Navigating Challenges in the SMB World: A Founder's Journey

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.

Keywords
Squarespace, Odeko, product-market fit, PMF, blogging, freemium model, trial period, data analytics, startup,, customer relationships, business model, pivot, success factors, logistics, hiring, purpose

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

Send me a message to let me know what you think!