New Money New Problems Podcast

EPISODE RESOURCES

Prizm Insurance

Property & Casualty Insurance for High Earners: Umbrella Coverage, Home/Auto Gaps (with Dave Olchowka)

In this episode, we host Dave Olchowka of Prizm Insurance to discuss why property and casualty insurance is often overlooked yet critical for high-income and affluent households. Dave shares his 20+ years in personal lines, his move from State Farm to the affluent/high net worth market, and why he built Prizm as a tech-enabled brokerage partnering with wealth advisors to streamline reviews while providing human advice. 

Dave contrasts captive agents vs brokers, then covers common coverage gaps: insufficient umbrella limits, inadequate home dwelling replacement-cost calculations, limited sewer/drain backup coverage, and weaknesses in standard auto policies (parts, valuation, and liability). 

Join us as we cover this crucial element of financial planning!

00:00 Why P&C Matters
00:49 Meet Dave and Prizm
04:27 Prism vs Captive Agents
07:30 Coverage Gaps for Affluent
11:51 Break and Gap Finder
13:01 Umbrella Insurance Basics
14:56 How Much Umbrella
17:44 Rental Property Coverage
19:20 Auto Coverage Details
22:12 Rental Cars and Turo
24:44 Home Renovations and Rebuild
27:53 Tough Markets Roof Rules
30:25 Why Pros Beat DIY
33:04 How to Contact Prism
33:58 Final Thanks and Wrap

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When Investment Real Estate Actually Works

In this episode, we break down when real estate can be an excellent wealth-building activity, contrasting last week’s case against owning one or two rentals.

We detail groups for whom real estate has low acquisition costs—military veterans using VA loans and medical/dental professionals using physician loans—and how it can make it easier to keep prior homes as rentals when moving. We then explain why real estate works better at scale, where strong properties can subsidize weaker ones and accumulated equity enables leverage via HELOCs, larger portfolio credit lines, and even securities-backed lines of credit to buy quickly with cash and refinance. Finally, we cover strategies requiring top-tier tax help, including short-term rental exceptions, the Augusta Rule, Real Estate Professional Status, and using depreciation, cost segregation, and bonus depreciation to create paper losses that can offset income.

00:00 When Real Estate Works
02:15 Low Down Payment Paths
03:37 Physician Loan Example
05:41 Building Portfolio Scale
07:27 Leverage With Credit Lines
11:59 Appreciation And Timing
14:19 Break And Gapfinder
15:29 Tax Strategy Overview
16:36 Short Term Rental Loopholes
17:48 Augusta Rule Explained
19:56 Real Estate Pro Status
21:18 Depreciation And Cost Seg
25:09 Wrap Up And Takeaways

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Why a Single Rental Property Often Disappoints High-Income Earners (Part 1)

Today we introduce a two-part series on rental property, and why a single rental property (or a couple) is often a poor wealth-building strategy for high-income earners. We cover how using a starter home as a rental can compromise upgrading to a better primary residence, using Brenton's childhood home as an example. We then show how difficult it is to produce meaningful cash flow after mortgage, taxes, insurance, maintenance, and property management, and preview part two, where we'll cover when real estate CAN work with certain elements in place (scale, early adoption, and/or real-estate-professional strategies).

00:00 Why Rentals Fail High Earners
00:46 Series Setup and Caveats
03:36 Turning Starter Home Into Rental
04:10 Down Payment Reality Check
06:15 Home Price Growth Trap
07:54 Cash Flow Math Doesn’t Work
11:54 Capital and Liquidity Tradeoff
14:34 Tax Benefits Are Overstated
15:19 Passive Loss Rules Explained
18:35 When Real Estate Works
19:39 Wrap Up and Part Two Tease

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EPISODE RESOURCES

RISE Student Loan Regulations Fact Sheet

...I Just Lost $33,709 Episode

Repayment Assistance Plan Explained

Finalized DOE Student Loan Rules: New Caps, Repayment Assistance Plan, and Default Rehab Changes (Effective 2026–2027)

In this episode we share newly finalized Department of Education regulations tied to the Working Families Tax Cuts Act and explain how they may affect student loan borrowers starting in 2026–2027. We outline new federal loan caps beginning July 1, 2026: graduate loans limited to $20,500 annually/$100,000 total; professional programs (11 fields including law, medicine, dentistry, and clinical psychology) to $50,000 annually/$200,000 total; and Parent PLUS capped at $20,000 annually/$65,000 per dependent, plus a $257,500 lifetime limit for new borrowers. We also cover repayment changes including a new Repayment Assistance Plan becoming the only income-driven option for first-time borrowers after July 1, 2026, a tiered 10–25 year standard plan, expanded loan rehabilitation to twice per loan with IDR opt-in at agreement signing, revised forbearance limits, sunsetting certain deferments for loans after July 1, 2027, and new institutional and part-time borrowing rules, warning current borrowers to be cautious about taking new loans.

