A few weeks ago, Erika Veurink posted on LinkedIn about a brand partnership on her newsletter, Long Live (thanks Erika for inspiring today’s post!). One line she wrote stuck with me: she called the “thank you” and “more please” comments her unofficial KPI for brand partnerships. I haven’t been able to stop thinking about it. Because she’s absolutely right, and because brands typically aren’t measuring partnerships this way.

For most brands running a paid sponsorship, the scorecard is some mix of clicks, views, product sales, comment rate, ROAS. A few will go a step further and try to measure the feeling: a sentiment score, a tidy ratio of positive to negative. But a number like that compresses a few hundred specific reactions into one figure and throws out the only part you could act on: what people said, and why.

What isn’t being measured is whether anyone was actually glad it existed.

Whether the audience welcomed the brand into a space they’re usually protective of.

Whether the brand’s presence in a space they’re borrowing actually made the content better.

On community platforms built on trust, that’s the whole ballgame, and it shows up in the one place the analytics often overlook: the replies.

And right now there’s a lot to look at. In the last few weeks I’ve watched several writers run stellar brand partnerships that felt so well integrated into their typical content and style: Erika’s with Poshmark, Rose Florence Anderson with Merit, and Lena Dunham with The RealReal.

Part of why this works on Substack is that the platform built the tools for it: things like the co-author byline, brand-run publications, the guest-post mechanic. Partnerships here don’t necessarily mean a banner bolted onto someone’s essay. Rather, the brand can show up inside the work.

So, let’s evaluate what great partnerships look like on Substack. What makes readers stay and comment, not just scroll past.

Three partnerships, three different answers.

Consistency

Starting with the one that inspired today’s post! Erika’s post was a guide to five under-the-radar brands worth hunting secondhand, with the kind of detail you only have if you’ve actually done the hunting: which styles to search, how to spot a real Brooks Brothers Golden Fleece tag, what a fair price looks like. It disclosed Poshmark right at the top.

While sponsored, the post was essentially indistinguishable from what she already does. She does a deep dive on five brands she shops for on Poshmark with curated selections of each. She’s been on Poshmark for fourteen years and linking secondhand finds on Long Live for five. Poshmark didn’t ask her to change her behavior; it paid to resource a behavior she already naturally does. The comments speak for themselves: actual questions, users sharing their own Poshmark gems, and asking for more resources like this post.

This resonated with her audience because it wasn’t new. She’s been doing this type of post organically for years. The brand affinity with Poshmark far pre-existed the post, and readers could feel it.

And here’s the tell that this is a strategy, not a fluke: Poshmark is running the same play elsewhere. This week, Jennifer Cook of Mom Friend, a 7k-subscriber newsletter, published “steal my poshmark likes,” a tour of the pieces she’s currently eyeing on the app, sponsored by Poshmark and disclosed up top. It’s the same model: a writer who’d be on Poshmark either way, paid to do it out loud. And the comments did the same work: “Obsessed with Poshmark. Obsessed with this post,” one reader wrote, which is about as clean a version of this whole idea as exists: gratitude for the brand and the piece in the same breath.

The lesson for a brand is almost too simple, and it scales: find the writers already, unpaid, doing the thing you’d want to pay for… then get out of their way. Poshmark didn’t manufacture the affinity in either case. It found people for whom it was already true and resourced it. You can’t buy your way to that kind of authenticity.

Contribution

Rose Florence Anderson (brand director at Alex Mill) runs The Rose Period, which tells special and unexpected stories from the art world. She recently partnered with Merit to create one of my favorite partnerships as of late.

“The History of Pink” was a real art-history story. She details how pink traveled from the color of kings to the color of girls, traced across five centuries of pigment, from a Bosch to the shade Madame de Pompadour commissioned to engineer her own image to Schiaparelli’s shocking pink. She weaves in guest curators’ favorite pink moments, tapping writers like Joanna Goddard, Kelly Klein, and Somsack Sikhounmuong.

There is no mention of Merit or product throughout most of the piece, until you reach the end. The piece includes an interview with Merit’s director of color about why pink is such a tricky color to get just right. A few of Rose’s favorite products are listed at the bottom. The brand’s expertise in color is part of the payoff. You finish the piece having learned something, and some of what you know actually came from the sponsor’s inclusion.

The engagement on this piece alone tells a story of success: 100 restacks, over 480 hearts, over 90 comments and growing... This one resonated because of genuine brand contribution.

The lesson: don’t ask what your brand wants to say. Ask what your brand actually knows that readers would want to learn.

Scarcity

Lastly, we have Lena Dunham’s post for The RealReal, which opened in an unusual way: not with the brand, but with a list of all the deals she's said no to. The glittery vibrator she couldn't bring herself to push for Mother's Day. The endometriosis product she agonized over, only to lose the gig to a well-lotioned actress ten years younger. She's never done a brand collaboration, she tells you, because she physically cannot pretend. And then, she states that The RealReal was the fastest yes of her life.

That opening is the whole move. The resale obsession is genuine and documented; she gets into early-menopausal weight gain, the failures of extended sizing, and how vintage hunting gave her back the gift of dressing. But what makes the endorsement land isn't only that it's true, it's that she's spent the first half of the post proving how rarely she means it. The disclosure comes only after she's earned it, by which point you already believe her.

And the comments answer in kind. Nobody pushes back on the ad; they get nostalgic. One reader saw “Unique Thrift” and said Lena had evoked a core memory, Cleveland thrifting, decades ago. That’s what a welcomed partnership produces: not “nice ad,” but readers wandering off into their own stories, the brand as connective tissue in the background.

Her nos are what make this yes mean something. The lesson applies to the writer as much as the brand: the value of your yes is set by the credibility of your no. Protect it, and a partnership becomes something readers trust instead of something they scroll past.

What the three have in common

Three different approaches, and a few learnings.

All three disclosed the partnership clearly and upfront. None of these posts hid what they were, and readers were warm anyway. The notion that readers inherently hate ads is an outdated one. Users hate ads that feel like ads, not ones that actually add something to their experience.

Rose’s Merit disclosure

Two of the three made the brand’s people into sources, with Merit’s director of color and The RealReal’s chief brand officer. The brand stopped being a logo and became a character with something to say, which is a far more interesting thing to read than a tagline. It also humanizes the brand, which makes it a harder thing to resent.

And all three pass a single test you can apply before anything ships: would this be worth reading with the logo removed? Strip Poshmark out of Erika’s guide and you still have a useful secondhand-shopping piece. Strip Merit out of Rose’s and you still have an essay about pink worth your time. Strip The RealReal out of Lena’s and you still have a funny, true account of getting dressed at forty. The sponsorship is purely additive. That’s the difference between a partnership readers genuinely value and one they tolerate.

The metric was never hidden

Comments are the real KPI. They are the one place the audience tells you, in their own words and before any sales data shows up, how your brand was actually received. Reach tells you how many saw it. Clicks tell you how many acted. The replies tell you whether you’ll be welcomed back.

And that order is the whole point. The reception comes first, whether the audience was glad you showed up. The thing brands actually want to generate (sales) comes after, because they planted the seeds earlier on. A brand watching only its dashboard sees the result and misses the reason.

Which flips the usual question. Most brands walk into a partnership asking some version of what will this do for us. The writers seeing success here are asking something else: would the audience be glad we showed up. Get that right and the numbers follow.

None of this is new, it's just easy to overlook. Brands are still working out how to judge Substack as a channel, and the instinct is to reach for the numbers they already trust. But the most useful read is sitting in plain sight: are readers glad you're here? Erika, Rose, and Lena got there three different ways: showing up consistently, teaching readers something real, saying no often enough that a yes carries weight.

The proof was the same in all three. It's under the post in the replies, where someone you didn't pay decided to say, more please.

For a long time, brands wouldn’t even consider touching Reddit organically. It was too rough, too hostile to brands, too unknown. They’d stick to paid ads with comments off and leave it at that.

Well, things have evolved. Brands have found that Redditors are not, in fact, purely hostile to brand activity on the platform. Some have started dipping a toe into what it means to build an organic presence on a platform rooted in community.

The most common piece of advice brand teams get about Reddit is some version of “join the conversation.” Engage authentically. Show up in the spaces where your audience already is. Build relationships over time. Be part of the community.

The advice isn’t wrong, but it’s oversimplified. It’s been hollowed out by years of being applied to platforms that don’t actually have real conversations to join. On Instagram, on TikTok, on LinkedIn, “join the conversation” mostly means posting content into a feed and seeing what the comments do. That’s not a conversation. That’s a one-way broadcast into a void.

Reddit isn’t built that way. Subreddits are real communities — they have histories, internal rules, established voices, inside jokes that took years to develop, norms a brand has to learn before it can contribute. A brand showing up to “join the conversation” on Reddit isn’t simply stepping into a comment thread. It’s more like stepping into someone else’s home. The people in it know each other. The norms are respected and enforced by who gets upvoted and who gets ignored.

Most brand teams don’t actually take the advice at face value anymore. They know Reddit isn’t Instagram. The problem is that they don’t know what the alternative looks like, and not knowing translates into hesitation. Show up too brand-forward and the community will see through it. Show up too casually and the community will mock you. So most brand teams don’t show up at all, and miss a real opportunity to connect with their audience.

The brands that get this right have figured out something simple: “join the conversation” is a useful starting point but a terrible endpoint. The real work is figuring out what joining actually looks like for your specific brand. Across the brands I’ve seen do this well, there are four distinct ways of showing up:

1. Sustained presence through a named human: a real employee who shows up in their own voice, in communities where customers already are. (Sonos)

2. A brand-owned community: building and operating a subreddit as the brand’s own customer service and community infrastructure. (Fidelity)

3. Founder-led engagement: small-brand presence anchored by the actual founder, listening and responding directly. (No Reception Club)

4. Content-driven helpfulness: showing up in conversations where the brand can offer category expertise, with traffic as a downstream effect. (Wayfair)

Sonos: showing up as a person, sustained over time.

