Jonathan On Money

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172

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Aug 2026

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About the show

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 Hosted on Acast. See acast.com/privacy for more information.

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August 12, 202627 min

Episode 173: Leaving A Lasting Legacy, Big Houses, Skipping College, & Unmotivated Children

Join Jonathan I. Shenkman, President and Chief Investment Officer of ParkBridge Wealth Management, this week as he discusses a variety of timely investing and financial planning topics, including: 1. Talking points: What Jewish Tradition Teaches About Leaving a Lasting Legacy 2. This week’s quote is from Harvey Firestone on big houses. 3. I planned to spend a few years learning in Israel and then a year in kollel, with financial support from my father and father in law. They both backed out. What should I do now. 4. A money manager from my shul is soliciting me, claiming his returns far exceed those of my current advisor and pressuring me to switch. How should I evaluate this. 5. A prospective advisor suggested keeping my home purchase funds invested and borrowing against the portfolio instead. Is that a smart strategy. 6. My son skipped college, spent time in Israel, and now sells appliances. He earned six figures last year and bought a car with cash. He could get into college but has no interest. Should we push him toward a degree or support his current path. 7. I am financially successful. What key financial planning and investment considerations should someone with significant wealth prioritize. 8. My colleagues mentioned NUA in relation to company stock in a 401(k). What is NUA and when does it make sense. 9. My adult son is unmotivated, disengaged, and has no career direction. I want him off my payroll and am considering suggesting a job at the DMV. What other roles fit someone with his temperament. 10. I am a newer financial advisor, and many friends with salaried jobs are condescending when I market my business. They do not understand what it takes to build a practice, and it is discouraging. How do I handle this dynamic. 11. I am looking for an affordable home in a New York area suburb that feels friendly, inclusive, and somewhat out of town. How can I identify communities like that. 12. Timely & Actionable Idea: tax traps to avoid, in particular missing out on your cheapest tax years to do Roth IRA conversions. ***Upcoming Live FALL Webinar: Get notified of upcoming LIVE webinars by signing up for my webinar distribution list here: https://www.parkbridgewealth.com/webinars***  ***My FIRST book: D is for Diversification: The ABCs of Personal Finance available on Amazon or at www.JonathanOnMoney.com***  Stay connected:1) Questions? Comments? Reach out to Jonathan@ParkBridgeWealth.com2) Signup for my monthly NEWSLETTER here: https://www.ParkBridgeWealth.com/newsletter 3) Get notified of upcoming LIVE webinars: https://www.parkbridgewealth.com/webinars  4) WATCH my daily financial planning videos @JonathanOnMoney: Instagram | X | YouTube | LinkedIn Hosted on Acast. See acast.com/privacy for more information.

August 5, 202637 min

Episode 172: ROI On Plastic Surgery, AI, Richard Nixon, OnlyFans, & More

Join Jonathan I. Shenkman, President and Chief Investment Officer of ParkBridge Wealth Management, this week as he discusses a variety of timely investing and financial planning topics, including:  1. Talking points: Can AI Really Answer All Your Financial Questions?2. This week’s quote is from Richard Nixon on purpose.3. I earn significant income on OnlyFans. How should I manage my finances as an independent contractor?4. My Yeshiva offers a retirement plan, but there’s no guidance on choosing investments and the provider mainly pushes its own funds. Is this normal, and how should I evaluate fees and conflicts of interest?5. Does plastic surgery provide a good return on investment?6. I’ve been saving monthly into a NY 529 plan and planned to use that money for future weddings and college expenses. Is this a sound strategy?7. A blogger I follow says most people should fire their financial advisor and manage their own money. Is that good advice?8. Is investing in Airbnb properties a smart move? My colleague owns several and seems to be doing well.9. How do 529 and UTMA accounts affect college financial aid eligibility, and how much should that factor into planning?10. As a surgeon, how can I best protect my assets from potential lawsuits?11. I’m selling my business in 2026 and worried about taxes. My broker suggested borrowing against my investment portfolio to cover the tax bill. Is that a good idea?12. Timely & Actionable Idea: tax traps to avoid, in particular why your asset location may be backward. ***Upcoming Live FALL Webinar: Get notified of upcoming LIVE webinars by signing up for my webinar distribution list here: https://www.parkbridgewealth.com/webinars***  ***My FIRST book: D is for Diversification: The ABCs of Personal Finance available on Amazon or at www.JonathanOnMoney.com***  Stay connected:1) Questions? Comments? Reach out to Jonathan@ParkBridgeWealth.com2) Signup for my monthly NEWSLETTER here: https://www.ParkBridgeWealth.com/newsletter 3) Get notified of upcoming LIVE webinars: https://www.parkbridgewealth.com/webinars  4) WATCH my daily financial planning videos @JonathanOnMoney: Instagram | X | YouTube | LinkedIn Hosted on Acast. See acast.com/privacy for more information.

