570 Natalie Siston:

What can growing up in a small town of only 600 people teach you about entrepreneurship? Turns … out, quite a lot: A strong work ethic for one; the value of trusted connection and community another.


I’m Melinda Wittstock and today on Wings of Inspired Business we meet an inspiring entrepreneur who has journeyed from Republic Ohio, on to Silicon Valley, through Fortune 500 corporate, to entrepreneurship.

Natalie Siston is now CEO and founder of Small Town Leadership, where she leverages these lessons to help leaders and organizations create big success in the world.
Natalie will be here in a moment, first…

In a small town, each person’s work matters, everyone feels cared for, and collaboration is necessary to survive and thrive. Entrepreneur Natalie Siston learned these lessons growing up in a town of 600, and if you are seeking a fresh way to look at your company and your leadership style, Natalie says, think of it as a small town. Everyone plays an important role, working with what you have is the norm, and a culture of caring is expected.

With Small Town Leadership, Natalie applies her 20+ years of coaching, developing leaders, and strengthening teams in the non-profit, higher education, entrepreneurial and corporate sectors. She works with both 1:1 and small group coaching clients to help them be more connected – to themselves, their work, families and communities. A frequent speaker, Natalie’s work has been featured on Thrive Global, and she’s also the author of “Let Her Out”.

Today we’re going to talk about leadership, and how to build trust, accountability and community in your team…by leveraging Natalie’s small town blueprint – plus what it takes to write a book, and why Natalie quit her high paid corporate job in the middle of a Pandemic to launch her business.

Let’s put on our wings with the inspiring Natalie Siston.

Melinda Wittstock:         Natalie, welcome to Wings.

Natalie Siston:                  I’m glad to be here.

Melinda Wittstock:         I’m excited to have you too. You went from living in a small town of only 600 people, and you learned a lot about leadership and management that you’ve taken with you right through your career, into what you’re doing now at Small Town Leadership. Tell me what was it that you learned in your small town of 600 people?

Natalie Siston:                  I learned what I think are the key lessons that we forget about in so many of our complex business frameworks and the next hot thing and the top lessons I learned growing up in this town of 600 people first and foremost was work ethic. I’ve interviewed dozens of others as I call them small town, alumni, people who grew up in very similar, micro towns, almost many times they don’t even make a town, there called a village. And I asked all these people that same question, “What was the one thing you took from your small town upbringing that’s made you successful?” And we all have the same answer and it’s work ethic. It’s watching our parents work a nine to five job and then also maybe work a family business or the family farm and the ability to roll up sleeves and get things done and not be concerned with whose role and responsibility and where on the RACI chart does that fall? But instead just, I know it’s the right thing to do. So I’m going to hop in and do it.

So work ethic, hands down, number one and the second most important theme that I learned growing up in a small town that is carried across all of my work is the idea of connection and community. I feel like we’re obviously living in a world where we can connect and communicate with almost anybody at any time, in any forum, but what are we actually really communicating and connecting? And in a small town, you have no choice but to be living your truth, because people can see right through the lies or the BS that you might be feeding them.

And so I’ve always stepped into the world wanting to go deeper with people, wanting to make that really true connection, getting below the surface. And that’s a cornerstone of the work I do in leadership development and coaching is to really help people find that authentic connection with other people and what might be getting in the way from themselves from doing that. It’s the only way I know Melinda, but it’s something that I just love to teach because I think it could change our world if we all stepped forward in a more connected manner.

Melinda Wittstock:         Yeah. This duality or disconnect between having more tools to connect us and more information than ever before, but looking around at our society, it’s like there are two different parallel universes. I mean, there’s kind of like earth one and earth two, just in the political polarity and then there’s so many others besides, so it’s almost like all the communication is getting in the way of the communication, so…

Natalie Siston:                  Yes, exactly, I love how you put that, it’s so spot on. Yes there’s, it’s the paradox of choice. It’s the Cheesecake Factory is this big restaurant with this 12 or 14 page menu, and you go in there and you’re overwhelmed. You’re almost not hungry anymore because you’re like, “Oh my gosh, there’s too many things on the menu.” Same thing with communication, it’s like, I’m so overwhelmed and I don’t know who’s being fake and who’s being real and who I can trust and who’s being authentic and it makes it so, so hard to want to make the choice for yourself about how you even show up.

