How to Fix Invoicing Issues and Get Freelance Writers Paid on Time With Matt Saincome From OutVoice [AMP 266]

Freelance writers know that getting paid can be difficult, and managers of freelance writers know why processing those payments is difficult to get paid on time or at all. Some companies don’t have simple invoicing systems or solutions for fixing what’s wrong with their invoicing processes. Today’s guest is Matt Saincome, Co-Founder and CEO of OutVoice and The Hard Times. OutVoice is a freelancer/writer invoicing platform that pays them with one click. Matt explains how to fix invoicing issues and get freelance writers paid on time.

Some of the highlights of the show include:
  • Payment Problem: There has got to be a better way, and now there is one
  • Publisher Problems: Tough business to make money, ad landscape has changed
  • Revenue-based Solutions: People don’t update/upgrade their tools elsewhere
  • Results: Businesses with inefficient tools, resources become rusted in place
  • Clicks and Revenue: Relies on effectively paying and retaining freelance writers
  • Mission: Waiting for check to pay rent? OutVoice positively impacts people’s lives
  • Paid or not on purpose? Reason is ancient, not automated/tiered invoice systems
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How to Fix Invoicing Issues and Get Freelance Writers Paid on Time With @MattSaincome From @OutVoicePay

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Transcript: Ben: How's it going? Matt: It's going well. Can you hear me okay? Ben: Yeah. I can hear you loud and clear. Matt: Great. Glad to hear it. How have you been? Ben: I've been good. I'm doing better with our invoicing issue when we started using OutVoice for sure. Matt: It's always good to hear. Ben: Yeah. How about yourself? Matt: Good. Busy as ever, but it's good to be busy when you're building things, right? Ben: Yeah, exactly. That's the idea. Glad to hear it. Thanks so much for coming on the show. I'm super excited to bring you on an episode. We've been super happy with OutVoice since we got rocking and rolling with the platform. It's really been a big game-changer for us. I'm really excited to have this conversation because I think that this is a topic that is under-discussed at least from the publisher side of things or in terms of actually solving some of these problems. We all hear freelancers complain about getting paid late or not getting paid on time, but I don't really see a whole lot of people talking about what they're actually doing about it. Matt: Yeah. That's definitely right. I've experienced this problem myself quite a bit as a freelancer. Collecting my check at the end of the day felt like a second job. Then, I became an editor. As an editor, I had to manage all these freelancers and all their invoices, and I realized that was a huge pain. It actually took a day out of my month at SF Weekly where I was the editor. I had to set aside an entire day just to handle invoices and admin paperwork. I actually remember that at SF Weekly, my editorial director came up one time and said, hey, Matt, I want you to start using this for your invoices. He pulled out this old, wooden contraption. I'm not lying. It had dust and cobwebs on it. This was probably a 50–100-year-old instrument, a wooden alphabetizer with flaps on it—A, B, C, D. He wanted me to print out all my invoices, sign them, and then put it into this thing to alphabetize it before I walked it down the hall to the HR person who was going to send out paper checks. I remember thinking to myself, regardless of the idea of printing out all this paper for no reason which is environmentally not the best idea, I am sitting on top of a mall in San Francisco, the heart of the tech world. People next door are probably working on AI to have self-driving cars, and here I am using a 100-year-old piece of equipment to do a simple task of paying someone $50 for a piece of work that we both agreed on, that's already done, and that's been published for two weeks. I just thought to myself, there has to be a better way. When I became a publisher myself, I started a publication with some friends called The Hard Times, a comedy publication. We started to have a huge freelancer base, and I thought, okay, I don't want my people, my freelancers, or my editors to have to go through the same problem. Okay, I'm going to google this thing. I'm just going to google, how do I pay my freelancers? I thought I would come up with something like Mailchimp. I thought there'd be an easy, obvious solution like, oh, here's the Mailchimp of publishing invoices. Not even close. There were some things out there that you bend to make work for publishing, but not really. A lot of times, they had stuff like monthly charges per seat for these freelancers who write one piece a year—all sorts of stuff. I'm a pretty stubborn guy and I didn't want this problem to hold down my publication, so I started tinkering and thinking of things, found my co-founder, Issa, and we decided to build it together. But I do think that, like you said, this is a problem that is not talked about very much. The problem is very clear—the way that content creators are paid for freelance work is stone-age-level [...]