David Cummings on Startups

David Cummings on Startups

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Daily reflections on SaaS, leadership, and company‑building from Pardot’s founder.

The First Five Questions to Ask After a Startup Pitch
NewsApr 4, 2026

The First Five Questions to Ask After a Startup Pitch

The article outlines five critical questions to ask after hearing a startup pitch, emphasizing timing, founder motivation, product superiority, founder fit, and focus. It argues that being slightly early allows a venture to capture market share once demand matures, while...

By David Cummings on Startups
The Second Time Around: Why Founders Come Back
NewsMar 28, 2026

The Second Time Around: Why Founders Come Back

Second-round entrepreneurs return to the same market after an exit or non‑compete, driven by three recurring themes: improved market timing, unfinished business, and deep industry familiarity. Their first venture often arrives three to five years before the market fully matures,...

By David Cummings on Startups
8 Moats for Sustainable Software Companies
NewsMar 21, 2026

8 Moats for Sustainable Software Companies

Investor Gokul Rajaram outlined eight strategic moats that can make software companies sustainable, ranging from proprietary data to physical infrastructure. He argued that each moat requires significant time and capital to build, and that firms securing four or more are...

By David Cummings on Startups
Product Value vs Product Distribution in the Early Days
NewsMar 14, 2026

Product Value vs Product Distribution in the Early Days

Entrepreneurs often wrestle with whether to chase customers quickly or perfect their offering first. The author argues that in the early stages, product value should dominate, especially when the solution is unproven. A must‑have, revenue‑impacting product reduces churn and builds...

By David Cummings on Startups
Every Bit of Effort Helps
NewsMar 7, 2026

Every Bit of Effort Helps

The article reminds entrepreneurs that every small action—another meeting, call, or feature—adds up to meaningful progress. It stresses the importance of relentless effort, even when breakthroughs seem distant, and highlights the value of peer groups for accountability and shared experience....

By David Cummings on Startups
15 Angel Investments and All Failures
NewsFeb 28, 2026

15 Angel Investments and All Failures

A seasoned angel disclosed that all 15 of his investments have gone to zero, underscoring the brutal failure rate of early‑stage startups. While diversification is a common mantra, statistics show that a sizable share of startups never reach meaningful revenue,...

By David Cummings on Startups
Seven Reasons SaaS Valuations Are Crumbling in the Age of AI
NewsFeb 7, 2026

Seven Reasons SaaS Valuations Are Crumbling in the Age of AI

SaaS valuations have slumped from seven‑to‑eight times revenue to roughly three‑to‑four times as AI tools reshape the sector. AI‑driven coding lets companies replace legacy SaaS with custom apps, eroding lock‑in and pressuring per‑seat pricing. Long‑term revenue durability is questioned, entry...

By David Cummings on Startups