150: Become a Digital Nomad with Indiana Gregg

Indiana Gregg is a tech entrepreneur, singer-songwriter, and the Founder & CEO of Wedo – the world’s first commission-free social freelance platform. We discuss the pros and cons of being a digital nomad, easy ways to get people to switch to your platform, and how to use network effects to scale your business. 

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Become a Digital Nomad with Indiana Gregg

Our guest is Indiana Gregg, the founder and CEO of Wedo, the world’s first commission-free social freelance network. Indiana, welcome to the show.

Thanks for having me, Steve.

So, Indiana, you told me that you started your career as a musician, singer, songwriter. So how did that turn into an entrepreneurial venture running a social freelance network? What’s the winding path that led you there?

Well, I actually started in digital industry, working building websites and working on digital assets for companies. So I started at Sony years ago and I worked as a freelance consultant following that for a while. So I kind of did music in between, if you will, because I was already an entrepreneur and then I went into music. And the music journey was interesting because I was launching an album, I had a label deal, during a time when the music industry was in real trouble with piracy and the digital downloads and the RIA suing individuals for pirating music. And so it was an interesting time to be a technologist as well as a musician. So I decided, you know, I did my album and I went on tour and I decided I was gonna fight the pirates.

So I built a platform, a marketplace for the music industry and went around to all the houses, all the labels and brought on some catalogs and negotiated with the labels who thought that music would never be streamed. Everyone would always want to have a physical download and just kind of being present in those arguments with the likes of Universal and Sony and EMI and Warners and all of the majors and fundamentally built out a platform for the industry with artists and labels and managers and licensors and same people, publishers, etc. And we built that up to around 14 and a half million users and we were just really one of the early early players who were paying on a rev share model, an advertising model for streams of music. And you know other popular sites at the time were MySpace, iTunes, Apple Music didn’t exist quite yet. They’d launched, I think, the 99 cent download in America. But we were projecting and we were sure that streaming was going to take over the world within the music industry and we were right. So that happened that way. And following that, I started a couple other companies.

One was just a non-technical company and I became a consultant after that and eventually had this idea of building Wedo to help solve a similar problem for the future of work, slightly different but a very similar problem in the market where nothing exists to service a mass piece of market. And that really is the journey, you know, going from various types of technologies and building things. You know, the music was kind of a detour that led me into probably what my passion, my real passion is. I love music, don’t get me wrong, I love being a musician, but I didn’t see it as a long-term goal. I quickly found my place in building marketplaces and networks and building applications is really where my heart is. That’s what I love to do.

Okay, that’s fascinating. And it’s also interesting that the social networking concept has come, it came to you pretty early and you stuck with it. So why do we need a new network. So, you know, people are familiar with Fiverr, with Upwork. What’s wrong with these networks?

Well, the real problem for people in general is nobody wants to work for the man anymore. We’ve got a whole generation of millennials, X-Y-Zers, you know, coming up who really want to have the freedom of flexibility to work where they want, when they want, how they want and don’t particularly care for the traditional nine-five or the industrial type of work that we’ve had over the last century. That’s one of the issues. So, sites like Upwork and Fiverr fill the gap for the freelance and independent worker, the self-employed for a while. The issue with them is that they take major pieces of commission.

So, 20% on the first $500 you make per client. And that’s frustrating. But not only that is they keep you in isolation in the sense that there is no social infrastructure for that. And when you think about social networks like Facebook or Instagram or LinkedIn, they all have their niches. And there’s a big hole in market for the self-employed and the independent worker. And not only that, is the tools that they use tend to exploit them quite a bit by taking heavy percentages. So the hypotheses or the question that I was asking when I began to build this was, how can we do this so that we level the playing field, we remove the hefty commissions, but we still create a profitable business that serves the society. And so removing the commission and creating a banking services or financial services application around it removes the need to charge people 20% of their income.

And you can make money through the payment gateway so that it’s not a pay to play model. With Upwork, for example, you pay to play, literally you pay a monthly subscription to buy connects in order to generate leads to find people that will hire you. And then, so after you’ve paid, you get your client, but then Upwork also takes a 20% of your income from that. And then they take money when you deposit that money into your bank account. So they’re taking it three ways. And then they’re charging their client that hired you a processing fee when they pay you by debit or credit card. And so the freelancer is getting hit from all directions and they still haven’t paid their taxes yet.

