How we Made Over $100k from Upwork (within our first nine months of business)

If you’re like most people out there thinking about freelancing or starting your own business, you’ve surely thought to yourself, “Having my own business or freelancing sounds great, I just have no idea where I would start.”  

My business partner Tyler and I used to feel the same way… until one day we decided to start moving in the direction of our dreams, started an account on Elance, and serendipitously fell into a business that changed our lives and has generated us over $260K in revenue over the course of just 18 months (No joke – I’ve included a screenshot from our accounting software below).  

There’s a whole lot more that’s gone into making our freelancing business successful than figuring out how to leverage sites like Elance and Upwork to get jobs, but winning bids from online job sites was an essential component to how we got started and it continues to be an extremely important source of work for us.  In the following post, I’ll tell you our story and layout the basic framework that has helped get us to where we are by leveraging sites like Elance and Upwork to win high-paying jobs…

Two years ago, Tyler and I were sitting at a cafe in Medellin, Colombia trying to figure out a way to start a business online and live the life of our dreams.  We had both read the 4-hour Workweek by Tim Ferriss a few years prior and we’d been trying to figure out how to make income online for quite some time.  The idea of living wherever we wanted in the world and making money online sounded amazing.

For the first three months that we were in Medellin, Tyler and I spent every morning taking Noah Kagan’s online course How to Earn $1,000 A Month at a local cafe (the course is awesome, by the way – you should check it out here – not an affiliate link).  During the afternoons, we would exchange business ideas and tirelessly think of ways that we could generate revenue for ourselves online.

Tyler and Tommy in Pergamino
Tyler (left) and me (right) on my birthday during one of our many afternoon work sessions at Pergamino Cafe in Medellin, Colombia. Excuse my haircut, I have since stepped my game up in that department.

When I arrived to Medellin, I was coming off two years of teaching English in South Korea.  Tyler had just spent the previous three months at a program called Exosphere learning how to start an online business in Santiago, Chile.  With our skills combined, the first business that we tried to jump into involved selling an ebook about how to get a job teaching English abroad…

We set up a pre-sales page for the ebook that we intended to create and after a few weeks pushing it out to hundreds of people, something magical happened…

…no one bought it.

We weren’t really excited about the fact that no one bought the ebook, but throughout the process of working on that project – something else occurred…

Click Here to Start your Freelance Journey Today: Learn about the 5 freelancing tasks that even beginners can have success with on Upwork.

While we were working on the ebook, we hired a few contractors off of Elance to do some design work for us.  One day while we were in the cafe, Tyler decided to apply for a couple jobs as a contractor on Elance – just to see if he could get some freelance copywriting work for himself.

48 hours after Tyler applied to his first job on Elance, he was negotiating what would become our first $5,000 contract.  After taking on that initial job, Tyler and I were able to keep up the momentum and make almost $100,000 in revenue in our first 9 months of working on Elance and pull in over $260,000 in sales for our freelancing business (Gingerbread Marketing) over the short time period of a year and a half (I’ve included a couple screenshots from our Quickbooks Online account below showing our exact revenue numbers).

After just a short nine months in business, we were off to a pretty exciting start!
After just a short nine months in business, we were off to a pretty exciting start!


18 months in and we have real business!
18 months in and we have real business!

Before Tyler and I knew it, we had developed a reliable system for ourselves to land high-paying freelance jobs online, consistently.  We started to recognize a pattern to the things that we were doing and eventually it became a process that we perfected and one that we continue to use in order to land sizeable jobs from freelancing sites.  To this day, the minimum bid that we close averages about $3,500 and we’ve even managed to land a few five figure jobs from sites like Elance and Upwork.  See below for a few screenshots of jobs that we’ve won using our process.

NOTE: You’ll see some great reviews from clients we have worked with included below as well.  I’ll talk more in a future post about how to leverage the power of testimonials like these to grow your freelancing business exponentially.

Sample Job Awarded C


Sample Job Awarded D


Sample Job Awarded B


Sample Job Awarded E

As you can see from the awarded jobs above, Tyler and I haven’t had any issues in figuring out how to land big freelancing clients online.  In the post that follows, I am going to lay out the exact steps that we took to win our first $5,000 contract from Elance and make almost $100,000 in just nine months.  This is the same process we used to jumpstart the freelancing business we now run which has grossed over $260,000 in just 18 months.

