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EPISODE 6: The CEO Whisperer (w/ Executive Coach Jason Gore) πŸŽ™

EPISODE 6: The CEO Whisperer (w/ Executive Coach Jason Gore) πŸŽ™

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Jason Gore knows a few things about change. As an executive coach, he’s guided executives in startupland through recessions, booms, the burst of the first dot com bubble, and most recently, a pandemic.

This week Jason joins Louis to talk about the challenges facing CEOs right now, how they’ve changed and how β€” in many ways β€” they’re the same.

“I see a lot of co-founders that don’t give each other negative feedback. But if you don’t have those conversations, things come to a head and then it’s too late.”

-Jason Gore

πŸŽ™ Highlights Include

  • Jason’s path from management consultant to executive coach
  • The tricky relationship between VCs, coaches & CEOs
  • The upsides (& downsides) of the co-founder relationship, and how to create space for disagreement 
  • The biggest issues facing many of today’s startup CEOs 

This Week’s Guest

Jason Gore headshot

Jason Gore

Managing Partner & Executive Coach @ Neuberg Gore

Jason Gore is half of the founding team of Neuberg, Gore & Associates, an executive coaching firm that supports startup CEOs in Boulder, SF, NYC and LA.

The Startup Stack’s Host
This image has an empty alt attribute; its file name is louis-1024x1002.png

Louis Beryl

CEO, Co-Founder of Rocketplace

Rocketplace is a curated marketplace of high quality professional service providers. A 3x founder, investor, and board member, Louis began his tech career as a partner at Andreessen Horowitz. When he’s not working or podcasting, Louis enjoys cooking for his family. His pizza, he’d like you to know, is incredible. 

Full Episode Transcript

Jason Gore: Sometimes I feel like a high priced babysitter.

Louis Beryl: Exactly!

Jason Gore: The biggest joke is human nature.

Louis Beryl: Keeps you in business.

Jason Gore: It does.

Louis Beryl: Hello and welcome to “The Startup Stack”. I’m your host, Louis Beryl. And this week we’re talking to Jason Gore, founder of Neuberg Gore. Jason is an executive coach and an entrepreneur. Full transparency my co-founder Ben and I have worked with Jason and his partner Brian for years as our coaches. He’s also someone with unparalleled insight on what exactly VCs and CEOs are thinking and fearing and asking for help with right now. We covered a lot of ground. So here’s Jason.

Louis Beryl: Well, you know, I wanted to start off today and ask you really about how you came into coaching. You know, where were you born into this? When did you know that, you know, this was the career for you? How did you become a coach? Let’s start there.

Jason Gore: Well, I really knew I wanted to go into business because I liked working with teams that had a vision that wanted to work and collaborate together. But things really clicked for me coming out of undergrad. And I went into undergrad to look at persuasion and debate how people learned and resolved issues together. After school, I joined a consulting firm working with the Department of Defense and my very first assignment was with a nuclear power plant and I was 21, I was paired with a nuclear sub captain and we were basically going to look at how…

Louis Beryl: Where are you underwater?

Jason Gore: No! It was above water. We weren’t actually allowed on the plant though. We would meet in these little rooms right about 2 miles away. But so I showed up and I got a call and basically my partner that was supposed to be asking all the questions and doing all the interviews, calls in sick that day. It turns out it’s really hard to arrange these interviews. And so the partner in charge at my consulting firm said, you got to have these interviews. And I’m like, look, I don’t know anything about nuclear power plants. How am I supposed to interview nuclear power plant engineers? Like, this is ridiculous. And he basically said, hey, just ask open ended questions, paraphrase what you’re hearing and really just talk to them as human beings. Like find out what their issues are in layman’s terms. Don’t try to pretend anything. So I interview the first person and talk to them and very quickly learn that they simply just don’t have the parts on hand. They got a three million dollar budget for parts. And if they if a certain part breaks, they need a helicopter parts in from another plant or kind of a central repository. And so the plant stopped for a half day at a time, and that’s a lot of money. Talk to the next person kind of hearing the same story over and over again. So I basically package up what I’m hearing. I present it to the management, at this point the sub captains back. And so he does most of the presentation. And they’re like, wow, this is brilliant. If we just take a loan for two million dollars and have these parts on hand, we’re going to save like 5 million and in downtime costs. And I’m like, why do you need a 21 year old kid to talk to your engineers and tell you exactly what they told me? This makes no sense. And so my assumption actually was that it was just a lack of listening, a lack of curiosity, like something was going on. I joined the telecom space, found the same thing that in the telecom space, the same issues where information was not getting passed and problems were just not getting resolved. So I went back to business school to figure out essentially why the people in charge were bad listeners. And my assumption was that they were just kind of being in charge and promoted because they knew how to get stuff done. They knew how to push through things and kind of bully their way through execution. But in business school, what I learned was that actually wasn’t true. In fact, that the problems were worse the lower you went in the organization and that essentially people were not problem solving together. They weren’t talking to each other. They weren’t, they weren’t working well together. And there’s just a whole bunch of money left on the table.

