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  1. This Week in Startups
  2. A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312
A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312

This Week in Startups · Jul 15, 2026

VCs discuss Stripe's bold bid for PayPal, AI's role in corporate culture, building defensible startups, and the coming wave of consumer tech.

Staying Private Gives Unicorns Like Stripe "YOLO" Flexibility for Megadeals

Private companies like Stripe can make massive, long-term acquisitions without the immediate scrutiny and short-term stock price impact they would face as a public company. This allows for bolder, more strategic moves.

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312 thumbnail

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312

This Week in Startups·2 months ago

Pre-Seed AI Startups Should Ignore Custom Evals and Focus on Product-Market Fit

Building custom AI model evaluations is a late-stage concern for creating defensibility. For pre-seed startups, it's a distraction. The only goal is achieving product-market fit using the cheapest, most accessible models, whether that's OpenAI, Anthropic, or open-source alternatives.

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312 thumbnail

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312

This Week in Startups·2 months ago

Tech Giants Stagnate When a 'Professional MBA' Culture Replaces Innovation

Companies like PayPal decline when their culture shifts from innovating and breaking things to one of professionalization. When employees focus more on internal promotions than product, the company calcifies and becomes an acquisition target.

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312 thumbnail

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312

This Week in Startups·2 months ago

Managing Secondary Markets Is So Painful It's a Reason to Go Public

Contrary to popular belief, staying private isn't always easier. The administrative burden of managing secondary share sales and controlling who gets on the cap table is a significant headache for CEOs, making an IPO an attractive solution for simplicity and control.

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312 thumbnail

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312

This Week in Startups·2 months ago

VCs Win Deals by Building Simple Demos with a Startup's Own Product

Instead of just reading a deck, VCs gain a competitive edge by using a startup's developer tools to build a simple demo. This hands-on approach, which can take minutes with AI coding tools, deeply impresses founders and can secure an allocation in a competitive round.

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312 thumbnail

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312

This Week in Startups·2 months ago

VCs Invest Outside Silicon Valley to Escape the 'Fast Follower' Effect

The density of information in Silicon Valley leads to a 'fast follower' effect where successful ideas are immediately copied. VCs are investing in other geographies to find startups in less crowded, often harder-to-build categories (hardware, regulated industries) with more durable competitive advantages.

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312 thumbnail

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312

This Week in Startups·2 months ago

AI Leaders' Early Doomerism Made Gaining Public and Government Support Harder

The AI industry inadvertently created a public relations problem. Early, scary rhetoric about job loss and existential risk from leaders at firms like Anthropic has poisoned the well, making the public and politicians more fearful and less supportive of AI advancement.

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312 thumbnail

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312

This Week in Startups·2 months ago

Crypto's Focus Has Shifted From DAOs to 'Boring' Institutional Finance

The revolutionary zeal in crypto, exemplified by DAOs, has faded. The real, albeit less exciting, progress is now in institutional use cases like tokenizing real-world assets and creating stablecoins for large banks and fintechs, rather than societal transformation.

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312 thumbnail

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312

This Week in Startups·2 months ago

Individual Employees, Not Just Companies, Must 'Burn the Boats' in the AI Era

Surviving the AI transition requires more than a company-level pivot. Every individual employee must proactively "burn the boats" on their old job descriptions and skill sets, racing to learn new AI tools and become AI-native within their roles to stay relevant.

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312 thumbnail

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312

This Week in Startups·2 months ago

Foundation Models' Real Threat Isn't Data Scraping, It's Metadata Analysis

Startups using large AI models shouldn't just worry about their data being used for training. The subtle risk is the *metadata*—like the frequency and type of tool calls—which can reveal a startup's growth, strategy, and product direction to the model provider.

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312 thumbnail

A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312

This Week in Startups·2 months ago