. It's nonsense. It shouldn't be done this way. There needed to be a better way. Now, there is one and my job is to tell people to go try it out for themselves if they're in that situation. That's OutVoice. Ben: Very cool. Just to keep the conversation rolling—and you've touched on this a little bit—what are some of the top problems that publishers and brands face when it comes to paying freelancers on time? Obviously, having tools in place is part of it, but beyond that. Matt: I would say that one of the main problems they face is that there are so many other more pressing problems. What ends up happening is as a publisher, every other month, you feel like you might go out of business. It's a tough business. The advertising landscape has changed. It's hard to make money so a lot of the solutions that are being pitched to publishers are revenue-based solutions. That makes sense because that's the fire that's in the house that they need to put out. I understand that because I'm a publisher and I'm looking for those solutions as well, but what ends up happening is people don't get around to upgrading their tools elsewhere. There are these really intense inefficiencies that fester in their businesses and their businesses become rusted in place, ancient, and not optimized. You can't go around expecting to win in a landscape like today with old-school, inefficient tools that waste your team members' time. I would say the biggest problems facing publishers are obvious ones, but the problem that we're helping is the fact that if you're going to compete and win in a more competitive, difficult landscape, you need to have your team focused on the most important task at hand. You do not want them wasting company time and resources doing repetitive, low-value admin work. OutVoice uses automation, CMS integration, and a more purpose-built invoicing solution to take a process that could take your team spread across 3 different departments 30–40 minutes and boil it down to a single click. At the end of the year, we'll even automate the 1099 sending out, the W-9 collection, and all that stuff. If you're like me and you're a publisher who is on a budget, obviously, yes, we want to get more money into your coffers. That's always going to help. But you also have to think about the efficiency of your resources. I know that this doesn't seem like a really pressing issue and I know people sweep it under the rug, but if you're a publisher and you're listening to this, what I would tell you is I started a publication with $800, I built it into something that millions of people read, and it was sold for millions of dollars. The way that I did it was not being inefficient with the tools that I used and building OutVoice as the engine. Very likely, you're doing it wrong. You might not know that because you haven't had editorial experience. I was at the freelancer stage, the editorial stage, and then the publisher stage. Every stage of the publishing industry touches this problem and has a hard time with it. I don't think they understand that the other parts of their business are also having a hard time with it. When you add up all those headaches, it's a problem that you shouldn't let remain in your business. If you can't tell, I'm actually a little irritated by this problem. This is an annoying problem. It's the sort of thing where you lose your talent. I'm a journalist. I have this great story. I go and I pitch it to Publication X, and they accept it. Awesome, cool. Now, it comes around to getting paid. I have to sign up for this weird, ancient system. I've got to print out something. I got to scan it. I have to send in some invoices. They don't give me a template. Two months roll by, you know the story, whatever. Where am I going the next time that I have a great pitch? If anyone else has paid me in a better way and respected my time more, I'm going over to that person. A lot of these publications are actually losing talent, and they're not really noticing it. What they do look at is their revenue. At the end of the month, they look at their clicks. Here's the thing about clicks and revenue. They come from the talent. You need the best people to write and create the best content, videos, podcasts, whatever it is. You need the best people to make the best content, to grow your audience, to sell the best ads, and to make money. The foundation of your business relies on you effectively managing and paying your freelance team, and you're not doing it. Ninety-nine percent of the time, you're not doing it. Stop doing that. Ben: I have zero doubt that you're correct when you say that 99% of businesses, publications, brands, or whoever are not doing this anywhere near the most efficient way possible. It seems like this problem just became entrenched as a [...]