How should founders test whether a prospective investor's promised help is genuine before accepting their money?

Katherine Boyle · Oct 1, 2020

The timing of when an investor leans in should be founder-driven, with the investor proving themselves to the founder before the round

It's part of an auditioning process where the investor earns the right to work with the founder, and respecting the founder's process matters

Scope: company dependent; preempting is fine if you have conviction and the founder is excited about it

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Mati Staniszewski · Sep 8, 2025

The window when investors are courting you, before you accept any term sheet or money, is the best time to test whether they can actually be helpful.

That is the moment of maximum leverage — you can ask them to bring angels you want on the cap table or make introductions before you commit.

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Cem Sertoglu · Nov 20, 2024

Founders should ask seed and early-stage investors for their follow-on data, because it is a strong indicator of how much the investor actually cares

Founders are buying care from investors, and follow-on behaviour is where care shows up measurably

59:40 Ask for follow on track record data to test genuine investor care

Cristóbal Valenzuela · Aug 28, 2023

Founders should make investors pitch the company back to them to test alignment, and should walk away from misaligned investors even on great terms

An investor may understand the company from a completely different vantage point than yours, and since you'll work with them for years that misalignment won't work long term; he turned down a term sheet with a beautiful valuation after hearing an investor describe Runway in a way that didn't match what they were doing

26:56 Make investors pitch the company back to you and walk away from misalignment even at great terms

Saam Motamedi · Jul 15, 2024

Founders should ask VCs how they actually work with companies and take references on them, and far too few do so when choosing between term sheets.

The right questions are what the nature of the working relationship is and what would be different about the company without that person's involvement.

62:25 Ask how vcs work with companies and take references on them

Harry Stebbings · Sep 8, 2025

Asking an investor for concrete help is a good litmus test of whether their interest is genuine or just platitudes.

26:53 Concrete help requests are the litmus test of genuine investor interest