From his brother's couch to $300/hour on Upwork
Will Jennings' serendipitous story landed him on Upwork
I was curious and looked at freelancers making more than $100 per hour making a ton of money. There is a plethora of them! They are probably the 1% of the platform, but they surely disprove the “race to the bottom” belief so many hold.
I found Will Jennings there and I was so curious about his story. He multiplied his prices by 10 since he started on the platform. Really impressive story. I also love how he stumbled upon the skill he developed.
Check it out!
From his brother’s couch to freelancing on Upwork
You went from having your agency to becoming an employee to being an independent on Upwork.
What’s the story behind this? Why did you choose Upwork after all this?
Will Jennings: I graduated from College in 2020 and entered (probably) one of the worst job markets in recent history. I had a general business degree and no clue what I wanted to do. So, I decided to go sleep on my brother’s couch and learn what he was doing. At that time, he was working as a paid media manager for a Dentsu agency in Atlanta, GA. Also, he had 1 or 2 freelance clients as a side hustle. So I sat next to him, was trained in media management and helped him manage his side hustle.
So long story short, because it was 2020 and everyone was cutting full-time staff and moving to remote work, there were plenty of clients to be found. We started an agency and hired remote workers. By 2022 we had a full-scale agency servicing Fortune 500 clients.
In Q3 2022, we sold the agency to another agency and worked for them. I spent a year working for that agency before confirming what I already knew: working for an agency sucks, and I only enjoy working for myself. I had an Upwork account as a side hustle and it was quickly growing to the point where it could be the main hustle.
In December of 2023, I left that agency and started freelancing. Upwork provided a marketplace where I could bid on jobs, get client testimonials, send invoices and contracts, etc. So, I was fine paying the fees for all those benefits.
Why work on Upwork?
I’ve noticed your social media content directs to your site which links to your Upwork profile. I’m assuming Upwork make it easier for you to manage clients. But I’m curious to hear your thinking there.
Why not use a Stripe account to charge people directly and circumvent the Upwork fees? Can you explain your thinking about redirecting people to your Upwork profile?
Will: While you do pay more fees to host the projects on Upwork, there are many benefits gained by staying on the platform. In fact, it’s my theory as to why I’m doing so well right now. Each job and each review is additional SEO for my services and name on Upwork. If you type my name or any keyword related to my services, my profile will show up first because I have the most jobs and content related to that search.
Upwork works great as a way to bid on jobs, but the money really starts flowing when you no longer have to bid on jobs, but customers just message you directly. I’m building a reputation on Upwork. Now, I intend to diversify my internet presence on social media and my website, but I will never completely leave Upwork because it has been so good to me.
How to handle bad apples?
When you’ve done 200 or so jobs on Upwork, there has to be one or two bad apples. From my experience, it usually happens at the lower price point and becomes more rare with higher pricing.
What’s the worst situation you’ve experienced so far on Upwork? How did you manage to get out of it? At what price point was it?
Will: It has happened a few times. Whether you are on Upwork or not, bad clients can happen. That being said, I was prepared for this, and my response was always to refund a client for work they were unhappy with before they had the opportunity to give me a bad review. In the beginning, your reviews are everything.
Anyway, I had this one client who hired me to help them set up their Facebook and Instagram Shop. They had their product catalogue on Woocommerce and the job was to sync their online product catalogue with their Facebook Shop. At that time, the Woocommerce to Meta integration was completely broken. It was the first time I had seen this issue, but the client expected me to have already seen this issue because of my $300/hour rate.
They then started hiring other freelancers and doing things themselves which made the situation even worse. They were blaming me for problems out of my control even though I offered solutions to them.
In the end, I partially refunded them, and we went our separate ways. It was difficult to swallow, but I couldn’t fully refund them because I had spent so much time on the project. They gave me a bad review, and I had to live with it for a while.
That being said, I am now able to consult people through these integration issues before the project begins.
From $30 to $300 per hour
Impressive growth of your hourly rate. You did 30, 50, 70. But when you reach 100, you raised your rate way more than before to 150, 200 and then 300.
How did you choose those numbers? Did a shift happen around the $100 mark? What was your pricing strategy and how has your offering evolved?
Will: In the beginning, I was doing jobs for free or at the lowest rate I could get just so I could get reviews and testimonials. I would recommend this to anyone new to freelancing. I started to raise my rates when I went full-time with it in 2024. I started to have more work than I could handle, so I raised my rates because demand was high and supply was low. Even at $200/hour, I was getting more work than I could handle. Now, at $300, I feel accurately rewarded for my time and knowledge, and I have a steady but not overwhelming stream of clients. You get what you pay for, and my goal is to not only fix your issue but also to leave you with the knowledge to prevent future issues. $300/hr allows me to dedicate personalized attention to each client and job.
3 juicy links of the week
Made day 10 out of 100 for my “A Dollar A Day” Challenge
It’s been a hell of a journey so far, and I can’t believe I made 10 days already. But I also can’t believe there’s 90 days left! Wish me luck!
I survived on $0.01 for 30 days
I love those challenges. Why? Because they force you to push the boundaries of your imagination. You really have to think outside your preconceived notions and mental blocks. In those situations, you have no choice but to try shit and see what works.
Advice on how to build a sustainable business
Borderline generic advice but pushing you in the right direction!