Aspire with Emma Grede - The Five Lessons That Shook Me This Year
Episode Date: December 16, 2025In this solo episode, Emma Grede looks back on the conversations that shaped her most in the first year of Aspire. From billion-dollar founders to cultural icons to the people closest to her, Emma rev...isits the moments that shifted her thinking, changed her routine, and genuinely shook her this year. These five lessons span money, mindset, ambition, career, and emotional resilience. Together, they reveal a truth Emma returns to constantly: success is a lifelong practice of learning, unlearning, and returning to what matters. If you’ve been feeling stuck, rushed, overwhelmed, or unsure of your next step, this episode is a recalibration. Which of the five lessons hit you the hardest? Drop your biggest takeaway in the comments below, and if this episode moved you, make sure you subscribe so you never miss the conversations that help you grow, thrive, and aspire. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices
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So I don't know about you guys, but when I listen to a podcast that I really love,
I tend to go back again and listen for a second or even a third time,
because there will always be something in there that either I loved and I want to double down
on or something that I completely missed.
Now, we've been doing this podcast for almost seven months,
and so what I wanted to do was pull out some of the parts that have been the biggest game
changes for me. The things that I've taken into my routine, the things that have shifted my way of thinking,
and the things that really move the needle for me. Because when I decided to do this podcast,
it was really about sharing information, giving you an insider's look on how excellent people
get stuff done. But it was also about finding more ways to connect with people and ultimately
finding more ways to learn and to feed my own appetite to learn. So today, I'm going to go back
to some of my favorite episodes to show you the things that moved me the most.
For me, there is no one more helpful when talking about business than Mark Cuban,
because he ain't going to sugarcoat it, but he's also never going to overcomplicate things.
And sometimes a simple answer is all that's needed.
So when I ask Mark, what's the one thing you wished every founder knew?
He told me this, sales, cures all, meaning that you either have the sales or you don't have the sales.
and therefore one of the most important traits any entrepreneur can have is learning to sell.
Now, listen carefully to this one because sometimes the best stuff is so simple, it just passes you by.
This wasn't just a simple answer. It's the ultimate business truth because if you have sales, you'll figure everything else out.
And if you don't, you don't have a business. You have a hobby.
So thank you, Mark, for making it so simple. Let's free visit.
What's something that you wish every first time found a new?
sales cures all.
Sales cures all.
No sales, no company.
That's it.
No exceptions to that rules.
Because people get amored with all the other stuff,
a maud with their model,
the marketing,
and it's like you need sales.
I talk about this all the time.
It's like focus on distribution,
focus on your sales,
focus on like owning that story
and just being the best salesperson possible
because that's all you need at the end of the day.
Right, because if you can sell.
Yeah, you'll figure the rest out.
Yes, because everything else is not a problem.
is through to that sale. If you can't sell, it doesn't matter what you're good at. It doesn't matter
anything else for that matter. You're stuck. Why do you think people avoid that? Because people
don't like to be told no. Oh. You know, I tell people all the time. Every no gets you closer to a yes.
Every no. And I would tell that to myself, I was selling magazines door to door, right? And I'd walk up,
are you telling me that for $5 a week, this wasn't going to improve the education and enjoyment of your family?
No.
On to the next one.
And it's the same.
Selling Mavis tickets.
Switch up your pitch.
You know, when I first like the Mavs,
hey, it's less than McDonald's.
No, you guys suck.
Boom, on to the next, right?
You've just got to be relentless
and most people are afraid of the word now.
Are you afraid to give the word no?
Because I feel like getting the feedback is really hard.
You just give the feedback, right?
No, I don't like to say no to people.
That's my problem.
That's why I don't do hiring to my companies.
Oh, right.
Is that true?
Oh, yeah.
Because I'm awful at hiring people.
You're just like, I'm on board.
No, I'm like, I'm a sales guy, right?
So like, I think I can make this work.
What is the truth then in entrepreneurship that no one actually tells you?
The truth that no one is the truth.
It's hard.
You know, it's, it's, there's, I think you're not automatically going to make money.
Most people don't make it.
Most people fail.
It's hard.
Yeah.
That's, I think, what I've seen.
