Tag Archives: #Taxes

Feature 2021

61. Estate Planning for Concentrated Equity Positions with Aaron Rubin

Though it may seem like a very distant and high-class problem that only the super-wealthy among us will ever have to contend with, for many tech workers who have accumulated a significant sized stake in their employer, it is not unlikely that estate taxes are something they will have to consider as a part of their overall financial plan. In fact, with the number of bills currently floating around the halls of Congress with the intention to increase tax revenue by lowering the estate and gift tax thresholds, there could be significantly more Americans who will be impacted by this “problem” soon enough.

In this episode, Malcolm Ethridge speaks with Aaron Rubin, a partner at Werba Papier, about some of the lesser-known estate planning challenges facing those with concentrated equity positions. Aaron also shares some of the more common mistakes he sees clients make prior to and immediately following an IPO that could be avoided with proper planning.

Aaron discusses: 

  • How to design a plan that keeps more of your money in your pocket and out of the hands of the IRS
  • The interesting and unique things he has seen people do following an IPO
  • Who should be concerned about qualified small business stock
  • What an intentionally defective trust is and how to apply it
  • And more


Connect With Aaron Rubin:

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About Our Guest:

Aaron Rubin is a partner at Werba Papier, a wealth management firm that caters to pre-IPO executives and early employees. Prior to his current firm, Aaron spent time at Deloitte where he worked on trust and estates and honed his skills in their private client advisory. He also received his JD from the University of Illinois. In 2019, he published Financial Adulting, a guide to help young professionals navigate the challenges of taxes and investments in estate planning.

Feature 2021

60. The Ins and Outs of Crypto Taxes with Micah Fraim

As anyone who has ever bought and sold any sort of digital asset in the last couple years can attest, the rules and regulations around reporting those transactions to the IRS can be very fuzzy. Coupled with the lack of information made available by the IRS itself, and the lack of general knowledge and adoption of crypto by the accounting community, it can be very tough for investors to make heads or tails of it all. 

At best, you manage to stumble across a couple of really helpful twitter posts or youtube explainer videos offering solid tidbits of information that may or may not be directly applicable to your individual circumstances. But at worst, you make a mistake in reporting your transactions in one year, that ultimately opens up your returns from previous years to scrutiny, and you find yourself in the middle of a full-blown audit with no idea how you got there.

In this episode, Malcolm Ethridge speaks with Micah Fraim, CPA and crypto enthusiast, about the taxation of crypto. Micah shares his knowledge about how crypto and NFTs are taxed, how to save money on taxes when investing in crypto, why you should stay up to date on the ever-changing IRS taxation policies about crypto, and how to track activity across multiple digital wallets without using a platform like Coinbase.

Micah discusses: 

  • How crypto and NFT trades are taxed today
  • How to take advantage of the current crypto winter to save on taxes
  • Why he is such a fan of cryptos and their future long-term
  • Some recommendations for how to tack crypto activity and keep good records across multiple digital wallets
  • And more


Connect With Micah Fraim:

Connect With Malcolm Ethridge:

About Our Guest:

Micah Fraim is the founder of Fraim Cawley & Company. Micah is a certified public accountant who works with small business owners on preparing tax returns and offers more advanced tax planning. In addition, he is also a self-proclaimed crypto enthusiast and has recently published the book, Decryptifying Crypto Taxes.


Feature 2021

21. Accessing the Value of Your Concentrated Stock Position with Anthony LoBalbo

There are ways that you can access the value of your concentrated stock positions and avoid the huge tax bill. 

In this episode, Malcolm Ethridge sits down with Anthony LoBalbo, regional manager with Schwab Bank, as they discuss the securities backed line of credit. Malcolm and Anthony discuss how it works and how you could be taking advantage of it yourself.

Anthony discusses: 

  • Situations when having an S Block makes sense
  • The application process and how long it takes to have the line open and available 
  • How amount extended through the line is determined
  • Interesting ways that this line of credit has been used in the past
  • And more

Connect With Anthony LoBalbo:

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Feature 2021

20. Managing the Tax Implications of Your Employer Stock and Options with Megan Gorman

Taxes are something that we will never be able to fully avoid, so it is imperative that we understand how they are going to impact all aspects of our finances, and prepare to manage them to pay as little as possible. 

In this episode, Malcolm Ethridge is joined by Megan Gorman, founder and managing partner of Chequers Financial, as they discuss the tax implications of managing your employer stock and options. Megan helps educate you on the things your employer might not, so you can be prepared to make the best decisions for your situation. 

Megan discusses: 

  • Her passion for working with taxes and stock options
  • Advice for how individuals can see the bigger picture when it comes to taxes
  • How the 10b5-1 fits into tax planning with employer stock options
  • The best ways to receive equity compensation
  • And more

Connect With Megan Gorman:

Connect With Malcolm Ethridge:

About Our Guest:

Megan is the founding partner of Chequers Financial Management, a fee-only planning firm that specializes in high net worth and ultra-high net worth families in San Francisco, California. Chequers focuses on establishing long term relationships with families and helps them navigate through tax, estate, liquidity and investment planning. Megan heads the firm’s family office services practice.

Feature 2021

19. Financial Planning Rules that Everyone With Employer Stock & Options Need to Know with Bruce Brumberg

Oftentimes, there is a significant gap between the information that companies who offer stock based comp to their employees think they are providing versus the amount of information those employees feel that they receive. And this information gap  can make it hard to know which end is up.

In this episode, Malcolm Ethridge is joined with Bruce Brumberg, co-founder and editor in chief of MyStockOptions.com, as they discuss some of the financial planning rules of thumb when it comes to stock options. Malcolm and Bruce go deep on some of the more technical factors that plan participants should consider before making decisions regarding their equity comp.