July 29, 202626 min

Episode 171: Financial Survival for the Sandwich Generation, Responsibilities Of Trustees, & Portfolio Perfection

Join Jonathan I. Shenkman, President and Chief Investment Officer of ParkBridge Wealth Management, this week as he discusses a variety of timely investing and financial planning topics, including: 1.            Talking points: When Everyone Depends on You: Financial Survival for the Sandwich Generation2.            This week’s quote is from Morgan Housel on the downside of having money.3.            What’s a SERP plan?4.            Do you avoid taxes by being in international waters on April 15?5.            What are the responsibilities of a trustee?6.            What should my son do with his bar mitzvah money?7.            What should the perfect portfolio look like?8.            Who is right about my 401(k) allocation: my CPA or my financial advisor?9.            Should I sell the stocks my grandfather gave me to buy a home in Israel?10.        If I buy a municipal bond at a discount, is the entire yield to maturity tax free?11.        Timely & Actionable Idea: Mid-Year Financial Resolutions ***Upcoming Live FALL Webinar: Get notified of upcoming LIVE webinars by signing up for my webinar distribution list here: https://www.parkbridgewealth.com/webinars***  ***My FIRST book: D is for Diversification: The ABCs of Personal Finance available on Amazon or at www.JonathanOnMoney.com***  Stay connected:1) Questions? Comments? Reach out to Jonathan@ParkBridgeWealth.com2) Signup for my monthly NEWSLETTER here: https://www.ParkBridgeWealth.com/newsletter 3) Get notified of upcoming LIVE webinars: https://www.parkbridgewealth.com/webinars  4) WATCH my daily financial planning videos @JonathanOnMoney: Instagram | X | YouTube | LinkedIn Hosted on Acast. See acast.com/privacy for more information.

July 22, 202628 min

Episode 170: Trump Accounts, Prenups, & Economic Challenges Facing Our Youth

Join Jonathan I. Shenkman, President and Chief Investment Officer of ParkBridge Wealth Management, this week as he discusses a variety of timely investing and financial planning topics, including:         1.   Talking points: Are Prenuptial Agreements Necessary When a Couple Has Disparate Levels of Wealth?2.   This week’s quote is from Jason Zweig on chasing performance.3.   Can a trustee be removed for poor investment returns in a trust where I am the beneficiary?4.   Is an UTMA account truly tax advantaged, or is that a misconception?5.   I am heavily concentrated in tech stocks at age 67 and nearing retirement. When should I diversify, into what, and how should I think about taxes?6.   Are young people today facing uniquely difficult economic conditions, and what advice would you give them for getting ahead?7.   My siblings and I inherited a multifamily property in Brooklyn, but I do not want to co‑own real estate with them. They want to keep the property. How should I handle this situation?8.   Timely & Actionable Idea: All you need to know about Trump Accounts ***Upcoming Live FALL Webinar: Get notified of upcoming LIVE webinars by signing up for my webinar distribution list here: https://www.parkbridgewealth.com/webinars***  ***My FIRST book: D is for Diversification: The ABCs of Personal Finance available on Amazon or at www.JonathanOnMoney.com***  Stay connected:1) Questions? Comments? Reach out to Jonathan@ParkBridgeWealth.com2) Signup for my monthly NEWSLETTER here: https://www.ParkBridgeWealth.com/newsletter 3) Get notified of upcoming LIVE webinars: https://www.parkbridgewealth.com/webinars  4) WATCH my daily financial planning videos @JonathanOnMoney: Instagram | X | YouTube | LinkedIn Hosted on Acast. See acast.com/privacy for more information.

