burrows 6:51
And I was like, Okay, so I’m gonna have to delete this out of the interview, because she hasn’t even seen the show. Well, fast forward two years, she’s like, Hey, I just watched the show. And I know what you’re talking about now? And yes, it’s just like working in the Premier League.
Chynna Clayton 7:04
Oh, my goodness.
Jeremy Burrows 7:05
So anyway, I had to ask you is House of Cards at all, like working in politics, in DC, in the White House?
Chynna Clayton 7:12
You know no, like, it definitely takes it to an extreme level, I, you know, there are certain things as we’re watching, it’s just like, they’d never do that, or Secret Service would never act that way. Or, you know, like all the things and all the protocols. But yeah, it’s it was quite entertaining. If I might say.
Jeremy Burrows 7:33
Yes. Well, when I was in DC, I was walking around, you know, walking around the monuments and everything. And I just kept playing the House of Cards theme song in my head, like, as I’m walking around DC, so anyway,
Chynna Clayton 7:45
oh, my gosh, I thought you were gonna ask if it was anything like scandal?
Jeremy Burrows 7:49
Oh, I actually haven’t watched that show.
Chynna Clayton 7:53
Oh, really? Okay. Okay. Fair.
Jeremy Burrows 7:56
All right. So one more personal question, if you could have one gigantic billboard, anywhere, maybe times square or wherever, with anything on it, what would that billboard say?
Chynna Clayton 8:11
Well, um, I think I’d say something simple, like, you know, leading with kindness will get you so much further. And I know that sounds cliche, right. But it is truly my mantra, like, being kind and empathetic, even when it’s challenging to do so. Right. Even when someone has wronged you beyond belief. It’s just how I live my life. Right? It’s, I know that there is favor and being kind to people, because I feel like I’m an example of it. You know, it obviously involves having a forgiving spirit and trying not to take things too, personally. And that can be tough. But I challenge more people to try and do it and start practicing it. Because there’s no reason not to. Right, right?
Jeremy Burrows 8:59
Yeah, that’s great. We’ll get the billboard set up now. All right. Well, the probably the most common question you get asked, and I’m sure my listeners are curious, so I’ve got to ask it. How did you end up working with Michelle Obama?
Chynna Clayton 9:17
Yes, yes, yes. So it all started with an internship, right. So I attended the University of Florida, where I received the dual degree and event management and political science and a minor in business. And back then, you know, it was my hope to start my own event planning company in Atlanta after school, and then maybe later down the road run for office somewhere, you know, or locally in Miami. And as a graduation requirement for the event management degree, I had to complete this internship in my field. So I applied to a few internship programs in Atlanta. And then my college advisor mentioned this White House Internship Program. She’s just like we had a student who applied under the Bush administration, I think, you know, you should definitely look into it. And so I did, I applied and I was accepted, not only to the White House Internship Program, but with the program with the Atlanta Hawks planning events for them. And I almost passed up the White House internship opportunity, just because it didn’t fit into my plan, which was to end up in Atlanta after graduation. Right. But you know, thank God for my mom and talking some sense into me, and she was just kind of like, why would you ever pass this up? You know, first African American administration, you have family and Maryland that you can stay with, so you won’t be alone. And obviously, that’s, you know, you can live rent free, single mom thinking, you know, cost effectively as well. And so I was just like, Okay, fine, right. So I accept this internship. And I was an intern in the Office of Presidential scheduling and advance. And I knew what scheduling was, but I had no idea what advance was. I just knew that on the website, it had some mention of events. And so you know, turns out advance was these the event planning and logistics arm of the White House. So when the President, the First Lady, Vice President, or then the second lady, would travel beyond the White House, White House gates, there was a team of people who would go out and coordinate all of the logistics involved in that. And so I went on the road doing advance for about three years, and got to see much of the world as a result, like prior to that, I’d never done any extensive travel, I’d never done any real international travel aside from like Jamaica for spring break. And after being on the road for three years, and then worked on the reelection campaign, the Presidential Inaugural Committee, and it was over that course of time that Mrs. Obama says she took notice of me. And I handle a lot of their hotel logistics in those roles. Or Ron logistics, which stands for remain overnight. So anytime that they, you know, stayed somewhere outside of the White House, there was somebody who was coordinating with the hotel, Secret Service, military agencies to get all the ducks in a row. So being in those spaces, you know, she’s really taken notice. And, you know, after the inauguration, I actually, that’s when I did my two years stint at the Walt Disney Company supporting to their senior vice presidents, but I was still kind of going on the road in my off time and taking on trips. And shortly thereafter, I got a call to, you know, to become the first lady’s body person and essentially her right hand. Yeah, yeah. All from an internship.
