Answer Box (TL;DR)
Philanthropy can rewire a life—both for the giver and the recipient. In this episode, Dan Pascone and Melanie Davis (VP, Marketing & Development, CityTeam) unpack how long-term recovery programs, living-wage job pathways, and modern giving vehicles (DAFs, appreciated stock, crypto) can maximize impact and tax efficiency—subject to eligibility and IRS rules.
Executives and founders learn how to align giving with outcomes that last, evaluate partners, and choose tax-smart ways to fund change while staying compliant.
Key Takeaways
- Impact first: Look for organizations delivering lasting outcomes (e.g., long-term sobriety, living-wage employment), not just temporary relief.
- Giving vehicles matter: Donor-advised funds (DAFs) can separate the tax event from the grant decision; appreciated stock and crypto may offer tax advantages under IRS rules. See Resources.
- Economic empowerment: Programs like CityTeam @ Work focus on certifications and job placement tied to living-wage targets—turning charity into durable stability.
- Generational engagement: Make it easy for younger donors to get hands-on while keeping accessible paths for seasoned givers (DAFs, stock gifts, planned giving).
- Governance & stewardship: Vet leadership, strategy, and financial stewardship to ensure each dollar is maximized.
Key Moments
- [00:02] Welcome & mission: why philanthropy matters to Tailored Wealth.
- [01:07] Guest intro: Melanie Davis, VP Marketing & Development, CityTeam.
- [03:00] “Hand up, not handout”: meeting immediate needs and designing lasting solutions.
- [03:59] Residential & transitional housing; weekly case management.
- [04:34] Living-wage goal & certifications (e.g., Google IT, unions) to boost earning power.
- [04:59] Tackling food insecurity; Elevate community outreach.
- [06:23] How programs are funded—individual philanthropists, foundations, corporations.
- [08:04] Why donors connect: transformation and trusted stewardship.
- [11:15] Donor development: aligning passions with specific partnership opportunities.
- [11:56] DAFs 101: timing the tax deduction vs. grants; underutilized by many earners.
- [13:14] Big-income years: front-load DAF funding; grant later for bigger impact.
- [14:01] Capital campaign example: 50-unit apartment complex for women & children.
- [15:20] The future: diversify engagement; even accepting crypto donations.
- [17:36] Lightning Round: habits, quotes, and personal hacks.
- [20:53] Melanie’s story: 14 years sober; full-circle leadership.
- [23:42] How to engage CityTeam; where to connect.
Episode Summary
In Episode #26 of Making Sense of Your Money, host Dan Pascone sits down with Melanie Davis, VP of Marketing & Development at CityTeam, to explore how thoughtful philanthropy fuels lasting change. CityTeam serves people overcoming addiction, homelessness, incarceration, and food insecurity, pairing immediate relief with long-term solutions. Residential and transitional housing are coupled with weekly case management and the CityTeam @ Work program, where certifications, coaching, and placement target living-wage jobs and enduring stability. Families experiencing food insecurity access groceries and on-ramps to skills training through Elevate.
On funding, Melanie details how individual philanthropists, foundations, and corporations underwrite free services for clients. Dan and Melanie discuss using donor-advised funds (DAFs) to separate tax timing from grantmaking, and how appreciated securities or even crypto (treated as property for tax purposes) can be efficient giving vehicles—subject to IRS rules and documentation. They also talk about the importance of evaluating stewardship, leadership, and measurable results. The conversation closes with a human moment: Melanie’s own transformation and why “hand up, not handout” is more than a slogan—it’s a blueprint for rewiring lives through generosity.
Transcript
(00:02) Dan: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life… Episode number 26 of the Making Sense of Your Money podcast.
(00:30) Dan: I’m your host, Dan Pasone… Today, we’ve got a really special and unique guest… Melanie Davis, VP of Marketing & Development at CityTeam… we’re going to talk all about philanthropy…
(01:07) Dan: …brief overview of who you are… and what your organization supports?
(01:33) Melanie: I oversee development and marketing at CityTeam… we help men and women overcoming substance abuse, homelessness, and food insecurity across five U.S. locations… services are free to recipients thanks to generous donors.
(02:29) Dan: …what you do is near and dear… take us through the day-to-day and what you help people accomplish.
(03:00) Melanie: We meet immediate needs, but our goal is lasting transformation… we meet people at their lowest—domestic violence, homelessness, incarceration, substance abuse… provide inspiration and resources for change.