July 15, 202632 min

Episode 169: Nine Days-Nine Lessons, Single Stock ETFs, & Multiple Retirement Plan Rules

Join Jonathan I. Shenkman, President and Chief Investment Officer of ParkBridge Wealth Management, this week as he discusses a variety of timely investing and financial planning topics, including:        1.   Talking points: Nine Days, Nine Lessons: What Our Period of Mourning Teaches Us About Money2.   This week’s quote is from Abigail Disney on flying private 3.   I rolled over my old 401(k) to my advisor years ago and now cannot do backdoor Roth contributions because of the pro rata rule. What is this rule, and should I be upset that this limits my options?4.   Thoughts on single‑stock ETFs?5.   I am 63, financially independent, and still working because I find it moderately rewarding. I do not need more money, but I am unsure what I would do if I retired. When is the right time to stop working?6.   My money is at Schwab in very low‑cost funds, but Fidelity offers some zero‑fee funds. Should I sell my Schwab funds and move to Fidelity to avoid ongoing expenses?7.   The wealthiest people in history often became rich by concentrating in one stock rather than diversifying. Rockefeller, Carnegie, and Gates all did this. Are finance textbooks wrong, and are index funds simply a path to average returns?8.   My parents in Los Angeles need a new advisor. Would you travel there to meet them?9.   Are all‑inclusive resorts worth it?10. I transferred my account to a new investment firm and believe I missed an $80 dividend during the transition. My account is $500,000, but I still want that dividend reimbursed. How do I resolve this?11. Timely & Actionable Idea: Avoid big investment decisions during the Nine Days. ***Upcoming Live FALL Webinar: Get notified of upcoming LIVE webinars by signing up for my webinar distribution list here: https://www.parkbridgewealth.com/webinars***  ***My FIRST book: D is for Diversification: The ABCs of Personal Finance available on Amazon or at www.JonathanOnMoney.com***  Stay connected:1) Questions? Comments? Reach out to Jonathan@ParkBridgeWealth.com2) Signup for my monthly NEWSLETTER here: https://www.ParkBridgeWealth.com/newsletter 3) Get notified of upcoming LIVE webinars: https://www.parkbridgewealth.com/webinars  4) WATCH my daily financial planning videos @JonathanOnMoney: Instagram | X | YouTube | LinkedIn Hosted on Acast. See acast.com/privacy for more information.

July 8, 202629 min

Episode 168: America At 250, Jewish Financiers Who Helped Build a Nation, and Investing in Apple Pie & BBQs

Join Jonathan I. Shenkman, President and Chief Investment Officer of ParkBridge Wealth Management, this week as he discusses a variety of timely investing and financial planning topics, including:        1.   Talking points: America at 250: The Jewish Financiers Who Helped Build a Nation2.   This week’s quote is from JP Morgan on betting against America.3.   How much to spend on a first date?4.   Will AI replace financial advisors?5.   How do I calculate my dad's RMD? He is not on top of this stuff anymore, so I need to figure it out since he doesn’t work with a financial advisor. His IRA money is at a few different firms. 6.   I like the idea of investing in real estate because it’s an investment I can see and touch. Feels more secure to me. What are some of the risks of being a landlord that I may be overlooking?7.   My daughter entered the financial advisory training program at a large firm. She spends a lot of time handling menial tasks. Is this standard practice? If so, when does the work get more interesting?8.   Timely & Actionable Idea: Investing in Apple Pie & BBQs ***Upcoming Live FALL Webinar: Get notified of upcoming LIVE webinars by signing up for my webinar distribution list here: https://www.parkbridgewealth.com/webinars***  ***My FIRST book: D is for Diversification: The ABCs of Personal Finance available on Amazon or at www.JonathanOnMoney.com***  Stay connected:1) Questions? Comments? Reach out to Jonathan@ParkBridgeWealth.com2) Signup for my monthly NEWSLETTER here: https://www.ParkBridgeWealth.com/newsletter 3) Get notified of upcoming LIVE webinars: https://www.parkbridgewealth.com/webinars  4) WATCH my daily financial planning videos @JonathanOnMoney: Instagram | X | YouTube | LinkedIn Hosted on Acast. See acast.com/privacy for more information.

