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Episode 237:

Startups, Sales, and Spreadsheets: How a Real Estate Developer Built an AI Company

April 16, 2025

This week on The Data Stack Show, Eric and John welcome Willz Tolbert, Co-Founder & COO at Readyy. Willz shares his entrepreneurial journey from real estate brokerage to tech innovation, discussing his experiences building MapSheet and his current AI-powered startup, Readyy.ai. Listeners will learn how AI is transforming sales research, providing insights into more efficient account preparation, and bridging the gap between technological automation and human expertise in the sales process. The conversation emphasizes creating centralized data repositories for better customer engagement and highlights the need for innovative solutions to streamline data management. The group also provides valuable insights into the intersection of real estate and technology, showcasing the potential for transformative industry practices and so much more.

Notes:

Highlights from this week’s conversation include:

  • Willz’s Background and Journey (1:25)
  • Discussing Real Estate Data Challenges (2:58)
  • Inspiration for Software Creation (4:05)
  • From Spreadsheet to Software (9:04)
  • Challenges in Ownership Identification (12:24)
  • Company Acquisition (16:00)
  • Pitching Investors with Data Tools (18:46)
  • Lessons Learned from Selling the Company (21:45)
  • The Journey to Ready (26:55)
  • Sales Development Representatives Explained (29:22)
  • Role of Data in Sales (33:30)
  • Real-Time Dashboards (36:54)
  • Human-AI Collaboration (39:53)
  • Human Touch in Data Compilation (44:02)
  • Paradigm Shift in Data Access (46:19)
  • Frustrations with Sales Cycles (48:22)
  • Value of Genuine Conversations (55:23)
  • Optimizing Internal Tools (56:23)
  • Future of Data Interfaces and Parting Thoughts (57:21)

 

The Data Stack Show is a weekly podcast powered by RudderStack, the CDP for developers. Each week we’ll talk to data engineers, analysts, and data scientists about their experience around building and maintaining data infrastructure, delivering data and data products, and driving better outcomes across their businesses with data.

RudderStack helps businesses make the most out of their customer data while ensuring data privacy and security. To learn more about RudderStack visit rudderstack.com.

About the Podcast

Each week we’ll talk to data engineers, analysts, and data scientists about their experience around building and maintaining data infrastructure, delivering data and data products, and driving better outcomes across their businesses with data.

To keep up to date with our future episodes, subscribe to our podcast on Apple, Spotify, Google, or the player of your choice.

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