If you spend any time in r/sonos or adjacent audio communities, you’ve probably encountered Keith. His handle is u/KeithFromSonos. He answers product questions, walks people through troubleshooting, explains how features work, occasionally apologizes when Sonos has gotten something wrong. He does this consistently, in his own voice, over years.

Keith isn’t pretending to be a community member. His handle says exactly who he is. He’s a Sonos employee whose job is to show up in the communities where Sonos customers actually live. He’s just there, regularly, doing the work of being helpful in public.

Keith answering user questions during Sonos's most recent Spring Office Hours on r/sonos

Why it works: the named-human framing does something the institutional brand account can’t. A reader watching Keith answer a question isn’t watching “Sonos Support” do a routine task. They’re watching a specific person who happens to work at Sonos help someone solve a problem. The accountability is concrete and over time, users start to trust him.

That trust then attaches to Sonos, but it does so indirectly. The brand earns credibility through the person, sustained over time with a lot of consistency.

What makes Keith work are three conditions:

1. A real human with real expertise, not a social media generalist. Redditors can spot the difference within a few replies.

2. Sustained presence. Trust on Reddit accrues at the pace the community decides, which is often slow.

3. A service mindset, not a marketing one. Keith isn’t there to message the brand. He’s there to help people, and the brand benefit is the downstream effect.

Most brands aren’t set up for this. The work requires real internal commitment: actual people, with actual subject expertise, given actual time to be present in communities the brand cares about. It’s a specific function that many brand teams can’t or won’t fund. The ones that do get something hard to compete against, because that kind of trust takes years to build.

Fidelity: building the community itself.

Most brands trying to figure out organic Reddit presence start by asking which existing communities to participate in. Fidelity went a step further and built their own. r/fidelityinvestments is a brand-owned subreddit launched in 2021, with over 243,000 members and thousands of customer questions answered by real Fidelity representatives. Fidelity was one of the first major brands to take this approach.

The approach is different from Sonos’s. Where Keith shows up as a single named human in communities the audience already inhabits, Fidelity created the room. r/fidelityinvestments is positioned in the community description as “the official sub for Fidelity—and an investing community that’s all about helping each other out.” It runs pinned monthly investing discussion threads, posts regulatory updates that affect Fidelity customers, announces feature changes, and answers individual customer questions in public. Community work at this scale suggests a real team is behind it, with serious budget and infrastructure.

Why it works: Fidelity recognized something many brands haven’t — that for a category as question-heavy as investing, a brand-owned subreddit can function as a customer service channel that doubles as community infrastructure. Customers get answers from actual Fidelity representatives in a place where other customers can see them. Fidelity gets a searchable record of expertise that compounds over time. New investors join because there’s already an active base, and the active base keeps coming back because their questions get answered.

The three conditions that make Keith from Sonos work apply here too, at larger scale: 1. real expertise, 2. sustained presence, 3. service mindset. What Fidelity adds is infrastructure. They’ve treated their Reddit presence as an ongoing channel to build and operate, and their commitment to that shows through to their audience.

The tradeoff is real. A brand-owned subreddit requires sustained internal resourcing (staff, training, content cadence, moderation) that most brands aren’t structured to commit. But for brands in categories where customers ask a lot of questions and expertise is the product, this is the most impactful version of organic Reddit presence. And once built, it’s the hardest for competitors to replicate.

A few other community engagement models worth knowing about:

No Reception Club is an indie travel goods brand that makes organized travel bags for parents traveling with kids. Its Reddit account is run by one of the co-founders, something you don’t often see.

She uses Reddit Pro, a free tool for surfacing relevant conversations across the platform, to find the discussions worth showing up for. Then she engages directly: answering questions, hearing how customers use the product, taking in their feedback. Reddit Pro is what makes this kind of listening actionable, regardless of team size. The conversations are out there and the tool is what makes them findable. What still surprises me is how few brands are actually using it.

Why it works: most brands have layers between the people running the company and the customer voice. The cost of that distance is feedback becomes a game of telephone. No Reception Club’s setup is the opposite: messy feedback, in real time, read directly by the person who can act on it. The brand gets a signal most brands its size couldn’t afford to commission. The community gets the increasingly rare experience of talking to a brand and having an actual founder read what they wrote.

Wayfair started showing up organically on Reddit because their content team noticed something interesting happening in Google: Reddit conversations were appearing on page one of search results for home searches. Their potential customers were finding answers on Reddit instead of on Wayfair’s properties. Reddit had become a discovery channel they couldn’t afford to ignore.

The response wasn’t a campaign. The team used Reddit Pro to find conversations in subreddits where Wayfair could be useful (interior decorating, home advice, and living-space communities) and started showing up with genuine product-research advice. Things like, how to evaluate furniture quality, what to measure before buying a sofa, how to think about reviews and ratings. When relevant and a natural fit, they link to Wayfair’s existing blog.

Why it works: the mode is content marketing, but the posture is helpfulness first. The team has operationalized the work by showing up consistently, so the trust the brand builds compounds. Over time, the community starts treating the brand as someone they can come to for more than just product questions. This is the approach most brand teams could probably adopt, especially given Reddit’s place in the SEO/AEO conversation.

If your brand wants to be on Reddit and you don’t yet know which approach fits, here’s what I usually suggest brand teams do first:

Start with listening, not posting. Before deciding how to show up, understand the landscape. What conversations are already happening in the communities relevant to your brand? What questions come up? What frustrations? What kinds of contributions does the community already value? Reddit Pro is a free tool that makes this kind of listening possible without manually browsing hundreds of subreddits. It’s the first thing I recommend brand teams look at when they ask me where to start.

Pick an approach that fits your goal. There are a multitude of ways to show up as a brand on Reddit. Decide what your brand is actually trying to accomplish and pick the approach that matches. Trying to do everything at once is what leads to the hedged, generic presence the community ignores.

Show up as a brand, clearly. No disguised accounts. No attempts to look like a regular community member. The brand’s identity should be obvious in the handle, the content, and the disclosure. Every brand in this piece has done this. The clarity is what makes the rest of the work resonate.

Stay in your lane. Show up in communities where your brand can offer something genuinely useful. The relevance has to be real, not stretched.

Commit to the community’s timeline, not the brand’s. Trust on Reddit accrues at the community’s pace. An organic play on Reddit is betting on the long game. If you’re willing to invest in years of presence in communities your brand cares about, the trust will follow.

This is the third of five posts on patterns I keep seeing in how brands approach Reddit. Here are the first two:

The next post is on why most brands still underestimate Reddit’s real impact and the case to make internally for taking it seriously. Subscribe if you want it in your inbox.

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Many brand AMAs I’ve watched underperform share a single design flaw. A spokesperson who isn’t actually willing to answer questions, paired with a comms team that wants to control the message. The community can usually tell within three responses what’s happening. Downvotes follow. The brand walks away with a story about how Reddit is a hostile platform.

Reddit isn’t hostile to AMAs. Reddit is hostile to inauthenticity.

The format was literally built for substance: long-form, public, accountable answers to whatever the community wants to ask. When a brand uses it as a media moment to be controlled, the community recognizes the misfit right away. When a brand uses it for genuine engagement, two-way conversation, and feedback, the format does something almost no other channel can: it generates trust at scale, in real time, in front of an audience that pays attention.

The clearest example of this I have is one I worked on six years ago.

In April 2020, six weeks into the COVID lockdown, with markets down roughly 20% from their February peak and retail investors panicking, Charles Schwab ran a promoted AMA with Carrie Schwab-Pomerantz. She’s a CFP, the president of Charles Schwab Foundation at the time, the founder’s daughter, and a financial educator who’d spent decades doing the public-facing version of the work. Most financial services brands at that moment were doing the opposite of an open Q&A: locking down spokespeople, routing every statement through legal, going into defensive crouches. Schwab went the other direction.

A few things about how it was set up mattered.

She didn’t open as a corporate spokesperson. The first line of the AMA was a personal story about why financial literacy mattered to her: her father starting Schwab in 1973 to give people access and knowledge, her own life building on that mission. By the time she got to “in the middle of a crisis like COVID-19 there seem to be more questions than answers,” she’d already established who she was and why she was there.

She named her constraints honestly. The post included a short list of what she couldn’t discuss, such as specific stock recommendations and individual account questions. Most brand teams would have hidden these in a footer or skipped them entirely. The Schwab AMA led with them. On Reddit, transparency about constraints reads as honesty; obscuring them reads as evasion.

And the questions she got were real. Not gotcha questions, not troll questions, but actual financial-anxiety questions from people who needed help during a very stressful time.

“I have money sitting in a low-interest savings account I’ve been planning to invest. Is this the time?”

“How should I pay back my student loans?”

These were the questions of a community in a crisis, asked of someone they’d decided they could trust. The harder ones came too. One user asked her: “How do you work around the fact you are just telling people to ration the little they are given? You were born into wealth, does that affect your thinking?”

The brand didn’t delete the question, and on a promoted AMA, they could have. Promoted AMAs give brands moderation tools that community AMAs don’t: the team can choose which comments get approved, which subreddits the AMA targets, and how visible certain pieces of the conversation become. Schwab had those tools. They chose to let the question stand.

And the answer engaged the premise head-on rather than dodging it. Carrie corrected the assumption directly — she wasn’t born into wealth. Her father was a struggling businessman through her childhood and her parents divorced when she was nine. She then connected that history to why financial education had become her life’s work. She didn’t scold the asker for the assumption; she acknowledged it was a common one. The question earned a handful of upvotes. Her answer earned far more — a small reminder that on Reddit, the substance often lives in the replies, not the original post.