July 1, 202635 min

Episode 167: IN FOCUS: Mid-Year Money Check-In - The 2026 Trends That Are Impacting Your Wealth

Join Jonathan I. Shenkman, President & CIO of ParkBridge Wealth Management, as he goes “IN FOCUS” to explore more advanced wealth planning topics.       This week, we go IN FOCUS where we explore more advanced wealth planning topics.    Today, Jonathan Shenkman from ParkBridge Wealth Management will be discussing “Mid-Year Money Check-In: The 2026 Trends That Are Impacting Your Wealth.”By way of background, this episode will be a fast-paced mid-year briefing highlighting the key forces shaping portfolios and financial plans in 2026. We’ll cover how AI is influencing investor behavior and the wealth-management landscape, the market impact of the Iran war, the shift away from U.S. market concentration and what it means for diversification. We’ll also review important 2026 tax and estate-planning changes affecting high-net-worth families, along with updates on interest rates, inflation, and election-year dynamics, and more. The goal is for listeners to have a clear understanding of the year’s most important developments and how to position portfolios strategically for the future.***UPCOMING LIVE FALL WEBINAR: My FALL webinars will be sent out in the coming weeks. You can register to get notified of upcoming events here: www.ParkBridgeWealth.com/Webinars*** M latest book, “D is for Diversification: The ABCs of Personal Finance” is now available on Amazon or at www.JonathanOnMoney.com. It is a great way to support these podcasts.  Stay connected:1) Questions? Comments? Media Inquiries? Reach out to Jonathan@ParkBridgeWealth.com2) Signup for my monthly NEWSLETTER here: https://www.ParkBridgeWealth.com/newsletter3) Get notified of upcoming LIVE webinars: https://www.parkbridgewealth.com/webinars 4) Click to follow/connect: Instagram | X | YouTube | LinkedIn | Blog Hosted on Acast. See acast.com/privacy for more information.

June 24, 202619 min

Episode 166: Ultimate Advice For Recent Grads, Investing In Films, & Giving up a 2.75% Mortgage

Join Jonathan I. Shenkman, President and Chief Investment Officer of ParkBridge Wealth Management, this week as he discusses a variety of timely investing and financial planning topics, including:        1.   Talking points: My talking points this week will discuss The Ultimate Advice for Recent Graduates2.   This week’s quote is from Winston Churchill on giving.3.   What are your thoughts on a 50 year mortgage?4.   How to minimize tax burden from large IRAs?5.   What type of trade order should I put in when buying ETFs?6.   I have the opportunity to invest in a film. Should I do this? Is this legit? Can I make money doing this?7.   I want to move to another community, but don’t want to give up my 2.75% mortgage. What do I do?8.   Timely & Actionable Idea: Figure out your safe withdrawal rate ***Upcoming Live FALL Webinar: Get notified of upcoming LIVE webinars by signing up for my webinar distribution list here: https://www.parkbridgewealth.com/webinars***  ***My FIRST book: D is for Diversification: The ABCs of Personal Finance available on Amazon or at www.JonathanOnMoney.com***  Stay connected:1) Questions? Comments? Reach out to Jonathan@ParkBridgeWealth.com2) Signup for my monthly NEWSLETTER here: https://www.ParkBridgeWealth.com/newsletter 3) Get notified of upcoming LIVE webinars: https://www.parkbridgewealth.com/webinars  4) WATCH my daily financial planning videos @JonathanOnMoney: Instagram | X | YouTube | LinkedIn Hosted on Acast. See acast.com/privacy for more information.

June 17, 202628 min

Episode 165: IN FOCUS: How to Discharge IRS and NYS Tax Liens with Scott Kestenbaum and Jill Monoson (Kestenbaum & Mark)

Join Jonathan I. Shenkman, President & CIO of ParkBridge Wealth Management, as he goes “IN FOCUS” to explore more advanced wealth planning topics.       This week, we go IN FOCUS where we explore more advanced wealth planning topics.Today, we are joined by Scott Kestenbaum and Jill Monoson both from Kestenbaum & Mark LLP based in Great Neck, NY. Scott and Jill will be discussing “Don’t Lien on Me: How to Discharge IRS and NYS Tax Liens.” By way of background, this episode will cover the discharge of income tax liens by the IRS and New York State (NYS), exploring the conditions under which these liens can be removed or resolved. It will delve into the specific procedures for requesting a discharge, the required forms, and key factors that influence approval. Additionally, the talk will address the release of estate tax liens by both the IRS and NYS, highlighting the unique circumstances and processes involved in discharging liens related to estate taxes. Practical insights will be provided on how individuals and businesses can navigate these complex tax lien issues.***UPCOMING LIVE SPRING WEBINAR: My next webinar is Thursday, June 18th @ 8:30am on “Mid-Year Money Check-In: The 2026 Trends That Are Impacting Your Wealth” featuring, yours truly, Jonathan I. Shenkman President & Chief Investment Officer of ParkBridge Wealth Management based in New York. You can register here: https://us02web.zoom.us/webinar/register/WN_aF6uLMEfRUGjJeCQad2c8g*** M latest book, “D is for Diversification: The ABCs of Personal Finance” is now available on Amazon or at www.JonathanOnMoney.com. It is a great way to support these podcasts.  Stay connected:1) Questions? Comments? Media Inquiries? Reach out to Jonathan@ParkBridgeWealth.com2) Signup for my monthly NEWSLETTER here: https://www.ParkBridgeWealth.com/newsletter3) Get notified of upcoming LIVE webinars: https://www.parkbridgewealth.com/webinars 4) Click to follow/connect: Instagram | X | YouTube | LinkedIn | Blog Hosted on Acast. See acast.com/privacy for more information.