Louis Beryl: And so so you’re seeing all these business problems and how does it click for you that coaching is the career path and the answer here?

Jason Gore: Because for me, you know…

Louis Beryl: Versus versus consulting, which is what you’re doing, which because I guess a lot of people could hear what you’re describing and be like this is why the world needs management consulting totally.

Jason Gore: Well, first thing to say is like what? I was shocked by just the role of a facilitator. Just by playing traffic cop in the conversation and getting people to listen to each other and talk to each other in a structured way that they would get so much more done. But then the question was, hey, why do you need a twenty one year old kid? Like, why can’t you do this yourselves? Right. And so so then I started to teach communication skills and leadership training and whatnot. And what I found there is that the retention was relatively low because people would learn these skills, but then they would go back into toxic environments. And so we’re coaching really came up for me. OK, this is also a cultural issue. And so if we coach executives at the top and they model behavior, then we could start to create a culture where everyone can be resolving problems together in a more effective way. And so that’s how I end up at startups as well.

Louis Beryl: Tell me a little bit. So, OK, so your career is kind of morphing from management consultant to executive coach. If you’ve been to business school, could you tell me about what was your first, like, formal executive coaching job? So someone has paid you to be an executive coach? Tell us about that first experience I had and how did you get it?

Jason Gore: Well the very…I mean it was gradual because I started the spot coaching. I started coaching executives on one negotiation or one issue. Hey, we’re having this issue. Would you come? A lot of my earlier early work was one executive was having an issue with another executive or one executive was having an issue with a vendor or supplier, and they would come bring me in as a negotiation expert or an expert in difficult conversations. And I would just coach them through that issue. And honestly, I found it once again to be really interesting because the fundamental principles were relatively easy. But the person would get lost in it because it was really important to them. They would get caught in their emotions, but they would end up going into these conversations much more confrontational versus in a collaboration set. And so a lot of these early coaching and experiences were changing people’s mindsets. And then through changing those mindsets, their behaviors would change. And a lot of the mindsets they would get stuck in were, frankly, because of their history. And so here I am we might be negotiating buying parts for a nuclear power plant. But what this person was dealing with was they were pissed off about the unfairness of something and they were angry at the other person. So we had to kind of deal with the emotional issues, too. It’s you know, people say that business is not personal but it really is. And it’s hard not to bring all of ourselves and all our history the good and the bad into our conversations. So it started that way. And then what I realized over time was people kept calling me back and saying, hey, I got another little issue. I was actually really resistant to coaching because I liked the consulting projects. I got to walk away and go and have big adventures. But over time, I really fell in love with startup entrepreneurs. With the CEOs that were thinking things out from scratch and building a culture from the ground up. And I just found myself really drawn to longer engagements and really committed to their success. And that’s where I jumped into coaching full time.

Louis Beryl: And then let’s jump to Neuberg Gore and, you know, the company founded by Brian. Tell me a little bit about how that came together. I’d be particularly interested in what were some of the really tough challenges you faced early on, starting the firm.

Jason Gore: Well, honestly, starting the firm was a very organic process, Brian Neuberg, my partner, is just a very relational person and he got overloaded with clients. And so he turned to me and started giving me clients. And then he saw that I was structuring my programs really differently than his programs. And he’s like, what are you doing? And so I shared the structures that I was using and how I was holding people accountable, how I was helping them identify their blind spots. And he started doing that with his clients and getting very different kinds of results. Like it he was doing coaching in a very different way than I was. And ultimately, we kind of blended our styles and the way that he brought the relational in the deeply personal and kind of human pieces. And I brought the blind spots and the structural pieces that were kind of the secret sauce. And what really fueled our development because we really have a very structured process but that’s a very deep process. And we hold all our coaches accountable and really do a lot of quality control so that our clients walk away having made some really big changes. But I tell you, this is how we learned some hard things along the way, especially because the startup world can be very challenging.

