Happy Thursday!
Really quick before I dive in, I get this question all the time: “How do I actually make money with all these AI tools?” Thats why I built Playmakers- my AI agency program where I teach you how to charge local businesses $500-$5,000 a month to set up and manage AI for them. You get three live calls a week, plug-and-play automation templates you can deploy for clients on day one, a 5 Day First Client Challenge, and my personal lead lists with businesses in your area ready to connect. 120+ people are already in the community building agencies right now. Go to playmakersai.com and check it out.
Okay, let’s get into it.
Searches for "hire a writer" on Google are higher right now than they've been in five years. (That really surprised me, because when ChatGPT came out, those searches dropped.) A lot of companies assumed AI would handle all their writing, so they stopped hiring people. Over the last two years, they've changed their minds, and searches have climbed right back up. Companies don’t want AI slop. And they're paying well to prevent that.
Two weeks ago, Steph, a writer from Austin, drove up and hopped in the Cybertruck with me to explain how she gets paid $900 to $1,200 per blog post by tech companies like Zapier, Jotform, and Softr. Each article takes her about five to six hours. She has no coding background, and she started on Upwork back in 2016 with basically nothing. Today she's bringing in around $6,000 to $7,000 a month, mostly from writing, and she left her full-time job just three weeks ago to do this on her own.
This business is fully remote, so you can start it from whatever city you live in. I'm going to walk you through exactly how. If you want the full conversation, watch it on YouTube, or listen on Spotify or Apple Podcasts.
What the Business Actually Is
B2B software companies need long-form blog content, usually 2,500 to 3,000 words per article, to show up in Google and increasingly inside AI tools like ChatGPT and Claude. The assignments sound like "Claude Code vs. Cursor," "8 Alternatives to QuickBase," or a step-by-step tutorial for building a specific automated workflow. The company typically hands you the keywords they want to target, so you don't need to be an SEO expert going in. You just need to know the basics, like how to structure headings and keywords.
What they're really paying for is someone who has actually used the tools. Steph spends most of those five or six hours signing up for the software she's writing about, clicking around, grabbing screenshots, and reading Reddit threads to see what real users are complaining about. If people are griping about confusing pricing, she goes and figures out the pricing herself. A chatbot can't fake that kind of firsthand research, and it's why these companies will pay four figures for a single article.
Step 1: Pick a Niche
Before our conversation, Steph hired a handful of freelance writers on Upwork (each making over $3,000 a month) for 20-minute calls about how newcomers break in. None of them had a writing degree. What they all agreed on was that your first month should be spent figuring out what kind of writing you want to do: book editing, website copy, ads, scripts, email, SEO blog posts, etc...
Start as a specialist. Steph began as a generalist and said it took her a while to realize people hire the writer who's obviously great at one thing. Pick something you already have a glimmer of interest in. If you love Texas barbecue, go after barbecue brands and e-commerce companies selling grills and rubs. If you tinker with AI tools on the weekend, target SaaS companies.
beehiiv launched Community- a feature that takes your newsletter replies out of your inbox and puts them somewhere your whole audience can see them- and talk to each other about them. Every newsletter and podcast you drop posts to your feed automatically. You don't promote it. It's in front of the people who already love your content, and the conversation keeps going long after you hit send.
You can add Community access to any subscription you already sell. It takes just minutes to set up, and you can decide on free, freemium, paywalled, or paywalled with upsells inside. All of it works on day one. Get more juice from everything you produce. Use code CHRIS30 for 30% off three months on beehiiv.
Step 2: Create a Portfolio Before Anyone Hires You
This is one of the rare businesses where you can solve the chicken-and-egg problem by yourself. You need four or five samples that show range, something like three blog posts and a landing page. Nobody has to pay you for them. Write an article about what makes Franklin Barbecue different, or a comparison of two AI tools you actually use, and put them on a simple site built with Hostinger or Replit. Who's stopping you? No one.