The issue is by the end of the year, what money is left after you’ve had your expenses, after you’ve done your legion, after you’ve taken that 20% commission and you’ve done the work, what really is left for the independent worker? And so the model that we built is completely the opposite of that. It’s like, let’s give. Let’s give to this mass market. And it’s projected that over half the global workforce will be freelance by 2027. Already right now, 52 percent of people in at least the United States and the United Kingdom are doing side hustles. So they’ve got a day job, but they’re doing a side hustle working to make ends meet. And yet we felt like we just need to make it fair again and change the change the way we work.

Ok, well, that sounds and we’ll get into it a little bit deeper. But before we go there, I’d like to talk about your framework that we discussed on the prequel that you have developed in your with your expertise as building a startup company. And I think you called it the jobs to be done interviewing process. So how do you figure it out? What is a good offering for customers when you started your start-up?

So a big part of that and this is a framework that already exists. So it just happens to be one that we used that works very well when you’re interviewing customers about the types of products they use, the products they need, what are the most important products or services that they’re using or needing and getting a real feel for, you know, what, why they make decisions about the products that they use. So typically what you do is you have a good idea when you start a company, who you want, who you believe your most valuable product, you know, client will be, and who may be those first movers who will adopt your product, you know, in the early stages.

And so you want to really get in with them and chat to them and talk about what they use and how they’re solving a job, how they’re getting a job done, and what tools or what have they pieced together to get the job done. And so you walk them through a process, you ask them questions, and you usually start with, well, what products do you use right now for your business? So in my case, we talked to freelancers and self-employed people and we say, “Hey, what kind of tool do you use when you talk to a client? Do you pick up the phone? Are you using video or audio calls? How important is that to your process? How much do you use your calendar? How do you organize your time? How are you organizing your finances? And do you have an invoicing system,” for example.

And we gather that information and generally across the board, there’ll be five, six, seven to 10 pieces of software that are repeat types of software. And when you talk to them and say, “Well, how do you use that software?”So if they say “I use WhatsApp to talk to my clients,” so how are you using that? Is it the first time you talk to them? Is it after you’ve already onboarded them? And what are you using that for? If you’re using Slack, if you’re using… And so you get an idea of why they use a piece of software, what made them change from the software they were using beforehand, if they were using any, and what provoked their decision to move if they’ve changed banks, they’ve changed whatever that is.

And it generally takes around a half hour per client that you begin to get a really, really vivid picture of who are the people that you are going to target and who aren’t and how we could improve their experience. to or is improving that experience is we’ve built in those tools that most self-employed people use into one seamless platform. And so that they aren’t paying for multiple pieces of software and they’re also not wasting so much time logging in, logging out, getting OTPs, filling in this, right?

So basically the process is all about figuring out the gaps that those people are experiencing in as they are using whatever software or whatever application or product they are using and then seeing how you can fill that gap in a profitable way.

Exactly. And ultimately you want to make it better, more seamless, save time, save money, save energy. If, you know, otherwise, what problem are you solving? Because if there’s already an existing possibility that they can smash something together themselves, why would they pay or why would they join something like, you know,

Why would they bother learning a new system? 


So I read somewhere that you have to be 10x better than an existing solution for people to make the switch. Is this true?

I don’t know. I don’t know that there’s there’s enough data or scientific support for that. But I think it’s something that people say and it’s certainly something to strive for. It really depends on how, how well you know your customer, how much better you need to be and also kind of I think there’s a little more to it. I think there’s brand building and, you know, if you look back over the last decade of brands and you think Coke versus Pepsi, you know, you drink Pepsi when, when there isn’t Coke around. Right. So it’s, it’s a, I think it’s an admirable goal to one of 10X better than than the competitor, but I don’t know if it’s realistic or not.

Because a lot of us, especially in the world of apps, we switch between multiple platforms on any given day and don’t even think about it. And it’s not necessarily that we’re leaving one app just because one’s better or one’s not. It’s just, we’re using them in specific ways based on our use case or our habits, you know? And the market is full of all kinds of great technology. I think in any given day, I might use 20 apps. I don’t know about yourself. 

Yeah, for sure. 

So you really have to think about, Is this a matter of me switching? If I turn on Netflix and I go, “Ugh, I’ll go watch the BBC, am I trading off? Am I switching? in my trading off, in my switching. They’re both in the same place.” You know? 

Still watching television. So it’s just a different channel.


So let me ask you about Wedo. So how do you scale Wedo? Are there network effects that you can leverage when scaling Wedo? 

