When We Finally Talk About Death: Jason Brown on Love, Loss, and The Legacy Deck

Interview by Heather Anderson

Jason Brown’s wife collapsed from a sudden seizure just two weeks after their son was born. The diagnosis was brain cancer. Nine months later, she was gone.

In the midst of newborn life, medical chaos, caregiving, and “are you eating?” check-ins, he saw something most of us don’t realize until it’s too late: families either have the hard conversations—or they’re left in chaos after a loss.

Jason created The Legacy Deck, a set of guided conversation cards and journals to help families, men, grieving parents, and even pet owners protect what matters most while they’re still here to say it out loud.

You’ve said The Legacy Deck was born from the most painful chapter of your life — losing your wife when your son was only nine months old. Can you take us back to a moment in that early grief when the idea first surfaced, when pain started becoming purpose?

We were married for 10 years, building life and businesses together, and we were finally in that place of “Okay, let’s grow our family.” Two weeks after our son was born, my wife had a seizure. That’s when we found out it was brain cancer. Nine months later, we lost her.

People talk about these statistics — sudden loss, rare diagnoses — like they’re numbers, and you never think you’re going to become one of those numbers until you are.

I’ve always had a passion for family. Even before this, I cared about structure, communication, protecting what we’re building. I’d already watched families get torn apart after someone dies because nobody knows what was supposed to happen, who was supposed to do what, who was supposed to get what, how to honor the person. You see chaos, resentment, confusion, paperwork, people not speaking to each other for years.

I didn’t want that for my son.

For us, we’d actually had the conversations. My wife and I talked about wills, trusts, wishes, who makes decisions, how she wanted things handled, what mattered most to her if something ever happened. Not just money — emotional legacy, traditions, her values. Because of that, when it was actually time to make arrangements, I had clarity. I could focus on loving her and caring for her instead of fighting systems and arguing with relatives.

And that was the moment. I realized, “Okay. We were ready. Most people are not. 99% of people are not.” Statistically, something like 64% of people admit they’ve thought about end-of-life stuff, but still haven’t actually had the conversation. Meanwhile, we plan kids’ birthday parties, we plan vacations, we plan weddings. But we don’t plan for the only thing that’s guaranteed.

So the question for me became: how do I help other families have the conversations that spared us so much extra pain?

That’s where The Legacy Deck started.

A lot of people shut down in grief. You did the opposite — you built a tool to help other people talk. What made you realize these conversations had to happen now, not “someday”?

We shut down when we don’t have words.

That’s true in everything. If I don’t know how to say what I feel, I’ll protect myself by going quiet. I’ll tell myself “it’s fine, we’ll deal with it later,” because if I don’t acknowledge it, then maybe it’s not real yet.

The problem is “later” usually means “after.”

I started a podcast called “The When What If Happens Podcast” where I talk with people — professionals, caregivers, folks who’ve already lived through this — about end-of-life prep, planning, legacy, all of it. And the same theme came up over and over again: the conversations are hard, and nobody knows how to start them without it getting tense or triggering or sounding like you’re predicting someone’s death.

That’s when the deck became clear. We needed something neutral.

The Legacy Deck is 52 prompts. It’s literally a card game. You sit down as a family and instead of, “Hey, can we talk about what happens when I die?” (which makes everybody panic) it’s, “Okay, card says: who do you want making medical decisions for you if you can’t speak?”

You’re answering together. Nobody’s being singled out. It’s not, “Why are you asking me this, what do you know, are you okay?” It’s just: here’s the card, here’s the question. There are no wrong answers. You’re allowed to just say what’s true.

That shift — taking it out of accusation or fear and into curiosity — that’s the turning point. That’s how you normalize something that every single one of us is going to face.

You’ve called The Legacy Deck “a tool for legacy, healing, and truth.” Why is it so hard for families — and especially men — to talk about death, grief, or emotional legacy until it’s too late?

Culturally, men are told “protect and provide.” We know that script. But we’re not taught that protection and provision don’t end when you’re gone.

If I’m a husband, a dad, a son, “protector” doesn’t just mean “I handled things while I was alive.” It also means: did I make sure my people won’t be thrown into chaos if I’m not here?

Being a protector in your absence is things like: Did I make it clear who’s supposed to make medical calls? Did I get life insurance? Is there a will? Do they know where the accounts are? Did I communicate what I want so they’re not guessing and fighting and feeling guilty?

Being a provider in your absence means: I didn’t just leave assets. I left clarity.

Most men are never invited into those questions. Nobody says to them, “If the storm hits, who do you need to be?” We’re usually told, “Be strong,” which basically translates to “don’t show emotion, don’t ask for help, don’t admit you’re scared.” So we’re unprepared, and then we’re thrown into the fire and expected to lead everyone through it.

