Jonathan On Money

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175

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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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September 30, 202629 min

Episode 180: IN FOCUS: Overlooked Estate Planning Questions That AI Does Not Address with Avi Kestenbaum (Meltzer Lippe)

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 Avi Z. Kestenbaum from Meltzer, Lippe, Goldstein & Breitstone, LLP based in Long Island, NY. Avi will be discussing “The Most Important and Overlooked Estate Planning Questions That AI Does Not Properly Address.” By way of background, this program will address • How to structure trust distribution standards •Choosing the right trustees and executors •Avoiding common planning mistakes •Determining appropriate fiduciary compensation •Evaluating when corporate, out‑of‑state, or foreign trusts make sense. •Optimal ages for beneficiary control •Selecting guardians and agents for powers of attorney and healthcare proxies •How to assess the value and cost of estate‑planning professionals. Listeners will gain practical, experience‑based guidance on the decisions that shape outcomes far more than documents alone. ***UPCOMING LIVE FALL WEBINAR: My next webinar is Thursday, October 8th @ 8:30am on “Planning for State Estate Taxes” featuring, Bruce D. Steiner from Kleinberg, Kaplan, Wolff & Cohen, P.C. based in New York City. I’ll include the registration link in the show notes to this episode. You can register here: https://us02web.zoom.us/webinar/register/WN_LRv_-3m1TR6Q4HV58rL-wQ *** 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.com 2) Signup for my monthly NEWSLETTER here: https://www.ParkBridgeWealth.com/newsletter 3) 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.

September 23, 202632 min

Episode 179: Writing Off Pesach Programs, Planning For Young Singles, & Roosevelt On Old Age

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: ***Upcoming Live FALL Webinar: Thursday, October 8th @ 8:30am featuring Bruce Steiner from Kleinberg, Kaplan, Wolff & Cohen, P.C. based in New York City and he will be speaking on “Planning for State Estate Taxes.” RSVP here: https://us02web.zoom.us/webinar/register/WN_LRv_-3m1TR6Q4HV58rL-wQ 1. Talking points: Smart Money Moves for the Young, Single, and Living at Home 2. This week’s quote is from Teddy Roosevelt on old age. 3. I was talking to some colleagues about personal finance, and one said it is tough to “get the goal posts to stop moving.” What does this mean, and what is your reaction? 4. I saw Yrefy advertised on Fox News. The returns look sick. Should I invest with them? 5. Do clients ever leave you? If so, why? 6. What is a dynamic withdrawal strategy in retirement? 7. Should I give my children their inheritance during my lifetime or leave it to them as a bequest at death? I am torn and not sure what to do. 8. Someone told me that if you speak on a Pesach program, you can write off the entire cost of the program as a business expense. Is that true? 9. If you could sum up one strategy that is a reliable way to get rich, what would it be? 10. I missed out on the latest run in a meme stock. How can I make sure I get in on the next meme stock before it takes off? 11. I cannot understand why so many advisors charge a percentage of assets under management. I think they should charge hourly like other professionals. Why don't they? 12. How should I weigh the recent economic numbers when investing new money in the market? 13. Timely Planning Idea: Your estate plan may be built for rules that no longer apply. ***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.com 2) 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.

September 16, 202630 min

Episode 178: IN FOCUS: NYC Pied-à-Terre Surcharge with K. Eli Akhavan (Grant, Herrmann)

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 K. Eli Akhavan from Grant, Herrmann, Schwartz & Klinger LLP based in New York City. Eli will be discussing “NYC Pied-à-Terre Surcharge – What Advisors Need to Know.” By way of background, New York City's pied-à-terre surcharge is now in the administration phase. The Department of Finance adopted its implementing rules in July, published a primary-residence addendum to the assessment roll on July 25, and is mailing notices to owners it treats as non-exempt by August 30 - after which the window to respond is short. Eli will discuss will who is actually a covered owner, how the primary residence exemption works when an apartment sits inside an LLC, a trust, or a stacked structure, why the January 5 taxable status date is unforgiving for buyers and renovations, and what to do when a notice lands. The focus is on what advisors and families need to do this fall, including the questions that the rules still leave open. ***UPCOMING LIVE FALL WEBINAR: My next webinar is Thursday, September 24th @ 8:30am on “The Most Important and Overlooked Estate Planning Questions That AI Does Not Properly Address” featuring, Avi Z. Kestenbaum, Esq., Partner, Meltzer, Lippe, Goldstein & Breitstone, LLP based in Long Island, New York. You can register here: https://us02web.zoom.us/webinar/register/WN_4i5n8PCtQX2-qfjWH-XZMw *** 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.com 2) Signup for my monthly NEWSLETTER here: https://www.ParkBridgeWealth.com/newsletter 3) 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.