The thread closed with 755 comments and a sign-off pointing readers to free Schwab educational resources. The brand’s role had been to make expertise accessible, not to sell anything specific. The community thanked her back.

What made it work wasn’t a clever campaign. It was three conditions, all met:

A principal who was genuinely interesting and substantively expert. Carrie wasn’t reading from a script. She was a domain expert engaging with strangers’ real financial questions in her own voice. Reddit can spot a media-trained spokesperson within two answers, and a media-trained spokesperson can’t carry an AMA for two hours.

A willingness to engage the hard questions. The AMA didn’t moderate away the pushback or duck the difficult framings. The “you were born into wealth” question is the one many brand teams would have steered around or asked Reddit to remove. Letting it stand, and answering it honestly, is what turned a corporate Q&A into something the community actually trusted.

A structure that prioritized transparency over polish. Disclosed constraints up front. Clearly promoted. Real names. Real timeline. No attempt to make the post look like anything other than what it was. The polish brands typically bring to public-facing content is the thing Reddit punishes most.

Without any one of those, the AMA would have collapsed the way most do: with downvotes, disengagement, and a brand team telling itself Reddit was the problem. With all three, it became one of the most effective single pieces of brand work I’ve seen on the platform. Especially because it happened in a regulated category, during a crisis, with senior executive risk on the line. Most brands in that moment couldn’t bring themselves to do an open Q&A about retirement planning during a market crash. Schwab did. They leaned in and the community leaned in right back: by showing up, asking real questions, and engaging in good faith.

One thing worth surfacing here, since it comes up almost every time I work with a brand on an AMA: promoted AMAs give brand teams moderation controls, and the question of how to use them is real.

Most teams hear “moderation” and default to “moderate broadly to stay safe.” That’s almost always the wrong instinct. The point of moderation isn’t to remove anything difficult. It’s to remove noise. Spam, off-topic posts, bot replies, and content that violates Reddit’s own rules are fair to remove. Meaningful critique of the brand isn’t. If a community member is asking a hard question in good faith, that question is feedback, and removing it downgrades the authenticity of the AMA (and by default, the brand hosting it).

The principle worth holding is simple: moderate for noise, not for difficulty. Spam doesn’t deserve a place in the thread. Real questions, even (and especially) uncomfortable ones, absolutely do.

The reason most brand AMAs fail is that brand teams arrive with the wrong format in mind. They’ve sat through media training. They’ve watched executives field questions from journalists in controlled settings. They assume AMA is just another version of that work, a moderated Q&A with the brand in charge of the narrative.

AMAs are the inverse of a press junket and require vulnerability, authenticity, and a genuine openness to have a two-way conversation. Brands who want to succeed here have to give the community control over what gets asked. The way the brand responds to those questions is what makes the difference.

Here’s what I suggest brand teams think about when considering an AMA:

Is the spokesperson actually interested in answering questions, or interested in being seen answering questions? Those are different things, and the community can tell.

Does the spokesperson know the subject matter well enough to engage a question they didn’t see coming? If the answer is no, the AMA will collapse the moment the easy questions run out.

Is the team willing to let the hard questions stay up and get answered? If the plan is to have moderators remove anything difficult, the community will notice and the AMA will lose credibility halfway through.

Are there real constraints on what the spokesperson can discuss, and is the team willing to name those up front? Every brand has constraints. The question is whether you disclose them or hide them.

If the answers to those questions aren’t yes, the AMA won’t succeed no matter how good the talking points are.

This is the second of five posts on patterns I keep seeing in how brands approach Reddit. Including the first below:

The Messy Middle

Brands Have Decided Reddit Matters. The Creative Hasn't Caught Up.

Disclosure: I’ve been in brand partnerships at Reddit for the past 9 years. The views in this piece are my own and don’t represent the company…

Read more

2 months ago · 8 likes · 6 comments · Alex

The next post is on why "join the conversation" (the most common advice brand teams get about Reddit) is the wrong instinct, and what showing up as a brand actually looks like instead. Subscribe if you want it in your inbox.

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Five years ago, when I told marketing teams that Reddit needed to be on their media plan, they would do one of two things: laugh in my face, or ignore me completely. I spent the better part of a decade making that pitch to brand teams who had decided, without much examination, that Reddit was a place where their brand didn’t belong and their customers didn’t live. The rejections were reflexive, usually arriving before I’d even finished the pitch.

As the years have passed, the conversation has shifted. The marketers who laughed five years ago have read the latest Q1 numbers, seen the AI search distribution arguments, watched their competitors quietly scale on the platform, and concluded (correctly) that Reddit is now a serious part of the media plan. The strategic question is settled. The tactical one isn’t.

What I see now, in the work that crosses my desk, is brand teams who know they need to be on Reddit and have no idea how to show up. The most common version of this is a Reddit ad buy built from a copy-paste of their Instagram creative, with a few tweaks: a slightly more casual headline, maybe a few relevant subreddits added to the targeting, and an assumption that the rest will translate. It doesn’t. The campaigns underperform, the budget moves elsewhere, and the team concludes that Reddit Ads is the problem.

Just yesterday, a client asked me for opportunities on an upcoming full-funnel product launch. She walked me through targeting, formats, and budget — every input except creative. I often find creative is the line item that doesn’t quite make it onto the planning doc, the part of the campaign that gets inherited from the cross-platform brief rather than built specifically for the platform it’s about to run on.

It’s not that brands don’t care about creative on Reddit. It’s that Reddit feels harder to figure out than other platforms, and that difficulty translates into de-prioritization. The audience has a reputation for being unrelenting. The playbook from Instagram or TikTok doesn’t transfer cleanly. The forms and language are unfamiliar enough that knowing where to start isn’t obvious. Targeting is a knowable input. Format is a dropdown. Budget is a number. Creative is the part where the platform asks something genuinely new of the team, and often that challenge leads to… nothing.

The brands winning on Reddit’s paid side aren’t running better versions of their cross-platform ads. They’re running ads built in the shapes Redditors use to share information, in the language Redditors use to talk to each other. That difference is what separates the work that lands from the work that doesn’t.

The brands that run paid Reddit advertising well understand something most brand teams don’t: Redditors have their own native ways of communicating, and you can borrow them. There’s the form: the Megathread, the guide, the TL;DR, the multi-section breakdown, the upvote-as-poll, the discussion prompt. And there’s the language: the acronyms (ELI5, TIL, AITA), the syntax (r/ for subreddits, u/ for users), the specific constructions Redditors use (”if OP knew,” “Hear us out,” “walked so X could run”), the inside jokes, the cadence of how Redditors actually talk. Both matter. Brands that learn the forms and speak the language get treated as participants in the platform’s vernacular. Brands that ship the same content they ran on Instagram get treated as exactly what they are: visitors.

A few examples worth studying. Each one demonstrates a different principle, but the underlying move is the same: pick a shape Redditors recognize, build the message inside it.

Nike ran a Megapost framed as a guide — tagged [GUIDE] in the title, structured as a multi-section breakdown of women’s training products. Each product was credited to a specific subreddit: the Swoosh Bra to r/ABraThatFits, the Universa Leggings as “the unofficial leggings of r/movementculture,” the Free Metcon 5 to r/formcheck. The headline argued for a broader definition of sport: “From r/meditation to r/strength_training and r/mindfulness to r/trailrunning, sport is movement for every moment.”

Why it works: the subreddit-namechecks aren’t ornamental. They’re acts of crediting. Instead of telling the community “our product is for you,” Nike handed them the framing — these are your communities, and we built this thinking about you. That’s a small power inversion no amount of polish can buy. The product copy is conventional; the Reddit fluency is in who Nike credits.

Google ran a TL;DR post for switching to Android: “Whatever device you’re switching to…It’s all good with Google on Android,” followed by six features in scannable sections, each opening with “It’s all good with…” The closing line winked at the format itself: “When you make the switch, you’ve got nothing to worry about, especially if you read all that.”

Why it works: most ads pretend the reader chose to engage with them. Google’s ad admits the reader put in work (reading a long-form promoted post is effort) and rewards them for it. That recognition is what most brand creative is structurally incapable of. The post earned over 4,000 upvotes, a number nearly unheard of for a promoted brand placement, because the closing line told readers they’d been seen.

Wendy’s ran a one-line gag: “Are Wendy’s Saucy Nuggs real? Upvote your answer in the comments below!” — then the brand itself replied with one-word answers (”Nuggs aren’t real in general,” “Perchance,” “Yes,” “No”), each racking up hundreds to thousands of upvotes.

Why it works: the brand is doing the bit on the audience’s behalf. The audience gets to participate in a low-lift way (a single upvote) and then enjoy the performance — like watching a comic riff on themselves. The “Perchance” reply is the proof of attention: a 2021 Reddit micro-meme that became shorthand for clipped, knowing brevity. A brand using it correctly demonstrates that it was paying attention to Reddit long before this ad ran, and Reddit notices when a brand has done its homework.

Discover used the TL;DR form at headline scale: “TL;DR Cashback Debit gives you more than just cash back.” The body opened with “Hiya Redditors, If you’re reading this, we’re here to say one thing: it’s time to start earning cash back. OK, there’s more. Hear us out…”

Why it works: Discover doesn’t become unhinged or meme-y or casual. It just sounds like a Redditor who happens to work in financial services. That’s translation rather than abandonment. Most brands attempting Reddit fluency assume the goal is to sound like a different brand than they are. Discover’s move is the opposite: stay Discover, but speak Reddit’s cadence while doing so. That’s the version of this work available to nearly any brand, including those who lean more cautious.

