Insights topic

Financial Planning

Decisions, checklists, concentrated stock, and what money is actually for

Most money mistakes are not math mistakes. They are decisions made in a hurry, with the wrong question in front of you, at a moment when the stakes felt too big to slow down. This shelf is about the decisions themselves, the ones that shape a household's finances for decades, and how to think about them before you have to make them.

Here you will find guides on equity compensation and concentrated stock, checklists for the end of the year, plain warnings about fraud aimed at people over 60, and Anton's essays on what money is actually for. Everything is educational and general. When a decision is yours to make, the goal is that you walk into it knowing which questions matter.

Featured guide

Financial Planning

Equity Compensation Planning: A Guide to ISOs, RSUs, and Concentrated Stock

ISOs, RSUs, and concentrated stock each carry different tax rules and risks. This guide covers exercise timing, AMT planning, RSU vesting strategies, 10b5-1 plans, and diversification approaches with current 2026 figures.

  • Incentive stock options (ISOs), non-qualified stock options (NSOs), and restricted stock units (RSUs) are taxed differently, so equity compensation planning starts with knowing exactly which type of award you hold.
  • Exercising an ISO and holding the shares can trigger the Alternative Minimum Tax (AMT) on the bargain element. The 2026 AMT phaseout thresholds are lower and the phaseout rate is higher than in 2025, which can make a large exercise more costly to model.

Nyle Bayer · Published · 11 min read

Read the guide →

More in Financial Planning

Markets and Economy

Case for Staying Invested

For the past week, major media outlets have opined on the stock market volatility speculating whether this is the beginning of a significant stock market selloff and if the US economy is entering a deep recession cycle l

Anton Bayer · March 12, 2025 · 5 min read

Markets and Economy

Freedom is the Secret Sauce of America

We have mentioned in past UPdates the importance of monitoring the financial health and sentiment of US consumers. The primary reason is that American spending represents a whopping 67.9% of America’s Gross Domestic Prod

Anton Bayer · January 21, 2025 · 5 min read

Financial Planning

Client and Friend Events

Prior to the outbreak of the coronavirus in 2020, we used to host multiple client and friend dinner events each year. We would have these events typically at excellent local restaurants in the South Bay and East Sacramen

Anton Bayer · October 16, 2024 · 6 min read

Markets and Economy

When to Sell

Since the stock market bottomed on October 14, 2022, the major indices have rallied significantly. During these past 20 months, the tech-based NASDAQ index has soared 78.3% followed by a large-cap S&P 500 index up 55.53%

Anton Bayer · July 10, 2024 · 5 min read

Financial Planning

Christmas Memories

Yesterday was Christmas, and it seems like it was yesterday already. We are fortunate to have seven of our ten grandkids living close to us. As a result, we had a full house with all-day activities with kids and adults t

Anton Bayer · December 27, 2023 · 4 min read

Financial Planning

Holidays Are Here!

Now that Halloween is over, the winter holidays have officially started. Although Home Depot, Walmart, Target, Lowes, and every other box store thought the Christmas season started in August.

Anton Bayer · November 16, 2023 · 5 min read

Financial Planning

Values & Perceptions

The stock market is always moving as investors adjust their portfolios to their perspective of the economy and their stock holdings. The result is the actual value of stocks is rarely held as prices fluctuate above and b

Anton Bayer · November 1, 2023 · 5 min read

Financial Planning

Fraud Alert

It seems the scammers are out in greater force than ever. More alarming is their increasing success in scamming honest people out of their hard-earned money. As a result, I wanted to share with you many True Stories of s

Anton Bayer · October 4, 2023 · 10 min read

Markets and Economy

Investing for the Long Term

It appears investors are increasing their caution in buying stocks since the major indices peaked for the year high on July 31. Today's decline of the S&P 500 puts the index just 0.1% above its 200 Day Moving Average (DM

Anton Bayer · September 27, 2023 · 4 min read

Financial Planning

Overcoming Tragedy

One year ago, on September 9, 2022, I was in a horrific private plane crash. No, I wasn’t the pilot, nor did I own the plane. The plane was totaled, and amazingly, my friend, the pilot, and I both survived with slight in

Anton Bayer · September 13, 2023 · 7 min read

Financial Planning

Merry Christmas And Happy New Year!

Thinking about Christmas may be a bit early for you, but not for retailers. Executives of all businesses that depend on consumer spending are deep in preparation for this holiday season. These executives are evaluating t

Anton Bayer · August 2, 2023 · 6 min read

Markets and Economy

Timing is Everything, or Is It?

Since Jerome Powell, Federal Reserve Chairman, announced early 2022 the Federal Open Market Committee (FOMC) rate hike campaign to slow inflation, analysts have predicted a recession in 2023. Recessions do not suddenly s

Anton Bayer · May 10, 2023 · 4 min read

Financial Planning

Living

Throughout my life I have benefited from people with more experience and knowledge who have been generous to share what they have learned so my learning curve may be steeper with less setbacks due to mistakes.

Anton Bayer · April 27, 2023 · 7 min read

Markets and Economy

Lessons from the Silicon Valley Bank Collapse

It was an extraordinary experience for the years we lived in Cupertino, AKA Silicon Valley. During the late 1990s, neighbors were becoming millionaires and some billionaires overnight when their companies had an Initial

Anton Bayer · March 15, 2023 · 9 min read

← All Insights

Have a decision like this in front of you? See if you're a fit for a conversation with Up.

For general education only, not individualized tax or investment advice. Up Capital Management is a Registered Investment Adviser.