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Leveraging freelance writers for your agency (featuring Gideon Stein)

Meeting the need for high quantities of high quality content
Gideon Stein

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Agencies have a constant need to “feed the beast” when it comes to content creation. Public relations and marketing firms have always had a strong reliance on the written word, but as clients become publishers and social media places increasing demands on scribes, the challenge of finding and managing writers only grows.

On this episode, Gideon Stein of Write Label explains how his team has built a roster of writers to help meet that need. There are lessons and ideas for anyone who is looking to outsource writing responsibilities or build their own network.

Gideon discusses a wide range of topics including:

  • Write Label’s approach to filling client requests
  • Managing writers for maximum results
  • Recruiting new writing talent
  • How Write Label extends the range of many agencies
  • The role of AI and machine learning in the writing process

You will also get to hear the funny story of how Write Label came to be what it is today.


About Gideon Stein

Gideon serves as the CEO of Write Label. Previously, he was founder and CEO of LightSail Education, prior to its sale to an international private equity fund. A leader in the national education landscape, Gideon serves on boards of several nonprofit organizations including New Classrooms, Narrative 4 and Chalkbeat. He is also the President of the Moriah Fund. Prior to LightSail, Gideon co-founded and served as President of Future Is Now Schools, and he was Founder, Chairman, and CEO of the enterprise messaging company Omnipod, Inc. (now a division of Symantec).


The following is a computer-generated transcript. Please listen to the audio to confirm accuracy.

CHIP: Hello, and welcome to another episode of the Chats with Chip Podcast. I am your host, Chip Griffin. And my guest today is Gideon Stein. He is the CEO of Write Label. Welcome to the show, Gideon.

GIDEON: Thanks so much, Chip. Great to be here.

CHIP: Yeah, it is great to have you here. And even though we do not record the video of this for posterity, it is interesting to note that as we were acknowledging we have the same Barber, so I assume that means that we’re smart. So I think I think every guy I’ve ever known with a shaved head was a smart guy. So I’m looking forward to

GIDEON: my great uncle used to say that God made a few perfect heads and the rest he covered with hair.

CHIP: That’s a great line. I may have to borrow that one. Well, before we dive into the the conversation, why don’t you share a little bit of your background and what right label is?

GIDEON: Sure. So I actually came to write label about two years ago now. The company was formed a couple years before that. It had been a social network for comedy writers, where people would come and compete to come up with the funniest Wine on a bunch of different news stories of the day and the company would also post contests and challenges for writers. And it was really meant to be a social network, an aggregation of folks coming together to compete and have fun. A little bit before I joined, the company decided that it was going to be tough to monetize a social network with 10s of thousands of people and not millions of people that this was fairly niche, but that there was something really special going on that there were a lot of really funny lines. We had writers from a bunch of different types of you know, professional sites on The Tonight Show and Saturday Night Live and, and sitcoms and you know, professional comedy writers, but then there were also a ton of amateurs and the amateurs were doing really, really well in terms of upvotes and likes from the community. And people wanted access to these writers, both the pro writers as well as the amateurs. And so the company started creating a platform for companies to be able to come and access the writers. What I did when I came is took about 50 different skews that the company had, we really consolidated down to just a few when we found specific use cases. And what we have turned the company into is an on demand platform for short form content for media companies in particular, but also brands and agencies that need that content very quickly. And one of our biggest use cases right now, as in the advertising space, where our writers are writing thousands and thousands of ads for radio and TV, internet, digital signage, outdoor signage, you know, and doing spillover work for brands and agencies, where we’re delivering really high quality content, very inexpensively or cost effectively. Very quickly. And that really is what we’re able to do. And we’ve used technology to harness all of this data. We track who does well in terms of what types of projects and we can route or assign based upon what we know somebody is good at.

CHIP: It’s a really interesting story. And I’m always fascinated by stories of pivots as a serial entrepreneur myself, you know, I, I know how, how often startup businesses make pivots. Obviously, this one’s a particularly interesting one. Do you have a background in comedy, or did you come to it more for the from the business side?

GIDEON: Sure. So from the business side, I have run I had three companies previously that I founded, ran and sold. The first one was a magazine in the 90s. The second was a technology platform that was based on instant messaging technology and we sold and to enterprises fortune 1000 companies. It was file sharing and real time communication. So it was like slack

and Dropbox combined, but about 10 years too early. We did well, but not, you know, not like what those companies have become. And then I had an education technology company that I’m super proud of and ran for a number of years. And we sold it right before I joined, right label.

