Crossing the Axis · 2026-06-28 · 52 min
Key moments - from our scoring
Substance score
65 / 100
Five dimensions, 20 points each
Chris Whitten brings a unique perspective from having worked as a freelancer, agency producer, and now as a client-side executive producer at a brand partnerships company. The episode tackles a fundamental gap in how photographers, directors, and creative professionals approach business development: most outreach is poorly researched, impersonal, and self-focused. Whitten shares concrete strategies for getting noticed, emphasizing that effective outreach avoids obvious statements (don't introduce yourself as a photographer to someone who hires photographers), instead finding genuine commonality - shared locations, similar challenges, or appreciated work. He stresses the importance of follow-up as a rhythm rather than desperation, with multiple touches over weeks or months that introduce new topics rather than reselling the same pitch. A key insight from Blair Enns' "Win Without Pitching" frames the sales interaction as a sample of future collaboration - weak outreach signals weak work partnerships. Whitten argues that in high-value creative services (typically $100K+ projects), buying decisions aren't purely transactional; they're deeply personal because producers and directors will spend months and on-set days together with their partners.
Genuine research-based compliments about recent work, shared commonality (locations, challenges, mutual interests), and avoiding obvious self-introductions that waste space. He responds when someone shows they've actually looked at his work and found something specific to appreciate.
Wait about two weeks, then send a second, unrelated touch (a different compliment or insight). You may need multiple touches - sometimes 50+ over a year - but each should introduce new content rather than repeat the original pitch.
High-value projects ($100K+) involve multiple stakeholders and months of close collaboration, often with full days on set together. The decision to hire isn't purely transactional; buyers need to trust they'll enjoy working with the person, making relationship foundation critical.
Generic statements like 'I'm a photographer that shoots X' waste space and come across as redundant to someone who explicitly hires people in your role. They signal you haven't done research or personalized your approach, making you indistinguishable from low-effort mass outreach.
Avoid saying 'I'm sure you're busy' or apologizing for their silence. Instead, send a fresh, unrelated engagement - a new compliment or observation - that gives them a natural opening to respond without feeling defensive.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode delivers solid, practical guidance on business development and relationship-building grounded in Chris's real experience across freelance, agency, and client-side roles. However, much of the core advice - personalized outreach, follow-up discipline, content creation, listening in meetings - is well-established best practice in B2B sales circles. The insight density is bolstered by specific tactical details (e.g., the 56-touch example, the four levels of client value), but padded by repetition and extended anecdotes that don't add new conceptual weight. A B2B operator familiar with consultative sales frameworks will recognize most claims.
The sale is a sample of the engagement to follow. And so if you do a weak, tired, effortless sales approach, people subconsciously, maybe even consciously think, oh, uh, working with you is going to be the same level of effort.
What we're trying to sell is they're just trying to sell themselves. So basically you need to be cool and be someone that's fun to be around, someone that's easy to work with.
Chris articulates a human-centered, relationship-first approach to BD that contrasts with pure transactional sales logic, and the garden hobby and real estate brisket examples add some personality. However, the core frameworks - personal branding, content as visibility, consultative listening, the four-level value ladder - are standard in modern B2B thought. The newsletter-as-waterfall concept and the explicit rejection of unsolicited creative pitches are sensible but not counterintuitive. There is limited first-principles argumentation or contrarian positioning.
Basically you need to be cool and be someone that's fun to be around, someone that's easy to work with... there's a ton of people in the market right now that have really excellent work. And so then you have to level up the other part.
Let's say you're a photographer and you shoot cars... and you post, you create a newsletter around that and how. And like, what you're doing... It's gonna take off because they're gonna see your stuff and be like, I want to work with them.
Chris Whitten is a genuinely qualified operator with direct, multi-angle experience: freelance shooter, agency producer, and now client-side executive producer hiring partners. He also actively coaches others. This is not a career podcast guest or pure theorist; he has skin in the game and real decision-making authority. His perspective is earned and current. However, he is not at the C-suite or mega-enterprise scale, and the episode lacks diversity of viewpoints - it's essentially a one-guest, host-and-guest chat, limiting depth through challenge or counterpoint.
He's been a freelancer trying to win work. He's worked on the agency side hiring creative partners, and now he's client side as an executive producer, working in brand partnerships. On top of that, he coaches photographers, directors, producers, and other creative professionals on how to build better relationships.
I was producing that stuff early on around 2008... then went agency side... and now on the client side.
Chris provides concrete examples (the 56-touch persistence story, the architecture photographer he coached, the Heineken bottle anecdote, the $100k budget scenario), specific job titles and roles (XYZ Agency, automakers, brand partnerships), and named frameworks (the four levels, the Challenger Sale, content waterfall). However, most examples lack quantified outcomes, timelines are vague ("a year"), and there are few hard metrics. The financial advice (return on investment for newsletters, coaching time) is intuitive but not backed by data. Names like Blair Enns and Jenny Plant appear but lack supporting context or evidence of their claims.
I know this guy, he did 56 touches before he got a response and then he ultimately got a job from him... I think it was like a year.
a client would come and they would have just, for example, $100,000 budget for marketing... I'm going to give you 20 grand back or 50 grand back. I can do, I can make what you need.
Host James Kebles asks sharp, structured questions that push Chris to elaborate and clarify - e.g., clarifying what constitutes good post-conversation engagement, probing the date-like nature of client relationships, asking about failure cases. He also introduces his own frameworks and gently challenges Chris (e.g., "I oftentimes think it's all about the work and the value..."), creating productive friction. However, there is limited willingness to push back hard on Chris's claims, few moments of genuine disagreement or skepticism, and the conversation stays largely in agreement. Follow-ups are generally competent but rarely incisive enough to expose weak thinking.
You don't need to set it up... You don't need to tell me, hey, blah, blah, like so don't even bring that up.
It's exactly like dating... the biggest thing is being able to share a creative outlet... If you had a good conversation, I should know, Chris, what your KPIs or OKRs or whatever it is that you have to meet to, like, how is your job being measured for success?
Computed from the transcript - who did the talking, and the words that came up most.
