I started this newsletter because I had too many opinions and not enough places to annoy people with them. Today those opinions have a home that 20,000 humans have chosen to live in, which feels both ridiculous and quietly terrifying.
As of October 7, 2025, Stupidpreneur has crossed 20k subscribers. We hit 10k on September 19, 2025, and then something surprising happened: we brought Peak Shift into the family, and that acquisition pushed us over the next hill faster than any virality stunt, hack, or influencer cameo ever could.
If you remember, Peak Shift was running in the same neighborhood, with smart, slightly snarky takes on branding and culture. Their readers showed up because they loved that voice, and instead of trying to be two different people, we just decided to be slightly louder together. The result: a community that’s smarter, funnier, and more willing to call brand nonsense by name.
It also makes Stupidpreneur the world’s biggest newsletter in the branding space right now. That feels wild, so I’ll say it again: the world’s biggest branding newsletter.
Thanks for showing up.
Here’s what I learned scaling from 10k to 20k in 18 days
Acquisition beats optimization when the audience is the right fit. You can spend months tweaking subject lines. Or you can find an audience that already loves the kind of stuff you do and bring them in. Both matter, but fit matters more.
Tone is a moat. People subscribe because they believe you will say the thing they wish they’d said. Keep being a person, not a brand chatbot.
Community > vanity metrics. Engagement, replies, and real conversations are where the real value hides.
What this means for you
More of the stuff you already like. More case studies that actually mess with your brain. More experiments where we try strange things and report back about what worked and what blew up. Now with extra Stupidpreneur energy. I promise fewer polished marketing slides and more honest playbooks you can steal and slightly ruin for your own purposes.
What I want from you
If you’ve been reading for a while, hit reply and tell me which piece changed how you think about branding. If you’re new, welcome. Come! Say hi and tell me what brand made you buy something you didn’t need. I read every reply when I can, and they keep this thing human.
One last non-squeezed-in reminder: this is not an end point. It’s a checkpoint that tells us we’re onto something worth building. Thank you for subscribing, forwarding, arguing in the comments, and occasionally making fun of my analogies. Let’s double down on useful, weird, and occasionally brutal branding thinking.
P.S.
If you run a newsletter or a tiny publication and you’re thinking about a partnership or a merge, I’m honestly open to talking. Send a note. No slide decks required.