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STARTUP PUNDITRY'S 25 YEARS OF FAILURE

Startup methodologies widely adopted over the past 25 years have not increased startup success rates, as shown by unchanged survival rates in government data.

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THE MARGINAL COST OF ENTREPRENEURSHIP IS TRENDING TOWARDS ZERO

Shopify is increasingly becoming the core infrastructure for modern commerce. The platform dramatically reduces the barriers to starting a business by unifying payments, logistics, and software. The company is embedding AI directly into its entrepreneur stack to lower the time and labor required to build and run a company. Shopify is making entrepreneurship increasingly frictionless, and the data reflects it.

HOW MUCH OF THE SOFTWARE SLOWDOWN IS JUST BUDGETS FLOWING TO ANTHROPIC AND OPENAI? MAYBE AS MUCH AS 70%

Almost every major public software company has printed lower growth rates every single year since the 2021 peak. The conventional explanation is that vibe coding is eating software, but what's actually happening is simpler and more damaging: companies have finite budgets, and they're pouring an unprecedented share of those budgets into AI infrastructure and foundation model providers. The software budget pool is now shared with a new category that went from zero to over $40 billion in two years. This structural rebalancing will take several years to sort itself out, and it is going to hurt a lot of software companies before it does.

WHY THE WORLD STILL RUNS ON SAP

Upgrading from SAP ECC to S4HANA costs $700M, takes 3 years, and requires a team of 50 from Accenture. Lidl scrapped its transition after blowing $500M. Workers toggle between apps ~1,200 times per day, and 47% can't find the information they need. Startups like Axiamatic, Conduct, and Tessera are wrapping legacy systems in AI instead of replacing them, targeting the $380B system integration market.

WHY FOUNDERS CAN'T DELEGATE STORYTELLING

Storytelling is strategy, and the founder is the only person who holds the full context: why the company started, which experiments failed, what those failures taught, and where the company is heading. When storytelling gets delegated, marketing, sales, and product each fill in the gaps with their best guesses, creating subtle misalignment that compounds across every function until customers are closed on the wrong story and the product builds toward the wrong vision.

THE MOST UNDERRATED HIRE RIGHT NOW IS A GREAT PRODUCT PERSON

When building was hard, engineering was the bottleneck, and the status hierarchy reflected that. Now that building is easy, the variance in outcomes has shifted almost entirely to judgment on what to build, how to sequence it, and how to talk about it. The rarest version of this hire sits at the intersection of culture and deep technology, genuinely bilingual between what is technically possible and which cultural currents are real versus ephemeral.

SHOW CUSTOMERS THEIR WINS

Retention is half a perception problem - customers don't churn because they stopped getting value, they churn because they stopped noticing it. The fix starts on day one by cementing their "before" state so every improvement has a visible benchmark. Rilla went from $0 to $70M ARR in 7 years as the 7th fastest-growing SaaS company, built entirely on consumer tactics like streaks and goals that most B2B companies ignore.

REFGROW

Launch affiliate and referral programs in minutes.

KIPPS AI

AI agents for lead qualification and outreach.

OPENVIKTOR

Open-source AI employee that lives in Slack.

SPENDING OTHER PEOPLE'S TIME

Asking for someone's time is virtually free for the asker, yet enormously expensive for the person being asked. The trade is asymmetric, with the askee having to rebuild whatever mental state they were in before the interruption, while the asker just gets on with their day. The problem compounds with AI as people are effectively shifting their 'productivity' onto other people's shoulders. Organizations need to make these costs visible and put friction in the right places so that the default path protects attention instead of consuming it.

THE COLLAPSE OF TERMINAL VALUE - WHAT HAPPENS IF AI MAKES EVERY MOAT TEMPORARY?

$58 trillion in S&P 500 market cap repriced at 5x free cash flow instead of today's 20x means a 75% drawdown - roughly $44 trillion evaporating. That's the math if AI makes every competitive moat temporary instead of durable. Newspapers went from 12-15x EBITDA to 2-4x in a decade, retail followed, and taxi medallions went to zero. The $300-500B/year in AI capex only pencils out if returns are durable, but AI itself is the thing making returns short-lived.