Melinda Wittstock:         Yeah, really good communication, presupposes there’s trust because if there’s no trust, you don’t really hear, what the other person is saying. Or if we’re attached to our own beliefs so much in rigidity, it’s very difficult to actually see somebody else or even celebrate them being different from you.

So Natalie, when you’re coaching people on that communication and team building and team leadership, which is one of the most vital aspects of entrepreneurship, getting a team aligned on a mission and getting everybody working at their highest ability, what do you advise?

Natalie Siston:                  I do advise them to step back and look at where there is trust and is not trust to connect it exactly to your last point, because you’re exactly right without trust, we can’t go any further. And there are some great frameworks about the trust equation that I use and one is you have to examine the four elements that build trust. You have to look at reliability, do I do what I say I’m going to do? My credibility, do I know what I’m saying? My other’s orientation, do I care about what other people, how they’re showing up? And then your level of professional intimacy, are you willing to go that layer deeper, like we just talked about? And all of these things are multipliers on one another, so if any of those are zero or negative, the entire equation is zero or negative.

And so it’s really key when I’m working with teams to say, “Okay, if you feel like something is broken or missing, look at each of those four elements and identify for yourself where maybe you’re deficient, where might you be getting those zeros or negative numbers” and then flip it and look at the relationship you’re in and examine where you might feel the deficiency with the other person and how can you work together to help close that gap? And I think oftentimes people just have to label it and see it and say, “You know what? It’s because that person never gets their stuff done on time.” I always have to remind them and I would have much greater trust with you if I didn’t have to send you so many reminders. And it’s that simple conversation between people that that might not happen, but if you’re looking at an equation and you Say it’s really that reliability thing that’s getting in our way then excellent. We’re one step closer.

Melinda Wittstock:         So much of it is understanding and being present or aware of seeing things through other people’s eyes, that requires empathy. Here’s the thing is as women, I think we’re more developed in that way, as we add teams, sometimes we can over correct in that, put everyone else’s needs so much more ahead of our own that we neglect ourselves. How to get that balance right? Between really hearing and listening and being empathetic and also being able to stand in your own power, I guess, as well?

Natalie Siston:                  It’s like, “Hello, have you read the back of my book description?” You pretty much just nailed it without us even really talking about that.

Melinda Wittstock:         That’s hilarious.

Natalie Siston:                  Yeah, I mean, that’s exactly the premise of the book that I just released called Let Her Out, Reclaim Who You’ve Always Been. I mean, quite literally for everything you just said, because I found myself, so this book is where life story meets life coaching, but it’s because I found myself saying yes to everybody else and no to myself. I found myself standing at the kitchen at the end of a long Workday being talked at by three different people, wanting another piece of me and throwing your hands in the air and going, “I give up, like, I can’t listen to all of this chatter for one more minute, I just need a minute to myself.” And stepping back and realizing that the ultimate reason that stuff was happening is that, I personally am in the context of this book is we stopped connecting to her.

And the, her, that I’m talking about is that eight-year-old girl, that ten-year-old girl, who was confident and spunky and silly and wouldn’t take no for an answer. And she just gets beat up as she gets older and the more I looked into my past through diaries and pictures and that sort of thing, I was able to see her more clearly and have empathy for both her, the child and myself, the woman who’s grown up and gotten beaten down and said, “No, no, no, I don’t want to live in a world anymore where she’s not out.” Like I want the world to see her as she was at that eight, 10, 12 years old and that’s the journey that I’ve personally gone on and it’s the journey I’m now able to take people on with this book.

Melinda Wittstock:         Hm. Yeah. It’s so, so important. I think we juggle a lot of things and what I’ve come to realize in my own entrepreneurial journey, with myself and anyone else around me, we all have these amazing qualities, but each one of those amazing qualities has a shadow side to it as well.

Natalie Siston:                  It sure does, it does. They do so well to get you to become the valedictorian and to be top of your class in college, and to get that great job and to get into grad school and to find the partner and build the house and have the perfect babies, like it does so well to get you up that ladder, to check all those boxes. And then you get to the point where like, “Okay, gosh, I did all that stuff. And I did it pretty well, but I’m not happy, I’m not satisfied, I’m not fulfilled.” And wow, that’s where I find myself sitting across the table from somebody or the Zoom feed from somebody on a coaching call.

