Brandon Roop recalls a story he heard as a kid – of his grandfather handing his father a single $20 bill as he left for college, the only money ever given to him, yet a gift of profound weight for a family who had lived on and off food stamps. For Brandon, that moment symbolizes the value of a dollar, the responsibility of stewardship, and the power of legacy.
Today, as a Certified Financial Planner with Donaldson Capital Management (DCM) in Evansville, Indiana, he brings that conviction to his work with clients, helping them see that generosity is not only about financial strategy but about connecting hearts across generations.
His passion is guiding families to recognize the stories, sacrifices, and blessings behind their wealth and to build generosity into the legacy they will leave for their children and grandchildren.
1. Why is generosity important to you?
Growing up, my family didn’t have much but did the best with what they had. My mom took care of my sister with special needs, so she couldn’t work. We lived on a single income, but I still saw my parents budgeting faithfully and giving at church.
My wife and I got married in 2009 – the heart of the Great Recession. We had a lot of debt and very little income, but we did Financial Peace University through our church long before I became a financial planner. We learned to budget tightly while still making provision for tithing. That season showed me that, no matter how little you have, there’s still room for generosity.
Biblically, we’re called to be generous – like the widow who gave her two coins. You cannot outgive God.
2. How did you decide to bring generosity into your advisory business?
It’s been a refining process over time. I came to DCM because I felt passionate about the business and the autonomy it allowed. That freedom let me pursue interests like generosity without being held back.
What really shaped me was how my wife and I got through tough seasons by budgeting and making disciplined decisions. I realized I’m in a position to empower people who are often self-made millionaires. Many are inherently generous, but they’re also afraid of running out of money. I recognized my calling was to help them find peace and empower them to give.
I realized generosity conversations open hearts. We thought we knew our clients deeply, but once we started asking about planning, legacy, and generosity, we discovered we’d barely scratched the surface. Scripture says where our treasure is, there our heart is. Those conversations don’t just connect with the account holder – they connect with spouses and children. That’s where real impact happens.
That led us to create what we now call the Stewardship Journey. In our industry, when you talk about legacy, it’s usually financial. But there’s also a faith element and a family element. The Stewardship Journey is designed to help clients think about those deeper things, articulate them, and communicate them to the next generation.
3. Why do you think some advisors don’t talk about generosity with their clients?
Many stick to what they’re comfortable with. I spent most of my career focused on investments, so I had to grow in engaging in generosity conversations.
For some, it’s a lack of comfort, experience, or know-how. It takes intentionality to guide clients not just through financial planning and estate planning, but also into conversations about generosity and legacy.
4. Why did you choose to work with NCF?
We have clients who work with many different donor-advised fund providers. I really like how intentional NCF is and how willing they are to partner with me to serve my clients well.
When I met NCF, I saw the Saturday 7 newsletters, the events, and the way the Indiana office hosts 40-plus gatherings a year. That hands-on, relational approach matched how we serve at DCM. We want to love our clients, and NCF does the same. That’s why I chose to partner with them and build a relationship with their team.
My wife and I went through NCF’s Giving Strategy™ because if I recommend something, I want to experience it myself. Over several months, we created a family generosity plan. We prayed through it and then shared it with our kids. We even showed them how much we’ve given since getting married and our goal to give away a million dollars. Seeing our daughter’s reaction was powerful.
It reinforced how important it is to make generosity visible to the next generation. Much of our giving was invisible to our kids because it happened online. Now, by including them in the plan, they’re learning how to steward resources as we develop a family culture of generosity.
5. How have your clients responded to your mentioning generosity?
One client impacted me deeply. He was a dentist who came to us with half a million dollars. He told me God gave him a vision: When he reached $5 million, he’d shut down his practice and do medical missionary work.
A few years later, he called me and said, “Pull up my account.” It had just crossed $5 million. He told me he was closing his practice that Friday and leaving for mission work. Over the last decade, he has given away about $5 million, yet still has $4.5 million. Every time his account went above $5 million, he gave more.
6. What has been the result of making generosity part of your business?
Our growth has always come from serving clients well. But we’re now tracking generosity metrics as a firm. Clients are giving more, and we see the fruit: happier, more fulfilled people who refer us more clients.
We realized something important: Generosity connects us not only to the client, but also to the family. Talking about legacy and stewardship draws in spouses, children, even grandchildren. That’s how you build loyalty beyond one generation. Instead of being seen as “mom and dad’s advisor,” we’re building bridges to the next generation and securing the heart of the whole family.
For me, it comes back to what I call the value of a $20 bill. That moment of my dad being handed a single $20 bill as he left for college – that moment, for our family, carries enormous weight.
How do we steward the value of a $20 bill well? When my kids see that $20 and it elicits this visceral emotion – connection to the sacrifices and the people who have gone before them in the family tree – that’s the kind of legacy generosity can build when it’s made visible and intentional.
7. What is your number one tip for other advisors?
As advisors, we’re in a unique position to impact and shape family legacies. Generosity should be a central part of that. Many pastors aren’t comfortable teaching about stewardship and generosity, but we [advisors] are in a position to teach, coach, and empower clients in this area.
God himself gave his only Son – the ultimate act of generosity. That’s our model. Generosity is not just about numbers; it’s about connecting with hearts. When we help families formalize generosity and communicate it to their next generation, we’re not only shaping financial plans – we’re shaping legacies.
