AI Hot Takes and Unusual Twitter Fundraising Strategies with Dan Siroker (Rewind AI)
In Depth
Fundraising Through Twitter
The chapter explores the unconventional approach of fundraising through Twitter, highlighting the reasons behind it and the strategies employed to build trust and attract potential investors.
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
The AI-powered Podcast Player
