ThimbleberryU

In this episode of ThimbleberryU, we talk about what a giant IPO like SpaceX could mean for a personal investment portfolio. The conversation starts with common questions many investors ask when a major private company gets ready to go public. Am I missing out? Is my index fund going to own it? Am I exposed to something I do not understand? Amy explains that many people assume an index fund owns t...

In this episode, we talk about what it means to move beyond simply earning a strong paycheck and start building wealth with real intention, especially for people in tech who are in the middle or later stages of their careers. We start with the idea that success can remove urgency. Early on, financial decisions feel obvious because everything is new and growing. Later, income is steady, accounts ar...

Today, Amy and Jag look at a financial risk that is easy to ignore because it does not feel urgent in the moment: the cost of doing nothing. In this episode, we focus on how delays in financial decisions can quietly create long term consequences, especially for healthcare professionals who are used to acting quickly at work but may postpone choices in their own financial lives. The central idea is...

Careers in technology change as professionals move into their 40s and 50s. Early in a tech career, rapid change feels exciting. New tools, companies, and opportunities create momentum. Over time that same pace can begin to feel heavy. Many professionals start asking different questions. They wonder how long their skills will stay valuable, whether companies will continue to seek their experience,...

We discuss a situation many couples imagine will be simple but rarely unfolds that way in real life: retirement timing. Many couples picture both partners stepping away from work at the same moment and beginning the next chapter together. In healthcare households, however, careers often evolve differently. Physical demands, shift schedules, burnout, or changes in job roles can lead one partner to...

In this episode, we take a closer look at Employee Stock Purchase Plans and ask a simple but important question: are they worth the effort? Many people in tech see ESPPs during open enrollment, feel overwhelmed by the language, and quietly opt out. Why does that happen? Well, ESPPs sit in an awkward middle space. They are not large enough to feel exciting like salary, bonuses, or RSUs, but they ar...

In this episode, we talk about the tax time bomb hiding inside retirement accounts for healthcare professionals. We focus on clinicians who have done everything right:.you saved consistently. You deferred income. You maximized our 403(b) and 457(b) plans. But we explain how those smart decisions can create large tax consequences later in retirement. Here's the core issue. Decades of tax deferral d...

In this episode of ThimbleberryU , we dig into why tax season can feel particularly overwhelming for tech professionals and how to approach it with less stress and more predictability. We focus on the common sources of tax complexity, equity compensation and bonuses, and offer a simple framework for making tax season less dramatic and, ideally, boring. We start by exploring how tech income is rare...

In this episode of ThimbleberryU , we explore the concept of building and maintaining confidence under uncertainty , especially for healthcare professionals who are already accustomed to high-stress environments. The financial world often mirrors the unpredictability of healthcare. Policy changes, staffing shortages, and burnout are compounded by volatile markets and alarming news cycles. Our focu...

In this episode of ThimbleberryU , we dive into an increasingly common experience for those working in the tech industry: burnout. We begin by acknowledging that tech burnout is unique—fast-paced roles, unpredictable compensation, constant decision-making, and job instability combine to create chronic stress. Amy Walls shares how burnout shows up not only emotionally, but also financially, and how...

In this episode, we explore the emotional and structural challenges that come with transitioning from a lifetime of saving to actually spending in retirement. We focus especially on healthcare professionals—nurses, physicians, and leaders—who have spent their careers making cautious, life-impacting decisions and who now face a very different kind of responsibility: using the money they’ve carefull...

In this milestone episode of ThimbleberryU , we celebrate 150 episodes and the 10-year anniversary of Thimbleberry Financial. Amy Walls reflects on a decade of advising clients and the timeless lessons she’s learned—lessons that go beyond finance and into life, meaning, and the value of simplicity. We open by anchoring the episode in Thimbleberry’s core values, especially simplicity. Amy stresses...

In this episode of ThimbleberryU , we explore a fundamental question for professionals in tech: Which type of company is the right fit for your current stage in life and career? Whether it's a startup, a pre-IPO company, or a public corporation, each environment offers its own opportunities, challenges, and financial implications. Jag walks through the trade-offs with Amy Walls of Thimbleberry Fin...

In this episode of ThimbleberryU , we dive into the growing challenge facing healthcare professionals—the balancing act of caring for aging parents while still preparing for their own retirement. We’re talking directly to those in the “sandwich generation,” especially nurses, physicians, and hospital leaders who are used to caregiving professionally and now find themselves extending that care to f...

Today, Amy Walls and Jag dive into why it feels like everyone around us has more money, more freedom, or more upgrades than we do — and why that perception is often just that: perception. Social media plays a huge role in this feeling. The constant exposure to curated highlight reels makes it easy to believe others are winning financially, while we’re falling behind. Amy points out that what we se...

In this episode of ThimbleberryU, we reset the conversation around RSUs—restricted stock units—and bring it back to the basics while adding context relevant to 2025. We start by defining what RSUs are: a form of equity compensation that incentivizes employees to remain at a company and contribute to its long-term success. These units don’t hold any value until they vest, which typically happens ov...

In this episode of ThimbleberryU , we dive into the hype and misinformation around Treasury bills (T-bills) that’s been circulating across social media platforms. We’ve all seen the claims: “risk-free,” “better than savings accounts,” “Warren Buffett approved,” and “perfect for retirement.” But are they really that simple?  Amy Walls from Thimbleberry Financial breaks down what’s true, what’s misl...

In this episode of ThimbleberryU, we continue our discussion on gamifying savings by shifting from the “why” to the “how.” Last time, we explored the psychology behind gamification. Today, we walk through the specific steps to design a savings game that’s personal, sustainable, and motivating. We begin by stressing the importance of having a vivid goal. It’s not enough to have a vague intention—ou...

We kick off part one of our two-part series by exploring how gamification can make saving money feel less like a chore and more like a motivating challenge. Even high-income earners often feel stuck when it comes to saving, not because they lack discipline, but because they’ve already checked the big boxes—maxed out retirement accounts, built up emergency funds—and then don’t know what to do next....

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...

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 th...

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 inte...

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 de...

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....

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 steppin...