How to Give Smarter This Season: Charitable Strategies Beyond Writing a Check
Giving is emotional. Planning makes it powerful.
For a lot of families, the holidays are when generosity becomes real: you see the need, you feel grateful, and you want to help.
Thats the best reason to give.
But if you’re a founder or executive with a complex financial life, there’s a second question worth asking:
How can I give in a way that supports the causes I care about and fits my broader wealth strategy?
Below are a few charitable strategies that can help you give more intentionallyoften with meaningful tax benefitswithout turning the holidays into a paperwork project.
Important note: charitable planning is highly personal and tax rules vary. Coordinate with your CPA and advisor before acting.
1) Donate appreciated assets (not cash)
If you have investments that have grown significantly, donating appreciated assets can be one of the most efficient ways to give.
Why it can be smart:
You may be able to deduct the fair market value (subject to IRS rules and limits)
You may avoid capital gains tax you’d otherwise owe if you sold the asset first
Who it’s best for: People with taxable brokerage accounts and concentrated winners.
2) Use a Donor-Advised Fund (DAF) to simplify giving
A DAF is often the bridgebetween wanting to give thoughtfully and not wanting to manage a mini foundation.
Why it can be smart:
You can potentially take a deduction in the year you contribute
You can distribute grants to charities over time
It creates a single hub for receipts, recordkeeping, and a giving plan
Holiday use case: You want to be generous this year, but you’re not sure which organizations you’ll support long-term.
3) Bunch your giving (instead of spreading it evenly every year)
If you alternate between itemizing and taking the standard deduction, your charitable gifts may not always create a tax benefit.
Bunching means concentrating multiple years of giving into one year then giving from that pool over time (often via a DAF).
Why it can be smart:
May increase the likelihood you itemize in the bunchedyear
Helps you keep your giving consistent even if your deductions aren’t
4) Align giving with liquidity (so you dont create stress later)
One of the most overlooked parts of charitable planning is cash flow.
A simple rule: Don’t let generosity create a tax or liquidity surprise.
What to consider:
Upcoming tax payments
Business cash needs (for founders)
Large purchases or known expenses in Q1
Giving feels best when it’s confidentnot when it’s followed by,Wait, did I overdo it?
5) Give with intention: build a giving thesis
High performers don’t wing their investing. They also don’t have to wing their giving.
A simple giving thesis answers:
What causes matter most to us?
What outcomes do we want to support?
What’s our annual giving budget?
Do we want to involve our kids or extended family?
This turns giving from randominto repeatableand often becomes part of family legacy.
A quick give smarterchecklist
Before you write a check, ask:
Do I plan to itemize this year?
Do I have appreciated assets I could donate instead?
Would a DAF simplify our giving and recordkeeping?
Do we have a giving budget that won’t create liquidity stress?
Do we want to turn this into a family conversation (values, legacy, impact)?
The takeaway
Writing a check is generous. But for many founders and executives, it’s not the most strategic way to give.
With a little planning, you can:
Potentially increase the impact of each dollar
Simplify your giving process
Align generosity with your broader wealth strategy
If you want, we can help you coordinate a simple giving plan with your CPA and your overall wealth strategyso your year-end generosity is both meaningful and efficient.
Check us out at www.forecastcapitalmanagement.com.