CHIP: So as a serial entrepreneur yourself, then you’ve seen lots of evolution in communications in technology over the past 2025 years. And I think one of the things that was interesting to me about right label is the way that you’ve pulled together a network of freelancers sort of taking advantage of the gig economy, which I think is one of the biggest trends impacting the agency space these days. And you’re harnessing that power to really extend the capabilities beyond what an agency with just in house writers could do.

GIDEON: Sure, you know, and I think one of the things that really differentiates us from the other gig economy players, you know, an Uber or something like that, or an Uber Eats or something like that is that the folks who work for right label and you know, we love our writers, we live and die by the quality of our writing. You know, this is what they want to spend their time doing. They want to be writing and quite honestly, a lot of them want to be writing on a lot of variety of projects, you know, if they aren’t unable to, because of location or you know, geography, whatever, they’re unable to get their dream job writing, or they do some freelance writing, but they need to fill up some more time. You know, they’re not serving coffee, they’re not driving a car around, they’re actually making money, picking up jobs through us doing what they love doing and what they’re good at doing. And that makes our platform even better.

CHIP: And I as someone who has managed teams of writers, freelance writers in the past? I know it can be challenging. And I certainly haven’t done anything on the scale of what you’re doing. But how do you how do you make sure that you’re getting the right fit for the projects? How do you, you know, some people are better at writing different kinds of content or writing different types of subject matter? How do you really is the platform that’s helping you or as you have human editors who are reviewing it, how do you make those decisions?

GIDEON: So that’s an excellent question. And it really that is goes to the heart of what we do. So using data we know who is good at writing, say, an ad for mufflers, versus an ad for a chain of pizza companies. But we also know more than that we know who’s good at writing a funny muffler ad versus writing a more serious mathcore ad. We know who was able to write, you know, a, an ad for that chain of pizza restaurants in a certain style, maybe a specific vernacular, we have customers, for whom it is very important that the world writers are writing with knowledge of the place where the ad is going to be heard or seen. And so we’re able to toggle back and forth between, do you want a regional voice? Or do you want a national voice, some of the clients really prefer a national voice. They say, for Bass Pro Shops, we approached it in a very different way than most of their writers or regional who really are very familiar with basspro. Our customers themselves, you know, that often you would think that that’s like, you know, the Holy Grail, and that’s what you want.

But they in this is a

specific example. basspro was really happy with the fact that we took a completely different approach. And when we go to our customers, and we go, we, when we work on one of these projects, they’re not seeing just one iteration, they see five or eight different ideas that were written from five or eight different people who weren’t necessarily in a room collaborating and so they can be very, very different. And you can end up getting something you know, very specific around what you want. By taking ideas from lots of different perspectives,

CHIP: so walk me through the process. So if I’m Bass Pro Shops, and I come to you and I say, you know, I need, you know, this particular ad copy, how does it work? on your end? Do you do you have? Do you use your platform to identify a few people and talk to them? Do you just say these are the two I’m going to use admin just walk me through the process?

GIDEON: Yep. So what happens is usually,

you know, when the best pro shop example, we’re working with a media client, so either radio or television network, and they that the salesperson was pitching bass or bass was, was renewing with them. And so they say we here, you know, here’s what we need. We need a bunch of new ideas for this customer. We want it to be funny, and if we want funny, we can designate that we want it to be slapstick, or we want it to be ironic, or we you know, you can you can sort of pick how Funny you wanted or what type of funny you want? If you want serious, you want it to be emotional, do you want to be intellectual? Do you want to be just engaging? Or do you not even care, as long as it’s good, and that actually is an option that a lot of our, a lot of our customers choose, because they don’t even know they just want to see some good ideas. And so they make it funny and they make it serious and make it engaging, whatever it is. So they fill out a brief. And then that brief goes to writers who are specifically segmented to work on those types of projects. So, you know, and and if they choose, you know, we want local vernacular versus national, then, you know, it would go to a smaller subset of writers on mobile versus opening up to everybody. So then what happens is, so it goes out to writers. And, you know, for us, it really depends upon how you know, if the system gets very busy, then we segment the writers into lots of different groups. And, you know, whoever’s available will end up writing on it. We then have editors who review everything that comes in. And everything is put through a grammar check program. We add it, we had it for grammar, we had it for syntax we had it for just does this make sense. And as a good, we tend to do that pretty quickly. And we have editors in stay in house, but we also distribute them, kind of like our writers. And then from there, we make it available to the customers so the customers can actually see it as it’s coming in. Because if they want to communicate with the writers, they’re able to do that. But not until it’s until the project is filled up. Do we feature the ones that we think are the best because we want to get, you know, and people are competing. So there are only let’s say there are only five spots or eight spots may go out to 100 writers may go out to 1000 writers, but the people who come and take out a ticket or claim at first are the ones that are going to be able to write on it. If it’s terrible, we’ll delete that one and then somebody else can write on it.