Bruce discusses: 

  • Setting goals to manage equity comp
  • The importance of learning what happens when you leave your company and telling your family members
  • Exceptions to the standard rule of waiting as long as possible to exercise your stock options
  • The tax bracketing approach to stock options
  • And more

Connect With Bruce Brumberg:

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About Our Guest:

Bruce Brumberg has devoted most of his professional career to making complex legal and tax concepts understandable to people who do not enjoy reading the securities laws or the Internal Revenue Code. In myStockOptions.com, Bruce created the premier source of web-based educational content and tools on stock compensation (stock options, restricted stock, and employee stock purchase plans) for plan participants, financial advisors, and companies. The creation and management of the website combine Bruce’s in-depth understanding of stock plans with his proven ability to present and explain complex legal, financial, human-resource, and compensation topics using innovative techniques.

Feature 2021

18. The Importance of Diversification When Managing Your Employer Stock & Options with Bill Dillhoefer

Your equity compensation can have an outsized impact on your overall portfolio, so it is key to set your strategy ahead of time and find tools that will help you stick to your plan to diversify.

In this episode, Malcolm Ethridge sits down with Bill Dillhoefer, CEO of Net Worth Strategies Inc, as they discuss the importance of diversification when managing employer stock and options. Bill introduces his platform, StockOpter.com, and how it helps financial planning professionals make decisions on behalf of clients who are paid in equity.

Bill Dillhoefer discusses: 

  • The information gap between employers and their employees who are paid in equity, and why it exists
  • The importance of reviewing and understanding the grant document
  • Forfeiture value and why you need to understand it
  • How concentration risk impacts your employer stocks and options
  • How to set a strategy to diversify a concentrated equity position 
  • And more


Connect With Bill Dillhoefer:

Connect With Malcolm Ethridge:

About Our Guest:

The president and CEO of Net Worth Strategies, Bill DIllhoefer has been with the firm since 2000 and became its CEO in January 2018. His firm provides professional equity compensation risk analysis and tax planning tools. Bill is responsible for all business and product development activities for their industry acclaimed “StockOpter” platforms. His goal is to help advisors and their clients make timely, informed, and profitable company stock and option decisions.

Feature 2021

17. The Basics of Equity Compensation with Amy Reback

Navigating the world of equity compensation can be intimidating, but it doesn’t have to. As a participant in an equity compensation plan, a good place to start is by getting acquainted with your plan document and its various terms and conditions.

In this episode, Malcolm Ethridge is joined by Amy Reback, head of Charles Schwab stock plan services, as they discuss the basics of equity compensation. Amy shares rules of thumb and other helpful information that every plan participant needs to know about their equity compensation.

Amy discusses: 

  • The recent trend of more companies offering stock plans to their employees
  • The employer versus the employee when it comes to stock equity
  • How the employee stock purchase plans works and how it differs from other stock plans
  • Recommendations stock participants should be following
  • And more

Connect With Amy Reback:

Connect With Malcolm Ethridge  

About Our Guest:

As Vice President and General Manager of Stock Plan Services, Amy is personally committed to helping ensure client satisfaction. Charles Schwab’s goal is to help stock plan sponsors generate employee pride about being invested in their company. By providing flexible support for employee stock purchase plans and equity awards, the team at Schwab is dedicated to meeting the needs of our plans sponsor clients by offering a range of plan options. 

Feature 2021

14. Investing in Alternative Assets Through Self-Directed IRAs with Patrick Hagen

What else exists that you could be investing your dollars into, other than traditional investments?

How about a franchise, real-estate or even cryptocurrency?

In this episode, Malcolm Ethridge is joined by Patrick Hagen, national director of business development with Strata Trust. The duo discuss alternative investments through self-directed IRAs along with the advantages of using this investment tool and what it really means to be self-directed. 

Patrick discusses: 

  • What a self-directed IRA is and how it works
  • What you can invest in when you use a self-directed IRA
  • How a self-directed IRA is funded and how long it takes
  • The risks involved with using a self-directed IRA
  • And more

Connect With Patrick Hagen:

Connect With Malcolm Ethridge

About Our Guest:

Patrick serves as the National Director of Business Development for STRATA Trust Company, a self-directed IRA custodian that specializes in holding alternative assets for IRA investors. Clients use Strata Trust to invest their IRA funds into ‘alternative’ assets like private equity, real estate, precious metals and private debt. Patrick has been in the self-directed IRA space for over 16 years. He has been the top producer with each firm that he’s worked for.

Feature 2021

9. The Ins and Outs of Donor Advised Funds with Mary Jovanovich

When it comes to charitable giving, there’s more to it than simply writing a check to a few non-profit organizations near the end of the year and claiming a tax deduction.

In this episode, Malcolm Ethridge is joined by Mary Jovanovich, senior relationship manager with Schwab Charitable, as they dive into the

Feature 2021

4. It’s Tax Time. Should You DIY or Hire a Pro? — with Erica James

Do you dread the time of year when you have to file your taxes? Do you feel overwhelmed about how to file or all of the information you need? 

In this episode, Malcolm Ethridge is joined with Erica James, Manager and Client Advisor at SBSB Financial Advisors, and they dive into the conversation about tax time. In this episode, Malcolm and Erica identify when it might be okay for you to DIY your taxes and when you should consider seeing a professional! 

In this episode, you will learn about:

  • The differences between a CPA, EA and Tax Preparer 
  • Making Changes once you have submitted a tax return 
  • Why it is so important to maintain good records 
  • Why you need to do your due diligence when choosing a tax professional
  • And more!

Tune in now as we uncover some important reasons why you might consider doing your taxes DIY or hiring a professional for this once a year activity! 

Resources: MalcomEthridge.com | Malcolm Ethridge | Erica James | SBSB Financial Advisors