What to ask when evaluating an early-stage startup

I’ve been among the first 30 hires at two high-flying hypergrowth startups (Klaviyo & Postscript).

Recently, I have been brainstorming an idea around solicited advice… the questions people always want to know about working in tech startups as a non-founder.

The reality is most folks in startups are the crew working on the mission and don’t know what’s realistic/normal/etc. A common question I get a lot from folks:

“What questions do you ask when you're evaluating joining an early stage startup?”

I always start with the same questions. Always. And usually in rapid fire.

• What’s your ARR today? The target for the end of year?

• Walk me through the growth YoY since the inception of the business.

• What’s your burn rate?

• What’s your run rate?

• How many months of runway do you have today? How much money is in the bank?

• What’s your churn rate? ACV? CAC?

• Why do customers churn?

• What’s the biggest challenge your business is facing today?

These answers paint a quick picture of the state of a business and will tell you pretty quickly how well a founder knows (or doesn’t know) their business.