ThimbleberryU
Business & Finance
About
Financial planning is all about vision - what do you want for the rest of your life? Amy Walls of Thimbleberry Financial helps clients paint that picture every day. And it's what we will do in this podcast.
Episodes
- Aging Gracefully in Tech
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…
- When One Partner Retires First
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.…
- Employee Stock Purchase Plans - Are They Worth The Effort?
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…
- The Tax Time Bomb In Your Retirement Accounts
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) a…
- Tax Time Stress Test- Proactive Planning for Equity and Bonuses
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, equi…
- ThimbleberryU 153 - Confidence Under Uncertainty for Healthcare Professionals
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…
- Tech Burnout Blueprint: Aligning Money With Mental Health
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…
- The Shift From Saver to Spender - Transitioning Into Retirement
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—…
- 10 Lessons from 10 Years at Thimbleberry Financial
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…
- Choosing Between Tech Companies
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 corpor…
- Caring for Aging Parents While Planning Your Own Retirement
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 “san…
- Why It Feels Like Everyone Has More Money
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…
- RSUs in 2025 Explained
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 in…
- T-Bill Myths on Social Media
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,” “War…
- Money Habits That Stick - Gamifying Savings (Part 2)
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 sav…
- Money Habits That Stick- Gamifying Savings (Part 1)
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 the…
- The Tax Return Mistake That Undermines a Backdoor Roth Strategy
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 t…
- Estimated Taxes — What They Are Why They Matter and How to Handle Them
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 le…
- Estate Planning Pitfalls and How To Avoid Them (Part 2)
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 on…
- Estate Planning Pitfalls And How To Avoid Them (Part 1)
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…
- HealthCare: Preparing Financially for Career Burnout
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…
- Equity Compensation - How and When To Walk Away
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…
- She Will Outlive You: Stop Putting Off The Conversation
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 ch…
- What Makes a Financial Plan Work - And What Gets In The Way
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 intentio…
- What To Do When Someone Dies
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…
- What is an 83(b) Election?
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 ca…
- Navigating Family Conversations About Aging and Finances
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. Ma…
- The Thimbleberry Virtual Experience
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 mo…
- Creating Income and Legacy - A Case Study
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 mea…
- NIH Funding Changes and Job Security
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…
- Why Amy Does What She Does
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 m…
- Why a HELOC is NOT A Cash Reserve
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 smart…
- Tricks to Make 2025 Your Most Financially Successful Year Yet
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…
- Teaching Kids Financial Responsibilty, Part 2
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 under…
- Teaching Kids Financial Responsibility, Part 1
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 th…
- Navigating an Early Retirement Offer
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…
- Building Intergenerational Wealth
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 generatio…
- Investment Advice vs Financial Advice
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 man…
- Retirement Myths Debunked, Part 2
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, start…
- Retirement Myths Debunked, Part 1
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 i…
- Lump Sum Investing vs Dollar Cost Averaging
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…
- Making More and Better Decisions
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 o…
- Is Your Portfolio Too Concentrated?
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…
- Safeguarding Senior Finances
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 se…
- Retirement Distributions: A Case Study
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 retiremen…
- Balancing Equity Compensation and Life: Tech Professionals 6 of 6
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, emp…
- Five Myths of Retirement Planning
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, the…
- NQSOs: Simplifying Equity Comp: Tech Professionals 5 of 6
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 sim…
- Embracing a Future Phase of Life
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 visualizin…
- Mastering ISOs: Tech Professionals 4 of 6
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 equi…