TLDR FOUNDERS 2026-03-25

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REVENUE DURABILITY IS FAILING IN THE AGE OF AI

Every VC, PE firm, and public market investor is circling the same question in 2026: Is this company's revenue actually durable? The answer is crushing valuations, freezing M&A, and making fundraising brutal. Bill.com dropped from 90% growth to 12%. Snowflake fell from 73% to 26%. The uncomfortable truth is that nobody has real confidence that software revenue will hold up over the next decade, and that uncertainty alone is enough to reshape how every founder thinks about pricing, retention, and defensibility.

WHY FREE TRIALS DON'T MAKE SENSE ANYMORE (AND WHAT USER ACQUISITION TACTIC TO TRY INSTEAD)

AI-driven costs, shorter payback expectations, and web funnels are causing free trials to decline as companies push for faster monetization. Short trials now dominate despite lower conversion. Use paid trials and trial qualifier events to improve signal quality. They filter for high-intent users, enabling more effective UA optimization while maintaining sufficient event volume for ad networks.

I WANTED TO BUILD A VERTICAL SAAS FOR PEST CONTROL. I TOOK A TECHNICIAN JOB INSTEAD

Taking a job in an industry you want to get into is a good way to figure out what problems the industry faces. Terry Clarke wanted to build a vertical SaaS for pest control, so he applied for jobs, got licensed, and started documenting all the issues he faced in his role. He moved about the company he worked in to learn more about how it worked, and eventually left the company to start his own. The experience helped him learn what tooling to build for his platform.

HOW TO BUILD A PMF MACHINE

Start with a metric, then build the feature. Rank your ideas according to which of them has the highest probability of moving the metric. Estimate how much effort each idea would take to realize. You can then see which tasks are high-impact and low effort. Constantly revise roadmaps to avoid wasting engineering time, and measure everything to calibrate better.

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SOFTWARE ENGINEERING CALORIES: WHAT WOULD CAL.AI SAY ABOUT YOUR PRODUCT?

Founders should treat their products like their bodies. We gain weight if we eat more calories than we burn, and lose weight if we burn more calories than we eat. For software, the input is code, and the output is feature adoption. Some products would genuinely be better if half their features were deleted. More weight should mean more strength.

THERE ARE ONLY TWO PATHS LEFT FOR SOFTWARE

Software companies face two paths to survive market pressure: accelerate growth through new AI-native products or achieve over 40% operating margins, including stock compensation. CEOs need to decisively select a path, restructure leadership, and either innovate with high-growth AI products or refocus on profitability through higher efficiency and pricing. Choosing neither and staying in the middle will lead to growth pressure and diminished market value.

AI DIDN'T KILL PRODUCT INTUITION. IT EXPOSED WHO NEVER HAD IT

Real product intuition is knowing which ideas are fragile before investing in them.

HOW MONEY FLOWS

A mental model for why some startups raise millions while others get ignored - capital flows like water toward the biggest, most painful problems.

HOW TO MAKE SOMETHING GREAT

Greatness is not about one-shotting perfection - it is the compound interest of iteration, curiosity, and caring more than anyone else.

WHY BETTER SIGNALS DRIVE PAID SEARCH PERFORMANCE

WHAT WE WISH WE KNEW ABOUT BUILDING AI AGENTS

Knowing these things would have helped PostHog launch months earlier, provide a better early experience to users, and make progress on capabilities faster.