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

April 23, 2026 · 1h 2m

About this episode

Jayda Cheaves discusses her journey in building the Waydamin brand, sharing lessons from real estate losses and insights on business growth and AI.

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…

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