. Freelancers expect that it comes with the territory. People on the publishing side and the brand side don't really know what they would do any differently. Matt: Up until OutVoice, I don't believe that they had an easy, out-of-the-box solution that you could set up right away and get going like Mailchimp. Publishers know they need newsletters. Imagine if they had to build their own newsletter systems. I'm sure that they did at some point. Nowadays, they don't. Nowadays, there's a million different solutions. Mailchimp. I think Twitter's got something called Twitter Review or something like. There's a million out-of-the-box newsletter solutions. As a publisher, go ahead and type into Google, publishing freelance management and invoicing, and see what you get. Type content creation, invoicing, and management, and see what you get. You're going to get [...] like that's going to have a whole different, separate, and siloed workflow that your people are going to mess up. Look, you're going to gain some efficiency, I'm sure. It's better than absolutely nothing. What OutVoice does is it integrates the whole process into your normal daily workflow so that you don't need to run two different operations. It's the same button. You're going to hit the publish button anyway, you might as well hit the publish and pay button instead. It's a pretty obvious thing. In fact, I would argue it's not revolutionary. It's dumb. It's a simple, easy solution, and everyone should use it. It is the best way. The one thing I always say is that some publishers don't have this "problem," meaning some of them pay their people on time and well, but it's interesting when I talk to those people about how they do that. It's a lot of work hours. It's a lot of people. It's like an accounting team. I've written for a couple of publications that had an accounting team who actually went through the by-lines and did it all themselves. They would see what was published and then they would contact that person. They would collect their information, they would contact the editor, ask the editor how much did you agree to pay them for this, they would generate the payment, and then send it out. It actually "works" pretty well, meaning there's no problem. The problem is just that the publication is wasting all of those resources paying people to do this work that could easily be automated away. I will say this is better than nothing. If they're not going to use OutVoice, please burn a bunch of resources doing it that way so people get paid. Ben: I suppose from the writer's perspective, as long as the money comes in within a reasonable amount of time, that's all that matters to them. But as a customer, I will say that OutVoice does make this much, much easier. As someone who has actually gone looking for solutions, you're correct. There is nothing else out there. I've looked. There's nothing else that does exactly what OutVoice does as well as OutVoice does it. Matt: I'm really glad to hear that, by the way. When did we first meet? Ben: I think we first started talking about getting CoSchedule using OutVoice maybe six months ago. It was some time over the summer. I've been a reader of The Hard Times and I've followed you on Twitter for years and years. When I saw that you were going to tackle invoicing and you were going to fix that problem, I got really excited. Matt: You and six other people. Let me tell you, there are not that many people excited about this topic. It is a weird company to build because even the people who are responsible for doing this at companies don't want to change their systems because they don't care. They're like, you know what, I worked here from 9:00 AM–5:00 PM and I don't want to change the accounting system. I'm glad to meet a like-minded person who thought this problem was interesting. Ben: Maybe that says something about what I consider interesting. My hobbies are journalism, marketing, content creation, and so forth. Matt: The thing is there are journalists, writers, content creators, and photographers who are actually waiting for a check that will help them pay rent. I used to be one of those people. I know that it's not the most interesting, sexy company to build or whatever, but it's a company that fundamentally can positively impact people's lives. I've done some math on it. It looks like so far, we've saved freelancers somewhat around 200+ years' worth of time that they would have spent waiting for a check to arrive. That's a conservative estimate. I feel like it's a mission that we're on that I'm very passionate about, and I'm hoping to add more people to my mission. Every publication that we shake hands with and say they're going to start using OutVoice, there's a certain glee to it because I know behind that, there are 100+ freelancers whose lives are going to be positively impacted. Maybe one day, people will graduate from journalism school—or whatever degree that they get—they'll get into journalism, and they won't even think that freelancing used to be difficult. I actually know quite a few really talented writers who stopped freelancing, which I thought was really interesting. I was talking to some of them. There's a lot of stuff like the pitching is exhausting and that communication is a problem, but when you become