A $43,000 surprise tax bill turned into a triple win & here’s exactly how we did it…

When an unexpected bonus creates a massive tax problem, most high earners simply write the check and move on. But what if that problem could become an opportunity?

In this case study, we walk through a real pattern I see regularly: a high earner with RSUs and ESPP shares facing significant underpayment penalties, underwater company stock sitting idle, and years of charitable giving with no real strategy behind it.

By coordinating three moves—tax loss harvesting, a Donor Advised Fund contribution, and strategic portfolio rebalancing—we eliminated penalties, cut the tax bill by over $20,000, diversified concentrated holdings, and built a multi-year charitable giving plan.

This isn’t about one clever trick. It’s about seeing how the pieces connect and acting before year-end when the strategies still work.

If you have stock compensation and you’ve had a higher income year than expected, this is the kind of planning that changes everything.

Schedule a free Vision Call with our team → https://www.perspective6wealthadvisors.com/matt/

Investment advisory services offered through Savvy Advisors, Inc. Other entities and/or marketing names, products, or services mentioned here are independent of Savvy Advisors, Inc.

#StockCompensation #TaxPlanning #RSUs #FinancialPlanning #RetirementPlanning

Wondering if you’re handling your stock compensation taxes correctly? Let’s build a strategy tailored to your equity → https://www.perspective6wealthadvisors.com/matt/

Stock Compensation Tax Form Checklist → https://perspective6wealthadvisors.com/stock-compensation-tax-checklist/

ESPP: A Comprehensive Guide → https://perspective6wealthadvisors.com/espp-guide/

If you received RSUs, stock options, or ESPP shares in 2025, tax season just got complicated.

Most high earners with equity compensation make one critical mistake: they end up paying taxes twice on the same income because they don’t understand basis adjustments.

In this video, we break down:

Whether you’re with Fidelity, Morgan Stanley, Schwab, or E*TRADE, understanding how your brokerage reports stock sales can save you from costly errors.

If a significant portion of your compensation comes from equity, the standard 22% supplemental withholding rate probably isn’t enough to cover what you’ll actually owe. We’ll show you how to calculate whether you need quarterly estimated payments.

Investment advisory services offered through Savvy Advisors, Inc. Other entities and/or marketing names, products, or services mentioned here are independent of Savvy Advisors, Inc.

Want a tax-efficient plan for your 2026 stock compensation? Let’s build a strategy together → https://www.perspective6wealthadvisors.com/start-here/

If you’re receiving RSUs, stock options, or performance shares in 2026, waiting until tax season to figure out your strategy could cost you tens of thousands in unnecessary taxes.

Most high earners earning $250k+ make the same mistake: they react to stock compensation instead of planning for it.

By the time the first vesting hits, the income is already recognized, the withholding falls short, and the diversification window closes.

In this video, we’ll walk through a four-step framework to help you take control of your equity compensation before it hits your paycheck.

You’ll learn how to:

Whether you’re holding ISOs, waiting on performance shares, or managing quarterly RSU vests, this episode will show you how to turn stock compensation into controlled, tax-efficient wealth building.

If you’re a high earner navigating complex equity compensation and want a personalized plan for 2026, schedule a Vision Call with Perspective 6 Wealth Advisors.

Timestamps:

0:32 – Project What’s Actually Coming

1:48 – Fix the Withholding Problem

3:24 – Divide Into Three Buckets

4:45 – Timing Strategy Matters

Investment advisory services offered through Savvy Advisors, Inc. Other entities and/or marketing names, products, or services mentioned here are independent of Savvy Advisors, Inc.

You’ve probably heard the advice to hold on to your company stock. It feels logical- you work there, you believe in the business, and selling can feel disloyal. But what if that advice is actually putting your financial future at risk?

In this episode, Matt explains why holding too much company stock can quietly become one of the riskiest financial decisions you make. From Silicon Valley Bank to Meta, Matt walks through three clear situations when selling your company stock may be the smarter move. You’ll also learn how taxes, life transitions, and behavioral bias play into these decisions- and how diversification can help protect both your wealth and your peace of mind.

