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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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TOBIRA.AI

Network where AI agents connect and negotiate deals on behalf of users.

REMIX

Turn your raw ideas into content with parallel AI agents.

LITTLEBIRD

AI assistant that knows what you're working on.

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.

THE GREAT CIRCLE OF LIFE

Every major technology era follows the same arc - consumer first, then enterprise, then infrastructure - and AI is no exception. The first wave of winners built directly for consumers, but the pattern from prior eras says the durable businesses will be the ones building tooling and infrastructure layers underneath. If you have seen this cycle before, the playbook is clear: the picks-and-shovels companies outlast the gold rushers. Recognizing where you sit in this arc shapes when to enter, who to build for, and how to time your raise.

I ANALYZED ALL YC W26 COMPANIES: HERE'S WHAT IT TELLS US ABOUT THE FUTURE

85% of YC's W26 batch is AI-first, with 56 of 198 companies building fully autonomous agents explicitly positioned as AI employees targeting every $50-150K knowledge worker role, from AI accountants closing books without human touch to AI law firms staffed entirely by models. Healthcare is the largest vertical with 22 companies going after clinical work itself rather than EHR wrappers, while 13 robotics companies are actively deploying alongside a full picks-and-shovels ecosystem for physical AI.

TO THRIVE TODAY, YOU HAVE TO BECOME AN AGENTIC DEPLOYMENT EXPERT. BUT SO, SO FEW ACTUALLY ARE

Companies no longer need engineers to win. They need someone who treats deployment as a core job function - an agentic deployment expert. These hires are worth more than anyone else you can hire right now. They don't need to be technical, they just have to know how to use AI tools to get to deployment. Companies that don't hire an agentic deployment expert risk wasting years of work.

THE PSYCHOLOGY BEHIND VIRAL LINKEDIN CONTENT

Posting times, hashtag counts, and emojis have almost nothing to do with LinkedIn virality - emotional architecture does. The gap between posts that explode and posts that die in silence comes down to how the information makes people feel, not what information is being shared. Think identity validation, status signaling, and tribal belonging baked into every sentence. One company went from crickets for 8 months to booking 96 calls in a single month after rebuilding content around emotional psychology instead of information delivery. Spend less time on the insight and more time engineering the feeling.

HOW TO BUILD A REAL OPERATING PLAN: INSIDE A FULLY LINKED STARTUP FP&A MODEL

Revenue and bank balance stop being enough the moment an investor or board member asks a hard question. A fully linked FP&A model connects revenue forecasts to hiring plans, burn rate, and fundraising timelines in a single living document - change one input and every downstream assumption updates automatically. This is what lets you stress-test scenarios like a churn spike or a delayed round before they actually happen. It is also the kind of financial infrastructure sophisticated investors expect to see when you are defending your raise.

HOW TO VET A COFOUNDER

To vet a co-founder, work directly with them on a real project to gauge compatibility and efficiency authentically. Lay the groundwork for collaboration by evaluating past outputs, seeking references, and discussing values to identify potential long-term challenges or alignments. Avoid superficial interviews, and prioritize genuine trials to make informed decisions about meaningful partnerships.

SUPERMEMORY

Supermemory is an agent memory system that achieves ~99% SOTA accuracy.

FRACTAL

Build, test, and deploy ChatGPT apps.

THE BESPOKE SOFTWARE REVOLUTION? I'M NOT BUYING IT

Most people don't like computers and only tolerate them because they have to. They likely would rather not think about them at all, given the choice. These people might use AI, but they won't be using the technology to build their own systems and tools to maintain. They just want to get the task done.

1:1S ARE BEING RUN WRONG

Status update 1:1s are a waste of everyone's time, and the fix is simpler than you think. The shift that matters is moving from "what did you do this week" to questions that uncover blockers, ambitions, and candid feedback - the things people will not volunteer in a group setting. A well-run 1:1 builds trust, surfaces problems weeks before they escalate, and develops your team in ways that compound as you scale. Getting this cadence right early creates a management culture that becomes a genuine competitive advantage.

VIBECODING IS SELF-EXPRESSION

Vibecoding has quietly turned software creation into a creative act, and that shift puts a large class of consumer utilities on shaky ground.

YOUR NOTES ARE THE MOAT

A field report on the convergence happening across personal knowledge tools in March 2026.

THE COLD START TRAP: WHY THE BEST SOCIAL INFRASTRUCTURE ALMOST NEVER SUCCEEDS

The "cold start" trap hinders promising social infrastructure by requiring mass initial adoption for value, causing most projects to fail.

