Patterns
Four.
That’s how many emails he’d drafted and deleted to his Partner who’d just closed a deal.
Same fund. Same title. Same carry. Never contacted the owner.
What kept him up that night?
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Before jumping on a call, a founder quickly checked LinkedIn to see the last time his investor had checked his profile.
“How can I be helpful to you?” the investor asked.
“I feel like things are finally working,” the founder replied.
He got off the call without asking for an intro to the firm’s sales specialist. Again.
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His Partner of 9 years took him for coffee. She told him he was great with one of their portfolio CFOs.
He texted his wife on the walk back. “I don't get why she wanted to do coffee.”
What if he just believed her?
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On the monthly call, the CEO said she wanted to open in a new market. She looked at him to see how he responded.
Before the next board meeting, she updated her budget. She walked in with a different number.
When she drafted a message to him after the meeting, she wrote to ask for his feedback on how it went. Then she deleted the ask. Three times.
What did he think?
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“The check is too small,” she said in IC. He nodded.
A month later, she presented her deal in IC. The equity check was smaller than his.
He voted yes.
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A CEO signed a term sheet for her Series C. The funding deadline was in two weeks.
“I’m just waiting for them to pull out,” she told her mom.
Where did she learn that?
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A VC partner wakes up in the middle of the night grinding his jaw.
In the weekly partner meeting, his chest is tight.
When another dad at school asks him what firm he works at, though, he exhales.
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In July, he had feedback for his co-founder. He told his friend about it.
In November, his co-founder referred a new Head of Engineering.
In January, they had their Board meeting.
In February, he started looking for a new co-founder.
At what cost?