How To Design A Sustainable Freelance/Contracting Career

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Ready to kickstart your freelance career or just getting started on your freelance journey? You’re in the right spot. Learn the tricks of the trade from the industry’s most experienced freelancers.


The independent talent movement is the future of work. If you’re considering leaving full-time employment for a career as a freelancer, now is the time to find your successful space in the independent talent workforce. More people are working freelance today than ever before, with the freelance marketplace now contributing $1.2 trillion to the US economy. Some of the most in-demand roles for freelancers right now are senior developers with professional experience in React, Python, Blockchain, QA, and Node.js.


This workshop will help you design a sustainable and profitable full-time (or part-time) freelancing/contracting career. We will give you tools, tips, best practices, and help you avoid common pitfalls.

39 min
15 Feb, 2022

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Video Summary and Transcription

Freelancing has become a popular career path, offering stability, flexibility, and economic opportunity. Major corporations are increasing their use of freelancers, and freelancers enjoy the ability to work on their passions and hobbies. Negotiating contracts and analyzing market rates are important for freelancers to get paid appropriately. Building a strong brand and online presence is crucial for freelancers to attract clients. Platforms like TopTel offer exclusive networks, support, and vetted clients for freelancers.

Available in Español

1. Introduction to Freelancing

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Today I want to talk to you about freelancing and how you can design a freelance career. Freelancing has had a negative connotation, but there has been a massive shift over the last two years. We'll discuss why freelancing is popular, how you get paid, build your brand and business, and find work. There is a huge amount of economic opportunity in freelancing, with stability, flexibility, and support. Many freelancers enjoy taking on work from US companies and being paid in US dollars.

As I said, my name is Shane. I work at TopTel. And what I want to talk to you guys about today is freelancing. And specifically, I want to walk you through how you can design a freelance career. And I want to and I want to say that there's one word there that I think is important. And that's the word career.

Freelancing or contracting as it's called, has had a negative connotation. And it's no longer that way. And I think of course, over the last two years, we've seen a massive shift. And so I'm going to start out with some statistics for everybody. I think you guys might find these fascinating. So let me. There's the agenda. This is what we're going to be going over. We're going to talk about why freelancing, and I'm going to share some current statistics. We're going to talk about how you get paid, how you build your brand and business, and how you actually find work. And then you see the speed coding challenge there.

Here we are. If anybody has heard of freelancing or contracting, you know that it's become popular, but you also know that it's very, very risky, because it's far easier and more convenient and in some cases more accepted to have a traditional job, where you work for an employer and you get a steady pay. And when you talk about freelancing or contracting, I think one of the things that a lot of people naturally are fearful of is, well what happens if I don't have steady pay? How do I pay my bills and feed my family, etc. But we're going to go over that today, because I think what you're going to see is going to change that opinion a little bit and ease that fear. One of the things I want to point out on this little chart, and this is from Statista, they're a great, great site, they do a lot of fantastic stats. So one of the things I want to point out here is since 2017, you can see the increase. The big increase happened over the last couple of years, obviously, and there is a huge amount of economic opportunity in freelancing. It's become way more stable. It's highly flexible in terms of your lifestyle. It actually allows you for career growth and there's a huge growing community of support around this and I'll show you what that means in a second. I think you'll really like these statistics. Economic opportunity, what does that mean for you? A lot of the times, when you take on freelancing work from another country, it can often be with a US company and they will pay you in US dollars. In many cases we have found that freelancers enjoy that.

2. The Rise of Freelancing

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Freelancers have earned over a trillion dollars in 2018, and about 36% of freelancers now make more than $75,000 a year. Freelancing has become so stable and accepted that it has become a career path. Major corporations such as Airbnb, pharmaceutical, and healthcare companies plan on increasing their use of flexible workers. Microsoft, Apple, and 30% of Fortune 500 companies also use freelancers extensively. Freelancers enjoy the flexibility to work on their passions and hobbies, adjusting their hours and location as they see fit.