Melinda Wittstock:         Yeah. gosh, if you want therapy, just be an entrepreneur. There are so many things beyond your control, so many things that can be triggering.  It’s actually the journey and enjoying the journey and not about the destination. Whenever I’ve arrived at any of these destinations and I’ve had a lot of successes, I’ve gotten there and it’s felt kind of empty, but the more and more I’ve become, wow, like, am I enjoying my day? Am I enjoying the people I’m working with? Am I doing something that I love to do, everything changes, like in the setbacks aren’t even as difficult anymore. Have you found that?

Natalie Siston:                  It’s so incredibly true. And I mean, this week has been a huge week for me, I launched my first book to bestseller status.

Melinda Wittstock:         Wow. Congratulations.

Natalie Siston:                  Thank you. And it was, talk about being on a high for extended period of time. And then the next day you wake up and your kids still want breakfast and the house is a mess and there’s crises that you have to… Fires, you have to put out in your business and it’s like, okay, and we’re back. And I’m going to remember the pop of the champagne cork that I experienced the night before. I’m going to use that to fuel me, to get through this day, because I can make some highs of today as well. And I think part of my journey, that’s interesting for folks who are listening to your podcast, who might not quite yet be on the entrepreneurial journey is, I built my entrepreneurial path in parallel with being a big corporate person.

And I always considered myself an intrepreneur, because I was always the one trying to push the envelope inside big organizations. And after a while, it got to the point where I realized I needed to vote on myself and step out of those roles. But it’s all translated so beautifully to entrepreneurship and it’s exactly about what you’re saying, it’s enjoying every step of that journey because when you’re balancing all of those things, like I was, I had to take the winds really well because there was just a lot being thrown on my plate every single day. And now I can make great connections between those awesome days in a big corporate setting to those awesome days as an entrepreneur and vice versa. It all has played together in this kind of beautifully dealt hand that I don’t know, maybe I was dealt the right cards, or maybe I’ve learned the strategy to put them in my hand the right way. I’m not quite sure yet.

Melinda Wittstock:         And so what was it, Natalie, that made you quit this corporate job you were doing, you were very good at it. You were very successful and suddenly there’s this pandemic raging all around you and you up and quit. What was it? What was the spark? What, why then?

Natalie Siston:                  Yeah, the spark. So I’m a planner and I was planning on this leap, which doesn’t feel so much of a leap because I’ve been building my business for five years. But I was planning on this starting in 2019, but I was not planning to your point for this global pandemic and I got to the day when I was planning to cut the corporate cord. And it was the same day that the governor of my state shut everything down. And so my husband looked at me that morning and said, “Is this the day to do this?” And I said, “What do you mean, I’ve been building for this so long, you know I’m ready.” And I took it as a personal affront, like he doesn’t think I’m ready to launch my own business. He’s like, “Well, I’m no, no you’re going to do it But, maybe not today, maybe we wait this out for a little bit.”

So I ended up waiting it out a couple more months just to kind of see, okay, is my business going to keep growing? Are people going to be interested in these services? And wouldn’t you know it, in the middle of a pandemic, people start to realize that they are caring about their personal development. They want their team to be more cohesive. They’re looking for an inspirational message to bring to the team.

And I found my dance card for my side business at the time, growing and one night I just had this flashbulb moment to your question that said, “Who quits her job in the middle of a global pandemic?” And very quickly, the wise part of myself said, “Someone whose dreams are bigger than her fears.” And that’s the line that I hang on to every single day when things get scary or unknown or even fun and exciting. It’s like, that’s right, this chasing the dream thing is so much better than focusing on the fears.

Melinda Wittstock:         No matter whether you’re an entrepreneur or whatever you do in life, it’s all about overcoming our fears. And so many of them are hidden, they’re subconscious. What were some of yours? What were some of the fears that you had to let go?

Natalie Siston:                  Oh yeah, I had to let go and I call them barriers and in my book, I refer to nine different barriers. And I’ll just give you a couple of them here, for example. So one that’s not abnormal for many women and even men to think through is this barrier of imposter syndrome. So before we hopped on here, you asked me briefly what my career was like in Silicon Valley and I worked at Stanford University. So I’m coming from the 600 person town, I attended a big state university and now I’m at this elite institution. Where not only am I working with students every day who were supposedly the most brilliant in the world, but also alumni, talk about people who are making things happen in the world. And I was very good at that job, very proficient, but I showed up every day so scared that someone was going to find out that I’m just this small town girl who came from a family of people who didn’t go to college.