25-28% OF TWO-FOUNDER STARTUPS LOSE A COFOUNDER BY YEAR FOUR

Data from 18,920 US startups on Carta shows 25-28% of two-founder teams lose a cofounder by year four.

WHY AND HOW TO BUILD A RESEARCH ORG

This is the moment for concentrated research ambition in every vertical.

YOU ARE RESPONSIBLE FOR YOUR AGENT

Companies are liable for the actions of employees' personal AI agents, akin to past challenges with personal devices.

Replit

AI WON'T REPLACE INNOVATION

History suggests that the future of AI will look less like a monopoly and more like an ecosystem. Frontier labs will build the infrastructure while thousands of companies emerge to turn that intelligence into products, workflows, and systems that solve real problems. Completely new jobs will likely be created. Founders and startups that are willing to deeply understand customers, build thoughtful systems, and focus relentlessly on specific workflows will see more opportunity than ever.

DATA IS THE ONLY MOAT

Think about the metadata you collect when people use your platform or when you observe the consequences of using your product. For example, the times when people post from social media share links, when most people engage, or what kind of content drives the most engagement. This data is your most unique data moat. Use it to improve how people use your product and how they run their own businesses.

RETHINKING SAAS METRICS FOR AI

If you're still tracking ARR as your north star, it's lying to you. AI-native companies need different metrics - token consumption is the one that's hard to fake because the fastest-growing companies sit directly in the token path. Raw tokens don't tell you if you're creating value or just passing through infrastructure costs, so gross profit per million tokens is becoming the real scorecard investors are pricing companies on. DAUs stop mattering when AI agents are doing the work inside other products via MCP, and nobody trusts the LTV of any AI product right now.

HOW TO THOUGHT LEAD (2026)

Earn mindshare for your topic by regularly posting information, products, and mental models to be used by others. Thought leadership boils down to six principles, ordered explicitly in descending order of importance: have credibility; know what people aspire to; be authoritative, knowledgeable, and useful; be quoteable; be strongly opinionated; and be first, or be funny. This post looks deeper into these principles to provide a formula for thought leadership. The best thought leaders do the work first, earn credibility, and then let everything amplify a foundation that's already solid.

DEVELOPER RELATIONS: WHAT IT IS, AND HOW TO MEASURE IT

DevRel is such a flexible and multifaceted role that it means very different things depending on what company you're at. The role has five primary facets: documentation, engineering, content and events, product feedback, and community management. This article talks about each facet, what they mean in practice, and why they sit where they do in the stack ranking.

reach.

NAOMA AI

AI video agent that runs live product demos 24/7.

STRUCT

Root-cause engineering alerts from logs and traces.

PRAVA

Payments stack built for AI agents.

WIZ HAD 4 CO-FOUNDERS. DATABRICKS AND ANTHROPIC HAVE 7. STOP OVERTHINKING IT

Don't try to find the right number of co-founders. Co-founders who just met a month ago are a risk. Founding team trust matters infinitely more than founding team structure. Having the right team to make the pie big is worth more than having a larger slice of a smaller pie.

VENTURE CAPITAL DOESN'T EXIST

What we call 'venture capital' is a conflation of seed stage investing, traditional venture, supercharged growth investing, and previously small-cap growth tech stocks. The more the individual parts are acknowledged, the better off everyone will be. Large capital providers can still deploy capital to all four types of investing. However, founders and funders need to be aware of what game they're playing - the reality is that most genuinely don't know.

SELLING YOUR COMPANY

Confident buyers won't mind if you talk to other bidders because they know they're the better outcome for your business if you want to sell it.

HOW TO GIVE A DEMO THAT DOESN'T SUCK

Most demos are 45 minutes of monologued clicking through every feature while the prospect zones out.