Everyone talks about being “top of mind.” Very few people can explain how it actually happens. Chris Whitten has seen this challenge from every angle. He’s been a freelancer looking for work, an agency producer hiring creative partners, and now an executive producer working on brand partnerships. Along the way, he’s watched thousands of photographers, directors, producers, and creative professionals try to get his attention. Some succeed. Most don’t. In this Client-Side Conversation, Chris shares what actually works when you’re trying to build relationships, earn trust, and create opportunities with decision-makers. We explore how to stay visible without becoming self-promotional, what separates effective outreach from forgettable outreach, how to have a productive first conversation, and what people can do after that conversation to remain relevant when opportunities arise. Along the way, Chris shares examples from both sides of the table, including lessons learned as a freelancer, agency producer, coach, and brand-side executive.
Transcribed and scored by The B2B Podcast Index.
Speaker A: You're listening to Crossing the Axis, the podcast that explores the commercial side of film production with your host, James Kebles.
Speaker B: Welcome, listeners, and thank you for tuning in to the show. Today we're talking about something everybody in business development says they want to do, but very few people can explain how to do it well, and that is staying top of mind. That phrase gets thrown around constantly. Stay visible, keep in touch, build the relationship, nurture the lead. Yes, these are all true, but also not very helpful if you don't know what any of that actually looks like in practice. But because staying top of mind does not start with the, uh, follow up, checking in email or some kind of happy birthday message, it should be much more than that. And it actually starts earlier than that. Like how you earn someone's attention in the first place and then how it moves into an actual conversation. And after that conversation is when the work of staying top of mind really begins by things like staying relevant, using your expertise to create value, and, and developing the relationship without becoming annoying. That's why I'm excited for today's client conversation with Chris Whitten. Chris has seen business development from just about every angle. He's been a freelancer trying to win work. He's worked on the agency side hiring creative partners, and now he's client side as an executive producer, working in brand partnerships. On top of that, he coaches photographers, directors, producers, and other creative professionals on how to build better relationships, create better outreach, and ultimately find better opportunities. I've found that Chris brings a generous, sharp, and very human point of view to this topic and that he believes relationships are built over time and that outreach should be about the person receiving it and that helping people is not just a nice thing to do, it's actually a real business strategy. So with that, Chris Whitten, welcome to Crossing the Axis.
Speaker C: James, thank you so much. That intro was awesome. Thanks for that.
Speaker B: I did. Did I characterize you correctly?
Speaker C: I think so, yeah.
Speaker B: Anything I missed or any omissions or, uh, problems?
Speaker C: No, no, it's all good. I think we'll dive in, into the interview and maybe it'll sort itself out.
Speaker B: You know, I'm hoping that we can have this conversation in kind of three parts. I know it's staying top of mind and you think that's, you know, like I said, that's where people. You've already know them or something like that, but, oh, man, it starts way earlier than that in my mind. And so I'm going to break this down into this visibility section. Like, how do you Actually get on someone's radar. This engagement idea, like, okay, you have their attention. What do you do with it? To, uh, get a conversation. And then after you've had that conversation, that's like, what do you do after that? That's how I was thinking about this. But before we even get into that, let's establish your point of view these days. How'd you get here? What are you doing these days? And what's shaped your point of view?
Speaker C: My background. I went to college a long time ago for photography. Art school in Savannah, Georgia, called Savannah College of Art and Design and thought I was going to be an artist. And then I think I took a, a commercial advertising class is senior year and our professor put some film up and it was a picture of a Heineken bottle. And she said she got paid, I think something like $35,000 to take that picture. And I was like, I want to do that. And so kind of move back to Dallas from Savannah. And you know, when you're in art school or going to do commercial advertising, they tell you you got to move to New York or la. I moved to Dallas because that's where my parents were. And so I was going to kind of drop my stuff off and then head to one of those cities. And then I just got busy working in advertising in Dallas and got to travel the world and work for a photographer. And so I was his first assistant for three years and then kind of worked my way up and then really realized that I really like producing on commercial advertising, uh, shoots. And about that time, as we know, cameras were shooting video. Photo and video. So we just started doing both a lot. Um, so I was producing that stuff early on around 2008. And so that's kind of where I got the producer bug. And then since worked up through studio managers for photographers and then went agency side. I think someone on set one day shooting for some client and the agency producer was like, I don't think they meant it rudely, but like, yeah, you wouldn't make a good agency producer coming from the production side. And I was like, oh, watch that. Kind of put a little B in m my bonnet. And so I eventually went agency side and we're working on the big car brands and then now on the client side.
Speaker B: And you finally made it to LA now, right? And like, it took a while. You stayed in Dallas after college. You did get to la, but it just took a while.
Speaker C: Yeah, uh, it's funny, just moved a couple weeks ago and it's a city that I never thought I would live in, but here we are.
Speaker B: Well, I'm, uh, you know, I've gotten to know you and I just think that your perspective, uh, is a valuable one. I share a lot of the ideas with you. Um, I think that we're going to agree a lot, but maybe, who knows, maybe we'll challenge each other a little bit here too and see what's going on. We get into the practices of these things, I guess you've done all of these things and you've created a little bit of a practice for yourself though, too, right? You, you, you do actual consulting and coaching and you have a point of view that you're bringing to the table, right?
Speaker C: Yeah. As you know, when you change certain things on LinkedIn or social, social media, and this is what I did when I was freelance, you start reaching out to those people. And I, I started looking at the, the outreach from photographers, directors, reps, and I was like, 90% of this is bad. Mainly because a quick LinkedIn or Instagram search for me about me at that time, you could see that I only shoot cars. But then I would have photographers that shoot interiors or architecture reach out and ask if they could work for me. And so I look at their book and it's like, oh, you, you've never shot a car before and they're, and you're asking to shoot interiors. It's like, well, I don't produce that. And so that was like a trigger. Like not a trigger, but like a, uh, light bulb. Like, oh, people aren't researching who their outreached is into. And reps are doing this too. They're sending me heavy lifestyle photographers with no car work. And as you, as you know, like, shooting cars is a very niche thing. Like you, especially on the level of the, some of these big automakers, like it's shooting a mirror. So you have to, it's just, it's so different from shooting people. And so there is no research from a rep like a professional marketer that is supposed to be on behalf of these photographers and directors. They're not even looking at who they're sending to. So it's just this spiderweb shotgun style approach at reach, at outreach. And I was like, this is crazy and it drives me nuts. And so I could pick two channels. One, be the old man that's angry on his rocking chair and complain about it or help. And so I decided to help. And I was like, um, well, how do I help? And I would go on these walks and think about better outreach and better things that I ran into when I was freelance and the ghosting that I got from people that were in now in my position and so I was like, okay, why do I, why did I get that ghosting and why do I do it now? It's not on purpose, so you kind of have to do an audit of yourself. Especially when I was now in that seat. Like I'm, I'm just going to reply to everyone who reaches out and if they're not hitting the right target then I'm going to try to help them. I would go in and rewrite people's outreach emails. Like hey, if you want to get to me, this is how I would write it. And some people get pissed. Like I had a guy, I don't know, he was an architecture photographer and I was like, hey bud, no offense and if you don't want any help, but I'm just going to give it to you now and just kick it back if you don't like it.