And just, I was so nervous every day and I was there in the early two thousands. And so I literally saw Silicon Valley grow in front of me, I was one of the first people to have a Facebook account, because I worked at Stanford and I was able to sneak in under that Stanford.edu address. I was there to see one infinite loop be built for the Apple campus and I never would have thought to go work there as a 22, 23, 24-year-old. And I had to get over that over the next 20 years of my life to be where I am today. I had to remind myself like, no, Natalie, you could have gone for it then, you chose not to because you were so scared, but you are facing those fears everyday now. And you’re getting over the imposter syndrome that’s kind of stuck with you so long. So that’s been one of the biggest barriers of things I’ve had to overcome.

And the second one I’ll bring up, because you alluded to this feeling a little earlier, it’s this idea of emptiness. And I think for those high achievers who are listening to this, they probably are used to the trophy, the accolades, the exciting thing that’s happening and then you get home at the end of the day and you realize like I’m so empty. I just don’t feel, I don’t feel anything and it’s this idea that we’ve let it be about that trophy and we don’t know what to do when the next day comes. And so I’ve had to overcome that barrier, big time, of emptiness.

Melinda Wittstock:         Mm. Yeah.

Melinda Wittstock:         Well, that’s the thing about that destination again, when we seek for, sorry, when we seek external validation for everything we do, it’s pretty difficult to be happy because first of all, we can’t please everybody. Second of all, we get to that destination and there’s always a new destination, so really the trick is looking inside, figuring out what it is that makes you happy. And yet we’re taught kind of not to do that. That it’s all sort of external to us when actually our happiness is really entirely under our own control.

Natalie Siston:                  I couldn’t agree with you more and I think that’s why we’re seeing a big movement in schools and other places to teach kids about gratitude and the focus on the little things. And everyday say the thing that was good about your day. And I feel like those practices add up and they start to really make a difference that way when we get to that point in our life where the big promotion happens or whatever, it’s like, we can be like, “Yeah, I got promoted today.” And this other really cool little small thing happened to make it as good of a day as it could have been.

Melinda Wittstock:         So tell us a little bit more about your book, first, I mean, because a lot of people listening here have these dreams of eventually, one day, someday, they’re going to write their book. So what was your process? What did it take for you to get it written and out there and bestseller status?

Natalie Siston:                  So I’d love to, because I admire the people that are listening because, and I will speak to them from both have a left brain and right brain side, if that’s okay with you. Because it takes up both sides and so from a right brain creative process, it was a total unfolding as it should, kind of moment. So I like to say that writing my book was the ultimate moment of being in flow and it just happened to take a six month period of time to be in flow. But the idea for the book came about a year ago and I just submitted an idea for a Ted talk in my town. I was not selected for the Ted talk. So I immediately started turning that idea into other keynote presentation submissions and I was starting to get selected for, at last count I had four keynotes scheduled for the beginning of 2020 and the pandemic hit and they all got canceled.

And so I was looking at this idea, I found all the diaries that I’ve kept since I was eight years old and I found those kind of on the Eve of my 40th birthday. And I thought, gosh, I should probably start to look at these and the brilliance that was in there from that eight-year-old who started writing them in third grade to the woman who wrote till she was 25. So, I pretty consistently kept a diary that entire time, I was like this man, that’s who I want people in the world to see, that’s who I want to feel more like. And so this idea was churning in me, all these talks got canceled and I sat back and I was like, “I think this is my book.”

Because I’ve tried to start two different books, so for those who have tried and quit, like don’t feel bad, we’ve all done it. It means it wasn’t the right book and so this, I knew it was the book, I hired a book coach. This kind of gets to left-brain side, so the getting it done piece. I hired a book coach named Kathy Fiak, who was amazing and she just helped me keep my stuff together, we talked on a weekly basis. She kept me organized because I would say my book writing was more of a curation experience, because it was collecting diary posts or diary writings from many years. It was taking blog posts I had already written over the past five years and pulling it all together for this cohesive theme. So it was an ultimate curation experience, which I thought was a lot of fun.

