How I Make $30K a Month by Spending $400 on Upwork

Ivan: This episode is a bit different from the previous one — a bit longer, more of a mini podcast, and I am joined by Nikola. Nikola is a dear friend of mine. He is also from Macedonia, so we had the privilege of recording this interview here in my studio.

Ivan: He is one of our earliest users. He beta tested Lancer for us and helped validate the product itself, and he has been with us since the beginning. We will not talk that much about how he uses Lancer, and this is not really an advertisement for Lancer. The focus is his actual storyline: how he started at 20 years old, part-time freelancing on Upwork for $15 and $50 projects, and scaled that to a full agency working with enterprise clients on six-figure deals — all through Upwork.

Ivan: Because this is a longer episode, there are chapters below so you can skip to whatever is most relevant to you.

Ivan: Do you remember your first Upwork client, your first online payment? What was that experience like?

Nikola: I do. I was applying to every job. I was positioning myself almost as an expert even though I was not an expert, and my pitch was: I am an expert trying to build out a portfolio on Upwork, so I will do it for a cheaper rate.

Ivan: So even back then that worked. That is also what I did when I started.

Nikola: Pretty much. I had a $15 project that I worked on for two weeks. Flat, not hourly. And I was so excited to work on it — I remember it was New Year’s Eve and I went to bed early to wake up in the morning and continue working on the project. My birthday is the 3rd of January, so I worked through my birthday and everything. I was so excited to make my first money online.

Ivan: I wanted to pull up the profile here to drive this point further. This is Nikola’s profile: hundreds of thousands of dollars earned, hundreds of jobs closed, six-figure jobs. But if you scroll all the way down — this is all public data — you go back six years and you find a $25 job, a $50 job, a $60 job, a $40 job. Then a $600 job, then back down to $150, $380, $800, $200. The average is going up, but he was not afraid to pick up those jobs while he was building his profile.

Ivan: Now filter by largest projects. Three years later — that is not a long time — he has a six-figure job with an Upwork enterprise client, a $30,000 job, five-figure jobs, four-figure jobs. You start at $40 and then you have six-figure projects.

Ivan: The gap between those jobs is where people get frustrated and quit. The ego works against them: why would I work with this guy for $50 or $100? They cannot see that they are building up their Upwork profile. This is your digital storefront. You are building legitimacy at the beginning — you are not making profit at the beginning, like in any career. Think of it as someone paying you to learn on the job. And once you are a legitimate specialist five years down the line with all of that proof behind you — hundreds of jobs, 100% Job Success, Top Rated Plus, hundreds of thousands of dollars earned — then you get the enterprise client and the six-figure deals.

Ivan: When did you transition Upwork into an actual channel where you make money and it becomes stable income?

Nikola: The way I looked at it, freelancing might work, might not, but at the end of the day I would build out a design portfolio. My actual plan was to start applying for jobs and get my first design role. But I got one client, then a second client — the second one was around $40 flat. Then I had a four- or five-hour hourly contract that made me around $70. And that just scaled and scaled, until I got to a point where I was making $400 or $500 a month.

Ivan: How old were you back then?

Nikola: I think I was 20.

Ivan: In Macedonia that is almost above the average salary. And it was not full time?

Nikola: It was not full time. I was still a student — this was on the side of doing college, so really not related. Then I remember the first time I hit $1K per month. That was the moment of: okay, you can make some serious money here. All pure Upwork, 100% Upwork.

Nikola: After a couple of months of making $1K I was at a crossroads: continue college, or drop out and go into freelancing. I calculated what my salary would be when I finished college, and I was already making almost double that. I was not passionate about what I was studying, so it did not make sense to continue. I dropped out and focused on freelancing and on building out my skill sets — more than on having high rates. I wanted a solid base, and I was more excited to learn and grow than to focus on the money.

Ivan: So you have been on Upwork since around 2019?

Nikola: December 2019, yes.

Ivan: Everyone says Upwork is not what it was. Can you compare Upwork then and now, and make the argument for each?

Nikola: I would say Upwork is better now. You have to be more strategic about it — before, the start was a bit easier — but once you get the ball rolling, Upwork today is a better platform.

Nikola: A few reasons. More serious clients come to Upwork now; there are a lot of enterprise clients. New jobs pop up every day and a lot of people are finding opportunities in those new roles. And the deal sizes are different. Back then, when I looked at the top people in my niche, the biggest project most of them had was $5K to $6K. Right now I have contracts over $100K on the platform.

Nikola: The other advantage is fairness. Yes, the competition is larger, but Connects mean people are not massively applying to everything — that part is regulated. Back then, if you were not Top Rated or top in your niche, you could forget about invites. Now it is a much more even playing field. Even if you create an Upwork profile today, if you apply to jobs regularly you will start to get invites — the algorithm will reward you. Overall the platform is a lot more built out and polished.

