WEIRD Upwork Proposals that made me $100k

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I'm about to break $2 million on Upwork, and I know it's tough to get Upwork clients to respond. You...
Video Transcript:
I made over 1. 5 million dollars  on my first four years on Upwork Today I'm going to give you the five weirdest  Upwork cover letters that helped me become the highest earning Upwork freelancer in the world.  Watch this to the end because the last one has earned me over $150,000 worth of work and it's  gonna totally blow your mind - but first here's what most people are doing totally wrong in  their Upwork proposals: Dear Hiring Manager:.
. . -Why you talk like strange person?
I couldn't  help but notice your job posting on Upwork! -Oh thank you, Captain Obvious! I was excited to  see that you are seeking a Digital Marketer.
. . -Yeah of course I need ze Digital Marketer, I put ze job on "Upworks" myself!
My experience as a Social Media Manager is so much more  extensive than what I saw described in the job description. . .
-So you're like overqualified? I currently manage all of the Social Media accounts for a local restaurant including Instagram, Facebook, Twitter. .
. -Okay yeah, you're overqualified. I go find someone cheaper  now!
I believe that my skills can help you reach your goals faster. -Why you are talking about  self so much? I am the important one.
I am excited about the possibility of working with you on this  project. . .
-Oh no, maybe possible you go find other job! Please let me know if you would like  to see more examples of my work. .
. -No . .
. or hear more about my experience in this field. .
. -Haha  No. .
. . thank you for your time and consideration -No thank you!
Please hire me! Okay sank you, bye  bye! Let's get into the weird stuff that actually works.
Number five has won me over $100,000  worth of Upwork jobs. Hey I reviewed your job, and did a bit of background research. Would you  be able to fill in a few blanks?
Then add three really good questions that will help you scope out  the job and just get a better feel for it, like: Do you have any specific examples of what you  want as an end product? How long until you need a final version? and What's your budget for this  project?
Close it with something like: Thanks, looking forward to hearing from you on this. And  sign your name. The most important part about this: Just ask a few great questions.
The better  your questions, the more likely you'll be to get a response from the client. You can even take  this one further by asking a targeted question about the client's struggles and frustrations,  like "how is not having this done impacting your business or costing you money? " Go ahead - ask  about the client's frustrations!
They want to tell you about their struggles. Then it's just up  to you to decide if you're the one to solve those problems for them. And by the way on all of these  Upwork proposals you should be experimenting, and just seeing what fits for you, seeing what's going  to work in your niche.
Here's another one for you: Hey Mike, seems like an awesome fit. I've helped  other clients like ABC products and XYZ company boost their sales in the same way that you're  looking for. I attached an example so you can get a feel for the level of quality that I produce. 
Let's jump on a call and talk specifics? Tim. This one is short and sweet for a reason.
You're going  for maximum three to four sentences. Basically you just want to see how the clients respond, because  not every proposal has to be: it slices, it dices, it does everything you need. Sometimes you just  need to get in, get out, and just get the job.
This next one is especially good when you spend a  lot of time on creating awesome work examples: hey Jim I'm ready when you are. Send me a message and  let's hop on a call to discuss. PS - here's a few of what my work examples you can check out.
And  you just pop in a couple of your URL links to the work examples in your portfolio. This one super  short and that is very much intentional. Clients want to see what they can get with you, and if you  have great work examples then this one is going to put those front and center.
This next one works  super well when you have a very well-defined job, when you know exactly what you need to do. It's  for graphic designers but you can modify it to make it your own if you want: Hey Mike I'm ready  to rock on this project, here's what I need from you to in order to get started. #1: shoot me your  color scheme logo and design assets.
#2: press the green Hire Now button in the top right corner  and press Send Offer. #3 Send me a message for the times that you can meet for a quick 30-minute Zoom  tomorrow. What you'll get from working together: three different design variations, web optimized  image exports including PNG JPEG and WEBP, the fully editable PSD source file and final delivery  on October 17th.
Looking forward. Tim. When you're able to really fully scope out something it can  be very useful for clients to just look at your proposal and know exactly what it is that you're  going to be doing together how long it's going to take and what they're going to get on the other  side and what they need to do next in order to get started.
Now for the weirdest one of them all I have personally won over $150,000 from this one including one  single job for $25,500 It's beautiful and as long as you have great work  examples and a super clean Upwork profile then I promise that when you use it correctly it can be  tremendously powerful Know what else is tremendously powerful? Setting the notification Bell to all. It's the most powerful thing that you can do to help me on YouTube.
So I will make you a deal here. I will  tell you the story of how I discovered this and at the end if you are like WOW I gotta use that then  you gotta set that Bell to all do we have a deal I'm gonna hold you to it. Now that we've shaken  I'll tell you how I discovered it.
I was working for like a tiny little startup company and there  was somebody that I really really really needed to talk to his name was Guillermo he was the CEO  of a billion dollar business like super important very very busy guy and I was only able to get  him on the phone like once or twice but then we got to the point where like I need Guillermo to  approve a multi-million dollar deal before the end of the month. If we seal the deal, my company  makes millions but if we didn't then my business probably would have gone bankrupt but here was the  problem I couldn't get Guillermo on the phone he was crazy busy with people that were obviously  like a lot more important than like little old me and this tiny company that I was working for.  So I'm like, all right how do I how do I get this guy on the phone?
I just keep trying him on the  phone and it doesn't work nothing's working so I'm like all right let's try email. So I email him  once, send him a message. No response.
I email him very politely a second time. Again, no response. This  guy just would not respond to me!
You know that's okay but I'm like sitting here pulling my hair out,  because for two weeks he's just not responding and if I can't get this guy on the phone, then this  deal doesn't get done, and if the deal doesn't get done, then the company that I'm working for  literally shuts down and I lose my job and can't pay my bills, so my career was literally on the  line and I had to get this guy to just respond. I can't send him another polite email because  nobody wants somebody who's desperate and needy, right? So I'm sitting there, just like freaking out,  thinking "we gotta figure something out because otherwise everyone's getting fired here" but  then I had a moment.
Out of nowhere, I had what I can only describe as an epiphany. I knew EXACTLY what I had to write in order to just get this guy to RESPOND. I go to my laptop giddy like a  Schoolboy and I bash out this email and I hit Send - and I am absolutely certain that Guillermo  is gonna respond.
I have used the same strategy to get clients to respond on Upwork and have  earned over $150,000 because of this one weird Upwork cover letter: Attach your work examples, and write: so at this point you're probably thinking: Um hey  Evan? I think you might have forgotten to include the body of the message here. Guillermo thought  that too because when we had a multi-million dollar deal and a company's future on the line  and this guy hadn't responded to me in weeks, I sent him this exact message.
And he responded  two hours later saying: then I sent him the email that I really wanted  to send him, and blamed it on you know some glitch. I got him to RESPOND! And we did that  deal.
Speaking of deals: while you do that there's three more extremely  important things that I have to tell you about this number one if you want to take it to the  next level then use that person's first name like this. #2: try different things. For example  different variations.
#3: You have to try these cover letters out but understand that they're not  for everybody. But if you need a solid strong cover letter that's going to consistently get you  jobs then check out the next video right over here.
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