logo
episode-header-image
Jul 28
7m 15s

305: How to Reduce Taxes on IPO Wealth (...

Hilary Hendershott, CFP
About this episode
If you’re holding startup equity and expecting a liquidity event, here’s what most people don’t realize: The biggest tax decisions are made before your equity becomes liquid. I walk through the most common tax mistakes I see with IPOs and startup equity — and what high-income professionals can do to create more flexibility and control. You’ll learn: Why IPOs ... Show More
Up next
Aug 18
308: Am I Financially Stable? Signs You’re Doing Ok (Even If It Doesn’t Feel Like It)
On paper, everything looks good.You’re earning more. You’re saving. You’re investing.So why doesn’t it feel settled?In this episode, I walk through the subtle but powerful signs that your financial life is actually on track — even if it doesn’t feel that way yet.Because at higher ... Show More
7m 48s
Aug 11
307: How to Reduce Taxes on Company Stock (For Women in Tech)
If you’re a high-income woman in tech and your company stock has grown into a large portion of your net worth, you may be facing a difficult reality:Diversifying feels smart… but the tax bill feels overwhelming.In this episode, I walk through why this happens — and how tax-aware ... Show More
8m 37s
Aug 4
306: Should You Pay Off Your Mortgage Early — Or Invest Instead?
Many homeowners locked in historically low mortgage rates over the last several years — often well below long-term expected market returns.So a common question comes up:Should you pay off your mortgage early, or invest that money instead?Why low mortgage rates change the mathHow ... Show More
8m 26s
Recommended Episodes
Aug 2022
Manifesting Wealth
This week, we’re sharing an episode of Brown Ambition, a podcast hosted by Mandi Woodruff (who you may remember from our episode “Negotiating Your Way to Success”) and Tiffany "The Budgetnista" Aliche. In this episode, Mandi and Tiffany answer your hard-hitting questions like how ... Show More
25m 37s
Mar 2023
394: Ask the Money Experts: Backdoor Roths, Bad Debt, & When to Fire Your Financial Advisor
Retirement investing, bad debt, backdoor Roth IRAs, bonds, and starting a business. If you’re just beginning your personal finance journey, this can all seem a bit complicated. Where do you invest first? What should you do with extra cash? And how do you know a financial fiduciar ... Show More
50m 13s
Jun 2022
TIP456: How to Build a Wealth Plan for Financial Independence w/ Katie Gatti
IN THIS EPISODE, YOU'LL LEARN: 14:38 - How to calculate your retirement needs. 20:32 - How to determine how much cash you should reserve. 39:46 - How to think through investment account types like 401ks, IRA’s, Roths, etc. 51:17 - The ideal allocation of index funds. 1:00:34 - Wh ... Show More
1h 9m
Aug 2025
Money Diaries, Career Breaks, and Owning Your Financial Story with Lindsey Stanberry
This week, Sim sits down with Lindsey, the creator of the cult-favorite Money Diaries, to uncover the fascinating truths behind how women really spend and talk about money. They explore why financial transparency is still taboo, how values shape spending, and what it takes to con ... Show More
35m 18s
May 2024
S2E36: How to Invest in 2024
In this episode of the Rich Dad Stockcast, guest host Andy Tanner interviews Corey Halliday, the chief risk manager at the Cashflow Academy, about the intriguing dynamics of stock and options trading, especially in a volatile economic landscape. Tanner and Halliday dive into the ... Show More
32m 45s