The reference calls you make before signing a term sheet matter more than the ones during diligence. Here's who to call and what to ask.
You will spend the next 5-10 years with your lead investor. The reference calls before signing are your last chance to learn what they're actually like — not their pitch, but their behavior when things get hard. Most founders skip this step. Don't.
3-5 founders from the investor's portfolio: mix of successful outcomes, struggling companies, and companies that failed or pivoted. The struggling and failed ones tell you more than the winners — anyone can be a great investor when things are working.
"How did they behave in your hardest month?" "When you disagreed with them, what happened?" "Did they follow through on the things they promised in the pitch?" "Would you take their money again if you were starting today?" The last question is a compressed version of everything else.
"They were great in the pitch, then disappeared." "They pushed us to sell earlier than we wanted." "They changed their tune when the market turned." "They took credit publicly for wins that weren't theirs." Any of these from multiple founders is disqualifying.
Warm intros: ask a mutual connection to introduce you. Cold outreach works if you're clearly a fellow founder in diligence. State up front: "I'm considering taking their money — I need the unvarnished version." Offer confidentiality. The 15-minute calls that seem casual are the ones that give you the real story.
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