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  1. This Week in Startups
  2. Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210
Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210

This Week in Startups · Nov 18, 2025

Jeff Bezos returns as co-CEO of a $6.2B AI startup. Jason discusses global tech hubs, Ramp's valuation soars, and a Waymo incident sparks debate.

Decode Stealth Startups By Analyzing Their Leaked 'Comps'

Strategic leaks of "comparable companies" to media outlets are a key tool for stealth startups to signal their direction. Analysts can reverse-engineer a company's strategy, target market, and talent focus by scrutinizing these chosen comps. This turns PR into a powerful source of competitive intelligence.

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210 thumbnail

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210

This Week in Startups·3 months ago

In a Momentum Market, Hyper-Growth Startups Should Always Be Raising

For startups experiencing hyper-growth, the optimal strategy is to raise capital aggressively and frequently—even multiple times a year—regardless of current cash reserves. This builds a war chest, solidifies a high valuation based on momentum, and effectively starves less explosive competitors of investor attention and capital.

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210 thumbnail

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210

This Week in Startups·3 months ago

The Inevitable Pipeline from Remote Work to AI Automation

A powerful mental model for the future of work is a three-step pipeline. If a job can be done remotely in a high-cost country, it can be offshored to a low-cost one. Once offshored and process-driven, it becomes a prime target for AI automation. This positions remote work as a transitional phase, not an endpoint.

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210 thumbnail

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210

This Week in Startups·3 months ago

Startup Education Must Adapt to Local Market Weaknesses

A successful startup curriculum can't be one-size-fits-all globally. It requires real-time adaptation to address specific local ecosystem gaps, such as a need for better design skills in the Middle East or a push for global-facing products in an otherwise mature, domestic-focused market like Japan.

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210 thumbnail

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210

This Week in Startups·3 months ago

The 'Quiet Hiring Freeze' is a Leading Indicator of AI Job Impact

Companies are preemptively slowing hiring for roles they anticipate AI will automate within two years. This "quiet hiring freeze" avoids the cost of hiring, training, and then laying off staff. It is a subtle but powerful leading indicator of labor market disruption, happening long before official unemployment figures reflect the shift.

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210 thumbnail

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210

This Week in Startups·3 months ago

Public's Muted Reaction to AV Accident Signals Growing Acceptance

The lack of widespread outrage after a Waymo vehicle killed a beloved cat in tech-skeptical San Francisco is a telling sign. It suggests society is crossing an acceptance threshold for autonomous technology, implicitly acknowledging that while imperfect, the path to fewer accidents overall involves tolerating isolated, non-human incidents.

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210 thumbnail

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210

This Week in Startups·3 months ago

AI's Hyper-Growth Creates a New Investor Caste System

A market bifurcation is underway where investors prioritize AI startups with extreme growth rates over traditional SaaS companies. This creates a "changing of the guard," forcing established SaaS players to adopt AI aggressively or risk being devalued as legacy assets, while AI-native firms command premium valuations.

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210 thumbnail

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210

This Week in Startups·3 months ago

Startups Have a 5-10 Year Window Before Big Tech Copies Them

There appears to be a predictable 5-10 year lag between a startup's innovation gaining traction (e.g., Calendly) and a tech giant commoditizing it as a feature (e.g., Google Calendar's scheduling). This "commoditization window" is the crucial timeframe for a startup to build a brand, network effects, and a durable moat.

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210 thumbnail

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210

This Week in Startups·3 months ago

Dropbox's Decline Shows the Danger of Being a Feature, Not a Platform

Dropbox's shrinking revenue illustrates a key strategic risk. Despite being an iconic product, it became a feature within larger ecosystems like Google Workspace and Microsoft Office. Its failure to expand into a defensible, multi-product platform (e.g., failed Mailbox and Carousel acquisitions) led to its current stagnation.

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210 thumbnail

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210

This Week in Startups·3 months ago