How Philanthropy Rewires a Life | Dan Pascone with Melanie Davis | Podcast #26

Posted on July 14, 2025 by Dan Pascone

Episode TL;DR

In this episode: Dan talks with Melanie, VP of Marketing and Development at CityTeam, a faith-based nonprofit serving people facing homelessness, addiction, incarceration, and food insecurity. They unpack how CityTeam pairs immediate help (housing, meals, groceries) with long-term transformation (sobriety, job skills, financial education), why their sobriety outcomes are so strong, and how donors can use tools like donor-advised funds and other creative giving vehicles to meaningfully support life-changing work. Melanie also shares her own powerful story of going through CityTeam’s recovery program, getting sober, and now raising funds for the same organization that helped save her life.

Who this is for: High-earning professionals and business leaders who want their giving to create real, lasting impact; anyone curious how philanthropic dollars actually get used “on the ground”; and people interested in combining smart tax planning (e.g., donor-advised funds, stock gifts) with purpose-driven generosity.

Key Takeaways

CityTeam focuses on both immediate needs and long-term change. They provide shelter, transitional housing, meals, and groceries, but the end goal is lasting transformation in areas like sobriety, employment, and financial stability.
Residential and transitional programs are intensive and long-term. Men and women can live on-site, work with case managers, and participate in CityTeam at Work – a job skills and career program geared toward living-wage employment, not just minimum-wage jobs.
Economic empowerment is central. CityTeam partners with organizations (e.g., IT certificates, unions, other training partners) so graduates can realistically earn a living wage (Dan mentions ~$26/hour as a benchmark in Santa Clara County) – especially critical for single parents and those rebuilding for their families.
Food programs are a key entry point. For families facing food insecurity, groceries open the door to deeper support like Elevate – neighborhood-based programs that combine food with job skills, financial education, and other resources.
CityTeam’s sobriety outcomes are unusually strong. While many short-term programs see long-term sobriety rates under 20%, CityTeam’s 10-month residential model reports sobriety success around the 70% range one year after graduation – nearly two years of sobriety from intake.
Financial literacy is part of the transformation. Many clients grow up with financial scarcity, fear, or simply no education around money. CityTeam explicitly teaches budgeting, financial stewardship, and money skills to break that cycle for both clients and their children.
Donors want impact and stewardship. Philanthropists care not only that lives are being changed, but that leaders have strong business and financial skills. CityTeam’s president brings a finance executive background (from Seagate), which helps donors trust that their dollars are well-managed.
Donor-advised funds (DAFs) are a powerful giving tool. Many of CityTeam’s supporters use DAFs to get immediate tax benefits when funding the DAF, then deploy grants to causes over time (for example, during a capital campaign to buy housing for women and children fleeing domestic violence).
Giving options are evolving fast. CityTeam is adapting to new donor preferences and technologies – from multiple ways to give, to generational engagement differences, to accepting cryptocurrency donations.
Melanie is “full circle.” She went through CityTeam’s program herself, overcame substance abuse, has over 14 years of sobriety, and now leads development and marketing to help others access the same life-changing support.

