Maximize Your Equity And Benefits In Tech [Part 14] - Stock Option Special Tax Considerations

When working at an early-stage startup, certain tax strategies can unlock major financial advantages—if you plan ahead. Here are the core points from the lesson:

- Qualified Small Business Stock (QSBS) can allow up to $10 million or 10x your basis in tax-free capital gains if you meet specific conditions, like holding actual shares for five years and your company having under $50M in assets at grant
- Early exercise and filing an 83(b) election can start the QSBS clock early and lock in low tax values, but they come with financial commitment and risk if you leave before fully vesting
- The 83(b) election must be filed within 30 days of exercising options and doesn't accelerate the two-year holding clock required for qualified ISOs
- Only $100K worth of ISOs can vest annually for favorable tax treatment—going above that limit risks converting some to NSOs with different tax implications

Next steps with Andy:

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Maximize Your Equity And Benefits In Tech [Part 13] - Stock Option Basics

Stock options offer exciting upside but come with layers of tax complexity depending on type and timing. Here are the core points from the lesson:

- Private company stock options come in two forms: incentive stock options (ISOs) and non-qualified stock options (NSOs), each with different tax rules
- NSOs trigger ordinary income tax at exercise on the spread between strike price and fair market value, with additional capital gains tax upon sale
- ISOs can offer better tax treatment if held for 2 years from grant and 1 year from exercise, avoiding ordinary income tax but potentially triggering alternative minimum tax (AMT)
- Selling ISOs in the same year as exercising can help avoid AMT, but splitting the tax years may result in both AMT and ordinary income tax, creating a worst-case scenario

Next steps with Andy:

- [Connect with Andy on LinkedIn](https://www.linkedin.com/in/andymoranio)
- [Leave feedback and/or sign up for Andy’s newsletter](https://subscribepage.io/taroequitycourse)
- [Schedule a consultation](http://adastrafp.com/contact-us/)

Maximize Your Equity And Benefits In Tech [Part 12] - RSUs (Private Company Equity)

Private company RSUs can be rewarding but come with unique structures, tax challenges, and limited liquidity options. Here are the core points from the lesson:

- Most private RSUs are double-trigger, requiring both time-based vesting and a liquidity event, unlike public RSUs which are typically single-trigger
- Single-trigger RSUs in private companies can create tax issues if you owe taxes on illiquid shares you can’t sell
- Liquidity events like tender offers, IPOs, direct listings, or acquisitions are when real decision-making occurs, though each comes with restrictions like lock-up periods or partial sell limits
- IPOs typically involve a six-month lock-up period, while direct listings may allow earlier sales and fewer constraints
- It’s essential to plan for taxes—sell-to-cover elections may not fully satisfy tax liability due to lower default withholding rates on equity compensation

Next steps with Andy:

- [Connect with Andy on LinkedIn](https://www.linkedin.com/in/andymoranio)
- [Leave feedback and/or sign up for Andy’s newsletter](https://subscribepage.io/taroequitycourse)
- [Schedule a consultation](http://adastrafp.com/contact-us/)

Maximize Your Equity And Benefits In Tech [Part 11] - Insider Trading Considerations

Insider trading rules can create real constraints on when and how you can sell company stock, especially for those with access to sensitive information. Here are the core points from the lesson:

- Insider trading laws prohibit trading on material non-public information, and companies often enforce blackout periods to limit employee risk
- Executives and directors face stricter requirements, including preclearance, holding periods, and detailed SEC reporting (e.g., Forms 4, 144)
- A 10b5-1 plan allows for pre-scheduled trades made while not in possession of inside info, offering a compliant path to selling equity under constraints

Next steps with Andy:

- [Connect with Andy on LinkedIn](https://www.linkedin.com/in/andymoranio)
- [Leave feedback and/or sign up for Andy’s newsletter](https://subscribepage.io/taroequitycourse)
- [Schedule a consultation](http://adastrafp.com/contact-us/)

Maximize Your Equity And Benefits In Tech [Part 10] - Strategy (ESPP)

ESPPs can offer significant value, but deciding when to sell requires more nuance than it may seem at first glance. Here are the core points from the lesson:

- If there’s no holding period requirement, selling immediately after purchase can yield guaranteed gains, especially with discounts and lookback provisions
- Holding ESPP shares introduces market risk and complexity, and your decision should reflect whether you’d buy the stock outright if given the equivalent in cash
- A holding period aligned with qualified disposition rules may offer better tax treatment—but not always; in some cases, a disqualifying disposition results in lower overall tax
- When stock declines during the offering but rebounds before sale, the tax owed under a qualified disposition may be higher due to how ordinary income is calculated from the offering price rather than purchase price