They get paid a lot more and for them it's really a good thing. If we're talking about not even global, but just in the US, freelancers have earned over a trillion dollars in 2018. That is a lot of momentum. About 36% of freelancers now make more than $75,000 a year. Again, this is US dollars, sorry. And what's very interesting is when they go out and they talk to freelancers and they talk to contractors, they ask them, what would make you go back to a traditional job? And 50% of them say no amount of money would make them go back. And you have to ask yourself, why is that? What are they trading for that? And what you'll see is that freelancing has become so stable and accepted that they are able to make an actual career out of this, a career path. And again, I'll show you some of those examples here in a second.

So how is this becoming accepted? And by the way, I want to point out in all of these images, these are actual top towel. These are freelancers that you're seeing. These are not fake, fake images. These are our shots of freelancers, 80% of major corporations. And when I say major corporations, I mean big companies such as Airbnb, pharmaceutical, healthcare. They plan on increasing their use of flexible workers in the coming years. They're having such good success with hiring from a pool of talent that they're going to continue and increase that. 30% of Fortune 500 companies, and these are a lot of big names you've heard of, a massive ton of big names, Microsoft, Apple, all of them use freelancers. They may not advertise that, but they do. 92% of freelancers expect opportunities to increase in the coming years. 33% of companies use freelancers extensively, so this is no longer a thing that is unstable or negative.

Flexibility, I think when people think of freelance work, this is the first thing that comes to mind. They think, oh, I could be in a cafe on my laptop. That's true, that is true, but I think one of the things we find with our freelancers that they continually come back and tell us is that it really changed their life because if you imagine it, think about this. Let's say that you have a passion, a hobby, something you want to do. When you're freelancing, you get more flexibility. You can adjust your hours as you see fit, and you can work wherever you see fit. So we have a lot of ... we actually have a lot of stories of our own freelancers who have passions. They own nonprofits. They go to other countries and teach kids how to code. They are into things like skydiving.

3. Freelancer Career Growth and Community

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Freelancers have the ability to adjust their hours and pursue their passions outside of work. There are inspiring stories of freelancers going beyond their work. Career growth is possible in freelancing, but it depends on where you freelance. There is a growing community of freelancers, and you're not alone. The platform you choose and how you choose to freelance are important factors.

And because of the ability to kind of adjust their hours how they want, they've been able to pursue these passions outside of their work. And again, coming back to flexibility, that really has changed a lot of their lives. We're doing a lot of interviews right now at TopTel interviewing freelancers, the freelancers in our network. And we're going to be posting those online, their stories. And there's some really inspiring stories that even really surprised me of things they've been able to go out and do beyond just the work.

So career growth. I think a lot of people naturally are afraid, they think to themselves, well, if I'm at a company, and I'm a developer, I could become a senior developer. And then I could become a manager and then I could become an executive baby, or something like that. The reality is, when you're freelancing, you can also do those things. The key is where you freelance at. Because if you're just freelancing completely on your own, it will obviously be a little harder to have that career path.

Okay. Thanks, Alex. I will. Yeah. I got your question. I'll answer that. Coming up. It's coming up quickly. So anyway, career growth is possible. You can actually have a career path. Okay. And lastly, I just want to mention everybody, there is a growing community out there. You're not alone. It's not like you go freelance and you're solo and you're just by yourself in an isolated bubble. Again, this really depends on the platform you choose and how you choose to do your freelancing. That is exactly what I'm going to talk to you about next. I am going to answer your question, Alex. Don't worry, I will.

4. Getting Paid as a Freelancer

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Negotiating contracts will become a very important part of your career as a freelancer. Look at your years of experience to determine your worth. As you gain more experience, you can command higher rates and negotiate your contracts accordingly.

Don't worry, I will. Getting paid. A lot of people wonder about this. How do they get paid? What are they worth? How do you go from being an employee of a company who has set your rate of pay to doing this on your own? How do you know what you're worth? That's an interesting question. So here's the answers. Negotiating contracts will become a very important part of your career as a freelancer. You got to look at your years of experience first and foremost. When you reach the point of having two, three, even four, five upper in those years of experience and plus, you're able to command obviously higher rates. And you can negotiate your contracts based on that.