(03:39) Melanie: We provide a hand up, not a handout… two main methods: residential/transitional housing with weekly case management and CityTeam @ Work for job skills training.
(04:16) Melanie: We target living-wage jobs… partner for certifications (e.g., Google IT, unions) to increase earning potential and economic empowerment.
(04:59) Melanie: Food programs address families’ tradeoffs; Elevate engages neighborhoods, connects families to training and income pathways.
(05:56) Dan: You’re driving lasting change… how do you fund the services?
(06:23) Melanie: Primarily individuals, also corporations and foundations… my team partners with donors who are passionate about impact and connects them to critical services.
(07:34) Dan: What makes donors connect with you?
(08:04) Melanie: Seeing transformation; trust in stewardship and strategy; CityTeam @ Work includes financial training to build multi-generational stability.
(10:34) Dan: Everyone wins when impact is sustained… how do donors engage and get developed?
(11:15) Melanie: We align partners to meaningful opportunities; many give via DAFs due to timing and tax benefits.
(12:30) Dan: DAFs are under-utilized… control timing of deductions, invest funds, grant later—especially useful in big-income years.
(14:01) Melanie: Example: capital campaign for a 50-unit apartment complex for women and children; DAF donors accelerated impact when it mattered.
(14:56) Dan: Where is philanthropy going?
(15:20) Melanie: Rapid change and technology; diversify ways to engage; offer entry points across generations; even accept cryptocurrency donations.
(17:36) Dan: Lightning round…
(20:53) Melanie: My connection to CityTeam is personal—I went through the residential program; 14 years sober; now raising funds for the program that helped me.
(23:42) Dan: How can listeners connect?
(23:42) Melanie: Visit cityteam.org; my info appears on legacy giving, stock donation, and DAF pages; email shared on those pages.
Resources & Citations
- CityTeam – Programs & Locations: cityteam.org; Programs overview; CityTeam @ Work; DAF page. [CityTeam details]
- IRS Publication 526 – Charitable Contributions (rules, AGI limits, documentation): IRS.gov/Pub526. [Cash vs. property, AGI limits]
- IRS Publication 526 (PDF): Download. [Current revision]
- IRS Notice 2014-21 – Virtual Currency Treated as Property: IRS Notice 2014-21. [Crypto donations treated as property]
FAQs
How can a donor-advised fund (DAF) make my giving more effective?
A DAF lets you take a charitable deduction in the year you contribute to the fund while granting to charities over time. It can simplify administration, support investment growth inside the DAF, and help you align giving with cash-flow or liquidity events—subject to eligibility, AGI limits, and substantiation rules in IRS Publication 526. [IRS Pub 526]
Is donating appreciated stock more tax-efficient than cash?
Often, yes. If you donate publicly traded shares held >12 months to a qualified charity or DAF, you may deduct fair market value and avoid capital gains tax you’d owe if you sold first—subject to AGI limits (commonly 30% for appreciated property) and documentation (Form 8283 when required). Coordinate with your advisor. [IRS Pub 526]
How are crypto gifts treated for tax purposes?
The IRS treats virtual currency as property, not cash. Donating appreciated crypto you’ve held >12 months may qualify for a fair-market-value deduction, with appraisal/substantiation rules similar to other non-cash property. Work with your custodian and charity in advance. [IRS Notice 2014-21] [IRS Pub 526]
Can I donate RSUs or company stock tied to my employer?
It depends. Shares generally must be vested and delivered into a brokerage account before transfer; blackout policies and insider rules may apply. Many charities and DAF sponsors accept publicly traded stock, but timing, basis, and holding period drive tax treatment. Coordinate with your plan administrator, tax advisor, and the receiving organization. [SOURCE NEEDED for employer-plan specifics]
What should I evaluate when choosing nonprofits to support?
Look for measurable outcomes (e.g., long-term recovery and living-wage placement), transparent financials, experienced leadership, and clear programs that build skills and stability. Review audited statements, program data, and alignment with your values. Pair giving with site visits or volunteer time to validate fit. [SOURCE NEEDED for a standardized framework]
Disclaimer
This content is for educational purposes only and is not tax, legal, or investment advice. Charitable strategies and deductions depend on your facts and are subject to IRS rules and sponsor/charity eligibility. Consult your professional advisors before acting.
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Next Steps (CTA)
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