In a non-control deal, an investor cannot fire management. Therefore, the primary diligence focus must shift from the business itself to the founder's character and the potential for a strong partnership, as this relationship is the ultimate determinant of success.

To predict the future health of a partnership, intentionally have difficult conversations before any investment is made. If you can't productively disagree or discuss serious problems before you're formally linked, it's highly unlikely you'll be able to do so when the stakes are higher post-investment.

To ensure alignment, VCU provides its investment memo to a manager before committing capital. This allows the manager to correct misunderstandings and confirms a shared understanding of the strategy and KPIs, making difficult future discussions more objective and data-driven.

Oshkosh avoids demanding a Right of First Refusal, which can scare off potential acquirers. Instead, they secure information rights and board observer seats. This ensures they are notified of any acquisition talks, allowing them to enter a competitive process without limiting the startup's exit opportunities.

Instead of demanding a controlling 'Right of First Refusal' (ROFR), Snowflake's venture arm uses a softer, more founder-friendly 'Right of First Notification' (ROFN). This doesn't block other offers but ensures they get a heads-up before an exclusive deal is signed, giving them a chance to participate.

Traditional venture funds have a mandate to distribute shares post-IPO. A crossover investor can credibly promise a founder, 'I never have to sell your stock to get paid. If you execute, I can hold you forever.' This aligns the investor with the founder's long-term vision and offers stability.

Deciding whether to back a competitor is fraught with conflict. When the speaker considered investing in Stripe, a Square executive called it a conflict, but CEO Jack Dorsey approved. This shows opinions on threats vary internally, justifying multiple checks before proceeding with a potentially conflicting investment.

By Series C, founders are often saturated with guidance from early-stage, company-building VCs. A powerful pitch for a late-stage investor is to explicitly state they trust the existing board and will not offer unsolicited 'wise advice.' This positions them as a supportive, low-maintenance capital partner.

Conflicts over selling a company often hide personal or firm-level motivations. Seth Levine of Foundry Group advocates for bluntly asking about these biases—like a VC needing DPI for fundraising or a founder needing personal liquidity—because you cannot solve a problem until it is openly acknowledged.