Jonathan On Money

By Jonathan On Money

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Category: Investing

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Episodes: 171

Description

Jonathan On Money explores various timely topics in personal finance and its intersection with Jewish life. Join Jonathan I. Shenkman, President & Chief Investment Officer of ParkBridge Wealth Management as he covers topics in investing, behavioral finance, estate planning, financial planning, taxes, insurance and more. Each show is packed with practical and actionable information.


A must listen for all investors (especially Jewish ones) looking to be more intentional with their money. Also a great source of content for practitioners in the field of wealth management. This includes trust & estate attorneys, accountants, tax advisors, financial planners, insurance professionals, trust officers, and portfolio managers.



Securities offered through Kestra Investment Services, LLC, (Kestra IS), member FINRA/SIPC. Investment Advisory Services offered through Kestra Advisory Services, LLC, (Kestra AS) an affiliate of Kestra IS. “ParkBridge Wealth Management” is not affiliated with Kestra IS or Kestra AS. https://www.kestrafinancial.com/disclosures


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Episode Date
Episode 171: Financial Survival for the Sandwich Generation, Responsibilities Of Trustees, & Portfolio Perfection
Jul 29, 2026
Episode 170: Trump Accounts, Prenups, & Economic Challenges Facing Our Youth
Jul 22, 2026
Episode 169: Nine Days-Nine Lessons, Single Stock ETFs, & Multiple Retirement Plan Rules
Jul 15, 2026
Episode 168: America At 250, Jewish Financiers Who Helped Build a Nation, and Investing in Apple Pie & BBQs
Jul 08, 2026
Episode 167: IN FOCUS: Mid-Year Money Check-In - The 2026 Trends That Are Impacting Your Wealth
Jul 01, 2026
Episode 166: Ultimate Advice For Recent Grads, Investing In Films, & Giving up a 2.75% Mortgage
Jun 24, 2026
Episode 165: IN FOCUS: How to Discharge IRS and NYS Tax Liens with Scott Kestenbaum and Jill Monoson (Kestenbaum & Mark)
Jun 17, 2026
Episode 164: Managing Bar Mitzvah Money, Are Backdoor Roth IRAs Immoral, Professionals That Are The Worst At Managing Money
Jun 10, 2026
Episode 163: IN FOCUS: Designing Resilient Estate Plans - Planning to Avoid Litigation with Asher Lowenstein (Lowenstein Legal)
Jun 03, 2026
Episode 162: Gambling, Gold, Advisory Fees, And Why Dividend Yields Are Falling
May 27, 2026
Episode 161: IN FOCUS: Hot Topics in State Tax Residency - Audit Enforcement and Wealth Taxes with Tim Noonan (Hodgson Russ)
May 20, 2026
Episode 160: Ten Commandments For Retirement Readiness, Negotiating A Higher Salary, Scheduling Happiness, & Planning For Gvirim
May 13, 2026
Episode 159: IN FOCUS: Qualified Charitable Distributions: Rules, Opportunities, and Tax Traps with Lisa Presser and Brian Balduzzi (Faegre Drinker)
May 06, 2026
Episode 158: Affording The Five Towns, Inherited Real Estate, Dress To Impress, & High Returns Using ETFs
Apr 29, 2026
Episode 157: IN FOCUS: When the Family Is the Business - Why You Need a Real Partnership Agreement with Av Sinensky (Falcon Rappaport & Berkman)
Apr 22, 2026
Episode 156: Pesach Programs, Reinvesting Dividends, and Are Teachers Underpaid
Apr 15, 2026
Episode 155: IN FOCUS: Retirement 2.0 - Modern Planning Strategies for 2026
Apr 07, 2026
Episode 154: The Seder & Investing, Retiring Into a Down Stock Market, Working With A $400 million Client
Mar 31, 2026
Episode 153: IN FOCUS: Highlights of the 2026 Heckerling Institute on Estate Planning with Kevin Matz (ArentFox Schiff)
Mar 25, 2026
Episode 152: Annuity vs Lump Sum Payment, Does Your Yeshiva Have A Good 401(k) & My Best Purchase For Under $100
Mar 18, 2026
Episode 151: IN FOCUS: How to Shift CRT Benefits to Children Under Today’s Tax Rules with Evan Unzelman (CRT Experts)
Mar 11, 2026
Episode 150: Tax Strategies For Irrevocable Trusts & Hidden Financial Lessons From The Megillah
Mar 04, 2026
Episode 149: Financial Advisors That Should Be Put In Cherem, Money Advice for Travis & Taylor, and Wyoming Holding LLC
Feb 25, 2026
Episode 148: IN FOCUS: Escape from New York - Tax & Estate Planning Considerations For Moving To Florida Or Israel with Boaz Feinberg and Lawrence Garbuz
Feb 18, 2026
Episode 147: How Much To Spend On A Chassan Watch, Tradeoffs, ROI of Baha Mar & All You Can Eat Buffets
Feb 11, 2026
Episode 146: IN FOCUS: Overcoming Estate and Elder Care Planning Hurdles with Elizabeth Forspan (Forspan Klear)
Feb 04, 2026
Episode 145: Investing In AI, Raising Money Smart Kids, and Investing In Israel vs. Palestine
Jan 28, 2026
Episode 144: How Much To Spend on a Date, Dave Ramsey On Choices, & Are Vanguard's Fees Compelling?
