New Money New Problems Podcast

NewMoneyNewProblems.com | New Money Solutions for New Money Problems

Negotiating compensation. Purchasing your first investment property. Helping your family with money. The highs and lows of entrepreneurship. New money leads to new problems that require new solutions. The NEW MONEY NEW PROBLEMS PODCAST tackles the financial topics our listeners are navigating for the first time, providing the expertise, interviews and resources for them to do so successfully.

  1. Should I Contribute To My Child's 529 If I'm Behind In My Own Planning? [REPLAY]

    4d ago

    Should I Contribute To My Child's 529 If I'm Behind In My Own Planning? [REPLAY]

    529 Plans vs. UTMA/UGMA and Brokerage Accounts: Choosing the Right Way to Save for Kids In this episode we explain how 529 plans work and why they can be powerful education-savings tools, highlighting tax-deferred growth, tax-free withdrawals for eligible education expenses, transferability to other family members, and high contribution limits including five-year front-loading. The biggest limitation is often the saver’s financial readiness, and many parents struggle to fund college meaningfully while juggling retirement, debt, housing goals, and other obligations. We discuss a Business Insider story about a couple weighing a 529 against a UTMA (and similar UGMA), outlining UTMA flexibility but potential tax issues and the automatic transfer of control to the child at adulthood, and explaining why the couple rejected both options and what they chose instead 00:00 529s And Alternatives 01:11 How 529s Work 02:57 Contribution Limits And Front Loading 04:39 When 529s Backfire 06:47 Rule Of Thumb 07:58 Break And Gap Finder 09:07 Case Study Katie And Husband 10:18 UTMA Basics And Risks 12:37 Why They Skipped 529 13:32 Brokerage Account Flexibility 14:21 Wrap Up And Takeaways Support the show

    15 min
  2. The (Huge) Risks Hidden In Your Insurance Policies

    May 22

    The (Huge) Risks Hidden In Your Insurance Policies

    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 Support the show

    35 min
  3. When Investment Real Estate Actually Works Pt. 2

    May 15

    When Investment Real Estate Actually Works Pt. 2

    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 Support the show

    26 min
  4. A Rental Property May Not Build Wealth. Here's Why.. (Part 1)

    May 8

    A Rental Property May Not Build Wealth. Here's Why.. (Part 1)

    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 Support the show

    20 min
  5. Student Loan Changes You Need To Know

    May 1

    Student Loan Changes You Need To Know

    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 Support the show

    17 min
  6. ... I Just Lost $33,709

    Apr 24

    ... I Just Lost $33,709

    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 Support the show

    30 min
  7. Third Thursdays | Safe Harbor Payments, Real Estate and Spousal IRAs

    Apr 17

    Third Thursdays | Safe Harbor Payments, Real Estate and Spousal IRAs

    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 Support the show

    27 min
  8. Financial Literacy Horror Stories

    Apr 10

    Financial Literacy Horror Stories

    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 Support the show

    23 min
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About

Negotiating compensation. Purchasing your first investment property. Helping your family with money. The highs and lows of entrepreneurship. New money leads to new problems that require new solutions. The NEW MONEY NEW PROBLEMS PODCAST tackles the financial topics our listeners are navigating for the first time, providing the expertise, interviews and resources for them to do so successfully.

Information

  • Creator
    NewMoneyNewProblems.com | New Money Solutions for New Money Problems
  • Years Active
    2022 - 2026
  • Episodes
    188
  • Rating
    Explicit
  • Copyright
    © 2026 New Money New Problems Podcast
  • Show Website
    New Money New Problems Podcast

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