Speaker B: He reached out to you, right? Uh, he asked you for an engagement, so here you go.
Speaker C: Yeah, and so I gave it to him and I just said hey, I don't shoot that stuff. And a quick kind of Google search would have helped you, blah, blah. But here's how I would approach it. And he got mad and unfollowed me and whatever, I'm going to help people. And then I was also, I'm going to take kind of some theories and practices that I've come up with and I'm going to post about them on LinkedIn for 90 days and see what happens. And about, I think it was more of the algorithm and about 45 to 50 days is this. I started to get a lot of traction and that's when people would, would come into the DMs and stuff like this and like ask me to coach or help them in their outreach. And just some things of just staying visible in a crowded market marketplace like the advertising world. And it's been fun. I mean it's been kind of well received. I think the biggest thing that I see in people is, is their own self doubt. They talk themselves out of and I do it too. They talk themselves out of why it won't work faster than just doing, just hitting send on whatever it is. But yeah, that's a quick kind of progress of how I've got into helping people with self marketing, self promotion.
Speaker B: There's a quote that comes to mind. I don't know if you're, There's a bit of a mentor to me and this is where I got my training actually. Where my point of view started was with this guy, Blair Enns, who runs win without pitching. And he said something profound to me once. He said the sale is a sample of the engagement to follow. And so if you do a weak, tired, effortless sales approach, people subconsciously, maybe even consciously think, oh, uh, working with you is going to be the same level of effort. Like, and that's the beauty of the business that we are in, is that it's not a volume business, it's a value business. It's worth hundreds of thousands of dollars, millions if you're really lucky. You know, like it's worth a lot of money to get a client and it's better to have fewer clients that pay more than to have a bunch of clients. And so if that's the environment from which you operate in, it's worth slowing down and taking the time to develop the relationships with the, with the full effort that they go, wow, this person puts more than I ever would have expected into it. So I could imagine the engagement is going to be that way too. And it's a subtle way of building trust.
Speaker C: Yeah, I think that's a great point. I think, and I'm by no means like a sales guru like Alex Hormozi or some of these people that like, are really good at coaching people how to sell products and widgets. And I just think as a photographer, director, uh, or what you're trying to sell is so different than a service that is home goods or acupuncture or something like that, or a uh, physical like headphones or a guitar or something like that. What we're trying to sell or what photographers and directors are trying to sell is they're just trying to sell themselves. So basically you need to be cool and be someone that's fun to be around, someone that's easy to work with. The communication is, is flows back and forth nicely. And so those are all the things that like I look for currently when we're looking to work with partners. Is, is all of that really simple and easy? I don't care how good your work is, there's a ton of people in the market right now that have really excellent work. Mhm. And so then you have to level up the other part. It's not the days of like David LaChapelle and all this stuff where these, there's these epic photographers and then they're assholes. Sorry Dave, if you're listening, but I don't think, I don't think he's An I just. It's an example of that caliber of the days of the 80s and the 90s when you had to kind of put up with stuff because photography and directing, when back in film, it was like, it was harder, you really had to be a better expert at the craft.
Speaker B: Yeah, you know, there's, there's. I have these kind of. I actually learned this from another person, Jenny Plant. She does account management stuff and learned this from her. And that is, you know, kind of these four levels of client management. And one is, you know, you're just a trusted executor. Like, you can do the basics, we pay you, you do the work, we're happy. But then there's the next level of we'll pay you more than what we'd pay somebody else to do the work, because we really like working with you. You make us smarter, you're a good communicator. I don't feel stressed. I feel relief. Whatever it might be. There's reasons why you're worth more. Your money, even though I could buy cheaper, it's worth buying it from you. And then there's the next level of can your work actually make a measurable difference toward their goals and the objectives that they have? And then the fourth one, ultimately, can you be so important to them that you can actually help them determine what their future goals, objectives should be? They come to you and go, hey, we don't know what we're thinking. We have something. We don't know quite what to do. What do you think? And you get to shape those goals in addition to measuring, in addition to being better to work with, in addition to just, uh, executing. So that's where I'm always trying to find, you know, how. How can you move up into that if you want to? I mean, the further you go in, the more money you can make and all that stuff.
Speaker C: Well, I think, yeah, the fourth is what you should strive for, I think, right. Starting out, freelance shooting. And when I had a freelance production company, there's so often that. And I learned this probably on like the second or third job. Like, a client would come and they would have just, for example, $100,000 budget for marketing. And when you're young and you starting on your production company and you're just trying to cover your overhead or whatever, you're like, yeah, I'll take all of it and, and get you your deliverables and what. And, uh, now if I was doing is like, and especially if it's a new company, like it's a startup or somebody that you can kind of tell they're kind of new into making video and photo assets for their brand. I'm going to start out is this your, is 100 grand your total spend, including ad spend and all that stuff? Or is, or Hunter, did you really carve out a hundred just to make the assets and then how much do you have for your ad spend? Because if you make them a kick ass video and then they don't have any ad spend money or, or any sort of marketing plan on the social side organically are paid, it's going to fall flat and you know who they're going to blame? You.
Speaker B: Right, exactly.
Speaker C: Being at the level four of what you described bringing more value and be like, oh actually I want to give you 20 grand back or 50 grand back. I can do, I can make what you need for this so that we can then take the extra or the other amount and push it so that this video or whatever we're making gets a better traction.
Speaker B: I love that we're already going into, we've got the client and we're talking about the scope of work and everything. Let's, let's start with the very. Here's what I really am excited about this conversation that is you're on the buying side now and uh, so I think you know, you wearing that point of reference and while I think you could really only represent yourself, um, and what makes you make decisions and all of that kind of stuff, I do think you've earned the right to maybe project in what is probably common and relatively universal across the business. And so with that, how do people get on your radar? Like what are the best practices? Like no one, you don't know them. They, you know, they've seen you, they found you ideally they think they can help you and they can understand why it's not just thinking of you and seeing dollar signs and just, they just want your money but they actually have thought about what works. How do they get on your radar? Give um, us some insights.