Click Here to Learn More: How to write killer proposals on Upwork, understand which jobs to apply to, and much more!

The strategies that I’ve taken the time to lay out for you here work for all of the online freelancing platforms out there (Upwork, Elance, Freelancer, Fiverr, etc.) and it doesn’t matter the type of freelance work that you’re doing.  Whether you’re a copywriter, web-developer, graphic designer, etc. – the tactics we’ve laid out apply to your industry and you can use them to leverage your freelancing career on any of the online freelancing platforms.

Alright, let’s dive in…

1.) Figure Out The Right Types Of Jobs To Apply To

It’s no secret; there is a lot of competition out there when applying to jobs online.  As of October, 2015, Upwork had 9 million registered freelancers.  In order to make money from sites like this, it’s impossible to compete on price.  There’s just too many people willing to outbid you.  Online job sites are a loser’s game if you’re not shooting to land high-paying jobs.  Something that Tyler did right away when applying to the first job that he landed us on Elance was go straight for the highest-paying jobs available.  

Without really knowing it at the time, Tyler immediately positioned himself as a premium service provider.   When you land jobs that pay you $3K, $4K, $5K, and $10K, it’s much easier to think of online freelancing sites as a legitimate source of income.  Positioning yourself as a premium service provider starts with finding high-paying jobs to apply to…  

There are a few exceptions to the rule when it comes to figuring out who the highest paying clients on online job sites are, but there are some general guidelines to follow when evaluating whether or not a job posting is worth applying to.   Here’s a breakdown of the same steps that Tyler used to screen the jobs he applied to prior to landing our first $5,000 deal.  These are the general rules of thumb that you should keep in mind when looking for potentially high-paying jobs on freelancing sites.  I’ve included some examples at the end of this section as well with a couple sample screenshots of good and bad jobs to apply to.   

Step 1 – Find jobs from high-paying countries. Where are they from? Step 2 – Evaluate the client’s completed job history. Jobs History Step 3 – Look at how much money the client has spent in the past. Spending History  Step 4 – Review to see whether or not the client has left personal contact details and/ or specific information about their project in the details section. Proposal Details Example of a bad job to apply to: Sample of Bad Job to Apply To Example of a good job to apply to: Example of Good Job to Apply To on Upwork

2.) Make A Good First Impression

When Tyler landed that first job on Elance, there were a few things that set him apart from the competition which allowed him to win a premium client right right out of the gate (as I mentioned, the first contract that we won on Elance was for $5,000.00).  Though we didn’t realize it at the time we won that first job, Tyler had just discovered one of the best ways to help us stand out from the competition when applying to jobs online; making an outstanding first impression.  

Once you’ve figured out the best (highest-paying) jobs to apply to, there are two things that you must do in order to set yourself apart which will result in landing you exponentially more work than the competition.

1.) Create a video proposal.
2.) Put together an EPIC initial written proposal.

Let’s start with the video proposal…

People love when you deliver them a personalized message in a format that is easy to digest.  Video provides you with the perfect opportunity to tell your story in a way that connects emotionally, positions you as an overachiever, and gets the client excited to speak with you. There are a number of different programs that you can use to create video proposals.  Something like Quicktime works great if you have a Mac (Tyler and I use a program called Screenflow which can be purchased for use on Mac or PC).  You can upload the videos to Dropbox or Youtube when you’re finished and include a customized link to them in your written proposal when you submit a bid.

Here are the steps that Tyler and I use to put together the video proposals that lead to landing us those high-dollar deals…

Step 1 – Be likeable and build trust.

People want to work with someone that is likeable and that they can trust.  In your video proposal, it’s important that you make yourself relatable and include specific information from the client’s request for bid.  Talk to the client like a real human being and make sure you are pulling directly from what they have written down in their proposal in your video.  Make sure you mention specific information from their profile (where they are from, etc.) and what they are looking for in working on this project.  You’ll need to make a custom video for every single job that you apply to.

Step 2- Walk the client through what you are going to do to help them.

The next thing you’ll want to do in your video is walk the client through exactly what you plan on doing to help them.  Be careful not to talk just about what it is that you do and make sure that everything you do relates directly back to how you are going to solve the client’s problem.

