Mailbox Money Show

Webinar - 2026 Tax Secrets for Investors


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This webinar replay from the Mailbox Money Show features Bronson Hill moderating an expert panel on the rise of private credit as a powerful, tax-efficient cash-flow alternative to traditional banking and Wall Street investments. The discussion explores how private credit fills lending gaps left by post-2008 regulations, offers faster capital access for businesses, delivers strong risk-adjusted yields (10–34% net in various models), and provides diversification across industries like litigation finance, medical receivables, real estate bridge lending, and merchant cash advances.


Panelists:


Yonah Weiss — Business Director of Madison SPECS, specializing in cost segregation studies that accelerate depreciation and generate massive tax deductions for real estate investors (especially under current 100% bonus depreciation rules).


Kaaren Hall — Founder of UDirect IRA Services, a leading expert in self-directed IRAs and retirement accounts, author of the BiggerPockets Guide to Self-Directed IRAs, and advocate for using retirement funds to invest in alternative assets like real estate and private credit.


Courtney Moeller — Oil & gas investment specialist focused on working interest deals that deliver significant upfront tax deductions (often 80–90%+) and ongoing depletion allowances to offset active, passive, and capital gains income.


TIMESTAMPS


0:40 - Welcome!

1:36 - Event Overview

3:19 - Panelist Introductions: Yonah Weiss, Kaaren Hall, Courtney Moeller

5:02 - Audience Poll: Who You're Most Excited to See

5:41 - 2026 Tax Secrets Overview

6:05 - Yonha Weiss: Cost Segregation and Accelerated Depreciation

7:30 - Kaaren Hall: Self-Directed IRAs and Retirement Accounts

8:29 - Courtney Moeller: Oil and Gas Tax Benefits

10:51 - Real Estate Professional Status and Active Income Offset

12:20 - Holistic Tax Planning and Exit Strategies

13:08 - Self-Directed IRA Asset Classes and Prohibited Transactions

15:29 - Super Bowl Tickets in Roth IRA Example

17:42 - UBIT/UDFI in Self-Directed IRAs and Syndications

19:44 - Oil and Gas Risks and Operator Due Diligence

21:55 - Planning Mistakes and Last-Minute Tax Fixes

23:04 - Primary Residence vs Investment Property Depreciation

24:57 - Single-Family and Vacation Rental Cost Segregation

26:56 - Oil Price Impact on Returns and Break-Even Points

28:05 - Bonus Depreciation on Gas Stations and Car Washes

29:38 - Business Equipment and Section 179 Deduction

31:32 - Roth IRA Conversion and Valuation Strategies

32:58 - Audience Poll Results and Tax Strategy Discussion

35:24 - Land Man Show and Oil & Gas Realities

36:43 - Giveaway Announcement: Fire Yourself Book and Strategy Call

39:02 - Wealth Forum Event in Scottsdale Announcement

40:11 - Q&A: IRA-Owned LLC Prohibited Transactions

42:25 - Q&A: Concurrent Investments by Spouses in IRAs

44:39 - Q&A: Cost Segregation on Existing Properties

46:48 - Q&A: Oil Price Effects on Current Returns

48:07 - Q&A: UBIT/UDFI Filing and Leverage in Syndications

50:08 - Q&A: Self-Directed IRA Oil & Gas Investments

51:35 - Panelist Resources and Contact Info

53:43 - Outro and Next Event Teaser


Joint the Wealth Forum: bronsonequity.com/wealth


Connect with the Guests:


Yonah Weiss:

LinkedIn: https://www.linkedin.com/in/cost-segregation-yonah-weiss/

Website: https://www.yonahweiss.com/


Kaaren Hall:

Website: https://udirectira.com/

Email: [email protected]


Courtney Moeller

Email: [email protected]


#PrivateCredit

#TaxStrategies

#CostSegregation

#SelfDirectedIRA

#OilAndGasInvesting

#PassiveIncome

#RealEstate2026

...more
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Mailbox Money ShowBy Bronson Hill

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