I recently had the chance to sit down with Niki Weiss for The Digital Legacy Podcast, and it was one of the more meaningful conversations I’ve had in a while. We covered the emotional side of estate planning, the technology behind what we’re building at Trust & Will, and why this work means so much to me personally.
Estate planning isn’t just legal documents—it’s also about legacy, love, and empathy. It’s about making sure your family doesn’t have to navigate complicated court systems while grieving. And unfortunately, so many people only realize this after it’s too late.
When my wife and I started thinking about a will years ago, we were shocked by how expensive and inaccessible the whole process was. That frustration became fuel, and eventually, the foundation of Trust & Will. We wanted to remove the cost, complexity, and emotional roadblocks that keep people from protecting what matters most.
Talking with Niki reminded me how important it is to keep human stories at the center of this work. From helping people avoid probate to guiding families through the hardest seasons of life—we’re not just building software. We’re building peace of mind.
Grateful to have been a guest on the show. If you haven’t listened yet, definitely check it out. We cover a lot of ground and share insights that might just inspire you to take action for your own family.
Watch the episode on YouTube or read the full transcript below.
Digital Legacy Podcast: Episode 22 - Featuring Cody Barbo, Founder of Trust & Will
Niki: Welcome back to another episode of the Digital Legacy Podcast, where we talk about death and dying in the digital age. Today, I have Cody here. Cody is the founder of Trust & Will. Cody, we met a while ago, but before we even met, I knew about Trust & Will. You’ve been on the map making headway for years. Please share your story with our audience.
Cody: Thanks, Niki, and thanks everyone for tuning in. I’m Cody Barbo, an entrepreneur from Dallas, Texas, and I’m the founder and CEO of Trust & Will. We’re the nation’s leading estate planning platform, helping everyday families come to trustandwill.com to choose a will-based or trust-based estate plan. We make it easy, affordable, and offer high-touch customer support. Maybe you’ve seen our commercials, heard our ads, or seen us in your banking or credit card app. It’s been the honor of my life to build this company with the team for seven years now.
Niki: Seven years—and this isn’t your first startup either.
Cody: Number three. Second venture-backed business. They’ve all been hard—it’s still hard.
Niki: What was it about this model? How old were you when you came up with the idea?
Cody: I’m 35 now, so late 20s when I started thinking about this. I have co-founders who have been part of this since the beginning. Personally, I didn’t think I’d be doing this for half my career. But I was getting married in late 2017, and my wife and I had never talked about money, taxes, insurance, let alone a basic will. She had lost her dad when we started dating, and he didn’t have an estate plan. I saw the pain she, her brother, and stepmom went through with probate—years of struggle, no closure. You don’t really move on from losing someone, you move forward.
I saw an opportunity to do something for ourselves. I Googled estate planning in San Diego—we lived there at the time. One attorney quoted $3,000, another $5,000. When I asked why the $5,000 plan was better, he just said, “That’s my rate.” It was like paying more for the same car at a different dealership. It seemed crazy. I looked for online solutions, something like TurboTax, and found LegalZoom, but they’re not really an estate planning company. I didn’t see anything modern or cutting-edge. That was the validation for me, Daniel, and Brian—my co-founders. I call us elder millennials—we’re almost 40 now. We’re all married, homeowners, with kids, aging parents. We’ve experienced the ups and downs of life, so we have a personal connection to what we’re building.
The early frustration was the gap in education. People don’t know about estate planning. Then, where do you go to get started? Online? An attorney? The costs are ambiguous. Cheap might mean lower quality. Expensive might mean you overpaid for simple needs. We wanted to consumerize an industry historically safeguarded by attorneys—not in a bad way, but families don’t have time for all the technicalities. The goal was to build a brand, educate, and create a best-in-class product that’s simple, intuitive, and affordable.
Niki: You mentioned key reasons people avoid this—education and cost. Those two pieces alone stop people from creating a comprehensive estate plan.
Cody: Exactly. The average household would need to spend 5–10% of their annual income on an estate plan. But that money goes to mortgages, kids, everything else first. We wanted to remove the cost barrier with technology. But beyond cost and education, there’s procrastination. People don’t want to think about death, or challenges like divorce or a health diagnosis. We focus on the happy reasons but don’t shy away from the raw reasons people need to do this.