And then I hired a publisher to work with me, called Ignite Press, they’re located in California and they did all the things that I’m so glad I didn’t do, if I had chosen to self publish this book. So they hired a copy editor, they figured out how to get an ISBN number, like the day they said, “Hey, your books going to the Library of Congress this week.” I’m like, “What? Like that happens? I don’t even know what that means.” So, they figured out all the nuts and bolts and how to get it on Amazon and all of these things. So I had them do the technical aspects of it, but it was for me from the time I decided to write the book until the time it came out, it was about a seven month period of time. So I would say for anyone listening, who has inspired action and wants to move things forward, it is totally possible if you have the right resources to help you through that process.

Melinda Wittstock:         Exactly. So how do you know if it’s the right book or wrong book? I mean, you mentioned getting into flow state, which really intrigues me?

Natalie Siston:                  So I can tell you how I know from it being the wrong book. So I wrote a year-long blog series a few years ago, called 52 Weeks of Meaningful Connections and so every week I had a blog post that was about connecting with people and they were personal stories or there was research or anecdotes, whatever it might be. And I had intended to turn that into a book, I thought, well, that’s pretty, a no brainer, set it up like that, have people start it on a given week and they read a chapter a week type of thing. And so I printed out every single blog post, I took a long trip over a weekend, I’m like, “I’m going to get this organized and get it ready.” And I did all the steps, I did all the left brain things, I printed it out. I had an outline and I could not get myself to open those pages. It just did not feel right and so the complete lack of motivation, it would have felt like a chore to pull that thing together.

So, for those who are interested in that content, it lives out in the world on my website, awesome, go get it, but it’s not going to be a book. And this case, it literally, I sat down, mostly it was in the early mornings. I would look at these diaries and I had a little thing of post-it tabs, five different colors and every tab meant something different. Like, Oh, this is a great quote or wow, talk about the feelings there. Or, Oh my gosh, this is gut wrenching and I don’t want anyone in the world ever to know that I said this type of thing. But doing that exercise, every day I read more and more of those diaries, I just knew that there was more and more to say.

And so I’m probably one of the few authors who actually had to cut a lot of words in my manuscript, from the time, had all the words to a final thing is, I had to cut down about 20,000 words to make that happen. And so I feel, that’s when you know your flow, is you’re swimming in content, you’re swimming in ideas and you don’t want to stop. And I think what’s also been really compelling is I pressure tested this idea with people, I did a group coaching program before the book was finished with a group of women who I thought were the ideal reader and they kind of guinea pigged my concepts and the content and the questions. And so I know it will work, I know that the framework I set up in the book will work because I had people try it out.

So I just shared the idea with a lot of people and you kind of lean into their excitement and when somebody is excited about what you’re working on, you have that extra layer of accountability. So I think somebody knows it’s right when they’re excited about it, when there’s always more and when they literally can not wait for it to be put out in the world, there’s no being petrified about that.

Melinda Wittstock:         Yeah. So, so true. I mean, it’s curious what you say, because in a way you co-created your book with your customers. You were almost market testing it, you’re in flow, but you’re also… And that actually is really the best way to develop any product, app, podcast, anything. It’s really knowing, knowing, knowing your audience and who you’re writing it for.

Natalie Siston:                  Yeah. And the best laid plan is mere merely that a plan, because the minute you step that into the real world and it blows up, you’re like, “Oh, I spent all that time planning.” So don’t get me wrong, planning is very important, but you got to be flexible and go with the flow. I had seven people on my editorial board, review the book before it went to the copy editor and these are friends, they’re colleagues, they’re people whose writing I admire. And I said, “Read the book and call out all the things that don’t make sense or you want more of, they’re confusing.” And that process totally shifted the book, the book is not in the same order it was when I envisioned it, because the editorial board said something was confusing. And so I sat with that feedback for about three weeks going, “Gosh, like I hear them, I know what they’re saying. I don’t know what to do with it yet.”

And once again, I had to wait for that moment of, “Oh my gosh, now I know how to do that, I have to flip sections one and two, I have to insert this part in the middle.” I have to put literally in my book, I have how to use this book directions up front because the editorial board is like, “Oh my gosh, I feel like people could use this in so many ways. You should set that up for them. So it’s easy.” And truth be told it’s a business building technique too, Melinda, because in the beginning of the book, I’m like, “Read it with your book group, do this with a book club, read it with friends.” Because my hope is that a person reads it, they’re like the beta reader and they’re like, “Oh my gosh, we need to do this for our next book club.” Or we need to bring this into our women’s group at our organizations, that type of thing.