New Balance ran a discussion prompt: “Casual chic to streetwear to sporty.. whatever your personal style is, how would you layer in the New Balance 550, 574, or 9060s? Spill in the comments below!” The comments filled with actual Redditors describing how they style each model (”Love my NBs!! Only have the 9060s though. I style them with joggers when I’m out running errands…”).

Why it works: most ads are monologues; this one is an invitation. New Balance stepped back and trusted the community to do the selling. The comments aren’t a side effect of the ad, they are the ad. The brand made room for users to talk about which model fit which life, and the resulting thread is a more credible product testimonial than anything the marketing team could have written. Anyone who spends time on Reddit knows that often the best content is in the comments section- and this can be true with ads as well.

Neutrogena did the most ambitious version. The ad is structured as a reply to a fictional Reddit thread: a mocked-up post in r/theoriginalwatercream asks “Is anyone else realizing Neutrogena Hydro Boost Water Cream walked so all these other Hyaluronic Acid creams could run?” — and the Neutrogena reply is “If OP knew about Hydro Boost Water Cream+ and its 72-hr hydration, they’d be thriving. Just saying.”

Why it works: the ad is funny because it knows what it’s referencing. The ad demonstrates that the brand understands Reddit well enough to make affectionate jokes about it. That’s the highest form of platform fluency, and it’s also the riskiest: get it wrong and you’re cringe, get it right and you’re a meme. Neutrogena got it right.

So what does Reddit-native creative actually look like? Here’s what I tell brand teams when they ask:

Lead with a form Redditors recognize. Pick a native form before you pick a message. The guide. The TL;DR. The comparison. The how-to. The Megapost. The upvote-as-poll. The discussion prompt. Each of these has a specific shape Redditors will recognize from their own use of the platform, and each one signals “I know where I am” before the reader has read a single word.

Use the language Redditors actually use. The r/ syntax for subreddits, the u/ syntax for users, the acronyms (ELI5, TIL, AITA, TL;DR), the specific constructions (”if OP knew,” “walked so X could run,” “Hear us out”), the cadence of how Redditors actually write to each other. Polished marketing language reads as foreign in a Reddit ad slot. The vernacular reads as native.

Name the community you’re talking to. Reddit’s geography is its central feature. Reference the subreddits your audience already lives in. Credit the communities whose conversations informed the product or the post. Treat the platform’s communities as participants in the work, not as a targeting layer.

Reward the reader for paying attention. The single best move in Reddit creative is a wink at the reader for having engaged with the post. Google’s “especially if you read all that” closing line is the canonical version. Wendy’s one-word “Perchance” reply is another. The move signals respect for the reader’s time, which is more or less the opposite of how Instagram ads tend to read.

Be willing to look like an ad. The biggest mistake brands make in the other direction is trying to disguise their ads as organic content. Reddit allows promoted posts, marks them as such, and rewards honest creative inside that framing. The goal isn’t to pass as native content. It’s to use the same forms and language native content uses, while being clearly, accountably, a brand.

Match the move to your brand voice. Wendy’s can do “Perchance.” Discover probably can’t, and shouldn’t try. The goal isn’t to make every brand sound like the unhinged-brand-account version of itself. It’s to find the Reddit-native form that fits who the brand already is.

This extra effort is worth it.

This is the first of five posts on patterns I keep seeing in how brands approach Reddit now that the strategic question — should we be here? — has been settled, and the tactical one — how do we actually show up? — hasn’t. I’m starting with paid advertising because it’s the most concrete of the five patterns.

If you've found this useful, two other "On Brand" pieces you might want to read: Participate, Don't Perform (on how brands are showing up on Substack itself) and 9 Things I Learned in 9 Years at Reddit (on what almost a decade at the company taught me about the platform).

The next post is on AMAs: why many brand AMAs fail, why the format itself isn’t the problem, and what one financial services brand did in the early weeks of COVID that almost no other brand in their category was willing to do. Subscribe if you want it in your inbox next week.

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Last week, Starbucks rolled out a new feature in their app: a ChatGPT integration that helps you decide what to order. (thank you for highlighting this!). You can literally ask AI what you should drink today, and it’ll suggest something based on your mood, the weather, whatever. It’s slick. It’s well-designed. And my immediate reaction was: who asked for this?

I don’t say that to be snarky. But really, who wants this? Is this really what coffee drinkers are asking for?

I spent nearly a decade at Reddit working in brand partnerships, and that entire time, I watched brands try to figure out how to show up on the internet in a way that felt authentic. Some of them nailed it. Many of them didn’t. And the ones that didn’t almost always had the same problem: they were solving for a boardroom question, not a human one.

“We need an AI play.” “We need a Reddit strategy.” “We need to be on Substack.” The impulse is always the same. There’s a new shiny thing and everyone rushes to show up there. And it almost always leads to the same result: something that looks right on a slide deck but feels hollow when it reaches an actual person.

What’s always shocked me is what’s missing from these decisions. It seems so obvious: listen to your customers. Hear what they’re actually saying. What are they asking for? What are they frustrated about? I highly doubt Starbucks customers were out there struggling to pick a coffee.

I think about this constantly now, because I’m no longer just the person in the room advising brands on how to show up. I’m also the one trying to show up myself.

What Reddit taught me

I joined Reddit in the early days, when the platform looked a bit like a dystopian Craigslist, had no mobile app, and was on many brand and agency “black lists.” I stayed through massive growth, a lot of change, and an eventual IPO. Nearly a decade on a platform that is, at its core, allergic to anything that smells like marketing. Reddit users can spot inauthenticity faster than any focus group ever could. They’ll call it out, downvote it, and worst case, roast it in the comments before your campaign even finishes loading.

That environment teaches you something that most marketing careers don’t: you cannot manufacture trust. You have to earn it.

The brands that actually worked on Reddit weren’t necessarily the ones with the biggest budgets or the flashiest creative. They were the ones that understood a really simple thing: Reddit is not a social media platform. It’s a community platform. And that distinction changes everything.

The brands that won were the ones who listened. They paid attention to where their customers spent time on the platform. Saw the questions their audience was asking and answered them. Offered solutions where they could. They were adding value to conversations that were already happening, not trying to start new ones on their terms. They followed the rules and respected platform norms. They showed up consistently, not just when they had something to sell. They earned their presence over time, and in turn, the community respected them.

One of my favorite examples of this happened last year. In r/KitchenConfidential, a community of over 2 million food-service professionals and home cooks, a user started posting daily photos of his chive-chopping progress. Just a guy trying to get his knife skills right, posting every day, asking for feedback. The community loved it. They started analyzing his cuts, giving him tips, making puns. They gave him a nickname: Chivelord. It became a whole thing. The Today Show, The Washington Post, Food Network all picked it up.

Philadelphia Cream Cheese saw it happening. And instead of jumping in with a splashy campaign or trying to own the moment, they did something really simple. They ran one ad for their chive cream cheese. The copy read: “Some heroes chop chives every day until Reddit says they’re perfect. We whip ours into cream cheese.” That’s it. No meme hijacking, no forced humor, no trying too hard. Just a quiet nod that said: we see this, and we think it’s cool too.

The Ad from Philadelphia Cream Cheese

Users loved it so much they screenshotted the ad and shared it in the subreddit themselves. Nearly two months later, Chivelord was still at it, chopping chives. The marketing team at Philadelphia Cream Cheese took note and privately reached out to Chivelord and sent him a care package: a professional knife set, a personalized cutting board, an apron, and of course, chive cream cheese. No strings attached. No ask to post about it. He posted about it anyway, because it felt genuine. The community’s response was overwhelmingly positive. Redditors not only congratulated Chivelord on the gift package, but they also gave credit to the brand for getting involved in a way that successfully added to the moment while respecting the community's culture. Everyone wins.

The care package for “Chivelord”

That’s the whole playbook, honestly. Philadelphia chose authentic participation over promotion. They didn’t try to control the community, they just leaned in. They recognized something real that was already happening, added to it in a way that felt generous, and then stepped back. That restraint is often the hardest thing for brands to learn, and it’s the thing that earns the most trust.

What I saw, over and over again, is that the question brands should be asking isn’t “how do we market on this platform?” It’s “how do we become a useful part of the communities our customers already trust?” Those sound similar. They are not.

The same thing is happening on Substack

I’ve been on Substack actively writing for about a month now (and years as a reader), building this newsletter from scratch. And I’m watching a very similar dynamic play out in a new place.

Substack looks like a newsletter platform. But really, it’s not. It’s a community platform, centered on writing. The newsletters are the main content, but Notes, comments, restacks, recommendations... that’s where the community lives. And just like Reddit, the brands that understand the difference will be the ones users gravitate towards.

Nanit, the baby monitor company, runs a Substack called “In a Blink.” This week they published a note that was just a list of other writers’ posts that brought them joy. Not their own content. Not product promotion. Just: here are five things we read this week that we loved. That’s it. And it was one of the most effective brand moments I’ve seen on the platform, because it felt generous instead of performative. It’s something you see other writers do, highlighting work they enjoyed reading that week. Nanit is leaning into natural platform behavior, rather than forcing their own brand playbook.

Then there’s Melanie Masarin, the founder of Ghia. She writes a personal Substack called Night Shade that covers fashion, travel, recipes, life. Ghia shows up occasionally, but it’s never the point. Most of her posts are just genuinely interesting and engaging. She’s cool, and you want to read what she has to say. The brand benefits from that, but it’s not leading with the brand. It’s leading with the person. The founder-led Substack model works well, when the founder is interesting, committed, and has something to say.

