21 min read
From Stranger to Must-Know: How to Stand Out and Grow Your Network
Joe Rando
:
Feb 18, 2025 8:16:42 AM

What if your online presence was so warm and inviting that total strangers had to meet you?
That’s exactly what happened with our guest, Greg Wasserman! Before we even knew him, we knew we needed him on the show.
Greg is a master at building relationships—both online and in-person—without being salesy, spammy, or sleazy.
How do you create authentic connections that actually lead to opportunities? Why does networking not have to feel like an awkward name-tagged free-for-all? And is there a secret formula for standing out in a sea of LinkedIn messages? (Spoiler: Yes, and Greg shares it with us!)
Like the show? We'd love it if you'd leave a 5-star review!
Connect with Greg Wasserman
- Connect with Greg on LinkedIn.
Favorite Quote About Success:"
"I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. Twenty-six times I’ve been trusted to take the game-winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed." - Michael Jordan
Being a solopreneur is awesome but it’s not easy. It's hard to get noticed. Most business advice is for bigger companies, and you're all alone...until now. LifeStarr's SoloSuite Intro gives you free education, community, and tools to build a thriving one-person business.
So, if you are lacking direction, having a hard time generating leads, or are having trouble keeping up with everything you have to do, or even just lonely running a company of one, click here to check out SoloSuite Intro!
About Greg Wasserman
He's transitioned from exceeding sales quotas and managing teams at Yahoo! to leading partnerships at startups, where he developed innovative revenue streams and built communities that drive business growth. Throughout his journey, he's earned a reputation as "the guy who knows someone" or "the guy with the answers."
Episode Transcript
Carly Ries: What if I told you that the way you present yourself online could be the key to unlocking amazing opportunities without a single cold pitch? That's exactly what happened with our guest, Greg Wasserman. We'd never met him before, but the warmth and authenticity of his online presence made us instantly want to have him on the show. In this episode, Greg breaks down the real art of relationship building online and offline. Forget robotic networking tactics and spammy LinkedIn messages.
He shares how to create genuine connections that open doors in unexpected ways, why playing the lawn game is the only game worth playing, and how just showing up can transform your business and your life. If you've ever felt awkward at networking events or wondered how to stand out in a crowded digital world, this episode is for you. You're listening to The Aspiring Solopreneur, the podcast for those just taking the bold step, or even just thinking about taking that step into the world of solo entrepreneurship. My name is Carly Ries and my co host, Joe Rando, and I are your guides to navigating this crazy, but awesome journey as a company of one. We take pride in being part of LifeStarr, a digital hub dedicated to all aspects of solo entrepreneurship that has empowered and educated countless solopreneurs looking to build a business that resonates with their life's ambitions.
We help people work to live, not live to work. And if you're looking for a get rich quick scheme, this is not the show for you. So if you're eager to gain valuable insights from industry experts on running a business the right way the first time around, or want to learn from the missteps of solopreneurs who've paved the way before you, then stick around. We've got your back because flying flying solo in business doesn't mean you're alone. So, Greg, you don't know this, but one of the reasons we have had you on the show right now is how you present yourself in the interwebs.
We just met you. We don't know you. However, both of us are like, we need to have him on the show. And it's because you just kind of embody warmth, and Joe was just saying offline that we're, like, a big warm hug. But I was like, there's something about this guy that makes you wanna know more, and I feel like that's a teachable thing that we tell our audience, for people that are trying to network.
So before we get started, welcome to the show, and thank you for being you because, honestly, you are what got you on the show today.
Greg Wasserman: Oh my god. Thank you. Big warm hug for everyone. There you go. I love it.
Carly Ries: There you go. But you seem to just kinda have this networking relationship building thing innately, probably also down to a science from just years of doing it. So I wanna know for people that are kinda used to being behind their screens, what has the rise of social media platforms that you've met on LinkedIn? How has that reshaped traditional networking and community building strategies compared to the olden days?
Greg Wasserman: I mean, the olden days, if you think about it, it's we go to an event, you have the awkward, I got a name tag on me and I've gotta try and look at everyone's name and who do I gotta talk to. But it also comes down to, I don't know if it's old or just a mentality thing where it's like, what can you give me? What can you do for me mentality. Right? So you're at this place.