And it's interesting, actually, as you go into the town,
because even if you think an idea is a great one and you think it has a market, like not everything
works out. No. And you can give the funding and it just for, I don't know, a myriad of reasons
might not work. It fails. Yeah. Most companies have you failed. Yeah, of course I've failed. You
never heard about my powdered milk company. No. I started out of college. Not a good one.
Not a good one. It was cheaper. It didn't matter if it didn't taste like milk. It was powder milk.
All right. Tell me about the powdered milk company. Well, I want to know about the failure. I want
I don't know, what does it mean to fail and get back up and do it again? Like, what is it in you
that allows you to take the failure and it not be about you? Damien John says it best.
It's the power of broke. You're broke. What else are you going to do? I mean, I was eating
mustard and ketchup sandwiches. I was going to a bar with $5 buying one beer and eating all the
fried mushrooms and the peanuts and whatever shit. Broke is good. Broke is great for a period of your
life. Yes, right? Because you've learned. Yeah. Yeah, it's really true. But what have you learned? Do you feel like
the failures that you've had, have they amounted to something that you've been able to see, like, as a
pattern in your life? Or is it more just about the individual circumstance? Because I feel like I could
look at every failure I've had, and I'm like, basically the same thing. I don't know if it was basically
the same thing other than maybe shit didn't sell, right? Is that? Powder milk? Yeah. It didn't sell.
did not sell.
I remember taking samples to people mixing up, like, look, milk's expensive.
We're broke, right?
It's save you money.
It's some grainy shit.
And just seeing the look on their face.
No, you can do about that.
Point taken.
You're like, I got it.
But it's just you.
Your taste in milk is different, right?
All right, so how long, because this is that kind of love.
About a month.
How amounts?
Yeah, about a month.
Yeah, but isn't that the thing?
At least you didn't try to do that for a year?
Because some people just don't.
know how to step away.
But doing no sales.
It was going nowhere, you know.
I know, but people don't always hear that.
Don't you think, like, you must deal with a lot of early stage founders that just don't read
the signs.
They don't see it.
And I think it's really important to talk a bit about failure and to talk about when it's
time to pack it in.
You know, I never really thought of it that way, but you're right.
You have to have a lot of self-awareness to be an entrepreneur.
It's no secret that I love Michelle Obama.
But what she left us with after her episode was more than that.
just great, quotable Michelle moments for me. The biggest single takeout was this idea of there being
these defined chapters in your life and bringing an awareness to the fact that life doesn't all need
to be figured out in one day. For me, this was more than a little bit reassuring because as a highly
ambitious person, I do find myself in a rush to get to the next big thing. Every now and again,
I wonder why what I'm working on isn't happening faster, why I'm not seeing the results that I want right
away or the sales that I want right away or thinking like why didn't this thing happen exactly
as I'd intended. But Michelle made that all go away with just this very simple reflection.
When I look at my life so far with the benefit of hindsight, I know that there've been chapters
when all I've done is work. There've been chapters when, honestly, I haven't had as much work
as I would have wanted. There've been seasons where everything I tried didn't have the desired effect
or flat out just didn't work.
But this idea of your life coming in chapters or in seasons
is a really helpful framework,
especially for those of us who need to make sacrifices,
sacrifices that slow us down,
or when something stands in the way that you didn't choose.
Like losing your job, someone getting sick in the family.
What I know for sure is that life will throw you curveballs
because you can be in a season that, quite frankly, isn't about you.
It's about your kids.
It's about somebody that needs something from you that takes precedent,
But knowing that nothing is finite, we don't actually need all the things in the exact moment
because there will be another moment. And allowing yourself to be at peace with the decisions
that you sometimes have to make was so liberating. You know, being a wife to the leader of the
free world, to, you know, your own career ambitions and all your own aspirations as well.
And I wonder if there is like a critical and honest piece of advice that you can give or that you can share based on your own journey and what you would say to women that are trying to seemingly have it all, do it all, live to the fullest.
I've said this a lot.
It's impossible to have it all.
So stop with that.
First of all, you can have it all over a period of time.
but this impatience and this feeling of like, I've got to be, I've got to have the exact job at the top of the game.
And I want to be the best mom to all to the, you know, I want to be there, be at all the stuff.
And I want to look my best and be in my best shape and be emotionally intuned.
