Episode 86: Should I Sell My Rental Home and Invest The Proceeds In The Market?

Episode 86: Should I Sell My Rental Home and Invest The Proceeds In The Market?

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: The Oldest And Most Effective Financial Planning Strategy

2. This week’s quote is from Jim Carrey.

3. Should I buy a home or invest in my 401k?

4. I’ve had two relatives ask to borrow money (one for a medical bill and another to help with a down payment). I have the money but want to be sure they view it as a real loan, not a gift. What’s your advice on how to handle this?

5. I am moving my father into an independent living community and I’ve made a budget based on his current assets. Most of his retirement money is in mutual funds. I want to liquidate his investments and move them to somewhere stable that will still gain some interest and results in the least amount of taxes. What do you recommend?

6. I’m searching for someone to manage my money. My local bank seems to be the most seamless because my checking account is there. Your thoughts on working with a local branch instead of a wealth management firm.

7. How effective is back testing to determine if a portfolio makes sense?

8. I filled out a risk tolerance questionnaire with my advisor and it came out that I was aggressive. But my performance has not been that high even though I took a lot of risk. What do you think my advisor is doing wrong?

9. I’m renting out a single family home in another state. I’m debating selling the home and investing it in the market, but how do I calculate where I would get a better return?

10. I put most of my net worth in one investment. I was advised not to. Of course it went down by 70%. My advisor told me I should sell it and move on. What do you recommend?

11. I handle our personal finances and my spouse has no clue about anything related to this matter. Is that acceptable?

12. Timely & Actionable Idea

***UPCOMING LIVE WEBINAR: Thursday, December 12th at 8:30am (New York time) featuring, Boaz Feinberg from the law firm Arnon Tadmor Levy based in Tel Aviv and he will be speaking on the topic of “International Taxation Law in Israel: Are Your Client’s Prepared for the New and Evolving Rules?” Register: https://us02web.zoom.us/webinar/register/WN_BeN3LlrDSjiOXfhbBVnvcw

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: Instagram | X | YouTube | LinkedIn

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Avsnitt(158)

Episode 158: Affording The Five Towns, Inherited Real Estate, Dress To Impress, & High Returns Using ETFs

Episode 158: Affording The Five Towns, Inherited Real Estate, Dress To Impress, & High Returns Using ETFs

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: ...

29 Apr 19min

Episode 157: IN FOCUS: When the Family Is the Business - Why You Need a Real Partnership Agreement with Av Sinensky (Falcon Rappaport & Berkman)

Episode 157: IN FOCUS: When the Family Is the Business - Why You Need a Real Partnership Agreement with Av Sinensky (Falcon Rappaport & Berkman)

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 mor...

22 Apr 57min

Episode 156: Pesach Programs, Reinvesting Dividends, and Are Teachers Underpaid

Episode 156: Pesach Programs, Reinvesting Dividends, and Are Teachers Underpaid

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: ...

15 Apr 24min

Episode 155: IN FOCUS: Retirement 2.0 - Modern Planning Strategies for 2026

Episode 155: IN FOCUS: Retirement 2.0 - Modern Planning Strategies for 2026

Join Jonathan I. Shenkman, President & CIO of ParkBridge Wealth Management, as he goes “IN FOCUS” to explore more advanced wealth planning topics. Today, Jonathan will discuss Today, I discuss “Re...

7 Apr 32min

Episode 154: The Seder & Investing, Retiring Into a Down Stock Market, Working With A $400 million Client

Episode 154: The Seder & Investing, Retiring Into a Down Stock Market, Working With A $400 million Client

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: ...

31 Mars 24min

Episode 153: IN FOCUS: Highlights of the 2026 Heckerling Institute on Estate Planning with Kevin Matz (ArentFox Schiff)

Episode 153: IN FOCUS: Highlights of the 2026 Heckerling Institute on Estate Planning with Kevin Matz (ArentFox Schiff)

***My FIRST Book: D is for Diversification: The ABCs of Personal Finance available on Amazon or at www.JonathanOnMoney.com***Join Jonathan I. Shenkman, President & CIO of ParkBridge Wealth Management,...

25 Mars 59min

Episode 152: Annuity vs Lump Sum Payment, Does Your Yeshiva Have A Good 401(k) & My Best Purchase For Under $100

Episode 152: Annuity vs Lump Sum Payment, Does Your Yeshiva Have A Good 401(k) & My Best Purchase For Under $100

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: ...

18 Mars 28min

Episode 151: IN FOCUS: How to Shift CRT Benefits to Children Under Today’s Tax Rules with Evan Unzelman (CRT Experts)

Episode 151: IN FOCUS: How to Shift CRT Benefits to Children Under Today’s Tax Rules with Evan Unzelman (CRT Experts)

***My FIRST Book: D is for Diversification: The ABCs of Personal Finance available on Amazon or at www.JonathanOnMoney.com*** Join Jonathan I. Shenkman, President & CIO of ParkBridge Wealth Managemen...

11 Mars 27min

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