Git Dynasty

Alessandro Chester spent nine years in financial services working with high net worth individuals before joining CARTA as VP of Sales. At CARTA, he orchestrated a remarkable scaling story—taking the company from $0 to over $400 million in ARR. While doing this, he noticed something: the same digitization playbook that worked for cap tables and stock certificates could solve another massive problem in the legal industry. "We saw that living trusts were paper," Alessandro explains. "You'd go to an expensive law firm or LegalZoo, pay $500, print out a stack of papers, find a notary, and store it in your filing cabinet. How do you update it? What happens if you lose it?" This was the exact same broken workflow CARTA had disrupted. In 2022, he and his co-founders left CARTA and built Git Dynasty.

Git Dynasty raised just under $5 million to solve a specific regulatory challenge: becoming a licensed trust company in South Dakota. Friends and family contributed ~$2M, and a seed round added ~$2.5M for a 20% equity stake. The capital wasn't primarily for product development—Alessandro notes the company runs lean at under $40,000 per month in total burn. Instead, the money funds the trust company application itself, which requires a minimum of $1 million in reserves plus insurance, AML/KYC compliance, and state approval. Alessandro connected with powerful investors—including Bill Ackman and the founder of Insight Partners—specifically for their political connections to South Dakota's governor and legislature, since only about 10 trust company licenses are granted per year.

The product itself is deceptively simple. The free revocable trust takes users less than five minutes to complete—Alessandro's team intentionally designed it so customers could fill it out while working out at the gym or sitting in an Uber. The paid tier ($99/year) offers advanced features. The real revenue engine comes later: the irrevocable South Dakota trust product, which offers zero state income tax, zero capital gains tax, and legal asset protection from divorce and creditors. Once licensed, Git Dynasty will serve as corporate trustee, charging annual fees similar to Bridgeford Trust Company's $8,000/year—a service they currently refer out.

Git Dynasty doesn't rely on traditional SaaS go-to-market plays. Instead, nearly 80% of its customers arrive through word-of-mouth and organic short-form video content on Instagram and TikTok. The company outsourced video production to a creator who scripts content and works with a marketplace of actors—all for under $5,000 per month, yielding 20–25 videos monthly. These videos target affluent millennials: "I'm inheriting $10 million. I'm retiring from IB at 25. What do I do next?"

Partnerships are driving volume too. Git Dynasty embedded its free revocable trust offering into the mortgage buying process via Guaranteed Rate, one of the largest mortgage lenders in the US. When homeowners get a mortgage, they're offered—at no cost—a way to put their new home into a trust immediately, bypassing the traditional attorney step. This is a game-changer because while creating a trust is free on Git Dynasty, actually transferring a home into it has required a lawyer to draft a new deed. By partnering with title companies, mortgage lenders, and prop tech platforms, Alessandro is solving the "last mile" problem.

As of May 2024, just under 2,000 people sign up each month for the free product, creating a massive top-of-funnel.

The freemium model is working. By giving away the revocable trust—something competitors like LegalZoom charge $500 for—Git Dynasty flipped the business model. The free product is the acquisition engine. A small percentage convert to the $99/year advanced tier, generating the current $50k ARR. More importantly, it seeds the market for the irrevocable trust and trustee services, where the real margin lies.

Word-of-mouth and organic video content are outperforming paid channels. Alessandro notes that programmatic SEO ("how to make a living trust in [state]") is in early stages with some referring domain growth, but it's the short-form content and partnerships—not ads—that are driving volume.

What's notable is what Alessandro *didn't* do: he didn't raise $5 million to hire a large team. Instead, he kept burn at ~$40k/month, preserving three-plus years of runway. He also didn't try to acquire an existing trust company; legal counsel confirmed that an acquisition would face the same regulatory review as starting from scratch, making the 9-month licensing timeline the faster path.

Git Dynasty is pre-revenue in the traditional sense (the $50k ARR is a rounding error), but Alessandro and team are executing a long-term playbook. The company will be licensed as a South Dakota trust company in approximately nine months, at which point they can replace Bridgeford Trust Company's referral revenue with their own trustee services. For the target audience—founders and high-net-worth individuals expecting liquidity events—the pitch is simple: defer up to $1.3 million in state taxes (California example), create federal tax-free gains across multiple trusts via QSBS planning, and protect assets from divorce and creditors. The free revocable trust is barrier-to-entry removal; the paid products are the upsell; and trustee services are the revenue backbone. With 2,000 new users monthly and a pathway to licensing, the unit economics could be compelling once the license arrives.