Jason Chicola Weighs in on How to Make More Money as a Freelancer

Jason Chicola

A founder of UpWork and Rev, both online businesses, Jason Chicola shares how writers can earn an income online.

UpWork is a platform that connects freelance writers and others with clients.

After years of working directly and indirectly with freelancers, he is convinced that the gig economy is steadily growing and paying well.

In this interview, discover:

  • How to succeed in a gig market
  • Two ways to create a successful writing business
  • Why he believes opportunities continue to grow

And lots more.

Listen Now

Transcript Below

Bryan Collins: Great? Okay. So, we'll make a start. So, my first question is Rev is a service that I have decided to use a lot as a writer and I'm wondering, why did you decide to create Rev and use Temi in the first place, and I hope I pronounced use Temi correctly.

Jason Chicola: So, it's a bit of an indirect story. Are you familiar with a company called Upwork?

Bryan Collins: Yes, I am. I use Upwork quite regularly too.

Jason Chicola: Yeah, so I helped to found Upwork in 2004 in California. Upwork and Rev have a lot of similarities. Both of them are internet businesses that connect people who want to work from home with people who need work done. In the parlance that I use, we say they're both labor marketplaces. Upwork is a lot like Ebay in the sense that you can buy or sell any kind of service, just as on Ebay you can buy or sell any kind of good. On Upwork, there's not a lot of curation, so they largely operate on the principal of caveat emptor, buyer beware, that as the buyer, you have be careful to hire the right person and you may not get what you want, although there's great people there and they do great work and there's a lot of success. Rev is actually a large Upwork customer. We spent, I'm sure, over one million dollars in Upwork.

Jason Chicola: When I started Rev in 2010, it was because I really believed that many, many people want to work from home. I think if I look out 50 to 100 years, or by the time that I die, I expect that there will be like a billion people who work on the internet through a computer rather than getting in a car, driving to an office. So, I view the shift from working in an office to working from home as a mega trend in our lifetimes and as an entrepreneur, that excites me. As a human being, it also excites me because when I spend time with people that work from home, what I find is that they're happy, grateful, appreciative. They love the control that it gives them and my initial motivation was to create that feeling for more people.

Jason Chicola: So, I knew I wanted to create work-from-home jobs and I also knew that the key challenge of Upwork was that they don't and couldn't guarantee quality. So, I started with the premise of how could I create work-from-home jobs, but I want to pick categories where I can guarantee quality for the customer, because if I do that, it'll stand. If I do that, every customer will use it. On Upwork, the most common type of work is computer programming and yet the best companies in the world, like Amazon or Google or Microsoft, don't use Upwork for their programming. So, it's clearly not the best way to get programming done.

Jason Chicola: My thought is, I wanted to create a category of remote work where we are the best way to do it, and we can eventually be the leader. I then looked at what are the kinds of jobs you can do from a computer, over the internet, and have it be a really good experience for the customer and I stumbled on services around language. The first service that I tried was translation. The second service I tried was transcription, and transcription took off a lot faster, so we've really gone deep there. Today, we offer audio transcription, closed captioning of videos, foreign subtitles of videos, so I want the words on my video to appear in Spanish or Mandarin at the bottom, and document translation.

Jason Chicola: We also, as you're aware, have an automated transcription service that's called Temi.com. That started as an experiment to see if anybody would want to use a transcript that was, call it 90% accurate rather than close to 100% and to our delight, it turns out there's a huge market for that as well. So, we have two offerings for transcription, a higher end one, Rev, that costs $1 a minute, where the transcript is … we bill it 99% accuracy. The less expensive one, Temi, 10 cents a minute, 90% cheaper, where the accuracy is around 90%, but the caveat is, if you have really clear audio, like a podcast, you might get to 97% accuracy. If you have lousy quality audio from a coffee shop with a lot of background noise, it could be much lower than that.

Bryan Collins: Okay. Yeah, I haven't used Temi before, but I've used Rev and Upwork quite a lot. The way I use Rev is for an interview like this, I will get it transcribed and it will help me write an article faster. In the past, I've also dictated or narrated chapters of books into a Dictaphone and then uploaded that to Rev to get transcribed, and I find that can help with things like [inaudible 00:08:06] and even writer's block, because you're not hunched over a keyboard or sitting at a computer. So I'm just curious, what are the typical types of customers or people who use Rev and what are they using it for?

