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.
Before acquiring a company, the most valuable preparation is to work as a "right-hand person" to an existing small business owner. This apprenticeship provides crucial, ground-floor experience with the operational realities that financial models and spreadsheets completely miss.
The essence of the entrepreneurial journey is the ability to tolerate immense uncertainty and fear over long periods. It involves working for months or years with little visible progress, making high-stakes decisions with limited information, and shouldering the responsibility for others' livelihoods. This psychological endurance is the ultimate differentiator.
True understanding of a business often comes only after owning it. Taking a small (e.g., 1%) starter position can initiate the research process and shift your perspective from a casual observer to a critical owner, revealing nuances and risks not apparent from the outside.
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.
Seemingly costly failures provide the unique stories, data, and scars necessary to teach from experience. This authentic foundation is what allows an audience to trust your guidance, turning past losses into future credibility.
Entrepreneurs often view early mistakes as regrettable detours to be avoided. The proper framing is to see them as necessary, unskippable steps in development. Every fumble, pivot, and moment of uncertainty is essential preparation for what's next, transforming regret into an appreciation for the journey itself.
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.
To truly learn about markets or entrepreneurship, you must participate directly, even on a small scale. This visceral experience of investing $50 or starting a micro-business provides far deeper insights than purely theoretical or cerebral learning. Combine this hands-on experience with mentorship from pros.
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.
Finding entrepreneurial success often requires a decade-long period of trial and error. This phase of launching seemingly "dumb" or failed projects is not a sign of incompetence but a necessary learning curve to develop skills, judgment, and self-awareness. The key is to keep learning and taking shots.