Meaning: The quote "We like to be the largest outside investor, and the first outside investor" by John Simon can be interpreted in the context of investment strategies and the approach of a potential investor. This quote reflects the preference of a potential investor to take a significant stake in a company or project and to be the first external party to provide financial support. Such an approach can have implications for the level of influence and control the investor seeks to exert, as well as the potential risks and rewards associated with being an early supporter of a venture.

The preference to be the largest outside investor suggests a desire to have a substantial stake in the ownership of a company or project. This can be indicative of a strategic approach to investment, where the investor seeks to have a significant influence on the direction and decision-making of the entity in which they are investing. By holding a large stake, the investor may aim to have a say in key strategic decisions, such as corporate governance, management appointments, and business expansion plans.

Furthermore, the desire to be the first outside investor signifies a willingness to take on early-stage investment risk. Being the first external party to invest in a venture can carry significant uncertainties and potential pitfalls, as the business model, market viability, and operational capabilities of the company may not yet be fully proven. However, being the first investor also presents the opportunity to secure favorable terms and valuations, as well as to have a pivotal role in shaping the growth trajectory of the enterprise.

This approach may be particularly appealing to venture capitalists, angel investors, or private equity firms that specialize in early-stage and growth-stage investments. By being the largest outside investor and the first to provide external funding, these types of investors can position themselves as key stakeholders and partners in the success of the venture. This can align with their objectives of seeking high-growth opportunities and actively contributing to the development and scaling of innovative businesses.

In addition, the quote can also be viewed in the context of the broader investment landscape, where the prominence of certain investors as the largest and first outside investors can signal confidence in the potential of a company or project. Such a vote of confidence from a well-regarded investor can enhance the credibility and attractiveness of the venture to other potential investors, thus facilitating subsequent rounds of funding and strategic partnerships.

Overall, John Simon's quote encapsulates a proactive and assertive approach to investment, where the investor seeks to play a leading role in shaping the future of the entities in which they invest. The emphasis on being the largest outside investor and the first outside investor reflects a deliberate strategy to wield influence and to capitalize on early-stage opportunities, while also signaling confidence in the potential of the ventures being considered.