Step 3: Find Clients on Upwork and Through Cold Pitches
Ten years in, Upwork is still where Steph finds a lot of her work. The leads are sitting right there waiting for you. When she's actively looking, she applies to about ten jobs a day, choosing ones where she can explain exactly how she'd help that specific person and where one blog post could turn into an ongoing contract.
Outside of Upwork, learn the cold pitch. Keep it to four or five sentences. Introduce yourself, mention something specific you genuinely like about their company, link your portfolio, and say you'd love to connect. Steph tried a new beef protein powder, emailed the founder to tell him the flavor was awesome, asked in that same message whether he needed a blog writer, and got hired. Another time she listened to an entire podcast episode from an agency before pitching them, referenced a specific detail, and they called her right away. That extra homework is what gets you noticed.
Step 4: Price by the Project
Starting out, $30-$40 an hour is a realistic range on Upwork, especially with a solid portfolio and a tailored pitch. Steph worked cheap in the beginning too. One of those early clients turned out to be Biggie Smalls's son, who was launching a CBD brand, and that relationship grew into press releases and PR work she'd never done before. Take the reps early and raise your rate as trust builds.
Once you have some experience, switch to flat project quotes. Before quoting, ask roughly how many pages or words the job involves and whether they have existing copy you can look at, since rough copy takes longer to fix and no copy means starting from scratch. You can still do the math off an hourly rate in your head, but give the client one number so nobody gets surprised. If they're okay with it, run a note-taker like Granola on your kickoff call so you can pull up deadlines and details later.
After you get a few clients, make this writing hustle a goldmine by connecting it to HighLevel! HL will handle the follow-ups, bookings, and to prevent leads from going cold while you're typing away. Landing the work and running the operation are two different jobs, and the second one is where it’s easy to fall off.
HighLevel handles the CRM, automated follow-ups, booking calendars, text and email campaigns, all in one place. The system handles reputation management, handles reviews, chases leads, and books calls for you. You can also white-label it and resell it in your niche. It’s a no brainer add-on for your clients that already trust you. My readers get 30 days free at gohighlevel.com/tkopod.
Step 5: Use AI Where It Helps Most
The biggest mistake Steph sees is writers trying to automate the entire process. They spend hours configuring tools, the output still isn't right, and they burn out. At Zapier, she copy edited a report on how companies use AI successfully, and AI handled only about 18% of the workflow, usually a step or two with a human reviewing the result.
She uses Gemini for processing video and audio, Claude for marketing content, and ChatGPT for research. For tutorials, she screen-records herself building the workflow while narrating her thoughts out loud, then has AI turn that recording into a first draft using her own template. The ideas and structure are hers, and she estimates 70% to 80% of the final words are hers too.
Step 6: Expand Every Account
Once a company trusts you, they really don't want to go find another writer. Look for ways to do more for them. Offer to upload the posts yourself, pitch a series instead of a single article, or pick up their landing pages. Steph has turned one-off projects into contracts that lasted years.
The Math:
At $1,000 per article and five to six hours of work, you're earning roughly $165 to $200 an hour. Five articles a month is $5,000. Ten articles is $10,000, and that's still only about 60 hours of work spread across the month. Add a side offer on top, like Steph's college essay coaching at $450 per five-hour package, and you've got a real income with almost no startup cost beyond a basic website.
Spend your first month picking a niche and writing your samples. In month two, apply to ten Upwork jobs a day and send a few cold pitches every week. Even if your first client pays $300 an article, you're building the portfolio and relationships that get you to $1,000.
Again, if you want the full conversation, watch it on YouTube, or listen on Spotify or Apple Podcasts. By the end, you will have everything you need to start this writing hustle for yourself.
You can just do things. Go do them.
Lastly, I'm always looking for cool, unique businesses to share on my podcasts. If you have one and are comfortable sharing your journey, drop your info here!
Have a great week!
Chris
P.S. I share deep dives on business ideas and complete playbooks three times a week on YouTube and every podcast platform.
