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October 27, 2025 20 mins

In this episode of the AI Chronicles podcast, host Kyle James interviews William Hollis, founder and CEO of Raise AI, a company that leverages AI to streamline capital raising in real estate. Hollis shares his journey from a self-taught software engineer to a successful entrepreneur, emphasizing the importance of coaching and collaboration in achieving business success. The conversation delves into how Raise AI utilizes AI tools to enhance investor communication, automate processes, and improve overall efficiency in capital raising. Hollis also discusses future initiatives for the company, including an AI-driven investor relations tool that aims to connect investors with opportunities more effectively.

 

Links:

 

Raise AI: theraiseai.com

 

GPT Trainer: Automate anything with AI -> gpt-trainer.com

 

Key Moments:

  • Raise AI uses AI to streamline investor communication.
  • William Hollis's journey began with a fascination for technology and real estate.
  • Joining a mastermind helped Hollis learn effective capital raising strategies.
  • Coaching can significantly enhance personal and professional results.
  • AI tools can increase the number of investor calls booked by 30-50%.
  • Hollis transitioned from offering free services to charging clients for his expertise.
  • AI is used at every step of the capital raising process at Raise AI.
  • The importance of accountability in mastermind groups is crucial for success.
  • Future AI initiatives include an investor relations tool connected to multiple opportunities.
  • The rising tide of AI will benefit all clients of Raise AI.

Chapters

  • (00:00:00) - Introduction to AI in Real Estate Capital Raising
  • (00:02:10) - William Hollis: Journey to Founding Raise AI
  • (00:05:53) - The Importance of Masterminds and Coaching
  • (00:09:28) - Transitioning from Free Work to Paid Services
  • (00:11:01) - Leveraging AI in Capital Raising
  • (00:14:48) - Results and Impact of AI Tools
  • (00:16:38) - Future AI Initiatives at Raise AI
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