Step 3- Close with and invitation to talk and direct them to your CTA.

Inside of every written bid proposal you should have a link to your scheduling software which will allow the client to pick a time that you have available for them to speak with you (more on this below).  You’ll want to direct the client to that link and set up a time to speak with them on the phone.  Make sure you don’t say anything about price in the video proposal as that shouldn’t be something that you mention until later.

As you start doing more video proposals, you’ll begin to understand how they work and develop your own flow.  Doing video proposals can feel incredibly uncomfortable for some people at first, but I promise you that it’s worth it.  Tyler and I consider the video proposal to be our secret weapon in landing high-paying jobs.

See below for an example of a winning video proposal that resulted in a $5,995 job.  I included this specific video proposal because quite honestly, it’s not even that good.  But it still landed me a really big job.  The point is, most people out there (even some of you reading this) won’t even take the time to put a video together in the first place when applying for a freelance job online.  Simply making a small effort and creating even a mediocre video proposal can pay big dividends.


If you really want to get good at putting video proposals together then you should probably watch a few more examples.  You can learn how to access four additional sample video proposals that won us a combined total of over $25,000 in work towards the end of our mini-course.  

Typically, we like to keep the videos under four minutes in length although we’ve also had success with longer videos in the past.  Remember that the goal of each video you put together is to create a relationship with the prospect and to get them to set up a time to speak with you.  If you’ve done a good job of creating your video proposal then you’ll get an extremely positive response from prospective clients.  Don’t take my word for it.   Here are a few responses that we’ve gotten from clients in the past after they’ve had a look at the video proposals we sent them…


Client Response to Video A Client Response to Video B   Client Response to Video C   Client Response to Video D
Not bad, huh?  

Before you get responses like this, however you have to make sure that you’ve done a good job in setting up the video with a solid initial written proposal…

After Tyler and I have created a stellar video proposal, we move onto the initial written bid proposal.  Below I’ve outlined and provided an example of exactly how we do this.  This is the same style of initial written bid proposal that Tyler and I still use to land jobs today.  The initial written bid proposals don’t need to be extraordinarily long (though they can be – I’ve included a long form and short form version of the written bid proposal below), regardless of length it’s important that the written bid proposals are effective (and there’s certainly more than one way to create an effective initial written job proposal).  

Note that the examples included here are from Elance, but the same outline can be used on Upwork or whatever other freelancing site that you’re trying to get work on.  As I mentioned before, everything I am providing you with here is universal and these tactics can be applied to jobs you are applying to anywhere online.  If you’re interested in getting your hands on a couple initial written job proposal templates that Tyler and I have put together to help you easily create these on your own, you can find more information towards the end of this post to get access. 

If you’re at the point that you’re ready to start working on the initial written bid proposal then you’ve already picked out the prospective high-paying job that you are going to apply to, you’ve done your research, and you’ve shot the video proposal.

I’ve included some initial written sample proposals from Elance below and they are best to be referenced as something you would include in the “cover letter” section on Upwork or other online job sites.  Take a look so you can get an idea of how we put these proposals together.

Our initial written proposals have three components that help us to distinguish ourselves from the competition: a catchy opening, a link to a video proposal, and a CTA directing the client to set up a phone call with us.

This first initial written proposal sample resulted in a $3,500 job and opened the door to working with a client that has paid us $15,000, to-date. You don’t have to always create a very long initial written bid proposal to get the job.  Here’s another example of a shorter form version of a written proposal that also won us a $3,500 job. Sample Initial Written Bid Proposal
3.) Get On The Phone

Tyler and I learned very quickly that in order to make high dollar deals on freelance websites, you absolutely must get potential clients on the phone – no questions asked.  People want to do business with contractors who are willing to speak with them personally.  It turns out, even if they are hesitant to speak with you at first, clients are much more likely to hire you after you’ve been on the phone with them.

While Tyler and I were busy knocking down our first $100,000 in revenue during those initial nine months, there wasn’t a single deal that we closed without first talking to the client on the phone.  I’ll go into more detail in a future post as to what exactly this call looks like, but the basic guidelines for how this call should flow are as follows:

Step 1 – Build rapport.