La la la la la. And my marriage has got to be on point.
Like, it's, it doesn't, you can't do all of that.
There are tradeoffs.
And it's okay.
You know, if we're blessed and we can take care of ourselves emotionally and physically, life is long.
And you can have chapters.
And you don't lose out because you, you know, you didn't read the whole book in one sitting.
Each chapter can be really special.
When my kids were little and I was sort of ready to drive in my career, but Barack was a,
state senator, and then he ran for Congress and lost, and then he was a U.S. Senator, he was away
more than he was home. I got to a point where I said, I can't be in the highest driving point
in my career life. I just can't. So I left running a nonprofit that I enjoyed running,
but running a nonprofit is an all-consuming, and the nonprofit didn't have a lot of money,
and I needed flexibility. Did you do it happily?
Or was there resentment there?
There was a little resentment.
But I was happy because I love my girls and I love the time that I spent with them.
And I felt more at peace with that decision because it was the right thing for them.
And ultimately for me, because it gave me balance that I needed at that time.
And I used myself as an example.
I did that.
And it didn't stop my growth.
It didn't, you know, I went on after that.
I became an associate dean.
I was the vice president and head of community outreach for the University of Chicago
hospitals as the girls grew.
And I felt more secure.
I started re-aligning myself.
People don't realize they can take a little pause.
Yeah.
Like life doesn't really give you the feeling right now that you can just be like, hold, please.
That's right.
For whatever reason.
And you can, and you don't.
don't have to stop. Like, I didn't stop. I thought about quitting completely. And then I got an
opportunity to get a good job that I enjoyed in a flex situation. I negotiated flexibility for myself.
I negotiated flexibility first. That wasn't flexibility. It just was less pay. And I was irritated at
that because I got half the salary and was still doing a full-time job. So I learned from that. I was
like, never again. I'm too much of a driver.
to ever get paid less, right?
So the next job, I was like,
pay the full salary,
but give me hard blanche over my schedule.
I will get the job done,
but I'm picking up my kids from school.
I'm going to the Halloween parade.
And I might not be here on Friday,
but I'll be here when I need to be here.
So pay me, right?
I learned that.
So I would just say out there to women,
it can come.
And if you are choosing to drive,
which that's a choice,
then don't parent from guilt.
All.
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It will probably go down as the most succinct message ever delivered on the show.
But when Melody Hobson said, you have to have a sense of urgency.
You have to want to be great.
To me, it was like, here's what separates the best from the rest.
I've said it on many occasions that not everybody has to be ambitious.
We don't all need to start businesses or want to be at the very top of our career.
But if you do, there are a couple of non-negotiables and a sense of urgency and how much you care are two of the most important traits of any successful person that I know.
Now, when we hear stories about people that do things that should take five years in one year or should take five weeks in one week, there is no secret.
You know, you simply cannot underestimate the importance of moving fast and a first move as advantage.
I've worked in fashion for most of my career
and sweating the small stuff or caring the most, as Melody says,
is what the best people in the business do.
The ones that care about every component of how our products has made,
every stitch, the lining and the trim package and the fabric and the construction,
then how it's folded when it gets on the shop floor,
how it's put in the bag, how it's packaged to the customer,
the experience of unboxing and on and on and on.
That is the difference between the best and the rest.
There's just some stuff that you cannot argue about.
If you want to be great, urgency and caring the most is a great place to start.
So many people that are sitting there in a corporate career.
And I do think to some degree there is a blueprint for getting promoted from moving through a job in the way that you have.
So what do you tell people?
I mean, because you're on an 11.
Do you need everybody else around you to be on a 11?
and 11 and what is it that people need to do in order to be successful and to be promoted
where they're at?
Okay, this is going to sound strange, and I'm going to make it hopefully not sound not great,
but it's how I think about it.
My mom had six kids.
She mothered us all differently.
That's just a fact.
No siblings have the same parents.
No.
That is a fact.
It's a fact.
directly with me, I understand what they can do and how they can do it.
John Rogers always used to tell me that the World Championship Chicago Bulls that won seven
championships, he said, Dennis Rodman rebounds, Steve Kerr shoots threes, Michael is the greatest
player of all time, you know, he would go through each player. And he said, but each one is really
important. Michael can't play without them. They can't win. So Dennis may be out at night,
but everyone makes sure Dennis is on the court
so that he can rebound for them.