Jason Chicola: It's incredibly diverse, and I'll walk you through some of the more common use cases. But, this kind of surprises people. There are many needs for transcription, as you can imagine, because who is it that wants to know what they said? Who is it that wants to know what other people said? Who is it that wants to speak rather than type? The answer is nearly everybody. If I start to break down what are the largest categories of Rev customers, journalists come to mind for sure. As you well know, many journalists will record a subject, like you're recording me, and then use the transcript to help them write the story, both because it helps them to pull quotes. Also, because it helps to refresh their memory in the moment before they write the story. That's quite common. Market research is another large segment. Market research firms tend to do focus groups and interview consumers about how they feel about Coca Cola versus Pepsi, and they will transcribe those focus groups so their clients can study what consumers say and feel.

Jason Chicola: Video production is a big category for us. In fact, if you went to CNN, you'd find that there're hundreds of people at CNN that use our services. If you're in the process of producing media and videos, there're many needs for our services. First, you might transcribe the raw footage so that … if CNN is trying to make a five minute news clip, they might go and record 10 hours of raw footage. The producer, who's editing that video, doesn't want to go through 10 hours of footage. They want to scan the transcript, find the quotes they like, and then quickly pull the video clips that are appropriate and edit it down. Later on they can use captions and so forth, but I'll focus here on transcription.

Jason Chicola: There are churches now that transcribe sermons quite commonly. We have companies that will transcribe board meetings. We have found that a lot of prisons will transcribe calls from inmates to people outside the prison. This is a small use case, I'm just giving you an example that shows the diversity of use. Lawyers. It's quite common to transcribe things that happen not just in a court room, where it tends to be more specialized and often provided by the court, but nearly anything that's done for legal purposes, any conversation is going to get transcribed. In the US, we call them depositions. I'm sure they have similar things in Ireland.

Jason Chicola: We're seeing also some categories that may have been small in the past that are picking up. For example, law enforcement. Law enforcement police departments, there are certainly some calls they'll have that they transcribe. You can imagine somebody calling 9-1-1, or I don't know what you guys call it over there, emergency services, but beyond that, there's a trend in the United States for police officers to wear body cameras. There's been controversy over what happens when a cop, God forbid, shoots someone, what happens. So, there's a trend toward saying, “Hey, every cop should be wearing a camera at all times,” and that camera creates a record of what happens. You can imagine, some of those recordings, they would want to submit them as evidence for a court case during, let's say, an arrest.

Jason Chicola: So, there's really a wide range of uses. Do you want me to get into the productivity side as well or does that …

Bryan Collins: I suppose I'm curious, how would somebody get maximum value from their transcription? What's particularly intriguing is what you said there about CNN using it to find interesting quotes. That's the way I've used it for interviews as well. Typing up a 30 minute interview can be quite time consuming, but it's great to have something that you can scan and pull things out. So, would you have any recommendations that you could give to somebody who's either a video blogger or somebody who's writing something, how they could get maximum value from the transcription, or even prepare an audio file for the perfect transcription?

Jason Chicola: Sure. Well, let me start at the beginning. The most important thing to keep in mind if you want to get value from your audio from transcription is that the better you record the audio, the better results you're going to get. This sounds obvious, but it's sort of garbage in, garbage out. If you haven't done this, I would listen to a couple of recordings and it's a simple rule of thumb. If you have a hard time understanding what was said, the transcriptionist will have an even harder time, because they didn't have the benefit of being there and they probably don't know as much as you do about the topic. So, there's a couple simple rules of thumb we would give people. You want to minimize background noise. You want to use the best recording equipment you can. The iPhone is actually okay if you're doing it in a controlled environment. You don't want to be crinkling a lot of papers and food packages next to the microphone. That creates a bad experience. Certainly doing things outdoors with cars going by is unhelpful.

Jason Chicola: So first thing, create a clear recording. That's going to help you all kinds of ways. Beyond that, once you have a transcript, I would point out to people, it depends on your use case, but we have what we call an editor. We have software that we provide for free with our transcripts that has a number of features that I think can be useful to people who are in, let's say, the media space, as you are, and probably some of your readers are trying to get value, you can highlight valuable quotes. You can share the transcript with other people to whom it's of interest. We have a feature that's going to launch in the next week or two where you can make comments on the transcript.

Jason Chicola: So, most people producing media do it on teams and the software that we provide for free, for no additional charge beyond the transcript, is designed to allow teams to collaborate on the transcript meeting. You can read it, discuss it, say, “Hey, here's this quote, let's use it for this part of the article or for that part of the article.” Of course, the transcripts that you get, you can connect them to the video. There's one other important, I think, announcement. I can give a little reveal here. You might be aware that we charge for time stamps. Well, we're going to, starting early next year, probably before [inaudible 00:15:40], we're going to provide free alignment, which means that when you are reviewing your transcript, even if you haven't paid for a timestamp, we will show you for each word or sentence in the transcript where it corresponds to the video.

