• Understanding Share Types: Preferred vs Common Shares

    Understanding Share Types: Preferred vs Common Shares

    Founders must understand share types: preferred and common shares. Preferred shares appeal to investors due to higher claims on assets and dividends, but lack voting rights. Common shares offer ownership and voting power but are riskier. Structuring shares depends on business goals and investor attraction while rewarding employees and sustaining founder control.

  • In Case You Missed It: Best of Summer 2024

    In Case You Missed It: Best of Summer 2024

    The article highlights the five most popular newsletter topics as summer ends, focusing on employee benefits, retirement planning, job searching, remote work culture, and the use of AI for lead research. These insights aim to help readers enhance their professional and personal lives, with more content expected in the fall.

  • To 83(b) or Not to 83(b), that is the Tax Question: A Brief Guide

    To 83(b) or Not to 83(b), that is the Tax Question: A Brief Guide

    Founders and early employees in startups must decide whether to file an 83(b) election for equity compensation, impacting future tax liability. This election allows prepaid taxes at grant, potentially leading to savings if the company’s value increases. It’s crucial to consult a tax advisor, considering risks and financial situations within the 30-day window.

  • ETFs vs. Mutual Funds: Understanding the Key Differences

    ETFs vs. Mutual Funds: Understanding the Key Differences

    Exchange-traded funds (ETFs) and mutual funds are popular investment choices for achieving financial goals. Both offer diversification and professional management, with key differences in trading, fees, transparency, tax efficiency, and minimum investment. Choosing between them depends on individual circumstances, preferences, and investment goals. ETFs may be suitable for lower costs and tax efficiency, while mutual…

  • What’s a “Boglehead” & More about Passive Investing

    What’s a “Boglehead” & More about Passive Investing

    In recent times, small-cap stocks have surged, highlighting the short-term unpredictability of the market. Embracing the Boglehead philosophy, based on John Bogle’s principles, advocates passive investing through low-cost index funds. This approach prioritizes long-term growth over quick gains, emphasizing simplicity, low expenses, and steadfastness in navigating market fluctuations.

  • Beyond Roth: Comparisons to a Traditional IRA & Backdoor Conversions

    Beyond Roth: Comparisons to a Traditional IRA & Backdoor Conversions

    The Roth IRA offers tax-free retirement savings, while the Traditional IRA allows tax-deductible contributions and tax-deferred growth. The choice between them depends on factors like current and future tax rates. For high earners, the “Backdoor Roth” conversion strategy can provide tax-free retirement income, but careful consideration and professional advice are crucial.

  • In Case You Missed It: 4th of July Best Hits Edition

    In Case You Missed It: 4th of July Best Hits Edition

    As we prepare for the 4th of July, we’re highlighting our top 5 newsletter articles covering business operations and personal life tips. Explore topics like dealing with sales taxes, project management tools, Health Savings Accounts, personal mentorship, and handling adverse business prospects. Enjoy the holiday and we’ll be back next week.

  • Roth IRA: Your Retirement Cornerstone

    Roth IRA: Your Retirement Cornerstone

    Roth IRAs offer tax-free growth and withdrawals, flexibility, and long-term retirement accumulation. Contributions are made with after-tax dollars, allowing for tax-free growth and withdrawals. Early-career starters benefit from locking in lower tax rates. Other advantages include flexibility, no required minimum distributions, and protection against future tax increases. Eligibility and contribution guidelines apply, and various strategies…

  • Why I Chose to Own

    Why I Chose to Own

    After a decade of renting in New York City, my wife and I decided to move to New England, where we found our dream home. We saved diligently for a down payment and sought opportunities in more affordable areas. Our decision to buy was driven by family planning, financial sensibility, independence, and the desire for…

  • HSA Pt. 2 – Know your options & how to optimize

    Missed Part 1 on HSAs? Check it out here on Substack. You’ve opened your HSA, funded it, and are ready to manage those medical bills. Now comes the question – how to optimize your HSA for maximum benefit. Let’s dive into contribution limits, saving strategies, investment options, and explore similar accounts like FSAs and HRAs. Contribution Limits: How Much Can…