Key Moments

00:02 – Dan opens the episode and reaffirms the mission of helping business leaders make smart, confident money decisions.
00:30 – Introduction of episode 26 and guest Melanie, VP of Marketing and Development at CityTeam.
01:07 – Melanie shares what CityTeam does: helping people facing homelessness, substance abuse, incarceration, and food insecurity via five locations (three in California, one in Portland, one in Chester, PA).
03:00 – “Hand up, not handout”: how CityTeam meets people at their lowest (streets, encampments, domestic violence, jail) and focuses on lasting transformation.
03:59 – Overview of CityTeam’s two main approaches: residential/transitional housing and food-based programs.
04:16 – CityTeam at Work: job skills training focused on helping clients earn a living wage, including certifications (e.g., IT, union pathways) to increase earning potential.
04:59 – Food insecurity: how groceries relieve immediate pressure for struggling families while opening the door to programs like Elevate for longer-term economic empowerment.
06:23 – How CityTeam is funded: primarily through individual donors (philanthropists of all levels), plus corporate and foundation support.
07:34 – Why donors connect: high sobriety success rates, faith-based component, and strong financial stewardship from leadership with corporate finance backgrounds.
09:31 – The importance of financial training for clients coming from financial ignorance, scarcity, or fear – and the ripple effect on their children.
11:29 – How Melanie and her team work with donors and introduce different giving vehicles, especially donor-advised funds (DAFs).
12:30 – Dan’s mini “pitch” for donor-advised funds: timing tax deductions, investing the DAF, and giving strategically over time.
14:01 – Capital campaign story: acquiring a 50-unit apartment complex during COVID for women and children, supported heavily by donors using their DAFs.
14:56 – Melanie’s view on the future of philanthropy: rapid change, digital marketing, and the need to diversify ways people can engage and give.
15:48 – Accepting cryptocurrency, generational differences in engagement, and making entry points accessible for different donors.
17:36 – Lightning round begins: coffee vs. tea, French fries for life, and music as essential “tech.”
19:05 – Favorite principle: be generous with what you have today – not waiting until later to contribute.
19:58 – Habit stacking as her personal hack (pairing calls with driving, overlapping tasks to save time).
20:53 – Melanie shares her own story: going through CityTeam’s residential program, overcoming substance abuse, now 14+ years sober, and raising funds for the same program.
21:53 – Current milestone: seeking better “seasonal” balance across work, church, volunteering, and family.
22:36 – Advice to her younger self: early financial education matters; she wishes she’d learned money skills younger instead of starting from scratch as an adult.
23:42 – How to connect with Melanie and CityTeam; Dan closes with a reminder to prioritize your version of a rich life.

Episode Summary

In this episode of Making Sense of Your Money, Dan is joined by Melanie, who leads marketing and development at CityTeam, a nonprofit dedicated to helping people break cycles of addiction, homelessness, incarceration, and food insecurity. CityTeam operates across multiple U.S. cities and focuses on more than short-term relief: their guiding philosophy is to offer a “hand up, not a handout.”

Melanie explains that many clients arrive at their lowest moments—leaving abusive relationships, living in encampments or on the streets, or exiting jail with nowhere to go. CityTeam’s residential and transitional housing programs offer safe, stable environments where clients work with case managers, participate in CityTeam at Work for job skills training, and build a realistic path to a living-wage career. On the food side, CityTeam supports families who are deciding between paying bills and feeding their kids, providing groceries while also inviting them into programs like Elevate that focus on long-term economic empowerment.

A key point of pride: CityTeam’s outcomes. While many short-term recovery programs see sobriety rates below 20% after completion, CityTeam’s 10-month program reports sobriety rates around 70% one year post-graduation. That’s nearly two years of sobriety from intake. They also intentionally teach financial literacy, recognizing that many clients grew up with financial scarcity, fear, or zero money education. By teaching budgeting and money management, CityTeam aims to break generational patterns for both clients and their children.

The conversation then turns to philanthropy and how this work gets funded. CityTeam relies heavily on individual philanthropists, plus corporate and foundation support. Donors are drawn not only to the mission but to the strong stewardship behind it — their president comes from a corporate finance executive background, which gives donors confidence that every dollar is being managed strategically. Melanie highlights donor-advised funds (DAFs) as a powerful tool many of their supporters use: donors can receive tax benefits when contributing to the DAF, invest those funds, and then deploy gifts to organizations like CityTeam when meaningful opportunities arise, such as a capital campaign to buy an apartment complex for women and children fleeing domestic violence.

Looking ahead, Melanie sees the philanthropic sector undergoing rapid change: new channels for digital outreach, more competition for attention, and very different expectations across generations. CityTeam is working to diversify engagement methods—accepting cryptocurrency donations, structuring different volunteer and giving opportunities for retirees versus young families, and making sure there is a role for anyone who wants to help.

In a powerful personal moment, Melanie shares that she herself went through CityTeam’s residential program, overcame substance abuse, and has been sober for over 14 years. Her “bucket list” achievement is now serving in a position where she can raise funds and support the same program that helped transform her life. She closes the lightning round by emphasizing the importance of generosity with what you have today, cultivating good habits (including “habit stacking”), and encouraging her younger self—and listeners—to prioritize financial education early.

Full Episode Transcript

Transcript edited lightly for clarity and flow.