September 9, 202628 min

Episode 177: Financial Lessons From Rosh Hashanah, My Big Win, and Using A Flux Capacitor

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: ***Upcoming Live FALL Webinar: Thursday, September 24th @ 8:30am featuring Avi Z. Kestenbaum of Meltzer, Lippe, Goldstein & Breitstone, LLP based in Long Island, New York and he will be speaking on “The Most Important and Overlooked Estate Planning Questions That AI Does Not Properly Address.” RSVP here: https://us02web.zoom.us/webinar/register/WN_4i5n8PCtQX2-qfjWH-XZMw 1. Talking points: 5 Powerful Financial Lessons Hiding Inside Rosh Hashanah 2. This week’s quote is from John Quincy Adams on property rights. 3. What’s your take on the “TACO trade”? 4. My CPA is a big advocate of backdoor Roth IRA contributions and insists that my wife and I make them every year. But I also have $300,000 in student loans. Which should be the bigger priority: making backdoor Roth contributions or paying down my student loans? 5. What are S&P 500 futures? I hear them mentioned on the news all the time, but I’m not sure what they are. 6. I just found out that I’m paying Wealthfront 65 basis points to access a CFP. Is that fee worth it? 7. How can we fix the housing market so my generation can afford to buy homes? 8. How can I get access to the latest IPOs? I need a big win to make up for years of not saving. 9. I have a taxable investment account that has performed very well over the past two years, but I need the money for a home addition. I’m hesitant to sell because the investments could continue to rise, and I don’t want to pay taxes. Should I wait longer to liquidate, and how do I get over the mental hurdle of selling investments to fund a major purchase? 10. Every professional investor has had a few “big wins.” Can you share a few of yours? 11. If someone gave you $1,000 with no strings attached, how would you spend it? What about $10,000, $100,000, or $1 million? 12. If you could buy anything to help you become a better investor, what would it be? 13. Timely Planning Idea: Medicare could quietly double your premium. ***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.com 2) 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.

September 2, 202626 min

Episode 176: Cosigning On A Loan For Child, Choosing ETFs, & Financial Peace of Mind in Retirement

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: ***Upcoming Live FALL Webinar: Thursday, September 10th @ 8:30am featuring K. Eli Akhavan from the law firm Grant, Herrmann, Schwartz & Klinger LLP based in New York City and he will be speaking on “NYC Pied-à-Terre Surcharge – What Advisors Need to Know. RSVP here: https://us02web.zoom.us/webinar/register/WN_lKrSMcckTXy9E8dzOqeGcA”*** 1. Talking points: How To Maintain Financial Peace of Mind in Retirement. 2. This week’s quote is from John Lock on how our income is like our shoes. 3. My son wants me to cosign his personal loan, but I’m 68 with a modest nest egg. Is it appropriate to decline, or should I help him? 4. With thousands of ETFs available, how can an investor identify a good one? 5. I planned to retire at the end of this year, but the recent market drop has significantly reduced my portfolio. How can I stay on track with my retirement plans despite the downturn? 6. What is a DTC transfer, and in what situations is it typically used? 7.My sister was advised to use $190,000 from her taxable investment account to pay down part of her 6% student loans, even though the S&P 500 averages about 11% annually. How does that recommendation make mathematical sense? ***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.com 2) 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 26, 202630 min

Podcast 175: Shalom Bayit & Money, Bad Advice From A Gvir, and Seinfeld On Torture We Can Deal With

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: ***Upcoming Live FALL Webinar: Thursday, September 10th @ 8:30am featuring K. Eli Akhavan from the law firm Grant, Herrmann, Schwartz & Klinger LLP based in New York City and he will be speaking on “NYC Pied-à-Terre Surcharge – What Advisors Need to Know. RSVP here: https://us02web.zoom.us/webinar/register/WN_lKrSMcckTXy9E8dzOqeGcA”*** 1. Talking points: Finances & Shalom Bayit: 10 Reasons Why Couples Fight About Money 2. This week’s quote is from Jerry Seinfeld on choosing the torture you can deal with. 3. How will the war with Iran affect my finances? 4. What are BDCs, and is my uncle’s strategy of keeping all his “safe money” in them sensible? 5. What is the difference between current yield and yield to maturity? 6. What exactly is credit risk? 7. Are technology stocks doomed because of the AI-driven tech crash? 8. Should I be worried about stagflation given rising oil prices and high unemployment? 9. What’s the difference between cash equivalents, notes, and bonds, and when should each be used? 10. Is Dave Ramsey actually credible? 11. Should I switch from an 80/20 portfolio to 100 percent stocks based on advice from a successful businessman at shul? 12. Is climate change driving inflation? Timely & Actionable Idea: Avoiding pulling money from the wrong accounts first. *** 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.com 2) 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 19, 202629 min

Episode 174: Elul & Your Portfolio, Financial Leaks, & Supporting Kids After Marriage

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: Elul and Your Portfolio: What the Month of Reflection Teaches Us About Money 2. This week’s quote is from Benjamin Franklin about financial leaks. 3. What is the term premium in the bond market? 4. What is a 351‑exchange ETF and how does it work? 5. At what level of wealth does a family office become appropriate? 6. My broker earns me about 11% annually, but the ongoing taxes are painful. Would triple tax‑free municipal bonds be a better option? 7. As teachers with modest incomes and six children, how can we save for weddings and support our kids after marriage without neglecting our own retirement? 8. Why do so many personal finance podcasters promote hourly‑fee financial advisors when almost no advisors actually charge that way? 9. What is a K‑shaped economy and how does it affect me? 10. I lost a lot of money in the latest Bitcoin drop. What should I do now? 11. Why do investment firms send 1099s in mid‑February instead of early January? 12. Timely & Actionable Idea: Avoiding big tax bills from mutual funds that LOST money. ***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.com 2) 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 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.com 2) 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.com 2) 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 Generation 2. 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.com 2) 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.