ThimbleberryU

In this episode of ThimbleberryU, we dive into a common and costly mistake that often undermines the effectiveness of the backdoor Roth IRA strategy. We begin by establishing that the strategy itself is sound—used by high-income earners to legally sidestep income limits on Roth IRA contributions—but the pitfall lies in the tax return process, particularly in how the transaction is reported to the IRS.

We walk through how the strateg...

In this episode of ThimbleberryU, we dive into a topic that often catches even financially savvy people off guard—estimated taxes. Many assume taxes are fully handled through paycheck withholdings, but we unpack why that assumption can lead to nasty surprises, especially for professionals in tech and healthcare.

We start by defining what estimated taxes are: quarterly payments made directly to the IRS when withholding isn’t enough t...

In this episode, we pick up where we left off—diving into the second half of the top ten estate planning mistakes people make and how to avoid them. Trusts are where we pick up the conversation, and we emphasize that they are tools, not one-size-fits-all solutions. Using the wrong trust, or one that isn’t necessary, can actually create more problems than it solves. We stress the importance of intentionality—choosing the right tool ...

Today, we look at the first five of ten common estate planning pitfalls that many people either ignore or misunderstand, and we lay out the real-life consequences of those mistakes. Estate planning is important not in terms of wealth, but in terms of reducing stress and preserving relationships when someone passes away. Whether or not someone is wealthy, a proper estate plan can prevent delayed decisions, misallocated assets, and e...

In this episode, we dive into a topic that’s becoming more and more urgent: how healthcare professionals can financially prepare for the possibility of career burnout. We know from data and personal experience with clients that burnout is hitting this sector hard—over 50% of healthcare professionals report symptoms, and a significant number are considering stepping away from their roles entirely. So, we tackle this issue head-on, n...

In this episode, we tackle one of the most significant financial decisions tech professionals face: knowing when and how to walk away from a job—whether that's to retire or move to another opportunity—especially when equity compensation is in the mix. We emphasize the mental and financial distinction between retiring permanently and transitioning to a new firm. Retirement means permanently stepping away from income and needing a lo...

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 peace of mind to both people involved.

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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 reserving space for strategic plann...

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 cases of a home passing, 911 or hos...

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 at the time of the grant rather than...

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 financially secure, who will make decisions,...

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 their tech-savvy and healthcare-focu...

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 but face challenges in optimizing t...

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 take to gain control over their financ...

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 until his passing when she was six....

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 credit card, but with a variable intere...

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 maximizing tax-advantaged contribution...

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 discussions to a child’s age and capacity....

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 shouldn't always be tied to financial...