Here’s some of what we discuss in this episode:

The 10–15% Rule – When company stock becomes a concentration problem

0:00 – Intro

1:01 – Scenario 1

3:39 – Scenario 2

6:11 – Scenario 3

8:43 – Behavioral Bias

Resources

Our website: https://www.perspective6wealthadvisors.com/

Phone: (952) 225-0333

Email: [email protected]

Schedule your no-cost consultation: https://www.perspective6wealthadvisors.com/start-here/

Essential Financial Guides

5 Ways to Maximize Your Medtronic 401k Plan Guide: https://perspective6wealthadvisors.com/guide/

Stock Compensation Tax Form Checklist: https://perspective6wealthadvisors.com/stock-compensation-tax-checklist/

ESPP: A Comprehensive Guide: https://perspective6wealthadvisors.com/espp-guide/

Check out our other no-cost financial resources here: https://perspective6wealthadvisors.com/resource-center/

Stay Connected

Check us out on YouTube: https://www.youtube.com/@P6Wealth

LinkedIn: https:// www.linkedin.com/company/perspective-6-wealth-advisors

Investment advisory services offered through Savvy Advisors, Inc. Other entities and/or marketing names, products or services mentioned here are independent of Savvy Advisors, Inc.

Markets don’t move in straight lines, and 2025 proved that once again. In this episode, Matt sits down with Matthew Finley to walk through their 2026 Market Outlook and what investors should realistically expect in the year ahead.

They reflect on the sharp early-year pullback in 2025, the surprising number of new all-time highs that followed, and what long-term data, not headlines, suggest about where markets may be headed next. The conversation covers earnings growth, interest rates, volatility, AI spending, and the difference between healthy risk and speculative fear.

Here’s some of what we discuss in this episode:

Why a 19% drawdown didn’t derail the year 

What 37 new all-time highs really signal 

How earnings growth shapes market expectations 

Understanding volatility vs. long-term returns 

AI, policy risks, and potential market catalysts

0:00 – Intro 

2:03 – 2025 pullback and tariff volatility

4:59 – Earnings growth, forecast ranges, and expectations

7:19 – Intra-year declines and market volatility 

12:00 – AI, profitability, and the “bubble” question 

14:14 – Positive and negative catalysts ahead 

16:30 – Takeaways 

Resources for this episode:

2026 Market Outlook Article:

https://www.perspective6wealthadvisors.com/market-outlook-2026-making-calculated-risks/

2025 Market Outlook Article:

https://www.perspective6wealthadvisors.com/2025-market-outlook-insights-on-navigating-volatility/

Tariff Article:

https://www.perspective6wealthadvisors.com/tariffs-explained-the-good-bad-and-whats-next/

Resources

Our website: https://www.perspective6wealthadvisors.com/

Phone: (952) 225-0333

Email: [email protected]

Schedule your no-cost consultation: https://www.perspective6wealthadvisors.com/start-here/

Essential Financial Guides

5 Ways to Maximize Your Medtronic 401k Plan Guide: https://perspective6wealthadvisors.com/guide/

Stock Compensation Tax Form Checklist: https://perspective6wealthadvisors.com/stock-compensation-tax-checklist/

ESPP: A Comprehensive Guide: https://perspective6wealthadvisors.com/espp-guide/

Check out our other no-cost financial resources here: https://perspective6wealthadvisors.com/resource-center/

Stay Connected

Check us out on YouTube: https://www.youtube.com/@P6Wealth

LinkedIn: https:// www.linkedin.com/company/perspective-6-wealth-advisors

Investment advisory services offered through Savvy Advisors, Inc. Other entities and/or marketing names, products or services mentioned here are independent of Savvy Advisors, Inc.

Diversifying a large stock position without triggering a massive tax bill can feel impossible, but there are advanced strategies designed specifically for this challenge. In this episode, Matt breaks down two powerful but often misunderstood tools: the 351 Exchange and the Exchange Fund. While they sound similar, they serve completely different types of investors and portfolio problems.

You’ll learn how a 351 Exchange can help reorganize an already diversified portfolio into a custom ETF without realizing capital gains. Then, Matt explains how an Exchange Fund can provide much-needed diversification for someone with a highly concentrated stock position, along with the trade-offs, lock-up periods, and accredited investor requirements that come with it.

