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/)

SWE Internship Survival Guide [Part 19] - The Real Treasure

Internships are a unique chance to grow your network alongside your technical skills. Here are the core points from the lesson:

- The other interns you work with often become valuable long-term connections—professionally and personally
- Shared experiences during an internship create natural bonding opportunities, so don’t miss out by being overly heads-down
- Building your network isn’t just about being social—it’s also about doing great work and being helpful to others

Learn how to build relationships here: [**\[Masterclass\] How To Build Deep Relationships Quickly In Tech**](https://www.jointaro.com/lesson/tyaPFMXPoz2pmzB7OVzt/masterclass-how-to-build-deep-relationships-quickly-in-tech/)

SWE Internship Survival Guide [Part 18] - Plot Your Growth Trajectory

Wrapping up all the advice and strategies into something actionable can feel overwhelming—so this video offers a clear, week-by-week roadmap to help you stay on track throughout your internship. Here are the core points from the lesson:

- **Weeks 1–2**: Embrace your newbie status—ask lots of questions, explore the codebase, and focus on learning, even if it means breaking things (safely)
- **Weeks 3–4**: You should start contributing code more regularly, with fewer basic mistakes in PRs, and begin transitioning from onboarding tasks to your main project
- **Weeks 5–7**: You’re gaining confidence—PR feedback is more meaningful, your code is smoother, and a midpoint check-in should help confirm you’re on track
- **Weeks 7–10**: You’re hitting your stride—code velocity and quality are high, you’re asking sharper questions, and maybe even helping others on the team
- **Weeks 11–12**: Finalize your project, document it, reconnect with your network, and take a moment to enjoy the end of a hard-earned, productive summer

SWE Internship Survival Guide [Part 17] - Midpoint Check-In

When you’re aiming for a return offer as an intern, your final performance review can feel like a high-stakes moment. But it *shouldn’t* feel like a mystery. This lesson focuses on how to avoid surprises by being proactive about getting feedback and tracking your progress during the internship. Here are the core points from the lesson:

- Performance reviews shouldn’t be surprises—interns should proactively schedule a midpoint check-in (around week 5 or 6 of a 12-week internship) to gauge how things are going
- Use this check-in to ask honest questions about how you’re doing, what areas need improvement, and how you’re trending toward a return offer
- Treat it as a formal feedback session: retitle the meeting, extend its duration, and come prepared with your accomplishments and areas for growth
- Ask for clarity on how interns are typically evaluated and where you currently stand—phrasing questions with curiosity can unlock more candid feedback

SWE Internship Survival Guide [Part 15] - AI Tools

With AI tools becoming increasingly embedded in the software development workflow, it’s important for interns to use them wisely without compromising their own growth or credibility. Here are the core points from the lesson:

- Interns should embrace AI tools but avoid over-reliance, as teams are assessing *their* engineering abilities—not the tool’s
- Use of AI must comply with company policies, and interns should always understand and be able to defend the code they submit
- AI is best used for boilerplate and simple tasks, but the intern should remain the core problem solver and decision-maker

SWE Internship Survival Guide [Part 14] - Debugging

Debugging is a vital yet often underestimated skill for software engineers, especially interns who are frequently tasked with bug fixes or need to debug their own code. Here are the core points from the lesson:

- Interns often start with low-priority bugs or tackle backlog issues, making debugging a key part of ramping up and delivering impact
- Effective debugging requires identifying the relevant code, using logs or dashboards, and writing down your hypotheses to stay focused
- Reframing debugging as evidence gathering for a potential question helps you avoid tunnel vision and often leads to discovering the root issue
- Common mistakes include poor organization, incorrect environment setup, and focusing on irrelevant details—clarifying these with teammates is encouraged

Go through the debugging masterclass here: [\[Masterclass\] How To Become A Debugging Master And Fix Issues Faster](https://www.jointaro.com/lesson/ioR6WzamAIUTpySLAr7o/masterclass-how-to-become-a-debugging-master-and-fix-issues-faster/)

Ship & Grow 500k+ User Side Projects [Part 19] - Managing Your Project

If you're just starting off with side projects, especially if you're a junior engineer, it can easily get overwhelming. This lesson teaches you:

- The important thing to never forget about side projects
- The 1 project management tool you absolutely should *not* use to manage a side project
- The 1 simple, organic tool that is probably best to manage your side project and keep track of open tasks
- How to organize your side project with decomposition, shown with an example

Ship & Grow 500k+ User Side Projects [Part 4] - Planning Your Initial Launch: API Example

You have now figured out what should go into your side project MVP (minimum viable product). How do you bring it to life? This lesson teaches you:

- The exact steps to follow to ship your MVP
- What good decomposition looks like, explained with an in-depth example

You can go deeper into the mechanics of software decomposition here: <https://www.jointaro.com/course/level-up-your-code-quality-as-a-software-engineer/break-it-down/>

Ace The ML System Design Interview [Part 9] - Common Problems

While specific interview questions vary, common themes emerge, and preparing for these can significantly improve readiness. Here are the core points from this lesson:

- Scaled recommendation systems are frequently encountered, with core components like filtering, ranking, and embedding computation remaining relevant despite variations in specific use cases
- Adapt recommendation system designs to different contexts, such as local recommendations, where rule-based systems might complement or replace certain machine learning components
- Harmful content detection is another common topic, requiring a feedback loop to generate training data, particularly from ambiguous cases in the "maybe" category
- Be prepared to explain how to handle ambiguous cases, as this demonstrates a deeper understanding of the problem
- Understanding the general concepts behind these two question types will provide a strong foundation for tackling many other interview questions

If you like what Ilya has to say, subscribe to his YouTube for more high-quality ML/AI career guidance: [MLEpath - YouTube](https://go.mlepath.com/taro-youtube-mlepath)

If you want hands-on support from Ilya to crack the FAANG ML interview, join his coaching program: [MLEpath - Coaching Program](https://go.mlepath.com/taro-march-25)

Ace The ML System Design Interview [Part 8] - How To Prepare

Preparing for a machine learning system design interview can feel overwhelming, but a structured approach makes it manageable. Here are the core points from this lesson:

- Identify the specific areas of machine learning likely to be covered in your interview to focus your preparation
- Understand the trade-offs between different machine learning techniques by creating comparison tables outlining their pros and cons
- Conduct a mock interview early in your preparation to establish a baseline and identify areas for improvement
- Address feedback from mock interviews and consider a second mock to gauge progress
- Avoid last-minute cramming—structured preparation over a week or month is far more effective

If you want a mock interview from Ilya, you can book time with him here: [MLEpath - Mock Interviews](https://go.mlepath.com/taro-mocks)

If you like what Ilya has to say, subscribe to his YouTube for more high-quality ML/AI career guidance: [MLEpath - YouTube](https://go.mlepath.com/taro-youtube-mlepath)

If you want hands-on support from Ilya to crack the FAANG ML interview, join his coaching program: [MLEpath - Coaching Program](https://go.mlepath.com/taro-march-25)

Ace The ML System Design Interview [Part 6] - Deployment & Beyond

Discussing deployment and monitoring is a crucial signal of real-world machine learning experience in an interview. Here are the core points from this lesson:

- Familiarize yourself with deployment patterns like shadow mode, A/B testing, and blue-green deployments, understanding their trade-offs and when to apply them
- Monitor both offline (ML engineer-focused) and online (business-focused) metrics, paying close attention to the distribution of inputs and outputs at each stage of a multi-stage system
- Recognize that significant shifts in input or output distributions should trigger immediate attention, as they often indicate real-world changes affecting model performance
- Avoid suggesting online learning unless you have deep expertise, as it can lead to complex follow-up questions
- Be prepared to discuss retraining strategies, as models inevitably need updates over time

If you like what Ilya has to say, subscribe to his YouTube for more high-quality ML/AI career guidance: [MLEpath - YouTube](https://go.mlepath.com/taro-youtube-mlepath)

If you want hands-on support from Ilya to crack the FAANG ML interview, join his coaching program: [MLEpath - Coaching Program](https://go.mlepath.com/taro-march-25)

Ace The ML System Design Interview [Part 7] - Questions For Your Interviewers

Interviews are a two-way street, providing an opportunity to assess whether a company and team are a good fit. Here are the core points from this lesson:

