Wardah was a PhD graduate working at a biomedical imaging startup. But all it took was two different dentists giving her two totally different diagnoses for her to quit her full-time job.

She was unemployed with no idea what to build.

All she knew was that something was broken—and she had to fix it. Her startup Overjet is now the #1 dental AI platform, valued at $550M.

Why you should listen:
- Why founder obsession is a key trait
- Why learning speed is the main KPI early on
- Why staying close to customers is how you build the right product.
- How to get customers to share data with you and let you spend time in their office, watching how they work.

Keywords
dental AI, startup journey, funding challenges, product-market fit, impact on dental industry, speed in startups, biases in fundraising


Timestamps:
(00:00:00) Intro
(00:00:52) The Start of Overjet
(00:05:05) Obsession Increases your Chances
(00:08:15)A Bad Dentist Appointment
(00:11:35) Surpassing Dentist's Analysis Using AI
(00:15:52) Finding a Co-Founder and Fundraising
(00:24:22)Finding True Product Market Fit
(00:27:33) One Piece of Advice

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

His first startup was a cool idea: Uber for Valet Parking. Investors loved it. But the unit economics didn't work out. So he had to pivot. He ended up selling it, but decided to do things differently the second time around.

“It’s the boring stuff that makes money. Sometimes the sexy, interesting things are really great ideas, fun to use, but aren’t money makers. They aren’t durable businesses.”

With Argyle, he didn't start with a cool idea. He replaced a product customers already paid for. His pitch went from "Wouldn't it be cool if?" to "I'll do what they do but twice as well and for half the cost".

"Find a better mouse trap. Build a product that's just a better version of a product that already exists. It's a lot easier to sell."

Why you should listen:
- How to work with design partners to build the first version of your product
- How to use those partners to get credibility and make your first enterprise sale
- Keeping your sales teams small and staying close to the customer for as long as possible

Timestamps:
(00:00:00) Intro
(00:01:04) The Origins of Argyle
(00:04:03) The Aha Moment
(00:15:06) When to Charge for the Product
(00:19:31)Landing the First Customer
(00:21:38) Staying Close to Customers
(00:25:16) From Seed to Series A
(00:32:06) Delivering clear ROI
(00:35:58) Finding Product Market Fit
(00:36:38) One Piece of Advice