Speaker C: Yeah, I'll just share like this is what makes me open emails and, and reach back out and some of how I say this sounds very cocky, I realize that but it's, I'm just being, I just believe in like let's just cut to the chase and just say what it, what it is rather than like sugar coating it. And so kind of the first thing is when you're reaching out to somebody, someone that has a title like mine or works in an agency, someone that hires people like you, I know what this is. You're a photographer. I'm a person that hires photographer. You don't need to tell me, hey, blah, blah, like so don't even bring that up.
Speaker B: You don't need to set it up.
Speaker C: No, hey, I'm a photographer that works in St. Louis and I shoot blah, blah, blah. It's like I saw that from photographer in your email and I can see it in your signature email. Signature. It's like saying, hi, uh, my name is Chris. And then it says. And then you sign the letter Chris. Doesn't really make sense. You're just trying to create a relationship because like I mentioned before, there's so much competition out here. I just want to work with cool people that I want to be around because we're about to go on a journey together that's going to maybe take months and then hopefully couple days on set where we're from sun up to sundown, we're spending time together. And so then it's just like, okay, I want to do research about who I'm reaching out to. And let's say they're at XYZ Agency and they work on this client. Then just compliment the last piece of work you saw. Or you can be a little creepy and get on their LinkedIn or their Facebook or their Instagram or their MySpace, whatever and pull out. Oh, they went to Michigan State. I know that Michigan State just did a great X in this sport. I'm going to say congratulations or whatever and they might. And you, you are going out on a limb by assuming they're into organized sports or whatever. But just some sort of compliment that gives you an end because we're all love to hear great things about ourselves. And if someone's like, man, I saw that piece you guys did. That must have been hard trying to get that location. I've shot there too. And I know that the permitting can be blah, blah, blah. Well then, okay, we have commonality that of. Yeah, dude, it was actually sucked. We actually, I actually. And then I'll be like, I actually found somebody in the permitting office that's really great here if you ever shoot there. Because we, I, uh, think in this business we love to trade. So just stuff like that. I know that you're a photographer that wants to shoot for my brand. My brand's sick. And so that's the. And that's what people are like, oh, that's so cocky of you. It's like, no, I just were. I don't know if I lucked out or I just like. But we Got here for some reason, and I want to work with everybody. I just can't. So you don't need to say it. You don't want to say, I would love to work for you. And if you're at any agency we know, like, any agency shooting any brand, whether it's sketchers. No shade on sketchers to, like, whatever, there are photographers somewhere that wants to shoot that, or directors. And so just skip all of that and try to compliment them. And sometimes, bro, the last thing I want to do is talk about work. And so if you can find some sort of commonality in the cold outreach. I kind of have some cold outreach templates that I've written. They're on my. On my newsletter. But I think it's just finding commonality, finding some sort of icebreaker that someone will respond. And then the big, big, big thing is, is follow up. Because a lot of people send out that first one, and then they're like, didn't hear back. Well, I guess they hate me. And we're artists. We're very sensitive. Then you go in that spiral. So let's say they don't. It, uh, takes two weeks for them to follow up. And then you beat yourself up for two weeks. I've done this. And then it's a month later, you still haven't worked. Then you get enough courage to do it to someone else, and then they don't respond. We are so busy. Like, I'm at, uh, the office right now. I will leave this talk, and five people will talk to me, and I will forget everything I said on here. I will forget the other four people I was supposed to talk to, because people are constantly asking for me and anyone in any position in any agency or client. Like, especially now that everybody's going back in the office. Um, we're just so distracted, and people are constantly talking. And then I'll go to my inbox, and it's full. And so you just. The constant, like, I think there's, like a rhythm of. You send the first one. Don't hear back. Give it two weeks. And then send something else unrelated to the first one. And don't say, oh, I'm sure you're busy. Because no one likes to be told what they are. Like, try that with my wife. It's like, oh, why are you so angry? He's like, I'm not angry. Okay. Um, and then just something unrelated. It could be like, I. I saw this LinkedIn post that you did that was super cool.
Speaker B: Another. Another engagement, another kind of compliment, Another icebreaker Another, uh, it's a, it's the next episode in the series. Not a recap of the first episode. It's a moving on, moving the story forward.
Speaker C: Yeah, because. And this is just speaking from experience, when people do that, I'm like, oh, crap, I forgot I dropped the ball. I hope they are not upset with me or think that I'm a bad person because I forgot about them. Blah, blah, blah. So we're both having the same conversations in our head that we're making up. Uh, and so then usually you'll probably get a response the second or third time. You may have to do. I know this guy, he did 56 touches before he got a response and then he ultimately got a job from him.
Speaker B: Over what period of time?
Speaker C: I think it was like a year.
Speaker B: And each one of those engagements, 50, 50 plus engagements are those micro engagements of like, I saw you doing this. Super cool. I saw, um, hey, if you're ever there again, check this out. Or I just did this thing, you might find it interesting and steal an idea from it. Have it like, is it that kind of thing?
Speaker C: Yeah, just a mix of kind of like a little bit of self promotion, but never, you know, I want to work with you kind of thing. It's like, hey, I hope this is helpful. We just shot in this.
Speaker B: I actually, I find it interesting that you put so much weight into the personal relationship too. I oftentimes think it's all about the work and the value that your work brings and the expertise you bring to their problems and challenges that you can project upon because you've seen this movie a million times and you can offer something. And I oftentimes tend to not go so much into personal because I feel like maybe start with the business, we'll develop a friendship later. Not start with the friendship, and then we'll try to turn into the business, actually. I hate that in some ways, but there's gotta be a connection. Tell me more about that balance for you.
Speaker C: Yeah, I think I could see what. And I kind of had that same feeling of like, this is business, this is a transactional deal. But I just think it's. It's 100 plus grand usually, or it's more than a car. And there's always multiple stakeholders. So you need someone to go to bat for you inside of these places. And so if you have that personal relationship, because you never know, you could be losing to somebody's cousin. Like we lost some big ones when I was freelance and we always would to make ourselves feel better is like oh, probably lost somebody's cousin, you know, somebody at uh, the agency or the client that wanted to hire their cousin that has a production company or whatever. And we kind of joked around about it, but you have to give yourself a level up, an edge on some of these things. Um, and I'm not talking about being fake. And yeah, it is a deterrent because it takes longer. But we're going for like the 10 year relationship here, not the one and done. Then you're constantly selling. Right? We want to get a client and then retain them for as long as possible. And people are going to move around like people and they should try other people. But your value and what you bring to the table, and this is a different conversation, should be so high that when the people try somebody else, they're like, dang, I want to go work with them again.