Narrator: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life.

Dan: Welcome to another edition of the Making Sense of Your Money podcast, where we cut through the financial noise and help business leaders make smart, confident money decisions.

Dan: This is episode number 26 of the Making Sense of Your Money podcast. I’m your host, Dan. I’m the founder and CEO of Tailored Wealth. Each episode features a trusted voice in the financial world—someone who works with high-level professionals to simplify the complex and turn strategy into action.

Dan: Today we’ve got a really special and unique guest. I’m excited about this one. We’ve got Melanie, VP of Marketing and Development at a great philanthropic organization called CityTeam. We’re going to talk about philanthropy, CityTeam’s mission, and how she works with professionals who help support that work. This is near and dear to my heart.

Dan: Melanie, thanks for joining the Making Sense of Your Money podcast. Good to have you.

Melanie: Dan, thank you so much for having me. I’m excited about our conversation.

Dan: Likewise. Let’s start with a quick overview. Who are you, what do you do, how did you get into this, and what does CityTeam support?

Melanie: Sure. I oversee the development and marketing team for CityTeam. CityTeam is a nonprofit that helps men and women overcoming substance abuse, homelessness, and food insecurity. We have five locations in the U.S.—three in California, one in Portland, Oregon, and one in Chester, Pennsylvania.

Melanie: I have the privilege of working with the team that engages our donors and partners to fund all of these programs. One of the things that makes CityTeam special is that our services are free to the people who need them, which is only possible because of generous contributions from individual philanthropists, corporations, and foundations.

Dan: Love that. You and I talked earlier—I’m involved with an organization that’s very similar in spirit, so what you do is close to my heart.

Dan: Give the audience a feel for what you do on the ground. Walk us through the day-to-day of the people you serve and what you help them accomplish.

Melanie: At CityTeam, we say we meet immediate needs, but our goal is lasting solutions and transformation. We often meet people at their lowest point—maybe they’re escaping domestic violence, living on the streets or in encampments, coming out of shelters, or getting ready to exit incarceration without a plan.

Melanie: Many of the people we serve are struggling with substance abuse. A lot of them are parents, and their kids have been impacted by their decisions. CityTeam steps in to inspire hope and provide resources people need to change the trajectory of their lives.

Melanie: We use the phrase “a hand up, not a handout.” Our services are free, but breaking through these challenges requires real hard work. We’re looking for people who are serious about change, and we commit to walking alongside them.

Melanie: We do this in two main ways. First, through residential and transitional housing. People can come live with us—how long depends on what they’re working through. Each person works with a case manager who meets with them weekly to identify barriers and build a plan. We also connect them to CityTeam at Work, which is our job skills training program.

Melanie: Our goal is to help people get jobs paying a living wage. On the West Coast, in places like Santa Clara County, that’s around $26 an hour for a single individual. We serve single moms with multiple kids, men getting sober who want to support their families—minimum wage isn’t enough.

Melanie: So we partner with organizations to provide certifications—like Google IT, union pathways, and other training—to increase their earning potential and build true economic empowerment.

Melanie: Second, we focus on food. Many families are food insecure and forced to choose between paying bills and putting food on the table. We step in with groceries to relieve that pressure.

Melanie: But again, the groceries are just the first step. We also run Elevate in neighborhoods and communities, working with families who come for food and then offering job skills, coaching, and other resources to help them grow their earning power.

Dan: That’s a great breakdown. I love “a hand up, not a handout.” My big takeaway is you’re not just providing temporary solutions—you’re driving long-term, generational change. That benefits not only the individuals but also their families and the broader community.

Dan: Let’s talk about how you’re able to provide these services. The work is amazing, but it has to be funded. Give us a look under the hood at how you make this sustainable.

Melanie: CityTeam works primarily with individual donors to fund our services. As I mentioned, everything is free for our clients. That’s made possible through philanthropists who invest in people they may never meet directly—so that when the next person needs help, the door is open.

Melanie: We also work with corporations and foundations, but we’re especially fortunate to have individual donors at all levels. Some give modest amounts; others are high-capacity donors very passionate about using their resources to help others. My team works closely with donors who want to be intentional with their philanthropy, and we connect them to specific opportunities that align with their values.

