Nov 3, 2026 · 29 min
Raul Shah links stock conviction to charitable tax strategy
3 high conviction stocks + charitable giving: tax alpha with Raul Shah
The episode connects volatile equity selection with practical rules for turning charitable giving into a more effective tax-planning tool.
- 1Raul Shah presents Hims & Hers Health, ServiceNow, and UnitedHealth as value-investing opportunities with different growth and volatility profiles.
- 2Donor-advised funds can bunch multiple years of giving into one contribution year while allowing grants to charities later.
- 3Deduction limits vary by asset type, so large contributions may not produce an immediate deduction for their full value.
Don't miss
Raul Shah explains how donor-advised funds can bunch multiple years of charitable giving into one contribution year, subject to deduction limits.
The brief
Raul Shah discusses his value-investing approach and highlights Hims & Hers Health, ServiceNow, and UnitedHealth while market volatility complicates the case for conviction.
The conversation shifts from stock selection to tax planning, framing charitable giving as a strategy rather than merely an annual act of generosity.
Shah explains how donor-advised funds let contributors give cash, securities, crypto, or other eligible assets now and recommend grants later.
The central tax insight is deduction bunching: consolidating several years of donations into one tax year can matter when smaller gifts produce little benefit.
The episode closes with the caveat that deduction limits depend on the asset contributed, meaning a large gift may not be fully deductible immediately.
What was said on this episode
36 statements · 25 positive · 4 negative · 7 neutral
Buying companies below estimated value increases investment safety.
“the bigger the discount that you can buy, the safer the investment”
Listen at 1:57
Value stocks are the antidote to volatile markets.
“the antidote to volatile markets has always been the same. It's buying value stocks, really good companies at cheap prices.”
Listen at 3:00
Hims & Hers is expected to grow more than 30% for the foreseeable future.
“they're expected to continue to grow you know 30 plus for the foreseeable future”
Listen at 3:48
Hims & Hers’ subscription revenue is highly predictable.
“the revenue is very predictable”
Listen at 4:26
AI is already replacing single-function CRM software capabilities.
“AI is going to take that job pretty easily. In fact, it's already doing that.”
Listen at 7:20
AI enhances ServiceNow's platform offering.
“when you're an actual platform, like what I call a pass, AI enhances platform as a service. AI enhances. offering. And that's what service now does.”
Listen at 7:23
AI enhances ServiceNow’s platform offering.
“AI enhances platform as a service. AI enhances. offering. And that's what service now does.”
Listen at 7:26
Volatile markets create opportunities for strong long-term investments.
“there are opportunities in volatile markets to make tremendous long-term investments”
Listen at 9:09
UnitedHealth Group’s margins will recover after plan repricing.
“they just have to reprice their plans and their margins will come back over a couple of years.”
Listen at 9:28
Hims & Hers will become profitable quickly and reach high profitability.
“That's going to be profitable very quickly and extremely profitable.”
Listen at 10:21
Hims & Hers short sellers will suffer severe losses.
“They're dead wrong and they're going to get murdered.”
Listen at 11:17
Investors cannot develop conviction without conducting their own research.
“you can never gain conviction unless you do the research yourself”
Listen at 11:49
DAFs and QCDs enable charitable giving while providing tax benefits.
“what both of these are, are two tax strategies that will allow you to give to charities that you want to support. but actually claim a tax benefit from doing so.”
Listen at 14:25
Charitable contributions are deductible only when taxpayers itemize deductions.
“if you get to charity, you could deduct that, but you have to itemize your deductions.”
Listen at 15:33
Taxpayers can itemize when deductions exceed the standard deduction.
“if you collectively add them up and it exceeds your standard deduction of $32,200, then you can itemize”
Listen at 15:50
Contributing $50,000 to a donor-advised fund can enable an itemized deduction.
“you put $50,000 in a donor advised fund. Well, now you could itemize your deduction because $50,000 now you can deduct.”