Demonstrate to the client that you are likeable and that they can trust you.  When you first get on the phone with a potential client, just relax and be yourself.  Ask them how they are doing and what’s new in their part of the country (world).  The more likeable you are, the more comfortable they will feel.

Step 2 – Ask the client to summarize what it is they are looking for verbally and demonstrate your understanding of their needs.

Up until this point, you’ve been interacting with the client solely through messages online.  You’ve got a pretty good idea what they are looking for but it always helps to hear it again directly from the horse’s mouth.  Quickly mention a couple specific things that you know they are trying to accomplish in working with someone and then have the client restate in their own words exactly what they are trying to accomplish.  Often times when you are talking to the client on the phone you will discover much more about their project than you were able to through their initial job posting.

Step 3 – Ask for minor commitments.

Once the client has mentioned what their goals are in working with a contractor, ask them if you are able to provide them with whatever it is they need, if indeed they would be willing to hire you.  You can state this various times throughout the phone call in order to get them used to saying “YES.”

Step 4 – Make yourself sound exclusive, tell them that you will be in touch soon.

When finishing up the first phone call with a potential client, mention that you are really thankful for their time.  Also say something that makes you sounds exclusive like, “I’d love to see if I can work this project in with all the other ones I have on my plate right now.  You guys seem like a great fit for what I am looking for.”  After you’ve mentioned something like that, simply end the phone call by telling the client you will get them a customized proposal (including price) as soon as possible and that you are “looking forward to working with them.”  NEVER talk about price with a client while you’re on the phone with them.

4.) Close The Deal With A Customized Proposal

Perhaps the most important and overlooked component to successfully landing high-paying jobs online is the final proposal that you send to the client.  Don’t be confused, I’m not talking about the initial written bid proposal that you submit online (nor the option to submit a bid through the freelancing site’s online portal).  I am talking about a well thought out and customized piece of material that you put together after you’ve had the opportunity to speak with the client on the phone and discuss the project in-depth.  This should be a long form document that you convert into a PDF and send directly to the client (preferably through email or through the freelancing website’s messaging center).

When Tyler landed the initial $5,000 project that we worked on, the customized proposal was the part of the process that sealed the deal and got us the job.  There are a few simple steps to keep in mind when putting these proposals together, which I have laid out below.  In a future blog post, I will break down the exact template that we use to put this proposal together (stick with us, there’s lots to learn).

Step 1 – Include a catchy, customized introduction.

When putting together the final customized proposal that you’re going to deliver to the client, the first thing that you want to accomplish is (much like the initial written proposal online) grabbing the client’s attention.  Starting out with a line or two relating back to specific pieces of personal information that the client gave you on the phone is a good way to start.  Mention something about their kid’s soccer game, the fishing trip they went on last weekend, etc.  Make yourself relatable and show that you listened to them while you were talking to them on the phone.  This is also a good place to express to the client just how much you are interested in doing an extraordinary job for them and talking about how much you really want to help them.

Step 2 – Walk the client through what you’re going to do for them in order to make the project a success and achieve the results that they’re after.

The next step in the final written proposal that has landed Tyler and I work time and time again, is to walk the client through the exact process that you are going to go through in order to deliver them the final product that they are after.  Mention to the client the very steps that you are going to take while working with them and how that is going to help them achieve the end result that they are looking for.

Step 3 – Include the price for the project with a detailed explanation of how you arrived there.

After a couple pages of delivering solid value (yes, a couple pages – this should be a long proposal full of value bombs) it’s time to throw a price at them.  Whether you are working on a fixed price or hourly rate, the process is the same.  Remember that the client shouldn’t have heard anything about price from you yet in any of your interactions with them.  The first time Tyler mentioned anything about price to the first client we worked with was in the final written proposal that he sent over.  The idea is to get the client already decided that they are going to work with you before they even see dollar signs.  Once you hit them with a price (if you’ve done a good job up until now) they will do anything in their power to figure out how to work with you and your price point will be irrelevant.

Step 4 – Make yourself sound exclusive, end with positioning yourself as a scarce resource, and include some testimonials (if you have them).