00:00 Student Loan Rule Update
00:08 Podcast Intro and Context
01:21 Personal IRS Refund Story
02:02 New DOE Regulations Overview
02:50 Graduate and Professional Loan Caps
05:19 Parent PLUS Limits Explained
07:36 Lifetime Borrowing Cap
08:20 New Repayment Plan Changes
09:43 Tiered Standard Repayment
11:07 Default Loan Rehabilitation Updates
13:30 Forbearance and Deferment Changes
14:27 School and Part Time Loan Limits
15:41 Key Takeaways and Wrap Up

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How I Accidentally Double-Paid the IRS $33,709—and Covered the Cash Crunch

In this episode, Brenton recounts misplacing $33,709 after accidentally paying his 2025 taxes twice: he walks through how to make IRS payments and check refund status, noting refunds may take 21+ days and planning for up to 90 days. He describes telling his wife and their strained cash position due to her nine-month unemployment and higher expenses. He evaluates liquidity options (brokerage sale taxes, retirement penalties, Roth contributions limits, credit strategies, life insurance withdrawals/loans, securities-backed LOC minimums) and walks through the option he chose and why it was most appropriate.

01:47 Overdraft Shock
02:25 Tax Planning Routine
04:57 Double Payment Mistake
05:49 IRS Payment Walkthrough
08:58 Ad Break
10:07 Telling My Wife
11:14 Refund Timeline Check
13:09 Emergency Fund Reality
15:31 Where To Pull Cash
17:38 Credit Card Strategy
22:18 Leverage Options Review
29:20 Lessons And Wrap Up

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EPISODE RESOURCES

Subscribe to our YouTube channel!

Repayment Assistance Plan Explained

2026 IRS Tax Tables

Real Estate Professional Status Requirements

IRS Passive Activity Rules

Third Thursday Preview: IRS Delays, Safe Harbor Payments, and the Hidden Context Behind Tax-Saving TikToks

In this episode, we preview content from our “Third Thursday” YouTube series, where we add some context to the financial content you see on social media. We review a TikTok about IRS staffing cuts, longer wait times, and delayed processing, using it to introduce the concept of safe harbor payments for people who risk paying tax penalties for underwithholding throughout the year. We cover safe harbor payments and the two strategies that can be used to keep yourself out of the IRS' crosshairs.. We then critique a viral “save $60,000 in taxes” video for missing context, covering startup loss limits (hobby loss rule), the IRS's definition of a Real Estate Professional and how it benefits your taxes, the practical limits of maxing retirement accounts, and spousal IRA deduction phaseouts tied to adjusted gross income.

00:00 Series Preview Intro
00:47 Behind the Scenes Update
01:49 Third Thursday Format
03:18 IRS Staffing TikTok
05:34 Safe Harbor Basics
08:07 Two Safe Harbor Rules
10:10 Safer Payment Tactics
11:53 Marriage Tax Hack Video
14:50 Context for Four Couples
14:56 Founder Losses and Risks
17:10 Real Estate Pro Status
20:44 Freelancer Retirement Limits
21:56 Spousal IRA Phaseouts
25:46 Final Takeaways and Wrap

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EPISODE RESOURCES

Register for the Financial Symposium!

Check out the Change of Plans Checklist

Financial Literacy Month Horror Stories: Credit, Taxes, Insurance, Investing, and Estate Planning Mistakes

In honor of April being Financial Literacy Month, we share de-identified “horror stories” from real client experiences to show how small financial mistakes can create major consequences. You'll hear the dangers of co-signing loans, highlighting a divorce scenario where an overlooked private student loan left a co-signer responsible after the ex-spouse defaulted. We also tell a frightening tale of a homeowner whose seemingly small decision to close a card cost them over $150,000! On taxes, we recount a sale where an incorrect report of an investment sale doubled a client's tax bill and took over 6 months to correct. Taxes, Estate planning, investments: plenty of spooky stories for all.

TUNE IN!