a freelancer, you also end up running your own little small business. It's very difficult to do. There's always the admin work. Each different publication has a different system. One of the really interesting things about OutVoice is that if a publication uses OutVoice and they use the CMS integration—which they don't have to—as a freelancer, you could write an article. The day that it gets published, the payment could start heading your way. In just a couple of days, it would land in your bank account and you actually would have never had to create an invoice. You actually don't have to do anything. I don't know if I'm just the laziest person on earth, but as a freelancer myself, that sounds like a dream come true. When we get these new publishers on board, it's really exciting for me because I am a publisher but I was a freelancer first. I can't lie, a big part of the mission is to help these freelancers. It's a silly mission in some ways because the freelancers are ultimately not really the customer. The publisher is the customer. But it's good to actually improve an industry that you're a part of. That's what we're after. Ben: One benefit of improving your invoicing processes and one that's not immediately obvious but something that we touched on in this interview is what it can do to improve your relationships with everyone else who is a part of your editorial and content creation processes. When payments are consistently late, it can lead to a lot of arguments with regard to who was at fault. Those kinds of fiery conversations that come out of that often aren't very much fun for anybody. When you're able to solve the issues that typically lead to those problems, there's a lot of tension that just seems to magically go away. The benefits from this extend deep. They're deeper than what a lot of people even realize, especially if you don't realize how much of a problem this could be right now. When you get used to dealing with this kind of pain, sometimes, it can be really easy to not even consider the fact that a solution might be out there. As a result, it just becomes a part of existing, a part of doing your job. Beyond the benefits of just being able to pay people more quickly or more efficiently on time or at all, you can actually attract and retain better talent because you can make the pitch that you pay people super quick. That can be a pretty big differentiator. Beyond that though, you're not only going to be able to attract people and retain people, but you're going to have a better relationship with those writers. You're going to have a better relationship with your accounting and HR teams if they're involved at all. There's so much operational friction that OutVoice eliminates. There's no way to oversell the value of that. If you're wondering why this conversation matters so much or why I am so fired up about this maybe more so honestly than most topics that we cover on this show. I think that that's a big part of it. I think a big part of it is just because I've seen and I've experienced life without a functional invoicing process and life with an invoicing process that works awesome. I just think it's really worth taking a moment here just to reiterate how improving this process can yield benefits that are much, much greater than just getting people paid faster. Now back to Matt. It's interesting that you say that it's not revolutionary, it's kind of dumb. But I also think your comparison to what MailChimp did for email is really on point. I think that's a really great way of illustrating how transformative OutVoice really is. But when you think about it that way, when you think about building a newsletter platform from scratch somehow like managing your list and all the other things that— Matt: Why would you want to do that? You wouldn’t want to do that. Ben: Yeah. It literally sounds insane. Matt: Everyone goes and does that for their invoicing. Everyone goes and builds their own system. Google Sheets, walking down the hall, send it to so and so, email them this, tell the freelancer to scan their W-9 and email it to me. Dude, it's a nightmare. It's awful. Ben: Well, yeah. When we started bringing on freelancers here at CoSchedule, I mean we're hiring freelance content marketers and writers, so it's a little bit different from the news media space, the journalism space, but the process is the same. Matt: We have a bunch of customers like that who are brands and just content and operations in general. Ben: For sure. The instant we started, because the whole process was new to us in many ways, we immediately started running into all these issues with just getting freelancers paid and just with managing the internal bureaucracy of what is required to even manage a budget effectively. Just getting the payment processed expediently, it created so many problems that collectively were so painful. I don't know what we would do without OutVoice. Matt: You have better stuff to do. Ben: Yeah. Matt: Right? Ben: Absolutely. Matt: I don't spend all my time maintaining my weird strapped together or invoicing solution. If someone