Jason Chicola: So you can either play the video at any part into the transcript, or you can look at the part of the transcript and see where that video is or the audio is. If you're producing video or audio, that can be quite helpful, to know where it lines up, because imagine you have a one hour recording. That could be a 25, 30 page transcript and it could be very hard to connect the right sentence to the right part of the video or audio.

Bryan Collins: Yeah, I can see how that could be useful. Sometimes I've listened to an audio file and tried to match it up to the part of the transcript so that I could make more sense of the context that the interviewee was referring to.

Bryan Collins: I was also intrigued by something you said there at the start of the interview. You talked about how maybe up to a billion people in so many years' time could be working from home. So I'm just wondering, what tips do you have for somebody who's working from home, because I know a lot of writers and creative professionals these days tend to work with different people, like their editor, around the world or perhaps they work in a library or perhaps they work by themselves. So, what advice would you offer somebody like that?

Jason Chicola: Well, let's see. You know, there're different ways to work from home. One of the unique things about Rev, which is a different kind of platform. Rev is for people who make a living typing. Rev is designed to make it so that the freelancers don't have to ever apply for a job or bid. I think the reality of freelancing, for most people, is that you're constantly selling yourself to find your next project. So, probably the first thing I would say is if you're going to make a business freelancing, not on a platform, but finding your own clients, you need to think a lot about your social marketing strategy from the start. You're going to have to spend somewhere between 10% and half your time not on doing the work, but on lining up job opportunities.

Jason Chicola: So, I think that has a couple implications. One is it means the kinds of people that will be most successful in that individual freelancing lifestyle are going to be people that not only are good at selling themselves, but enjoying it. If they don't enjoy it, you might look into finding a platform that you can work for, and there are platforms for writing as well. I'm happy to give you some names of ones that I'm aware of, there's a lot. In a platform, you'll typically probably earn fewer dollars or whatever the currency is, per job than you might directly, but you might spend less time looking for work. So, it may end up better in the end. It may end up worse in the end. You'll certainly have less flexibility probably because you'll have to work with the rules of that platform.

Jason Chicola: So, I would consider a platform working for a middleman, if you don't enjoy selling yourself. If you want to be independent, which is obviously quite admirable, I would probably suggest trying to come up with some kind of specialty or niche where you can be a known expert or quantity in whatever your niche is. It's a big world and it would probably be better to be known as the go-to guy for some relatively narrow topic than to be known as a freedom writer for anything, but not known for one thing in particular. Then, part of, depending on the way you approach things, I would definitely think about trying to build an online presence for yourself as an authority around that topic, and ideally it's some combination of whether it's blog posts or YouTube videos or Twitter with a lot of followers. I mean, I think people that develop a following in a relatively specific area, that can be the foundation of a successful freelancing career.

Jason Chicola: So, that's probably one path I think is good. The other extreme path is to not have a persona, but to be on a platform. So, I think those are two very different strategies that could probably both work.

Bryan Collins: Yeah, I know what you mean. So, if you're on a platform like Upwork, you don't have to necessarily worry about marketing yourself, perhaps through content marketing or blogging. Do you think the gig economy is going to get bigger over the next few years or will the gig economy dry up?

Jason Chicola: I think there's no question that the gig economy has grown a ton. It will continue to grow a ton. There's probably some differences by category. I think that content marketing, which is the category to which writing is the most closely related, has had its share of ups and downs. I would not say I'm an expert in it, but I think I've heard … so, let me park and then come back to it. If I look at the gig economy broadly, Uber is a part of the gig economy. Ride sharing is growing a lot and will continue growing. What Rev does, transcription, is growing a lot, will continue growing. Many entrepreneurs are looking every day for other categories of work that can be done online. I've recently seen quite a few companies that are doing English tutoring online, teaching people overseas to speak English. That category is growing a lot. There's a company in China called VIP Kid that is quite large. I believe Bloomberg reported that they're doing more than half a billion dollars a year in revenue.

Jason Chicola: So, I think there's no question that gig economy is going to grow a ton. All these companies have lots of venture capital. They're improving their platforms. The reason why the gig economy works is, because there are lots of people that have time where they'd like to work and they'd like something flexible and the gig economy provides more flexibility than a traditional job, both in terms of when you work and where you work. If you ask somebody, would you like to set your own hours and be able to work wherever you are, people say yes, of course. The gig economy provides that in a way that traditional employment does not. So, that underlying … those two factors, I think are so powerful that there's almost nothing that I think could slow down the growth of the gig economy on an aggregata basis because you're not going to change human nature. You're not going to change the fact that people want to work when and where and how they want.

