Dan Siroker is the co-founder and CEO at Rewind AI, a personalized AI powered by everything you’ve seen, said, or heard. Dan launched Rewind to an emphatic response on Twitter, and used a public pitch video to fundraise at a $350m valuation. Prior to starting Rewind, Dan co-founded Optimizely, which reached $120m ARR before being acquired by Episerver, a content management company. Dan was also the Director of Analytics for Obama’s first presidential campaign.

In today’s episode, we discuss:

Referenced:

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Timestamps

(02:25) Rewind's origin story

(04:04) How Rewind works

(07:24) Managing scope when building Rewind

(13:47) How Dan thought about early user feedback

(17:08) Rewind's cultural mantra for shipping and validating fast

(18:35) Product positioning as a category creator

(20:39) Lessons from being a 2nd time founder

(26:11) Cultural values at Optimizely and Rewind

(28:22) How Dan defines and operationalizes Product Market Fit

(32:06) Audience segmentation

(34:32) Measuring Product Market Fit

(36:23) Dan's take on the current AI hype

(38:11) What makes a "wrapper" thin vs thick?

(39:50) Where founders should and shouldn't build within the AI ecosystem

(43:22) Trends in consumer expectations around data privacy

(46:59) What AI might look like 10 years from now

(51:09) Dan's one-of-a-kind public Twitter fundraise

(59:40) What's next for Rewind?

(61:26) The influence of Paul Graham

(62:47) Dan's #1 piece of advice

(64:23) Dan's #1 book recommendation