Next steps with Andy:

- [Connect with Andy on LinkedIn](https://www.linkedin.com/in/andymoranio)
- [Leave feedback and/or sign up for Andy’s newsletter](https://subscribepage.io/taroequitycourse)
- [Schedule a consultation](http://adastrafp.com/contact-us/)

Maximize Your Equity And Benefits In Tech [Part 9] - Taxes (ESPP)

Selling stock from your Employee Stock Purchase Plan (ESPP) can lead to very different tax outcomes depending on timing. Here are the core points from the lesson:

- A disqualifying disposition (selling within 1 year of purchase or 2 years of the offering date) results in ordinary income tax on the discount and short-term capital gains on additional profits
- A qualifying disposition (selling after both 1 year from purchase and 2 years from offering) splits the gain into lower-taxed long-term capital gains and a smaller portion of ordinary income
- 1099-B forms often underreport your cost basis, so you may need to correct it using Form 8949 to avoid paying tax twice on the same income

Next steps with Andy:

- [Connect with Andy on LinkedIn](https://www.linkedin.com/in/andymoranio)
- [Leave feedback and/or sign up for Andy’s newsletter](https://subscribepage.io/taroequitycourse)
- [Schedule a consultation](http://adastrafp.com/contact-us/)

Maximize Your Equity And Benefits In Tech [Part 8] - What, How, Why (ESPP)

Employee Stock Purchase Programs (ESPPs) can offer meaningful value, especially at companies that provide favorable terms or lack large RSU grants. Here are the core points from the lesson:

- ESPPs let employees buy company stock at a discount (up to 15%) with a $25,000 annual contribution cap and often include “lookback” provisions to buy at the lower price between the start and end of the offering period

- Programs with multiple purchase periods inside long offering windows—like those at Adobe or NVIDIA—can dramatically increase the value of purchases if the stock appreciates

- Some companies may impose holding periods before you can sell shares, so it's essential to understand your specific plan’s rules before committing

Next steps with Andy:

- [Connect with Andy on LinkedIn](https://www.linkedin.com/in/andymoranio)
- [Leave feedback and/or sign up for Andy’s newsletter](https://subscribepage.io/taroequitycourse)
- [Schedule a consultation](http://adastrafp.com/contact-us/)

Maximize Your Equity And Benefits In Tech [Part 7] - Other Considerations (RSUs/Bonuses)

Even with a solid RSU strategy in place, there are a few overlooked tax and compliance details that can complicate things. Here are the core points from the lesson:

- Insider trading policies may limit your ability to auto-sell or manually sell RSUs immediately upon vesting, leading to short-term gains or losses you can’t always control
- Wash sale rules can disallow losses if you repurchase the same stock within 30 days of a sale, which can easily happen with monthly vesting schedules
- Incorrectly reporting RSU-related wash sales on your taxes may go unnoticed, but technically violates IRS rules and can affect your cost basis going forward

Next steps with Andy:

- [Connect with Andy on LinkedIn](https://www.linkedin.com/in/andymoranio)
- [Leave feedback and/or sign up for Andy’s newsletter](https://subscribepage.io/taroequitycourse)
- [Schedule a consultation](http://adastrafp.com/contact-us/)

Maximize Your Equity And Benefits In Tech [Part 6] - Strategy (RSUs/Bonuses)

Many people default to holding their RSUs without stepping back to ask whether they’d actively choose to buy company stock with a cash bonus. Here are the core points from the lesson:

- Since RSUs are taxed as ordinary income upon vesting, treating them like a cash bonus and selling immediately is often a lower-risk strategy—especially when combined with auto-sell and supplemental withholding features some companies offer

- You can also take a more nuanced approach, like retaining a portion based on your net worth, holding for a set period, or setting specific sale triggers, but it's best to define these plans before emotions kick in

- A minimum financial bar is covering tax liability; use safe harbor rules or proactive withholding adjustments to avoid penalties, especially as year-end approaches

- Flow-based budgeting using separate accounts by expense type and timeline can help you allocate RSU income toward irregular goals like large purchases or saving targets

Next steps with Andy:

- [Connect with Andy on LinkedIn](https://www.linkedin.com/in/andymoranio)
- [Leave feedback and/or sign up for Andy’s newsletter](https://subscribepage.io/taroequitycourse)
- [Schedule a consultation](http://adastrafp.com/contact-us/)

Maximize Your Equity And Benefits In Tech [Part 5] - Taxes (RSUs/Bonuses)

Many tech employees misunderstand the tax treatment of RSUs, leading to unexpected bills and avoidable penalties. Here are the core points from the lesson:

- When RSUs vest, their value is taxed immediately as ordinary income—similar to receiving a cash bonus
- Default federal withholding on RSUs is typically 22%, which is often too low for high earners, potentially resulting in underpayment penalties
- To avoid penalties, aim to meet the IRS Safe Harbor rule—usually by paying 110% of last year’s tax liability if your income exceeds $150k

Next steps with Andy:

- [Connect with Andy on LinkedIn](https://www.linkedin.com/in/andymoranio)
- [Leave feedback and/or sign up for Andy’s newsletter](https://subscribepage.io/taroequitycourse)
- [Schedule a consultation](http://adastrafp.com/contact-us/)

Maximize Your Equity And Benefits In Tech [Part 4] - What And Why (RSUs/Bonuses)

Equity compensation takes center stage in big tech careers—here are the core points from the lesson:

- RSUs (Restricted Stock Units) are a major component of compensation in public tech companies and grow more significant with seniority
- They're granted based on stock price at the time and typically vest over several years, often with cliffs and monthly or quarterly schedules
- Vesting structures and timing vary by company; the value ultimately depends on the stock’s price at the time the shares vest
- Companies use RSUs to conserve cash, encourage retention through "golden handcuffs," and align employee incentives with shareholder value

Next steps with Andy:

- [Connect with Andy on LinkedIn](https://www.linkedin.com/in/andymoranio)
- [Leave feedback and/or sign up for Andy’s newsletter](https://subscribepage.io/taroequitycourse)
- [Schedule a consultation](http://adastrafp.com/contact-us/)

Maximize Your Equity And Benefits In Tech [Part 3] - Foundational Tax Concepts

Understanding how taxes work is key to making smart decisions about equity compensation—here are the core points from the lesson:

- Gross income is reduced by payroll taxes and deductions to determine adjusted gross income (AGI) and taxable income, which drives your federal tax liability
- Long-term capital gains (assets held over a year) receive lower federal tax rates than ordinary income, often saving high earners significant amounts
- State tax treatment varies—most states don’t offer preferential rates for long-term gains, and some, like Massachusetts, penalize short-term gains more heavily
- Investment losses can offset gains and up to $3,000 of ordinary income per year, but “wash sale” rules can disallow losses if you repurchase too soon
- The Alternative Minimum Tax (AMT) may kick in if you're using lots of deductions or exercising incentive stock options, so it’s important to model this in advance

Next steps with Andy:

- [Connect with Andy on LinkedIn](https://www.linkedin.com/in/andymoranio)
- [Leave feedback and/or sign up for Andy’s newsletter](https://subscribepage.io/taroequitycourse)
- [Schedule a consultation](http://adastrafp.com/contact-us/)

Maximize Your Equity And Benefits In Tech [Part 2] - The Big Picture

Equity compensation can be a powerful but complex part of your total rewards in tech. Here are the core points from the lesson:

- Startup equity is high risk, with data showing over 60% of startups from 2018 have already shut down, and only a tiny fraction have reached IPO or unicorn status
- Multiple cognitive biases—like endowment effect, loss aversion, and optimism bias—can cloud judgment and lead to poor decisions about holding or selling stock
- Emotional and social factors, such as FOMO, herding behavior, and recency bias, often push people to mirror peers rather than make rational equity decisions
- Selling strategies can range from immediate liquidation to goal-based triggers (e.g., home down payment), percentage-based sales, or predefined holding periods
- It's crucial to plan ahead, especially around liquidity events, and work with financial professionals to optimize tax implications and align decisions with personal goals

Next steps with Andy:

- [Connect with Andy on LinkedIn](https://www.linkedin.com/in/andymoranio)
- [Leave feedback and/or sign up for Andy’s newsletter](https://subscribepage.io/taroequitycourse)
- [Schedule a consultation](http://adastrafp.com/contact-us/)

Maximize Your Equity And Benefits In Tech [Part 1] - Introduction

Hi, I’m Andy​​! 👋 In this course we’re going to cover the most common forms of equity compensation and benefits in tech, break them down, and provide strategies and thought frameworks for helping you maximize them.

