Today’s update is one you don’t want to miss. So grab your favorite drink, get cozy, and let’s unpack the latest from Substack… in true Online Writing Club style while I’m sitting on the couch after my daughter’s Peppa Pig party.
$100M Raised. Valued at $1.1 Billion. And Yes… Ads Are Coming to Substack
Substack just closed a $100 million funding round at a $1.1 billion valuation — led by the big dogs at BOND and The Chernin Group.
Add to that some very strategic names like Andreessen Horowitz, Rich Paul (the sports agent behind LeBron James), and SKIMS co-founder Jens Grede, and it’s clear:
It’s about a whole new phase of Substack.
For a long time, the company promoted itself as fundamentally ad‑free, built entirely around subscription revenue and direct reader‑creator relationships.
Over and over, co‑founder Chris Best said the team was focused on subscriptions and that ads weren’t central to their plans.
Since I know for many it’s confusing, while for others it’s even terrifying…I've started a Chat thread for you to participate in and discuss your hopes, dreams, worries, and concerns. All subscribers are welcome to join!
The REAL headline everyone (should be) buzzing about:
Substack is officially entering the advertising game!
In our Chat thread, we’re already talking about it:
Yes, native ads — the very thing Substack once swore off (similar to saying Substack will be FREE forever) — are now on the roadmap.
But before you panic, let’s break it down from a marketing and brand management standpoint:
What Exactly Are Native Ads — and Why Should I Care?
Good question. Many might be asking this.
Native ads aren’t annoying banner ads or irrelevant pop-ups.
Instead, they’re seamless, in-feed sponsorships that blend naturally into the reader's experience.
When I was working for the CommsMarketing agency Edelman in my twenties, native ads were hot and new, generating millions of views for our clients.
Why?
Because they aren’t so easy to spot.
This is an example from Germany’s top-tier media, BILD:
No one would think this story about amateur sports would be paid content! BILD incorporated it into their look and feel.
The featured image aligns perfectly with the online presence, and the texts and headlines could also have been written by a reporter from BILD (and this is often the case).
What Does This Mean for Substack?
Think ads that look and feel like part of your content, but clearly labeled and often creator-approved:
A brand sponsor highlighted at the top of the Substack Notes feed
A sponsored post in the Staff Picks section on the Explore page
Tailored offers that match the theme of your newsletter so you’ll share a …
A “Brought to you by…” note in your newsletter (you can manage)
… in your podcast episode
… (many more examples we’ll talk about in the following newsletter)
And here’s what we (me and the experts I’m talking with) think:
Substack won’t just allow native ads; they’ll likely help creators manage and place them.
Mike Kerns from The Chernin Group (the guy leading the round) said it straight in a New York Times story:
“We think it is a massive opportunity to launch a native form of advertising within the Substack ecosystem at some point.”
And you better believe that “some point” is coming fast.
Finnegan Told Us MONTHS Ago!
If you’ve been riding with The Online Writing Club, you already knew this was coming.
That’s because
(or Mr. Anonymous, as I call him), one of our most trusted insiders, dropped this exact bombshell in one of my interviews and our members-only sessions months ago.Besides being an ad executive, father, and writer, he used to be a political appointee under President Bush, known for his bluntness and experience in Republican politics. He has testified before Congress, briefed Presidents, and met with top officials—including foreign leaders and intelligence officers. Though he stayed out of the spotlight, he worked behind the scenes in high-security settings like the White House Situation Room, the Pentagon’s “Tank,” and ultra-sensitive Gang of Eight briefings.
He said the move to native ads was inevitable. He predicted brands would want in once Substack Notes and the app started to take off. And he explained how writers like us could benefit from it — if we play it right.
That’s why we recently hit 14,000 subscribers.
Because people trust The Online Writing Club to not only break the news, but also add context, insight, and a game plan.
🎧 Wanna Hear It from the Source?
Finnegan didn’t just whisper the truth. He sat down with me for a deep-dive podcast episode and special class that covers it all:
How native ads might work on Substack
Who they’re good for (and who they’re not)
And how writers can prepare to benefit instead of panic
👉 Listen to our podcast together here (7,000! podcast downloads so far!)
👉 Watch the YouTube breakdown here
👉 Watch our deep-dive masterclass today.
I’m releasing an exclusive replay of our most recent Strategy Circle with Finnegan, and when I say it’s jam-packed with real strategy and future predictions, I mean it.
In this private session, we dug into:
Substack’s app evolution
The truth about native ads and monetization
What writers should be doing now (even before the ads go live)
And yep…Finnegan is an annual member of the Club. Because even insiders want to stay ahead of other insiders 😉
It’s My Daughter’s Birthday Weekend!
I’m in full celebration mode 🥳
So to share the love, you can join The Online Writing Club with 20% OFF an annual membership — just this weekend.
Because whether you’re trying to stay ahead of platform changes, get in on the ad conversation early, or just build your audience with heart… this community gets it.
Also, you’ll get access to the Substack Course for beginners!
If this story made you whisper “DANG”…