Louis Beryl: Jason, I was wondering if you could tell us when the right time is to hire a startup founder to hire an executive coach? I think about my own experiences working with coaches. In my experience, it seems to me that it’s always been when a couple of things are happening, certain things at the company are going really well and you’ve probably achieved product market fit. The company is growing really quickly. While at the same time there’s some pretty big challenges. Usually on the people’s side. Maybe that it’s with your own leadership. The team’s growing really fast and you’re dealing with more senior executives. Maybe there are challenges with co-founder dynamics or investors. And so what I’m wondering is, is every time you get a new client, the CEO’s hair’s on fire. When you’re first talking to them.

Jason Gore: You know, I think people have different choices of when they need an executive coach. Some people think they never need one. I can say it’s never too early, but sometimes it’s too late. But some good indicators for when you hire a more senior executive coach might be when the company is shifting. When you’re shifting from being an individual contributor to managing a team and have to shift that role or when things are shifting in the company. I mean, in general in the startup world if I were to have to put a marker of time where the cost benefit really makes a difference and really makes sense I would say after a series A funding. Where you have money in the bank, you’re going to be growing your team, you’re going to be managing some people out. You’re going to be really pushing on product market fit and scale. That you know, I would say is a nice indicator. But the other one is, as you feel like you’re basically over your head, which might be from the start, is a good time to get a thought partner.

Louis Beryl: You know, one of the things that has really made a deep impression on me, you know, when I was at Andreessen Horowitz working with the team there, Ben, one of his famous things that he kind of insights that he always talks about is that you hire for strengths, not lack of weaknesses. And I actually think about that a lot when I think about confounding relationships. And I think about it in the context of Ben and I and why it works so well. And I think one of the reasons it works so well is not because either of us are perfect, not because we don’t have lots of weaknesses. It’s actually just that we are very aware of what each other’s weaknesses are. We have accepted those weaknesses. We’re very aware of what each other’s strengths are. We want to encourage each other to go do the things that they’re good at and they like doing. And we don’t try to get each other to do the things that we’re less excited about and we’re less good at it. And that’s taken us time to figure out together. You know, we’re talking a lot about co-founders, and I imagine that you coach a lot of solo founders. How do you help executives that don’t really have that confounding relationship and don’t, you know, don’t have anyone to lean on?

Jason Gore: Well, I think that most don’t. When you look at the averages, most founders are going to go through three complete executive teams before their exit. And, you know, when you’re a seed stage company, you can’t really attract or most people can’t attract talent that is going to grow with the company. You just can’t incentivize those folks early on and can’t get them in. So, you know, you get who you can. And also, frankly, first time executives, they don’t know what a good team looks like. They don’t know how to assess or manage a CMO. And so they might get a CMO with a heck of a resume who is not performing, but they won’t necessarily know it. So, you know, it makes it hard for them to navigate that. And a lot of the work, I think in the beginning is, yes, being a thought partner and for sure helping them think through things and uplevel themselves. But what are the biggest things is helping them up along with their team.

Louis Beryl: That’s a fascinating statistic about how most companies are going to go through 3 complete executive teams on their way to exit. And I’m wondering, is that a healthy company? I mean, in some senses it must be if they’re exiting at all. But we also read in the press all the time about companies shedding executives and how, you know, usually we talk about that as a sign of a very unhealthy company. But is that just a natural, healthy process for companies to grow?