5. Analyzing the Market and Pricing

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When freelancing, it's important to analyze the market and understand the pay rates. Companies typically pay freelancers 20 to 30% more than regular employees to account for expenses. The 80% rule states that if you're getting more than 80% of the jobs you apply for, you're priced too low. Calculate the minimum amount you need to live comfortably and build from there. Always put some money away for unexpected situations or to take time off.

One of the things is that we try to instill in people is analyzing the market. It's really easy to do. Actually, you can go out and look at what the pay rates are. Now, interestingly enough, if you go look at what companies are paying, let's say a senior React developer. When you're freelancing, you have to understand you raise that rate by about 20 to 30%. Because you have to account for your own expenses. So that's really important to know.

We have something called the 80% rule. And it's really simple. If you get more than 80% of the jobs you apply for, you're priced too low. You need a bunch of clients to reject you. I know that sounds crazy. I know that actually sounds odd to say. But if you're getting too much work, you're not pricing yourself of value. And you might think, yes, but I need all this work. Actually, no, you just need good work. And good work can mean less. So it's a strange rule. But it actually works.

Here's a tip, best practice tip. Calculate the minimum amount of money you need monthly and yearly to live comfortably. What is the minimum? What is your base? I can pay all these things, all my bills, all my everything, have some savings. Because your income will likely fluctuate based on your projects. You want to just calculate that minimum amount and then build from there. Start from there, work backwards, if you will. Always put some away. Not because you may not get work, but because you may want to take a month or two off. Some people do that, believe it or not, they do. They may do that to increase, to learn a new skill. They might, you know, for various reasons.

6. Getting Paid and Building Your Brand

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Getting paid is obviously one of the most important parts of freelancing. At Top Towel, we have a pay rate calculator that takes into account factors like your experience and expertise. It provides a mid-range, upper-range, and lower-range rate, as well as an estimate of the amount of work you can expect. Building your brand is also crucial as a freelancer. Representing yourself and creating a strong brand can lead to continuing work and valuable referrals. Every interaction with a client is an opportunity to further your relationship and have them market for you.

Getting paid is obviously one of the most important parts of this and there's many ways to actually do it. At Top Towel, we have put together a calculator for freelancers. When they join the network, we have a pay rate calculator that takes all of this into account. So let's say you are a JavaScript expert and you have five years of experience and you want to know what your rate should be on the platform, what are you going to put your rate at. You can plug in the factors and then it will show you the mid-range, upper-range, and lower-range. And then it will also tell you how much work you can expect to get.

Okay. I had a little internet blip, but I'm back. Okay. Okay. All right. So next, I'm going to talk about building your brand. Not a lot of people think about this. This can be something that you may not even have ever thought of. You may not have encountered before, but think about how important it is. It's beyond your resume. It's you as a person. You're representing yourself, and you've got to build that brand, and I have some great tips to that and why. Because everybody has to build their portfolio and their brand as they go along, and it's really important, and I'll tell you why it's important. It's important to get continuing work. As a freelancer, you represent you, and when you do that, it's important to remember that every interaction you have with a client is key to furthering that relationship but also letting the client talk about you and market for you, and they will. Most of the clients you work with will know other people. They'll know other companies. They'll have colleagues. The best thing you can ever have is a referral. It's the best thing you can get in many cases, not all cases. Think about your brand. Think about who you are as a freelancer and what you want to put out there into the world. You may be frustrated with a client. You may be frustrated with the work. You might even be frustrated with some aspect of what you're having to do or this project is going.

7. Building Your Brand as a Freelancer

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When building your brand as a freelancer, it's crucial to consider every interaction you have beyond your resume. Clients often do their homework and research potential freelancers on platforms like LinkedIn and Twitter. Your brand encompasses all these aspects, so it's important to build a strong online presence.