Speaker B: And when, oftentimes when people move to a new position, new company, whatever it might be, you and you get to go with them, um, you get the raise too. Like it, that's the change moment, is where you actually can level up. Man, this is a, this is already a great conversation on just like this, just this topic alone. Let me ask you this. What about the value of newsletters? For me, when I do client work and trying to develop companies, my ultimate goal is can I get them to make a newsletter and not a newsletter that is a portfolio of work that is not a news, a good newsletter. In my mind, a good newsletter is a point of view. It's your point of view on the world, on the business and the world that you're in and that the potential clients and leads are in. And you offer a point of view. Not here's our work, you know, like it's, here's what we think and here's work that shows why we think it does that work for you?
Speaker C: Yes. I think you need to be putting out content every day, whether it. And I'm pretty bullish on LinkedIn and I have a newsletter, but I, I push everyone I kind of coach into creating content on LinkedIn every day of, uh, some kind. Because you're just trying to stay in people's ecosystem and so you kind of have this rhythm of like. And I just, I'm speaking from my own challenge that I made for myself to post for 90 days straight of now I have name recognition in my personal brand. And if you're a photographer, director, you have a personal brand that's like a hot topic these days to create your own personal brand. But it's, it's true. Especially like we've been doing it as a freelancer. You've been creating a personal brand forever. It's like, that's why I always encourage people when they're like, what should I name my production company? Your name. Unless you really want to, like, have other directors under you and you just want to own operate. So the newsletter is great and it's just good for business in general. Create something where people know your name and they're constantly seeing your content, whether it's written a mix of written in motion or stills. That way, if one day you're like, I want to get out of the business and I want to start a coffee shop, well, you have this huge following that's going to come try your coffee or whatever it is you created the next C stand. Well, now you have this huge following that's going to come by it. And so it's only value in creating content constantly and get people to read your stuff. And James, people might be like, well, that's. Now that's another thing I have to create. It's so easy to create content these days, quicker, just the tools and resources we have available. But working for yourself is freaking hard. And hiring a rep to do it for you is not the answer. Yeah, you need to hire people around you to, to help you. Like, uh, my first thing would be hire a cleaning. Cleaning person for your house.
Speaker A: Right.
Speaker C: Just to give you that. Just to give you that time back. The second thing should be hiring someone to cook your meals for you.
Speaker B: You.
Speaker C: And the should be someone to do your laundry just so you can have the time back. That's kind of. I can go ranty on that.
Speaker B: The. If anybody wants to hear about a conversation of whether you should hire a rep or not, there's an actual podcast episode that I did back in 2025, I believe. And uh, with Doug Stephen, who's a rep that talks about whether you should hire rep. And he's really honest in that. It's. It's very good episode.
Speaker C: Check it out.
Speaker B: Yeah, very good. Uh, so the. I always imagine that this engagement that you're talking about here, right, this email and hitting people up on social and paying attention, offering value, maybe sending him, um, a newsletter and getting me in the man and being all that. The ultimate goal of all of that is to get a conversation. Either you feel bullish enough where you can be like, I these people are engaged. I've leaned in and then I leaned back and then lay. Leaned in a little bit or you know, I engaged. They re Engaged back. You know, I got a reaction. I'm ready to ask there. I know they're ready to have a meeting with me. I'm going to ask them. Or even better, you're so good. And this is the ultimate goal. Can you put out content? And I think of the content you're talking about, the idea of daily stresses me out. I can't even imagine that, actually. But I prescribe weekly, for sure. And I try to get my clients to think of themselves as a media arm. If you wanted Ad Age or any other trade association or the New York Times, anybody to write about you, imagine what you'd want them to say and just do it yourself. Get your own media. And that's a point of view. You're your own media arm, and you can really get away with that these days. And so you have your media going. Can you create media and content and engagement that's so compelling that you ask them for a meeting? Like, you're like, holy shit. What you just said. You just said exactly what I was feeling. I never had the words for. I need to talk to you about something. I got a problem. Like, that's the ultimate goal. Right. So either way, you get a conversation.
Speaker C: Yeah. And you're just being able to share a creative outlet. Let's say. Let's just paint a scenario here. Let's say you're a photographer and you shoot cars. You've been in the game 10 years, you've had success, and then you're seeing fall. You keep seeing this, like, wave of. Of work. I think I'd be willing to bet, and I would hope somebody would just do this and report back in a year. If. Let's say you have a. A side hobby of gardening or like vegetable gardening and you post, you create a newsletter around that and how. And like, what you get, what you're doing, blah, blah. And it's. It's weaved into your Instagram or your social. Like your social profiles with your car content. When you're shooting for this stuff. Yeah. Uh, it's gonna take off because they're gonna. And the reason why I say this, and I think your business will take off is because there's gonna be people inside of agencies and stuff that are into that, and they're gonna see your stuff and be like, I want to work with them. Or her. I want to be on set with them because I want to talk to them about gardening.
Speaker B: Right.
Speaker C: A huge job. It's just like little, like, because you're. Then you're showing the humanistic side of your life. And you're on camera like, oh, so we just got these cucumbers. Look how big these out. I can't believe it. And then the tomatoes are coming in here. Oh no. Bugs got these and then some be like, I got this thing for bugs, but they happen to work at like this huge agency. You know, it's just uh, it's. And I got that from. We went to this real estate conference thing and this guy was teaching all these real estate agents social media and he was just talking about no one wants, no one cares about you talking to them about interest rates. They want to know, are you a human being and can you help them with the toughest decision they're ever going to make in their life? That's very scary. Buying your first home, showing them how you, how you make a brisket on your new smoker and stuff like that is like, oh, I want to be, I want to talk to James because he's likable and I want him to help me buy my first house.