And he's like, so he doesn't have the same rules as everyone else.
And so, Melody, you figure it out that you get the best out of each person,
but everyone is not going to run the place.
But what happens if your aspiration is to operate at the highest level?
Like, what are the non-negotiables do you think for people that want that type of career?
What do they need to do?
You must.
And I mean this with serious.
intensity, I think you have to care a lot and have a sense of urgency. You have to have a sense of urgency.
You have to want to be great. And if you want to, there's a, you know, I love that book by
Jim Collins, Good to Great, and the first line of the books, good is the enemy of great.
Good is the enemy of great. Plenty of people are happy with good. They say the worst student is the B plus
student. Because the B plus student, I was like, it's fine. It's good. It's a good. It's
They're like, the C student aspires for something better.
And the A student is just the A student,
but the B plus student is, they live in that no man's land of its fine.
And so it's almost like the worst situation that you can be in.
So if good is the enemy of great,
I want the person who wants to be great,
but understanding that differential between good and great is really hard.
Do you think you can train people into that
or do you think it has to come from somewhere within themselves?
It has to be there.
Yeah.
Yeah.
Yeah, some people just, you know, they come out of the wound with it.
Some people don't, but that doesn't make them, they can still be very valuable.
They're just going to be a certain kind of player.
And that's what John said.
He's like, there going to be other people.
They're just not going to run the place.
So you think people have to just work really hard, want to be great, and they need to have a sense of urgency.
I think they have to want to be great.
Let's start with that.
And, you know, some people have to work harder than others.
So I remember going to school with geniuses at Princeton.
They didn't have to work as hard as I did.
They, you know, sort of like skim the page and got it.
And I'm like writing notes and checking, you know, flashcards and doing the whole thing.
But, you know, it came easier to them.
Some things come easier to me.
So I think it's just a function of you understanding yourself.
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I was so excited to speak to Reese Bitherspoon because she's someone that I've just loved since she was in cruel intentions.
I've devoured every movie that she's ever done and I love it when you get to meet people and they don't disappoint.
Reese is obviously a powerhouse.
But the last conversation I expected to be having with her was one about money.
And let me tell you, Reese did not mince her words.
She has a passion for helping and enabling other women.
And so when she spoke on this podcast, she came to do exactly that.
And let me tell you, anyone, anyone that's happy to part ways with their best money advice
is someone I'm going to listen to all day long.
So what's the one thing that every woman needs to know about money?
Do you think?
Oh, my God.
Where do I start one thing?
Well, go on.
Give us it all.
Well, first of all, I learned about money from doing things wrong.
Yes. I don't know a woman, Emma. I do not know a woman who doesn't have a disaster financial story in her past.
Facts. Whether it's her, her best friend, her sister, her mom, her grandma, her auntie, she lost all her money.
Or she got divorced and she got stuck with the bill. Or, you know, just whatever financial debt. So much debt. And so I listen to every podcast on finances. I am so interesting.
and financial wellness for women.
And just also, a lot of what we learn is one course, three days in high school.
We're lucky if you get three months.
Yeah.
And that was the end of my financial learning.
And then I became this woman.
I was making money and I was a young mom.
And I did not save correctly.
I'm in fine.
I'm fine.
But you mean you're fine.
You're not like, are you not rolling in it like now?
Like, just fine.
I did invest properly. I'm not not saying that it wasn't, I'm completely fine. And I did well,
but I could have done amazing if I had learned a few things. And a lot of them are mindsets.
Right. Mm-hmm. About saving, about the steadiness of the stock market and index funds and
diversifying your portfolio and making sure that you're looking at treasuries and you're looking at
bonds and yields and things that are pretty simple if somebody says them,
to you in a, like if you're a visual person, you see a visual chart. I'm a visual person. So
every time I talk to people about finances, I need it laid out. I need it laid out. And I want
cute colors. Yes. I'm just being honest. Notes. I want a pleasing palette and a pie chart.
Thanks. Damn right. We know what your business managers are doing.
Making this very aesthetically pleasing presentation. Like, can somebody do the pie chart for a reason?