Ivan: So why do you think there is a whole separate group on Upwork that is constantly complaining? What are they missing?

Nikola: Let us ask them where they get their clients from instead. Running your own business is not easy, there are challenges. But the main argument people use against Upwork is the 10% fee, plus low-quality jobs. There are always going to be low-quality jobs — it is hard to get a good-quality job. If it were easy, everyone would get it.

Nikola: On the fee: break it down against other platforms. Stripe alone has a ~3% processing fee. With Upwork you get an escrow service, so you are guaranteed to get paid for your work. Contracts are handled for you. And you build a reputation you can then use on other channels.

Ivan: Public earnings, public reviews. You are a Webflow expert, Top Rated Plus, hundreds of thousands of dollars earned on Upwork, hundreds of positive reviews. I have seen a lot of agencies and freelancers put that on their own website — that they are a Top Rated Plus expert. That is one of the advantages of building Upwork as a channel.

Nikola: Exactly. When I reach out to clients I show them my website, but I also show them my Upwork profile, because that is the biggest trust builder I have. I do not have a big audience on other platforms, so when I reach out I leverage what I have on Upwork, and it helps a lot.

Ivan: Can you break down the acquisition channels you use right now, and how Upwork compares to the others?

Nikola: Right now Upwork is our main channel for client acquisition. We also built partnerships with a few other agencies, as a subcontractor — but the problem there is lower rates, inconsistent work, and getting the work they do not want to do. You always get the toughest clients that pay the least.

Nikola: The other one is LinkedIn. LinkedIn is a pretty good channel, but the process of getting a client there is a lot more expensive and a lot more time-consuming. You have to warm people up and almost hunt them down. I just got a client on LinkedIn that I had been chasing for seven months, giving them suggestions on how they could improve. The way she eventually responded was: okay, you have been hunting me for seven months, our Webflow agency is not working out, let us schedule an interview. It is a much longer sales cycle, which is not ideal for a turnaround service like Webflow — most of our clients just need a website, and once the website ships, that is pretty much it.

Ivan: You mentioned a number that stuck with me: on Upwork it is at least four clients a month, and on LinkedIn it is one client in four months. That is almost 16 times the client volume.

Nikola: That is correct. About 80% of our clients currently come from Upwork. We are closing down the agency-partnership channel because the math does not work well enough for us to scale it. So Upwork and LinkedIn are our main acquisition channels going forward.

Ivan: I am going through some of the numbers you shared with me for July. This is insane ROI. You spent around $400 in Connects, and $6.6K was paid out on Upwork from that deal flow. That is roughly 15X on money actually collected inside the month. I do not see any other platform where you can just plug in, spend this much and get this much without extra effort — especially since you solved the friction of scaling proposal sending with Lancer.

Ivan: We have talked about all the good things. What are the worst parts? What is the hardest thing about the channel?

Nikola: The hardest thing is being under constant stress of performance, because you have to perform well for clients to leave you good reviews and for you to keep growing. It is not like other channels. You always have to be good at what you do, and do it consistently over years.

Nikola: Which is also a plus — you build skills, you build skills in managing people, and you need bulletproof processes. But the biggest negative is that you are at the mercy of the people you work with. You have to be selective about who you choose to work with, to make sure they do not turn out to be crazy and leave you a bad review for basically nothing.

Ivan: Everything on Upwork is monetised now — Available Now badges, boosting your profile, boosting proposals, tools and strategies. How do you break down where and how you spend Connects? How do you approach discovering jobs and sending proposals? What do your invitation numbers look like?

Nikola: I approach it with testing, like everything else. When the Boost Profile feature came out, I boosted my profile — I did not see a huge ROI in that. When boosted Connects came out I started using those, and experimented month to month, using it and not using it. At this stage, we boost every proposal we send out. The way I see proposals is almost as paid ads: you spend a few bucks to be seen by the right eyeballs. That is how the majority of other channels work too.

Nikola: On invitations — that was a big part for me. Because we had so much client volume, for about a year and a half I did not apply to a single Upwork job. Now that we are scaling, with three team members on board plus my co-founder, I have gotten back into the habit of applying to jobs regularly. What I noticed is that the more you apply, the more the algorithm rewards and boosts you, and the more invites you get.

Nikola: For reference: I did not get an invite for a year and a half, almost two years, while I was not applying. When I started applying again I still did not get invites for the first few months. But once I started applying regularly, pretty much daily, I now get at least three official Upwork invites a week. I also get a lot of DMs on Upwork — people who do not even post a job, they just message you asking if you are interested, or to schedule a call. So: two to three official invites, plus one or two of those messages per week.

