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Ben Black bluntly advises against entering venture capital without deep, hands-on experience building companies. He views his own early entry into VC as a mistake, arguing that at least ten years as an operator is necessary to develop the credibility and insight required to effectively guide early-stage founders.

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In a tough funding environment, John Maraganore cautions against rushing into founding a company. He recommends that aspiring entrepreneurs first spend 5-10 years at a successful biotech. He argues that when capital is scarce, investors prioritize experienced operators, making deep industry experience a critical prerequisite for getting funded.

Starting companies as an investor is an 'insane act' that should only be undertaken by those who have previously endured the multi-year pain of being a founder. Without that firsthand experience of sacrifice and hardship, an investor lacks the necessary understanding to successfully build from scratch.

Mamoon Hamid advises against a direct path into venture capital. He argues the best training is working at a fast-growing startup to gain firsthand experience in building, shipping, and selling a product. This operational background develops the necessary empathy for founders, which is crucial for a successful VC career.

A VC's time spent in industry operating roles is invaluable. It fosters empathy for the day-to-day challenges CEOs face, enabling the investor to be a more practical and effective partner, not just a source of capital or high-level advice.

A direct path to venture capital in biotech is less effective than one that includes deep operational experience. Gaining experience in research, business development, commercial, and startup C-suite roles provides the credibility and understanding to "speak eye to eye" with portfolio companies and become a much better investor.

The expectation for venture capitalists has shifted. Founders no longer just want finance professionals; they demand investors who have direct operational experience and have been "in the trenches" of building a company. This change reflects a move towards more hands-on, value-add investing.

Initially, a16z believed only former founder-CEOs could properly advise entrepreneurs. They later realized this was flawed. Many successful founders can't articulate how they succeeded and may not be interested in the investing skillset. The firm adjusted, realizing it's better to centralize operational advice (e.g., in books and specialist partners) rather than requiring it from every GP.

For former operators who become VCs, the biggest challenge is to stop acting like an operator. The 'Hippocratic Oath of Venture' is to 'do no harm.' This means staying out of the way when a company is executing well and providing resources rather than unsolicited operational input.

Many VC firms hire former operators for their expertise, but success isn't guaranteed. The best operator-VCs avoid the urge to "backseat drive" the companies they fund. Instead, they leverage their experience with extraordinary humility, acting as a supportive advisor rather than a replacement CEO.

The transition from a C-suite operator managing thousands to an investor is jarring. New VCs must adapt from leading large teams to being individual contributors who write their own memos and do their own sourcing. This "scaling down" ability, not just prior success, predicts their success as an investor.