Last week, I met with an entrepreneur to hear his pitch for the first time. This wasn’t a fundraising pitch. Rather, it was a casual catch-up to share what he’s working on and how he’s thinking about it.

After diving into the idea and the market, I went through my five favorite questions to ask an entrepreneur.

Question #1: Why now?

Last week, I spoke with two different second-round entrepreneurs. Second-round entrepreneurs are founders who built a business in a given space, made meaningful progress, and either raised capital or sold the company to an acquirer. After their earn-out or noncompete period ends, they still feel compelled to start a new company in the same market and address unfinished busine...

With all the continued talk about the SaaS apocalypse and the challenges facing software in the age of AI and “vibe coding,” last week on the podcast 20VC, startup investor Gokul Rajaram shared his eight moats for sustainable software companies. Similar to other frameworks around what makes a business durable, these are presented in the context of software and cloud....

Last week I was talking to an entrepreneur who is going all in on a new idea. Halfway through the conversation, he asked whether he should optimize for signing new customers as quickly as possible or focus first on deepening the product and technology before pushing harder on distribution.

Right now they have a small number of beta customers providing feedback while...