This is issue No. 2 of Financialicious, a weekly newsletter on the latest business, finance and culture happenings you must know. If you’re new here, kick off your shoes and make yourself comfortable. You can find past issues of Financialicious here, and you can send in recommendations here.

This week, I was poking around Robinhood’s new media property, reading about the effort to finance accessible broadband internet in America, gasping at the new world of deepfake Instagram influencers, watching the Jonathan Haidt controversy unfold, and doing a bunch of press interviews for a new survey about subscription creep.

Also, for our weekly column, we’re doing a retrospective on Medium its million-member moment (12 years in), and what it means for you.

(Recommendations for future installments of Financialicious are welcome. What are you vibing on right now? What’s an industry tidbit people aren’t talking about enough -- and what’s overblown? Last online splurge? Apps can’t you live without? Send TMI and then some to this email address: And if you know someone else who has great taste, have them subscribe to Financialicious here. New issues are published to the site every Monday, but as a subscriber you get them delivered directly to your digital doorstep one day early.)

Let’s eat.

Main Course

One column each week, usually about an industry trend, whitepaper, analysis or recent interview.

c/o Medium blog, April 9, 2024

“Medium’s Millionth Member Moment”


Medium, a self-publishing platform for writers and one of the largest websites in the world, hit a huge milestone this week. It also rolled out a big update in its fight to stop AI-generated writing from eroding the income independent writers earn on the platform. Medium continues to be underrated for audience growth.

Today, let’s put these updates into context and analyze what Medium’s recent actions mean for the online creator landscape — and ourselves.

Context, Part 1

The world of online business attracts people for a number of reasons.

  • Some people simply want to make more money in addition to their day job.
  • Others want their online business to one day replace their day job, and/or perhaps replace their spouse’s job, too.
  • Others still pursue online business because the typical career paths available to them either don’t work for their personal circumstances or don’t resonate with their values.

Whatever the reason, these entrepreneurs choose to buck the system. They’re exercising both financial and creative activism.

For years, common advice in online business circles has been to sell a service or product to a defined target audience. This advice has remained consistent, and it still works. For example, eCommerceFuel podcast host Andrew Youderian built a business called, which sold fishing boat motors. It used strategies like SEO and email to gather an audience of fishing enthusiasts, and was eventually acquired. Product-market fit: Check. Discoverable product: Check. Accessible audience: Check. One could say is a quintessential online business success story, and there’s no guru mechanism in the picture, which is refreshing.

In recent years, though, another iteration of online entrepreneurship has found traction: creatorship. Creators have two options for monetization.

The first option is to operate like an influencer. Build an audience, then give brands and advertisers access to that audience. This can either be passive by enabling display ads within your content (Think YouTube ads, or display ads on websites), or more active through things like individual sponsorships and paid partnerships.

The second option is to make your content itself the product, charging users a premium for access. In this approach, you focus on making the content itself – aka your product – relevant and valuable, with good craftsmanship. Patreon, Substack and OnlyFans are examples of platforms that power this creator approach.

Creator content is valuable. It’s often really good and engaging, so platforms like TikTok and Instagram, which mainly make their revenue through ads, have been experimenting with “creator funds” to encourage creators to create and get them paid. These funds have gotten mixed results, and the monetization can be corrupted at times because the funds are ultimately powered by advertising dollars. In my opinion, only one platform has successfully cracked the creator fund code without resorting to ads. That platform is Medium.

Medium is for creators. But its monetization program, the Medium Partner Program, doesn’t require selling to readers. Instead, when you enroll in the Medium Partner Program, stories you place behind Medium’s paywall will earn money based on member read time, along with some other factors. Writers can publish on Medium and get paid without having to sell directly to their readers. Users on Medium can read three paywalled articles a month for free, or they can become members for $5 a month and read unlimited paywalled articles; this money is what funds the Medium Partner Program.

Medium lets writers generate royalties income. Royalties are an income stream that is usually not available to us otherwise unless we are in the businesses of book publishing or IP licensing.

Context, Part 2

Up until 2022, Medium’s first and only CEO was its founder Ev Williams, who had previously co-founded both Blogger and Twitter. Williams has said his founding of Medium was a reaction to his time at Twitter, a desire to return to depth back when Twitter forced Tweets to be 140 characters or less.