Niki: One of the big reasons for procrastination is the emotional blocker. How does Trust & Will help users get past that?
Cody: Even in the early days, our goal was to be present and consistent with great content. Some of our most-read articles answer basic questions: What is a will? What is a trust? What’s the difference? What is probate? We help people understand what happens if you die without an estate plan—you go to probate. How long does probate take? What does it cost? How much goes to courts that should go to your family?
We spend millions on TV, radio, and we’re top search results for over 70,000 terms. We partner with over 200 financial institutions and work with 17,000 financial advisors. Everything leads back to that basic educational content. We show that estate planning doesn’t take weeks or months—it takes 30–45 minutes. You don’t need an attorney present. But if you want help, we offer five days of human support and have a national estate planning attorney network. Our goal is to remove the friction and barriers that historically delayed people.
Niki: I have a client who had access to Trust & Will through their employee benefits. He had it for years but only started using it after we spoke. He was in his 50s, kids over 18, but still had that emotional block.
Cody: That’s common. Probate is something most people only understand after experiencing it. My father-in-law passed in California but had assets in Texas. That meant dealing with probate in two states. In California, probate can take up to two years. The courts are still backlogged from COVID. If your assets are over $184,000 in California, you go to probate. Even a small condo can push you over that threshold.
Probate is time-consuming and emotionally draining. You're grieving, and now you're expected to be a financial expert. There’s no “Domino’s pizza tracker” for probate. That’s why we acquired Easy Probate and now offer Trust & Will Probate. We've helped over 4,000 families settle estates in 30 states. It’s about helping people through grief with empathy and practical support.
Niki: It's a legal process intertwined with emotion. Empathy from professionals is crucial.
Cody: Absolutely. It’s given me a personal perspective too. Probate sucks—no one says it was great. But you can plan to avoid it. A trust-based plan can help. Retitle your assets into the trust, and you can avoid probate. I see it as a selfless act. You don’t do it for yourself—you do it for your loved ones. We’ve helped hundreds of thousands of families who either couldn’t afford an attorney or didn’t know where to start.
Niki: You’ve been in this space for a while. How do you see AI impacting estate planning?
Cody: In the early days, it was about survival. Five of us in a co-working space. First, we rolled out a Last Will and Testament in Texas and California. Then we expanded. We wanted to solve offline execution—you had to sign documents at a bank or with a notary. We did the first electronic will in U.S. history in Nevada in 2019. Now, 13 states plus D.C. allow for electronic wills.
With AI, we can use our data to help customers more. We created Plan Strength—a credit score for your estate plan. If you haven’t signed your documents or funded your trust, you’re at risk. AI helps us remind users when to update their plans and keep everything current. I updated mine last year when my second child was born. A notary came to the house within hours. It was seamless, and we want to make that level of service accessible to everyone.
Niki: Streamlining the process is key. But how do you help people realize they need this?
Cody: We have a quiz on our site—simple icons to help people decide if they need a will or trust. The main difference: a will still goes to probate, a trust helps avoid it. A trust offers more privacy and control, and it doesn’t have to be expensive. We help people update old wills, even ones from 20 years ago.
Niki: What should someone gather before they visit your site? Should they know who they want as executor?
Cody: Guardians for kids, healthcare agents, DNR wishes—those are the emotional blockers. But the factual part is easy. You can complete that in 10–15 minutes. The emotional part—like my wife and I deciding burial vs. cremation—takes more time. We make it easy for people to start, regardless of their knowledge. Whether it’s a happy or sad reason, we help people at every stage.
Niki: This platform is designed for all generations, but what about those less tech-savvy?
Cody: We want to be the default estate planning platform—for consumers, professionals, and institutions. The future is making estate planning more behind the scenes. AI can track life events and prompt updates. We help transfer wealth quickly and efficiently. We’re building this future with almost 100 people on the team.
Niki: I love that your product empowers people to live fully and die ready. It’s about peace of mind.
Cody: Exactly. It’s about empowering people. If you want to learn more, visit trustandwill.com. You can chat with our AI bot, Willie, or our human support team. I’m on LinkedIn and Twitter at Cody Barbo—let me know you tuned in.
Niki: Thank you so much!
Cody: Thank you, Niki.
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