I gotta go meet as many people, get as many business cards as possible and and then follow-up. Right? it's kind of robotic in that way. The way I don't know if it's necessarily social media, but just the way I look at it is it's not the quantity of conversations you're having, but the quality. And as you kinda said, I believe life is about time relationships.
You have no clue where one conversation is gonna go. So if I go into place with the mentality of, like, I'm strategic, I've gotta talk to this person, There's value to that. you kind of understand who you need to talk to but you don't know talking to the guy at the water cooler, who's standing alone with that guy. He could just be an introvert and go like, you know what? I'm gonna go talk to this person and have that.
That same exact thing as online. Maybe a person's not incredibly active on social. Maybe they're not incredibly active on LinkedIn, but, have the conversations. Reach out to them. They'd be like, oh my god.
That's so nice that you did this. I think there's a huge change for social that allows a person to, a, come out of their shell, b, not be so strategic but just think about conversations in a way like I don't know where, but you seem like someone I would wanna talk to. And then when you create a really good profile, I think as you said, like my profile, you're like, I just wanna talk to this person. I just wanna know more. So if you have a profile, you put yourself out there, it's the authentic you as opposed to not knowing anything, Now you're able to create that connection.
Now you're able to go and say, I want to learn more. I want to talk to this person. And I don't know where this conversation is gonna go, but, you just seem like someone I wanna talk to.
Joe Rando: Can I ask you a question? So Yeah. There are people like you and Carly that are ease on the Myers Briggs scale, and then there are people like me that are solid I, and there's a lot of us. And so you go to a networking event, some in person event, and you don't know anybody, and you see these crowds of people all talking together because they've been, there last year and the year before, the year before, and they go they know each other from somewhere else, and you're all alone. Any suggestions for how to manage that and not just stand in the corner and look at your iPhone?
Greg Wasserman: I mean, I guess the biggest thing is you have to take the initiative and go up and talk to someone and join the group. But part of it is just joining a group and ask a question or just sit there and listen. Be awkward. Like, at the end of the day, we're all awkward. I'm an extrovert and I'm still gonna be the awkward person who's like, feeling like you, I don't know anyone here, it's just like, you know what?
What do I have to lose? Like, that's literally the mentality. What do I have to lose? I came to this event for a reason. So if I sit here and did nothing and talk to no one, what was the point of me actually coming in the first place?
So getting that little courage, which I think goes to a lot of other things that we can talk about, but, consistency. Right? Like, if you are an I, I'm not gonna change that. But, in reality, introverts are like, I get fed from an energy standpoint by being alone. Extroverts, I'm like, I need people that will feed me. But that doesn't mean as an introvert, you can't engage and have conversations. It just means I need to back away after this because it was just so much for me. So just flexing that consistency muscle of like, I'm gonna go to this event. I'm gonna at least talk to one person.
I'm gonna join one group. And you just keep doing that. And that's no different than doing it on social media where it's like, I need to practice this. I just need to keep doing this. I remember I had a leader for a company I was with.
He's like Greg, I hate people. If I had my way, I would just do my own thing. I'm like well, you're kind of the president of a major company here. How do you do it? And he's like, because I like money more.
So I realized I have to push past the discomfort of what may not feel right to do it. And I think that's another thing, pushing past discomfort whether you're starting your own business, whether you're an introvert going to a network event, you always have to push past some form of discomfort.
Joe Rando: But I just wanna say, I like people. I don't wanna be lumped in with that guy. I like people. just it's hard. one of my strategies has been to find somebody that looks more uncomfortable than I am and then act like I'm the welcoming committee.
And, weirdly, I've met some people that really weren't a good use of time, but I've also met some really amazing people with that. And it works for me as an introvert.
Carly Ries: I think another thing is to embrace the awkwardness. I was actually at a holiday party. At the time of this recording, it's early December. And I was at a holiday party, and a person was wearing a shirt that says, I'm here alone. Who wants to chat?
And it was just like, well played, sir, because everybody went up. I was like, let's chat. It was just like, you know what? I'm showing up by myself. I'm uncomfortable.
Let's just put it on display.
Joe Rando: Now was this a T shirt or a dress shirt?
Carly Ries: A T shirt.
Joe Rando: So it wasn't a formal holiday party.
