ThimbleberryU

In this episode of ThimbleberryU , we dive into part two of our series on debunking retirement myths with Amy Walls from Thimbleberry Financial. We explore five common misconceptions that can hinder financial planning for retirement, starting with the belief that Social Security alone can sustain retirees. Amy explains that Social Security is designed to cover only about 40% of pre-retirement inco...

In this episode of ThimbleberryU , we begin a two-part series debunking common myths about retirement. Jag and Amy Walls dive into the misconceptions that many people have when planning for their post-work years. The first myth we tackle is the belief that you need $1 million to retire comfortably. Amy explains that while this is often thrown around as a benchmark, the reality is far more nuanced....

Today, Amy and Jag delve into the contrasting strategies of lump sum investing versus dollar-cost averaging (DCA). Amy starts by defining lump sum investing as the practice of investing a large amount of money all at once, like a $100,000 bonus, while dollar-cost averaging involves spreading the investment over time, such as $10,000 a month for ten months. Amy explains that dollar-cost averaging h...

In this episode of ThimbleberryU, Jon "JAG" Gay and Amy Walls discuss strategies for making better decisions, particularly focusing on financial decision-making. We delve into what influences good and bad decisions and how we can improve our decision-making processes. We start by recognizing that emotions significantly impact our decisions. Amy shares a personal anecdote about her current dilemma...

In this episode of ThimbleberryU, Jon Gay and Amy Walls discuss the risks of having a highly concentrated portfolio. Amy defines a highly concentrated portfolio as one where a single asset or a small group of assets constitutes 10% or more of the portfolio’s total value. This lack of diversification can increase risk significantly, as the portfolio’s performance hinges on those few investments. Am...

In this episode of ThimbleberryU, we delve into the critical topic of safeguarding senior finances with Amy Walls from Thimbleberry Financial. The discussion highlights the importance of recognizing signs of financial exploitation among seniors and offers practical advice on how adult children can approach their parents about financial matters. We stress the importance of maintaining open, empathe...

In this episode of ThimbleberryU, Jon “JAG” Gay and Amy Walls tackle one of the biggest fears for retirees: running out of money before they die. They delve into the critical topic of deciding from which accounts to draw money in retirement, illustrating the profound impact these decisions can have on one's financial stability. Amy emphasizes that this concern often leads people to adopt an "ostri...

In this final episode of our six-part series for tech professionals, we focus on tying together the various aspects of equity compensation. We recap the key points discussed in previous episodes, including ESPPs, RSUs, ISOs, and NQSOs, emphasizing the importance of strategic management to leverage these tools effectively. We discuss the common pitfalls tech professionals encounter when managing eq...

Today Jag and Amy delve into five common myths surrounding retirement planning. Amy, leveraging her 20+ years of experience as a financial advisor, deconstructs each myth, providing insights grounded in real client interactions. First, they address the myth "I'll spend less in retirement," discussing how retirement often brings new expenses, such as travel, hobbies, and healthcare, which may not d...

Today, Amy Walls and Jag into the world of Non-Qualified Stock Options (NQSOs), a versatile form of equity compensation often offered to tech professionals. In our fifth episode of a six-part series, we explore how NQSOs, despite their simplicity in terms of taxation, require careful planning to effectively manage within one's financial portfolio. NQSOs allow employees to purchase company stock at...

We dive into a conversation about embracing future life phases today on ThimbleberryU. Amy and Jag discuss the importance of planning for both financial and non-financial aspects of our future. Amy emphasizes the significance of visualizing and imagining the life we want to lead, pointing out that financial planning isn't just about money—it's about making our desired future a reality. This involv...

In the 4th of our 6-part series for tech professionals,we dive into the world of Incentive Stock Options (ISOs), focusing on how tech professionals can leverage them. Amy Walls from Thimbleberry Financial breaks down ISOs as a form of equity compensation, allowing employees to buy company stock at a favorable price, known as the exercise price. The unique advantage of ISOs lies in their tax treatm...