Which brings me to Ariel Kaye, the founder of Parachute Home, who just launched Second Story View, a newsletter about what comes after building a company. It’s not a brand Substack at all. It’s a founder processing a massive life and identity transition in public, and in doing so, she’s building something that will almost certainly seed whatever comes next for her. That’s not a marketing strategy. That’s just someone being real about where they are (and building her personal brand, in return).

Now think about Starbucks asking ChatGPT to pick your coffee for you. It’s not that the technology is bad. It’s that nobody was asking for it. The difference between the brands getting it right and the ones that aren’t comes down to something pretty simple: are you actually listening, or are you just showing up?

Now I’m the one figuring it out

Here’s the part I didn’t expect. After nine years of sitting in rooms helping brands figure out how to be authentic online, I’m now trying to do it myself. For myself. And it’s so much harder from the inside.

When you’re advising a brand, you can see the patterns more clearly. Lead with value. Show up consistently. Don’t perform. Participate. But when it’s your own thing, when it’s your name and your story and your reputation, all of that clarity gets clouded by the questions that nobody talks about in strategy decks: Am I sharing too much? Is this interesting to anyone besides me? Does this make me look like I don’t have it together?

This feels much murkier to me. I find myself second-guessing a lot, something I rarely do when working with clients. That clarity I’m used to feels harder to come by when I’m writing for myself, building my own brand. I know the playbook. I’ve seen what works. But applying it to yourself is a completely different exercise. There’s no brief, no brand guidelines, no one telling you if you’re on strategy. It’s just you, figuring it out in real time.

What I keep coming back to is that the same rules apply. Even though this is personal, even though it’s mine, the fundamentals don’t change. Show up honestly, add value, earn trust over time. Some weeks that looks like a polished On Brand essay. Some weeks it looks like a Note about my kids’ artwork. This will continue to evolve. It all counts, as long as it’s authentic.

The brands that win online in the long run aren’t the ones perfectly optimizing their “platform strategy” or chasing every new trend. They’re the ones that figured out something simpler: people want to connect with other people. They want to feel something. Not logos. Not campaigns. Not chatbots suggesting your next latte.

After nine years on the inside, I’m finally on the outside, building something that’s mine. And the only strategy I have is the one that always worked: be real, be useful, and keep showing up as yourself.

Welcome back to On Brand, where I track how brands are showing up on Substack as a media channel. What’s working, what’s not, and what it means for writers and brands. I’ve been tracking brand activity across 200 major Substack newsletters spanning tech, finance, lifestyle, fashion, food, wellness, and culture.

If you’ve opened your inbox, your group chat, your Instagram, or frankly just existed on the internet this week, you already know: the Sephora Savings Event is here. April 10-20. Everything is on sale. Rouge gets 20% off. VIB gets 15%. You’ve seen the codes. You’ve seen the hauls. You’ve seen the spreadsheets people made ranking their carts by priority. It’s a whole thing. Frankly, I find it overwhelming.

Let’s see what this looked like on Substack.

The Signal

Last week I wrote about how the Substack advertising ecosystem is dominated by B2B tech and finance. Brex, Vanta, WorkOS, Mercury. That’s still true. But a different kind of brand activity is building on the lifestyle side, and beauty is leading it.

Before I get into the data, a quick distinction that matters for this column: there’s a big difference between a paid sponsorship (where a brand pays a writer directly for a placement) and an affiliate mention (where a writer links to a product and earns a small commission if someone buys). Many writers can sign up for an affiliate program. A paid sponsorship requires a brand to actively seek you out (or you pitch yourself), negotiate a deal, and write a check. The economics are very different.

With that in mind, here’s what the beauty landscape looks like on Substack right now. Sephora is the most active beauty brand on the platform, but even Sephora has only done paid sponsorships in four newsletters: Scratch Pad, The Love List, Downtime, and Work Wife. Many other newsletters feature Sephora through affiliate links, where the writer earns a commission but Sephora didn’t pay for that specific placement. And beyond all of that, at least 40 of the 200 major newsletters I’m tracking mention Sephora organically (reaching approximately 3.8 million subscribers). And that's just the ones I’m following. The real number across the full Substack ecosystem is almost certainly much higher.

One of the biggest beauty retailers in the world is paying four Substack writers. Four. Meanwhile, at least 40 of the largest newsletters are talking about them for free, and that's before you count the hundreds (maybe thousands) of smaller writers doing the same.

Other beauty brands are showing up too. Crown Affair, Ziip, U Beauty, Hanni, Dermstore, Summer Fridays, and Goop are all appearing across multiple newsletters. But the honest read: most of that activity is affiliate links and organic mentions, not paid sponsorships. The writers are doing the work. The brand dollars mostly haven’t followed yet.

That gap is the story. And it tells you something important about what Substack is and what it isn’t. It isn’t a programmatic ad channel where you buy impressions.

It’s a trust network where the organic signal is the real indicator of brand fit.

The Spotlight: Anatomy of a Sephora Savings Event on Substack

This brings me to what happened on this platform. In late March, Sephora started appearing across Substack in a wave of paid placements, affiliate mentions, and organic coverage timed to the Spring Savings Event. Here's how three writers handled it.

Grace Atwood, Scratch Pad (57K subscribers)

Grace is an established influencer with a long-standing Sephora relationship across multiple platforms, so a paid Substack placement was a natural fit. Last October, during the Fall Savings Event, she ran a dedicated sponsored post: “My Guide to the Sephora Savings Event,” a giant edit (for paid subscribers only) broken down by category. 159 likes, 21 comments. The sponsorship disclosure was clean and upfront: “Today’s send is sponsored by Sephora, a store I’ve loved and shopped at forever.”

Which brings us to this April. She published “My Definitive Guide to Shopping the Sephora Sale” as an organic post. She covered it because her readers expect it from her, and it was an incredible, generous resource. That's the best-case scenario for a brand: when the coverage outlives the spend.

Jess Graves, The Love List

Kicking off before the start of the Spring Savings Event on 3/30, Jess ran a paid partnership with Sephora. Her post, “Any City, Any Sephora, Same Routine,” is a masterclass in how to make a sponsorship disappear into your voice. The subtitle: “Not what’s trending, not a gifted alternative, just what works.”

She opens with a travel story about landing in a new city without her luggage and heading straight to Sephora because you can find one anywhere. The whole post is framed as the products that have survived every gifted alternative, every phase where she thought she’d found something better. It reads like a text from a friend, not a sponsored placement. 112 likes, 16 comments. I loved it.

Sabrina Molu, Work Wife (20K subscribers)

This is the smallest newsletter of the three, and the approach is completely different. Sabrina’s post opens with: 'The fashion girlies have Fashion Week, the reality TV girlies have Bachelor premieres, and the beauty girlies? We have the Sephora Savings Event.' That framing tells you everything about how she sees this moment, and her readers clearly agree.

The partnership disclosure is clear, and she adds a mindful spending note. But the core of the post is a reverse makeup method tutorial with product picks that happen to be available in the sale. She includes a poll asking readers if they already have products picked out. It’s interactive, personal, and useful. At 20K subscribers, Sabrina's list isn't massive. But her audience is deeply engaged, and that's what matters. Sephora isn't buying reach here. They're buying trust.

Three writers. Three completely different takes on the same brand moment. One organic post from a writer who previously ran a paid Sephora sponsorship and now covers the sale because her readers expect it (and who is almost certainly earning significant affiliate revenue from every product link in that guide).

Two paid partnerships, each with their own voice, format, and angle. Same brand, same sale, same week. This is what strong brand partnerships look like on Substack. The writers maintain their tone and editorial control. The readers get recommendations that feel native to the newsletter they already trust.

A Quick Note on Monetization Stacking

One detail from Grace’s April Sephora guide is worth pulling out, because it shows how sophisticated newsletter monetization is actually getting. Even though Grace’s April post is organic coverage of the Sephora sale (not a paid Sephora partnership), she still monetized it through a separate sponsored mention from Kate McLeod, a smaller body care brand. And here’s the clever part: the Kate McLeod link drives to Sephora.

Sponsored Mention from Scratch Pad

Think about what’s happening on that single product mention. Kate McLeod is paying Grace for the placement. Grace is almost certainly earning Sephora affiliate commission on any sales through the link. Kate McLeod gets sold through Sephora’s checkout. Sephora gets the transaction, which strengthens Grace’s track record as a converting affiliate, which strengthens her case for future paid Sephora partnerships.

One product mention. Two brands paying her in different ways. That’s the kind of layered monetization that the most experienced newsletter writers are doing, and it’s a reminder that “paid vs organic” is a much fuzzier line than it looks from the outside. The writers who treat every brand mention as a single transaction are leaving money on the table. The ones who think about how mentions stack are building real income.

The Untapped Network

Sephora is paying four newsletters. But the data shows at least 40 other major newsletters mentioning them organically, and some of those numbers are hard to ignore.

Internet Princess by Rayne Fisher-Quann has 145K subscribers and has mentioned Sephora four times organically. Her audience skews Gen Z, deeply engaged, and culturally influential. Zillion Trillion (189K subscribers, 3 mentions) covers consumer culture and money. The Wardrobe Edit (112K subscribers) mentioned Sephora organically on April 10, the day the sale launched. Not paid.

This is just a glimpse. There are so many others already doing the work. They’re recommending products, covering the sale events, building brand affinity with their audiences. The sponsorship deal just hasn’t happened yet. For Sephora, that’s a massive runway of aligned writers they could activate. For the writers, it’s evidence that the brand relationship already exists in practice, even if it hasn’t been formalized.

The Bigger Opportunity

Sephora is one of the few beauty brands actually writing checks to Substack writers. Most beauty brands on the platform right now aren’t sponsoring newsletters. They’re benefiting from affiliate links and organic mentions. For example, Crown Affair is showing up in Btwn Meals, Big Salad, Earl Earl by Laurel Pantin, The Strict List. Hanni is in oh mon dieu and The Ray List. Elemis is mentioned in Platonic Love, Joie De Vivre, So Many Thoughts. But in most of these cases, the writer is sharing affiliate links or mentioning the brand organically because they genuinely use the products. The brand isn’t paying for the placement.

