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:
- Rewind’s journey to Product Market Fit
- Lessons from Optimizely and being a second time founder
- Dan’s one-of-a-kind Twitter fundraising strategy
- Dan’s hot takes on the future of AI
- Where to build in AI, and what makes a “wrapper” thin versus thick
Referenced:
- Apple’s Silicon: https://www.macrumors.com/guide/apple-silicon/
- ChatGPT: https://chat.openai.com/
- Dan publicly sharing his own 360 performance reviews: https://twitter.com/dsiroker/status/1689763756459675650
- Dan’s public Twitter fundraise: https://twitter.com/dsiroker/status/1646895452317700097
- Dan’s Rewind demo tweet: https://twitter.com/dsiroker/status/1638799931891920897
- Google Glass: https://en.wikipedia.org/wiki/Google_Glass
- Google Wave: https://en.wikipedia.org/wiki/Google_Wave
- Maslow's Hierarchy of Needs: https://www.simplypsychology.org/maslow.html
- Optimizely: https://www.optimizely.com/
- Paul Graham: https://twitter.com/paulg
- Rahul Vohra’s framework for measuring and optimizing Product Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit
- Rewind AI: https://www.rewind.ai/
- Scribe (which morphed into Rewind): https://www.scribe.ai/about
- The Mom Test book: https://www.momtestbook.com/
Where to find Dan Siroker:
- Twitter: https://twitter.com/dsiroker
- LinkedIn: https://www.linkedin.com/in/dsiroker
- Personal website: https://siroker.com/
- Blog: https://medium.com/@dsiroker
Where to find Todd Jackson:
- Twitter: https://twitter.com/tjack
- LinkedIn: https://www.linkedin.com/in/toddj0
Where to find First Round Capital:
- Website: https://firstround.com/
- First Round Review: https://review.firstround.com/
- Twitter: https://twitter.com/firstround
- Youtube: https://www.youtube.com/@FirstRoundCapital
- This podcast on all platforms: https://review.firstround.com/podcast
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
In Depth