One of the big things I say is: you are still the protector and the provider after you’re gone, if you did the work ahead of time.

That’s legacy.

You were really intentional about every physical detail — the icons, the imagery, the way each deck feels in someone’s hands. Can you walk us through some of those choices, like the crown, the candle, the paw print, the family icon?

I didn’t want this to feel generic. I didn’t want one logo slapped on all the decks. Each kind of conversation deserves its own space and its own respect.

The men’s deck carries a crown. And I want to be really clear: that crown is not ego. That crown is earned. It represents standing in the storm for the people you love — financially, emotionally, spiritually. It’s a reminder to men that “king” is not just a title, it’s a responsibility.

The grief and healing deck carries a candle. That candle is presence. It’s warmth. It’s “the light is still here, even if it’s dim today.” When you’ve lost someone, people think that light’s gone. It’s not. It might flicker. But it’s still there.

The family deck uses an icon built around unity and generational strength. It’s about structure, clarity, and shared memory. Legacy starts in the home. It’s not just, “Where does the house go?” It’s, “What traditions do we keep? What stories matter? What do we want the kids — and their kids — to know about us?”

And then there’s one that most people don’t even realize is its own thing until they see it: the pet edition. That one has the paw print.

That deck came from a moment that honestly wrecked me. I was getting an IV, and the nurse walked in already crying. She’d just lost her dog. And if you’re an animal person, you already know — that’s family. She’s telling me this story through tears, and I’m sitting there realizing: we don’t have a safe script for pet loss, either. We act like we’re supposed to “get over it” fast because “it was just a dog,” and that’s not real. That love is real.

So now there’s a Pet Legacy Deck, too. Same 52-card format, same guided prompts, same journaling practice to capture the memories and keep them alive.

And that journaling piece is important. Every deck comes with a digital journal. You don’t just talk — you write it down. You create something your family can come back to. If it’s your pet, your kids can hold on to that story forever. If it’s your spouse, your kids will literally have your voice and your words, even if you’re not here later to say them.

That’s priceless.

You built one version of the deck specifically for men. Not many legacy or grief tools speak directly to men. Why was that important for you, and what’s surprised you most about how men are using it?

The men’s deck was actually the seed. Everything else grew out of that.

When my wife was going in for her first brain surgery, my business coach said to me, “Listen. You can cry now — cry in the car, cry on the way. But when you walk in there, you have to become that man. And I don’t just mean ‘be strong.’ I mean the man from the questions you never asked yourself before the storm hit.”

That hit me hard.

Because what he was really saying was: you didn’t prepare for the fire. You weren’t asked the questions that would’ve prepared you to stand in it. Now you have to become that man in real time, in crisis.

Most men never get asked, “Who do you need to be if the storm comes tomorrow?” “How are you going to show up for your kids if you have to do it alone?” “What are you afraid of?” “What would you regret not saying?”

So the men’s deck is built to ask those questions before the disaster, before the diagnosis, before the loss. It’s mental preparation. Emotional preparation. Financial preparation. Spiritual preparation.

What’s surprised me most is how hungry men actually are for those questions. People think men don’t want to talk. It’s not that. It’s that nobody ever handed us language or permission.

Give a man language and space, and you’ll watch him step into it.

“...if we can normalize end-of-life conversations the way we’re starting to normalize financial literacy, we’ll protect so many families from heartbreak-on-top-of-heartbreak.”

— Jason Brown

Let’s talk about the family conversations. So many moms carry the emotional labor of keeping everyone connected and okay. How do you see this deck helping families — couples, kids, parents — actually talk about the hard stuff?

A huge part of the family deck is about honesty and inheritance, and I don’t just mean money.

It’s: What do we want to pass down? What do we not want to pass down? What traditions matter? What values are non-negotiable in this house? If something happens to me, do my kids know who steps in? Do they know where the accounts are? Who the trustee is? Who’s supposed to make medical decisions for them? Who’s allowed to pick them up? What holidays are sacred to us? Which stories define us?

We say we want our kids to “know who we are,” but most of us have never actually told them in a way that can live past us.

And I’ll tell you how real that is. My aunt said to me one day, “I remember you two watching Home Alone all the time — was that like your Christmas thing?” I laughed and said, “That was her favorite tradition. Every Christmas she wanted to watch all the Home Alone movies.”

That’s tiny. That’s also everything.

Because now my kids will have that. And their kids will have that. Twenty, forty, eighty years from now, some kid in my bloodline is going to sit down at Christmas, watch Home Alone, and say, “We do this because my grandfather’s wife loved this movie.”