comes to you with a great piece of content, you want to publish that content. You don't want to go back and forth over email five times with the HR department about collecting their W-9 information. Is your address correct? You want to publish the content. You want to get all the admin work related to that content off your to-do list, and you want to move on to the next thing that's important for your business. That's what I was trying to do when I was a publisher. I just thought I could Google and find someone who had built that and I couldn't. It's interesting, I'm glad that you enjoy the product. One of the things is we actually haven't lost a single paying customer. Ben: That’s amazing. Matt: We had one company go out of business, that's the only person who's stopped using OutVoice. I think the reason is, well, first of all we throw away more customers at it. Let's be frank, there's a data problem there. When we have 10,000 customers, I think we're going to lose a couple. But I think one of the reasons is the other way is so brutal it's just so painful, why would you ever want to go back? My dad actually sells air conditioners, he and my mom put me through school doing all that sort of stuff. He said something interesting to me which was one of the main things that people like to buy or keep using is to get themselves out of pain. A pain killer and being hot is uncomfortable, so I'd like to buy an air conditioner. I think in publishing, the admin, invoicing, emails, back, and forth for certain personality types is very painful. There's a type of person who runs a publishing business who actually doesn't have that much experience in publishing. They were never part of the editorial system. It’s a little confusing how they get to be the publisher. They're like, yeah, I used to run a used car place, now I run this magazine. I don't know, whatever. Someone buys a magazine and puts them in charge of it. I feel like they don't know the inner workings very much. Sometimes they actually don't know the pain that their team is going through. They actually have a hard time figuring out why they should buy this thing. When I started to realize that, I started to realize, okay, that's part of the reason why this problem has existed for so long. It’s because I was a publisher, but I'd also been a freelancer and I’d also been an editor. When you really think about it, if you're a publisher who doesn't have that much experience being a foot soldier or whatever, in the trenches, it makes sense. You might just say ultimately that people get paid. You just keep going about your day. A perspective thing. Ben: I think that you're definitely in a unique position where you're able to connect the dots and understand what this problem feels like from all different perspectives, which I think a lot of freelancers don't necessarily see the editor’s side. Ben: Editors might see a freelancer’s side, but the publisher, whoever, CFO, whoever they're dealing with doesn't see anybody's perspective. Matt: One of the things is that I feel like the freelancers often think it's so painful for them, but actually most of them, a certain percentage of them actually think that it's purposeful, which is an interesting thing. I've done a little bit of research on this. I've talked to thousands of publishers. I would say something like 5–10% of them, it is a little purposeful. They're not sending the money because they have some sort of cash flow issue. They're using you like a credit card. They're trying to get the work out of you and pay you as low as possible to help their cash flow. But 90–95% of publishers think that is not the situation. It’s interesting though because if you ask freelancers, they would assume that that is a much larger chunk of the pie. It feels so painful. It’s like, why would it be this way unless it was on purpose? Why don't these people want to pay me? But the truth is, you look at how much content is published by a modern publishing company, a modern content operation, and you imagine the amount of emails and back and forth that are generated for each one on the old school accounting systems, just do the math. It's something like, okay, our company's going to publish 50 pieces of content a day. Each one of those pieces of content is going to require onboarding of a freelancer 20% of the time, a back and forth invoices are improperly filed 10% of the time. Pretty much, 50 pieces of content is going to create 250 email threads with all of your employees looped in from various different departments. That's just one day. The next day comes, the next day comes, it creates this gigantic pile of work. That is actually the main reason why freelancers are not getting paid. It's not because the organization doesn't want to pay them. The organization doesn't have a real efficient way of doing it. That's why we had to build OutVoice. My company would've been the same way. I mean particularly because I'm so small, I would’ve been one of those companies who was like, oh [...], sorry, I forgot to pay you. Because it created all this mess. That's why you need