Melinda Wittstock:         Mm-hmm (affirmative).

So with all the women that you work with who are entrepreneurs and building teams, executives, and whatnot, apart from imposter syndrome and all the work/life balance stuff that we all juggle with, what are the biggest challenges and what are the biggest learnings they get from working with you?

Natalie Siston:                  It’s a great question, I had my like trifecta of beautiful coaching clients this year, who are all C-level women at small organizations and many of them seeking the top spot or in the process of trying to get to the top spot and, so I always try to ask people like, if you could succinctly say the thing you would like to get out of this engagement, hands down, all the women this year said confidence. And I think it’s a sister-to-imposter syndrome, but it shows up a lot differently. So confidence to them is not being able to speak up the way they would like to, oftentimes, in front of kind of alpha male leadership teams or client sets. And so I did a lot of work this year on helping these women just feel confident in their own knowledge, their own abilities, that way they don’t second guess themselves every time they go into a meeting.

And I think there’s also the element that comes along with the kind of maternal instinct is like, you can also stop doing all the little things that the token woman at the table does. And so then being able to strip away those two things has just meant some beautiful results for these women saying, “Wow, now I kind of understand what it means to be stepping fully into my own power in a new way,” because obviously these are very accomplished women to make it to where they’ve already made it, but they need that extra push, extra boost to get themselves into the top spot, which we both know is just one more step on their journey, that’s not their ultimate destination.

Melinda Wittstock:         Exactly. Well, speaking of ultimate destinations, where are you headed? What’s next for you?

Natalie Siston:                  I love that question because I think 30-year-old Natalie would have had a five-year plan for you, but 40-year-old Natalie is like, “I am literally in a moment of letting the results of this book and the coaching I’m already doing and the work I’m already doing flow freely.” Every time I try to sit down and do a business development push, it feels hard and then lo and behold, my email will start to fill up that day with inquiries. So I’m definitely doing outbound marketing, this is not that I’m sitting on my hands doing nothing, but I have told everybody who’s been with me, on the Let Her Out journey is, the launch of the book is not the end all be all. This is a movement that I’m building and so my hope is that in a year from now, we see an entire Let Her Out movement and I’m open to that unfolding in lots of different ways.

I definitely will keep my group coaching offering as part of that book. I will definitely keep doing lots and lots of keynotes, that’s my goal for 2021 is to be on as many virtual or actual stages as might allow.

Melinda Wittstock:         An actual stage, oh my goodness, what would that look like?

Natalie Siston:                  I know an actual would be beautiful. And then also just seeing how a community unfolds with this and I have not set up a Facebook group for people who’ve read the book or anything like that, because I want to see what the women and men who are reading this book will want for me. So I’m keeping things open and I’m ready for the readers. One of the last things I put in the book, it was one of those, this is the last, last, last chance you have to make any changes. And if you make any changes beyond this, you will incur extra fees, type of thing you get from the publisher.

And so, one of the very last things I added was the end of books are always the what to do next, leave a review, tell a friend, yada, yada. And in mine it was, tell me your story. I said, “I just told you my story. And I feel like I’ve given you many, many openings to think about your story differently, so please share that with me.” So I think there’s a sequel to this book and I think it’s stories that come from those who read it.

Melinda Wittstock:         Oh, what a beautiful, beautiful idea. Well, what a wonderful mission and I love the way you’re approaching it.

Melinda Wittstock:         And so Natalie, I want to make sure everybody knows where to find you, work with you, and of course get your book.

Natalie Siston:                  Terrific. The easiest place for anyone to go right now is to Let Her Out.com just as it sounds, letherout.com and there you will find all of the links to all of my social channels and a way to contact me directly. And I invite anyone to follow me on Instagram, Facebook, LinkedIn, I am there very regularly and always enjoy building community.

Melinda Wittstock:         Fantastic. Well, thank you so much for putting on your wings and flying with us.

Natalie Siston:                  I look forward to hearing this and to see where things take you as well, Melinda. Thank you.

Natalie Siston
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