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Invest Fest | August 7-9, 2026
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Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure
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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

The Downside of Being in The NFL

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/f65d759c-ea6b-4bcc-8e94-b46800fa2e80/transcript

Jay-Z's Warning The $6 Trillion Wealth Opportunity Most People Miss

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/90c26983-5da1-4fcb-97d2-b46f00d06197/transcript

TIMESTAMP:
00:00 IRS Wake Up Call
01:18 Meet Carlton Dennis
03:05 From Fitness To Taxes
05:40 Learning The Tax Plan
07:34 What A Tax Plan Is
09:38 Who The Tax Code Rewards
11:01 Capital Gains And Losses
13:12 LLC To S Corp Setup
16:07 S Corp Vs C Corp
18:14 Retirement And Key Dates
21:48 Roth And Kids Payroll
23:14 HSA And Car Write Offs
25:44 Cost Seg And Short Term Rentals
29:17 Augusta Rule Explained
30:39 Audit Triggers And Omissions
31:07 Audit Red Flags
32:33 SALT Deduction Update
34:12 Child Credits and Accounts
36:58 Earners vs Owners
38:18 Entity Structure Basics
40:29 Delaware vs Wyoming
42:21 California Billionaire Exodus
44:09 LLCs for Liability
45:27 Unrealized Gains Debate
46:41 YouTube Growth Story
49:05 Top LLC Write Offs
50:21 Charity Foundation Strategy
54:16 Income Shifting with C Corps
56:49 Firm Model and Training
01:02:50 Movie Tax Write Offs
01:04:14 Timing Asset Purchases
01:04:54 Final Takeaways

In this episode of Earn Your Leisure, tax strategist Karlton Dennis breaks down the wealth-building tax strategies that business owners, investors, and high-income earners use to legally reduce their tax burden and keep more of their money.

Karlton explains everything from capital gains taxes, LLC structures, Delaware vs. Wyoming incorporations, cash balance plans, HSAs, cost segregation studies, rental property tax strategies, the Augusta Rule, vehicle write-offs, SALT deductions, child tax credits, retirement planning, and the most common mistakes that trigger IRS audits. He also reveals why understanding the tax code is one of the most important skills for building and preserving wealth.

Whether you’re an entrepreneur, investor, real estate owner, or simply looking to become more financially intelligent, this conversation is packed with actionable insights that could save you thousands—or even hundreds of thousands—of dollars. Don’t miss this masterclass with Karlton Dennis on how the wealthy use the tax code to their advantage.

#EarnYourLeisure #KarltonDennis #Taxes #TaxStrategy #WealthBuilding #BusinessOwners #Entrepreneurship #RealEstateInvesting #Investing #FinancialLiteracy #TaxPlanning #LLC #CapitalGains #IRS #PersonalFinance #WealthCreation #MoneyManagement #SmallBusiness #TaxSavings #FinancialFreedom

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

TIMESTAMP: 00:00 IRS Wake Up Call 01:18 Meet Carlton Dennis 03:05 From Fitness To Taxes 05:40 Learning The Tax Plan 07:34 What A Tax Plan Is 09:38 Who The Tax Code Rewards 11:01 Capital Gains And Losses 13:12 LLC To S Corp Setup 16:07 S Corp Vs C Corp 18:14 Retirement And Key Dates 21:48 Roth And Kids Payroll 23:14 HSA And Car Write Offs 25:44 Cost Seg And Short Term Rentals 29:17 Augusta Rule Explained 30:39 Audit Triggers And Omissions 31:07 Audit Red Flags 32:33 SALT Deduction Update 34:12 Child Credits and Accounts 36:58 Earners vs Owners 38:18 Entity Structure Basics 40:29 Delaware vs Wyoming 42:21 California Billionaire Exodus 44:09 LLCs for Liability 45:27 Unrealized Gains Debate 46:41 YouTube Growth Story 49:05 Top LLC Write Offs 50:21 Charity Foundation Strategy 54:16 Income Shifting with C Corps 56:49 Firm Model and Training 01:02:50 Movie Tax Write Offs 01:04:14 Timing Asset Purchases 01:04:54 Final Takeaways
In this episode of Earn Your Leisure, tax strategist Karlton Dennis breaks down the wealth-building tax strategies that business owners, investors, and high-income earners use to legally reduce their tax burden and keep more of their money.
Karlton explains everything from capital gains taxes, LLC structures, Delaware vs. Wyoming incorporations, cash balance plans, HSAs, cost segregation studies, rental property tax strategies, the Augusta Rule, vehicle write-offs, SALT deductions, child tax credits, retirement planning, and the most common mistakes that trigger IRS audits. He also reveals why understanding the tax code is one of the most important skills for building and preserving wealth.
Whether you&rsquo;re an entrepreneur, investor, real estate owner, or simply looking to become more financially intelligent, this conversation is packed with actionable insights that could save you thousands&mdash;or even hundreds of thousands&mdash;of dollars. Don&rsquo;t miss this masterclass with Karlton Dennis on how the wealthy use the tax code to their advantage.
#EarnYourLeisure #KarltonDennis #Taxes #TaxStrategy #WealthBuilding #BusinessOwners #Entrepreneurship #RealEstateInvesting #Investing #FinancialLiteracy #TaxPlanning #LLC #CapitalGains #IRS #PersonalFinance #WealthCreation #MoneyManagement #SmallBusiness #TaxSavings #FinancialFreedom
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

How the Rich Avoid Paying Millions in Taxes: Wealth Secrets You NEED to Know w/ Karlton Dennis

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/0e12e2e5-c1c3-4a61-9403-b46d00bfc3ba/transcript

Give Your Child a 700 Credit Score

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/7d6a53e3-228d-48ff-8db9-b46800fa2e80/transcript

The Downside of Being in The NFL

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