It's really important and again, it does go beyond the resume. Think about this too. If a client is going to hire you for a project, think about while you're working as a freelancer and you're doing your work. Think about far beyond your resume and think about every interaction you have anywhere. Because if somebody is going to hire you for a really big project, they're going to do their homework as well. And they may look on LinkedIn, they may look on, you know, Twitter or wherever. And they want to learn about you. And all of those things are your brand. So think about that as you're building your brand. It's not just about your resume. Very important point to make.

8. Starting a Freelance Business

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We discussed the increasing popularity of freelancing and touched on getting paid, setting rates, building personal brands, and the different terms used for freelancing. Freelancing involves starting a business, but it's not as scary as it sounds. In most countries, freelancers are considered sole proprietors. To begin, you should register your business, which can usually be done online. After registering, it's important to obtain a business license from your city to ensure there are no legal issues in the future.

We talked a little bit about freelancing. I showed you some stats. I think if you haven't gotten the hint by yet, it's increasing. And for many, many, many, many reasons.

So we talked a little bit about getting paid, how to set your rate. Also building your personal brand, and a little bit about why people freelance. And when I say freelance, just for anybody that's new, I'm talking about contracting, freelancing. There are different terms used for different legal reasons.

When you freelance, you're starting a business. That might scare a lot of people. Some of you probably already have a business. It's not a scary thing. You're just a sole proprietor. That's really what it is. And again, this is different in every single country, and I realize that. And so it's not an all-encompassing thing. But for the most part, you are starting a business. Whatever country you're in, you are a sole proprietor.

And what does that mean? Well, there are certain steps you wanna take. And the first step is you wanna register your business. Now, again, I 100% understand that in every country, that's different how you do it. In the U.S., you do it in the state you live in. So for Colorado here, I went to the Colorado government website and I registered a business. It really doesn't cost that much money. And you register it in your name. You will, most of the time, you can do this online these days. It's really pretty fast. Once you register your business, you then wanna get a business license. Again, all this is, is just setting yourself up so there's no legal issues or challenges in the future. A business license is usually done with the city you live in and so you wanna make sure you have that.

9. Tax and Health Insurance

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Once you have your business registered and a license, find a good accountant or another freelancer who is an accountant to help with taxes. Set aside the amount equivalent to your tax rate in a savings account. Expenses like work meals, travel, and home office can help reduce tax liability. Outside the US, health insurance is often provided, but for those concerned, options like healthcare.gov, COBRA, spouse's policy, parents' policy (if under 26), domestic partner's policy, and private health insurance are available.

Now, once you have your business registered and you have a business license, I put the third bullet point here because this is really, really important. Most people do not have the time or the interest in figuring out the whole issue of taxes. It's a sticky issue because there's so many different ways to do it. Suffice it to say, find a good accountant, somebody. Find another freelancer that's an accountant. Support your local freelancers. If you wanna do this on your own, it's totally okay. Here's the rule. Whatever your tax rate is in your country, your location, just take that amount out and set it aside in a savings account. Again, you're gonna be charging more money when you're working on your own, so you can take that amount and set it aside, then deal with taxes at the end of the year whenever your location does taxes.

So another tip. Here's a tip. Anything you do as a freelancer, work meals, work travel, if you have any, your home office, all of these things you do are things that in most cases, again, I'm talking about more of a US-centric here, you can use to reduce your tax liability. So there's a lot of advantages to this as well. So it's not all bad.

Okay, that said, I'm gonna just very, very, very briefly cover this because I understand that this is more of a US issue than anything else. Once you get outside of the US, most people have health insurance provided for them. I will say, however, having been to many conferences and events, this is a number one question on top of a lot of people's minds. How do I deal with this because my company dealt with it? So I'm gonna mention these briefly for the folks that this might be an issue for. There are options. In the United States, we have healthcare.gov, and again, this is state by state. You can buy your own healthcare insurance. Your freelance rate that you set will help you cover some of this. We also have COBRA. Many people have heard of that. A lot of freelancers go on their spouse's policy or in some cases, if you're younger than 26, your parents' policy. Domestic partners, many insurance allows for you to be on their insurance. There is also, believe it or not, private health insurance. Yes, it's a little more expensive. I totally realize it.