automation. I would say you need automation and you also need tiered account administrative access. You need to be able to delegate out things to people in the know, which is one of the key things OutVoice does is it allows people who are in charge of certain departments and who have all the relevant information to make decisions and then have people who oversee the sending of money, like accountants, oversee all of those decisions in real-time and flag or stop any of the ones they find problematic. Now here's the really interesting part and I'm going to probably have spent a couple of accounts here. Most of the time in the publishing industry, the people who are in the HR department or the accounting department have pretty much no information and have pretty much no interest in the information related to these freelance payments. What ends up happening is an editor and a freelancer come to an agreement, I'm going to pay $200 to write this piece of content. Then, you add in a third person to the conversation who knows nothing and turns to the one who says, did he say he was going to pay $200? The other person says, yeah, that's what he said. He's like, okay, I'll go talk to someone else and I’ll get that person to pay you. You just add in all this nonsense. With OutVoice, what we do is we say, if the publication’s representative is this editor or this manager of content, they've come to an agreement with the freelancer over email, over whatever, I'm going to pay this amount of money for this piece of content. Go ahead and let that go into the queue. Let the accountants see that in real-time logging into their OutVoice account. If the accountant actually has an issue or problem, the accountant has all the information right there—the time that was agreed upon, the editor, the freelancer. They can flag it. They can email these people. You want to know the result, 99.999% of the time, the accountant has no issue. They care about overall budgets, which you can set in OutVoice. First of all, they don't care, and they don't know. Their job is just to put a rubber stamp on things and that's it. They might want to see if all the payments are coming through the line. Hey, look, it looks like we mostly pay people between $250–500, but this one's worth $5000. I'm going to email this person and see what that's like. In OutVoice, you can pre-determine, as a publication, your own standard of safety period before the payment actually goes out. It could be seven days. It could be three days. It could be whatever you want. You could see that one come, it could be flagged. You can say, I'm going to talk to these people about this thing. But one of the ways we gain some of our efficiency is we delegate powers to the appropriate people, which is how it always should have been but I don't know. As an editor, I remember being an editor and being like, this is so weird. They had me print out my own invoices and sign them myself. There are so many steps where it’s like, what are we doing here? Ben: Yeah. It seems like we do it this way because this is the way we've always done it. Matt. The thing is with automation and just—this is going to sound silly because computers can do a lot of things better than we can. You can have OutVoice just say this payment looks differentiated. You normally pay $250 and this one's $2500. That's better than me printing out my own invoice and signing it myself. It's just a weird thing to do. Ben: Yeah, absolutely. Something that we haven't really touched on yet is that I think is maybe an overlooked benefit. Using something like OutVoice or even just committing to improving your invoicing process, in general, is what it can do to improve working relationships between people? I'm just going to be transparent, I mean internally, this has resolved so many minor interpersonal disagreements. Just because I wasn't able to see finance’s side, finance had no reason to see my side of things. Just because there's so much context that they don't have that's really needed in order to understand why this problem— Matt: Yeah. If they're really curious, they can come to you and they have all the information on their OutVoice account. The truth is they're not going to come to you. They care about it's $5000 a month on the blog or whatever. This month it's $10,000, can you ask him why? That's the sort of question that they don't need to know what $75 payment went to. It’s like, hey, was that 350 words or 450 words? Another thing that you said that is really interesting to me, an interesting stat is there's a study recently and I'm going to quote it off the top of my head. It was something like 60% of people would agree to a pay cut if the tools they used at work were less frustrating. I think that's what you just expressed, not that I want you to get a pay cut. People get frustrated by their tools. If you have better tools, you're going to like your co-workers a little bit more. You're going to like your job a little bit more. One of our biggest customers has told me they got into OutVoice for the efficiency, the factors built for publishers, et cetera. But