Jeremy Burrows 12:48
I love it. I love it. And, you know, all from your mom’s nudge, right?
Chynna Clayton 12:53
Yes, absolutely. Could you imagine I’m like, oh, man, life would have been completely different.
Jeremy Burrows 12:59
Wow. So yeah. So you said you got a call? Like, was that just from someone in the office that said, yeah, we want to
Chynna Clayton 13:06
Yeah, it was the chief of staff in the office.
Jeremy Burrows 13:09
Chynna Clayton 13:10
Well, actually deputy chief of staff in the office. Yeah.
Jeremy Burrows 13:13
Great. So you then supported the family or specifically her? You said.
Chynna Clayton 13:22
Yep. So specifically, Mrs. Obama. But with that came, you know, obviously, supporting the girls as well. But yeah, yeah.
Jeremy Burrows 13:32
Cool. So what was the funniest thing to happen to during your time working with, with them with the Obama family?
Chynna Clayton 13:40
You know, so the funniest thing is, well, this is what I’ll say, I almost didn’t accept the job. Yeah, crazy, right? Initially, you know, I was just unsure if I wanted to accept the position because, again, Disney was this amazing company. And, you know, I just got accepted to a master’s program for hospitality that Disney was going to contribute towards. And, you know, even with the White House on my resume, it had taken a while to like, really settle into a career that I was excited about. And I’ve always been about stability, right? So I knew that this position at the White House would come with an expiration date at some point. And I’d be you know, searching for a job again. So I really was I was kind of hesitant about leaving, you know, what I knew to be my norm and rocking the boat and taking that risk. But again, mom comes in and she’s just like, Are you kidding me? opportunity of a lifetime, right? Like this is history in the making, like why would you not want to be a part of that? And she’s just like, I don’t want you to allow this fear of, you know, finding a job afterwards to get in the way of you actualizing dreams, right? Like she’s just like, take a risk do so. something unfamiliar. You know, at the end of the day, you’ll there’ll be something for you to fall back on. Like, don’t think that way. So, you know, I gotta thank God for my mom, because, you know, not everybody has that kind of support. Somebody that’s supporting you to dream and somebody’s that that’s behind you, you know, in providing a safety net, you know, should things not work out? But yeah, yeah.
Jeremy Burrows 15:24
Wow, that’s great. So you don’t have to get into details. But how often did you end up having to jump in and act as or, or even maybe even not even have to jump in but having to be aware of and have knowledge of what was going on with President Obama and coordinating with his assistant and team? In other words, Were there moments when he had to kind of pick up the slack? And help the team out? Or was it like, I have to at least know enough that if I did need to pick up the slack I could? Does that make sense?