But I love that you say that because it is all pretty simple. But again,
we're not always having those conversations and sharing the information.
What's the best piece of money advice you think you've been given?
Don't get into debt.
Do everything you can to not get into debt.
And pay off those credit cards or don't spend the money like it's yours.
It's not yours, girlfriend.
Yeah.
And that was a really good piece of advice.
Don't ever let somebody control you with money.
Somebody says, I'll take care of it and I'll take care of you and I'll take care of this.
that person could leave, that person can hurt you.
You always keep your job.
Your job is your life insurance.
My mom used to always say that to me.
Oh.
And my mom went through some tough stuff in a marriage with finances.
Really tough stuff.
Yeah.
And so to my grandma, not in the marriage, but in like a family structure.
And I have this past of women not being taken care of financially.
And so I think.
You too.
Right?
And as a little girl, it scars you, like literally.
It's living inside me.
So, so deeply.
And that's why I have a passion for helping women understand.
And also demystifying it, you know?
Yeah, I feel like the demystifying piece is really, really important.
Do you, are you the type of person that looks after everything yourself,
or have you kind of outsourced all of that to a team at this point?
I have outsourcing, but there's frequent check-ins.
Same.
Weekly.
I'm the same.
I like to have enough of that, you know, it's like one hands on it all the time.
Like, I'm happy to let the experts be experting, but I need to like, I need it there.
Yes.
Yeah, I need it there.
And then I also need checks and balances.
I need to diversify things so that everything's not in one investment or one savings account.
Yeah.
But that's it.
That's what I did for a long time.
It's like, if nobody teaches you that, you don't know.
And you're just like, okay, the money sits all here and it's safe.
but it's like, it might be safe, but it's not growing. It's not doing it for you.
Right, right. And most people don't live in a way that savings is even part of their life.
Okay, so I'm very realistic about that. Yes, you have to be.
My mom and my grandma always saying to me, you know, they did have, my mom has retirement because she
worked her whole life doing three and four jobs, including being in the military and being a nurse
and working in a state university. But you have to think ahead. And you have to think
think about saving as helping your future self. Oh yes, absolutely. What you don't spend today,
you're saving for your future self. You're saving for 65-year-old Emma who doesn't want to have
to worry about the gas bill. Yes. Yes. Yeah, I want to relax as an old lady. Yeah, me too.
Eventually at some point. No? I want to have a glass of wine and sit on a porch. A porch. I want to come
on that porch. We're just going to sit there and tell our stories. Talk shit about all.
We're like, you know.
We're going to travel where we want to go.
Oh.
And our cute kids.
Wouldn't it be joyful?
Oh, my God, we have the best time.
Now, the outpouring of love that came in after I spoke to my husband on this podcast was
really something that I never expected.
I think it's because he was both honest and vulnerable when he spoke about anxiety.
And anyone who suffers from anxiety will know it's not something that you can control.
There's no switch to turn it off.
There's no framework that magically helps you.
It's a constant.
It's constant.
and it's a constant battle. So it made me so happy when Yenz reframe the idea of having anxiety
as a superpower. And he spoke about no longer judging himself for having anxiety. You can be with
someone for years and years and years and learn new things about them all the time. And there's
nothing better than learning from someone you love and then being able to share it with a lot of
people that could benefit from it at the same time. So a huge, huge thank you to all of you that
broke to me and commented, I'm really so happy we did this episode. Let's take a listen.
And I want to understand a bit more about anxiety as it relates to your career and your life
and your business. Because I think that we're so much conditioned to see anxiety as a weakness,
and I know you think about it as a superpower. So will you, when did you start seeing it as a
superpower and will you just talk about it a bit for me? Very late, probably in my late 30s,
where I really understood.
And I did that through work I was doing
with a highly spiritual person
who asked me, I said, I want to change.
I don't want to be this anxious person any longer.
I want to feel whole.
And he said, are you sure you want to change?
I said, yeah, this is a negative thing for me.
This is big, you know, my days are heavy.
And he said, if you change, it also will change who you are.
You're not just successful because, you know, despite your anxiety,
you're successful because of them.
there's so many positives that are driven and so many skills that comes from your anxiety
that if you change that, you might not be as good as you are today.