June 10, 202625 min

Episode 164: Managing Bar Mitzvah Money, Are Backdoor Roth IRAs Immoral, Professionals That Are The Worst At Managing Money

Join Jonathan I. Shenkman, President and Chief Investment Officer of ParkBridge Wealth Management, this week as he discusses a variety of timely investing and financial planning topics, including:       1.   Talking points: What Should My Son Do with His Bar Mitzvah Money?2.   This week’s quote is from F. Scott Fitzgerald on how it is never too late.3.   Any financial strategies you would recommend with the commie Mayor of New York who never held a real job in his life?4.   Is a backdoor Roth IRA immoral because you have too much money to contribute to a Roth IRA due to the regular income phaseouts?5.   Which professionals are the worst at managing their money?6.   Can ChatGPT solve most of my financial questions? Be honest. It seems like it can solve most questions.7.   I want to rebalance my taxable account, but given the large gains it will cause a meaningful taxable event. On the other hand, if I don’t rebalance, my portfolio will become much more heavily weighted in stocks which will make it riskier. What do you suggest I do?8.   Timely & Actionable Idea: Setup a sensible investment program leading up to retirement. ***Upcoming Live SPRING Webinar: On THURSDAY, JUNE 18th @ 8:30am featuring Jonathan I. Shenkman, AIF®, President & CIO, ParkBridge Wealth Management based in New York. Jonathan will be discussing Mid-Year Money Check-In: The 2026 Trends That Are Impacting Your Wealth.” SIGN UP HERE: https://us02web.zoom.us/webinar/register/WN_aF6uLMEfRUGjJeCQad2c8g***  ***My FIRST book: D is for Diversification: The ABCs of Personal Finance available on Amazon or at www.JonathanOnMoney.com***  Stay connected:1) Questions? Comments? Reach out to Jonathan@ParkBridgeWealth.com2) Signup for my monthly NEWSLETTER here: https://www.ParkBridgeWealth.com/newsletter 3) Get notified of upcoming LIVE webinars: https://www.parkbridgewealth.com/webinars  4) WATCH my daily financial planning videos @JonathanOnMoney: Instagram | X | YouTube | LinkedIn Hosted on Acast. See acast.com/privacy for more information.

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Jonathan On Money

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Listen to episodes

Episode 173: Leaving A Lasting Legacy, Big Houses, Skipping College, & Unmotivated Children

Episode 172: ROI On Plastic Surgery, AI, Richard Nixon, OnlyFans, & More

Episode 171: Financial Survival for the Sandwich Generation, Responsibilities Of Trustees, & Portfolio Perfection

Episode 170: Trump Accounts, Prenups, & Economic Challenges Facing Our Youth

Episode 169: Nine Days-Nine Lessons, Single Stock ETFs, & Multiple Retirement Plan Rules

Episode 168: America At 250, Jewish Financiers Who Helped Build a Nation, and Investing in Apple Pie & BBQs

Episode 167: IN FOCUS: Mid-Year Money Check-In - The 2026 Trends That Are Impacting Your Wealth

Episode 166: Ultimate Advice For Recent Grads, Investing In Films, & Giving up a 2.75% Mortgage

Episode 165: IN FOCUS: How to Discharge IRS and NYS Tax Liens with Scott Kestenbaum and Jill Monoson (Kestenbaum & Mark)

Episode 164: Managing Bar Mitzvah Money, Are Backdoor Roth IRAs Immoral, Professionals That Are The Worst At Managing Money

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