ThimbleberryU

In this episode, we confront a truth many couples avoid: one partner will likely outlive the other. Statistically, especially in heterosexual relationships, it’s often the woman. That fact shapes the financial, emotional, and logistical choices couples need to make as they plan for retirement. We talk about why it’s essential to create a shared plan—one that not only protects assets, but gives pea...

In this episode of ThimbleberryU , we step behind the curtain of financial planning to unpack what makes a financial plan succeed—and just as importantly—what can derail it. We kick things off with a discussion about structure and intentionality. Amy Walls explains how her team at Thimbleberry Financial organizes their schedules to be proactive and client-focused. By setting clear availability and...

In this episode, we tackle a difficult but crucial topic: what to do when someone passes away. While it’s not a conversation most people want to have, planning ahead can save significant stress and confusion for those left behind. We start with the immediate steps that need to be taken. First, a legal pronouncement of death is required, which is usually handled by hospital or hospice staff, but in...

In this episode, we dive into the 83(b) Election—a tax strategy that can have significant financial implications for individuals who receive stock as part of their compensation. While it might sound technical, understanding how it works can be crucial for employees, particularly in startups and the tech sector. The 83(b) Election allows recipients of stock grants to pay taxes on the stock's value...

In this episode, we dive into one of the most delicate yet essential discussions families need to have: aging and finances. It’s not just about planning for the future—it’s about ensuring clarity and peace of mind for everyone involved. Many parents assume their children are only interested in their inheritance, while adult children are more focused on logistics—whether their parents are financial...

In this episode of ThimbleberryU , Jag and Amy delve into the benefits and functionality of virtual financial advising, a model that Thimbleberry Financial has embraced fully. Amy explains how their transition to a 100% virtual advisory model was initially born out of necessity during the COVID-19 pandemic but has since proven to be a more efficient and effective way to serve clients. Catering to...

In this episode of ThimbleberryU , we dive into a detailed case study centered on Stan and Jan, a fictitious couple navigating the complexities of retirement planning with a focus on creating income, simplifying finances, and leaving a meaningful legacy. With $5 million in assets—$3 million in qualified accounts like IRAs - and 403(b)s and $2 million in taxable accounts—they are financially secure...

In this episode of ThimbleberryU , we dive into the financial uncertainty researchers are facing due to upcoming NIH funding changes. Many professionals in research and healthcare are dealing with shifting grant structures, including caps on overhead costs for already-funded projects. These changes create job security concerns and financial stress, so we focus on practical steps individuals can ta...

Today, JAG interviews Amy Walls about her journey into financial advising and her work with tech and healthcare professionals. With over five years and 128 episodes together, Jag and Amy take the opportunity to reflect on Amy's "why"—the motivation behind her career at Thimbleberry Financial. Amy shares that her early exposure to financial advising came from her father, who was a financial advisor...

In this episode of ThimbleberryU , we dive into a critical financial planning misconception: using a HELOC (home equity line of credit) as a cash reserve. This approach can increase financial risk and reduce flexibility, and we offer smarter alternatives for financial security. Amy begins by explaining what a HELOC is—a line of credit secured by the equity in your home that operates much like a cr...

In this episode of ThimbleberryU , we dive into actionable strategies to make 2025 a banner year for financial growth. We focus on practical, often-overlooked habits that can help listeners tackle common hurdles in financial planning, like maximizing contributions, handling stock options, estate planning, and finding a healthier work-life balance. Amy Walls begins by discussing the challenges of m...

In this episode of ThimbleberryU , we continue our conversation about teaching kids financial responsibility, focusing on debt, budgeting, generosity, and investing. Jag and Amy Walls provide practical strategies for helping children understand money in an age-appropriate way. We start by tackling the sensitive topic of debt. Amy shows us her “suitcase” analogy to explain tailoring financial discu...

In this episode of ThimbleberryU , we dive into a crucial topic: teaching kids financial responsibility. Jon Gay and Amy Walls discuss practical strategies and personal experiences around introducing children to money management. One of the key points is the importance of teaching responsibility first. Amy emphasizes that kids should learn that some tasks are simply part of being in a family and s...

In this episode of ThimbleberryU , we tackle the complex and often surprising situation of receiving an early retirement offer from your employer.  Amy walks us through the essential considerations when navigating such an offer, emphasizing that while the initial reaction may be shock or panic, taking a step back to calmly assess the situation is crucial. The first point Amy makes is that understa...

In this episode of ThimbleberryU , we explore the concept of building intergenerational wealth. Amy Walls and Jon "Jag" Gay dive into the importance of ensuring your own financial independence before focusing on wealth for future generations. We begin by discussing the need to establish a solid financial foundation for yourself first, covering goals like education, retirement, and potential medica...

In this episode of Thimbleberry U , Jon Gay and Amy Walls dive into the differences between investment advice and financial advice, a distinction often misunderstood. Amy starts by explaining that investment advice primarily focuses on managing and growing an investment portfolio. This type of advice is transactional, with recommendations on specific actions—buying, selling, or holding certain sec...

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...