Your Next Outage is a Moat Test
Cloudflare's global outage wasn't a failure, but a test of its market strength. Learn how transparency can deepen trust and solidify your business's 'moat'.
Cloudflare: Leading Cybersecurity [Business Breakdownes Ep 241]Cloudflare Final
With Matt Russell, Sam Eden · Sunday, February 8, 2026
This episode delves into Cloudflare, the cybersecurity giant, exploring its history, business model, and strategic evolution. Matt Russell and guest Sam Eden break down Cloudflare's core web security services, its expansion into corporate 'zero trust' cybersecurity, and its developer platform, including its role in the burgeoning AI inference market. They also cover its financial performance, competitive landscape, and the impact of its recent global outage.
Key takeaways
- Cloudflare has established an unassailable lead in its foundational web security business due to its massive, unique network. Read more →
- Cloudflare shifted from serving small premium customers via product-led growth to targeting large enterprises with direct sales. Read more →
- Software companies operating their own global infrastructure have lower non-GAAP gross margins than typical SaaS firms due to depreciation costs. Read more →
- Cloudflare's 'Act 3' pushes serverless functions (Workers) to the network's edge, attracting developers with a generous free tier. Read more →
4 articles from this episode
Cloudflare's Enterprise Sales: Pool of Funds & Reps
Cloudflare moved from PLG to enterprise sales. Learn how their 'pool of funds' strategy and sales leadership hire transformed growth. Actionable advice for founders.
Cloudflare's Margins Expose Hidden Infrastructure Costs
Ambitious builders: Cloudflare's financials reveal that 'software margins' often hide substantial infrastructure costs and capex. Model your business beyond growth.
Cloudflare's Edge AI: Why Your Next Model Should Go There
Cloudflare Workers now offer AI inference at the network edge, cutting costs and latency. Leverage this for your next AI-native product prototype.
More Invest Like the Best episodes
- Affirm: The Next American Express (Audio)Oct 25 · 5 articles
- The Nvidia of Physical AI: Inside Applied Intuition's $15B BusinessAug 2 · 3 articles
- "The OpEx Was Just Honestly Stupid" — Kaz Nejatian on What He Found Inside OpendoorMay 10 · 2 articles