Resource Center

Guides and insights to simplify taxes, equity, and planning.

Webinars

Understanding RSUs: How They're Taxed — and How to Keep More of What You Earn

June 27, 2025

Laura Moreno — Co-founder, Chief Tax Officer @ Fifteenth

Jason Hoffman — Tax Advisor @ Fifteenth

Restricted Stock Units (RSUs) are a significant component of compensation in the tech industry, yet many professionals find their tax implications confusing. This often leads to unexpected tax bills and missed opportunities for tax savings

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Past webinar
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Tender Offers & Personal Taxes: How to Avoid Costly Mistakes

April 25, 2025

Laura Moreno — Co-founder, Chief Tax Officer @ Fifteenth

Jason Hoffman — Tax Advisor @ Fifteenth

Recently participated in a Tender Offer? Liquidity events like these can be exciting — but the tax implications are often complex, and a misstep could mean leaving money on the table.

Join Laura Moreno, Chief Tax Officer, and Jason Hoffman, Equity Tax Advisor, as they share practical strategies to help you keep more of what you’ve earned.

Past webinar
Past webinar
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How to Minimize Stock Option Taxes: Planning Advice for ISO & NSO Shares

March 14, 2025

Laura Moreno — Co-founder, Chief Tax Officer @ Fifteenth

Jason Hoffman — Tax Advisor @ Fifteenth

Work at a private company and have ISOs or NSOs? Are you aware of the tax implications when exercising or selling your shares?  Equity compensation can be life-changing — if you manage it wisely. Don’t make the mistake of exercising or selling shares without considering taxes.

Join Fifteenth’s tax team, Laura Moreno, Chief Tax Officer and Jason Hoffman, Equity Tax Advisor, to learn how to maximize what you keep with your equity transactions.

Past webinar
Past webinar
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Guides

The Deductions You're Probably Missing: A Guide to Rental and Self-Employment Tax Savings

October 27, 2025

Jim Carroll - Senior Tax Advisor at Fifteenth

If you have a rental property or side consulting gig, you're likely leaving money on the table every year. Not because you're doing anything wrong — but because you're not tracking the right expenses.

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Interest Tracing: The Hidden Tax Trap That Could Cost Startup Founders Millions

September 29, 2025

Jim Carroll - Senior Tax Advisor at Fifteenth

If you're a startup founder or early employee who's borrowed money to exercise options or invest in your company, you need to know about interest tracing. This obscure tax rule could turn what you thought was deductible interest into a costly mistake — and most people don't even know it exists

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The SMLLC to S-Corp Conversion: When It Actually Makes Sense (And When It Doesn't)

September 18, 2025

Jim Carroll - Senior Tax Advisor at Fifteenth

The internet is flooded with advice about converting your single-member LLC (SMLLC) to an S-corp election. Much of it is wrong.

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QSBS Just Got a Massive Upgrade: The Game-Changing Rules You Need to Know

July 25, 2025
Decoding the "One Big Beautiful Bill" Series

Jim Carroll - Senior Tax Advisor at Fifteenth

The "One Big Beautiful Bill" just made the already powerful QSBS tax break even better. Here's what startup founders, early employees, and investors need to know about the new rules.

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The 0% Tax Rule You’ve (Probably) Never Heard Of: A Beginner’s Guide to QSBS

Laura Moreno — Co-founder, Chief Tax Officer at Fifteenth

If you’ve worked at, invested in, or founded a startup, you might be eligible for one of the most powerful — and least understood — tax breaks out there: Qualified Small Business Stock (QSBS).

It can mean paying zero capital gains tax when you sell your shares. But most people don’t realize they qualify — or lose the benefit by accident.

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Preparing for Tax Payments with RSUs

Laura Moreno — Co-founder, Chief Tax Officer at Fifteenth

Receiving Restricted Stock Units (RSUs) can be an exciting part of your compensation package—but it also comes with important tax responsibilities. Many people are caught off guard by unexpected tax bills, especially when they don’t fully understand how RSUs work. This guide will walk you through the key things to know, in plain language, so you can plan ahead and avoid surprises.

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