Dan: Philanthropy is something I talk about a lot with clients and our audience. There are many generous people out there. What tends to make your donors connect specifically with CityTeam? There are so many charities—why do they pick you?

Melanie: Two things stand out. First, our success rates. Many programs helping people overcome substance abuse have short timeframes and see sobriety rates under 20% for people who complete them.

Melanie: CityTeam’s recovery program is long-term—10 months—and our sobriety success rate is much higher, around 70%. Our women are a bit higher than our men, which we tease the guys about sometimes. But the big point is that after completing the program, most are still sober a year later—that’s almost two years of sobriety from when they came in.

Melanie: We’re also a faith-based organization, and some donors connect strongly with that. But overall, philanthropists want evidence that what they’re funding actually works. They want outcomes.

Melanie: Second, we’ve been very intentional about leadership and stewardship. Many nonprofits don’t have the luxury of leaders with deep business or financial backgrounds. Our president actually came from the corporate world—he was an executive in finance at Seagate before joining CityTeam.

Melanie: That gives donors confidence that their gifts are being carefully stewarded and maximized to help as many people as possible.

Melanie: Another thing donors appreciate is CityTeam at Work’s financial training. Almost all our clients come from a background of financial ignorance—maybe their families never budgeted, or there was chronic scarcity and fear around money. There’s often a mindset of lack.

Melanie: Donors love that we’re not only housing people and getting them off the street—we’re teaching them how to be financially stable and successful. That stability benefits not just them but their children, too.

Dan: That’s so good. There are many ways to do good in the world, but donors and volunteers want to know their time and dollars are being used well. Two things jump out to me: your success rates are incredibly high, and you’re focused on long-term sustainability—the impact lasts. Everyone wins when that happens.

Dan: Let’s talk about how you work directly with donors. How do they get engaged with you and your team?

Melanie: We partner with donors and try to connect them with opportunities that are meaningful to them. Some support us through straightforward cash contributions. Others use different giving vehicles that can be very advantageous, particularly for philanthropists.

Melanie: One of the most common and helpful tools we see is donor-advised funds. I’m not a financial advisor, but I know there can be significant tax benefits. The donor gets the tax deduction when they put money into the donor-advised fund, not when the dollars are granted out to nonprofits.

Melanie: That allows them to manage the timing of their tax benefits while keeping a pool of charitable funds ready for when they encounter causes they feel called to support more substantially.

Dan: You nailed that. I talk about donor-advised funds a lot because I think they’re underutilized. Many people think DAFs are only for the ultra-wealthy. That’s just not true anymore.

Dan: Quick pitch for donor-advised funds for anyone listening with charitable goals: DAFs let you control the timing of your tax deduction, invest the funds professionally, and then decide later which charities to support and when.

Dan: For example, I often work with professionals who have a really big income year—that’s a perfect time to load up a donor-advised fund. You might not even know yet where you want to give. A couple of years later, the DAF has hopefully grown, and when you discover an organization like CityTeam, you already have charitable capital ready to deploy and can make a bigger impact.

Dan: So, great explanation, and thank you for setting me up for my little DAF commercial.

Melanie: Absolutely. And to build on that, we ran a capital campaign during COVID—interesting timing—to acquire a 50-unit apartment complex for women and their children coming out of homelessness.

Melanie: 40–50% of those women are fleeing domestic violence. This housing gives them a safe place to heal and rebuild. When that campaign launched, we had donors of different sizes who could use their donor-advised funds to step in more significantly than their regular cash flow might allow.

Melanie: They had already taken the tax deduction when they funded the DAF. Now, they could use those funds to support a project they were deeply passionate about. It was a win-win: great for the women and families, and also well-timed and efficient for the donors.

Dan: Love that. It really does check a lot of boxes.

Dan: Let’s zoom out. Where do you see your organization—and philanthropy in general—going in the future?

Melanie: It’s a fascinating time. One of the biggest pressures nonprofits face right now is the speed of change. Digital marketing is evolving rapidly. There are more and more organizations, more noise, more things competing for people’s attention and dollars.

Melanie: At CityTeam and among our peers, we’re really focused on diversifying how people can get involved. This year, for example, we’ll start accepting cryptocurrency donations. Five years ago, that might have sounded fringe. Now, it’s just another way for certain donors to engage.