That’s the gap. And it’s enormous.

Think about what this means. Writers across Substack are already driving sales for beauty brands through affiliate programs, and in most cases, the brand has little to no direct relationship with them at all.

On the tech side, this gap barely exists anymore. Brands like Vanta and WorkOS identified the newsletters where their products were already being mentioned organically and converted those into sustained paid campaigns. That’s how you go from 0 to 93 placements. The organic mention was the signal. The sponsorship was the commitment.

Beauty has a version of this happening right now, but with an extra layer: affiliate. Writers aren’t just mentioning these brands organically. They’re actively linking to them and driving sales. Which means beauty brands have even more data to identify which writers are worth sponsoring. The proof of purchase is already there.

For writers, especially smaller ones: if you’re regularly linking to beauty brands through affiliate programs, you already have the data to make a pitch. You know how many clicks you’ve driven. You know what your readers buy. That affiliate history is your media kit. The conversation with a brand shouldn’t be “would you like to sponsor my newsletter?” It should be “I’ve already been selling your products. Here’s what a real partnership could look like.”

If you want a real playbook for how to actually do this, Erika Veurink wrote one of the best things I’ve read on the subject. She replaced a six-figure tech salary in her first quarter of full-time newsletter writing, partially through brand deals, and her post breaks down exactly how she approached partnerships from zero. Worth your time. (Also worth noting: Erika writes Long Live, which just recently featured a sponsorship by Adobe. She’s not theorizing. She’s doing it.)

For beauty brands: the writers who are already converting for you are your most valuable partners, and right now, most of you aren’t paying them. That’s fine in the short term. But as Substack’s advertising ecosystem matures and more brands start locking in paid partnerships with these writers, the ones who moved first will have their pick. The affiliate layer is your test market. The data is already there. The question is whether you’re going to act on it before your competitors do.

And for the Substack ecosystem overall: this is what the maturation curve looks like. Tech brands have already made the jump from organic mentions to sustained sponsorships. Beauty is stuck between affiliate and paid.

The writers and brands who figure out how to bridge that gap first will define what beauty advertising looks like on this platform.

The Takeaway

For writers: your affiliate data is your media kit. Use it.

For brands: the writers already talking about you are a map of where your next partnerships should be.

More to come next week. If there’s a brand or category you want me to dig into, drop it in the comments.

Welcome to On Brand: a new column on The Messy Middle where I track how brands are showing up on Substack as a media channel. What’s working, what’s not, and what it means for writers and brands.

A little context on why I’m writing this: I’ve spent nearly a decade at Reddit working in brand partnerships. My job was to help advertisers understand why they should spend money reaching Reddit’s communities, and more importantly, which communities were worth their investment. I watched the entire arc of a platform going from “we don’t know how to advertise there” to “we can’t afford not to.” I think Substack is at the beginning of that same arc right now.

Brands are starting to show up here, but most writers don’t have visibility into who’s spending, where they’re placing, or what the landscape actually looks like. And most brands exploring Substack don’t have a good read on what other brands are doing or where the opportunities are. This column is designed to change that.

I know ads on Substack can be a polarizing topic. Some writers came here specifically to escape the ad-supported model, and I respect that. But the reality is, brands are already here and more are coming. That’s not a threat to the platform, it’s a sign that it’s maturing. The question isn’t whether brands will show up on Substack. It’s whether they’ll show up well. The difference between an ad that feels intrusive and a partnership that feels natural comes down to fit, trust, and how well a brand understands the community it’s entering. That’s what I spent nearly a decade thinking about at Reddit, and it’s exactly what I’ll be paying attention to here.

Every week, I’ll share what I’m seeing: which brands are making moves, where the money is flowing, what categories are heating up, and what’s notably absent. Whether you’re a writer thinking about how to monetize, or a brand trying to figure out if Substack is worth your budget, this is for you.

Let’s get into it.

The Signal

I’ve been tracking brand activity across more than 100 Substack newsletters spanning tech, finance, lifestyle, fashion, food, wellness, and culture. And the picture is striking: the Substack advertising ecosystem is, right now, dominated by B2B tech and finance.

The top spenders tell the story. Brex: 130 paid sponsorship placements across 5 newsletters. Vanta: 92 across 9. WorkOS: 63 across 6. Then Mercury, Turing, Deel: tech, fintech, tech, fintech, on and on. The newsletters they’re sponsoring? Not Boring by Packy McCormick, The Pragmatic Engineer, Lenny’s Newsletter, ByteByteGo, The Generalist. Business and tech newsletters with massive audiences, and the brands showing up in them are selling to founders, engineers, and operators. These newsletters were early to monetize, and the brands spending in them have the budgets and attribution models to justify sustained campaigns.

But the lifestyle side is starting to wake up. Brands like Banana Republic, Sezane, and Quince are making real paid investments in newsletters like Big Salad, Scratch Pad, and Not Boring. Caroline Chambers’ What To Cook When You Don’t Feel Like Cooking (568K subscribers) is attracting sponsors like Thrive Market, Kosterina, and Cuisinart. Emily Sundberg’s Feed Me has brands like Brooklinen, Free People, and Glossier showing up. These aren’t affiliate links, these are actual paid sponsorships.

But the scale tells the real story. Thrive Market has 11 sponsorship placements across 2 newsletters. Brooklinen has 8 across 6. Compare that to the tech side, where Brex has 130 and Vanta has 92. The lifestyle brands are experimenting. The tech brands are running sustained campaigns.

That gap is the opportunity, for writers building audiences in these categories and for brands ready to commit beyond a test.

The Spotlight: When a sponsorship doesn’t feel like one

Two partnerships caught my eye recently that show what good brand-newsletter fit looks like, and how different it can look depending on the context.

Grace Atwood’s Scratch Pad recently featured Sezane as a sponsor in her post “A Place for the Nerds.” If you read it, you might not have even registered it as an ad, because Grace already wears Sezane. She’s featured the brand in her content before, not because they were paying her, but because she likes the clothes. So when Sezane shows up as a sponsor, it feels like a natural extension of what she’s already talking about, not an interruption. The reader doesn’t feel sold to because the recommendation isn’t new, it’s just formalized.

Sezane in Scratch Pad

Then there’s Quince in Not Boring by Packy McCormick. At first glance, an affordable fashion basics brand in a tech and business strategy newsletter seems like an odd pairing. But read how Packy writes about it and you'll see why it works. He's a Quince investor. He's wearing Quince jeans and a Quince q-zip while he writes the post. He dresses his kids in Quince. He breaks down their M2C operating system like he would any business he's excited about. It reads like a founder pitch from someone who genuinely believes in the product, not like an ad slot that got filled. That's the difference. The fit isn't about category. It's about audience mindset and authentic connection to the brand.

Quince in Not Boring by Packy McCormick

These two examples illustrate something important: good sponsorship on Substack isn’t about finding a newsletter that matches your brand’s category. It’s about finding one that matches your brand’s values and your customer’s identity. Sezane in Scratch Pad works because the readers already shop there. Quince in Not Boring works because the brand understood the audience, not just the topic.

For writers: think about which brands align with how your readers see themselves, not just what your newsletter is “about.” For brands: the best placements on Substack won’t always be in the most obvious category. The right room might surprise you.

The Takeaway

For writers: the paid brand dollars are starting to arrive in lifestyle, food, and wellness, but they’re still early. The writers who are building engaged, trusting communities right now will be the ones brands want when the spending catches up.

For brands: the audiences are already here. Massive, loyal, engaged readerships built on trust that’s nearly impossible to replicate on Instagram or TikTok. The early movers are going to have their pick of partnerships. The question is whether you get there before everyone else does.

More to come next week. In the meantime, if there’s a brand you’re curious about or a topic you want me to dig into, drop it in the comments. This column is for you.

I’ve spent nearly a decade at Reddit, from scrappy startup through IPO, working in brand partnerships. My job was to help advertisers understand why they should spend money reaching Reddit’s communities. And the single hardest thing to explain wasn’t Reddit’s scale. It was why scale wasn’t the point.

Here’s the pitch I made hundreds of times: A subreddit with 40 million subscribers and a subreddit with 50,000 subscribers could both be valuable to a brand. But the 50,000-person community? The one where people showed up every day, knew each other’s usernames, had inside jokes and shared language and unwritten rules? That was often worth more. Not because the number was impressive on a media plan, but because when those people talked, other people listened. When they recommended something, people bought it. When they rallied around an idea, it moved.

The big subreddits had reach. The small ones had influence.

I think about this constantly now that I’m building on Substack.

The Growth Conversation Nobody Is Questioning

If you spend any time on your Substack feed, you’ll notice a genre of content that’s everywhere: how to grow your subscriber list, how to convert free readers to paid, how to optimize your Notes strategy, how to hit 1,000 subscribers in 90 days. Growth tactics. Funnel language. The machinery of audience-building.

And look, none of that is wrong. You need readers. Subscriber count matters. Revenue matters if you’re trying to make this a real thing. I get it. I’m not above caring about my own numbers.

But there’s something missing from that conversation, and it’s the thing I keep coming back to from my years in the platform world: reach is only as valuable as the community behind it.

A thousand subscribers who opened your email, skimmed it, and moved on are worth less than a hundred who read every word, replied, shared it with a friend, and come back day after day. You know this intuitively. But the growth advice rarely accounts for it, because cohesion is hard to measure. It doesn’t fit in a screenshot. You can’t brag about it in a milestone post. It’s less sexy than sheer numbers.

