Thread
1. I have been trying to find the best "first question" to ask a startup when I meet with them. After many iterations, I think I have it. Here it is, and here's why it works.
2. The question is "Tell me your founding story".

Here's why it's a good first question.
3. It puts the founders at ease. Instead of being quizzed upfront about market size, competition, or business model, they get to tell a story. And who doesn't like story telling? It helps ease into the conversation.
4. It gives insight into how the founders encountered the problem they are trying to solve. The more first-hand their experience with this problem, either at life or work, the better. Authenticity of founder-problem fit should lead to unique, non-obvious insights.
5. It sheds light on the depth of the founder relationship. Did they just meet up a month ago, or have they known and worked with each other for a decade? Founder breakup or general lack of alignment is a top reason behind early startup failure.
6. Ultimately, this is the analogue of "Tell me about yourself", which IMO is an excellent first question for interview candidates. A simple question that reveals a ton about the company and founders, their motivations and relationship, and sets the stage for deeper exploration.
7. Finally, it also shows how well the founders communicate. A rambling story makes me doubt that the founders can communicate and inspire employees, investors & other stakeholders. So much of a startup success is Narrative, and the founding story is the foundational narrative.
8. Startup founders: do practice telling your founding story crisply and in a way that highlights the authenticity of your mission, speaks to the depth of your founder relationship, and showcases your ability to inspire.
Mentions
See All