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RewindAI CEO Dan Siroker: AI Wearables & Fundraising in Public

Dan Siroker
Dan Siroker
Co-Founder & CEO
February 6, 2024

Dan Siroker is the co-founder and CEO of Rewind AI. He also co-founded Optimizely, and he was the Director of Analytics at Obama’s first presidential campaign.     

On this episode of World of DaaS, Auren and Dan discuss how Rewind raised its Series A in public, and how the unconventional move benefited the company. Dan shares insights on creating a compelling pitch and the importance of practicing and honing the pitch through meetings with investors. 

Dan also discusses the challenges and opportunities in building screenless wearable devices, and what future wearables could look like. Auren and Dan explore how wearable AI tech could affect cancel culture, transparency, and surveillance. The conversation closes with Dan’s advice for parent founders and his thoughts on conventional wisdom and advice.

World of DaaS is brought to you by SafeGraph & Flex Capital. For more episodes, visit

You can find Auren Hoffman on X at @auren and Dan Siroker on X at @dsiroker

Follow World of DaaS @WorldOfDaaS 

Editing and post-production work for this episode was provided by The Podcast Consultant (

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Erik Torenberg: Optionality, AI & Elites

Erik Torenberg was the first employee at Product Hunt, and the founder and chairman of On Deck. He’s currently a partner at Village Global and the founder of Turpentine podcast network.  

Erik and Auren discuss the startup founder mindset and what it takes to be successful in tech. Erik shares the career strategies and frameworks that have allowed him to found multiple companies and a venture capital firm. 

They also discuss unconventional financial arrangements that could allow more people to found companies, like income share agreements and equity pooling. Erik also shares some of his insights on podcasting and why it’s one of the best ways to learn. 

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You can find Auren Hoffman on Twitter at @auren and Erik on Twitter at @eriktorenberg

August 1, 2023

Avlok Kohli, AngelList CEO: AI and Dual Threat CEOs

Avlok Kohli is the CEO of AngelList and the founder of FastBite and Fairy. 

Auren and Avlok discuss the underestimated impact of AI and how it could be creating a tech mega cycle. Avlok explains the importance of unique data as a moat for companies building on top of large language models, and how this technology can disrupt incumbents. 

They also discuss the rise of Dual Threat CEOs and their outsized success in early stage venture capital. Avlok makes the case for why more current operators should start funds, and explains why they’ll thrive in the changing VC landscape. 

World of DaaS is brought to you by SafeGraph & Flex Capital. For more episodes, visit

You can find Auren Hoffman on Twitter at @auren and Avlok Kohli on Twitter at @avlok.

May 2, 2023