How I Completely Screwed Up Reddit Marketing (And You Probably Will Too)

Okay so I'm sitting here with my third cup of coffee today (don't judge me), scrolling through my old Reddit posts and literally cringing at myself. Like, physically cringing. If there was a way to travel back in time and slap my past self, I would.

But since time travel isn't a thing yet, I figured I'd at least write down all the stupid stuff I did so maybe someone else won't have to learn the hard way. Though honestly? You probably won't listen to me anyway. I sure didn't listen when people tried to warn me.

The Affiliate Link Disaster (AKA How I Got Banned in Record Time)

So this one time - and I'm still embarrassed about this - I thought I was being super clever. Found this productivity subreddit, saw people asking for tool recommendations, and boom! Posted my "helpful" article with affiliate links buried in there.

I literally sat there refreshing the page every 30 seconds like some kind of maniac. Wife walked by, saw me staring at my phone, and was like "What are you doing?" I mumbled something about "checking engagement metrics" which... yeah, that sounds as pathetic as it was.

Two hours later: post removed. Twenty-four hours later: temp ban.

The worst part? I actually got defensive about it. Messaged the mods like "But I was being helpful!" facepalm

Now I just... don't do that. At all. If I want to mention a product, I either:

• Write about it on my own blog first, then share that (sometimes)
• Just recommend stuff without any links because, shocking revelation, people can Google things
• Actually use the product for more than five minutes before talking about it

Side note: I still sometimes catch myself thinking "ooh, I could totally slip a link in here" and then I remember The Great Ban of 2024 and calm down.

What about you? Have you ever tried to sneak in an affiliate link and instantly regretted it? Share your story in the comments.

My "Look at My Cool Startup" Phase (Maximum Cringe Warning)

Oh god, this phase. I built this little side project - nothing fancy, just a simple tool I thought was useful. And I was SO excited about it that I basically became that guy at parties who only talks about his new business idea.

Posted about it in r/SideProject on a Monday. Then r/entrepreneur on Tuesday. r/startups on Wednesday. Same link, slightly different titles each time because I thought I was being sneaky.

Results?

• 3 upvotes total across all posts
• One comment that just said "spam"
• Several people calling me out for cross-posting
• Me spending way too much time explaining in comments why it "wasn't spam, it was sharing valuable resources"

Ugh. Even writing this now makes me want to hide under a blanket.

What I do now (when I remember to do it right):

• I spend like 90% of my time just commenting on other people's stuff
• When I do share something, I'm genuinely worried it might be too self-promotional
• I ask myself "would I want to see this if someone else posted it?" and usually the answer is no, so I don't post it

Random thought: It's weird how the less I try to promote my stuff, the more people seem to care about it. Like, reverse psychology or something?

Ever had a moment where you over-promoted something and instantly realized you messed up? Let's hear it.

Subreddit Rules Are Apparently Important (Who Knew?)

Each subreddit has its own rules and oh my god, some of them are SO specific. Like, r/personalfinance will remove your post if you use the wrong flair. Not kidding. I learned this the hard way.

Posted this long, thoughtful thing about budgeting strategies. Spent like an hour writing it. Used the "Other" flair because I couldn't figure out which one fit. Boom - removed for wrong flair.

I was so annoyed I almost rage-quit Reddit entirely. My girlfriend had to talk me down from deleting my account. "It's just a flair," she said. She was right, but I was still mad.

Now I have this whole routine:

1. Read the rules (actually read them, not just skim while thinking about lunch)
2. Look at what successful posts look like in that subreddit
3. Check if they want specific formatting or whatever
4. Sometimes message the mods if I'm confused (some are actually nice!)

Pro tip that took me forever to learn: Each subreddit has its own weird culture. r/entrepreneur loves hustle stories. r/personalfinance wants spreadsheets and data. r/getmotivated wants... I still don't understand r/getmotivated honestly.

What’s the most ridiculous subreddit rule you’ve encountered? Drop it in the comments so we can all laugh together.

Clickbait Titles Don't Work (Shocking, I Know)

Remember when I said I was sitting here cringing at my old posts? Yeah, the titles are the worst part.

"This One Productivity Hack Changed My Life" - actual title I used. I KNOW. I'm sorry. I was young and stupid and thought internet marketing tactics from 2015 still worked.

The post got downvoted so fast I thought there was a glitch. Checked my phone obsessively for like an hour thinking maybe Reddit was broken. Nope, just my title was trash.

Now I try to write titles like I'm texting a friend:

• "Tried the Pomodoro thing for a month, here's what happened"
• "Why my morning routine keeps falling apart"
• "My productivity app addiction is getting out of hand"

Still not great at it though. Sometimes I write a title, rewrite it five times, then just give up and post whatever.

Confession: I still write clickbait-y titles sometimes and then delete them before posting. Old habits die hard.

Ever posted a title so bad you wanted to delete it instantly? I’ve been there. Share yours.

The New Account Struggle Bus

Starting fresh on Reddit is like being the new kid at school, except everyone can see exactly how new you are and judges you for it.

Made a new account specifically for business stuff (probably mistake #1) and immediately tried to post valuable content. Key word: tried.