Jason Gore: I think it is. I mean, you know, some companies might get lucky where you get the corporate athletes that scale up and scale themselves up with a role. But even those folks, when you look at a functional expertise. You know, you need different things at different stages of the company. Like at seed stage you need that corporate startup athlete that can do a thousand things and figure things out and hyper creative. You know, moving into A and B, you’re looking for someone who’s done it a thousand times and has good pattern recognition and really knows, like you could throw a lot of marketing dollars aren’t working someone else comes in and like, oh, while you’re doing it wrong, you’re spending your marketing dollars wrong. And they just change a few things and all of a sudden that dollar in becomes three dollars out versus what you were having. And then later on, you know, moving into B > C, you know, and I’m just making broad generalizations here. But you need someone that has a Rolodex and knows how to build a team. Right. They need to build out not only a team of 3 or 4, but they have to run a team of 30 or 40. And that’s oftentimes different people. Some people can scale. But from what I’ve seen the vast majority of times we’re actually looking at people that are drawn to different stages. And they have different strengths that apply at those different stages. This is a good reason not to give up titles too early. You know, you give that CMO position out early on. It actually does accelerate that process of having to change people out, because then when you want that person to move, someone else will only come in, you know, with a certain title. It’s really hard. So in the beginning, I was always advised as head of it to allow that flexibility.

Louis Beryl: This is certainly a problem I’ve struggled with. And, you know, if I was going to rearticulate what you said or rearticulate how I imagine this scenario playing out. You know, you’ve started a company, you hired people that are good athletes. The company has found a product market fit. You’re starting to grow. Everyone feels pretty good. You’re probably friends with all these people. But now we need to do different things as the company is growing and scaling potentially some of those executives or different leaders on the team we need to up level. But that must be tremendously challenging. I personally have been through these challenges. Of, you know, how we transition to different leaders that we need in the organization away from other people that we’ve really worked with. And we’ve gotten to that place and we’ve trusted I mean, how do you coach people through that?

Jason Gore: Yeah, you know, I think the first thing is to support them and have conversations. You know, so many times things get to come to a head and people are surprised. I see a lot of co-founders that don’t give each other negative feedback. And don’t call out, hey, the way that you’re filling your role is not working. The CTO who’s really amazing and hyper creative and really gets the high end but is not managing their team. And all sorts of cultural problems are arising. Like, let’s have that conversation. You know, if you really like the person and you want to keep them on, then simply hire the expertise around them. Like in the CTO example. You hire a VP of engineering to run the team and you let the CTO be creative and do what they do best. But if you don’t have those conversations, things come to a head and then oftentimes it’s too late that there’s too much resentment, too much built up tension. And so I would encourage people to have the conversations early and really explore. I think the other thing to say is, you know, consensus driven models and in 50/50 splits are scary. I much prefer a 51/49 split where there actually is clear control. I mean, just recently I had two co-founders that were arguing and had completely different visions of the company and their lead investor was like, hey, we can’t get involved here. Like, we can’t take sides. You guys have to figure this out. And one of them was gracious enough to step down but they could have taken the company to the ground with that fight. And so, you know, finding business partners that you agree with, having a really clear decision model and also really clear conversations about, you know, when someone steps into the CEO, do they have the right to fire their co-founders? And if you have the conversation earlier, it’s going to really clarify problems and it’s also going to make the company perform better.

Louis Beryl: You know, this is fascinating talking about executive transition co-founder issues. I’m wondering if there’s other very common pain points that you see as an executive coach that we could chat about.

Jason Gore: Tons! I mean I mean, I think the biggest one is especially for younger generation CEOs. They want to be friends. They want to be peers. They generally are conflict averse in general. Big generalization. And they don’t like giving feedback. And so they generalize feedback.

Louis Beryl: And if I think about, you know, notable CEOs that don’t seem conflict avoidant like Travis from Uber. Or, we don’t even have to keep going. But it’s like, and it doesn’t feel like the world has shown particularly favorable to those types of CEOs. So, what’s the right balance?

Jason Gore: You know, here’s my answer to that. It’s soft on the person, hard of the problem. This is really a negotiation technique that came out of the book “Getting To Yes”. And it’s like you could be really hard on the problem and really kind to the person. You know, even if it’s to the point where I want to see you up level, I want to see you succeed here and you’re not. Right now you’re not fulfilling the duties of this role as I need them. How do we get you there? When do we know? And if you don’t get there, what are we going to do about it? Like, those are scary conversations. And, you know, you look at having that conversation with your technical lead who you can’t afford to lose. And so you tend to soft pedal and that tends to be more costly in the long run.