10. Health Insurance Options for Freelancers

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As a freelancer, you have the flexibility to purchase and customize health insurance plans. Freelancers Union offers a group plan for freelancers, providing a group discount in certain states. Don't let health insurance be a major barrier; there are many options available.

But as a freelancer, as a business, you can purchase these plans and adjust them however you see fit. And lastly, there's group coverage. Freelancers Union has been working on, for many, I think it's been for several years, a group plan for freelancers. So, what they do is you join the group plan with the Freelancers Union, they call it, and in certain states this applies and you can get a group discount on health insurance. So, the main takeaway is that if health insurance is something that is on your mind as a worry, just understand that there are many avenues you can take. Don't let that be a major barrier.

11. Finding Work as a Freelancer

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Finding work as a freelancer can be daunting, but there are tips to help you. Continually source clients and utilize your first anchor client for referrals. Over-deliver during engagements to build your professional reputation. Job boards like Indeed are fair game, and freelancers have had success reaching out to companies directly. Freelance talent platforms are also worth exploring.

Okay. Big topic, probably something that a lot of people wonder about, finding work. This one is huge because this is probably the most daunting thing about going on your own. How do I find work? And not only that, let me just say this. How do I find steady work so that I'm not struggling?

So okay. Couple of tips. Continually source clients. What do I mean by that? What I mean by that is, going back to building your brand that we talked about earlier. When you're working for a client and you've got your first freelancing job, and by the way, you know, I'm talking to developers here on this call and some designers, I realize. I'll shout out to the designers as well. Because of the increase in demand and freelance work, getting your first client won't be as hard as it was five years ago. That first anchor client is important. You can utilize them to give you referrals, and don't be afraid to ask. Don't be shy to ask them for referrals. As well as they will talk about you to their colleagues. I guess that is a referral. And what you wanna focus on during this engagement is really over-delivering. I can say this also from personal experience of doing website work. When you over-deliver, they will go the extra mile for you. It's really amazing how much they will value you and talk about you and get you more work. It will come. And that's part of your professional reputation if you will.

There's also job boards. Job boards are fair game. Let's say Indeed. You go on Indeed and you see a company looking for developers well. A lot of freelancers have gotten creative with reaching out to those companies and saying, I know you're hiring for developers, I'm a freelancer, I can help. And in many cases, they will be willing to talk to you. That's, again, people have done this. Freelance talent platforms.

12. Choosing the Right Platform

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Choose your platform wisely, do your research. It's very tempting to jump onto one of these platforms and you can quickly get dismayed with freelancing if you don't do your homework and understand the audience on these platforms. Some people have had a lot of success and they're creating a really fantastic profile on Upwork and you know, they get work. Some haven't and I think that it all comes down to how you really want to take your career. So again, do your research.

Okay, let's talk about that. We all know the big names out there, Upwork, Fiverr, Guru, Freelancer.com, hmm, there's several. There's several. And then there's TopTel. I'm gonna save TopTel for last because obviously that's what I know the best. I will say this, choose your platform wisely, do your research. It's very tempting to jump onto one of these platforms and you can quickly get dismayed with freelancing if you don't do your homework and understand the audience on these platforms. Some people have had a lot of success and they're creating a really fantastic profile on Upwork and you know, they get work. Some haven't and I think that it all comes down to how you really want to take your career. So again, do your research. These platforms are there but realize they, a lot of them are, you know, I guess this is feedback I've heard from people. They get in there and everybody's like, you know, competing with rates and that's never fun to do because you don't want to undervalue yourself just to get work. You know, and so, yeah, just, I would do my homework is what I would really do. And don't forget to investigate Top Tal.

13. TopTel: Exclusive Network and Support

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TopTel is different from other platforms like Upwork and Fiverr. We have a stringent process to join our exclusive network, including an online test, technical interview, and project. You'll work with fellow developers who are experienced freelancers. You can set your own hours and rate of pay. TopTel provides support, payment, and a large community. Our matchers send you work based on your skills and client demands. You can join teams of freelancers for certain projects.

