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.

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Echoing the Hippocratic Oath, a venture investor's primary job with a high-performing company is to stay out of the way and not disrupt its momentum. While providing resources for talent, capital, and strategy is valuable, it's secondary to the core principle of not interfering with a team that is already executing successfully.

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.

VCs with operational backgrounds value execution over credentials. They screen for founders who show an instinct to act and build immediately, such as launching a splash page to test demand, before raising capital. This "dirt under the fingernails" is a stronger signal than pedigree.

The most fulfilling and effective angel investments involve more than capital. Founders benefit most from investors who act as operators, offering hands-on help and staying involved in the business. This approach is more rewarding and can lead to better outcomes than passive check-writing.

VCs with operator backgrounds can provide a unique type of support, acting as a "favorite uncle." They are a safe sounding board for sensitive, human-centric challenges like layoffs, where founders may hesitate to speak with board members who are solely focused on growth metrics.

The hardest transition from entrepreneur to investor is curbing the instinct to solve problems and imagine "what could be." The best venture deals aren't about fixing a company but finding teams already on a trajectory to succeed, then helping change the slope of that success line on the margin.

Unlike operating companies that seek consistency, VC firms hunt for outliers. This requires a 'stewardship' model that empowers outlier talent with autonomy. A traditional, top-down CEO model that enforces uniformity would stifle the very contrarian thinking necessary for venture success. The job is to enable, not manage.

Lior Susan highlights the biggest mental hurdle for former operators becoming VCs: internalizing the power law. Operators are builders wired to fix problems and believe they can turn any situation around. In VC, success is driven by a few massive outliers, requiring focus on winners, not on fixing every company.

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.

To become a truly great investor, you must first experience the chaos of being a business operator. Running different types of companies, including failures, builds the firsthand knowledge and intuition needed to accurately assess the quality and risks of a potential investment.