Chynna Clayton 16:03
Yep, that definitely makes sense. So, thankfully, it was very much this team atmosphere. And so yes, you did need to know enough that, you know, God forbid something were to happen, you could step in and assist where needed. You know, quite frankly, it was important for me to just have some knowledge of where he was what he was doing at a certain time, just in case Mrs. Obama ever asked, just in case, you know, the kids were checking in about parents where abouts, you know, but for the most part, we would always kind of work in tandem, right. So when they were traveling together, it was just like, you know, a no brainer that if she was just signing something, I’ll hold the Sharpie out, keep it, pass it over to his assistant, so that he could sign next and, you know, big on hand sanitizer, and making sure you know, that we’re utilizing that. And having that at the ready, you know, there are certain things that he didn’t always, his assistant wouldn’t always travel with right. Tissues, and floss and all this stuff that I had in this big flotus bag that I carried around. And so, you know, just being able to assist and help him out in the event that he needed that, or, you know, there were times that he’d be able to grab her purse, from the limo before I could get there, and just really working in tandem and treating it like a team atmosphere. But you know, clearly being aware of how he supported the president. So that in the moments where he needed to step out, or in the moments where, you know, like, again, God forbid, something happened, you could fill the gap. But those moments are far and few between? Honestly, we didn’t have much slack. But ya know, yeah,
Jeremy Burrows 17:50
that’s great. Well, you know, I’ve, I’ve never worked in the White House. So this is this is on a much smaller scale. But I have worked with high profile executives throughout my career. And oftentimes, people around me, will, would or will get close to me in order to get close to my executive, or in order to kind of get some of the inside scoop on what’s going on with my executive. And another way to put it as people would essentially look right through me as if I wasn’t even a person at times. And I’m just curious, obviously, working for a higher profile person. In your role, did you ever interact with people who treated you as less than human because they just wanted to get access to Mrs. Obama? And if so, how did you navigate that? And personally guard yourself worth in those moments?
Chynna Clayton 18:42
And wow. You know, and I’m sorry that you had to experience a lot of that. That sucks. And, you know, honestly, I did not experience that. And I think, partly because Mrs. Obama did a really good job at stating my importance from the beginning, right. So when we, when she was introducing me, to people, or when we were, you know, coming into contact with folks, she was very much like, This is who you need to go through to get to me, and, you know, she is my right hand and just really showing how valuable I was, and I think, in turn, that caused people to understand, you know, my worth, and treat me with respect, and, you know, I’d obviously do the same, right, so like, no matter who you were, if you were the elevator operator or the custodian at one of the schools you’re visiting, or even a celebrity, I acknowledged and I treated you with the same level of kindness and responsiveness and I think that’s kind of what set me apart. You know, you have some people who do let proximity to power go to their heads, right. But for me before and after Mrs. Obama, I’m still Chynna Clayton right, the daughter Doris key, so it’s Just like, you know, don’t get me wrong, right. I’m proud to work for the Obamas all day long, but it wasn’t something that I’d want. I just kind of let my work speak for itself. You know, because I didn’t join their team for my own gain, I felt that I was serving something greater. And she really did do a good job at just enforcing the level of respect that needed to be had with her team.
Jeremy Burrows 20:24
That’s great. Yeah. And, you know, I talked, I talked about this quote from Dorothy Sayers in my book, where she talks about how the community as a whole is better off if we focus on serving the work. In other words, doing good work versus angling for applause. I love that phrase. Yes. Angling for applause. And so sounds like you had a good, solid grounding of, hey, you know what, I’m here to do good work and for work. And I’m not here for applause. Because when you are for applause, and to be honest, in my prior roles, I definitely angled for applause more than I should. And that’s when you are Yeah, probably more vulnerable to these people.
Chynna Clayton 21:07
Yeah, I was gonna say that’s when your feelings can get hurt. Oh, yeah. Yeah.
Jeremy Burrows 21:11
So, great. Well, thanks for sharing.
Chynna Clayton 21:13
Jeremy Burrows 21:14
Okay, so obviously, there, there’s, there’s busy and then there’s high pressure White House busy. What’s your top, you know, one or two tips for navigating high pressure situations?