Melanie: Different generations also want different things. Younger generations want to be more hands-on. They care deeply about impact and want to see and feel the change they’re helping create. They want deeper involvement, not just writing a check.

Melanie: So nonprofits have this big opportunity—and challenge—to ensure we’re not leaving anyone out. We want ways for every person who cares about our cause to engage, whatever their age, time availability, or preferred giving method.

Melanie: That means rethinking internal team structures, the tech we adopt, and the types of engagement we offer. Someone in their 70s might want to engage very differently from a young family with toddlers who loves the work but is pressed for time.

Melanie: I think the nonprofits that will thrive are those that can pivot quickly, offer generationally appropriate engagement, and leverage technology to make it easy to find and support them.

Dan: I learned a few things there—that’s really helpful. It’s wild to see how technology touches every field, including yours. Very cool that you’re accepting crypto; that surprised me a bit, in a good way.

Dan: Alright, we’re shifting gears. You are officially entering the lightning round. We never tell our guests about it; we want it organic.

Dan: I’m going to ask you a question, and you give the first thing that comes to mind. It can be one word, or a longer thought—anything in between. Ready?

Melanie: Okay, let’s go.

Dan: Coffee or tea?

Melanie: Definitely coffee. We just got a new espresso machine and I’m obsessed.

Dan: Love it. I had an espresso earlier today myself. One meal for the rest of your life—what is it?

Melanie: French fries.

Dan: Love it.

Melanie: It’s so unhealthy. I’m probably 80% healthy so I can be 20% unhealthy, and that 20% is definitely French fries.

Dan: Fair enough. What’s one tool or piece of technology—hardware or software—other than your phone or computer that you can’t live without?

Melanie: Music. So, some way to play music—a Bluetooth speaker, something like that. Music connects across backgrounds and is powerful.

Dan: Great answer. Do you have a favorite quote or phrase about life, success, philanthropy—anything?

Melanie: I think about being generous with what you have. Every person has something to offer, and it’s easy to wait until you “have more.” I try to live by the idea: be generous with what you can offer today.

Dan: I love that: be generous with what you have to offer today. That will change over time, but today is what you control.

Dan: Do you have a favorite book?

Melanie: That’s hard. I have so many books I’ve been meaning to read and haven’t yet. One that does come to mind is an older book: Things I Wish I’d Known Before I Got Married. It’s full of questions you and your fiancé can walk through to prepare for marriage. I’m big on preparation.

Dan: Love it. I’m going to give you a book recommendation too since you mentioned prep and habits. The book is Atomic Habits. You mentioned habit stacking—it’s a big theme in that book.

Melanie: That’s actually on my reading list! And funny enough, a friend pointed out I was “habit stacking” before I knew it was a term.

Dan: Perfect segue. Do you have a personal hack you live by that you can share?

Melanie: Habit stacking. I’m very process-driven. I try to pair tasks to save time—like scheduling phone calls while I’m driving (safely, hands-free) or overlapping activities where it makes sense. Doing two compatible things at once helps me protect time for what matters.

Dan: Love it. What’s one bucket list item you’ve already accomplished?

Melanie: My connection to CityTeam actually started when I went through their residential program myself. I struggled with substance abuse and now have been sober for 14 years.

Melanie: A big bucket list item for me was being in a position of influence where I could support the same program that helped me. I didn’t know what that would look like at the time, but I knew I wanted to give back—financially, with my work, or both.

Melanie: Now, I get to raise funds for the exact program that I went through—and my husband and I also personally support CityTeam. It feels like a full-circle moment and is definitely high on my list of life accomplishments.

Dan: Good for you. That’s powerful. What’s one milestone you’re currently working toward, personally or professionally?

Melanie: Right now it’s related to time management. I’m quick to say “yes” to a lot because I care about many things. Between work at CityTeam, volunteer roles at church, family, and being a mom, I’m focusing on that elusive idea of balance.

Melanie: I know “perfect balance” isn’t realistic, but I’m trying to adjust wisely for the season I’m in—being more intentional about what I commit to.

Dan: I like that—life has seasons, and you have to embrace them.

