How We Created a $28 Million Flywheel Using Craigslist

We couldn't figure out how to get a customer to save our life.

Our company simplified buying health insurance - a topic that consumers hated. We knew no one liked buying health insurance. We didn't know what made people actually click the buy button.

Needing answers fast, I put together a paid research study on Craigslist to find out why customers bought insurance.

I created a questionnaire using Typeform. We were paying to take the study, so could afford to be lengthy with the questions. We decided on 15 minutes of questions to answer. Once questions were completed, Calendly booked a 10 min meeting with me. After the meeting we sent them $25.

Within an hour roughly 100 people had filled out the questionnaire. Most did not meet our requirements - so we added in a step to verify they qualified for the research study. Having already talked with 100 people, we cut out the meeting.

All of our initial questions were answered within that first hour. This gave us the advantage of changing questions for the next batch of people to dig in deeper. After the consumer was paid for the study, a landing page asked if they were interested in our concierge services. Over 90% said yes, signing up immediately.

By the 3rd day we had enough data on messaging and consumer behavior to run with. We automated the entire process using Zapier. Within 4 months we hit $1M in revenue. After 2 years we hit $28M.

Thanks to an obsession with the customer, and using good old Craigslist, this became our growth flywheel.