AI Hot Takes and Unusual Twitter Fundraising Strategies with Dan Siroker (Rewind AI)
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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