Today, we dive into the complexities of choosing funds in employer-sponsored retirement plans like 401(k)s and 403(b)s. Amy Walls from Thimbleberry Financial breaks down common misconceptions and essential strategies for fund selection. She clarifies that not all funds are created equal, debunking myths about choosing solely based on cost or past performance. Amy emphasizes the importance of align...

We dive into the world of Restricted Stock Units (RSUs) in this episode, focusing on their role in equity compensation for tech professionals. RSUs are a form of stock option that grants ownership in a company's stock once vested, according to a predetermined schedule. This vesting schedule is crucial for employees to understand as it impacts their overall financial planning, including tax implica...

In our latest Thimbleberry U episode, we dive into inheriting investments.. Amy starts by differentiating between account types and actual investments. She focuses on the importance of the holdings in an account. Amy explains tax implications of inheriting investments, especially the step-up in basis, using an example to show how this works. When evaluating an inherited investment portfolio, Amy's...

In our latest episode of ThimbleberryU, Jag and I continue our six-part series focused on the tech sector. We delve into Employee Stock Purchase Plans (ESPPs), a topic particularly relevant to our tech professional listeners. An ESPP is a program allowing employees of public companies to buy company stock at a discounted price, typically through payroll deductions. We emphasize the importance of t...

In this episode of Thimbleberry U, Jag and Amy Walls from Thimbleberry Financial delve into the intricacies of Roth accounts for high-income earners. Amy begins by explaining the basics of Roth IRAs and their appeal to high-income individuals, particularly due to their tax-free growth and distributions. She emphasizes the importance of Roth accounts in the current low-tax environment and their rol...

In this episode of Thimbleberry U, Jag and Amy Walls from Thimbleberry Financial discuss the unique financial challenges faced by tech professionals, particularly focusing on equity compensation. The episode is the first in a six-part series dedicated to addressing the financial needs of tech professionals. Amy highlights three major challenges tech professionals face regarding equity compensation...

Jag and Amy discuss the importance of celebrating financial milestones and the psychological benefits of doing so. Amy emphasizes that acknowledging financial achievements, such as reaching a significant net worth, completing estate planning, paying off a mortgage, or achieving retirement goals, is crucial for several reasons. First, celebrating these milestones motivates individuals and gives the...

In this final episode of ThimbleberryU's six-part series,  Jag and Amy delve into the critical topic of legacy and estate planning for healthcare professionals. Amy points out the potential disputes and uncertainties that can arise without proper planning, as seen in the cases of Prince and Aretha Franklin. Legacy planning ensures that assets are distributed according to one's wishes and helps in...

Welcome to episode 100 of ThimbleberryU, where we're diving into the integration of financial planning and wealth management at Thimbleberry Financial. Amy and Jag are also reflecting on the journey of the podcast over the past four years. Amy emphasizes the importance of combining financial planning and wealth management. Financial planning is not solely about investment management. She highlight...

Today, we're delving into a crucial topic as part five of our series on healthcare professionals – protecting your assets and your family. Amy explains that protection isn't just about insurance, although that's a significant part of it. It encompasses various forms of insurance like life insurance, disability insurance, long-term care insurance, and more. For healthcare professionals, malpractice...

For many of Thimbleberry Financial's clients in the  startup and tech communities, Incentive Stock Options, or ISO's, are a hot topic.  Today, Amy Walls and Jag break them down. Simply put, an ISO is a type of employee stock option that comes with tax advantages.  No income tax is due when options are granted or exercised. Also, profits from the sale of ISO's can be taxed under more favorable long...

In the fourth of our six-part series specifically for Healthcare Professionals, Amy Walls of Thimbleberry Financial gets into the tax complexities facing those in this field.  These factors can include higher income, sometimes from multiple sources (and across borders), capital gains, and even taxes on tuition benefits for those at teaching hospitals. Amy walks us through the hurdles of having sep...

In this episode of ThimbleberryU, Amy Walls and Jag delve into the intricacies of preparing for a six-month break between jobs. Amy's insights shed light on assessing financial situations, emphasizing the importance of building a solid foundation based on savings, investments, debts, and monthly expenses. We cover the financial considerations of taking a six-month break. Amy's practical approach n...