What Reddit Taught Me About Community

At Reddit, the communities that brands actually wanted to be part of, the ones that drove real results, shared a few things in common.

They had a reason to exist beyond the platform. They weren’t just “people who clicked subscribe.” They were bound together by a shared identity, obsession, or life stage. The best communities felt like they would have found each other anyway and Reddit just gave them the room.

r/SkincareAddiction wasn’t just a beauty forum: it was a place where people genuinely trusted each other’s recommendations in a way that no brand campaign could replicate.

r/personalfinance wasn’t just money advice: it was a space where people felt safe being vulnerable about debt, savings, and financial fear in ways they couldn’t anywhere else.

r/MealPrepSunday wasn’t just recipes: it was a weekly ritual for people who took their Sundays seriously. The community existed because of a shared identity, not because of an algorithm.

The regulars set the tone, but don’t underestimate the lurkers. Every community had a group of Moderators that set the tone, enforced the norms, and made new people feel like they’d found something. That small group was the engine. But the lurkers? They were often the ones who bought. They were reading every word, absorbing every recommendation, acting on it quietly, and telling their friends. The silent majority matters more than most people realize.

They were specific. The most engaged communities weren’t trying to be everything to everyone. They were narrow by design. That narrowness wasn’t a limitation, it was the whole point. It’s what made people feel like they belonged and produced such rich conversation and connection. Take r/April2026bumpers — a community that exists solely for people due the same month, where you need to show proof of your due date to join. That specificity is exactly what makes it invaluable. The conversation is richer because everyone in it is living the exact same moment.

I watched this pattern repeat across thousands of communities over nearly ten years. The ones that tried to be big first and meaningful second almost always flamed out. The ones that were specific, intentional, and a little bit weird? They lasted. They grew on their own terms. And they became the places people actually cared about.

What This Means For Brands

Because I can’t not think about brands.

Big communities gave brands scale. Niche communities gave them something harder to buy: relevance.

Brands didn’t need help finding r/AskReddit. They asked me to find the niche subreddits that were relevant to their particular product, audience, or moment. The brief was never “find me the biggest room.” It was “find me the right room.” Relevance always beat reach. Every time.

I think the same shift is coming on Substack, and the brands that get there first will have a real advantage.

Right now, most brands approaching Substack are thinking about it the way they thought about early Instagram: build your own channel, grow your own following, broadcast your own content. Some are doing it well.

Tory Burch was one of the first major fashion brands on the platform, building a newsletter that mixes product insight with cultural commentary and links generously to other writers rather than just promoting itself.

The RealReal treats their Substack as a genuine editorial channel, not a marketing one, written in a Gossip Girl-esque voice by an anonymous 'RealGirl.’

Hinge used the platform to tell real love stories through their No Ordinary Love campaign, partnering with writers in a way that felt native to Substack rather than bolted on, and extending the campaign into book clubs and out-of-home advertising.

Dianna Cohen, founder of Crown Affair, writes a newsletter called Take Your Time about the art of becoming who you are: not a brand newsletter in any conventional sense, but a founder writing honestly about building a life and a company simultaneously. The community it’s building isn’t just Crown Affair customers. It’s people who see themselves in her story.

But that’s only half the opportunity.

The other half? Investing in the writers already building niche, highly engaged communities, the ones whose readers trust them deeply, show up consistently, and actually act on what they read. Not because of their subscriber count. Because of their connective tissue.

The brands that figured this out on Reddit didn’t just build their own subreddits. They showed up authentically in the ones that already existed. I think the same playbook is about to unfold here.

That’s exactly what I’ll be exploring in my upcoming column, On Brand: tracking how brands are engaging with Substack as a media channel, what the smart ones are looking for beyond subscriber count, and what the next era of creator-brand partnerships actually looks like. More on that soon. 👀

The Question Nobody Is Asking

The Substack growth conversation tends to treat subscribers as a uniform commodity, more is better, always. But anyone who’s built a real community knows that’s not how it works. A subscriber isn’t a subscriber isn’t a subscriber. What matters is whether those people are bonded by something. Whether they’re a cohesive group or a random collection of email addresses.

This is the question I don’t see enough writers asking: Who is this for, and what holds them together?

Not “how do I get more people.” But “what is the connective tissue?” What’s the shared identity or experience that makes someone read your post and think, this is my place, and these are my people?

Because if you can answer that, the growth part gets easier. Not because you’ve hacked the algorithm, but because people who feel like they belong somewhere tend to invite other people in. They advocate on your behalf. That’s not a growth strategy. That’s just how communities work.

So here's what I'd actually focus on. I'm starting from scratch myself, so consider this as much a note to me as it is to you.

Be specific about who you’re writing for, and make that specificity feel like an invitation, not an exclusion.

Respond to every comment, especially early on. Your readers need to feel like there’s someone real on the other side.

Write notes and posts that invite conversation, not just agreement.

And let your readers see each other: reference comments, name people, create a sense of room. The goal isn’t to broadcast to an audience. It’s to convene a community.

The Only Metric That Actually Matters

I’m early in building The Messy Middle. My numbers are small. But when someone replies to a post and says “I feel like you’re writing about my exact life right now” that’s the signal I’m paying attention to. Not the subscriber count. Not the open rate.

The moment a reader feels like they’ve found their people: that’s the metric nobody talks about. And it’s the only one that actually matters.

Someone asked me for free advice this week. And I almost said no.

Not because I didn’t want to help. I was actually really excited to help. But because I’ve spent fifteen years building expertise inside someone else’s company, and I’m in the early stages of figuring out what it looks like to attach that expertise to my own name. And something about giving it away for free felt like the wrong foot to start on.

But then I thought about where I actually am right now.

I don’t have a client list. I don’t have case studies yet. No track record under my own banner. No proof that this works. Just fifteen years of experience that nobody can see yet, because it all happened inside a company, not outside one.

And I realized: the problem isn’t my rate. It’s visibility. The problem is that nobody has seen me work yet.

So I said yes. But I said yes strategically.

Here’s what I mean.

A few weeks ago, I did something that felt equal parts exciting and terrifying.

I cold outreached to a founder whose work I’d been following. I didn’t know her. She didn’t know me. I just sent a message saying I admired what she was building and thought I could help.

She wrote back.

We got on a call. The conversation was good. She was interested in what I brought to the table, but honest that she wasn’t sure yet if she could bring me on in any formal capacity, mostly due to financial reasons.

I filed it away as a good conversation, a new addition to my network, and moved on.

Then this week, she reached back out. This time, she was working on something specific. She had put together her positioning, her pitch deck, her ideal brand partner list… and wanted my input.

And I had a decision to make.

Do I give her real, substantive feedback for free? Do I hold back and wait until there’s a formal engagement? Do I offer something in between?

It’s a question I didn’t have a clean answer to. And I suspect a lot of people navigating a career pivot run into the same thing- especially when you’re trying to monetize expertise you’ve spent years building inside someone else’s company.

The case for giving it away

When you’re building a client base from scratch, your biggest problem isn’t your rate. It’s that nobody has seen you work yet.

For fifteen years, my expertise lived inside a company. The results I drove, the relationships I built, the deals I closed - all of that happened under someone else’s banner. Now I’m trying to attach that same expertise to my own name, and the honest truth is: that takes proof.

Free work, when done strategically, can serve as that proof.

The key word is strategically. There’s a difference between giving someone a sample of what you can do and just doing the work for them indefinitely without compensation. One builds your reputation. The other erodes it.

The case for protecting your value

Here’s the other side of it.

Every time you say yes to free work, you’re training people (including yourself) about what your expertise is worth. And that’s a harder thing to undo than most people realize.

The temptation early on is to say yes to everything. To prove yourself before anyone has given you the chance to. But there’s a version of that generosity that quietly becomes a pattern, and patterns are hard to break.

The people who ask for free work aren’t always the people who will eventually pay for it. Sometimes they’re just people who ask for free work.

So the real question isn’t “should I do this for free?” It’s three smaller ones:

Is this the right person? Is this the right situation? And is what I’m giving away actually a sample of my best work, or just the work itself?

The framework I landed on

Before saying yes to free work, I’ve started asking myself:

Is there a realistic path to a paid engagement here? Free work that has no clear next step is just unpaid work. Free work that opens a door is an investment.

Am I demonstrating a specific skill, or just doing the work for them? There’s a difference between showing someone what you’re capable of and becoming their unofficial consultant before any agreement is in place.

Do I control the scope? A defined, bounded piece of feedback is a sample. An open-ended “can you look at this?” with no clear limits is a trap.

What’s the explicit next step? If you deliver something valuable, there should be a natural conversation that follows. If there isn’t, you need to create one.

Does this align with how I want to be known? Every piece of work you put your name on, paid or unpaid, is building your reputation. Make sure it’s the reputation you actually want.

Have I actually run the numbers, or am I assuming I can’t afford to wait? Most people never do the real math on what they actually need versus what they think they need. Knowing your real number changes the calculus on every free work decision.

What I actually did

In the end, I gave real, substantive feedback. Not a watered-down version designed to tease what I could offer, but actual, useful, concrete input that I knew would help.

But I also used it deliberately. I showed a specific slice of my expertise. I kept the scope defined. And at the end of the conversation, I proposed concrete next steps.

She said she’d circle back when she was ready.

Which means I’m now sitting with that particular kind of limbo that comes with early stage relationship building. You’ve shown your value, you’ve made an impression, and now you wait.

Her response when she received the feedback? She called it a gift.

But the path forward is still unclear. And I’d be lying if I said I wasn’t second-guessing myself a little. Did I give too much away too soon? Was the feedback so complete that there’s nothing left to pay for? I genuinely don’t know yet.