Jan 21, 2026
Episode 143: IN FOCUS: Asset Protection in 2026 - SLATs, DAPTs, SPATs and more Acronyms with Marty Shenkman (Shenkman Teitz)
Jan 14, 2026
Episode 142: Trump Accounts, Marriage & Money, and The Next Recession
Jan 07, 2026
Episode 141: Does The Principal Of Your Child's School Make Too Much Money, Chris Rock On Wealth, & Capitalism vs. Socialism
Dec 31, 2025
Episode 140: IN FOCUS: Asset Protection and Personal Guaranties with Eli Akhavan (Grant, Herrmann, Schwartz & Klinger)
Dec 24, 2025
Episode 139: The Frum Community Has a Spending Problem, Chosson Gifts, Annuities, & Chizzuk From Jerry Rice
Dec 17, 2025
Episode 138: IN FOCUS: 2025 Last Minute Wealth Planning Ideas with Jonathan Shenkman (ParkBridge Wealth)
Dec 10, 2025
Episode 137: IN FOCUS: Legal Protections for Vulnerable Young Adults with Amy O'Hara (Littman Krooks)
Dec 03, 2025
Episode 136: What I'm Thankful For, Buffet’s Farwell, & Investing In Friend's Real Estate "Deal"
Nov 26, 2025
Episode 135: IN FOCUS: Business and Real Estate Succession Planning with Avi Kestenbaum (Meltzer, Lippe)
Nov 19, 2025
Episode 134: Don't Patschke With Your Money, Investing Missteps When Rates Fall, & The Impact of AI On Your Job
Nov 12, 2025
Episode 133: IN FOCUS: State Income Taxation Of Trusts with Andrew Katzenberg (ArentFox Schiff)
Nov 05, 2025
Episode 132: The Financial Lesson From The Great Flood, Roth IRA Conversions In Retirement, & Chiddushim From Mother Teresa
Oct 29, 2025
Episode 131: IN FOCUS: Structuring Buy-Sell Agreements Right with Jack Elder (Kestra Insurance Planning)
Oct 22, 2025
Episode 130: Non-Financial Retirement Considerations, Private Assets in ETFs, & My Weekly Family Financial Strategy Session
Oct 16, 2025
Episode 129: Trump's Performance, Your Friends Are Holding You Back, & Developing Content
Oct 09, 2025
Episode 128: Rules For Contributing To Multiple Retirement Accounts & Forecasting Your Future Tax Rate
Oct 01, 2025
Episode 127: IN FOCUS: Snowbird Domicile and Choice Of Law with Bruce Steiner (Kleinberg, Kaplan)
Sep 25, 2025
Episode 126: Getting By On Only 400K, Giving With A Warm Hand, And Is It Permitted To Buy German Products
Sep 17, 2025
Episode 125: IN FOCUS: Tax Issues with Distressed Real Estate with Matthew E. Rappaport (Falcon Rappaport & Berkman LLP)
Sep 10, 2025
Episode 124: Summer Road Trip, The Pursuit Of Investment Perfection, and Making Aliyah With No Job
Sep 03, 2025
Episode 123: Dumb Kiddush Club Advice, Leaving A Legacy, & Not Living Life In The Rearview Mirror
Aug 27, 2025
Episode 122: Tariffs & Inequality, Marketing Tips, Trump/Putin Summit, and How to Panic Prudently
Aug 20, 2025
Episode 121: Commercial Real Estate, Managing A Financial Windfall, & Sports Betting Within Your Portfolio
Aug 13, 2025
Episode 120: Morning Routines, ROI on Pesach Getaways, Birthday Parties & 529 Accounts, and Financial Wisdom From Proverbs
Aug 06, 2025
Episode 119: How Do We Get Yeshivas To Stop Raising The Price Of Tuition?