Carly Ries: It was supposed to be cocktail attire, but this guy was kinda like, you know what? I'm putting myself out there. I don't care. And that in itself was just embrace it. like you were saying, Greg, even the most, extroverted people like us, it's not easy to go up to somebody and say, hey.
How about that game? Right.
Joe Rando: Yeah. I want that guy on the podcast, Carly. I think he should be on the podcast.
Carly Ries: I'll see if I can punch him now. Sounds like a plan. Well, Greg, I kinda wanna focus back a little bit for online because people do network in person, but a lot of networking does happen online. like I said, we've met on LinkedIn. You have a lot of connections, on LinkedIn.
You have a lot of people that follow you. So for people tuning in and when I say community here, I don't really mean, like, an official, Facebook community, but just an online community. What are some key elements to building and maintaining an engaged online community? You talked about authenticity. What else do people need to do?
Greg Wasserman: Consistency is king. Like, being able to consistently post content. So, most people will click on your LinkedIn profile and go like, who's Joe?
Who's Carly? Like, who is this person? If I come on your profile and there's nothing there, and you just basically, theoretically have a resume of companies you've worked at, like, why do I wanna talk to this person? Right? Or if they see consistently posting content, it doesn't have to be the greatest.
What LinkedIn algorithm is like, alright. I could post a couple times. I can engage or comment with people. Like, you are building a know, like, and trust of who you are because you're taking those actions. And it takes block off, you know, thirty minutes a day, thirty minutes a week if you wanna just start from a starting standpoint, but, post consistently out there.
And if you're, like, what do I post on? Then great. Let's at least start with just comments. Find your people. Find who it is that you want, you'd wanna follow or who it is that's in your industry.
They're like, great. These are people that I wanna surround myself with. and start engaging. I literally, what was it, this week? I think yeah.
It was this week. One of my LinkedIn posts was I commented on someone's post because I'm like, I think these people or I think a person should see what this person posted. Thought nothing of it. I'm just like, great. Next thing you know, weeks, months later, small world, they ended up on each other's podcast.
They posted about, hey. Thank you, Greg, for bringing us together. I'm like, I would never have known about that. So, your interactions, you don't know where those are gonna take and that's why you create this community, that trickle effect. So all you have to do is just start somewhere.
And consistently posting is one thing. Consistently commenting and engaging is another thing.
Carly Ries: Okay. But here's the thing. So I don't wanna make it sound like we're so popular. popular has been another wicked song that has been stuck in my head, Joe, but that's another conversation.
Greg Wasserman: Oh, that's a good song.
Carly Ries: Well, poor Joe has had to deal with my wicked soundtrack for the past week. But not to be like, oh, we're so popular. people reach out to us all the time in our messages, and I ignore 90% of them because it just seems so fluffy and so I'm gonna reach out to you because in the end of this, I want something out of it. You, though, stood out to us. We're like, we'll chat with this guy.
What is your secret sauce to standing out amongst all the people that you could tell they're in it for something else rather than just to genuinely build a relationship.
Greg Wasserman: I guess my profile literally sells life is about time and relationships. I stand out because that's truly it. I'm not gonna be everyone's cup of tea. Like, I've been told, you're still a salesperson? Like, yes.
I'm a revenue person, but, I don't have the intention on trying to sell you on a connection. I don't know where this conversation's gonna go. That's literally my line is, you don't know where a conversation's gonna take you, so have it. So if this leads to a sale, great. If this leads to a business opportunity, great.
If this just leads to a connection of two humans coming together having a conversation, you don't know where that's gonna go, but you know it's gotta go somewhere based on whatever interest, whatever commonalities, just humane, then you go with that. Most people that are probably reaching out is like your canned kind of a, I see you work in this. I also do this. We should talk type deal. Or I see we have a similar person in common.
And you're like, and so? So, it feels icky if you want that. You know, the approach I've taken and it's not everyone's cup of tea. I've had people that come back to me and said, what are you selling? And I'm like, great.
At least you engaged. That's the key thing is a comment and go, look. I'm really not selling anything. But now I've got more than 300 characters to create a narrative as opposed to the initial LinkedIn message where I've only got 300 characters. I know statistically they've shown that people who don't put a message in there get a higher response rate in terms of acceptance.