Speaker B: Let people in is how I'm characterizing that in my brain. Let people in and know who you are, not just what you can do. And I think that, that, that is a, uh, such. I can't wait to even process this and think about it more. That is a fantastic way to demon. To put. To make yourself visible is what I mean to say. That's a great way to make yourself visible. It really, it's true to who you are and it's very authentic. And I want to say, uh, you know, we've spent a lot of time on this first part, this visibility part and I think it's worth it because this is the part that most production companies and even agencies, but definitely production companies stop because it's the hardest part and they don't do it and it takes a lot of work. And so I think we just, I think it was worth spending time on that. So let's get to the next part.
Speaker C: Or they do it for a month and then they get booked on a month long job and it they. Because they don't have a system in place, they stop doing the uh, visibility outreach and then they have to start from zero again.
Speaker B: That's why I think a newsletter is really good. If a monthly newsletter is such a perfect cadence because it forces you to put it into your workflow system and then you can use the content that you're making and the time you're making to make the newsletter to repurpose that content. I always say, like in one newsletter there's probably 12 pieces of social media content because you take micro bits of it, you know, and you do, and you pepper it around that with a little bit of this kind of personal interest and affinity. Yeah, yeah, yeah. If you're showing your affinities and have people, I think that that would be a really strong. And keep it going. Yeah, I ah, agree with that.
Speaker C: Yeah. And just I've heard it referred to as like a content waterfall. So the newsletter is the top of the waterfall and then everything flows into other pieces of smaller bite sized content into other platforms.
Speaker B: So let's say you get a conversation. Whether you asked for it or they asked for it, it's happening and they get a conversation. This is where intake begins. Even if they don't have a job yet, you're looking for fit, right? You're looking for, do they have a need that you can help solve? Do you have the expertise? Do they have a budget? Do they have, you know, experience in this, all of this kind of stuff. And I always encourage people to go deep if, you know, if you feel something in your gut or if you're like, oh, that's inappropriate to ask, those are the questions to ask. Are you okay with that? Are you or is it just an agm, another good meeting that it doesn't need to have any agenda with it yet. How do people meet with you? What's appropriate in your mind and not appropriate appropriate.
Speaker C: I think everything's appropriate. I don't think there's any off because I'll just, I won't answer it or you know, but I've never been asked like an inappropriate question in a meeting. And I think, you know, if you get them the. You're correct. Like the biggest thing that you want to do is push for a meeting like a in person or a coffee or a zoom, whatever we're calling it these days just to kind of get to know personalities on both ends. Because as a photo, let's say a photographer, you may get on the call and not like that person just because they work for a sick brand and that doesn't mean you need to go work for them because you don't want that. I mean you should have a velvet rope on your business as well and not let any bad clients in. It's just miserable. It's not fun. I don't care who it is. And so that's, it's for, it's for both of you to kind of like, hey, let's just like, it's like. And I had A, uh, client that I coached, and he was like, dude, this is just like dating. I was like, yeah, it's exactly like date. Yeah. And it's creating just like a wrinkle in my brain of like. Because the biggest thing is. And the reason why, saying let me know if I can ever work for you or let me know if you ever have a job that I could fit into is like, it's very forgettable and are just checking in, you know, um, we don't have, like, a stack of papers on my desk that when like, oh, here's X photographer. Yep. I have this project just for you. Thanks for reaching out. I've been waiting for you. I have nothing right now that I need to hire anyone for. Tomorrow may be different. Next week maybe different. But there's nothing right now in this year because everything we've already booked, we've hired everybody. So that's even. You're six months away from even having a job. But there is always stuff that pops up. And so if you're constantly in the rotation, like, I have worked with a ton of people.
Speaker B: People.
Speaker C: And if you were like, list them. I would. I could. I can only think of like, three people.
Speaker B: Right.
Speaker C: You know? You know what I mean?
Speaker B: There's too much to keep track of.
Speaker C: And three. All three of those people is, Are, ah. They're like, I'm in this person's wedding in December. They're a good friend of mine. And we, we became friends from set and photographers that I've just worked with for a long, long time. There's really good ones that I just can't think of, but that I've worked with before because my. My brain goes blank. But if they were to hit me up right now, I'd be like, so excited. Like, yo, thanks so much for reaching out. I've been. I remember when we went to Indonesia and shot that thing. But so that's just the. Just staying in the loop, providing value. If you shot, if. If it's warm, you've shot with people before, it's that, hey, blah, blah, blah. Remember when we did xyz or sometimes I used to. I used to like, let's say we went to like, a cool place like Hong Kong or something and shot. I would find something relevant to Hong Kong and three, two years later, if it was a successful, cool job, and just send it to them. Remember this? And then you're like, dude, uh, oh, hey, man, I was thinking about you. We actually have a job we need to shoot next week or next month. You're just battling people's memory.
Speaker B: Yeah. And by the way, that is a great use of AI for this. AI is good at many things. The thing that I find is so extraordinary at, uh, is connecting dots that you can't keep track of. Like, there's no way you can keep track of it. But if you use AI to know what you've been doing, what they're doing, all that kind of stuff, and you want to reach out and you're like, hey, uh, can you connect something? You're doing this thing and they can go back and, like, remember that thing you did in Hong Kong? You should share that.
Speaker C: Um.
Speaker B: Oh, God, I forgot all about that. Yeah, totally. You know, AI is a great, great tool for that. I love it for that reason. Okay, so there's the conversation is, like, the beginning of time for me. There's pre time, then there's post time. Right. And so. And the engagement and the development is what I call them. So the visibility is the engagement and the development is after the meeting. And they're the exact same thing. Right. You're staying top of mind. You're staying in front of people, except for one big difference. You had the conversation and you learned about them. So the engagement that you do after that conversation better be better than the engagement you would do before that conversation. And if it's not, you weren't listening and asking the right questions and doing your job well enough, you're not caring enough. Because if you had a good conversation, I should know, Chris, what your KPIs or OKRs or whatever it is that you have to meet to, like, how is your job being measured for success? I should know that. I should know what. Who you're working with, what's working, what's not working, what kind of budgets do you have? What problems, what challenges, what things? Launches are coming up. What do you need to build anticipation for? I should be able to know all of those things so that I can go back and process and go, wow, Chris said a lot of things. Well, here's what we do. And, uh, you know, and then that becomes how you stay top. Staying top of mind after the conversation in my mind. And I would love to for you to say I'm putting too much emphasis on this, if you believe that, but that it really needs to be rooted in the context of a good, deep, meaningful listening session. Is that accurate?
Speaker C: Yeah, yeah, 100%.