Jul 30, 2025
Episode 118: IN FOCUS: One Big Beautiful Bill Act - Overview & Planning Ideas with Marty Shenkman (Shenkman Law)
Jul 23, 2025
Episode 117: Solving The Yeshiva Tuition Crisis By Signing "The Yeshiva Pledge"
Jul 16, 2025
Episode 116: Should I Wait To Purchase A Home Given The High Rates And High Prices?
Jul 09, 2025
Episode 115: Should I Invest In A Restaurant?
Jul 02, 2025
Episode 114: IN FOCUS: Is ESG Investing A Marketing Ploy with Jonathan Shenkman (ParkBridge Wealth)
Jun 25, 2025
Episode 113: Do I Need A Crypto Coach?
Jun 18, 2025
Episode 112: IN FOCUS: Understanding Pass-Through Entity Taxation with Angelika Herburger and Russell Ephraim (CBIZ Advisors)
Jun 11, 2025
Episode 111: Ten Financial Commandments For Retirees
Jun 04, 2025
Episode 110: IN FOCUS: Gifts and Bequests from Covered Expatriates with John Kiely (McDermott Will & Emery)
May 28, 2025
Episode 109: How I Found My Bashert & Manage My Money
May 21, 2025
Episode 108: IN FOCUS: Hot Topics in NY Tax Audits and Enforcement with Timothy Noonan (Hodgson Russ)
May 14, 2025
Episode 107: Taking Out Credit Card Debt To Pay For A Wedding
May 07, 2025
Episode 106: IN FOCUS: Over-Looked Estate Planning Tips to Consider for 2025 with Brian Balduzzi and Lisa Presser (Faegre Drinker)
Apr 30, 2025
Episode 105: Financial Considerations Before Making Aliyah
Apr 23, 2025
Episode 104: The Passover Paradox
Apr 16, 2025
Episode 103: Life and Investing Wisdom from Confucius & George Carlin
Apr 09, 2025
Episode 102: IN FOCUS: Common Mistakes Wealthy Families Make with Jonathan Shenkman (ParkBridge Wealth)
Apr 02, 2025
Episode 101: Tariffs: Should Retirees Be Concerned?
Mar 26, 2025
Episode 100: IN FOCUS: Form 3520 Reporting Under The Proposed Regulations
Mar 19, 2025
Episode 99: Reconsider Your Spending On Purim
Mar 12, 2025
Episode 98: IN FOCUS: Highlights of the 2025 Heckerling Institute on Estate Planning
Mar 05, 2025
Episode 97: Should My Roth IRA Be Invested Differently Than My Traditional IRA?
Feb 26, 2025
Episode 96: IN FOCUS: Tax Implications of Merger and Acquisition Transactions
Feb 19, 2025
Episode 95: A Shtickle Rant
Feb 12, 2025
Episode 94: IN FOCUS: Where Good Estate Planning Equals Poor Elder Care Planning
Feb 05, 2025
Episode 93: Tax Season Is Upon Us
Jan 29, 2025
Episode 92: The "401(k) Trap"
Jan 22, 2025
Episode 91: IN FOCUS: Post-Election: The New World of Estate Planning
Jan 15, 2025
Episode 90: 7 Predictions For The Year-Ahead
Jan 08, 2025
Episode 89: IN FOCUS: International Taxation Law in Israel: Are Your Client’s Prepared for the New and Evolving Rules?
Jan 01, 2025
Episode 88: Success Lies In The Relentless Execution Of The Basics
Dec 25, 2024
Episode 87: IN FOCUS: Fundamentals of SSI, SSDI, Medicaid and Medicare Eligibility
Dec 18, 2024
Episode 86: Should I Sell My Rental Home and Invest The Proceeds In The Market?
Dec 11, 2024
Episode 85: IN FOCUS: Last Minute 2024 Wealth Planning Ideas - Ensuring Your Clients Make the Right Moves Before Year-End
Dec 04, 2024
Episode 84: IN FOCUS: To Trust or Not to Trust: A Tutorial on Trust Planning for Wealthy Families & Their Advisors
Nov 27, 2024
Episode 83: Where Do I Park My Cash Now?