For me, I don't care about the higher acceptance rate. I want actually the engagement. And I tell everyone, look, if you sent me a connection request, you didn't have an actual message, why? So I'm gonna always respond going, I like to make LinkedIn more personal than just connections or followers. Otherwise, how do I create the dots and connect people?
And that's the way I look at it.
Joe Rando: Greg, let me ask you. So you're saying when you reach out to people, you're sending them a connection request, and you've got that initial few characters. But you're saying that people that don't use that add a personal note have a higher acceptance rate?
Greg Wasserman: Yeah. Statistically, they've shown that people will accept at a higher rate, which is odd because I'm like, why? But then you also have to think, how many people are using, and we're talking about LinkedIn. So how people are using LinkedIn on their mobile phone.
Most people don't take the extra effort to click the three little dots, go send a personalized message. They just hit connect. Right? So most people already have the psychology of alright, you're just adding me from your phone. I'll take the extra step and go like, no.
I got 300 characters to tell you why am I reaching out. and let's say I reached out to you and two months later you accept it. I don't know why I reached out to you two months ago. Right? So it's also for me, it's a track record of, like, why am I reaching out to this person besides just, hey.
We should talk.
Joe Rando: Yep. I mean, that's why it's important if you're gonna be reaching out and using the effort in finding people that are actually on LinkedIn. If they're actually posting, then you know that they're probably gonna see your request before three months goes by. But I wanna ask a question on this because I love what you're saying.
I just love what you're saying. But one of the things that I see is this, you know, bowing to the algorithm behavior. Oh, I have to comment on 30 posts every morning between 08:30 and 09:30, and they don't say anything. I just wonder if you could kinda riff on this concept of playing the algorithm versus coming to what you're talking about being authentic.
Greg Wasserman: Yeah. I mean, you're always gonna have different schools of thoughts. Right? My style of sales and engagement and who I am is not, the style of maybe someone else. Take the person with the flashy car and designer clothes and everything that's not me.
I could literally put on a dress shirt just for this. Otherwise, I'd be in a hoodie right now. that's who I am. Right?
So it's what is your cup of tea? And I think that's also the value of each individual person, like, what feels comfortable to them. What feels comfortable to me is not playing the algorithms and trying to do that. But maybe someone that's so revenue focused and rah rah, like, that's it. And I've seen people that have found success in those ways. you do what feels comfortable to you. For me, that's just not my style. For me, I've got to engage and goes back to your question, Carly. Community. Right?
Like, why am I engaging with this person? Why am I actually adding value to this conversation? I'm not just doing it just for the sake of look at me.
Carly Ries: Well, so, Greg, let me ask you this. Because algorithms aside, let's say people are like, yeah. That's great. I should go and comment on people and build genuine relationships, but I have to run a business. I have to reach out to clients.
I have to work on my business. I have to work in my business. Like, where on earth am I gonna find the time to create genuine relationships through commenting? What do you say to people who are not prioritizing that, and why should they?
Greg Wasserman: That's your standard short term, short term to play in the short term and missing on the long term. Right? So if you think about it, if we just improved 1% I think what the stat is, 1% a day, by the end of the year, we're close to 38 times better than we were. But if you're only playing the today, today, today, I need sales today, I need this today, you're not gonna grow to the 38%, growth by the end of the year.
So you make the time for where you see the value. If you're like, I'm only gonna play the short term, I need sales today or I need whatever actions you need today, You're not looking at authentic relationships and that's the way I look at it.
that's literally what I say. I don't know where this conversation today is gonna take me. Five years from now, it could be like, you know what?
Carly, I remember this conversation. We should talk again. And then you see your quote, unquote ROI of that relationship. But in reality, if you just keep a conversation going, if you stay warm, if you keep them back to your community, your network, then people will know, like, and trust you. As opposed to know, like, and trust you as the person who just wants something from me or is just trying to close something from me, goes back to the thing.
I don't know where a conversation is gonna take me. So if you are open to conversations and we've proven, you know, statistically, stats right here, more conversations you have, the more likely you will get people that will help you, buy from you, help you in the long term, whatever it may be. So if you're like, I'm running a business, I don't have the time for this, you have to make the time. And that's the thing with any solopreneur.
Like, that is probably what most people are saying. I don't have the time for x and you've got to prioritize what x is. Let's take another example besides networking and relationships. I bought a product. I don't have the time to figure out how to use this product or the product.
