Brent and Tony sit down with tax pro and IRS whisperer Ruben D. Valdes to talk real consequences, IRS traps, and how to avoid screwing yourself when money starts coming in.
Ruben specializes in defending people before the IRS and the U.S. Tax Court, and he breaks down everything from audits and levies to influencer tax write-offs, shady deductions, and how to survive an IRS horror story.
This episode is packed with blunt, real-world advice for business owners, creators, and anyone who doesn’t want to end up with their accounts frozen, their assets seized, or their name in a Department of Justice press release. If you think TurboTax is enough, think again.
Chapters:
00:00 Welcome Ruben D. Valdes
00:42 What the IRS looks for in an audit
02:01 When the IRS skips legal steps and freezes your accounts
03:56 How not filing taxes becomes a criminal problem
05:30 Why offering a dollar to settle a $10M IRS debt can work
06:56 The risk of lying on your tax return
07:29 Are tax loopholes fair game?
08:45 Most of the IRS’s money comes from employment tax
09:51 Why bad bookkeeping ruins tax planning
12:46 How Amazon and big corps minimize taxes legally
14:24 Cost segregation and tax code strategies
15:26 OnlyFans, influencers, and cosmetic surgery write-offs
17:48 Chesty Love and bizarre tax court wins
19:41 S Corp advantages for creators and freelancers
21:09 The IRS wants your Instagram freebies taxed
24:49 IRS rules around travel, meals, and hotel stays
28:52 Lingerie, Victoria’s Secret, and business accounts
32:21 Cannabis business and all-cash messes
35:59 Instagram myths about tax write-offs
41:14 What real business deductions look like
43:47 When revenue levels trigger more IRS scrutiny
47:24 Why education matters more than just hiring a CPA
53:04 IRS’s Internal Revenue Manual and how it trains agents
56:55 When an audit reveals more problems than you realized
58:42 Who should hire Ruben and when
01:00:52 Protecting yourself from IRS agents and criminal referrals
01:01:24 Bare minimum tax tips for beginners
01:02:19 Ruben’s Latin Tax Academy and helping Latino entrepreneurs
Follow Ruben:
Instagram: https://www.instagram.com/taxproruben
Facebook: https://facebook.com/taxproruben
Latin Tax Academy: https://latintaxacademy.com/
Follow the podcast:
Spotify: https://podcasters.spotify.com/pod/show/twofunguyspodcast
Instagram: https://www.instagram.com/twofunguyspodcast
TikTok: https://www.tiktok.com/@twofunguyspodcast
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