The CTO Compass

RaiseAI: Cutting the Time for a Capital Round in HALF ft. William Hollis


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Hollis discusses the intricacies of raising capital, emphasizing the importance of multiple interactions with potential investors. He highlights the average of 32 touchpoints required to secure a significant investment and explores how AI can streamline this process without compromising the quality of engagement.

Chapters

00:00 Beginnings with Technology and Career

06:20 When to use Tech and People

08:08 Implementing Tech into Real Estate (Raise AI)

12:45 Streamlining "32 Touch points" with AI

19:31 Building a Team and AI Adoption

24:06 AI Future-proofing and Relationships

28:36 Why Real Estate AI and Building Culture

33:02 The Future of Raise AI

About Hollis

William Hollis, known as “Hollis,” is the Founder & CEO of Raise AI, where he helps real estate capital raisers and fund managers use AI-powered automation to streamline investor communication, increase deal visibility, and raise capital faster. A self-taught software engineer turned real estate investor, Hollis specializes in bridging cutting-edge AI technology with the real-world challenges of capital raising.

Born and raised in Hollis, Queens, NY, he has built his career at the intersection of AI, automation, and real estate. Before founding Raise AI, Hollis developed AI solutions for global brands like Disney and Nike, then applied those same efficiencies to real estate by launching 24 Capital Group in 2022 and 24 Tech Systems in 2024. Today, through Raise AI, he empowers dealmakers with scalable, intelligent systems that replace manual follow-ups and outdated workflows—helping them move from hustling for capital to raising it effortlessly.

Where to find Hollis

• RaiseAI: https://theraiseai.com/

• Website: https://williamhollis.com/

• LinkedIn: https://www.linkedin.com/in/rei-hollis/

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The CTO CompassBy Mark Wormgoor