Under Williams’ leadership, the Medium Partner Program was exciting, but also very bro. For example, in 2020 writers received monthly emails with leaderboards and metrics of who was making the most money on the platform. Like many online platforms, Medium’s readership exploded in 2020 when the arrival of the COVID-19 pandemic led to stay-at-home directives. At one point, Medium said it had over 100 million monthly active users, although the vast majority of those users were on its free tier. This readership then pancaked in 2021, the algorithms were iterated in weird ways, and writers revolted. Williams resigned in July 2022.

Then Medium did something that was very not Silicon Valley. Instead of hiring a high-flying, flashy tech CEO as Williams’ successor, the company hired one of its own writers.

Tony Stubblebine, Medium’s replacement CEO, had a tech executive background. But he had also been an active member of Medium’s community, serving as a founding editor for Better Humans and the Better franchises (Better Marketing, Better Programming, et cetera).

It’s interesting that Stubblebine is not doing the flashy stuff new tech CEOs usually do. He’s not Elon Musk-ing all over his platform. The long-standing hot take on Medium from the online commentariat is that Medium is tired, unfocused, and unworthy. I would argue that Medium is just now arriving at what it has intended to be this whole time: An independent, deconstructed and advertisement-free platform for independent writers around the world. Under Stubblebine’s leadership, Medium will become profitable this year for the first time in its history (that we know of).

Achieving this without ad dollars is quite remarkable in my opinion. Stubblebine’s quiet, restrained CEO style in an age where tech is dominated by cults of personality is also notable. This brings us to Medium’s two big updates from the past week.

Update No. 1

The first update is that, earlier this week, Medium crossed one million paying members for the first time. This includes members of its new “Friends of Medium” tier, which is $15 per month instead of $5 per month, with 100% of the additional membership fee going into the Medium Partner Program fund.

It sounds so simple, and yet it’s working, because people who read and write on Medium like to be around other independent writers. Medium is growing in what appears to be a healthy, sustainable way, and more paying members on Medium means more money in the Partner Program pot.

Update No. 2

The second update is that the Medium Partner Program has officially updated its terms and conditions with guidelines regarding AI-generated content.

“Medium is for human storytelling, not AI-generated writing,” reads the Partner Program email that was sent out on Wednesday. Medium will not allow content that was partially or fully generated by AI to be eligible for Partner Program royalties starting May 1. This applies to both disclosed and undisclosed AI-generated content. To achieve this, Medium’s guidelines say it uses “a wide variety of tools and technologies to detect and identify AI-writing and other AI content, combined with human review of any positive results.”

There will certainly be grifters who continue to try and pump AI-generated writing into and through the Medium Partner Program. But unlike other platforms, Medium has drawn a line in the sand on what type of content will be eligible for royalties. With AI-powered automation flooding platforms in the form of auto-generated posts and comments, Stubblebine’s strategy to go human contrasts the vice grip AI has on a lot of big tech right now.

What Does It All Mean?

I’m personally getting back into Medium this year. I weighed my various online business options, did market research, assessed my current time availability with having a day job and pivoted accordingly. I’m not saying you should publish on Medium, but if you’re trying to get something digital and/or entrepreneurial off the ground, keep asking yourself the hard questions so that the path to the finish line remains clear.

My position has always been that Medium attracts people who actually like to read. Medium has a high barrier to entry, like YouTube, which makes it less competitive from a creator perspective. I like that it takes more effort to publish. You’re publishing articles, which require more patience than social media captions and zingers. And when you play in Medium’s sandbox, the way Medium likes, there is good potential to both generate monthly royalties and get your writing seen.

Whatever your business-y, finance-y thing might be, ask yourself hard questions. For me, those are usually:

  • What are my short-term and long-term goals?
  • What should I start building this year that will move me in the direction of those goals?
  • What do I have time for, and what must I delegate?
  • What are my strengths? What comes easily to me?
  • What do I need to learn next?

Writing on Medium is one way I have incorporated entrepreneurship into my life over the last five years. It doesn’t have to be your way.

If you do have personal finance or lifestyle goals, however, it might behoove you to explore various forms of entrepreneurship in order to close the gap and bring those goals to life. ◆

A Free Masterclass This Thursday

My friend Sinem is teaching a free masterclass this Thursday about Medium.