CHIP: So how do the writers get paid? They get paid for submission to they get paid? If it’s selected? How does it work from the write ups? And,

GIDEON: sure, so the writers are paid a few different ways. Number one is they get paid a small amount of money when they are selected to join the platform. So after they’ve tested in and we say you’re good, and you’re qualified, or you’ve been you sat through our training and qualified to write for radio,

we segment them for our radio,

writing projects,

they’re paid a nominal amount to join the platform. And then for those first five or eight or 10 submissions, we pay a nominal amount. So you’re actually getting paid for the work that you’re doing. And then there is a prize pool which is much larger, and you know, it’s other winner take all or it’s split, if the customer likes more than one submission.

CHIP: And so, you know, as you’ve been involved with this for a few years, now, you know what What are some of the the key lessons that you’ve taken away from trying to work with and manage these large pools of freelancers? And, you know, if I’m, if I’m inside an agency or another organization trying to manage writers myself, you know, what, what insights can you offer me?

GIDEON: Yeah, so, number one, it’s hard. You know, this is, this is hard work. You know, it seems like it would be easier than it is. The technology helps a great deal. Oftentimes, people say, you know, if I found somebody whom I really liked, and really did a good job, can I hire them again? And our answer is no. You know, we really believe in the power of community and the power of crowd. And, you know, while they may be in that, they may be, you know, one of the people that we go back out to, we’re going back out to a lot of people and we might have, you know, what worked and what didn’t work. But we really want you know, to ensure that, we’re able to We’re not a we’re not a one to one sourcing agency. We don’t do matchmaking. We provide solutions to problems at scale. And in order for us to do it at a really high quality at scale, you know, this is the model that we found works really well for this.

CHIP: And have you found software off the shelf that helps you manage this or if you had to create your own platform?

GIDEON: Well, that would be nice. Yeah, yeah. No, we have created our own platform. We have a phenomenal in house tech team. They are the best I’ve ever worked with in 20 years of doing technology. our CTO is really high quality. And, you know, really understands data and understands machine learning. And we have built a platform that is, you know, we’ve spent a lot of money on it. You know, this, the company had a significant base of technology before I joined and we spent a lot since we retooled a huge amount rewritten Everything from the ground up when I joined, but, but those key learnings were things that we, you know, we came by the hard way. So this has all been custom developed, and, you know, really works very specifically to our, to our particular needs.

CHIP: And now you’ve indicated that you work with brands, media and agencies, obviously, the listeners to this show are primarily on the agency side, how do you how do you work differently with agencies than with brands or media? Or is it really just, you know, just pretty similar process?

GIDEON: Well, agencies, you know, we, our approach is really about how we can help them extend their range more. You know, we don’t want to we were not coming in and saying or replacing anybody’s job or role. And we’re really clear about that. You know, that the agencies know their clients really well. They know what they want, they know their particular voice. You know that and they They do the media buying and all this other stuff that that we don’t do. What we can do is help provide a lot of ideas from a lot of different perspectives to help them be even better at being responsive to their client and be able to take full credit for it. The thing about right label, it is a play on white label. And we are very focused on the fact that our brand is in the background. We want our clients to take credit for the work that we do. All of our writers sign NDA is, you know, they are not allowed to talk about the work that they do. You know, we take that very seriously. And we want to help agencies be better at what they do and the work that they deliver to the client.

CHIP: Now, obviously, for folks who are writers, there’s been a lot of pressures on them in recent years as as media has become much more competitive and those tried to drive down what what they will pay for content. You know, Kaiser’s are and brands are becoming much stingier with their dollars and they were in the past. The regulatory environment is getting tougher I think of California is a B five, for example, which has really hit freelancers. Pretty hard. You know, how do you how do you see the the ecosystem of writers changing and adapting? And does that? Does that help or hurt those people who are in the market for those services? And does it help or hurt the writers themselves?

GIDEON: Yeah, so I like to say that our writers are not, we didn’t develop in them and test tubes. This isn’t, you know, some separate community that exists out there. We are tapping in to many of the same communities, although we bring on folks you know, who may be new to this and just have a lot of talent. They have an English degree. It’s a mom who used to be in the field isn’t anymore and this is kind of the perfect solution she doesn’t really want to do. Or a stay at home dad doesn’t really want to do you know freelance gig, they want something that’s much more discreet. You know, I think that we add a lot of value to them. What we hear from a lot of our writers who do a lot of freelance work is that they get to work on a lot of different client projects in a single day. Which is kind of unheard of in their other roles and the other jobs that they take on, where they may be working with a single client on a single project for a single campaign for several months, and it’s about moving commas around and and very careful word choice. You know, here they get to be much more creative, they get to practice, they get to have a lot more fun with it, they can work on five or 10 or as many as they can write in a single day projects with, you know, that many different clients in that many different industries. So, you know, we’re really, we’re really focused on on supporting writers on helping them develop on helping them create, you know, a body of work A portfolio for themselves that they can be proud of, and they can use if they want to go and get a job. You know, we don’t consider this platform for, you know, traditional freelance.