one of the main things they feel about it and that their people tell them about it, is that it's a talent attraction and retention tool. For them, it helps them attract freelancers. They actually publicize. They say, hey, make contact for us and we’ll pay you OutVoice. It's better than any other way that you get paid, which is pretty interesting. People who actually are in charge of it—people like you—are more likely to enjoy their jobs or stay, because they use better tools. I mean it sounds pretty simple, but I think if you were to ask me, I wouldn't expect it to be that high. That study was pretty revealing to me that people were actually saying, look, this is so brutal. I would take less money if it was easier. I think the same thing was true in a different study where people—similar to commutes. That people would take less money if they didn't have to commute because the commutes are so brutal. Look, man, we got to move forward a little bit here. We can't just have brutal tools and processes for our work lives forever. We have to improve some of the stuff. The shiny, interesting, and flashy parts of our work lives do get improved. As a publisher, I've got some pretty cool ad tech. I've got some pretty cool newsletter software. But I think that particularly in publishing, there's a lot of stuff that's rusted in place and hasn’t been updated in a long time. I'm sure there are other industries like that. My whole background is in publishing. But it feels good and important to go and clean up some of the stuff that is a little bit under appreciated. Ben: Yeah, absolutely. Just thinking of a small setback, just because it's something I'm curious about. Like I said, OutVoice is a game-changer on multiple levels for us, both in terms of just the mechanics of getting people paid on time or more quickly and all the benefits that come with that. Then also, just being able to make internal workflows easier and then actually improving people's working relationships as a result of not having to fight over some of these things. Is that something that a lot of customers have told you or something that you hear often, or is that more the interpersonal side of it, is that a little subtle benefit? Matt: We just put out a customer survey. I think you are the first person who told me this thing makes me dislike my coworkers a little less. I think that's the first time I've ever heard that. I think that people have said it in a little bit more vague ways. They say stuff like it improves our process. It improves our communication, these sorts of things. But when you say it like that, it's actually interesting because I think that happened at my publication. I've never really thought about that before. But because I was the publisher, I think I was a bit of a bottleneck. I think that it probably did. Probably people are a little bit less upset with me because OutVoice is out there automating a bunch of stuff that would be piling up on my desk. Actually, we’re very lucky. We're working on some pilot programs with some very large media organizations. I was talking to one of the biggest media organizations in the world, and they said that their freelance payments ultimately were signed off by their VP of finance and that they went on her desk. I thought that was so weird. She is probably (based on her title) an incredibly busy person, but there are probably people all around the organization who are upset with her and waiting for her to sign off on something. You know what, when she signed it off, do you think she's doing very much investigating? No. She's not really a party to a lot of these things. It would be much better for her if she could have an account where in her free time, she could go and look over all the different transactions and flag any of them, set budgets, all that sort of stuff, but not have to actually have people upset with her that things are piling up on her desk. It's one of the good things about automation. Bad things about automation, it might put all this out on the street. We might all lose our jobs. Good things that might make people like us a little bit more, in the meantime. Ben: For sure. It could go in one of two directions. Matt: Eventually, the OutVoice automation AI bot will start trading its own publication. Ben: And paying itself. Matt: Paying itself. It will start publishing just insane radical stuff that feeds into Facebook's algorithm. Next time you see me, I'll be trying to pull wires out of it, please make it stop. Ben: Well, hopefully, you're able to solve some problems for some people before technology swallows us all. One last question I'll throw your way, for listeners of this episode, if any part of this is really resonating with them and they're maybe trying to think, maybe it's time that they walk at or maybe just honestly asking do they have any problems with their freelancer invoicing workflow, where would you recommend that they begin looking? If they're not acutely feeling this pain or maybe they are but they were never aware of it before because they just assumed this is just the way things are