Dan: Last one: if you could give one piece of advice to your younger self, what would it be?

Melanie: I’d tell my younger self that the decisions you make when you’re young matter more than you realize. I really wish I’d pursued financial education earlier.

Melanie: My husband and I both came from families where money wasn’t taught. I was raised by a single mom, and we were very poor. We had to educate ourselves as adults, which means we got a later start with investing and planning for the future.

Melanie: I wish I’d learned about money sooner so I could have set myself up even better. Now, we’re working hard to pass that knowledge on to our child.

Dan: You’re preaching to the choir. A big part of what we do with this community is trying to close that education gap. And I love that you’re focused on not just passing down assets, but passing down knowledge.

Dan: Melanie, this has been awesome. I really enjoyed the discussion.

Dan: If listeners want to connect with you, learn more about CityTeam, or collaborate, how can they reach you?

Melanie: Our website is cityteam.org. People who need help can find resources there, and those who want to give help can see different ways to partner.

Melanie: My name is listed on our legacy giving, stock donation, and donor-advised fund pages. My email is m.davis@cityteam.org.

Dan: Very cool. Melanie, thanks so much for sharing your time and insights today.

Dan: That’s it for this episode. As always, you can find our podcast, newsletter, and YouTube channel—all free—at makingsenseofyourmoney.com. And especially in the spirit of today’s conversation, remember to prioritize your version of a rich life.

Dan: Cheers, everybody.

Resources & Links

FAQs

What is CityTeam, in simple terms?

CityTeam is a faith-based nonprofit that helps people facing homelessness, addiction, incarceration, and food insecurity. They offer residential and transitional housing, recovery programs, job skills training, financial education, and food support—all free to those who need them, funded by donors.

How is CityTeam different from a typical homeless shelter or rehab?

CityTeam focuses on long-term transformation rather than just short-term relief. Their recovery programs are 10 months long, with strong follow-up sobriety outcomes. They combine safe housing, case management, job skills training, and financial literacy to equip people for sustainable independence.

How can I support CityTeam if I’m a high-earning professional?

You can give directly (cash or recurring gifts), donate appreciated stock, or use a donor-advised fund to time your tax deduction and then recommend grants over time. You can also explore corporate giving, sponsorship, or volunteering—especially if you want your time and skills to complement your dollars.

What’s a donor-advised fund (DAF), and why does it keep coming up?

A donor-advised fund is like an investment account dedicated to charitable giving. You make contributions (often in big tax years), receive an immediate tax deduction if eligible, invest the funds, and then recommend grants to nonprofits like CityTeam whenever you’re ready. Melanie highlighted that many CityTeam donors used DAFs to make larger, well-timed gifts—especially during major projects like buying housing for women and children.

Can I give something other than cash?

Yes. Many nonprofits like CityTeam accept gifts of stock, distributions from donor-advised funds, corporate matching contributions, and—increasingly—cryptocurrency. Check CityTeam’s “Ways to Give” page or contact their development team about the types of gifts they currently accept.

Is my donation tax-deductible?

In most cases, gifts to qualified 501(c)(3) organizations like CityTeam are tax-deductible if you itemize deductions, but the specifics depend on your situation and current tax law. Always consult your tax advisor to confirm how a particular gift will be treated for you.

Disclaimer

The conversation in this episode and the content on this page are for educational and informational purposes only and do not constitute tax, legal, or individualized financial advice. Charitable strategies such as donor-advised funds, stock donations, and other planned giving tools have eligibility requirements and tax consequences that vary by person and jurisdiction. Before implementing any philanthropic, tax, or investment strategy, consult with a qualified tax professional, attorney, and/or financial advisor who understands your specific circumstances.

Next Steps

If this episode inspired you to think more intentionally about your giving, here are two simple next steps:

1. Clarify your “impact thesis.” Write down the 2–3 issues you care about most (e.g., addiction recovery, homelessness, financial literacy). Use that as a filter for future gifts so your giving is more focused and meaningful.
2. Explore your giving structure. Talk with your advisor about whether tools like a donor-advised fund, stock gifting, or charitable “buckets” in your financial plan make sense. Then identify one organization—like CityTeam—that aligns with your values and start building a relationship with them.