Episode Details

The divorce process is one of the most life-changing things a person can go through — and somehow it’s still one of the most chaotic, confusing, and expensive. That’s exactly the problem that pulled tech founder Ryan Carson off the sidelines. A serial entrepreneur with 25 years in the tech world and three companies behind him, Ryan watched two of his three sisters — the people he calls his best friends — walk into brutal, costly divorces with almost no guidance except an attorney and a stack of baffling forms. Having grown up a child of divorce himself, he found it shocking how old-fashioned and disorganized the whole process still was. So he did what builders do: he started reading every divorce book in the library and asked a simple question — could technology and AI make this more humane and far more affordable without taking the humans out of it? The answer became Untangle, the AI divorce assistant, and the wisdom he’s gathered building it is the heart of this episode.

What makes this conversation genuinely useful is how practical Ryan gets. He’s candid that Untangle pivoted — it started as a low-cost guide for people representing themselves and now powers the discovery process for law firms through its AI agent, “Grace” — but he hasn’t stopped caring about the person sitting at the kitchen table at midnight, terrified and overwhelmed. His advice for anyone navigating divorce is refreshingly concrete: treat AI as a new tool in your divorce toolbox. “This is like the internet in 1999,” he tells Olivia — something everyone is going to learn to use. Pick an assistant you’re comfortable with, pay the modest monthly fee for the smarter models, and start using it to prepare: ask what financial documents you should be gathering, get plain-English definitions for the confusing legal and Latin terms in your paperwork, and surface the questions you didn’t even know to ask. The crucial caveat he repeats is one every listener should hear: you can’t trust AI out of the box for the correct forms or numbers — it’s a guide that helps you walk into your attorney or divorce coach better prepared, not a replacement for professional advice.

Underneath the tech talk, this episode is really a love letter from a brother. When Olivia asks for his words of encouragement, Ryan doesn’t reach for a product pitch — he thinks about his sisters. He watched them go through the hardest seasons of their lives, and he’s watched them come out the other side happier, healthier, more successful, and, in his words, even more alive. “They made it,” he says, “and you will get there.” That’s the mindset shift this episode offers: you don’t have to walk into divorce unarmed or alone, and the version of your life waiting on the other side can be brighter than the one you’re leaving. The takeaways are simple and immediately usable — lean on AI to prepare and ask better questions, gather your financial picture before you need it, and remember that knowledge and the right tools turn an overwhelming process into something survivable. For listeners in Connecticut (and the attorneys who serve them), Untangle is at untangle.us. For everyone else, the encouragement travels just fine: turn the lemon into lemonade, one tool at a time.

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