If you want to use writing to grow your career, client book, or portfolio... you should be writing on Medium. Period.

Medium is still the best site for blogging and thought leadership for writers whose websites aren't yet generating a lot of traffic. Medium lets you grow your audience through writing. But how?

You're in luck. This Thursday, my friend Sinem Günel is hosting a masterclass that will show you how to grow your audience on Medium in 3 simple steps.

Register here.

➡️ FREE MASTERCLASS: “How to Grow Your Audience on Medium in 3 Simple Steps.”

Sinem has done influential things on Medium that others have not done. For example, she has interviewed Medium's CEO. I don't see any of these Instagram experts interviewing Adam Mosseri or Mark Zuckerberg, do you? That's access.

She has built her audience honestly and methodically. She has contributed to the top publications, as well as edited for some of them. Most importantly, she has helped other writers from many background types grow their audience by replicating her strategies.

You need Sinem's expertise in your life! She is a Medium super-user.

The best way to do that is to register for this free masterclass.

Medium is one way I grow my audience through writing. It's great. I have a workshop on it that outlines the approaches I took as someone with a media background.

But I wouldn't call myself a leading authority on Medium. That's a different distinction that requires deep knowledge of a platform's depth and breadth. It also requires proven experience.

Sinem Günel is one of the leading authorities on Medium.

She's knows a ton about the new Boost feature. She has both a large readership and a large client community, which together create the kind of brain trust that is unique. She's also SO NICE. Online creators like her are rare.

You've already made it this far -- put interest into action and go register for Sinem's free webinar now!

Reading Is Fundamental

News, snack-y business and finance explainers, past favorite personal bookmarks, occasional culture roundups.


Sherwood News debuted this week. The website is an editorial expansion of Snacks, the popular business newsletter run by trading and investing app Robinhood. (Sherwood News)

Broadband access in the U.S. is uneven, and contributes to inequity. Will $90 Billion be enough to solve the problem? Great piece from my CNET colleague David Lumb. (CNET)

Spotify Premium users can now turn any idea into a personalized playlist with AI Playlist in Beta.(Spotify)

‘AI Instagram Influencers’ Are Deepfaking Their Faces Onto Real Women’s Bodies. (404Media)

How I Built an AI-Powered, Self-Running Propaganda Machine for $105. A WSJ reporter had an Upwork freelancer built an auto-generating pink slime website that looked like local news — Yowza. (The Wall Street Journal)

Google researchers detail a technique that gives LLMs the ability to work with text of infinite length while keeping memory and compute requirements constant. (VentureBeat)

Parents Don't Want Schools to Confiscate Kids' Phones. A new survey highlights how fear-based parenting drives phone-based childhoods. (Nature)

Instagram will begin detecting and auto-blurring nudes sent via direct message. The recipient will be able to opt out and will be redirected to safety tips, per an in-article UX mockup. (The Wall Street Journal)

A plunge in FAFSA completion could spark an enrollment crisis for inbound U.S. college students this year. The number of students who filled out the federal aid form is down nearly 30 percent. (InsideHigherEd)

A NYC chicken shop replaced their cashier with a woman in the Philippines on Zoom. (404Media)

Taylor Swift Songs Return to TikTok. In a surprise move, Taylor Swift‘s songs have returned to TikTok after a 10-week hiatus amid a licensing dispute between the app and Universal Music Group. (Variety)

At least 38 Planet Fitness gyms have received bomb threats in the last month as the result of a campaign to protest the gym chain’s stance on transgender bathroom rights.The campaign has beenled by extremist social media account Libs of TikTok.(Advocate)

More than half of 2023's most challenged books in libraries have LGBTQ themes. (NBC)


One finishing takeaway.


Google Chrome browser extensions are such nice little productivity gems. Here are three free ones that I like:

  • Video Speed Controller. Watch any video at any speed. Great for watching video interviews on social feeds at 2x or 3x speed.
  • Nimbus. Screenshots of any web page, or parts of pages that have multiple windows. I like it more than FireShot because I screenshot emails in my Gmail inbox sometimes for design and formatting inspo.
  • ColorPick Eyedropper. Grab the hex code of any color on your screen.

What are some of yours? Reply and let me know.

Let’s make it a great week!