Here’s some of what we discuss in this episode:

Why selling concentrated positions can trigger massive tax bills

What a 351 Exchange actually is- and who it helps

How Exchange Funds work and why they require a 7-year lock-up

How to decide which strategy fits your situation

0:00 – Intro

1:16 – Overview of 351 Exchange

3:13 – Overview of Exchange Funds

4:12 – Comparing 351 and Exchange

4:52 – How to choose the right strategy

Resources

Our website: https://www.perspective6wealthadvisors.com/

Phone: (952) 225-0333

Email: [email protected]

Schedule your no-cost consultation: https://www.perspective6wealthadvisors.com/start-here/

Essential Financial Guides

5 Ways to Maximize Your Medtronic 401k Plan Guide: https://perspective6wealthadvisors.com/guide/

Stock Compensation Tax Form Checklist: https://perspective6wealthadvisors.com/stock-compensation-tax-checklist/

ESPP: A Comprehensive Guide: https://perspective6wealthadvisors.com/espp-guide/

Check out our other no-cost financial resources here: https://perspective6wealthadvisors.com/resource-center/

Stay Connected

Check us out on YouTube: https://www.youtube.com/@P6Wealth

LinkedIn: https:// www.linkedin.com/company/perspective-6-wealth-advisors

Investment advisory services offered through Savvy Advisors, Inc. Other entities and/or marketing names, products or services mentioned here are independent of Savvy Advisors, Inc.

What does it really take to get a MedTech startup from concept to market? In this episode, Matt sits down with Karandeep Singh Badwal, a UK-based consultant, content creator, and host of The Medtech Podcast. They explore the realities of launching and funding MedTech ventures. Unpacking why early regulatory planning is a competitive advantage, how to avoid underestimating costs, and what founders often miss about sales and reimbursement after regulatory approval.

From raising capital and structuring equity to building quality systems that actually work, this conversation is packed with lessons for founders, investors, and innovators alike!

Here’s some of what we discuss in this episode:

Plan for regulatory early- it’s your moat, not your obstacle

0:00 – Intro and guest background

2:38 – Why regulatory planning early matters

3:48 – The profile of today’s MedTech founders

6:20 – Funding realities & underestimated costs

9:59 – Building a funding roadmap

13:25 – Structuring equity & common mistakes

15:41 – Why regulatory approval ≠ sales

18:30 – Angel investing & blended funding strategies

21:23 – What happens after 510(k) approval

25:38 –EU vs. US pathways

28:07 – Karandeep’s personal passions & closing thoughts

Connect with Karandeep:

https://karandeepbadwal.com/

Other Resources

Our website: https://www.perspective6wealthadvisors.com/

Phone: (952) 225-0333

Email: [email protected]

Schedule your no-cost consultation: https://www.perspective6wealthadvisors.com/start-here/

Essential Financial Guides

5 Ways to Maximize Your Medtronic 401k Plan Guide: https://perspective6wealthadvisors.com/guide/

Stock Compensation Tax Form Checklist: https://perspective6wealthadvisors.com/stock-compensation-tax-checklist/

ESPP: A Comprehensive Guide: https://perspective6wealthadvisors.com/espp-guide/

Check out our other no-cost financial resources here: https://perspective6wealthadvisors.com/resource-center/

Stay Connected

Check us out on YouTube: https://www.youtube.com/@P6Wealth

LinkedIn: https:// www.linkedin.com/company/perspective-6-wealth-advisors

Investment advisory services offered through Savvy Advisors, Inc. Other entities and/or marketing names, products or services mentioned here are independent of Savvy Advisors, Inc.

Did you know two investors could earn the same average return, pay the same fees, and still retire with very different outcomes? In this episode, Matt explains why sequence of returns risk is one of the most important concepts to understand within 5–7 years of retirement. You’ll see real examples of how early losses can quietly drain decades of savings, and why the order of your returns matters just as much as the returns themselves.

Here’s some of what we discuss in this episode:

Why timing matters just as much as returns in retirement investing

0:00 – Intro

2:45 – Similar Portfolios, Different Results

3:59 – Negative Returns

8:10 – $1 Million Sample Portfolio

10:50 – Reducing Sequence of Returns Risk

15:43 – Summary

Other Resources

Our website: https://www.perspective6wealthadvisors.com/

Phone: (952) 225-0333

Email: [email protected]

Schedule your no-cost consultation: https://www.perspective6wealthadvisors.com/start-here/

Essential Financial Guides

5 Ways to Maximize Your Medtronic 401k Plan Guide: https://perspective6wealthadvisors.com/guide/

Stock Compensation Tax Form Checklist: https://perspective6wealthadvisors.com/stock-compensation-tax-checklist/

ESPP: A Comprehensive Guide: https://perspective6wealthadvisors.com/espp-guide/

Check out our other no-cost financial resources here: https://perspective6wealthadvisors.com/resource-center/

Stay Connected

Check us out on YouTube: https://www.youtube.com/channel/UCZFSiozlOWNDN0PbgF6HzSA

LinkedIn: https:// www.linkedin.com/company/perspective-6-wealth-advisors

Investment advisory services offered through Savvy Advisors, Inc. Other entities and/or marketing names, products or services mentioned here are independent of Savvy Advisors, Inc.