done. I'm not even going to consider trying to fix this because I just assume that this is just how it is, like death and taxes almost. Where should they start? Matt: Well, I would say, if you have freelancers and you're trying to organize them in a way where you can grow that team confidently, even if it's not right now, but maybe that's in the future and we try to start with a nice clean base, I made it so that OutVoice has some plans that are truly like $39 a month or something. It doesn't matter. For most publications, that should not matter. It's a very small sum. I would say similar to if you're starting a MailChimp newsletter, you wouldn't want to start your newsletter on your own Gmail list or something like that and then transfer it over. You really want to get a nice clean organization going from the start. I would say if you have freelancers, and let's be a little bit general here. If you have freelancers, generally speaking, content creators are great, but if you just have a freelance team that you would like to manage and pay, and you like to automate away a bunch of the work including the collection and onboarding of W-9 information, and at the end of the year setting out the 1099s, I would go to But if you’re listening to this, I love talking to entrepreneurs or business people. Feel free to reach out at and we'll hang out and we'll talk. Ben: Very cool. If people want to find OutVoice on the web or if they want to find you online, where are the best places for people to go look, beyond just maybe sending you an email? Matt: Sure. and you can follow me on Twitter @MattSaincome. My name is spelled Saincome, not Samcome, which is how a police officer recently spelled it on a ticket, which cost me $400 because I couldn't figure out how to pay my ticket. It wasn't populating in the field related to—I went online, I was like, I want to pay my ticket. He’s like, you don't have any. I go, that's weird and then I get mail. You owe us another $200. Now your license is going to get suspended. Anyway, @MattSaincome on Twitter, come hang out. I apologize if I'm not always the most professional person there. I just like to have a good time, but hopefully, you enjoy it. Ben: Awesome. Do you think that maybe parking tickets will be the next problem? Matt: You know, there's a great company called Do Not Pay and I really admire their founder because what they do is they fight bureaucracy with automation. It’s a great, great company. I'm really intrigued by them, but it's all sorts of stuff like parking tickets. All these things where, hey, you got to call us between the hours of 9:00 and 10:00 AM on Tuesdays and Wednesdays. All that stuff is just weird, painful parts of life where bureaucracy just bears its weight down on you. It’s a robot hero. I think that they have like 200+ services that they do now. It started with parking tickets, but they really branched out where its electric bills. Anytime that you're really just kind of being abused. I feel like every once in a while, you just get put in the wrong stack, like your piece of paper just kind of gets messed up or whatever, and then there's no way to get out of it. It seems like that's what that company is for. It's called Do Not Pay,, I believe, I would recommend it. Ben: I thought I was making a small joke, but that actually does sound super interesting. I'm going to go check them out. Well, Matt, thanks much for taking the time to come on our show and just talk all things invoicing. Matt: Thanks for having me. Ben: Yeah, absolutely. I think, like you mentioned earlier, this issue is not maybe consciously at the front of everyone's mind, but it's a problem that a lot of us deal with or have dealt with. I am just really excited about what you're doing and what you're working on to solve a lot of this stuff. Matt: That means a lot to me and we recently raised some money, and we have a bigger development team than ever. Please, you personally, feel free to reach out, and as you continue to use the product, if you have ideas about how you like it to go, let me know. Ben: Yeah. Will do, absolutely. Thanks for coming on.
About the Author

Ben Sailer has over 14 years of experience in the field of marketing. He is considered an expert in inbound marketing through his incredible skills with copywriting, SEO, content strategy, and project management. Ben is currently an Inbound Marketing Director at Automattic, working to grow as the top managed hosting solution for WordPress websites. WordPress is one of the most powerful website creation tools in the industry. In this role, he looks to attract customers with content designed to attract qualified leads. Ben plays a critical role in driving the growth and success of a company by attracting and engaging customers through relevant and helpful content and interactions. Ben works closely with senior management to align the inbound marketing efforts with the overall business objectives. He continuously measures the effectiveness of marketing campaigns to improve them. He is also involved in managing budgets and mentoring the inbound marketing team.