Chynna Clayton 21:32
Yeah, I think top would be maintaining composure, and thinking quick on your feet, you know, when you’re in an environment where the pressure is high, the best thing you can do is keep a level head and not freak out, you know, that energy is contagious. So I feel that like, if you remain composed and confident it brings a calm, and a reassurance to the situation, right, like, you gotta fight the feeling to react to external pressure, right, I think that that allows you to really think through solutions where necessary and any outcomes. You know, think back to, we had an event in the White House Kitchen Garden one year, and during the Obama administration, the White House started making their own honey on site. So there was a beehive near their kitchen garden. And, you know, this particular day, someone forgot to close the behive the night before. And we found out just a few hours before the event and found ourselves, you know, okay, high pressure situation, and I was the person who had to deliver the news to the First Lady. And I thought to myself, I’m like, if I remain composed, she will, too, right. And so I delivered the news, knowing that there were just certain things that were beyond our control. And that, you know, I could help shape this and deflect tension by trying to remain positive, right, and letting her know, everything that we were doing to ensure the safety of all involved. Unfortunate situation, but here, here’s how we are on top of it. You know, we had medical staff at the ready to respond. And having that few hours before the event helped us to, you know, identify any kids or any participants with bee allergies, right. But can you imagine if I would have freaked out, right, the team in charge of the event would have freaked, the person who’s responsible for the hive, you know, would have been even more terrified. But I think, you know, my ability to remain calm really helped us focus in on the solution.
Jeremy Burrows 23:30
Yeah, and, you know, kind of what you said about responding instead of reacting? is great, great way to look at it. So, what about self care? So, how do you how have you managed stress and resisted burnout throughout your career?
Chynna Clayton 23:50
Yeah, you know, I’ve found that there’s like, no secret sauce to this, right. It’s a struggle, and it is something that you really have to be intentional about. And that’s easier said than done, especially in our line of work. You know, as an assistant, you are at the mercy of someone else’s schedule, right. And you are constantly putting someone else’s needs before your own. But you have to remember, you’re no good to yourself or anyone else if you’re running on E, right. So you need to take the time to reset and recharge. There’s this, this book by Erica Keswin and she asked, you know, what do you do in your life that makes you feel most like you? And once you know that answer, that’s what you should always make time for on your schedule. Right? That is what goes first. And so I think, you know, if you schedule yourself by saying, from this time to this time, I’m going to focus my attention on work, but after 730 Or come this weekend, I’m not doing anything work related, right. I’m going to take some me time, I’m going to enjoy my family. I’m going to go out to dinner. I’m just going to sit don’t have that glass of wine and watch a movie, whatever it is, but just try to be consistent about it. For me, during the White House, that was much harder, I really did not find that balance. But post White House when the stakes weren’t as high, I was able to carve out time in the mornings or on the weekends. And, and being sure to communicate that to my boss, right? So that she knows, hey, this weekend, I’m gonna go on a walk. So I may not be responsive from this time to this time. Or, you know, in the mornings, check my incoming. And if there was anything that didn’t need an immediate response, you know, I’d go make my cup of tea, sit down, have a little moment for prayer, you know, and just take my time, because technically, the clock starts at nine, right, not 6am. But I think that’s the thing, right, especially with my generation, for sure, we have problems prioritizing, because I think there’s this guilt that comes with delayed responses, right? We think that most people want everything immediately. And I’m sure that there are people who do, but there are also folks who are just like, as long as you get back to me, I’m not expecting a response within two minutes of hitting send. So I think, you know, we’re kind of horrible at setting these boundaries. But what I’m finding is, Gen Z is like in their boundary setting era, right? It’s as if they took heed to our lack of in that area. And they’re just like, they won’t be us. But, you know, there’s also a balance to these boundaries as well, right? Because you don’t ever want to set so many that you jeopardize the functioning of the team as a whole, right? Because right now, you’re only looking out for self and setting so many boundaries of just, you know, to preserve self. And that’s really no way to be right you do want to account for the team in your boundary setting. But, you know, again, I would just say, Don’t let a day go by where you haven’t somehow carved out a little time for yourself. It may not be much, but you do need time to just clear your mind and, you know, have thoughts and dreams that aren’t centered around work.
Jeremy Burrows 27:15
Well said, Well, Chynna, if a brand new assistant, came up to you tomorrow, or give you a call or shot you an email and asked, you know, hey, I’m starting my first week ever, as an Assistant, do you have any tips for me? How would you respond?
