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

Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure

Join the EYL community for deeper training and a more detailed approach:
https://www.eyluniversity.com

Join the number one stock club in the world:
https://www.ianinvest.com

Invest Fest | August 7-9, 2026
Grab early bird tickets now: https://www.investfest.com

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&mdash;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&rsquo;s still worth it despite the setbacks.
&nbsp;
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.
&nbsp;
The episode wraps with gems on mindset, environment, and legacy&mdash;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.
&nbsp;
#JaydaCheaves #EarnYourLeisure #Entrepreneurship #RealEstate #AI #BusinessTips #WealthBuilding #FinancialLiteracy #Investing #PersonalFinance #BrandBuilding
Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure
Join the EYL community for deeper training and a more detailed approach: https://www.eyluniversity.com
Join the number one stock club in the world: https://www.ianinvest.com
Invest Fest | August 7-9, 2026 Grab early bird tickets now: https://www.investfest.com

Welcome to The Earn Your Leisure Podcast. Rashad Bilal and Troy Millings will be your host. Earn Your Leisure will be giving you behind the scenes financial views into the entertainment and sports industries as well as highlighting back stories of entrepreneurs. We will also be breaking down business models and examining the latest trends in finance. Earn Your Leisure is a college business class mixed with pop culture. We blend the two together for a unique and exciting look into the world of business. Let’s go!! #earnyourleisurepodcast

Earn Your Leisure

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

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/c7394a33-0c39-4ae3-b22a-b4340131e848/transcript