Why Founders Shouldn't Write Their Own Newsletter

You're already working 70-hour weeks. Product development, fundraising, hiring, customer calls, and the daily fires that come with building a company. Now someone tells you that you need to start a newsletter too.

So you think, "How hard could it be?" You set up a Substack, write an ambitious first post, maybe even a second one. Then reality hits. Week three arrives with a product crisis, a key hire falling through, and a board meeting to prep for. The newsletter gets pushed to next week. Then the week after that.

Here's the thing: that silence isn't neutral. Every missed week is a visible signal that something more important came up. Again. Instead of building trust, you're broadcasting inconsistency.

The Newsletter Reality Check

What are you actually signing up for? A decent 800-word newsletter takes 3-5 hours when you factor in planning, writing, editing, and getting it right. That's half a workday. Every single week.

Most founders I know can barely keep up with their investor updates, let alone public content. They start strong, then the gaps appear. First, it's every other week, then monthly, then radio silence. I've watched this pattern dozens of times.

The worst part? Your audience notices every gap. Investors see the inconsistency. Potential hires see the abandoned communication. Customers see a founder who can't maintain basic follow-through.

Why Newsletters Actually Matter for Founders

Here's what most people miss about founder newsletters: they're not content marketing. They're owned media that builds trust at three levels simultaneously.

• Investors see leadership clarity. Regular updates showing progress, strategic thinking, and how you handle problems demonstrate the kind of founder they want to back. Sahil Lavingia at Gumroad shares everything: revenue numbers, strategic pivots, and even personal struggles. The result? Investor confidence through multiple business model changes.

• Talent sees authentic culture. The best employees want to work for companies they understand and believe in. Your newsletter becomes a recruitment tool that pre-qualifies candidates who connect with your mission. Buffer's founders shared detailed revenue dashboards, failed experiments, and hiring processes. This transparency didn't hurt them: it became their competitive advantage for attracting principled employees.

• Customers see confidence in your direction. When you share your building process openly, you signal confidence in where you're headed. Customers buy from companies they trust, and trust comes from understanding the thinking behind the product.

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