Start Here: A Guide to 100 Founders
If you just subscribed—welcome. If you’ve been here a while and the email-by-email cadence has buried what you’re actually looking for, this page is for you.
100 Founders distills what I’ve learned from 250+ tech founders running sales themselves. The thesis in one line: founder-led sales works—until it doesn’t. Most of what’s published here is about recognizing where you are in that arc, and what to do next.
Below are the six themes the writing comes back to, with a few starting points for each.
Founder-Led Sales 101 (start here) What it actually is, why it works at first, and the predictable moments it stops working. Start here if you’re new. → Founder-Led Sales: What It Is, When It Works, and When It... → The 7 Hardest Moments in Founder-Led Sales → Magicians vs. Soldiers: Why Founder-Led Sales Breaks at Scale
Positioning & ICP The single highest-leverage work most founders avoid. Tightening who you’re for, what you stand for, and why it matters more than your product. → Big TAM Is Not Ambition. It’s Avoidance → The Sea of Sameness: How B2B Founders Stand Out → Being “Better” Is No Longer Product-Market Fit
Pipeline & Deal Mechanics What’s actually happening inside your pipeline—why deals stall, what real momentum looks like, and the signals founders consistently misread. → SPRINT: Why Founder-Led Deals Stall Right When They Should Close → Curiosity vs. Purchase Intent: How to Tell If a B2B Prospect Will Actually Buy → Sales Activity vs Progress: The Pipeline Paradox in B2B SaaS
Building Your Sales Team The transition off founder-led is where most companies stumble. When to make the first hire, what a Founding AE looks like, and why the same patterns of failure keep showing up. → The First Sales Hire Almost Always Fails for the Same Reason → When You’re Ready for a Founding AE → The “First Sales Hire” Trap
Founder Strategy & Pressure The forces shaping every selling decision—fundraising timelines, pricing anxiety, communication gaps, and the mindset traps founders fall into. → Drink Your Own Champagne → Fundraising Pressure Is Quietly Wrecking Strategy → What’s Really Holding Founders Back?
Tool Spotlights & Reports Deeper dives on vendors solving real founder-led sales problems, plus quarterly synthesis reports across hundreds of founder conversations. → Q3 2025: Insights from 100 Founder Conversations → The Founder Led Sales SPRINT → Fixing the Broken B2B Buying Experience with Salespeak AI
If you’re not sure where to start, read Drink Your Own Champagne first. It’s the most-read piece here and a fair sample of what to expect.
New posts go out every Saturday. Reply to any email. I read everything.
—Dave