Dane was the CEO of Squarespace from 2007 to 2011. He grew the company from ~$2M in revenue to ~$15M. He's a multi-time founder with multiple exits. His current startup, Odeko,  raised $227M.He takes us through his long journey as a founder of multiple companies and shares the key startup lessons he's learned.Why you should listen:- Why 7-day trials led to higher conversion than 30-day trials at Squarespace- Why you should talk to customers every single day.- Why SMB usage doesn't always translate into revenue.- Why you need to follow customer problems over business models and TAM.Timestamps:(00:00:00) Intro(0:00:0:37) Before Odeko(00:06:54) Leaving Squarespace(00:07:31) SumAll(00:13:01) Conversion Rates with Free Trials(00:16:10) The Start of Odeko(00:20:05) Staying Close to Clients(00:26:36) Realizing the New Model was Working(00:31:47) Landing the First Few Customers(00:37:00) Overhiring(00:39:17) Finding Product Market Fit(00:41:32) One Piece of Advice