That’s legacy. That’s what “family” actually means.

And that’s before you even get to the legal/financial stuff like wills, trusts, beneficiaries, final wishes. We think we’re protecting our families by not “burdening” them with those topics. But not preparing them is actually the opposite of protection.

Either you write the story of your legacy… or somebody else will write it for you.

You’ve also created a version for grief and healing. Grief doesn’t end the story — it changes it. How can a conversation deck actually help someone who’s still in the middle of loss? And what would you say to a parent trying to help their kids grieve while carrying their own pain?

The grief deck is partly for the grieving person — and partly for everyone around them who has no idea what to say.

If you’ve ever lost someone, you’ve heard the same three lines a thousand times:
“How are you doing?”
“I’m so sorry.”
“Let me know if you need anything.”

People mean well. But those questions don’t touch what’s actually happening in your chest.

For two years straight, I heard those same three questions on repeat. And I get why — most people just don’t have language for grief. They don’t want to make it worse. They’re scared to say the wrong thing. So they stay surface-level.

This deck gives you better questions.

It helps you ask things that honor the person who’s gone, and keep their story alive, without poking at the rawest parts in a way that shuts someone down. It’s “Tell me something about them I should always remember,” instead of “Are you okay?” (Because no, you’re not okay. Of course you’re not okay.)

And in a parent-child situation — where you’re grieving and they’re grieving — this matters even more. You don’t always have capacity to generate perfect, therapeutic language in the middle of your own heartbreak. The cards do some of that lifting for you.

You’re not interrogating your kid. You’re sitting next to them saying, “Let’s pull one. Let’s answer together.” It makes space for them to talk, and it keeps you from going numb just to get through it.

It’s connection in the middle of the hardest part.

Tell me about what actually happens when people sit down with these cards. What have you seen in real families using The Legacy Deck?

This literally happened this morning.

My CPA sent me a video of her using the deck with her two sons. She read the instructions, pulled a card, and asked one of the questions: basically, “How do you want people to remember you?”

Her son said something like, “Whether it’s good or bad, I just hope people keep talking about me after I’m gone — hopefully in a positive light, based on the good things I tried to do.”

Then she answered. And her answer wasn’t hypothetical. She started talking honestly about what she’s done in her life, the ways she’s tried, the ways she’s not perfect, and then she went into this story about her own mom and what happened after her mom passed — including how messy it got because certain things weren’t prepared the right way. She said, “I didn’t get to have these conversations in my family. I want you to have them with me now.”

That’s generational change happening at a kitchen table.

After that, her son literally walked off with the men’s deck and came back like, “Mom, can we do more?” They played for hours. Hours.

When I watched that video, I told her, “That right there — that’s the tree. That’s the fruit.” Something that started as a seed in my heart while I was in the absolute worst season of my life is now planting different roots in somebody else’s family. That’s when I knew, This is why I built it.

For someone reading this who hasn’t experienced a major loss yet: what’s one small conversation they could start today to build their own legacy of connection?

Ask yourself this, out loud or in your journal:
“What conversations do I want people to be having about me when I’m gone — and what do I hope they’ll say I stood for?”

Not money. Not “she had a nice house.” I mean: What did I mean to them? What did I protect? What did I build? What did I make possible for them?

When you answer that, even privately, you start to see the gap between the legacy you want and the way you’re actually living.

And once you see that gap, you can choose.

That really hits. Because it’s not just a mom thing — I’ve seen this with everyone. We go to funerals and say all these beautiful things, tell all these stories about what someone meant to us, and then we all say the same thing: Why didn’t I tell them this while they were alive?

Exactly. That’s what The Legacy Deck is about. It’s a way to start those conversations now — while they can still hear you, and while you can still make changes if something’s out of alignment with the legacy you want to leave.

As you look ahead, what’s the vision? Where do you want this work to live — in homes, in faith communities, in parenting, even in how we teach kids about loss? And what do you want people to walk away saying after they’ve used these cards?

The goal is a million households.

A million households actively having these conversations, not just thinking about them.

I want to change the family script. Right now, for most people, the story is, “We never talked about that in my family.” I want the next generation to say, “No, we did talk about it. We knew. We were prepared. We understood each other.”

I want this to sit in living rooms, yes — but also in church groups, men’s ministries, grief support circles, financial planning meetings, therapy offices, end-of-life doula work, hospitals, hospice care, even pet clinics. Anywhere people are carrying love and fear at the same time.

Because if we can normalize end-of-life conversations the way we’re starting to normalize financial literacy, we’ll protect so many families from heartbreak-on-top-of-heartbreak.