Jason Chicola: If we look category by category, country by country, you could certainly imagine a scenario where some country might ban Uber and that might slow the gig economy down in that country for a little while. Eventually, the market will probably may make it possible again, because there's a huge demand for those services. Content marketing, I think, has … and by content marketing, I'm talking about paying people to write articles. I think that has a somewhat checkered past in the sense that a decade ago there were a lot of companies that provided these services and the customers were buying it, were having articles written not so much because they wanted to read them or their customers wanted to read them, but they felt that by putting these articles out there online they would get ranked higher on Google's organic search and Google has obviously changed the way they do their search rankings many times and a theme of those changes is that they reward content that readers really enjoy and they don't reward crappy content.

Jason Chicola: So, I think that's led a lot of people and brands to do more content development in-house, where they can more tightly control it and create stuff that the readers are going to enjoy. So, I think that trend has caused some content marketing platforms to fail, I think. So, like I said, there're questions marks about content marketing's category, but the gig economy broadly is a huge success that I believe shows no signs of slowing down.

Bryan Collins: Sure. Jason, I remembered all those article directories people used to submit, 300 and 400 word articles to that didn't really add any value, but they just helped the person submitting the articles to build links and potentially rank higher. Obviously that doesn't work anymore. I'm finally, as somebody who's set up or helped set up a couple of different companies, I'm just wondering, what's your number one tip for focusing on a project and not getting distracted by different projects?

Jason Chicola: Boy that's a hard one. But, I'll tell you my personal favorite tip and then maybe I'll give a book or two. I think that multitasking is kind of overrated. I think that there are some people that pride themselves on being able to do 10 things at once, and I think that those people are lying to themselves. I think that we're increasingly living in a world of constant distraction. You can always pull out your phone and check your email. People get obsessed with Facebook and Twitter and feel the need to check Facebook and Twitter 100 times a day and that's good for Facebook and Twitter, but it's probably not good for you. I would encourage people to have one big priority at a time, ideally for a whole month, and to think a lot about what's the one thing that if you accomplish you're going to be professionally or personally better off a month from now and put all your resources behind it.

Jason Chicola: For example, personal example is last month I was working on kicking off a process to hire an executive for a function that we need some help in. This month, I'm focusing on our annual planing process, setting up goals and targets and strategy for next year and if other things slip, that's okay. So, I think it's easy to say not a priority, but the hard part of having a priority, the flip side of it, means saying no to a lot of things. It means being okay with letting other things slide. People that are ambitious or have high standards, often want to be perfect at everything and trying to be perfect at everything is actually the opposite of being able to focus.

Jason Chicola: To focus, for one thing, you have to say no to everything else and you have to be okay with telling somebody, either not responding to an email or telling somebody, “Sorry, can't do this. [inaudible 00:27:08].” Or you might have other projects that in the past you've worked on and you have to tell yourself, “You know what? I'm going to ignore those for this month while I'm working on writing my book, getting a new job, finishing one big project.”

Jason Chicola: So I think a lot of people, it often takes adjustment, almost psychologically, to be comfortable with letting go of other things, breaking the commitment with yourself. If you believe you in that top priority, whether it's writing a book or getting a job or finding a project, if that's the top priority, you should tell yourself it's okay if some other things slip. I think getting mental clarity around that, and then another tip, when you're coming to work in the morning, don't check your email first. Don't check your slack first. Work on your priority first.

Jason Chicola: Personally, I find that to be huge, because what tends to happen is people go down the rabbit hole of emails or, God forbid, social media, and you could spend all day looking at emails and all day looking at Facebook and Twitter and accomplish nothing. I think the people that are most effective are people that come in, quiet, clean sheet of paper, work on the top priority, sometimes with the internet off. I find that some of my most productive time is if I'm on an airplane without WiFi and there's no distraction so you can make a lot of progress on your chief priority.

Jason Chicola: So, I think we live in a world of overstimulation, where my high level suggestions are be clear of what your top priority is, and shut off distractions so you can work on it. Last thing I would say is anybody who wants to be more productive, I would recommend the book, “Getting Things Done,” by Dave Allen. I think it has some great time advice of how to be more productive and how to improve those habits over time.

Bryan Collins: Yeah, that's a great book. It's actually one of the first productivity books that I read Jason. Where can people find you online?

Jason Chicola: Well, they could email me, jason@rev.com, or they could find me on Twitter @jasonchicola. Chicola is spelled C-H-I-C-O-L-A.

Bryan Collins: Thank you.

Jason Chicola: Thanks Bryan.

Get your 101 writing prompts today

Need help getting started writing? Use these proven writing prompts. I'll also send you practical writing advice and more as part of my newsletter.

Powered by ConvertKit

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.