Read Doug’s articles originally printed in The Jerusalem Post.

Simplifying the Real Estate vs. Stock Market Debate
Simplifying the Real Estate vs. Stock Market Debate

Are you tempted to invest in real estate since the land prices seem to only go upward? If you decide to be a landlord, make sure you declare your rental income. The Israel Tax Authority is increasing its efforts to clamp down on tax evasion among landlords, using artificial intelligence to cross-reference records from the Land Registry to find unreported rental revenues.  … Read more

Tax Confusion: Simplifying Capital Gains for Cross-Border Investors
Tax Confusion: Simplifying Capital Gains for Cross-Border Investors

When it comes to investing, understanding capital gains is critical. Many are caught off-guard by the taxes due on their U.S. portfolios. However, this can be avoided with the right knowledge and strategy. Both realized and unrealized capital gains can affect your investment decisions and tax obligations. (While I do not give tax advice,… Read more

How to Avoid Surprises on Capital Gains in Your U.S. Investments
How to Avoid Surprises on Capital Gains in Your U.S. Investments

Navigating U.S. tax obligations from Israel can overwhelm many olim, especially when faced with unexpected tax bills. A common source of surprise is the difference between realized and unrealized gains. Realized gains occur when you sell an investment for a profit and are taxable in the year of the sale…. Read more

How to Best Handle Your U.S. Investments from Israel with Clear Communication
clear communitcaton

The convenience of digital communication introduces new challenges in the financial world. As a U.S. and Israeli licensed financial professional, I’m bound by regulations that mandate the archiving of client communications. Text messages, including those sent via platforms like WhatsApp, often fall outside these regulatory requirements. More importantly, there’s a deeper concern: the loss of clarity and understanding that can occur in text-based exchanges. … Read more

Do Volatile Markets Make You Feel as If You’re Being Punched in the Face?
Volatile Markets

There’s a famous quote by Mike Tyson that I find particularly relevant to investing: “Everyone has a plan until they get punched in the nose.” This is the essence of what I call the “Mike Tyson Logic of Investing.” You might have a solid investment plan, but how you react when the market takes a downturn is what truly matters…. Read more

Financial Resilience Post-Divorce: How to Create a New Investment Strategy
Financial Resilience Post-Divorce

Divorce is more than just the beginning of a new chapter; it’s the start of a new financial journey. Navigating this transition involves careful reallocation of joint assets and crafting investment, saving, and spending plans that align with your evolving goals.  
Post-divorce, your financial goals undergo a profound transformation as what once was a shared vision is now your own path,… Read more

Dealing with Illness: 3 Ways to Avoid Financial Ruin
Dealing with Illness: 3 Ways to Avoid Financial Ruin

When one spouse falls ill, it creates a new reality for your family. Here are three tips to help you prepare for an unexpected illness or injury in your family.  
Create a Contingency Plan  
You and your spouse should establish a plan that addresses your financial needs, healthcare needs,… Read more

Navigating Cross-Border Finance: Strategies for Family CFOs
navigating cross-border finances for family CFOs

Managing family finances goes beyond just dealing with local banks, paying bills, and filing taxes. When family members live in different countries, each with its own rules and financial systems, things get complicated. This complexity can cause the family’s CFO (the person in charge of the family’s money) stress when he needs to navigate different financial systems and tax codes…. Read more

Why U.S. Brokerage Firms Drop Clients Living Abroad
Protecting your overseas investments

Are you an overwhelmed CFO of your family, juggling the financial responsibilities of loved ones across borders? If so, you’re not alone. In my years as a financial planner, I’ve encountered many individuals exhausted by the complexities of managing investments for family members, especially when it involves cross-border regulations.  
The challenge often begins when family members move abroad (hooray for aliya!) only to discover their U.S…. Read more

Health Crisis: A Brief Financial Guide for Olim

What do your overseas investments have to do with medical care and family dynamics? 
Picture this: A couple in their seventies who have invested a substantial portion of their wealth in U.S. assets. They are comfortably retired in Israel and have Israeli grandchildren. Unfortunately, some of these grandchildren face health challenges that require financial assistance beyond what their kupat holim (HMO) provides.   … Read more