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

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