Welcome to The Leap! For this IG Live series, Wethos CEO Rachel Renock sits down with entrepreneurs who took the leap toward working independently or starting their own project.

In this episode, Rachel sat down with Alex Fasulo, also known as The Freelance Fairy. Alex is a financial freedom advocate and an educator and has spent nearly eight years freelance writing and teaching others how they can monetize their side hustle. She has monetized her own freelance career to over a million dollars, appeared on Forbes, Business Insider, and CNBC, among others, and has over 850,000 followers across platforms. Plus, her first book called “Freelance Your Way to Freedom” is out on November 15th. 

Watch the full interview here, listen on Spotify, or read below to learn more about how Alex got started with freelancing on Fiverr, how her business has evolved over the years, her biggest tax mistake, and what she predicts the future of freelancing will look like. 

Note: The following interview has been edited for clarity and length.

RR: You have found a ton of success as a freelancer, but you always say when you quit your job in 2015, you had no plans and no idea what you wanted to do. Tell us a little bit more about how you decided to go freelance and what your journey looked like.

AF: When I quit my job in 2015, I had absolutely no plan. I just knew I couldn't work at [my job]. So I tried out a bunch of things, and I really only stuck with freelance writing because it was the most lucrative the most quickly, and I was like, "I have to pay my rent, so I'm going to pay attention to the thing that might do that for me and not the other things that aren't going to do that for me." So yeah, it happened to be freelance writing on Fiverr. I never in a million years thought $5 orders could add up and pay rent in New York City, but I obviously discovered I was wrong with that, and it was just kind of crazy.

I always say to people, don't put so much pressure on yourself to have this perfect plan in place because you can't have the perfect plan in place, and it's okay to try out a bunch of different side hustles. I know people who love drop shipping, they've made so much money on it. I didn't like it. My stint with real estate has been iffy. I'm making jokes about it, but I had to try it out. So freelance writing, it's just what stuck for me, and I really think freelancing is something that can welcome in so many different types of workers and personalities. I really think it's kind of this umbrella thing that has a lot more potential for people than they might realize.

RR: You have amassed a really large following, you run a podcast, and you do a ton of stuff. How do you manage your time and how does that impact your current freelance business?

AF: I would say for about the first four years I didn't have time to do anything like that. It was just me, my laptop, Fiverr, and freelance writing. And I was working 10-12 hours a day and I was happy doing it — I had a good thing going, I didn't want to mess it up. It wasn't really until around the four or five-year mark that I had the idea, and people kept saying to me, "How come you don't have somebody else helping you out in your business?" I'm like, "Well duh, I should."

So I brought on one guy to split the orders with me around the five-year mark, and that is when I started getting the time back to then start posting on social media about what was happening in my life. And then I started growing the team more and more to the point now where I have the time to write a book or do a podcast. But I'm always open about that with people. I was not doing that and doubling up with freelancing my first few years, but I also say you don't have to wait four or five years to hire help either. I definitely was very stubborn and slow to do that, so I always encourage people to possibly consider that more at the two-year mark than five.

RR: For you, what was the inflection point where you suddenly were like, "Okay, I've got to get somebody to help?"

AF: It was at a point where I felt like I was almost turning away business because I couldn't physically do it all myself. So I was like, "This is just silly. This is just crazy that I'm turning away business. I shouldn't be doing that." I started very slow with one other writer with me for a year and a half, so it really took me about six years to get to the point where I felt comfortable having more of a de facto agency now. It took me a really long time because it was like I don't want to mess it up. It was my baby forever. So now that I've kind of done it, I share it with everyone on how they don't have to wait as long.

RR: I love the content you're creating. It's real, it's super engaging, it's funny — particularly the videos where you're helping people focus on making more money and talking really transparently and explicitly about it. You mentioned that you went from selling $5 writing on Fiverr to then a thousand dollars a day, which is just wild. Can you help us understand a little bit of the strategy behind that over time? And specifically, did you focus on more work with smaller price tags versus a higher price tag and less projects?

AF: I kind of realized quickly on Fiverr that it's all about the reviews, it's all about the social proof, and if you can get more five-star reviews, they're probably going to push you out more to their algorithm. So early on, I just kept my head down. I wrote for very cheap rates. I didn't care. I just wanted as many reviews as I could get as quickly as I could get them. And I figured out like, "Oh, if I have 100 five-star reviews, then if I eventually get a one-star review, it's not going to mess with the average and then I can breathe." So for the first six months, I just kept my head and built momentum behind it where I was able to slowly start raising my prices because I had the proof to back it up [with] all these five-star reviews.

It grew gradually the first two and a half years, then really, though, the biggest jump was [from] joining the Fiverr Pro program, which they still have right now, and that's like the top 1% program. So [in the program] they want you to charge $100 instead of $20. When you had been previously charging $20 for something, and it's suddenly a hundred, that is how you jump all of a sudden way into the six-figure realm kind of really quickly which is what happened to me, and it was really bizarre and amazing and scary all at the same time.

RR: You mentioned that you've gotten clients through Fiverr and Upwork and LinkedIn and your professional network. I’m curious, has it varied a lot in terms of quality of project or client depending on the platform or how they find you?

AF: Yeah, I mean I would say most of the clients that I've worked with over the years always end up being small businesses, startups, and other freelancers.