I see this all the time. You bought a product or service. Why? Well, the product is always gonna evolve, but you've set it up. You've moved on to the next thing in your business. great. I built this CRM system, whatever it is. You always have to be in that system because the system's evolving just like your business. If you don't spend the time investing in it, you're like, I'll get to this later, get to this later, then you're always playing catch up or you're always playing the I don't have the time game. If you invest time earlier, it'll help you in the long run, which just goes back to that 38% I'm talking about.
Joe Rando: You know what this sort of reminds me of is, there's an old saying about, like, 90% of life is just showing up. And if you just show up for people, it's like an investment in your business. Right? You're working on your business so it really goes into that quadrant of working on your business. Right?
I mean, that's not what you're talking about, and that's a good way to think about it. I hadn't put in that perspective before.
Carly Ries: Well, it's funny because you guys keep saying investment. And, Greg, you then said the ROI, quote, unquote, on these connections. How do you measure the success of these relationships, as it relates back to the bottom line of your business? And, when do you cut conversations off? Because there are some people that will start a conversation with them online, and then it just kinda becomes a task to, respond to these people or they become an energy sucker.
And at what point are you like, alright. Done or reevaluate. Be like, actually, if I continue nurturing this relationship, this could work out in the long run.
Greg Wasserman: I think the latter part of your question is that's a gut feeling. Right? Like, that is going to be a feeling I've got. Like, this isn't going anywhere or let me invest my time somewhere else. I think that is gonna be what feels right to you.
But it's also then a mentality of going alright. Does this feel wrong to me? Is there discomfort in this conversation? Because I'm not actually doing the right thing in this conversation. I am a passenger in this conversation as opposed to a driver of this conversation so that I can get not the ROI, but, what else what am I missing in this?
Am I just letting this person suck me? And I'm like, hold on. Have I even turned around and asked them, hey. How can I support you? What can you support me on?
Or whatever it is. I think that's a key piece to it. I'll be honest. I don't have a formula in terms of an ROI. I just know that the more conversations I have, the way my brain works, here's another example.
Had a conversation with someone today, looked at their LinkedIn, saw we have a few people in common. Person's name I haven't seen in ages. I'm like, great. Let me go email this person. Literally emails like, I have no agenda.
I'm not trying to sell you anything. It's like, but we haven't talked in ten years. Like, where's the harm in having a connection going? Like, where is that gonna take me?
So it's just literally having those things and then next thing you know, I could have this conversation with this person and go, like, oh, Sally, you should be talking to so and so and then what's the ROI? Cost me nothing to reach out to them. Cost me nothing in that half an hour of conversations. But I don't know where those things are gonna go and that's the way you just play the trickle effect. So the ROI is building your brand so people know, like, and trust you and then the other side is, as my mentor likes to say, people know you, hon.
It's not who you know, it's who knows what you know. And so the more people I'm able to have conversations with, the more people are gonna go like, oh, you should talk to Greg because Greg knows this. So I've always gotta be thinking about how do I get my brand out there so that people know, like, and trust me, but know, like, and trust me for what? That's where the ROI comes in because when someone's like, oh, you should talk to Greg, comes out of the blue, there's your ROI that I never would have expected because people know, like, and trust me.
Carly Ries: Has your approach to relationship building changed over time? And is it getting harder the longer you're in this or easier? Or just how what does that look like?
Greg Wasserman: Easier. Goes back to your question, Joe, in terms of playing the algorithm. Technically, I know you're not supposed to be tagging a bunch of people on your your LinkedIn post. I don't care about playing the algorithm in terms of impressions and so forth. I do strategically because that keeps my network going.
That allows me to have more people seeing not my content, but what I'm trying to do to help them. I do every Monday, I do three podcasts that I think people should listen to, which I did your podcast before you rebranded it ages ago. Right? And I think that's what brought us then together again this time. So I do that because as a podcaster knowing this, like, no one's giving you feedback.
And so one of the biggest compliments you can give to someone is going like, hey. Look at what I just did. You should listen to this too. Wouldn't that be great from a business standpoint if other people are like, I just talked to Joe. His business is amazing.
