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August 19, 2025 38 mins

Are you a startup founder looking to disrupt an industry with AI, but unsure how to secure significant funding? Do you want to understand what it takes to get noticed by top-tier VCs and build a category-defining company? 

In this episode of Funded, we speak with Aaron Cannon, Co-founder and CEO of Outset, an AI-moderated research platform, as he shares the incredible journey of closing their $17 million Series A funding. Discover how Outset leveraged AI to create a new market category, achieved rapid customer adoption with global brands, and navigated the complexities of fundraising from Y Combinator to a successful Series A.

Download the Multiplier Marketing Megapack today. Exclusive offer for all our listeners — get all our Startup Guides in one go! Over 50 pages of advanced tips and advice that dive deep into content marketing, search advertising, and marketing attribution.

Aaron is the co-founder and CEO of Outset, where he’s leading the development of the world’s first agent-led research platform powered by AI-moderated interviews. He brings over a decade of experience in product strategy and leadership from roles at Tesla, Triplebyte, and Deloitte, with a passion for building tools that bridge design, business, and user research. Aaron studied economics and entrepreneurial leadership at Tufts University and continues to mentor young innovators.

Aaron, Morgan, and Chris discuss:

  • What AI-moderated research is, how it enables companies to understand human behavior.
  • How Outset's AI presents questions via voice and text, allowing participants to respond with video, voice, or screen share.
  • Aaron's prediction that AI-moderated research will eliminate the distinction between quantitative and qualitative data.
  • The process of securing $17 million in Series A funding led by 8VC.
  • Why choosing the right individual partner is more important than the firm itself.
  • How Y Combinator provides brand cachet, a supportive community, intense focus, and a structured environment.
  • That fundraising is primarily about storytelling and the importance of continuously refining your narrative based on feedback.

Aaron Cannon's journey with Outset AI provides a masterclass in securing venture capital by building an innovative product, understanding your market deeply, and mastering the art of the fundraising narrative.

Thank you for listening! Tune in to all the episodes for practical tips on crushing your startup marketing goals. Don’t forget to follow, rate, and review the podcast, and tell us your key takeaways!


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