SCALE IS A TACTIC, NOT A VIRTUE

Silicon Valley treats scale like a moral good when it's actually just a strategic choice.

THE END OF FRAGMENTATION

Many people think that AI will fragment markets because the technology makes it easier to create software, which means new companies will be built to serve every niche use case. AI will allow clones of major tech companies to emerge to carve out market share. However, it is more likely that AI will drive greater concentration of value into fewer companies and create the biggest businesses of all time. History teaches us that new technology leads to more concentration, and AI has the potential to be the most powerful example of this yet.

THE PARASITE FALLACY

Being a system of record is no longer enough in the age of agents. The value is quickly shifting to the 'system of action'. Databases are cost centers, whereas agents that can complete tasks are value multipliers. Companies that focus on how to tax the consumption of their data rather than how to enable better actions become more of a utility than a platform. The goal should be to create value by being the best place to execute.

I'VE SPENT OVER $1M ON TECH LAUNCHES IN THE PAST YEAR. HERE'S EVERYTHING I KNOW

Startups burned over $100 million on launch campaigns last year. 86% of those videos didn't crack 50,000 views. This post contains a detailed tutorial on how to engineer trending videos from the first frame to the last repost. The author's team has spent over a million dollars orchestrating launch campaigns on X over the past year, achieving an average of 1.5 million views per video.

WHY PILOTS MATTER MORE THAN YOU THINK—AND HOW TO RUN THEM RIGHT

Pilots are opportunities. When structured intentionally, they can be a powerful tool in sales motion. Pilots accelerate trust, demonstrate value, and lay the groundwork for long-term partnerships. The key is to be clear and intentional, and to keep momentum high. Getting the pilot motion right will result in a far more predictable sales process and a clearer path to scalable revenue.

GUILLERMO RAUCH'S 5 LESSONS FOR FOUNDERS BUILDING IN THE AI ERA

Open source stress-tests product market fit, as people won't pay for something they won't use for free. You need a bold, boundless mission, but be focused in what you are building. AI makes it even more important to be mindful when choosing what problems deserve your attention. Choosing what to dismiss is a competitive advantage. Hire people who are on the rise rather than people who've already made it.

BUILD SAAS WITH STRONG OPINIONS

SaaS founders should throw out the old 'configure it all' mentality and do the hard work of figuring out what works best, then sell that as a strongly opinionated piece of software. Businesses will increasingly pay to shortcut their way to best practice rather than buy the tools to do it themselves. This will allow them to focus on their unique value and not waste time reinventing the same sales pipeline used by everyone else. Companies that combine services and software will have a unique advantage.

LIGHTFIELD

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BANYAN AI LITE

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TERMINAL USE

All-in-one hosting infrastructure for long-running agents.

SIZE OF THE PRIZE AND RUN THE DISTANCE

Nvidia took 3 decades to reach $1T but just 2 years to go from $1T to $5T. At 10% annual compounding, $10T is next. The investing variable that founders and investors consistently get wrong is the size of the prize - nobody imagined Airbnb, DoorDash, or Uber becoming what they are. An outlier founding team can compound a seed into $10B, then $100B in two decades, then $1T in three.

MICRO-APP PORTFOLIOS - 5% HIT RATE, VIBE-CODED EXITS, PORTFOLIO OS

One solo founder launched 70+ projects with zero employees and hit $3.1M ARR. The playbook is portfolio theory applied to startups - ship fast, kill fast, let a 5% hit rate cover the failures. Vibe coding tools like Lovable ($100M ARR in 8 months, $6.6B valuation) and Bolt.new ($40M ARR in 6 months) make the math work by collapsing build time from months to days. A $20-50/app/mo maintenance layer turns the portfolio's biggest liability into recurring revenue.

TECHNICAL LEADERS MAKE THESE 4 COMMON STORYTELLING MISTAKES

Every time you say "well, technically..." you're about to kill a good story. The mistakes that tank most founder pitches all come from the same place - treating all details as equally important. Your audience doesn't want comprehensive, they want compelling. Short anecdotes of 5-15 seconds land better than any 12-step hero's journey, and the hook that gets someone in the door is never the same thing that gets them to stay.

THE MONOCULTURE OF STARTUP METHODS

The widespread adoption of similar startup methodologies fosters mediocrity.

THE ILLUSION OF SPEED - WHY AI IS MAKING TEAMS FASTER BUT NOT BETTER

Your engineering team is shipping more code than ever, but none of the metrics that actually matter are moving.