Summary: Semil Shah and Jenna chat about his first investments at Haystack in companies like Hired and Instacart and reflect on a few big bets taken by portfolio companies like Wag and Managed by Q. We discuss the realities of being a VC such as creating space to let your mind rest so your subconscious can kick in evaluating investments, the challenge of saying ‘No’ to founders you admire, as well as developing a willingness to concentrate risk to have outsized returns. We also walk through key insights from Semil’s blog including: whether you need to be paranoid to succeed, the difference between stubbornness and resilience and how to cultivate the latter, in the moment tips to take a step back to make decisions from a place of clarity not adrenaline, and always choosing the opportunity where you can learn the most.