Louis Beryl: But I’d love to bring this back to Neuberg Gore. Right. So how have you thought about holding your other team members accountable as you’ve grown? And actually specifically, I would love to understand, like, how do you measure success at your firm? Like at a firm level, at a partner level, on an engagement level. Like when you’re working with the founder. How do you measure success? What do you think about that?

Jason Gore: Well, I think Neuberg Gore is a very different kind of company because we are not money or growth oriented. We are a small lifestyle firm to be honest. This is a firm I’m going to have forever. This is my retirement plan. I expect to be coaching CEOs forever. Whether it’s from my home or on a sailboat from the Bahamas. Who knows? Right. So for us, honestly. Like brand reputation is the most important thing, right? This is a company that I want to have and hold for a long time. It’s dear to my heart. And that means client success. That we want to see our clients extremely happy and grateful for the coaching. And it’s very valuable to them. These are very busy people. And if they’re not extracting value from that not only the money but the time is even more important. Then we got to know about it. And so we have really a lot of quality control. Every few months we have a second coach talking to all of our clients to make sure that it’s optimized and if they’re not happy shifting it or even changing our coaches. But also the external changes. We’re not just counting on the CEO to give that internal report. We’re looking externally and getting progress reports. Where, hey, this is the thing that the client is trying to change. How are they doing? Do you see growth? Is more growth needed? Right. And really trying to get the people around them to give direct feedback. And when we see growth, then the clients are happy, the people around them happy, and the company is going to be higher performing. You know, I think one of the things that is really important to us is we really are picky about who we take. And we want to enjoy the coaching relationship as well. We want to be with growth oriented folks that have high ethics. And so we’ll turn a lot of clients away, especially if they’re coming in as a board member calls up and says, hey, the CEO needs coaching but doesn’t want it. The answer is that’s not us. That’s not that’s not how we operate.

Louis Beryl: Yeah, I was going to ask what makes a good client? And is the answer as simple as they want coaching?

Jason Gore: I think it’s more to it than that. You know, we have a lot of clients who say they want to. Whether they get into it and they don’t show up. You know, it’s like they actually have to show up for coaching. Not as a passive participant on the train. They’re in the driver’s seat. They’re coming to the meeting with agendas. They’re proactive about getting the most out of a coaching relationship. That’s what we’re looking for. Right. Is people that are not only willing to grow, but are proactively focusing on growing. And plus ethics and other factors that play out.

Louis Beryl: You know, I’d love to transition the conversation into some trends you’re seeing. It feels like now more than ever the world is really changing quickly. We’ve got COVID. We’ve got an increased awareness of racial inequality. And I’m wondering what but also just technology companies and just how they’re so rapidly changing our landscape. What are you seeing today that’s different right now than it was 6 or 12 months ago? What about like how is the world different than it was 20 years ago and how and how do you coach?

Jason Gore: Well, you know, 20 years ago, people didn’t know what coaching was, right. So we had to educate clients about what coaching was. Nowadays, when people come to us, they’re not trying to find out what coaching is. They’re trying to pick a coach they already know they want to coach. And now they’re just comparing between different coaches. And by the way, on that note, I would say chemistry and trust are the biggest factors. Right. If those aren’t there, then I don’t care what kind of resume someone has. It doesn’t matter. Right. You have to be able to really have chemistry and fit. I think there’s something you didn’t say is the VC markets have also changed. Right. In the expectations and growth expectations are changing. And that’s one of the big things with COVID that’s really shifted things. Is the expectation around what things look like and how much money you could spend and how much runway you have. Right now everybody’s expected to do more with less. One of the things that we had to figure out as a coaching firm was who is our client? Right. The VC referred us to the CEO. Is the CEO our client? Is the company our client? Is the VC our client? The answer is so clear it’s the CEO. I re-educate the VCs on the beginning of every single phone call. I basically say, hey, I really love talking with you here. Everything you say to me, I’m going to tell the CEO. Don’t tell me anything that you don’t want the CEO to hear.

Louis Beryl: I love I love that!