Speaker B: Could you give me an example of when someone's done a conversation poorly and you're just like, that was a waste of my Time and when any specifics around someone's just did something and just made you go oh man, that you just. That was a good, you know, whatever. It really left a mark and, and work happened as a result of that.
Speaker C: No, I mean I think this is a perfect example. I can't remember the ones that were bad because they're forgettable.
Speaker B: Right.
Speaker C: I think the, the ones that are great are just when they. And I know it's hard like people are going to have all sorts of things and that excuse but how do you know if they're. What they're into or if it's a cold. If it's the first time. I think other people that just understand me and the perspectively of like the business of making content or whatever it is and just. And are good listeners and you feel kind of connect kind of the same way. When we first met you just feel this like, hey, I get you, I get the world you're in. And we, we kind of vibe really easy because there's, there's a personality type for everyone everywhere. I m truly believe that. And sometimes it. We've actually got on um, bid calls before where the people that we really want to work with, they're just combative in the, in the feedback of like the creative direction. It's like, well, if you're going to be like that now, you haven't even won the job. How's. How are you going to be when we're on set together and we want to change but you don't want it kind of thing. I think it'd be open, amenable, honest. All like the good qualities we look for in anyone when we're trying to talk to them and just wanting to like. I, uh, know you probably think it's a waste of time, but just shooting the shit about something other than work. It's kind of like when you come home if you're married or in a relationship and your, your partner asks you how your day was and you just like uh, this is the last thing I want to. Can you ask me anything about it sucked. Like today was not great or when it's good you want to talk about it, you know. But sometimes you're just like what are you into? Like, is it surfing? Is it skateboarding? Or is it. I even kind of sometimes like nerd, uh, out on because I'm have a background in photographer, like nerd out on camera stuff or you know, stuff like that. And like we've talked about, we talked about when we first met is like being Aware of what's. I could quickly have all these context clues about James in this room that we could relate on, talk about. I could ask you about that. Then it's that old saying of the more I talk to you about me, the more I like you. I think I said that right. Those are the good conversations. Then you leave like, I'm going to freaking hire that person. And usually you don't even talk about process of photography or shooting. And it's the long game. It takes longer. I know it does. But just imagine the doors that'll uh, you're playing that, like I said, the 10 year game. And if you're in a place right now where you're struggling to get work because finances are tight, it's kind of a different way I would coach. It's like, all right, let's see what your structure is around your finances, because I can feel that too. And you're like, I just need a job. I just need to win. And there's nothing wrong with that. Sometimes it's. I've had guys and girls that I've worked with in the past that come and they're like, brother, I haven't worked in 12 months. Why don't you reach out sooner? You know? But it's like, there's empathy there.
Speaker B: There's no better time to do business development than when you're busy. When you're busy, your perspective changes. Your, your vibe is different. You know what they say, the best time to go shopping is when you have money in your pockets, right? And so you have options. And when you have options, you, you act different when you have options and you can have a looser conversation. And I think that's really good. Okay, so we've had the conversation. It's been good. We vibed out, we got to know each other. We found some affinities and common interests. They like the war. You know, like, I understand you and your needs. You understand what I offer, offer, and it's cool. All right. Uh, we don't have anything right now, but man, this would be great. We're a fit. Like, let's just stay top of mind, you know, let's, you know, stay close. You know, there's a technique that I want to get your opinion on. I learned this from the book the Challenger Cell, years ago. And uh, which is, by the way, my favorite sales book of all time, the Challenger Sale, and uh, the consultative sales and really leaning into. And it's about helping people versus trying to just get money. And so. But there's A favorite line that really sums up the book. And it's, I don't know, back in, like, the old, you know, decades ago, you'd always, like, tell me about your problems, you know, like, where are you? You know, and that kind of thing. I hate that big general, uh, question like, where are you struggling? You know, instead of asking like, that, you should be so intelligent about them and their market and their customers that you can confidently and accurately say, do you know what should be keeping you up at night? Here's something. Not what's keeping you up at night. Here's what should be keeping you up at night. And you can deliver intelligence and insight and teach and offer in a way that makes them go, oh, shit, I didn't see that. Um, thank you. That's the level of understanding that I would hope would come after a conversation so that you could actually do that and that the conversation is so informative that you could actually make that kind of, uh, statement and back it up. Of course, that's the post conversation, um, staying top of mind that I prescribe. Does that make sense? Does it resonate? Does it not?
Speaker C: Yeah, I think it, I think it does. There are some times where people will, like, start telling me stuff about the company that I work for and I'm like, yeah, dude, uh, I already know and I don't really care, but I have, you know, and maybe that's just because I'm tired and hungry and not have anything to do with, like, the information that's being served to me. And I think that's kind of what you were saying, but I think it's more of, like, the challenges that, that come when you're in the business of making things and making that seamless and being a help is where I'll see the most value. There's another layer that I'm not used to, and let's say it's a different way of looking at an estimate or presenting a treatment, or I have to go through your rep to then to your producer and then to get to you, which I, I understand why. There's layers. We have layers. Everyone has layers. Because you need to maximize time and you don't want to constantly be doing this. But if it's, like, if it's harder, then it's going to deter. So, yeah, I think it's. It is understanding of the challenges that we go through post production, all those things is like, that's the way where I'm going to create and find, not create. Um, that's where I'm just Going to look to see value and the questions being asked around that stuff. If we're already deeper into the conversation, like you said, I think you give
Speaker B: a good potential negative trade off of that approach. And that is you say something that isn't meaningful and is wasting, perceived to be wasting time and not helpful at all. And another one that I always, this is the one that I always think about is um, actually being too prescriptive when you don't have enough information. Information like you offered something, I could presume what you are going through because I have experience in this. But there's a lot that I don't know. I don't know what pressures, I don't know your bosses, I don't know your colleagues, I don't know what you might be going through. And I say something that is completely off because I just don't have enough information and, and I miss the target and it looks bad. So like either, you know, not relevant enough, I could tell you just wasting my time. Or dude, you just made way too big of a leap here. And it's uh, you know, like you, you clearly are not someone, you know that's going to listen. Well, you know, these are, these are the potential trade offs of that.
