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  1. This Week in Startups
  2. Jason’s ultimate dream mega-purchase + Founder Q’s | E2228
Jason’s ultimate dream mega-purchase + Founder Q’s | E2228

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228

This Week in Startups · Dec 29, 2025

Jason Calacanis on managing VC inbound, the value of European capital, avoiding extravagant purchases, and the future of vertical AI applications.

Common 'Mosquito Bite' Problems Are More Lucrative Than Rare 'Shark Bite' Crises

Founders often chase severe, 'shark bite' problems that are rare. A more sustainable business can be built solving a common, less severe 'mosquito bite' problem, as the market size and frequency of need are far greater.

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228 thumbnail

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228

This Week in Startups·2 months ago

Turn a Niche, Invalidated Product into a Profitable Bespoke Software Engagement

If you build a product for a problem that only one customer has, don't just abandon it. Offer to turn it into a high-priced, bespoke solution for that single customer. This salvages the work and creates a profitable revenue stream, avoiding a total loss.

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228 thumbnail

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228

This Week in Startups·2 months ago

Users Prefer Giving Audio Feedback Over Text and Strongly Dislike Video

When building feedback tools, recognize that users favor audio. It's easier for multitasking, supports multiple languages, and feels less inhibited than writing. Conversely, video feedback is highly disliked and should be avoided as a primary collection method.

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228 thumbnail

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228

This Week in Startups·2 months ago

Vertical AI Apps Will Beat General LLMs by Offering Superior Refinement and Community

While large language models (LLMs) are powerful general tools, they will be outcompeted in specific verticals by specialized AI applications. These niche products, like Calm for meditation, win by providing superior design, features, and community tailored to a dedicated user base.

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228 thumbnail

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228

This Week in Startups·2 months ago

CEOs Must Systematically Bypass Middle Management to Get Unfiltered Feedback

Feedback often gets 'massaged' and politicized as it travels up the chain of command. Effective leaders must create direct, unfiltered channels to hear from customers and front-line employees, ensuring raw data isn't sanitized before it reaches them.

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228 thumbnail

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228

This Week in Startups·2 months ago

Great VCs Master Four 'D's': Deal Flow, Decisions, Doubling Down, and Distributions

A simple framework to evaluate a VC's skill is the four 'D's'. They need proprietary Deal Flow, the ability to make good Decisions (initial investment), the conviction to Double Down on winners, and the discipline to generate Distributions (returns) for LPs.

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228 thumbnail

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228

This Week in Startups·2 months ago

Founders Should 'Neg' Inbound VCs by Delaying Meetings to Increase Investor Interest

When a VC reaches out before you're fundraising, don't take the meeting. State that you're busy building and suggest a meeting in a future quarter. This scarcity tactic, or 'negging,' signals confidence and makes your startup more desirable to the investor.

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228 thumbnail

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228

This Week in Startups·2 months ago

Foreign Founders Can Gain an Edge by Targeting VCs Outside of Silicon Valley

A European founder targeting the US market shouldn't dismiss European VCs. You might be the top priority in a European firm's portfolio, receiving more attention and support than you would as a lower-priority deal for a top-tier, oversubscribed Silicon Valley firm.

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228 thumbnail

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228

This Week in Startups·2 months ago

Extravagant Purchases Create Distracting 'Cognitive Load' for Entrepreneurs

High-net-worth individuals often find that owning luxury assets like multiple homes or cars adds significant mental overhead. Every new possession becomes a responsibility, pulling focus away from core business activities, unlike investing in startups which provides joy with less cognitive load.

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228 thumbnail

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228

This Week in Startups·2 months ago