Most subreddits have karma requirements. Some have account age requirements. Even when they don't, people can smell a new account from a mile away and they're suspicious as hell.

Spent my first week basically lurking and upvoting random stuff, feeling like a creeper. Left some comments that I thought were insightful but were probably just awkward.

True story: I once spent 20 minutes crafting the perfect comment, posted it, got one upvote (probably my own), and felt irrationally disappointed for the rest of the day.

What actually works for new accounts:

• Just... exist for a while before trying to do anything
• Comment on stuff you actually care about (this can't be faked, people notice)
• Don't post any links for like two weeks minimum
• Accept that building karma takes forever and is kind of arbitrary

Any new Redditors out there struggling with this? Drop a comment - we can suffer together.

Comments Are Where the Magic Happens (But Also Where I Embarrass Myself)

Here's something nobody tells you: the real conversation happens in the comments. The post is just the conversation starter.

I used to post something and then disappear because I was scared of saying something stupid in the comments. Plot twist: not engaging is actually stupider than saying something dumb.

My most successful posts were ones where I stayed active in the comments for like 48 hours straight. Literally checking my phone every few minutes. My productivity ironically tanked while I was trying to give productivity advice.

Some of my best business connections came from random comment threads, not from the posts themselves. Still talk to a few people I met that way.

What I try to do now:

• Reply to every comment (even the mean ones, with varying levels of success)
• Ask follow-up questions to keep conversations going
• Actually read what people are saying instead of just waiting for my turn to talk

Confession: I still sometimes write a comment, read it over ten times, decide it sounds stupid, and delete it. Social anxiety is real, even online.

What’s the weirdest comment thread you’ve ever been in? I’d love to hear it.

The Crossposting Disaster

Thought I was being efficient by posting the same thing to multiple subreddits at once. Spoiler alert: Reddit doesn't like this.

Posted about a productivity tool to r/productivity, r/getmotivated, and r/lifehacks all within like an hour. Same content, same link, barely different titles.

Got called out for spamming almost immediately. Someone even made a comment like "nice spam, reported" which made me feel like absolute garbage for the rest of the day.

Now I:

• Actually rewrite posts for different communities (takes forever but whatever)
• Wait at least a day between crossposts, sometimes longer if I remember
• Try to make sure the content actually fits the community culture

Example: A post about productivity would be totally different for r/ADHD (focus on struggles and real talk) vs r/entrepreneur (focus on results and metrics) vs r/college (focus on study tips and being broke).

Have you ever been caught crossposting? Tell me how bad it was. I’ll feel less alone.

Building Relationships with Mods (Yes, This Is A Thing)

This felt super weird at first, but moderators are just people who happen to care a lot about their communities. Some of them are actually really helpful.

Started reaching out to mods before posting anything remotely promotional. Not to kiss up, just to make sure I wasn't about to do something stupid.

Results have been... mixed. Some mods are awesome and will actually help you improve your posts. Others seem to be on permanent power trips and will ignore you or give you attitude.

How to not annoy mods:

• Read the rules first (seriously, they can tell when you haven't)
• Be respectful and don't waste their time
• Don't ask for special treatment, just ask for clarification
• Accept their feedback without arguing (learned this one the hard way)

Real talk: Some mods have actually become casual internet friends. It's weird but cool.

Have you ever had a surprising mod interaction? Share it - I love hearing these stories.

What Actually Works (The Stuff I Wish Someone Had Told Me)

After making literally every mistake possible, here's what I've figured out:

Be helpful first, worry about promotion never: Seriously. I spend like 80% of my Reddit time just answering questions and trying to be useful. The other 20% is when I share something I made. That 20% works way better because of the 80%.

Share your failures: My most popular posts have been about things that didn't work or mistakes I made. Redditors love authenticity, even when it's messy.

Use normal human language: I still catch myself trying to sound "professional" sometimes. Nobody wants that on Reddit.

Time your posts: Each subreddit has different peak times. I use some free tool to figure this out, though I forget to check half the time and just post whenever.

Pick 1-2 subreddits and actually participate: Better to be known in a couple communities than ignored in twenty.

Accept that it's slow: Reddit growth is painfully slow. I still get impatient and try to force things sometimes. Never works.

The Bottom Line (Or Whatever)

Reddit in 2025 isn't about clever marketing tricks. It's about being a real person who sometimes has something worth sharing.

The accounts that work long-term are run by people who genuinely enjoy being part of their communities. Not because it's a strategy, but because they actually like the conversations.

My current approach: I spend most of my Reddit time just being a community member who happens to occasionally build things. When I do share something, I'm usually genuinely nervous about whether it's good enough or too self-promotional.

If you're starting out, resist every urge to promote anything for at least a month. Use that time to figure out how each community actually works. Future you will thank past you.

Random confession: I still check my post karma way too often and get irrationally happy when something does well. Some things never change.

What’s the dumbest mistake you’ve made on Reddit? Drop it in the comments - let’s cringe together.

Been making mistakes on Reddit for about 3 years now. Currently active in a few communities when I remember to check Reddit instead of doom-scrolling Twitter. Feel free to ask questions in the comments, though I can't promise my answers will be helpful.

Also, if you see any typos, please ignore them. I wrote this while slightly caffeinated and definitely didn't proofread it properly.