The single most important characteristic for picking your startup investors

Being there when it matters most

It's easy to be friends with someone when life is going well for them. Real friends are there for you when you’re down. They provide comfort when you are depressed, they hold you when a family member dies. They distract you when you need it most. Real friends are the people you want in your life. 

Not all principles translate well from private life into the business world. However, the principle of relying on people who are there for you in bad times does, especially when picking the best investors for your company.

Investors can bring many different things to the table when they invest in your startup. Above all others, there is one trait that many of the best investors share: the ability and willingness to help you get through a crisis. If you are a founder choosing who will invest in your startup figure out how your potential investors act when things are rough. You do not want the extra burden of difficult investors at an inopportune time. Instead, you want people who actively try to help you escape the disaster. If you want to learn where an investor stands, go ask the founders of their portfolio companies. Do not solely rely on the intros the investors provide, reach out to some founders yourself to avoid cherry-picked selections. You will get the best insights by speaking with founders who have been through tough times.

For me, sharing wins and losses with people who matter is much of what life is about. 

The proudest moments in my rather short investing career were the times I was called on for help.  I felt a sense of accomplishment when a founding team called me in as a mediator for a major founder disagreement. I felt a sense of purpose when a team sent me an emergency message that they were afraid of telling their investors that they needed to pivot. I enjoy helping them with introductions to new customers or connecting them with potential lead investors for their next round. However, the trust they have in me to be on their side in the bad phase is the most important to me. 

Much of that feeling of importance is derived from my own experience. It reminds me of who saved me when I needed help.

I am undoubtedly thankful for people who support me when things are going well. At the same time, I am even more grateful to those who believed in me when things were just starting. And I will walk through fire for the people who were there for me when things seem to be crashing down. 

This sentiment resonates with many of my founder friends. The people they remember most fondly are those who supported them early, and those who helped them to recover from disaster. 

So, if you are a founder, do your research. If you are an investor, strive to be an immovable pillar, especially in bad times. And if you are a friend, offer your full support when your friends need you. Share your wins, share your losses, and make it to wherever you are going, together.