The last thing that Tyler did when he landed our first client was to close out the proposal by telling the prospect that we had “a lot” of work on the table and that if the client wanted to work with us, he would have to respond within 48 hours so that we could see “whether or not we could fit him into our busy schedule.”  Regardless of whether or not you have work on the table, nobody wants to work with someone who isn’t wanted.  Make yourself sound exclusive and give the impression that your time is important.  Another thing you’ll want to sign off with is a couple testimonials from past clients that you’ve worked with (if you have any).  Providing some social proof always goes a long way.  But if you’re just starting out, don’t worry.  When Tyler won us that first job on Elance, we hadn’t worked with anyone yet either and he simply included some relevant quotes and statistics to drive his point home instead.  Get creative and show the client that you’ve researched their case specifically and demonstrate how you can help them out.

Now it’s your turn: how to use this information and start hustling on your own!

There’s a lot more that’s gone into the success that Tyler and I have had but leveraging online freelancing sites is where it all began.  Throughout the process of winning our first job on Elance and turning our first $5,000 project into the start of an actual business, Tyler and I have learned a ton.  We’ve made a million mistakes and continue to do so but we grow from each one.  By learning from what Tyler and I have done and using the information in this post, you can save yourself a lot of time in getting one step closer to your goal of winning high-paying freelance jobs online.  The method that Tyler and I have laid out above is proven to work and if you go ahead and start implementing this on your own, it WILL work.  We’ve personally trained dozens of freelancers how to do this successfully, so this process has been validated many times and across a number of different industries.

If you’re thinking about trying to make some money by freelancing online, what are you waiting for?  Take action and go to a site like Upwork right now, start your own account, and get started.  Stop waiting for someone’s permission to start living a life with more freedom and autonomy.  Your journey to successful freelancing online starts now.

If you’d like a little more information about how to get started making money from freelancing sites online like Upwork, sign up for our FREE below:

Click Here to learn more about what it takes to succeed on Upwork.
  • bepstein90

    Wow.. the fact that you just posted all this information here for free is beyond refreshing. Most people try to hide the tactics that actually work, but you straight up just laid it out step by step! Thanks so much! Will be taking your mini course for sure 🙂

    • Thanks so much! It is always great to hear that the content we create is of value. Anything specific you liked the most or would like to learn more about? See you in the Course!

  • Epic blog post!

    Subscribed to check out the course.

    Saw that you mentioned Soap Opera Sequence (Brunson?) and Dan Kennedy. Any other favorite books/marketers you recommend checking out?

    Keen on seeing you pump out more exciting content.

    • Timothy thanks man! I’m also loving Ryan Levesque and the book “ASK” which is powerful. We leverage a lot of the “Survey” type funnels for our clients. Could be powerful depending on what you offer. Anything specific you would like to see content wise?

      • Hi Tyler – thanks for the response!

        Potential future content: A more in-depth look on how you conduct your Skype chats/negotiations would be of massive help.

        Quick one I had on the top of my head… What if you build potent copy and a high-converting-type funnel for your client yet a confounding variable leads to less-than-expected results? Do you offer a guarantee or is part of your compensation performance-based? Always wondered this…

        Cheers guys

        • Timothy sounds great. I think that is a powerful topic and much needed. We have a few articles in the works I think will add a lot of value in this area.

          The performance based contracts are tricky. I found they work best for joint venture type partnerships. They are often hard to track and without the right software, set-up and structure I usually avoid them. Often there is a lot of variables that are outside your control like you mentioned that could lead to awesome or subpar performance.

          Typically all the projects we do for clients are project based and not tied to any performance metrics. I think as you get into the $10k+ type of funnel projects clients expect a performance type model. We always want our clients to be successful and they all have a positive ROI on their investment with us. It is a great question and discussion item.

          I have found you just need to be picky with those type of partnerships because most people want to work on a performance type of partnership not because their product is incredible but because they simply don’t have any money. I can usually weed out those type of people pretty quick.

  • Babbzzz

    Thanks Tyler. Much appreciated. We’ve already established a presence on Upwork, but find it hard to land the big ones. I will try this out. Will definitely let you know how it goes.

  • I am new to the conversation but I love your suggestions. Have been a member of Elance/Odesk for a while and just started making some money on Upwork this month. I decided to market myself as a proofreader/editor/social media manager/seo writer. Unfortunately none of those are very big ticket skills. So, do you think I should train and try something else or stay where I am comfortable.

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