00:00 Financial Literacy Horror Stories
00:56 Why April Matters
02:18 Cosigning Gone Wrong
05:12 Credit Mistakes Before Closing
08:20 Tax Return Cost Basis Error
10:32 Gap Finder Break
11:41 Insurance Policy Surprise
13:54 REIT Taxes Explained
16:10 Net Unrealized Appreciation
18:29 Estate Planning Pitfalls
21:31 Final Takeaways and Event

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EPISODE RESOURCES

SAVE Plan Cancellation Press Release

SAVE Plan Timeline Press Release

Parent Plus Loan D-Day, Disallowed Student Loan Guidelines and Details on the Immediate Future of the SAVE Plan

In this episode, we go through EXTREMELY important details on the future of Parent Plus Loans, and why many borrowers need to take action by April 1st in order to preserve eligibility for student loan forgiveness. These borrowers must have a newly consolidated loan disbursed by July 1st to maintain eligibility, and all parents should be wary of borrowing any new Parent Plus Loans after that time. We also cover certain student loan guidelines from the Biden era that have been disallowed, including, crucially, the ability to consolidate federal loans without resetting your credit towards forgiveness. Lastly, for borrowers on the SAVE plan, we have details on the 90 day timeline borrowers will have to move to a new Income Driven Repayment plan or risk being placed on a (likely significantly higher) Standard Plan. Tune in for details!

00:00 Emergency Student Loan Alert
00:49 Why A Midweek Episode
02:17 Parent Plus Deadline Explained
02:42 How To Consolidate Correctly
05:27 July 1 Rule Changes Warning
07:44 SAVE Plan Closure Update
09:12 Consolidation Credits Reset
12:08 Defaulted Borrowers Options
13:45 What Good News Remains
15:45 PSLF Buyback Clarified
18:20 SAVE Exit Timeline July 1
20:51 Wrap Up And Next Steps

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EPISODE RESOURCES

Register for the Riverside Financial Literacy Symposium!

Try the Change of Plans Checklist!

How Much Life Insurance Do I Need Episode

Life Insurance Needs Calculator

Insurance Essentials for Families: Home, Auto, Umbrella, Health, Disability, Life & Long-Term Care

In this episode we discuss the key insurance types every person should consider. We review property-related protections—auto, renters insurance, and the various elements of homeowners insurance. Brenton explains umbrella policies as inexpensive additional liability protection, and then cover personal insurances: the necessity of health insurance despite high marketplace costs, long-term disability as paycheck protection (including group-policy tax and income-definition gaps), life insurance needs often being underestimated and requiring calculators and appropriate term length, and long-term care insurance to protect assets and avoid Medicaid impoverishment.

Tune in!

00:00 Why Insurance Matters
00:40 Podcast Intro and Updates
01:04 Symposium Invitation
01:59 Episode Roadmap
03:04 Auto Coverage Basics
04:09 Renters Insurance Essentials
05:17 Homeowners Policy Breakdown
11:51 Umbrella Liability Protection
14:37 Break and Gap Finder
15:43 Health Insurance Reality Check
18:05 Disability Paycheck Protection
22:15 Life Insurance Sizing
24:04 Long Term Care Planning
28:52 Wrap Up and Next Steps

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EPISODE RESOURCES

The Change of Plans Checklist

The Holmes-Rahe Life Stress Inventory

Toni Collier's Money Story

Change of Plans Checklist PLUS Navigating the Financial Fallout of Divorce

Join us as we introduce the New Money New Problems Change of Plans Checklist, inspired by recent life upheavals and the Holmes–Rahe stress scale.in this episode, we discuss how both positive and negative life events can drive significant stress and financial consequences. 

We walk through the interactive checklist at newmoneynewproblems.com/changeofplans, which maps 52 life events across eight sections to impacted financial areas—taxes, investments, insurance, employee benefits, estate planning, and student loans—and assigns urgency levels (yellow, orange, red). We then demo the checklist while illustrating the changes from a pending divorce and outlines key actions.

Whether life changes big or small, positive or negative, try out the checklist and share it with those you love!

00:00 Life Events Money Impact
01:16 Why This Checklist Exists
02:17 Stress Scale Wake Up Call
05:17 Checklist Demo Overview
06:13 All Life Event Categories
08:56 Break And Gap Finder
09:45 Divorce Case Study Setup
10:12 Divorce Taxes And Filing
12:10 Insurance And Benefits Changes
14:30 Investments And QDROs
16:30 Estate Plan After Divorce
18:18 Student Loans Divorce Fallout
22:01 Summary PDF And Resources
23:29 How To Use And Share

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