You guys should be talking to Joe too. And that's their LinkedIn post. Joe's gonna feel great. Your conversation has an ROI in if you think about it from that standpoint, and conversations are able to continue. So I don't care about the algorithm.
I'm playing the let's play create connections. Good people talk to good people. Let's help other people. And when you have a give mentality, you'll end up receiving a lot more on the back end. So for me, social media, I only live in LinkedIn, has actually helped me over time because as my network grows, as my brain matures in terms of who the conversations I've had, I'm able to connect more people, create those social changes, create more connections that others find value which then helps me build more of a brand.
So once again, it's playing the long game. Five years ago, while mentality was the same, I've now been able to refine it going like this is what brand Greg is, and I can put it all out there as opposed to this is who I was, but no one understood what I was trying to accomplish. Now I can do that even so, to a higher degree.
Joe Rando: Yeah. That's really important, being clear about what you're about. Yeah. Cool.
Carly Ries: Well, Greg, just to tie everything together, if you could offer one piece of advice for someone trying to shrink strengthen their network, whether online or in person, what would that one piece of advice be?
Greg Wasserman: First, consistently do it. Like, if you are consistent, as Joe said, just showing up, success is just showing up. Right? So if you just have to show up, whether it's in person to events, those are all, if we go back, investments in yourself. literally I got an invite to an event and I'm like, do I go to this? what is the value and what I'm like, I don't know. I know I've been to another one of their events. I'm just gonna go to it and say, hey. This is it.
And you've got the trade off you have to make. Like, is it time value? I always look at it as I don't know what it's gonna take. If I say yes to things, usually it ends up working because as you said as well, Joe, I'm putting it out there and the universe, I believe, is going to give me what I'm asking for because I'm just saying yes and putting it out there. So consistently, just do it.
Carly Ries: Love it. Well, you help people find success through building relationships. We ask all of our guests this question. What is your favorite quote about success?
Greg Wasserman: I'm from Chicago. So for me, I'd have to go with Michael Jordan's success. I will butcher it, but basically, he's missed so many shots. He's been given the game winning opportunity.
He missed it. He took all these shots and missed, but at the end of the day, it's the failures he had that allowed him to have success. that's basically the key thing. So once again, being consistent.
Continue to show up. Continue to just take the reps, and the more reps you take, the more success you'll find.
Joe Rando: Wasn't it Michael Jordan that said I miss a 100% of the shots I don't take?
Carly Ries: That's what I was thinking.
Greg Wasserman: I don't know. I mean, there's a much longer quote.
Joe Rando: Somebody tell us in the comments.
Carly Ries: That's the quote I thought you were gonna say when you said Michael Jordan. I think that he said that. But, yes, leave comments for sure.
Greg Wasserman: I always remember growing up, the t shirt, and it's like I took 8,000 shots. I took 24 game winning shots and missed and so forth. And at the end of the day, that's why I succeed.
Joe Rando: Yep. Great. I just watched the movie, by the way, about Nike signing him back in the eighties.
Greg Wasserman: Oh, that was a good movie.
Joe Rando: Yeah. It was really interesting.
Carly Ries: For sure. Well, Greg, where can people find out more about you if they want to connect, but anything else?
Greg Wasserman: I live on LinkedIn. That is the best way. So reach out to me on LinkedIn. As I said earlier, add a comment.
Let me know that you listened to me on this podcast. And then I can let Joe and Carly know, like, hey. Look at this great thing because that provides a feedback loop that everyone's looking for. So, Greg Wasserman, you won't miss it. A, the face, but, b, it says life is about time and relationships.
Carly Ries: And we'll include the link in the show notes as well. But, Greg, thank you so much for coming on the show today. We were really looking forward to it, and you do not disappoint.
Greg Wasserman: Thank you guys so much for having me.
Joe Rando: Thank you, Greg.
Carly Ries: And listeners, as always, we love that five star review. We love the subscription on any of your favorite platforms, including YouTube. We just so appreciate the support, and we'll see you next time on the Aspiring Solopreneur. You may be going solo in business, but that doesn't mean you're alone. In fact, millions of people are in your shoes, running a one person business and figuring it out as they go.
So why not connect with them and learn from each other's successes and failures? At LifeStarr, we're creating a one person business community where you can go to meet and get advice from other solopreneurs. Be sure to join in on the conversations at community.lifestarr.com.
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