STARTUPS SHOULD EVALUATE ENGINEERS DIFFERENTLY FROM BIG COMPANIES

A founder hired a FAANG backend engineer who aced every interview.

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FINTECH'S MOATS DON'T COMPILE

Fintech's primary moats reside in regulatory permissions, credit data, and risk-bearing capacity rather than replicable software code. While AI compresses margins for pure SaaS by commoditizing code, it strengthens fintechs that own their licenses and underwriting history. Competitive advantage is shifting away from UI toward those who control the "fin" side by managing money movement and proprietary risk models that AI optimizes but cannot replace.

MANAGEMENT IN THE AGE OF AI

Managers must be builders in 2026 because not building now is the bigger waste of time. They need to learn AI tools, and building is often the most efficient path for the team. The ability to build will be a key differentiator between teams that win and teams that drown in their own output. The gap between good management and bad management is now a lot wider.

BUILDING WHERE THE BUYERS ARE

For the last twenty years, the hardest part of building a tech company was the development itself. AI is dissolving that constraint. Companies no longer need to have large teams to ship products. This means Silicon Valley may no longer be the center of the tech industry. Companies needed to be near the engineers when the hard part was writing code, but they will now move to where the buyers actually are.

HOW YOU SOURCE GREAT DESIGNERS

If you want the best designers, you have to go where they are and be someone they want to talk to. X is a good platform for designers who are exploring startup opportunities. Look for designers who actively follow tools and communities that signal taste. Most self-aware designers move quietly through trusted networks. Founders need to be plugged into those networks before they need them.

BEN HOROWITZ ON WHAT MAKES THE BEST FUNDRAISING PITCH

The fundamentals haven't changed nearly as much as people think. Strategy is still about articulating a clear 'why'. Product management is still about shipping the right product at the right time. The best fundraising pitch is the one you actually believe. The landscape around the fundamentals has changed, but there are still massive new opportunities hiding in plain sight.

THE NEW GTM PLAYBOOK: OUTBOUND ALONE WON'T CUT IT

AI has commoditized cold outreach, forcing a shift from outbound-only tactics to a multi-channel flywheel of content, community, and retargeting. ColdIQ nearly doubled revenue by using content to prime prospects, resulting in conversion rates 3x higher than traditional cold contacts. Success in 2026 requires building this organic distribution early, as the 6-12 month startup time creates a massive lead over competitors still relying on saturated outbound channels.

HOW POSTHOG BUILT A MARKETING ENGINE THAT ACTUALLY DRIVES GROWTH

Tens of millions in ARR, $1.4B valuation, zero outbound sales calls ever. Usage-based pricing with a generous free tier means one engineer installs it for a side project and it spreads inside the company the way Figma did. Their newsletter has 75K subscribers and never mentions PostHog - just teaches engineers how to build better products.

FISH AUDIO

Expressive text-to-speech and voice cloning platform.

NOTTE

Turn any website into a callable API.

FIGR

Spot UX blind spots before writing code.

STRATEGIC CHOICES: WHEN BOTH OPTIONS ARE GOOD

"Customer-first" isn't a strategy - nobody picks "customer-last." Real strategy means choosing between two good options where smart companies exist on both sides. "All-in-one" means you personally own every feature request forever. "Infinitely extensible" means your UX becomes a patchwork quilt. If the opposite of your strategy sounds stupid, you haven't decided anything.

REVENUE ADDICTION KILLS COMPANIES

If revenue is your North Star, your company is destined to die. Revenue-addicted companies kill every initiative that doesn't move the number this quarter, which is exactly the opposite of what you need during the AI transition when you have to make big product bets. Lovable swapped its North Star to daily active apps and built a qualitative "Lovable Score" combining NPS, PMF score, effort score, and CSAT. Revenue still matters, but it's the output of the system, not the thing you optimize for.

PRODUCTIVE INDIVIDUALS DON'T MAKE PRODUCTIVE FIRMS

Individual AI gains often create organizational chaos and "slop" rather than firm-level value, mirroring the 30-year lag in productivity seen during factory electrification.