This article fundamentally re-examines the relationship between venture capitalists (VCs) and founders, and the value of experience and advice. It vividly illustrates how expertise can rapidly become obsolete over time, and how VC authority is truly built and proven. The author draws on specific personal experiences and real conversations to honestly discuss what it really means to "earn the right."

1. Same Problem, Different Solutions

The author meets a founder experiencing the exact same pain they dealt with during their Opendoor days. Expecting to offer some help given the familiar situation, the author discovers that the founder's solution was completely different -- AI-powered operations, instant results, and unfamiliar unit economics.

"I had two choices. One was to trot out my stale playbook and pretend to be an expert. The other was to admit that my expertise from four years ago had already become useless."

Here, the author realizes that their past experience has already fallen behind the times.

2. The Trap of Authority and the True Meaning of 'Qualification'

Most VCs still lean on the authority of "I'm the expert," but legendary Silicon Valley investor Vinod Khosla draws a sharp line:

"You haven't earned the right to advise founders. Have you personally experienced how hard, uncertain, and traumatic it is?"

Khosla goes further, asserting that 70% of VCs don't just add zero value to founders -- they add negative value.

"70% of investors add minus value. Not zero. Minus."

VCs reading this might think "I'm fine," but the author confesses they once thought the same. Even with four startups and hands-on P&L responsibility under their belt, facing today's founders made their past expertise feel utterly meaningless.

"In front of a founder starting a business in 2025, my 2020 playbook was practically indistinguishable from one from 1990."

3. The Bitter Reality of Not Having Earned the Right

Recently in New York, the author shares an anecdote about being turned down when trying to get an introduction to a founder.

"Too busy -- maybe later."

The person who made the introduction felt bad, but the author took it in stride: "I just haven't earned the right to that meeting yet, and that's okay." It stung, but the fact that the same founder met with three other VCs that day forced a reckoning with reality.

Most VCs in this situation might bristle -- "With our fund name, they should take the meeting" -- but truly earning the right means being able to provide concrete, experience-based help.

"A founder who saved six months -- her advisor had lost the exact same enterprise customer for the exact same reason."

In other words, not "I've done sales" but:

"I lost Walmart because we couldn't guarantee 99.99% uptime on Black Friday."

Not "I understand marketplaces" but:

"I burned $2 million in Denver and only later realized the problem wasn't liquidity but supply quality."

4. Expertise Has a Shorter Shelf Life Than You Think

The author delivers a sharp reminder: the half-life of expertise is far shorter than people assume.

• Founded a company 10 years ago? That experience is useless now.
• Ran product at a public company? You only experienced 2% annual change.
• Even current operators know their own company's business but can't possibly understand the problems happening simultaneously across multiple companies.

The author believes they still have the right to help with "finding product-market fit and org building," but admits that for anything else, honesty is required.

"The three words most VCs can't say: 'I don't know.'"

What founders want isn't "someone who vaguely claims to understand" but someone who has experienced the exact same pain they're going through right now.

5. True Qualification Must Be Earned Again and Again

The core insight: true qualification isn't permanent once earned. It must be proven every time, and it can be lost the moment a founder stops responding.

"The right to advise isn't granted all at once. It's earned meeting by meeting, decision by decision, and it can be revoked by a single ignored email."

When a founder stops responding, "it's not because they're busy -- it's because you're not worth that much to them." The author urges a cold, honest self-assessment.

Conclusion

This article emphasizes that the willingness to prove your right and the courage to honestly admit when you lack the qualification to advise remain the most important qualities for an investor, even in 2025. It's not "because I'm the expert" -- only someone who has experienced the same pain the founder is going through has the true right to advise. The pace of change is only accelerating, so rather than leaning on past experience, we must rebuild our "right" ourselves, starting today, right now.