- [Connect with Andy on LinkedIn](https://www.linkedin.com/in/andymoranio)

- [Leave feedback and/or sign up for Andy’s newsletter](https://subscribepage.io/taroequitycourse)

- [Schedule a consultation](http://adastrafp.com/contact-us/)

20 Years Of Fighting Procrastination [Part 15] - Conclusion

Congratulations on making it to the end of the course! While watching great content like this feels good - It doesn't actually mean anything unless you put the learnings into practice. With that being said, here's some ideas for "homework" for you:

- Start sleeping consistently every day, even on weekends
- If you have a task or project that will take at least 1 week, decompose it into at least 3 different sub-tasks
- Set up a meeting with yourself on a regular basis to reflect on your productivity
- Go through your calendar, audit all the meetings, and kill as many as you can

If you want to learn how Rahul's cofounder Alex made $750,000 per year at Robinhood working \~35 hour weeks, you can go to the next level and take his much deeper and more concrete productivity course here: [Maximize Your Productivity As A Software Engineer](https://www.jointaro.com/course/maximize-your-productivity-as-a-software-engineer/)

20 Years Of Fighting Procrastination [Part 14] - Reflect

Reflecting regularly is a powerful habit that can dramatically improve your productivity and self-awareness. Here are the core points from the lesson:

- Daily micro-reflections and bi-weekly deep dives help you identify patterns in when and why you're productive or struggling
- Documenting reflections as written artifacts (e.g. notes or voice memos) forces clarity and gives you useful data over time
- Review both the nature of your work and the relationships that support or hinder your progress—productivity often depends on collaboration
- You can keep reflections private, share them with a manager, or even make them public to foster accountability and gain feedback from others

20 Years Of Fighting Procrastination [Part 13] - Your Phone Is A Menace

Your phone can be both a powerful tool and a massive productivity killer—how you manage it makes all the difference. Here are the core points from the lesson:

- To prevent unconscious distractions, keep your phone physically out of reach during deep work and turn off nearly all notifications by default
- Replace passive phone checking with active forecasting—mentally plan what you’ll do next based on the outcome of a task to stay engaged
- Use batching strategies (e.g. scheduled email checks) to reduce context switching and maintain focus
- Aim to move up the PEM framework: from Pleasure (mindless scrolling) → Engagement (being immersed in your craft) → Meaning (working toward a long-term purpose)

20 Years Of Fighting Procrastination [Part 12] - Set Up Your Calendar

Segmenting your calendar with intention can drastically increase your deep work capacity and reduce distraction. Here are the core points from the lesson:

- Decompose your calendar by assigning specific time blocks for high-leverage work, shallow tasks (like email), and recovery to reduce ambiguity and improve clarity
- Avoid scattering meetings across the week—batch them into clusters (especially 1:1s) to preserve longer stretches of focus time
- Use your influence to improve team-wide productivity by suggesting standardized no-meeting days or more structured meeting schedules
- Even if you don’t follow your calendar plan perfectly, the act of time blocking improves your estimation skills and helps build a rhythm for deep work

20 Years Of Fighting Procrastination [Part 11] - Decompose Aggressively

Decomposition is one of the most reliable habits for making progress feel easy, especially when applied daily. Here are the core points from the lesson:

- Breaking down large, ambiguous tasks into small, concrete steps helps reduce mental friction and makes it easier to start taking action
- Practicing decomposition builds leadership skills and supports team collaboration, since assigning scoped work is essential for effective delegation
- Writing down one key task the night before primes your brain to subconsciously begin planning, leading to more clarity and momentum the next morning

20 Years Of Fighting Procrastination [Part 10] - The Simple Playbook For Sleep

Sleep is often underestimated, yet it’s one of the most powerful levers for improving productivity, health, and mental clarity. Here are the core points from the lesson:

- Sleep has greater long-term health impact than alcohol or smoking, and chronic deprivation leads to worse mood, lower energy, and reduced cognitive function
- Treating yourself as “a good sleeper” and following a consistent wind-down routine (e.g. reading, brushing teeth early, reflecting on the next day) can drastically improve sleep quality
- Physical activity, especially group-based with accountability, helps regulate sleep and creates natural productivity deadlines
- Even small efforts like 10–15 minutes of movement or consistent pre-bed rituals can create compounding benefits for both rest and output

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