When choosing an investor, consider the value they bring beyond capital. If they buy x% of your stock, will their involvement increase the value of your remaining y%? The right investor should contribute to growing your company’s value over time, ultimately making your ownership stake worth more.

There are 2 simple ways of raising capital: Equity or Debt. Well 3, if you can pull off a Zoho and be profitable right from bootstrapped capital. So, between equity and debt, if one is a position to choose (and Debt, even in todays era, is not easily obtainable for a startup) I always counsel equity first, and some debt later if the dilution is becoming unsustainable. Simply because, excessive debt results in fixed expenses on variable revenue, and make a startup inherently unstable. So, if it has to be equity, then dilution is a law of nature. At most if there is a large disagreement on the quantum of dilution, one can consummate through Safe notes, thereby reducing this wariness (at least for a while)

You can think about losing ownership, or you can think about gaining a partner. You can think about losing a board seat, or you can think about investing in a board member. Dilution of course needs to be managed, but the attitude of "getting the most for the least" either from the investor side or the entrepreneur side is short sided.

To convince a founder who is concerned about ownership dilution, I would emphasize the strategic value our investment brings beyond capital and demonstrate how our partnership can ultimately strengthen their control and vision over the long term. Explain how our support goes beyond just funding. This includes mentorship, access to our network, operational expertise, and other resources that can accelerate growth, reduce risks, and make their vision achievable faster.

This question is poorly worded, but those are the perils of an AI world... Let's assume we're talking about VCs interested in funding a startup. In the ideal world, we're going to bring more value to the startup than just funding--so much of this is about additionality. Does the VC team understand the key risks ahead--and can they help the startup navigate them? Or is their knowledge superficial? Some relationships are transactional--and that's okay. The VC enters the cap table and doesn't have a significant role impacting decision-making. And some relationships offer softer benefits that directly impact ownership. Those should become partners, trusted colleague who have a vested (pun intended) interest in the startup's success.