What I do know is this: building something new, whether a client base, a reputation, or a consulting practice from scratch requires a different calculus than maintaining something established. You have to give a little to get started. The trick is knowing exactly how much, to whom, and in exchange for what.

And the next time a similar situation comes up? I’ll think about it differently. That’s exactly how this is supposed to work.

While I was sitting with the uncertainty of that conversation, someone else reached out- not because I pitched them, but because they read my writing and connected with what I was building. We have a call scheduled this week.

A reminder that the best opportunities don’t always come from the doors you knock on. Sometimes they come from the ones that find you.

I spent fifteen years building expertise inside someone else’s company. Now I’m figuring out what it looks like to build something of my own.

That means navigating questions I never had to ask before. About value, about positioning, about when to give and when to hold back.

I don’t have all the answers yet. But I’m figuring it out, one conversation at a time.

If this resonated, subscribe to The Messy Middle for weekly dispatches from the space between the career you built and the life you actually want. And if you know someone navigating their own version of this, I’d love it if you shared it with them.

One of many versions of work over the past nine years - back in my San Francisco apartment, with my favorite coworker.

I joined Reddit nine years ago, when it was still a scrappy startup and I was in my mid-twenties.

I didn’t plan to stay long. Like most people early in their careers, I assumed I’d make a few quick moves, a couple of years here, a promotion there, always chasing the next thing.

Instead, I stayed through leadership changes, product pivots, a very public IPO, good years, hard years, and more than a few moments where I seriously considered leaving.

Spending nearly a decade inside one company, and one very strange corner of the internet, gives you a perspective you can’t get any other way. You see things compound. You see things collapse. You watch careers unfold in slow motion, including your own.

Here’s what I know now that I couldn’t have understood when I started.

1. The internet reveals what people actually think

One thing I didn’t expect when I joined Reddit was how much it would change the way I see people.

When you spend enough time watching online communities, you realize most people aren’t as polished as they seem in real life, and they’re not as terrible as the internet sometimes makes them look.

They’re just human. Curious, insecure, opinionated, generous, stubborn, helpful, defensive, kind - often all at the same time.

The internet doesn’t create those traits. It just makes them visible.

Once you see that up close, you start to understand people differently everywhere else too. Most of us are just doing our best.

2. The loudest voices aren’t the majority

Working at Reddit teaches you quickly that the most visible opinions aren’t always the most common ones.

The people posting the most, commenting the most, reacting the strongest - they don’t always represent how everyone feels. They just show up more.

That’s true online, but it’s also true at work, in friendships, and in life.

Not every criticism means you’re on the wrong path. Not every quiet moment means nothing is working. Sometimes the majority just isn’t the loudest.

3. The most interesting things happen in small communities

You’d assume the biggest conversations happen in the biggest spaces. In my experience, the opposite is usually true.

Some of the most thoughtful, engaged communities on Reddit are surprisingly small, niche groups built around specific interests, where people show up because they genuinely care, not because an algorithm put them there.

I’ve seen the same pattern in careers, in friendships, in this phase of life. The biggest rooms aren’t always where the most meaningful things happen.

4. People work with people they trust, not just platforms

Early on at Reddit, I reached out to a few clients I’d worked with at my previous company. On paper, their brands weren’t an obvious fit, the platform was different, the ad products were different, and for some of them it felt like a real risk.

But they trusted me.

It took almost a year of conversations before one of them tested the platform. That campaign ended up being one of the first financial services brands to ever advertise on Reddit.

That experience taught me something I’ve never forgotten: products change, companies change, roles change. But trust carries over.

People don’t invest in platforms. They invest in people they genuinely trust.

5. It matters more to be respected than impressive

This industry is smaller than it looks. Your reputation follows you longer than you think.

You don’t have to be the smartest or loudest person in the room. Being known as kind, reliable, and genuinely hard-working goes further than most people expect, and those impressions compound quietly over time.

People remember how you show up, long after they’ve forgotten what you sold them.

6. Relationships compound more than any org chart

Products change. Leadership shifts. The thing you’re selling today might look completely different next year.

Especially in sales, the only real constant is the relationship you’ve built.

I learned not to rush a deal to hit a number. Not to treat people as transactions. To listen, be honest, and show up consistently - even when there was nothing immediate to gain.

Relationships compound in ways that no title or org chart ever will.

7. Knowing when to stay matters as much as knowing when to leave

There were many points over the years where I thought seriously about leaving.

Startups are exciting, but they’re also exhausting. There’s constant change, constant uncertainty, and moments where walking away feels easier than pushing through.

For one reason or another, I stayed. Looking back, some of those decisions were among the most important of my career. Had I left too early, I would have missed opportunities I couldn’t have seen coming.

Not every hard season means you’re on the wrong path. Sometimes the real skill isn’t knowing when to quit - it’s knowing when to keep going.

8. The season of life you’re in changes how you see work

In nine years, I got engaged, married, brought home a puppy, bought a house, moved to the suburbs, and had two kids. Reddit went from startup to public company. I went from mid-twenties to mid-thirties.

You can’t plan the exact path. You don’t know what season of life you’ll be in when you get there, or how much it will change what matters to you.

What feels urgent at 26 doesn’t always feel urgent at 35. That’s not failure. That’s just life moving through you.

9. Sometimes you choose the smaller career to protect the bigger life

This is the one I keep coming back to.

Over the years there have been many promotion cycles. Some of them, I pushed hard. I wanted the bigger role, more responsibility, the next level.

Other times, especially since becoming a mom, I made the conscious decision not to. Not to move into management. Not to take the role with more travel. Not to trade the flexibility I’d built for a title that would cost more than it gave.

Not because I stopped caring about my career. But because I wasn’t willing to make the trade-offs that came with those next steps.

For this season of life, having more control over my time matters more than having a bigger title.

Sometimes you choose the smaller career to protect the bigger life.

And sometimes, that’s exactly the right call.

Nine years at one company wasn’t something I planned. But staying long enough to see the full arc - the growth, the hard seasons, the change, taught me more than moving fast ever could have.

The internet changes quickly. Companies change quickly. Careers change quickly.

But the things that matter most - trust, relationships, timing, and knowing what season you’re in, tend to stay the same.

I’ve been thinking a lot lately about what the next season is going to ask of me. I don’t have the answers yet.

But I’m figuring it out here, one essay at a time.

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During that time, I’ve watched millions of conversations unfold across thousands of communities- about everything from parenting and skincare routines to personal finance, politics, and obscure hobbies I didn’t know existed.

If you spend enough time watching how people behave on the internet, certain patterns start to emerge.

Reddit is often described as chaotic, opinionated, and occasionally brutal. But it’s also one of the most honest mirrors of human behavior online.

After years working inside the platform, a few things about the internet have become hard to unsee.

The internet reveals what people actually think

Most platforms encourage people to present the best version of themselves. The one with filters and carefully curated highlight reels.

The anonymity of Reddit often allows people to show up differently. Often more honestly. Sometimes more vulnerably.

I’ve seen this lead to moments of real authenticity.

Someone in r/personalfinance asking for help figuring out how to pay off student debt.

Nervous moms-to-be in r/babybumps supporting each other through the anxieties of early pregnancy.

Exhausted entrepreneurs leaning on each other in r/freelancing.

For all the criticism the internet receives, moments like these remind me that people are often showing up with genuine curiosity and a desire to help each other.

Reddit, sometimes called “the homepage of the internet”, holds space for all of humanity.

The good, the messy, and everything in between.

Communities are smarter than brands think

One thing you notice quickly working around Reddit is how often brands underestimate communities.

Every so often, a company will drop into a conversation with something that feels a little too polished, a little too obviously marketing.

The response is usually immediate.

Someone in the comments will ask, “Is this an ad?”

And suddenly the entire thread shifts. The conversation becomes about the brand’s presence rather than the original topic.

Redditors don’t actually hate ads.

Given the performance I’ve seen from thousands of campaigns over the years, that theory simply doesn’t hold up.

What Redditors hate is the feeling of being tricked or being talked down to.

Treat the community with respect, and they’ll often return the favor.

People trust other people more than institutions

At the same time, I’ve watched complete strangers spend hours helping each other solve problems.

Someone will post a question about parenting, career decisions, health concerns, or how to fix something broken in their house.

Within minutes, dozens of people show up offering advice, personal experience, or encouragement.

Most of them will never meet each other. There’s no incentive beyond simply wanting to help.

For all the negativity that sometimes dominates headlines about the internet, moments like these reveal something different.

Online communities can be powerful places for collective knowledge and support.

The most interesting parts of the internet are small

One of the biggest misconceptions about the internet is that the most interesting conversations happen in the biggest places.

In reality, some of the most thoughtful and engaged communities on Reddit are surprisingly small.

Niche groups devoted to incredibly specific interests from bread baking techniques to obscure sports analytics to hyper-local parenting advice.

These smaller communities often develop the strongest norms, the most interesting conversations, and the deepest sense of belonging.

The internet isn’t just one giant crowd.

It’s thousands of smaller rooms where people gather around shared interests.

Participation matters more than broadcasting

The brands that succeed on Reddit tend to do one thing well: they listen first.

What are communities already saying about your brand?

What are people saying about your products - the good and the bad?

Are you really hearing them with an open mind?

Reddit can be an incredibly valuable feedback loop if you’re willing to engage with it honestly.

Yes, there will sometimes be criticism.

But criticism can also be insight. A window into how real people experience your product.

The brands that approach communities with curiosity instead of control often learn the most.

Working inside Reddit for so many years changed how I think about the internet.

Beneath all the algorithms and platforms, the internet is still fundamentally about people. Their curiosity, opinions, questions, and desire to connect with others who care about the same things.

The platforms will keep changing.

But the human behavior underneath them rarely does.