I Guarantee (nothing) . . .

Aaron Rubin
  • 0.0 (0)
  • Investing
  • Updated Monthly

Managing stock options is hard, managing pre-IPO stock options brings it to a different level. We focus on pre-IPO stock, but also explore other financial planning topics. This monthly show keeps it short and impactful.

Episodes

  1. Please don't kill me for talking about Crypto

    06/03/2025

    Please don't kill me for talking about Crypto

    Everyone seemingly has an opinion about crypto currency, and I'm no different. While Bitcoin is all of the rage, the blockchain technology is really what drives this fascinating phenomena.

    7 min
  2. Using Prepaid Variable Forward Contracts to Avoid Tax

    04/30/2025

    Using Prepaid Variable Forward Contracts to Avoid Tax

    The Prepaid Variable Forward Contract (PVF) is a powerful tool in your toolbox to avoid tax. If instead of collaring your stock on your own, you wrapped it in a single contract you could save yourself a lot of heartache . . . and tax.

    7 min
  3. Post Liberation Day Angst

    04/14/2025

    Post Liberation Day Angst

    In this episode we talk about what people can do during down stock markets and dive into the bond market a little bit.

    8 min
  4. Love Me Tender

    03/18/2025

    Love Me Tender

    Tender offers are all the rage. But with a successful tender comes a lot of tax. In this episode we talk about the major types of stock compensation, but specifically focus on Non-qualified Stock options as a particularly interesting opportunity.

    8 min
  5. Fail to the Chief?

    03/04/2025

    Fail to the Chief?

    I discuss whether Trump is a dictator and what actions should and should not be taken. It's a crazy time to be in the market.

    8 min
  6. How to Avoid Tax on RSU Income

    01/15/2025

    How to Avoid Tax on RSU Income

    It's hard when it comes to avoiding tax on RSU income, however, it can be done. Some methods are more tried and true, others involve more aggressive tax positions.

    17 min
  7. ISOs: Exercise Early, but Not Often

    01/09/2025

    ISOs: Exercise Early, but Not Often

    January is known as ISO exercise month. While I haven't seen any Hallmark card commemorating the holiday, those with ISOs need to know the benefits of using time to create a conservative exercise strategy.

    9 min

  8. 12/03/2024

    Will Tariffs Tank the Economy

    The tough Trump tariff talks have a lot of people worried about the economy, the market, and inflation. What if the President actually goes through with it?

    9 min

  9. 11/07/2024

    The 2026 Tax Crystal Ball

    With Republicans in control of the government for the next two years, what do we expect to happen with the expiring tax cuts from 2018?

    5 min

  10. 11/07/2024

    Does the 2024 Election Really Matter?

    It's deja vu all over again. The market popped both times after Trump was elected, but what does that really mean?

    6 min

  11. 10/29/2024

    The Adventure Begins: Stock Options and AMT

    What makes a stock option a stock option? How are stock options generally taxed?

    8 min
  • 11 Episodes

About

Managing stock options is hard, managing pre-IPO stock options brings it to a different level. We focus on pre-IPO stock, but also explore other financial planning topics. This monthly show keeps it short and impactful.

Information

  • Creator
    Aaron Rubin
  • Years Active
    2024 - 2025
  • Episodes
    11
  • Rating
    Clean