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 Financial, breaking down not only what to expect at each stage but also how to make a decision that aligns with our values, personality, and financial goals.

We begin by examining the startup world—fast-paced, creative, and filled with uncertainty. It’s a space for people who love to experiment and thrive in ambiguity. The upside can be big: ownership, impact, and equity at low initial prices. But the downsides—unpredictable income, fewer benefits, and emotional strain—are just as real. Amy shares stories of clients who initially thrived in startup life but found it incompatible with long-term needs like family time or structured days.

Next, we shift to pre-IPO companies, which often represent a middle ground. These firms offer more stability than startups but still retain a sense of mission and momentum. Equity typically comes in the form of RSUs, and while there’s real potential for financial gain, it hinges heavily on IPO timing—something employees can’t always control. Amy emphasizes the importance of planning for delays, setting aside cash, and staying flexible when managing that equity.

Public companies offer clarity and predictability—stable salaries, strong benefits, and slower but more structured growth paths. For professionals seeking balance, or with greater family or financial obligations, this environment often provides the support and stability they need. The culture tends to be more formal, but that predictability can actually empower people to do their best work.

Ultimately, the conversation centers around fit—not which company is best, but which is best for us, right now. Personality, financial goals, and life stage all play a role. A startup might make sense early in a career, while a more structured setting could become the right choice later on. Amy reminds us that romanticizing a company type—or even our own preferences—can lead us astray, and encourages getting honest feedback from those who know us best.

We wrap by reinforcing that job decisions should balance financial and emotional fit. Before accepting an offer, it’s critical to understand the equity structure, total compensation, pace of work, and company culture. Especially in today’s tight job market, doing our due diligence can prevent long-term regret and position us to thrive both professionally and personally.

00:00 - Intro and Episode Setup

00:49 - Startup Culture: Opportunity vs. Chaos

03:19 - Pre-IPO Companies: Growth with Guardrails

06:08 - Public Companies: Structure and Stability

09:27 - It's About Fit: Personality and Life Stage

11:43 - Culture, Pace, and Real-Life Trade-offs

13:43 - When the Job Market is Tight

14:17 - Takeaways: Equity, Compensation, and Culture

16:44 - How to Connect with Thimbleberry Financial

16:57 - Disclaimer and Wrap-Up

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

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 family.

We explore how this dual role adds emotional and financial weight. Many healthcare professionals become the “go-to” child in the family, shouldering time off work, travel, coordination, and often direct financial support. But as Amy reminds us, we can’t pour from an empty cup. Our ability to help others long-term depends on preserving our own financial health first.

We talk through the major financial decisions that come up—care settings for aging parents, sibling coordination, insurance gaps, and legal documents. There’s often an assumption that Medicare will cover long-term care, but it doesn’t, which leads to unexpected financial strain. Amy also highlights the importance of separating finances, documenting contributions, and maintaining clear records to protect relationships and ensure fairness.

A major theme we come back to is boundaries. Just like in an emergency on an airplane, we must put on our own oxygen mask first. For financial health, that means building a plan for ourselves before helping our parents. That clarity allows us to make better decisions, communicate expectations with siblings, and avoid jeopardizing our own retirement.

We also recognize the strengths healthcare professionals already bring—assessment, planning, communication, and monitoring. These are the same skills needed to manage a family’s financial and care responsibilities. Amy urges listeners to apply their professional mindset to this personal challenge.

Finally, we lay out five concrete next steps: gain financial clarity for both generations, start those tough conversations early, prioritize your own retirement, coordinate insurance and estate planning, and build a team of advisors, including financial planners and elder law attorneys. Sustainable care means both generations are supported—and planning ahead is the only way to get there.

00:00 - Intro
00:14 - The Sandwich Generation in Healthcare
00:49 - Emotional and Financial Weight of Caregiving
02:24 - Financial Decisions When Parents Need Support
04:59 - Sibling Dynamics and Hidden Costs
05:48 - Helping Without Sacrificing Your Retirement
08:33 - Applying Professional Skills to Family Finances
10:42 - Five Concrete Next Steps
12:21 - Sustainable Care Across Generations
12:42 - How to Contact Thimbleberry Financial

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

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 see online is rarely the whole picture. People share the new boat or vacation, not the credit card debt, parental help, or stress behind the scenes.

We also talk about how older stats around side hustles — like claims that 50% of people have them — still influence how we think today, despite more accurate 2025 data showing only 25% of adults actually have one. And affluence is often funded by invisible resources like family wealth or debt, which makes comparisons misleading and self-defeating.

Psychologically, we’re wired for social comparison, but our brains focus upward. We look at those doing better, rarely at those with less. That creates ever-shifting benchmarks for “enough,” raising the bar as others share their wins. On top of that, algorithms feed us more of what we engage with — usually success stories — which can skew our sense of what’s normal.

Amy walks us through the reality: the national savings rate is low (4–5%), emergency funds are thin (1 in 5 adults can’t handle a $100 surprise), and credit card debt is at an all-time high in 2025. Even those who look like they have it all together might be stretched thin.

Why does this all sting so much? Because we’ve tied our identity to our finances. Falling behind feels like failure. It hits at our self-worth and creates a stress loop: we feel behind, we spend to catch up, and that spending adds more stress. It’s emotional and financial burnout.

So how do we break the cycle? First, redefine goals based on our own needs. Track progress against your own goals — like building savings or reducing debt — not against someone else’s vacation photos. Curate your feeds to remove content that sparks comparison. Write down what “enough” looks like for you in terms of comfort, flexibility, and fun. Celebrate quiet wins like financial stability, and be cautious of lifestyle creep when your income rises.

Lastly, Amy reminds us to stay curious instead of competitive. Learn from others without turning it into a race. Real wealth and well-being come from clarity, control, and peace of mind — not what someone else posts online.

00:00 – Intro
00:35 – Why social media skews our perception
01:30 – Debt and side hustle myths
03:00 – Why we compare ourselves psychologically
04:50 – The illusion of success online
05:50 – What’s really going on financially nationwide
06:50 – Why it hurts to feel behind
07:40 – The emotional and financial cost of comparison
08:45 – How to reset your goals
09:40 – Avoiding lifestyle creep
10:25 – Final takeaways and closing

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.