Uploaded October 2025 | Updated September 2026, 2 weeks ago

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Ryan Pineda faces off against elite tax strategist Karlton Dennis in a 1v1 at Paiute’s Snow Mountain, mixing competition, locker-room laughs, and real talk on building wealth. As the match swings from eagles to doubles and a back-nine scramble, Ryan and Carlton break down practical tactics: entity structure (why many owners should consider S-Corps), smart write-offs, the Augusta Rule, depreciation on rentals, and how business discipline translates to better golf (and vice versa).
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CHAPTERS:
00:00 - Intro
01:15 - Hole 1
06:27 - Hole 2
11:41 - Hole 3
23:44 - Bonus Depreciation Strategies
24:21 - Understanding Tip Taxation
27:55 - Hole 16
35:10 - Ryan's Carpool Karaoke Segment
46:14 - New Game for the Back 9
46:50 - Breaking 30 in Golf
51:29 - What I Love About This Channel
58:00 - Selling Your Business: What to Consider
01:01:20 - Why Tax Experts Recommend Real Estate
01:06:00 - Challenges of Breaking 30 in Golf
01:08:16 - Day in the Life of a CEO
01:11:19 - Tax Savings for Self-Employed Entrepreneurs
01:15:25 - Fair Score for a 2-Man Scramble
01:19:30 - Benefits of Joining a Mastermind Group
01:21:59 - Getting Back on Track for 3 Under
01:22:58 - Final Hole
01:23:57 - Outro