- Prepare thoughtful questions that focus on factors directly impacting your work experience, such as on-call responsibilities and decision-making processes
- Avoid vague questions like "What's the work-life balance like?" and instead probe for root causes, such as the frequency and intensity of on-call duties or whether decisions are made top-down or bottom-up
- Understand the company's decision-making culture to gain insights into potential work-life balance challenges
- Ask targeted questions to get a clearer picture of the team's dynamics and the day-to-day realities of the role
- Take advantage of engineers’ straightforward answers to learn what it’s really like to work at the company

If you like what Ilya has to say, subscribe to his YouTube for more high-quality ML/AI career guidance: [MLEpath - YouTube](https://go.mlepath.com/taro-youtube-mlepath)

If you want hands-on support from Ilya to crack the FAANG ML interview, join his coaching program: [MLEpath - Coaching Program](https://go.mlepath.com/taro-march-25)

Ace The ML System Design Interview [Part 5] - Modeling

Modeling plays a critical role in machine learning system design, with classification and regression being the most frequently encountered problem types in interviews. Here are the core points from this lesson:

- Understand various evaluation metrics, such as precision, recall, F1 score, NDCG, and loss metrics like cross-entropy and focal loss, and know when to apply each
- Be prepared to discuss trade-offs between metrics, particularly precision and recall, and avoid over-optimizing for a single metric
- Recognize the significance of loss metrics, memorizing the equations for cross-entropy and focal loss, and understanding their applications in balanced and imbalanced datasets
- Be ready to discuss model selection, including architecture choices like two-tower models or matrix factorization, and anticipate follow-up questions on optimization techniques and troubleshooting issues like overfitting and vanishing gradients
- Consider a baseline model for comparison if no current system exists, and if there is an existing system, use it as a reference point

If you like what Ilya has to say, subscribe to his YouTube for more high-quality ML/AI career guidance: [MLEpath - YouTube](https://go.mlepath.com/taro-youtube-mlepath)

If you want hands-on support from Ilya to crack the FAANG ML interview, join his coaching program: [MLEpath - Coaching Program](https://go.mlepath.com/taro-march-25)

Ace The ML System Design Interview [Part 4] - Data

Data is the foundation of machine learning, and a thorough discussion of data is essential in any machine learning system design interview. Here are the core points from this lesson:

- Discuss labels, features, and data set splitting, understanding the trade-offs involved in each area
- Explore various methods for generating data labels, such as human annotation, synthetic data, and LLMs, while considering the pros and cons of each approach
- Focus on high-level feature sources, providing relevant examples and selecting predictive features while avoiding sensitive topics
- Understand feature encoding techniques, such as one-hot encoding and embeddings, and their impact on model performance
- Weigh the trade-offs between cross-validation and train-validate-test splits, while considering issues like data leakage and imbalances in the data set

If you like what Ilya has to say, subscribe to his YouTube for more high-quality ML/AI career guidance: [MLEpath - YouTube](https://go.mlepath.com/taro-youtube-mlepath)

If you want hands-on support from Ilya to crack the FAANG ML interview, join his coaching program: [MLEpath - Coaching Program](https://go.mlepath.com/taro-march-25)

Taro Book Club: The Pragmatic Programmer - Session 6

Session Led by [Bikram Kashyap](https://www.linkedin.com/in/kashyapbikram/)

In this #taro-bookclub discussion, we'll go over [**"The Pragmatic Programmer"**](https://www.amazon.com/Pragmatic-Programmer-Journeyman-Master/dp/020161622X) by Andrew Hund & David Thomas

Here's the agenda:

- Design by Contract
- Dead Programs Tell No Lies
- Assertive Programming
- How to Balance Resources
- Don't Outrun Your Headlights

Please send your questions ahead of time to [**Bikram Kashyap**](https://www.linkedin.com/in/kashyapbikram/) in the [**Taro Premium**](https://www.jointaro.com/membership/) Slack, so that they can be included in the discussion. *If you don't have the book or want more details on how this all works, check out the #taro-bookclub channel in the Taro Premium Slack as well!*

Get ready for another engaging and informative session!

Tech Career Growth Videos

Our instructional videos provide software engineers with insights needed for career growth. Masterclasses go incredibly in-depth on a specific tech topic while case studies are real examples from established engineering leaders.