March 2026 | Giving While You’re Living

I once heard it said, “Do your giving while you're living, then you're knowing where it's going.”

A lot of people talk about legacy as if it begins with an estate plan. I think it begins much earlier than that.

In real estate, timing changes outcomes. In family wealth, timing changes people. The longer I spend around investors, operators, and families trying to do right by the next generation, the more I believe that one of the most meaningful things you can transfer is not a large amount of money at death, but well-timed support, clear values, and the chance to learn stewardship while you are still here to walk with them.

What I’ve Seen

I have had a lot of conversations with investors about returns, tax strategy, and portfolio construction. While those conversations matter, the heart of it is usually something deeper.

People want to know that their kids will be okay.

Not just financially okay. They want to know that their children will be grounded, responsible, and capable of making wise decisions. They want to know that the wealth they built will become a source of stability, not a source of drift.

I’ve seen families wait too long to have that conversation. They assume that if they build enough wealth, the rest will sort itself out later. Then life gets busy, and all of a sudden, the kids have grown up. 

I’ve also seen the opposite. A family offers a small amount of help, but they do it with clarity. Maybe it is assistance with a down payment. Maybe it is a co-investment. Or maybe it is helping a child understand debt, reserves, ownership, and what it means to hold an asset through a hard year. The dollars may be smaller, but the impact is often bigger because the transfer is not just financial, but rather relational and educational. 

In our business, I don’t think about capital in isolation; I think about what it enables people to build. I think about the investor trying to make thoughtful long-term decisions for their family. I think about the resident who benefits from stable, better-run housing. And I think about how much of life gets better when people have a little more predictability and a little more guidance.

What Changes and What Doesn’t

What is changing right now is the timing pressure around housing.

The median age of a first-time homebuyer has climbed to 40, and 22% of first-time buyers used a gift or loan from family or friends. Realtor.com also found that buying by age 30 is associated with roughly 22.5% higher net worth by age 50. That does not mean every early purchase is wise, but it does mean that the timing of access matters. Family support can meaningfully change the arc of a life when it is paired with judgment and discipline.

The market backdrop matters too. Realtor.com estimates the U.S. housing supply gap widened to 4.03 million homes in 2025, with about 1.82 million missing Gen Z and millennial households. In plain English, a lot of people are delaying household formation and ownership because housing is still hard to access. That makes earlier support more consequential than it used to be.

What does not change is that money by itself does not create maturity.

As my friend Greg Furer and I discussed on a recent episode of Real Returns, “the real work isn't about moving the money; it's building the framework and values needed to manage it." I’ve met very few people whose deepest concern is maximizing the number on a future statement. Most want to know their family will be able to carry responsibility without being carried by comfort.

That is one reason that I like real estate in my family’s long-term plan. It’s concrete. It forces tradeoffs into the open. You have to think about time horizon, leverage, reserves, maintenance, operations, and what happens when the plan gets tested. It can teach patience. It can teach stewardship. It can also teach humility if it is handled carelessly.

In my own investing, I stay focused on durable, attainable multifamily in Heartland markets. I want assets that serve a real need, produce durable cash flow, and stand up under real operating conditions. Families need places to put capital that can compound responsibly. Residents need places to live that are safe, stable, and treated with dignity. I think those two things belong in the same story.

ROS Lens of the Month: Why

When families start talking about legacy, the first question should not be “How much.”

It should be “What is this for?”

A clearer “why” changes the whole shape of the plan. A vague purpose leads to vague plans.

Maybe the purpose is to help the next generation buy a first home without becoming house-poor. Maybe it is to teach children how to think like owners before they inherit anything meaningful. Maybe it is to create stability without removing responsibility. Maybe it is to direct more capital toward impact while you are still around to see it working.

I have found that once the “why” is clear, the tools become easier to evaluate. A gift may make sense. A loan may make more sense. A co-investment may make the most sense. Sometimes the best move is not transferring a large amount at all. Sometimes it is giving structure, accountability, and a real seat at the table.

Actions to Take

1. Move one legacy conversation forward by ten years. Do not wait for estate planning season to talk about family wealth. Ask what kind of support would actually matter in the next three to five years. A down payment, business seed capital, or guided co-investment may do more good now than a much larger transfer later.
2. Put structure around any help you give. If you help a child or grandchild buy, invest, or borrow, write down the expectations. Talk through reserves, budgeting, ownership, reporting, and what happens if the plan gets hard. Clarity and education are part of the gift.
3. Make sure your capital is teaching something good. Audit your holdings to see what lessons they are reinforcing. Your capital should be an extension of your character; a silent curriculum of what you believe is worth building and protecting. By aligning your investments with things that solve real problems or provide genuine value, you teach the next generation that wealth isn’t just a number to be maintained, but a tool for stewardship.

Closing

I just don’t think legacy is about how much money you leave behind. I think it’s about whether the people receiving it are more prepared, more grounded, and more capable because of how it was given.

That kind of wealth transfer starts long before any assets are passed down. 

If this kind of thinking is useful, I’d love for you to subscribe to Investing on Purpose and follow along each month.