Ivan: On this topic — increasing the number of inbound organic leads you get on Upwork for free whenever you increase the volume of proposals you send — we have concrete data to back it up. Nikola shared his stats with us, and if you overlay them with his Lancer dashboard you see a clear parallel between the number of proposals he sent and the profile views and invitations he got in the same period.

Ivan: This chart runs from May to September. May into June is increasing, then July hits a peak — that was his biggest month yet. Then in August he was at full capacity, so he lowered the number of proposals sent. And that had a direct correlation with the extra inbound leads he got. His profile is not boosted — this is completely organic. In July, when he sent the most proposals, he had the most profile views, which also produced the most invitations. In August the proposals came down and the invitations came down with them.

Ivan: A lot of people say they rely only on invitations and inbound and never send proposals. Even then: if you are looking to scale and you are not at max capacity, you should be sending proposals, because the Upwork algorithm will give you even more invitations.

Ivan: What is your biggest advice for someone looking to start this journey right now, going into freelancing or an agency as a service provider?

Nikola: Pick a platform. I am biased towards Upwork, so I would recommend Upwork. Do not focus on the money straight away. Focus first on building out your profile and your portfolio, and getting a few good reviews. After that you have the social proof to hunt bigger clients and go for the bigger fish.

Nikola: After a couple of months of doing that, if you stick to it, you will see the rewards coming in. And once you see them, there is no looking back — you just look to scale and go forward. So put your head down for the first few jobs. Drop your ego. You might have to work for lower rates. But if you do a good job, the rewards are not comparable to what you gave up in those few months. This is a long journey — focus on the long-term vision and do not get set back by short-term outcomes.

Ivan: So you think anyone who is genuinely a great service provider, with the time, resources and conviction, can start even today on Upwork and establish it as their biggest acquisition channel?

Nikola: Pretty much. Give it two to three months. Really give it two to three months: apply to jobs, maybe spend some money on Connects, focus on delivering for those clients and making them happy. You will see returns. I can almost guarantee that to everyone.

Ivan: We did not touch on positioning yourself with an offer. How much did you think about the offer inside the cover letter, and how you write it? I have seen users write a whole essay, and others send one or two paragraphs — and depending on the niche and the client, both can work. What is your strategy, and how important do you think the cover letter is?

Nikola: It is very important. It is the first touch point, the first impression you leave. Focus on the first sentence — the first thing that appears for them. I joke that you have to think about it like a LinkedIn post: you have to hook them with the first sentence, make it interesting enough to stand out, so that they open your cover letter at all.

Nikola: My niche is very competitive — there are jobs with 70 or 80 proposals. Out of 70 or 80 people, you need a strategy to stand out. That could be your first sentence, your profile photo, your overall profile. There are a lot of free resources online on how to do that and how to test it.

Nikola: On the length and the word choices, I would not focus on it too much at the start. Once you have experience working with clients and you have built out an ICP — who your clients actually are — you understand them a lot better and you understand how to communicate with them. My cover letter has gotten better and better as the years passed, as I understood who my clients are, how I can help them, and how to present my value to them. It is a work in progress.

Ivan: So it is constant improvement. Not something you do once and forget — you test it and iterate, because depending on the niche and your clients, different people have different needs and wants.

Ivan: Have you tried other platforms, and how do they compare?

Nikola: I tried Contra, which is a newer platform specifically for the design niche. To be honest I did not have much success there — maybe partly because I did not give it my all. But the main thing is that Upwork is so concentrated with clients. It is the biggest freelancing platform out there, and from a big pool of clients I believe that is the best strategy. Contra is a great platform, but it is very small.

Nikola: Fiverr is obviously the biggest competitor. I tried Fiverr, but the way I understand it, Fiverr is more about luck: people have to discover you, and you cannot be proactive about finding jobs, which I think is a big negative. You are at the mercy of the algorithm. On Upwork, even if the algorithm does not favour you, you always have the chance to apply and get a level playing field. On Fiverr, if someone has a long history you cannot compete with them — you have to cut your prices, and where on Upwork that takes a month, on Fiverr you are cutting prices for years to build up those reviews.

Nikola: I also gave Toptal a shot. I went through the whole interview process and I was accepted, but I ultimately did not want to go on the platform, because when we talked about my hourly rate I was already charging more than that on Upwork. It did not make sense to join a platform that brands itself as premium when I already charge more elsewhere — and on Upwork I can scale as an agency rather than being limited to being a freelancer.

Ivan: Thank you, Nikola. This was very informative. If anyone has questions, leave them under the video and we will answer them. Anything else to add?

Nikola: I would just encourage everyone who wants to start on Upwork to give it a shot and actually start. Do not be afraid. Do not focus too much on the negatives people associate with Upwork. Just give it a shot — you will see how rewarding it is. And if anyone has questions about Upwork or freelancing, feel free to contact me. I am more than open to giving out suggestions.