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The 2025 Guide to Paying Less in Taxes

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Personal Finance for Startup Founders

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Ankur Nagpal
Ankur NagpalFounder of Carry - grow your net worth by being smart about taxes. Previously founded Teachable and investor in 100+ startup at Vibe Capital.
USVC is now available on SoFi

USVC is now available on SoFi

which means USVC is available via IRA for the first time today!

Aug 5, 2026
Introducing: The Outliers Summit

Introducing: The Outliers Summit

I’m excited to share something I’ve been working on quietly for the last year

Aug 3, 2026
How to Invest in Startups From Your Roth IRA

How to Invest in Startups From Your Roth IRA

How to hold startup investments in one of the most tax-advantaged accounts in the US

Jul 17, 2026
Introducing: USVC Select

Introducing: USVC Select

The new way to invest in individual startups with zero carry

Jun 26, 2026
The SpaceX IPO

The SpaceX IPO

Where most of the money actually got made (spoiler alert: not where most could reach it)

Jun 8, 2026
Introducing: USVC

Introducing: USVC

Today, I’m excited to announce something I've been quietly working toward for a while...

Apr 22, 2026
Your Tax Return Isn't Going to File Itself

Your Tax Return Isn't Going to File Itself

It’s that time of the year again, and if you haven’t filed your personal returns yet, here’s the cleanest path through it.

Apr 12, 2026
The High Earners Guide to a 529 Plan

The High Earners Guide to a 529 Plan

Most people are using their 529 plan wrong. Here's how to fix that.

Mar 18, 2026
How to Access Your Retirement Dollars Before Retirement

How to Access Your Retirement Dollars Before Retirement

Before you assume your retirement savings are untouchable, read this...

Mar 11, 2026
6 Things You Can Still Do To Save On Your 2025 Tax Bill

6 Things You Can Still Do To Save On Your 2025 Tax Bill

The six biggest tax opportunities for business owners and the deadlines you can't afford to miss.

Mar 4, 2026
How to Pay Less on Your 2025 Taxes

How to Pay Less on Your 2025 Taxes

Whether you're an employee, freelancer, founder, or digital nomad, this is what you need to know before April 15.

Feb 25, 2026
The Complete Tax Guide for US Expats and Digital Nomads

The Complete Tax Guide for US Expats and Digital Nomads

If you're a US citizen living abroad, this tax guide could change how much of your income you actually keep

Feb 18, 2026
How My Friend Saves $6,000 a Year Working From Home

How My Friend Saves $6,000 a Year Working From Home

If you work for yourself, your home office can be worth thousands of dollars in tax deductions

Feb 11, 2026
My Complete Guide to S-Corporations

My Complete Guide to S-Corporations

Save (potentially) thousands of dollars in taxes with this election before March 15th

Feb 4, 2026
10 Big Tax Changes in 2026 (And What You Should Do About Them)

10 Big Tax Changes in 2026 (And What You Should Do About Them)

#7 can be catastrophic if you don't watch out!

Jan 28, 2026
How to Use Your HSA as a Wealth Building Machine

How to Use Your HSA as a Wealth Building Machine

Learn why an HSA is the most tax-advantaged account in America and how to use it to its full potential

Jan 21, 2026
How to Borrow Money at US Treasury Rates

How to Borrow Money at US Treasury Rates

How wealthy people borrow millions of dollars almost as cheaply as the US government

Jan 14, 2026
The $1,500 IRS Credit Most People Miss

The $1,500 IRS Credit Most People Miss

How a little-known tax credit can reduce your tax bill by up to $1,500

Dec 29, 2025
The Tax-Efficient Guide to Charitable Giving

The Tax-Efficient Guide to Charitable Giving

How wealthy people use charitable contributions to save massively on their taxes

Dec 24, 2025
My Complete Guide to Tax-Loss Harvesting

My Complete Guide to Tax-Loss Harvesting

Follow this playbook before the end of the year to potentially pay no capital gains taxes

Dec 9, 2025
Introducing: The Advanced Tax Strategy Masterclass for High Earners

Introducing: The Advanced Tax Strategy Masterclass for High Earners

I’m excited to share something I’ve been working on quietly for six months

Nov 18, 2025
Your Year-End Tax Saving Checklist (expires December 31)

Your Year-End Tax Saving Checklist (expires December 31)

The most important tax deadline of the year is almost here - are you ready?

Nov 17, 2025
3 Tax Strategies I Used to Save 6-Figures This Year

3 Tax Strategies I Used to Save 6-Figures This Year

Three tax saving moves I personally employed this year to knock $100,000+ from my taxes

Oct 30, 2025
How Business Owners in California and New York Pay Less in Taxes (The PTET Workaround)

How Business Owners in California and New York Pay Less in Taxes (The PTET Workaround)

If you live in a high tax state, you can pay your state taxes through your business and save tens of thousands in taxes

Oct 16, 2025
The Top Secret Retirement Plan for High Earners

The Top Secret Retirement Plan for High Earners

The most exclusive retirement plan in America that you can use for a 6 figure tax deduction

Oct 2, 2025
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Silly Money™ is an educational media subsidiary. Educational content only - not personalized advice. Our editorial team operates independently, though our coverage may reflect our familiarity with affiliated companies. We may receive compensation from services mentioned. No advisory or client relationship created. Questions? [email protected]