You might not be as good version.
You might not be as an effective founder, entrepreneur without it.
Are you sure you want to lose that power?
And that was...
Oh yeah, that was, I walked out of that room.
I remember.
Dr. Tran, right?
Yeah, Dr. Tran.
Nothing had changed and everything had changed at the same time.
Yeah, I mean, I think that that, even just you saying it, and I know that story so well,
I feel like it is so important for people to hear because we all have parts of our personality
that are useful or less useful, more useful or less useful.
And it's not often, like we don't often put things in the right order.
We don't often understand how some of those things that can be troubling to us can also enable us.
Yeah.
And anxiety can be debilitating, can be crippling.
And indeed, for many people, something that they need to get treated.
At the same time, anxiety is a human,
emotion.
It's a part of our human experience.
We all have it to some degree.
It's healthy to have a dose of anxiety.
It's helped just like it's connected to fear,
which is a natural human emotion, reaction.
It's our ability to feel love, sadness, you know, joy.
Anxiety is part of us.
I have more of it and I have so much of it that for a long time in my life,
every day was just harder for me than it was for other people.
And I kind of started every day at a negative.
Yeah.
Right.
So I had to overcome that to do anything.
I had to overcome anxiety to meet people.
I had overcome anxiety to get out in traffic, to get on an airplane, to be on my own.
So I always was so, it was exhausting.
It was really, really exhausting.
It still is often exhausting.
How do you know when anxiety is fueling you versus controlling you these days?
I think it does both.
I think it does both for better or worse,
but I don't judge myself for having anxiety anymore.
I accept it.
I see it as a wave,
and when it comes, it can be imposing,
and in the middle of the wave, you feel hopeless.
But I know the wave is going to wash over,
and I know there's still, the water is still on the other side.
So what am I going to do?
Never get in the ocean.
Is that better?
Or am I going to start getting scared of the sand?
You know, the problem, and I'm sure other people, if anyone listens to this,
who suffers from anxiety, and I'm sure many do,
the more you tailor your life to avoid situations which makes you anxious,
you're getting anxious in lesser situations.
When you lower the bar, that becomes a new bar.
You need to lower it again.
And life gets smaller that way.
It's a very tricky subject.
Everybody have their own journey.
And I can only speak on my experience.
I'm not saying that's translatable to other people.
They have to have their journey and they know themselves best.
I can only speak of mine.
but my personal experience is that I do better when I challenge it.
These five conversations each taught me something different about resilience, about grace,
excellence, confidence, and self-acceptance.
And together they remind me that success is a lifelong practice of learning,
unlearning, and returning to what matters the most.
If this episode leaves you reflecting or inspired, that's the whole point.
because the people who move us don't just share their wins. They share their wisdom.
Thank you so much for being part of Aspire this year. We have so many more wonderful episodes
coming in 2026 dedicated to helping you grow, thrive and bet on yourself. Here's to stay in curious,
stay in bold and always, always aspiring. See you next time. If you're loving this podcast,
be sure to click follow on your favorite listening platform. While you're there,
give us a review and a five-star rating and share an episode you love with a friend.
be so grateful.
Aspire with Emigreed is presented by Odyssey.
I'm your host, Emagreed.
Our executive producers are Corrine Gilliard Fisher, Derek Brown, and me.
Our executive producers from Odyssey are Maddie Sprung Kaiser,
Leah Reese Dennis, Asha Saluja, and Jenna Weiss Berman.
Stephen Key is our senior producer,
sound design and engineering by Bill Shorts.
Angela Paluso is our Booker,
original music by Charles Black,
video production by Evan Cox,
Kurt Courtney, Andrew Steele, Carlos Delgado and Arnie Agassi.
Social media by Olivia Holman.
Special thanks to Brittany Smith, Sydney Ford, my team's at the lead company and WME.
Mora Curran, Josephina Francis, Hillary Schuff, Eric Donnelly, Kate Hutchinson Rose, Tim Mekyll, Sean Cherry and Lauren Vieira.
If you have questions for me, you can DM me at Aspire with Emma Greed.
Greed is spelled GR-E-D-E.
that's Aspire, AspI-R-A with Emigre.
Or you can submit a question to me on my website, emigreid.migre.com.
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