I would say Fiverr is still the number one place for volume. To me, there is still nowhere else you can find that many people. But I would say people who find me through email, social media, and LinkedIn tend to have higher budgets, and tend to be a higher quality client. But with a higher quality client there's more back and forth, there's more having to prove yourself. They don't just hand you a thousand dollars and walk away. Whereas on Fiverr, you can wake up and someone could quite actually spend a thousand dollars overnight, auto book you for something, and that's it. They don't need to call you.

And I still love that part of Fiverr because I don't love handholding. Customer service has never been my forte. If anything, that's my downfall as a freelancer because I'm just kind of like, "Don't call me." And they're like, "Oh, I won't book you." I'm like, "That's fine. I'd rather you just not book me because please don't call me." You have to have your boundaries somewhere. You have to be able to unplug, or you're going to go crazy with it. So that's one thing I do like about Fiverr, the anonymity.

RR: So we got a couple of questions about finding your niche. How did you think about finding that niche and then do you feel when people find their niche, is it something that they should adapt to changes in the market? Or is it no, double down, this is what I've always done, I'm great at it. Let's go.

AF: Okay, so the niche question is hard because there are multiple correct ways to go about it. This has just been me, [but] I never for a single second worried about a niche, and I literally still don't. When I got on Fiverr, I just opened the most generic gig ever: I will write for your blog. And I think that was part of my quick success with it because I wasn't like, "I will only write about finance or I will only write about the environment." I was just like, "I will write about literally whatever you pay me to write about because I need to pay for my rent." And honestly, I still have quite a catch-all approach to it. I've never niched down with the type of copywriting I offer, and I really don't think you have to.

And I think a lot of people get very tripped up on that. It's part of the perfectionist, the self sabotage thing that will stop them from getting started. Because again, they think, "Oh I need a niche down. I need to know my niche." First of all, you could never know your niche unless you dabble in 50 things and then maybe something will jump out at you, and you won't even know that that's going to bring you joy. So I'm a big, “don't worry about a niche” person. I know there's probably other people who maybe have done this totally differently, so I'm not saying that is the only right way.

RR: So you have a new book coming out, and I want to dig into this a little bit. It's called Freelance Your Way To Freedom, and what I love is that it goes into the good, the bad, the ugly — all the things. One of the toughest areas to navigate that we got questions about is taxes. And I want to ask you, if you're willing, can you share the worst tax mistake you made and what you learned from it or what others can learn from it?

AF: I mean, yeah, at this point I've been so transparent with my finances. Why stop now? So I got destroyed in taxes for 2021 because I jumped from an income class that I had been in the previous years. I jumped into a larger one without realizing that I wasn't qualified for certain deductions that I was previously qualifying for. Now I have my best friend and she's a CPA so she's explaining all of this to me, so I actually freaking understand it now. But I paid over $100K in taxes last year, and it was just terrible.

And that happened because I was registered as an LLC, and now I switched it over to an S Corp. I'm not a tax professional so I can't really give you an explanation on why that's better, but basically, I'm paying myself a salary from my business now, and that is going to severely lower my taxable income for this year. So if you have a freelancing business that's making six figures, please consider an S Corp. That's all I'm going to say. This is not licensed tax advice, but I got destroyed last year.

RR: I want to zoom out here for a second. From your perspective, what do you think the future of freelance looks like? And specifically, is there anything that you think will change in the next 10 years or is there anything that you think will stay the same?

AF: Okay, so I am a very forward-facing type of person — I don't fear the future or anything like that. I absolutely think freelancing is actually going to be a pioneering portion of our economy where freelancers are going to be working in tandem with AI or robots. I think we're going to be working together very quickly and much quicker than people probably want to think about.

And I actually think due to how agile freelancing is, since you're not tied down into these contracts, and you're not salaried or whatever, freelancers are going to become the pioneers of working side by side with personalized tech that can automate everything they do. I'm really excited about it because when I've been using these AI copywriting tools, I mean, I'm sorry, it's kind of nice having a robot create an outline for you. I'm not mad about it. I have more brain power to think up. Maybe I'm going to think up my own AI tool. I don't fear it at all. I think it's really cool. I think it's going to make a lot of mundane things easier for people. I'm excited about it. But I really think the freelancing economy is going to be a huge focal point of this AI thing. I don't know, you guys can tell me I'm wrong. I could be wrong in two years. You guys can tell me then.

RR: Last question: Any final thoughts for folks who are looking to take the leap into a freelance business, whether or not that is by choice? Because I know there are a lot of layoffs and whatnot going around as well.

AF: Yeah, so I would say first, to anybody who hasn't been fired or isn’t in a dire situation, I would highly, highly recommend you dabble in it and double up while you work your other job because obviously, not everything is for everyone. I do think freelancing is welcoming to a lot of different types of workers and personality types, but if you are still at a job, I would just try dabbling in it for one to two hours per day, an hour in the morning and an hour at night while you work your job and just see if you like it.

If you are in a situation like I was in where you need to make your rent, my advice would be to get on Fiverr or Upwork tonight, open a LinkedIn service page and start plastering it all over your social media. Don't be shy. Own it. [Clients] will come to you, they will find you if you make that decision in yourself, you put that energy out there, it will attract people to you. That is how it works. And to not be scared, because it's amazing, and I actually think having to make it work is kind of a blessing because I see with people who have to make it work, they blow up so much quicker, so it could be a blessing in disguise. So don't panic. That's what I would say. Don't panic.