CHIP: Gotcha. Are there any questions that I haven’t asked you that I should have? Are there? Are there things about your platform that you think would be helpful for listeners to know?

GIDEON: Well, somebody, I was actually interviewing for an executive assistant today. And she said that she read an article that I’d forgotten about that I did. I didn’t hear before about AI. And it’s sort of to your point, you know, the, the the the article is asking, and I think some people are, are, are thinking about, you know, what happens to human creativity, as machines get smarter and smarter. And we really do think that a lot of what we do can be enhanced through machine learning, but that’s really not on the writing side and not on the creativity side. It’s really on the routing and You know, what we talked about in the beginning of our discussion, how we can route a specific request to, you know, a specific group of writers. So we think is going to be the system predicts, is going to be best able to, to deliver the best content for that specific request. That’s where we think the technology is going to sort of peek. We don’t believe that ai ai is going to be able to replace human creativity. And so, you know, we are creating a platform that we really think makes writers future proof and uses that technology to really deliver the peak of human creativity. And so you know, it’s one of the things that we’re really excited about with what we’re delivering. I think that’s one of the reasons why writers really do like to write for our platform is because, you know, we are delivering for them a huge amount of opportunity to write on a lot of different types of projects and do a lot of different kinds of fun work, you know, at, at their leisure when they have time to do it when it fits with their schedule

when they’re doing other things.

CHIP: So you don’t see the sort of the move towards AI and machine learning, where, you know, a lot of folks are trying to get it to, quote unquote, write articles. from a technology perspective, you don’t really see that as a threat, nor it doesn’t sound like do you see it as a way to, to marry up with what you’re doing instead, it’s, it’s just something that’s, you know, not likely to be successful in the near term.

GIDEON: Well, so that’s an interesting distinction. So if it’s a factual, you know, article, whereas reporting on news, that is one thing when its creativity when it’s supposed to spark engagement or a smile or an emotion that’s something very different there is an art more than a science to a lot of this. You know, of course, there are elements of this that you can reduce to an equation but I you know, the the magic and I have friends who are novel Son, you know, you read what they wrote. And, you know, I don’t think a computer could ever even though a monkey could, you know, theoretically, do it in an infinite amount of time sitting in a typewriter, they can, you know, spit out Shakespeare. You know, that doesn’t really happen in practicality, nobody has an infinite amount of time. And I don’t see computers being able to deliver that sort of genius Spark. And I’m not saying all of our content is genius. But that sort of spark of creativity, that we really aim to deliver what the human touch. So humans are doing the writing humans are doing the editing machines are doing the routing machines are making it much more efficient. But that’s sort of where the machines begin. And that,

CHIP: and I think that’s a good distinction between sort of straight news reporting versus the creative side. You know, I have one of the businesses I used to own was a media monitoring and analysis business and, you know, the result drive towards automated sentiment analysis and the biggest challenge for computer was not being able to handle sarcasm and, you know, and sort of the more glib form of communication that you have on social networks, you know, versus being able to interpret a, you know, a large academic article or something like that. Yeah,

GIDEON: it’s hard enough for a lot of people to handle sarcasm.

CHIP: It is Yeah, well, I mean, think about it, how often have you received a text or an email and sat there and said, you know, is this are they serious? Are they being sarcastic? Are they trying to be funny? And so it you know, when you take the human element out of it and are just looking at the words on a page, it can be very difficult for one human to interpret another human let alone introducing a computer to the mix.

GIDEON: Absolutely. Couldn’t agree more.

CHIP: Well, getting if someone is interested in learning more about right label, are you where should they go?

GIDEON: Come to write label dot com. So right w r i t e label l a b e l.com. And you can come you can find out about us if you’re interested in writing, you can become a writer or email me at Gideon at write label com Happy to, to engage.

CHIP: Right? Well, I think this has been really helpful for agency owners who are always looking to feed the beast find ways to be more creative. And so you’ve got a solution and I think you’ve offered some good insights for them as well. So thanks for your time, Gideon.

GIDEON: Thanks, Chip. I really appreciate it

CHIP: Again, my guest today has been Gideon Stein, CEO of Write Label

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