Nov 20, 2024
Episode 82: IN FOCUS: “International Estate Planning - Traps for the Unwary"
Nov 13, 2024
Episode 81: New President! What Now?
Nov 06, 2024
Episode 80: IN FOCUS: "Generation-Skipping Transfer Tax Tricks and Traps”
Oct 30, 2024
Episode 79: Should I mimic the investment strategies of politicians?
Oct 23, 2024
Episode 78: IN FOCUS: "Going to the Sunshine State? Tax Considerations in Florida Planning”
Oct 16, 2024
Episode 77: A Time For Spiritual & Financial Introspection
Oct 09, 2024
Episode 76: IN FOCUS: "Charitable Giving: Timely Strategies and Considerations Under Jewish Law"
Oct 02, 2024
Episode 75: What Percentage of My Portfolio Should Be In Alternative Investments?
Sep 25, 2024
Episode 74: IN FOCUS: “Estate Planning If You have Assets/Heirs In Israel"
Sep 18, 2024
Episode 73: Human Financial Advisor vs. Robo Advisor
Sep 11, 2024
Episode 72: Paying For A Wedding When Machatanim Disagree
Sep 04, 2024
Episode 71: Strategies For Getting Laid Off Before You’re Ready To Retire
Aug 28, 2024
Episode 70: Money Lessons From The Olympics
Aug 21, 2024
Episode 69: The Destruction of Wealth
Aug 13, 2024
Episode 68: How many pages should a financial plan be?
Aug 07, 2024
Episode 67: Should I loan money to a relative?
Jul 31, 2024
Episode 66: Should I borrow money from my 401k to invest in real estate?
Jul 24, 2024
Episode 65: HOT TOPICS with Martin Shenkman (Connely, ESG, Step transactions, Direct indexing, and CTA developments)
Jul 17, 2024
Episode 64: Rockefeller on Giving
Jul 10, 2024
Episode 63: IN FOCUS: “Children & Money: Timeless Strategies To Transmit to The Next Generation”
Jul 03, 2024
Episode 62: Personal Finances Lessons For All The Dads Out There!
Jun 26, 2024
Episode 61: IN FOCUS: “Marital Miss: The Importance of Planning, Preparing and Protecting for Families Before (and After) a Loved One Marries”
Jun 19, 2024
Episode 60: Thoughts on Universal Basic Income
Jun 14, 2024
Episode 59: IN FOCUS: “Qualifying as Qualified Small Business Stock (Section 1202)”
Jun 05, 2024
Episode 58: The Summer Financial Challenge
May 29, 2024
Episode 57: IN FOCUS: “Unraveling the Challenges in Estate Planning: Navigating Copyright Law and Preserving Creator Intent”
May 22, 2024
Episode 56: ParkBridge Turns Two! Reflections On Being a Business Owner
May 15, 2024
Episode 55: IN FOCUS: “Hot Topics in NYS/NYC Residency and Personal Income Taxes”
May 08, 2024
Episode 54: The Intersection of Psychology and Investing
May 01, 2024
Episode 53: IN FOCUS: “The Latest and Greatest in Aggressive Tax Strategies"
Apr 25, 2024
Episode 52: Today Is My Birthday! 39 Personal Finance Lessons In Honor Of My 39th Birthday
Apr 17, 2024
Episode 51: Personal Finance Rules Of Thumb (With A Frum Twist)
Apr 10, 2024
Episode 50: Are Annuities A Good Investment?
Apr 03, 2024
Episode 49: ESG investing - Matching Investors Portfolios With Their Values.
Mar 27, 2024
Episode 48: IN FOCUS: “Women and Wealth: Challenges and Strategies for Female Clients"
Mar 20, 2024
Episode 47: Money lessons from the Golden Calf, Vanderbilts, And Touro Synagogue
Mar 13, 2024
Episode 46: IN FOCUS: “Estate Planning for U.S. Clients who own assets and/or have descendants in other countries (with a special focus on Israel)”
Mar 06, 2024
Episode 45: The Most Important Financial Decision: Who You Decide To Marry
Feb 28, 2024
Episode 44: IN FOCUS: “CRTs as “Stretch IRA” Substitutes”
Feb 21, 2024
Episode 43: Solving the College Tuition Puzzle
Feb 14, 2024
Episode 42: IN FOCUS: “Spousal Lifetime Access Trusts for Mass Affluent ($1-10M) taxpayers”
Feb 07, 2024
Episode 41: Is Spending Yeshiva Break In Florida Financially Prudent?