Jason Gore: 90 percent of the time they say, hey, I’ve already told the CEO everything I want to tell them anyway. So all you’re going to do is help me articulate this and clarify it and have a second point of contact. You know, the place that’s even trickier though I’ll say, is when we’re dealing with co-founders. Right. One coach is coaching the CEO and let’s say the CMO. The one place that we get into trouble is if the CEO is going to fire the CMO. We tell the CEO, don’t tell us if you tell us that we’re going to fire the CMO. We will put ourselves on leave of absence until you resolve it. Right. Because what we can’t do is we can’t be hiding secrets from each other. Now, if you’re disappointed in this person, we will support you in having that conversation directly. But if you put us into a position where we have to hold secrets from another client, then we have to stop. And so all of that is specified in advance. And I have to say, these are lessons that are hard won.

Louis Beryl: If you could go back in time and give the young Jason Gore some advice, what would be the one or two pieces of advice that you would give yourself? Cause you actually couldn’t even instill all this knowledge because it was hard won?

Jason Gore: Well, I feel really lucky, Louis. I have a job I love. I have clients that I really respect and appreciate. And I feel very lucky to be where I am. Even through this whole hook COVID time, I work out of my house. I live in Boulder, Colorado. I get to travel wherever I want and work from really anywhere in the Americas. I have a great team of literally all the clients at the firm are amazing. So I feel very fortunate. I will say that it’s been a long haul, that there is no coaching industry. There is no track. And if I was telling the young Jason about this. I would be like, you better really want this, because it’s not an easy path, but I really did.

Louis Beryl: People often ask me my advice about starting a company, and I give very similar advice where I say, if you’re thinking about starting a company, when you come up with an idea, I want you to then ask yourself, if this is the last job you ever have for your whole life, for the next 20, 30, 40, 50 years. Are you really excited about that? That’s how excited you need to be about this company. That’s the bar forever!

Jason Gore: One thing I love about this is I grow so much. You know. Just this morning I was giving advice to someone who was absolutely overwhelmed. And I’m overwhelmed running two companies right now. And, you know, the advice I was giving him as I was giving him, like, hey, I want to let you know, like, I need to live this, too, and, you know, outing myself at the same time and, you know, making some real big commitments for myself right now. So, you know, as we were talking, I’m like, hey, I’m going to give up alcohol in the evenings and I’m going to start waking up at 6:00 in the morning every morning. And I’m going to start building my own routines because in the last two weeks, I’ve lost those routines. So it really keeps me on my toes as well. I’ll say that.

Louis Beryl: You give advice all the time, and it sounds like sometimes you also try to follow your own advice. What’s the piece of advice that you give all the time that’s the hardest for you to follow?

Jason Gore: You know, right now I am a new company. I haven’t built a team, and so I’m in the weeds and doing a lot. And it’s it’s really, really challenging time because I’m doing that and I’m also running a more mature company at the same time. And I would say if I was coaching myself. That I would be telling myself that I’ve signed up for an impossible task. That I need to hire an operator for one of the companies. And right now I’m in an interesting financial position because neither company really has a need for a full time operator. But I have my head in the sand a little bit where I’m going to end up burning myself out if I don’t change something on one of these two companies. So I’m keeping a pretty careful eye on that. And I’m essentially going to slow with the new start up company down and basically deliver…I’m going to slow the road map down by about 50 percent to try to accommodate that. Especially with all the things that are changing. But I do want to go back to something, you know, about talking to younger coaches, and that is to know your swim lane. Like, figure out what you’re good at, what you can leverage, what area you already know. And to start coaching inside of that area where you’re living, that advice, you know, that advice. You’re not just making it up. And then extend it to others from a little bit more slowly. I think some of the best coaches come out of  industry. You know, they come from the marketing or the sales background. And then you start by, if you’re in sales, coaching other sales executives. Right. And then from there, you branch into marketing and then from there you branch out. But to really be clear about your offering and what it is that you’re really good at. And I think, as you’re saying earlier, looks like something that you love, something that you really love doing. So it’s a hard role, but I love it. I absolutely love it.

Louis Beryl: Jason, this is awesome. You’re a great friend. I loved this session and this interview. Thank you so much for being on “The Startup Stack” today.

Louis Beryl: You can’t leave this without talking about your experience with coaching. Like you, you got coaching from my business partner.

Louis Beryl: My answer to that question and more on this week’s bonus episode. It’s up now if you want to listen to more more on Jason and the coaching business he’s built, head to And while you’re there, go ahead and subscribe. Thanks again next week.

Announcer: The Startup Stack. Written and edited by Hannah Levy, produced by Leah Jackson. 

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