And speaking of that, I'll tell you why. And this will answer your question, hopefully Andrew. Okay, so all of these people in this photo, by the way are freelancers working in our network. They got together, they had a meetup recently. I think this was about the end of 2021, I believe.

Why is TopTel any different? What makes it different than Upwork or Fiverr or Freelancer or any of those others and what do they do for you? So why, why are you going to take the time? Well, TopTel takes care of a lot of the things that I talked about earlier. Number one, you may have heard this. We have a very stringent process to get through the TopTel into the network. I can tell you a little bit about that process actually. And we do look for people with greater than two years of professional paid experience. There is an online test. There is also a technical interview and there is also a project.

Now, in many cases, you're working with a fellow developer through this process who works at TopTel, who used to be a freelancer and, in many cases, still is. They just are doing two things at once. We see a lot of people come in and they are already working full-time and they come in and they set their hours at 10 hours a week. They set the rate of pay and they just want to try it out and that's perfectly fine. The difference, the main difference with TopTel is you join an exclusive network that is not a race to the bottom. You are paid by TopTel. You are supported in your career path and you have a massive community behind you. Also, we have matchers that send you work.

So how that looks in real life? You will, we have a platform and it's obviously it's mobile like most other platforms. And you have a profile. We also have profile editors that help you create a really good profile. We have a whole team dedicated to that. And then we have matchers. Our matchers look at your skill sets, they look at your work and they look at what current clients are demanding, and they will match you. And they will send you the work and you can look it over. And if you're interested in the role you will go ahead and put your name in to be a part of the team. In some cases, clients hire teams of freelancers. So you're not alone.

14. Benefits of Joining TopTel

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You could be on a team with other freelancers and in many cases, a lot of our freelancers prefer it. We also have a huge community. We take care of the administrative overhead so you don't have to deal with all the taxes. We vet the clients as well. We have really good companies that you'll be able to work with. We have a whole list of companies on our website. We want to share a video that sums up the freelancing experience.

You could be on a team with other freelancers and in many cases, a lot of our freelancers prefer it. They have made really lasting partnerships and friendships. We also have a huge community. Our freelancers are all in different various Slack channels together. We have a whole team that works for TopTel that sets up mixers, meetups. We have community leaders. Some of our freelancers are leaders in the countries and cities that they live in. And we support doing all of these things. I mean, we put ourselves behind this.

So we also take care of a lot of the administrative overhead so you don't have to deal with all the taxes and all that. We take care of that because you are paid by TopTel, not the opposite. So I think those reasons alone. The other thing is too, to note, we vet the clients as well. So you're not gonna be in the situation where you're trying to chase a client for pay because TopTel's paying you. We will chase the clients, but we don't really have to do that. We have really good companies that you'll be able to work with. I mean, I can say a few of them, Airbnb, large pharmaceutical chains. We have a whole list. It's on our website. You can see the list of companies that we work with. And really good projects that allow you to up-skill and stay engaged.

So very last, I want to share this little video with you share this little video with you that we produced. These are real freelancers. We had them agree to shoot this video. It's short. It's like a commercial. And I wanted to share it with you guys because it's a really good video that sums up very well the freelancing experience. And what I'm gonna do here is play it. But I also want to make sure, I wanna make sure that this is coming through my sound at the same time. So I think in some cases that does not happen.

15. Sharing a Video with Actual Freelancers

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I'll post the video in the chat for you to watch. It's a good video featuring actual freelancers.

And so I just wanna make sure that everybody can hear this. I may have to actually take my... Well, what I'll do here. I don't think you guys will be able to hear this. So here's what I'm gonna do. I'm gonna just post this into the chat. And you can watch it, because I know it'll be a disaster if I try it because I'm using two monitors, et cetera. And so if I don't, I'm gonna be disappointed if I try it because I'm using two monitors, et cetera, et cetera. We all know how that goes. We've been down that road.

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If you've always wanted to participate in a hackathon to get something up and running in the shortest amount of time - then take an active part in this workshop, and participate in the thought processes of the trainer.
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You can check the slides for Feross' talk here.
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