Jayda Cheaves on $50K Real Estate Loss, Building a 7-Figure Brand, Motherhood & Cutting Her Circle

Jayda Cheaves on $50K Real Estate Loss, Building a 7-Figure Brand, Motherhood & Cutting Her Circle

Author: iHeartPodcasts April 23, 2026 Duration: 1:02:22
Earn Your Leisure
BusinessEducationNews

00:00 No Blueprint Needed
01:10 Reunion And Catch Up
02:34 Growth And Systems
04:23 Real Estate Hard Lessons
07:36 Renovation Wins And Costs
15:55 Scaling With 3PL
19:20 AI For Data Decisions
27:28 Shopify Pro And Support
28:14 Team Changes And Loyalty
29:23 Clipping Your Circle
31:15 Leveling Up Credibility
32:07 Persona Versus Boardroom
34:11 Selling Your Company
35:24 Monetizing Without Ads
38:25 Documenting Growth On YouTube
40:11 CEO Lessons Ignore Noise
42:02 Pop Ups And Retail Plans
44:22 New Ventures Feminine Care
45:56 Podcast Reality Check
47:37 Investing And Money Habits
50:06 Atlanta Origin Story
52:20 Raising Kids With Wealth
01:01:50 Wrap Up And Where To Follow

In this episode, Jayda Cheaves joins Earn Your Leisure to break down the real journey behind building the Waydamin brand—from costly mistakes to major wins. She shares how losing over $50,000 in earnest money became a hard real estate lesson, while Rashad opens up about his own $400K loss. The conversation highlights the hidden costs of homeownership and why it’s still worth it despite the setbacks.

 

They also dive into business, branding, and AI. Jayda explains how she saved over six figures using AI, why her perspective on it changed, and how tools like Shopify have helped her scale. From staying authentic to building a respected personal brand, she gives real insight into what it takes to grow and sustain a successful business.

 

The episode wraps with gems on mindset, environment, and legacy—covering everything from the impact of your circle to teaching entrepreneurship early and creating multiple streams of income. This is a must-watch for anyone serious about leveling up.

 

#JaydaCheaves #EarnYourLeisure #Entrepreneurship #RealEstate #AI #BusinessTips #WealthBuilding #FinancialLiteracy #Investing #PersonalFinance #BrandBuilding

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Hosted by Rashad Bilal and Troy Millings, Earn Your Leisure pulls back the curtain on the financial mechanics that power the worlds of sports and entertainment. This isn't just about headlines; it's a deep dive into the real stories of how money moves and how deals are made. You'll hear candid conversations that dissect business models and unpack the journeys of entrepreneurs, providing a street-smart education you won't find in a standard textbook. Each episode feels like a vital seminar, blending sharp analysis of current financial trends with the relatable context of pop culture. The Earn Your Leisure podcast, from iHeartPodcasts, operates on a simple premise: true financial freedom comes from understanding the game behind the game. It’s for anyone ready to look past the glamour and learn the practical strategies that build lasting wealth. Tune in for straightforward talk that makes complex business concepts accessible, always grounded in real-world examples from the industries that shape our culture.
Author: Language: en-us Episodes: 100

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