Podcast
New Money New Problems Podcast
Hosted by NewMoneyNewProblems.com | New Money Solutions for New Money Problems · EN
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.
29episodes
Episodes
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The (Huge) Risks Hidden In Your Insurance Policies
2w ago00:34:36Tap to summarizeEPISODE RESOURCESPrizm InsuranceProperty & 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 Matters00:49 Meet Dave and Prizm04:27 Prism vs Captive Agents07:30 Coverage Gaps for Affluent11:51 Break and Gap Finder13:01 Umbrella Insurance Basics14:56 How Much Umbrella17:44 Rental Property Coverage19:20 Auto Coverage Details22:12 Rental Cars and Turo24:44 Home Renovations and Rebuild27:53 Tough Markets Roof Rules30:25 Why Pros Beat DIY33:04 How to Contact Prism33:58 Final Thanks and WrapSupport the show
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When Investment Real Estate Actually Works Pt. 2
3w ago00:26:11Tap to summarizeWhen Investment Real Estate Actually WorksIn 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 Works02:15 Low Down Payment Paths03:37 Physician Loan Example05:41 Building Portfolio Scale07:27 Leverage With Credit Lines11:59 Appreciation And Timing14:19 Break And Gapfinder15:29 Tax Strategy Overview16:36 Short Term Rental Loopholes17:48 Augusta Rule Explained19:56 Real Estate Pro Status21:18 Depreciation And Cost Seg25:09 Wrap Up And TakeawaysSupport the show
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A Rental Property May Not Build Wealth. Here's Why.. (Part 1)
4w ago00:20:20Tap to summarizeWhy 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 Earners00:46 Series Setup and Caveats03:36 Turning Starter Home Into Rental04:10 Down Payment Reality Check06:15 Home Price Growth Trap07:54 Cash Flow Math Doesn’t Work11:54 Capital and Liquidity Tradeoff14:34 Tax Benefits Are Overstated15:19 Passive Loss Rules Explained18:35 When Real Estate Works19:39 Wrap Up and Part Two TeaseSupport the show
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Student Loan Changes You Need To Know
May 100:17:21Tap to summarizeEPISODE RESOURCESRISE Student Loan Regulations Fact Sheet...I Just Lost $33,709 EpisodeRepayment Assistance Plan ExplainedFinalized 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 Update00:08 Podcast Intro and Context01:21 Personal IRS Refund Story02:02 New DOE Regulations Overview02:50 Graduate and Professional Loan Caps05:19 Parent PLUS Limits Explained07:36 Lifetime Borrowing Cap08:20 New Repayment Plan Changes09:43 Tiered Standard Repayment11:07 Default Loan Rehabilitation Updates13:30 Forbearance and Deferment Changes14:27 School and Part Time Loan Limits15:41 Key Takeaways and Wrap UpSupport the show
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... I Just Lost $33,709
Apr 2400:30:27Tap to summarizeHow I Accidentally Double-Paid the IRS $33,709—and Covered the Cash CrunchIn 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 Shock02:25 Tax Planning Routine04:57 Double Payment Mistake05:49 IRS Payment Walkthrough08:58 Ad Break10:07 Telling My Wife11:14 Refund Timeline Check13:09 Emergency Fund Reality15:31 Where To Pull Cash17:38 Credit Card Strategy22:18 Leverage Options Review29:20 Lessons And Wrap UpSupport the show
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Third Thursdays | Safe Harbor Payments, Real Estate and Spousal IRAs
Apr 1700:27:07Tap to summarizeEPISODE RESOURCESSubscribe to our YouTube channel!Repayment Assistance Plan Explained2026 IRS Tax TablesReal Estate Professional Status RequirementsIRS Passive Activity RulesThird Thursday Preview: IRS Delays, Safe Harbor Payments, and the Hidden Context Behind Tax-Saving TikToksIn 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 Intro00:47 Behind the Scenes Update01:49 Third Thursday Format03:18 IRS Staffing TikTok05:34 Safe Harbor Basics08:07 Two Safe Harbor Rules10:10 Safer Payment Tactics11:53 Marriage Tax Hack Video14:50 Context for Four Couples14:56 Founder Losses and Risks17:10 Real Estate Pro Status20:44 Freelancer Retirement Limits21:56 Spousal IRA Phaseouts25:46 Final Takeaways and WrapSupport the show
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Financial Literacy Horror Stories
Apr 1000:23:07Tap to summarizeEPISODE RESOURCESRegister for the Financial Symposium!Check out the Change of Plans ChecklistFinancial Literacy Month Horror Stories: Credit, Taxes, Insurance, Investing, and Estate Planning MistakesIn 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 Stories00:56 Why April Matters02:18 Cosigning Gone Wrong05:12 Credit Mistakes Before Closing08:20 Tax Return Cost Basis Error10:32 Gap Finder Break11:41 Insurance Policy Surprise13:54 REIT Taxes Explained16:10 Net Unrealized Appreciation18:29 Estate Planning Pitfalls21:31 Final Takeaways and EventSupport the show
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EMERGENCY STUDENT LOAN EPISODE!
Apr 100:22:07Tap to summarizeEPISODE RESOURCESSAVE Plan Cancellation Press ReleaseSAVE Plan Timeline Press ReleaseParent Plus Loan D-Day, Disallowed Student Loan Guidelines and Details on the Immediate Future of the SAVE PlanIn 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 Alert00:49 Why A Midweek Episode02:17 Parent Plus Deadline Explained02:42 How To Consolidate Correctly05:27 July 1 Rule Changes Warning07:44 SAVE Plan Closure Update09:12 Consolidation Credits Reset12:08 Defaulted Borrowers Options13:45 What Good News Remains15:45 PSLF Buyback Clarified18:20 SAVE Exit Timeline July 120:51 Wrap Up And Next StepsSupport the show
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The Types of Insurance Every Person Needs
Mar 2700:30:03Tap to summarizeEPISODE RESOURCESRegister for the Riverside Financial Literacy Symposium!Try the Change of Plans Checklist!How Much Life Insurance Do I Need EpisodeLife Insurance Needs CalculatorInsurance Essentials for Families: Home, Auto, Umbrella, Health, Disability, Life & Long-Term CareIn 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 Matters00:40 Podcast Intro and Updates01:04 Symposium Invitation01:59 Episode Roadmap03:04 Auto Coverage Basics04:09 Renters Insurance Essentials05:17 Homeowners Policy Breakdown11:51 Umbrella Liability Protection14:37 Break and Gap Finder15:43 Health Insurance Reality Check18:05 Disability Paycheck Protection22:15 Life Insurance Sizing24:04 Long Term Care Planning28:52 Wrap Up and Next StepsSupport the show
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The Change of Plans Checklist
Mar 2000:24:25Tap to summarizeEPISODE RESOURCESThe Change of Plans ChecklistThe Holmes-Rahe Life Stress InventoryToni Collier's Money StoryChange of Plans Checklist PLUS Navigating the Financial Fallout of DivorceJoin 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 Impact01:16 Why This Checklist Exists02:17 Stress Scale Wake Up Call05:17 Checklist Demo Overview06:13 All Life Event Categories08:56 Break And Gap Finder09:45 Divorce Case Study Setup10:12 Divorce Taxes And Filing12:10 Insurance And Benefits Changes14:30 Investments And QDROs16:30 Estate Plan After Divorce18:18 Student Loans Divorce Fallout22:01 Summary PDF And Resources23:29 How To Use And ShareSupport the show
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