Chynna Clayton 27:36
I think I’d say remember that this is all new, right? And it is going to take time to adjust to the new work environment to you know, your colleagues to your boss, or the executive or principal who you’re supporting. You have to give yourself grace and accept the fact that you will make mistakes, right? But you have to learn from them. Right and then bow to yourself to never make those mistakes. Again, you’re human. You’re not perfect. So we are going to make mistakes. But the key is just not repeating the same mistakes over and over and over.
Jeremy Burrows 28:25
Yeah, that’s great. So okay, so tell us about Matriarch Made Development. Why did you start it? And what’s your what’s your mission?
Chynna Clayton 28:36
Yeah. Um, so I started it, because I just felt that our roles are so much more elastic than the word assistant even encompasses. And it was shocking to me that assistants are considered entry level positions, right? When there’s no real training for it, there’s no schooling dedicated to our line of work, and you get in and It’s sink or swim. And a lot of people, you know, they credited to, oh, you know, it was a mismatch. You know, I hear a lot of executives, just saying, oh, that’s just not the right fit. And sometimes we just aren’t communicating our expectations, right, we just aren’t taking the time to, to communicate what we need. And a lot of people don’t know what they need from their assistants. So, you know, my whole thing is trying to work to design a program to correct that, right. I want assistants to stop seeing themselves as just assistants because we are so much more. And when we do our jobs well, the people that we support can perform at their best, right like we we take part in that success. So my hope is just to change the narrative not only on how we as assistants and admin staff view ourselves, but also how the outside world views us. You know, I eventually want to create a platform where we can build community and create a network for assistants, a place where we can share lessons, find resources, and, you know, build upon our skill set.
Jeremy Burrows 30:09
That’s great. So how, how can like, so you work with executives and their assistants together? Do you work with them separately? You kind of anything and everything? How do you practically work with him?
Chynna Clayton 30:23
Yep. So I work with executives and their assistants together, and then assistants, more of a one on one or group session, sort of training. You know, what I tell executives is just like, I’m in the business of changing your life for the better, right and knowing, you know, you can walk around knowing that everything’s under control, and have this trust in your assistant and the schedules that they’re putting together and the information that they’re gathering for you, you know, you won’t have to worry about the ball being dropped or stress about travel and the changes that are occurring while you’re on travel. You know, making sure your preferences are accounted for, you know, gaining back some time in your day. And all that can happen by you investing in your assistant through training. And then for the assistants, it’s more of like, you know, sharing of best practices and tools, things that worked well for me, you know, being a listening ear and helping navigate through some of the complications that come with the job.
Jeremy Burrows 31:24
That’s great. So what would you say, you know, from your experience as an assistant and working with other executives and assistants, and trying to help that partnership? How would you answer the question, what makes an assistant a leader?
Chynna Clayton 31:41
Wow. Yeah. I think the key to being a leader in that role is knowing how your operation runs, right? Knowing who the players are, and how to keep the ball moving. You know, being a valuable asset, right, not only to the person that you support, but to the team to the overall team. You know, I felt like assistants really do know the inner workings of things, right. We know how to get things done. We know the best ways to present information to our principals. The questions to take into account before you go into a meeting with the boss and just using that knowledge to support the team, right offering your guidance. You know, I often say that like the next executives are sitting just outside the boss’s door.
Jeremy Burrows 32:33
That’s great. I like that. Cool. Well, where can people reach out and learn more about Matriarch Made Development and connect with you?
Chynna Clayton 32:43
Yeah, so that would be at chynnaclayton.com
Jeremy Burrows 32:54
Great and I will put your link in the show notes for sure. So people can reach out and say hi and find out more. The show notes are at leaderassistant.com/222. Chynna thank you so much for your time. Thank you so much for your stories and wisdom and passion for the assistant community as a whole. And yeah, best of luck to you.
Chynna Clayton 33:19
Absolutely. Thank you so much for having me and please keep doing what you’re doing.
Jeremy Burrows 33:24
Unknown Speaker 33:35
Please love you on Apple podcasts.
Unknown Speaker 33:37