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How Do I Diversify a Highly Appreciated Stock Position Without Triggering a Massive Tax Bill

How Do I Diversify a Highly Appreciated Stock Position Without Triggering a Massive Tax Bill

by Steven Bernstein | Sep 25, 2026 | Blog

Owning a highly appreciated stock is a wonderful problem, right up until you decide to sell it. Maybe you bought the stock years ago, accumulated shares through your company, or simply made one very good investment. Now you’re sitting on a large gain and would love to...
What Should I Do With a $10 Million Concentrated Stock Position?

What Should I Do With a $10 Million Concentrated Stock Position?

by Steven Bernstein | Sep 25, 2026 | Blog

Having $10 million in one stock sounds like a fantastic problem to have. Maybe you spent decades working for the company, founded the business, inherited the shares, or simply made one spectacular investment and had the discipline, or good fortune not to sell it....
Why Doctors Need Disability Insurance, and Why Timing Matters

Why Doctors Need Disability Insurance, and Why Timing Matters

by Steven Bernstein | Aug 7, 2026 | Blog

Consider a physician in the early years of practice. After more than a decade of education and training, income is finally rising, student loans are declining and the pieces of a comfortable financial life are beginning to come together. There may be a new home, a...
From Fortune Tellers to Forecasts: What Prediction Markets Really Tell Investors

From Fortune Tellers to Forecasts: What Prediction Markets Really Tell Investors

by Steven Bernstein | Aug 7, 2026 | Blog

For years, baseball decisions were driven largely by experience, instinct and the practiced eye of the scout. Then Moneyball challenged the sport to look beyond conventional wisdom and ask whether the numbers were revealing something that experts had missed....
How Much Leverage Is the Right Amount for Your Portfolio

How Much Leverage Is the Right Amount for Your Portfolio

by Steven Bernstein | Aug 7, 2026 | Blog

The Savannah Bananas became a sensation by asking a question that traditional baseball had largely ignored: What do the fans actually want? They kept the heart of the game but removed much of what people disliked, including the slow pace, long pauses and feeling that...
The Real Cost of Eating Healthy: Why Your Green Juice May Be One of Your Best Investments

The Real Cost of Eating Healthy: Why Your Green Juice May Be One of Your Best Investments

by Steven Bernstein | Aug 7, 2026 | Blog

Because the most important asset in your portfolio isn’t your portfolio, it’s you. Let’s address the organic elephant in the room: healthy eating can be expensive. After all, when a salad costs more than a drive-thru combo meal and your weekly...
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Recent Posts

  • How Do I Diversify a Highly Appreciated Stock Position Without Triggering a Massive Tax Bill
  • What Should I Do With a $10 Million Concentrated Stock Position?
  • Why Doctors Need Disability Insurance, and Why Timing Matters
  • From Fortune Tellers to Forecasts: What Prediction Markets Really Tell Investors
  • How Much Leverage Is the Right Amount for Your Portfolio

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Steven Bernstein is a registered representative with, and securities and advisory services offered through LPL Financial, a registered investment advisor, Member FINRA & SIPC.

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