Speaker C: I think it's sometimes too when, and people ask me this all the time, hey, I just met with this brand and they were mentioning a project that they might want to work on or something like that. Or I just, I want to pitch them on this idea I had around their brand and they're like, should I do it? I'm always, I was like, no. Because even if the idea is great, you're pitching them something they didn't ask for. And if, if you kind of heard them ask for it, then you're doing it for free. And then what if it's just you didn't have enough information and context to hit the nail exactly on the head. So then you have this like bad taste in their mouth. Even if it's a great pitch, but you just missed the mark somehow on some sort of, it's probably in some sort of strategic angle of what you pitched. And then they're. First, they're just, they're just going off what they saw and then they have a bad taste in mouth about you. And so you're assuming that they want to see your pitch, which is probably not the case unless it's like a doc that is very niched to some sort of thing that you've already shot. Then there are people that want to develop, people that Want to see pitches like that all the time. But if it's, if it's a specific, let's say it's a running shoe brand and you had a conversation with this person, you kind of got the feeling that they want to see some creative from you and so you create this pitch for them and then it just misses. Well, then you miss out instead of developing, developing, developing, and then ask them, hey, I came up with this idea, I'd love to pitch it to you. What do you think? And then be like, yes. Then you start asking questions. This is kind of the direction I'm going. Is there any more context you could share? So I hit it on the head and then make a dang NDA so they don't steal your idea.
Speaker B: Yeah, that's, you know, case studies are a great way to approach that. So you know, you just. I just did some work for a client. I'm actually really surprised or impressed with how well it performed. Actually the numbers were pretty good. It strikes me that you might have the similar need or have like this, a parallel lookalike, uh, ideas going on here. I'd love to walk you through what we're doing and see, and see if any of this fits with what you're trying to do and ask you some questions about that kind of a thing. Yeah.
Speaker C: Oh yeah. Case studies. We just, you know, we just shared, we just shot X, Y and Z and this was some of the efficiencies we had. We were able to capture, you know, three times as much content because we brought in this one person. You know, stuff like that. That's, I love stuff like that. Just hearing about efficiencies that you could have inside of the uh, production.
Speaker B: Oh, that's great. Yeah. Efficiencies. What about innovations?
Speaker C: What do you mean by innovations?
Speaker B: So efficiencies I chalk up to we're able to do something faster and cheaper and still get the results or even better. Or we've created, we've created an AI tool that makes that so you can use your car commercial for four different seasons around the year. Like that's an efficiency in my mind. But an innovation might be more like we. Well, and really what I'm talking about is kind of creative and strategic innovation. So like we figured out a cheat code for getting people to not skip the intro of a, uh, you know, pre roll video on YouTube or you know, like whatever.
Speaker C: Like that stuff. Yeah, I like that.
Speaker B: Yeah. Creative and strategic innovation is what I,
Speaker C: ah, the ladder of using your car commercial in 40s in the seasons. I'll lose a lot of friends if I agree with that one. I know. It was just.
Speaker B: I'm just riffing. I'm just riffing here.
Speaker C: Yes. No, I know.
Speaker B: Well, okay. So what we've done here is created a perfectly scripted playbook for your inbox to be absolutely saturated with people. This is going to be an interesting case study to see if people were listening and did the work. Because basically we have the playbook right here for how to engage you. Is there anything we haven't said that you would hope they would use to engage you?
Speaker C: It's funny you say that, because I've posted on LinkedIn and then the same day someone will DM me. And it's what I just said not to do. They're not reading it. You know, they're like. And I get it. Like, I've been there. That you're just trying to. Like you're nervous and you're like, it took you all. It took you all of your energy just to write the thing and then it took more of it to hit send. But I would just say, like, slow down. Understand who that person is. Do they produce the type of work that I shoot or want to shoot? If I want to shoot it and I don't have any of it in my book, it's a completely different conversation. Then it's like, I'm obsessed with what you make. I would love to be able to break into that industry. Do you have 15 minutes of time where you could just coach me on how you did it? Yeah. And I promise you your return rate of people wanting to. Because I love to talk about this shit. I was probably most likely, if I'm not up to my knee, like, right now, it's tough because I'm learning a new role. I've just moved to la, like, trying to figure out where the bathrooms are. But your. Your return on replies will go so far. And this is for the person that's breaking in or new or even, like, been shooting for a long, long time and want to break into a different part of the industry. Industry. Because people would love to give 15 minutes of your time. If I could just do this all day, I probably would and get paid for it. So that type of stuff of. That's just a really great message. It's staying top of mind, just not being afraid to send the 56 return. You're not being annoying, I promise. Unless you're annoying. Like, you're not. Like, sometimes you can feel that angst of, like, Well, I guess you don't have time for me. Or it's like, dude, no, I just forgot. I'm sorry. I'm a human. Like the other day, the other day, like I put clothes on top of this laundry bag and my wife laughed at me. It's like, yeah, sorry. I don't know why I did that. That was really dumb. Same like our brains just shut off sometime. It's not because we don't like you, but it's that one thing of just hit it again, hit send again, come up with something clever that's you and stay in that field. I would highly encourage a newsletter posting every day or at least three days a week to just stay top of mind and relevant.
Speaker B: Reveal yourself.
Speaker C: Reveal yourself. I would encourage people that's uh, listening. It's like, what's a hobby that you can just put out to the world? That's something we talked about. Would be really fun to see and it doesn't. The biggest barrier of like people are being you're. You're having this new thing. You're so used to making content for other people and then when you want to make it for yourself, we always just shut her off. It's like. So I was just like the imperfect nature of like my newsletter now and then two years ago or however long I spilled it of just like posting on LinkedIn, I don't care. I'm just going to do it. And if people want to make fun of it or say that I use incorrect grammar or I don't care. Because if you want to make fun of me for that, I don't want you to be in my life.
Speaker B: Mhm.
Speaker C: Yeah. There's something for everybody.
Speaker B: Chris Whitten. I opened the show up by saying you're a generous person. And what I'm realizing now is that I was actually thinking too soon. Small. You were way more than generous. Uh, that was such.
Speaker C: Oh, uh, thank you.
Speaker B: Yeah. Such a great recap of how to stay top of mind in three different stages. Really actionable, practical ideas. I believe you. I think you do represent a universal perspective. Thank you so much for being on the show and thank you.
Speaker C: Appreciate it. Thanks James.
Speaker B: All right, thank you so much, Christopher.
Speaker A: Thank you for listening to Crossing the Axis with James Kebles. If you're interested in joining the conversation or have a topic you'd like covered, please drop a note@kebless.com that's K-E B L A S dot com.
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