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  1. This Week in Startups
  2. How to Raise a Seed Round in 2026: Ask Jason | E2294
How to Raise a Seed Round in 2026: Ask Jason | E2294

How to Raise a Seed Round in 2026: Ask Jason | E2294

This Week in Startups · May 29, 2026

Jason Calacanis on raising a seed round: treat fundraising as a sales funnel, build moats against AI, and adapt to the evolving startup landscape.

Judge Investors by Their Past Investments, Not Their Polite Rejections

Investors will often be polite and say a startup is "too early." However, founders should ignore these words and instead analyze the investor's portfolio. If an investor has no history of funding pre-product companies, their feedback is irrelevant; they were never a real prospect.

How to Raise a Seed Round in 2026: Ask Jason | E2294 thumbnail

How to Raise a Seed Round in 2026: Ask Jason | E2294

This Week in Startups·2 months ago

Startups Now Reach First Revenue in Weeks, Not Years

The cost and time to build a startup have collapsed. In the dot-com era, it took $3-5M and over a year to launch. Now, with no-code tools and AI, founders can build a product and get their first customers in a matter of weeks, sometimes even before raising any capital.

How to Raise a Seed Round in 2026: Ask Jason | E2294 thumbnail

How to Raise a Seed Round in 2026: Ask Jason | E2294

This Week in Startups·2 months ago

Finding Investor Alignment is a Sales Job, Not a Matching Problem

Founders often feel fundraising is a marketplace with weak signals. The reality is that it's a sales process. The founder's job is to qualify leads by researching an investor's portfolio, check size, and investment thesis to find a genuine fit, rather than hoping for a match.

How to Raise a Seed Round in 2026: Ask Jason | E2294 thumbnail

How to Raise a Seed Round in 2026: Ask Jason | E2294

This Week in Startups·2 months ago

Create a Paid VC Training Program by Paying Apprentices First

To build a venture capital training program that rivals established ones like Kaufman Fellows, start by creating an internal apprentice program that pays participants. Refine the curriculum until it's so valuable you can charge for it, offering real-world experience that legacy programs lack.

How to Raise a Seed Round in 2026: Ask Jason | E2294 thumbnail

How to Raise a Seed Round in 2026: Ask Jason | E2294

This Week in Startups·2 months ago

VCs Now See Hardware as a Defensible Moat, Not a Liability

The venture capital perspective on hardware has completely flipped. Previously seen as a difficult and capital-intensive area to be avoided, hardware is now considered one of the few remaining defensible moats. Physical products like WHOOP and Eight Sleep create customer lock-in that software alone cannot.

How to Raise a Seed Round in 2026: Ask Jason | E2294 thumbnail

How to Raise a Seed Round in 2026: Ask Jason | E2294

This Week in Startups·2 months ago

Cutthroat Self-Interest Is a Path to Success That Damages the Tech Industry

Jason Calacanis identifies Mark Zuckerberg and Sam Altman as people he dislikes not for personal reasons, but because their self-interested decisions, while making them extraordinarily successful, have damaged the tech industry's reputation. This highlights a paradox where certain negative traits can be a shortcut to massive success.

How to Raise a Seed Round in 2026: Ask Jason | E2294 thumbnail

How to Raise a Seed Round in 2026: Ask Jason | E2294

This Week in Startups·2 months ago

Modern Seed Fundraising Requires Contacting 150 Investors for Just Two Term Sheets

Jason reveals the harsh reality of the current seed fundraising funnel. Founders need to target 150 funds to secure 50 meetings, which leads to about 20 second meetings, ultimately resulting in only two term sheets. This is the new baseline for playing the game.

How to Raise a Seed Round in 2026: Ask Jason | E2294 thumbnail

How to Raise a Seed Round in 2026: Ask Jason | E2294

This Week in Startups·2 months ago

The Real 'FU Money' Number is $10 Million, Not Billions

The true threshold for financial independence—'FU money'—is $10 million. At this level, a conservative 5% annual return generates $500k, providing complete freedom to pursue any project without financial pressure. The pursuit of billionaire status beyond this point yields diminishing returns on freedom.

How to Raise a Seed Round in 2026: Ask Jason | E2294 thumbnail

How to Raise a Seed Round in 2026: Ask Jason | E2294

This Week in Startups·2 months ago

Compete With OpenAI by Building Community and Services They Won't Touch

To build a moat against large language models like ChatGPT, focus on features they will never prioritize. Build multiplayer functionality, a strong user community, and human-in-the-loop support services around the core AI. These layers create defensibility that a generic interface cannot replicate.

How to Raise a Seed Round in 2026: Ask Jason | E2294 thumbnail

How to Raise a Seed Round in 2026: Ask Jason | E2294

This Week in Startups·2 months ago