Jan 31, 2024
Episode 40: IN FOCUS: “Use it or Lose it - Securing the use of the $13 Million+ Federal Estate, Gift and GST Tax Exemptions before Sunset”
Jan 24, 2024
Episode 39: Should I Pay For The Young Couple’s Shana Rishona In Israel
Jan 17, 2024
Episode 38: IN FOCUS: “Long Term Care Costs and Options at Varying Degrees of Wealth”
Jan 10, 2024
Episode 37: 6 Strategies to Lower Your Taxes in Retirement
Jan 03, 2024
Episode 36: Seven Ways To Invest In Israel Today Given The War In Gaza
Dec 27, 2023
Episode 35: IN FOCUS: “Selecting an Asset Protection Plan – Strategies and Pitfalls”
Dec 20, 2023
Episode 34: Is College Still A Good Investment?
Dec 13, 2023
Episode 33: IN FOCUS: “Last Minute 2023 Wealth Planning Ideas”
Dec 06, 2023
Episode 32: A Time To Be Thankful
Nov 29, 2023
Episode 31: The most pressing financial issues facing the frum community today
Nov 22, 2023
Episode 30: IN FOCUS: “Moving to Israel: Top Financial Planning Considerations”
Nov 15, 2023
Episode 29: Get out of your own way!
Nov 08, 2023
Episode 28: IN FOCUS: “Selling a Family Business: Legal, Financial, and Estate Planning Considerations”
Nov 01, 2023
Episode 27: Making it to Boca!
Oct 25, 2023
Episode 26: IN FOCUS: "“Taxation of Supplemental Needs Trusts"
Oct 18, 2023
Episode 25: Back To The Basics: Investing Is Like A Birthday Cake
Oct 11, 2023
Episode 24: IN FOCUS: "Planning Under SECURE 2.0 and the Proposed Regulations”
Oct 04, 2023
Episode 23: What Dave Ramsey Got Wrong
Sep 27, 2023
Episode 22: IN FOCUS: “A Practical Guide on the Lifecycle of Planning for Art Collections”
Sep 20, 2023
Episode 21: Reflecting On The Past Year: 6 Lessons For Investing And Life
Sep 13, 2023
Episode 20: Money Advice Every Parent Should Give Their Children
Sep 06, 2023
Episode 19: Affording A Frum Lifestyle and Living Your Rich Life
Aug 30, 2023
Episode 18: Affording A Frum Lifestyle - A Proactive Approach
Aug 23, 2023
Episode 17: Supporting Kollel Kids And Retirement
Aug 16, 2023
Episode 16: IN FOCUS: “Taxation of Cryptocurrency, NFTs, and Decentralized Finance”
Aug 09, 2023
Episode 15: My Thoughts On Dave Ramsey’s Seven Baby Steps
Aug 02, 2023
Episode 14: IN FOCUS: "Financial Planning For Orthodox Jewish Families: There Is Nothing Average About a Frum Lifestyle”
Jul 26, 2023
Episode 13: Should I Incur Credit Card Debt To Pay Yeshiva Tuition?
Jul 19, 2023
Episode 12: IN FOCUS: “Using Tax Insurance to Achieve Tax Certainty in Estate Planning and Wealth Management”
Jul 12, 2023
Episode 11: Proud to be an American Investor
Jul 05, 2023
Episode 10: IN FOCUS: "Ten Timeless Investing Principles and How They Apply in Today’s Market"
Jun 28, 2023
Episode 9: Financial Planning For LGBTQ Families
Jun 21, 2023
Episode 8: IN FOCUS: "Private Foundations: The 5 deadly sins (or excises taxes)”
Jun 14, 2023
Episode 7: The Dangers of a Kiddush Club Portfolio
Jun 07, 2023
Episode 6: IN FOCUS: “U.S. beneficiaries of Canadian estates"
May 31, 2023
Episode 5: Do I Have Enough Life Insurance?
May 24, 2023
Episode 4: IN FOCUS: "Coming to America: Pre-Immigration Tax and Estate Planning Considerations”
May 17, 2023
Episode 3: Spring Cleaning Your Finances
May 10, 2023
Episode 2: IN FOCUS: "State Tax Audits Preparing for the Inevitable"
May 03, 2023
Episode 1: Multi-Family Real Estate vs. 401(k)
Apr 28, 2023