Yes, so we’ve built in quite a few network effects in terms of in the technology itself and then of course partnerships with other networks that are compatible. We have built quite a pipeline of partnerships to exploit that. And yeah, definitely. So part of our network effect built into the app is invoicing. For example, when you send an invoice to someone, it says join Wedo and from that network effect of just simply doing that, taking that action of wanting to get paid, you’re onboarding a new potential customer that you can reach out to. Same way with chat applications. When you think of Telegram, WhatsApp, any chat application, in order to chat with someone, you kind of need to invite them from your network so you can actually interact with that person. Zoom is very similar. So there’s inherent network effects built into our application. And those aren’t the only ones, but that kind of invite system that allows you to communicate within a social network is implicit to social networking, in any case.


And so that’s a really important piece. Obviously, traditional marketing, paid marketing, PR, the rest of it. And aside from the multipliers of partnering with various networks are all part of our go to market strategy and things that we’re actively working on the scale. 

Now, I’m really curious about you mentioned that. You know, the millennials and the Gen Z’s, they no longer want to work for the man or for the woman, if I want to be politically correct. They want to be work from wherever they want, whenever they want. So tell me a little bit about this concept of the digital nomad, being a digital nomad. And, you know, I mean, you’re in Spain, right? Right now, and you actually work, live in London, or I think your LinkedIn profile is in London. So you are kind of being a very mobile person. So what are the pros and cons of being a digital nomad?

Well, I think one of the big pieces when someone does leave a job, whether it’s forced upon them, or it’s part of the great resignation, or leaving any company, is that fixed nine to five or that fixed situation where you have to go to an office can be cumbersome. And humans don’t necessarily work best just because they’re in an office and they’re being stared down by their boss or by their peers or whoever that is. So the concept of digital nomad is just being able to live anywhere you want, maybe go live in Asia for a month and still be able to do your work And we live in a day and age when it’s not necessary to be in an office in order to be highly productive and I think when you have tools that hold that help the help leaders hold people accountable for their work. Because primarily the objective especially in technology companies, is that you move forward and that you reach your OKRs or the KPIs or whatever your goal was for that day, that week, that year, that month, quarter, whatever.

And so the concept of digital nomad is really to be able to find places and spaces where you feel happy in your work that allow you to be more productive and the flexibility to get the work done without clocking in or punching a time card. And that’s really all that is. And what we’ve seen is, of course, post-COVID, with all the layoffs of companies, people have had plenty of time to sit back and think about their lives and think about what they’re doing in the majority of the time you spend in your life as an adult until retirement is work. And so people are, the younger generations especially, but you see it in Gen X as well, are taking that opportunity to go explore and find their passion. And then the freelance and gig economy and self-employment is one avenue for that. As more and more companies lay off employees, they’re hiring consultants and freelance workers to replace those employees and those gap, those skill gaps. I think it’s also very interesting because it would allow you to become more expertise if you wanted to, and be able to work fractionally across many companies without being locked into one particular roadmap for your career.

So let me share with you my recent experience with with a couple of digital nomads and maybe that’s an age thing. I’m 55 years old. So maybe I’m looking at these things differently, but I definitely I had a weird experience. So I was looking for this this digital someone to help with my website. And I saw that the guy had a company in London and looked like a nice website, looked credible, and he showed the team and everything. And then I scheduled that call with that person. And he took the call from a hotel room and I asked him, where are you? He said, I’m in Thailand. So I immediately thought that, OK, this guy is in Bangkok. So how much of his attention am I really going to get? He’s got so much distractions there.

He may just delegate my job to someone and he’s not gonna be that into it. That was my impression. Maybe it was wrong. Now here’s another call. Then I scheduled a call with someone who was supposedly in Vienna. So, “Okay, that’s good.” And then I caught the person. Turned out she was in in Bali and there was some bamboos behind her. And and to create your we had a chat. She said she could help me. And then I ever heard from her. Now, five years, five days later, she sent me an email. Oh, I got a food poisoning. Sorry, I mean, these digital nomads, are they not being distracted from from working? I mean, if they were in Virginia here, maybe they went into an office that would have given them a structure and it would have removed some of the distractions. And they could have actually focused more on getting the job done. But again, so maybe I’m being biased here, but isn’t there some cause to being a nomad as well?

I think, well, from my point of view, it’s all going to boil down to the individual and their own willingness to perform well and the pride that they have in their own work. So you can take someone who’s a very diligent worker and put them just about anywhere and they’re not likely to get distracted. Having said that, we’re also dealing with a generation who are constantly distracted. ADHD is like not an acronym. That’s like so like part of the like social, you know, awareness at the moment, everybody’s got it somehow. And so, you know, you’re just as likely to be distracted if you’re in your home or in an office, you know, there’s television, there’s cars outside, everyone’s got this extension to their arm, you know, of a mobile phone.