Roth conversions can be a powerful tax strategy, but are they the right move when you’re just about to retire? In this video, Matt walks through a real-life case study to test that very question. Using Jerry and Ruth Crawford’s $7.3 million portfolio, he explores different strategies, from converting everything at once to filling tax brackets little by little.

Here’s some of what we discuss in this episode:

Full Roth conversion vs. phased approach

Why converting all at once can reduce portfolio growth

Lifetime tax savings with bracket targeting

Impact of delaying Social Security to age 70

Flexibility and legacy benefits from tax-free Roth assets

0:00 – Intro

0:47 – Case Study

2:47 – Full Roth conversion

3:44 – Partial conversion

7:26 – Delaying Social Security

8:45 – Flexibility and legacy benefits

Other Resources

Our website: https://www.perspective6wealthadvisors.com/

Phone: (952) 225-0333

Email: [email protected]

Schedule your no-cost consultation: https://www.perspective6wealthadvisors.com/start-here/

Essential Financial Guides

5 Ways to Maximize Your Medtronic 401k Plan Guide: https://perspective6wealthadvisors.com/guide/

Stock Compensation Tax Form Checklist: https://perspective6wealthadvisors.com/stock-compensation-tax-checklist/

ESPP: A Comprehensive Guide: https://perspective6wealthadvisors.com/espp-guide/

Check out our other no-cost financial resources here: https://perspective6wealthadvisors.com/resource-center/

Stay Connected

Check us out on YouTube: https://www.youtube.com/channel/UCZFSiozlOWNDN0PbgF6HzSA

LinkedIn: https:// www.linkedin.com/company/perspective-6-wealth-advisors

Investment advisory services offered through Savvy Advisors, Inc. Other entities and/or marketing names, products or services mentioned here are independent of Savvy Advisors, Inc.

Have you ever maxed out your 401k and thought, ‘Where else can I put money that grows tax-free?’ If you’re a high earner, especially working in MedTech or the corporate world, this strategy might change the way you save for retirement. Matt breaks down one of the most powerful (and often overlooked) retirement strategies available today: the Mega Backdoor Roth. It’s a legal workaround for those who can’t contribute directly to a Roth IRA and are already hitting their 401k limits midyear.

Here’s some of what we discuss in this episode:

Understanding the Mega Backdoor Roth strategy

How the Mega Backdoor Roth process works

The long-term value of tax diversification

Ideal candidates for this approach

Key pitfalls to watch out for

0:00 – Intro

0:28 – What is a Mega Backdoor Roth?

2:33 – How does it work?

3:35 – Is this a good deal?

3:46 – Why does it matter?

4:21 – Who is this for?

5:05 – Mistake to avoid

Other Resources

Our website: https://www.perspective6wealthadvisors.com/

Phone: (952) 225-0333

Email: [email protected]

Schedule your no-cost consultation: https://www.perspective6wealthadvisors.com/start-here/

Essential Financial Guides

5 Ways to Maximize Your Medtronic 401k Plan Guide: https://perspective6wealthadvisors.com/guide/

Stock Compensation Tax Form Checklist: https://perspective6wealthadvisors.com/stock-compensation-tax-checklist/

ESPP: A Comprehensive Guide: https://perspective6wealthadvisors.com/espp-guide/

Check out our other no-cost financial resources here: https://perspective6wealthadvisors.com/resource-center/

Stay Connected

Check us out on YouTube: https://www.youtube.com/channel/UCZFSiozlOWNDN0PbgF6HzSA

LinkedIn: https:// www.linkedin.com/company/perspective-6-wealth-advisors

Investment advisory services offered through Savvy Advisors, Inc. Other entities and/or marketing names, products or services mentioned here are independent of Savvy Advisors, Inc.