Listen at 17:03
Bunching donations in a DAF creates a large deduction in the contribution year.
“you get a huge tax benefit. in the year that you contribute.”
Listen at 17:11
A QCD transfers IRA funds directly to a nonprofit tax-free.
“it's just a tax-free transfer from your IRA straight to a nonprofit.”
Listen at 17:44
QCD eligibility is limited to IRA owners aged 70½ or older.
“it's only for IRA owners who are 70 and a half or older”
Listen at 18:46
Qualified charitable distributions have an annual limit of $111,000 per person.
“there's an annual limit of $111,000 per person.”
Listen at 19:02
QCDs have an annual limit of $111,000 per person.
“there's an annual limit of $111,000 per person”
Listen at 19:02
QCDs count toward required minimum distributions.
“the QCD counts towards your RMD or your required minimum distribution”
Listen at 19:16
Donor-advised funds allow multiple years of giving to be deducted in one tax year.
“the donor advised fund lets you pile multiple years of giving into one single tax year to get a huge deduction”
Listen at 20:07
A $25,000 stock contribution to a donor-advised fund can produce an immediate $25,000 deduction.
“she could put potentially $25,000 of stock into the donor advised fund today. And she would get an immediate tax deduction of $25,000.”
Listen at 20:34
QCDs satisfy RMDs without increasing the recipient’s taxable income.
“it still counts towards your RMD, but it never shows up as taxable income for you”
Listen at 21:34
The IRS prohibits routing IRA QCDs into donor-advised funds.
“you can't do that. The IRS bans it.”
Listen at 22:36
QCDs are generally better than donor-advised funds because they offset income tax.
“QCDs technically are better than donor advised funds because QCD, what they're doing is they're offsetting income tax.”
Listen at 22:42
Cash DAF contributions are deductible up to 60% of adjusted gross income.
“If you put cash in the donor advised fund, so like you just put $50,000 in cash, you're limited in how much you can deduct in that year. It's 60% of your adjusted gross income.”
Listen at 23:34
Stock DAF contributions are deductible up to 30% of adjusted gross income.
“If you put stock in the account in the donor advised fund, you're actually limited to 30% of your adjusted gross income”
Listen at 23:46
Unused donor-advised-fund deductions carry forward for five years.
“everything else above that carries forward for five years”
Listen at 23:56
Donating appreciated stock to a donor-advised fund eliminates the stock's capital gain.
“if you're donating appreciated stock, you actually get a tax break because that stock, the capital gain, gets wiped out when you give it to the donor advised fund.”
Listen at 24:46
Donating appreciated stock to a DAF provides a deduction and eliminates capital gains tax.
“you also get to wipe out the capital gains tax. So there's actually a double tax benefit if you donate stock versus if you donate cash.”
Listen at 25:01
QCDs should be executed before cash IRA distributions to preserve tax treatment.
“you always want to make sure that you execute the QCD before taking any cash distributions”
Listen at 25:41
Taxpayers should use a professional to plan charitable-giving tax strategies.
“make sure you have a professional to help you map out the numbers because you don't want to screw this up and get into problems.”
Listen at 26:17
Tax savings should not be the sole reason for choosing charitable causes.
“you don't want to just give to charities, maybe for causes that you don't necessarily believe in or have conviction in because you're trying to save money in taxes”
Listen at 27:11
Donors should choose causes first, then apply tax strategies if advantageous.
“Find those charities and those causes. that you really care about, that you really want to support. And then if you can find a way to make it advantageous for you from a tax planning perspective using one of these two strategies, then you go forward and do it.”
Listen at 27:22
Statements are attributed to the speaker as said on the episode and reflect their view at the time, not PodLume's. They are not advice.
Weekly email
State of the Pod, every Monday
The week's most-discussed names and stories from podcasts, with the moments behind them. Free, five minutes, unsubscribe in one click.