And so it really is more of an individual thing. And that’s true, whether it’s an employee, a digital nomad, a freelance worker, self-employed, anyone can be easily distracted. And the idea of being able to take your work and go other places with your work isn’t new. We’ve been doing it the last couple of decades, it’s certainly in technology. For me, if I know I’m going to be somewhere a couple, a couple weeks, I’m more likely to set up like a desk in a hotel room, work, and then I’ll plan my time so that weekend or evening or maybe I work from 12 to 8 in the morning as I’m doing something else and I’ll create my routine and it won’t change my output because you dedicate most self-employed consultants or freelancers with employees, they’ll just, you know, oftentimes you’ll have the period of work and then you’ll notice a slump after lunchtime or whatever.

You’re just as well sending your employee home or off to, you know, off on a walk and say, “Hey, come back at 4 p.m. when you’re awake again,” right? And so we’re humans and we all have a biological clock and we all have habits and we all have like a propensity or an ability to to keep focused for a period of time. And I think flexibility in the workforce makes sense because you know when you best perform and there’s a lot of variances depending on when you sleep, when you wake up, how you eat, whatever. And so I don’t see the argument of distraction being an issue. I think that it’s just the way if you get used to being a digital nomad and every month you’re in a new place, you form those habits if you want to be able to make money, please your clients and get, you know, and grow your business, right? So you may get a slacker or two, but that’s true of everywhere.

That’s just maybe it’s just a reason to bias. So before we wrap up, I have another question, which just came to me as we were talking here. So one of the things that I think is challenging if I go on Upwork or Fiverr, one of the challenging aspects is that how do I find someone that I think would be a good person for me? I can read the reviews, but they are biased to some degree. It also depends on the person, how diligently they are reading out the bad reviews or how they hustle for the good reviews. So it’s hard to know. However, when you’re a social network like LinkedIn, you see what the people, what those people posting, you see a little bit about their lives, about their personality, their character. So I wonder whether Wedo helps with that by being a social network, whether this aspect is more prevalent can actually see the individuals behind the nomads.

Yeah, I think, you know, social media does reveal and help you identify characteristics, opinions, the way someone handles themselves, et cetera. And I think that is a really important piece. The second piece with Wedo is that we do KYC and KYB on everyone who joins the platform because it’s inherent to being a Fed tech. So, you know, if we’re going to issue you a debit card in a bank account, then we need to know that you’re really Joe Smith, right, or you’re really Steve Freda, right? 

Know your client. Can you guys say know your client?

Yeah, know your client, know your business. And so both of those aspects generate a lot more diligence for you in any case. And then, of course, inherent in the social network and social media, it means that you can go and explore who that person is on other platforms. And there’s no reason not to, because we’re not trying to take 20% of that freelancer’s income. On Upwork, you don’t even get a last name of the person until after you’ve engaged with them. And so therefore you don’t have as much scope to do any diligence and it becomes time consuming and cumbersome.

So yeah, I think that that is one of the main reasons why we added this social media aspect to the app. But not only that, it’s to improve communication, improve collaboration and community amongst the freelance economy and business. And that’s really important too, because when you work in a solo preneur, or, you know, if your work is a self-employed person, you’re isolated, you’re working by yourself, and you have a tendency to feel like the FOMO, maybe not be, you know, every day you’re not turning up to a whole bunch of people who are working within your industry because you’re working solo, and creating community around topics and community around verticals is also something that’s missing in the market.

And just putting that all together so that there’s an end-to-end seamless way that is social, that gives you a sense of community, although you may be a unique solopreneur or consultant, I think is important because community is something we all need. And we all saw that through COVID when we could only go out for an hour a day and walk our dog, how important community is.

So that’s great. So if someone would like to learn more, either they are a solopreneur and they want to be part of this community or they want to explore or someone like me who would maybe want to hire someone on the network. So how do we get to, you know, get to find things out, what’s the most effective and efficient way of connecting with Wedo and also with you.

Yeah, well, go check out Wedo.ai. That’s the website, W-E-D-O.ai. But you can download the app on iOS and Android. We just launched. We’ve got around 2,500 people on the app. It is the type of application you need to invite people at the moment, you know, in order to interact with people. But we’re really encouraging all the early adopters to come on and break it And, you know, so so that’s how 

Fantastic. So Indiana, Greg, the CEO of  Wedo, it’s a new type of freelance social network. I’m very curious. I’m going to log on and see if I can find a good web designer there right now. So, Indiana, you’re also on LinkedIn, Indiana Gregg. You can check her out on LinkedIn as well. Thank you very much. A very exciting venture. I wish you luck. And thanks for sharing your perspective on this whole area of new world of work with us.

Thanks for having me, Steve.


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