Why We Invested in Hamilton AI

Gardiner Garrard

As an early-stage fintech investor, I’m often asked about how we’re approaching AI. While the investors who got in on the ground floor of OpenAI and Anthropic have already made their money, we’re investing in industry applications of AI, which will take another five to ten years to reach maturation. 

We believe the next wave of opportunity will come from AI-native vertical software companies that embed workflow-critical components, such as payment processing, into their platform.

That’s one of the reasons why we invested in Hamilton AI. 

Hamilton is bringing modern, AI-powered infrastructure and embedded payments to private aviation, a $60 billion industry that has long relied on fragmented software solutions and manual transactions. Rather than having customer service representatives spend most of their day generating quotes for flight requests – over 90% of which never result in revenue – Hamilton uses deterministic AI to automate quoting and trip sourcing. The company’s AI reads email, parses the unstructured data, and generates a quote without human assistance, freeing up significant time for representatives to focus on more meaningful customer support. 

Hamilton’s AI-native approach is already transforming the private aviation industry, but we were interested in leading their most recent funding round for another reason. The company has integrated banking, payment processing, and card services directly into its platform to facilitate seamless transactions. This is especially valuable for private aviation, which historically relied on credit cards or wire transfers for payments. However, these high-volume transactions could be flagged or blocked, resulting in significant disruptions to both the charter business and the client. 

What made the Hamilton investment even more attractive was the founding team. Hamilton is led by Wouter Witvoet, a repeat founder who previously raised $1 billion to build Secfi, the largest lending platform against private company stock. He also founded DeFi Technologies and took the company public (NASDAQ: DEFT), reaching a market capitalization of $1.2 billion. 

We believe Wouter is once again running a successful playbook with Hamilton: taking a high-value industry that depends on manual processes, automating it, and embedding financial services. We’re proud to back the team at Hamilton as they bring AI and mission-critical fintech workflows to the high-value private aviation industry.

Gardiner Garrard is the co-founder and managing partner of TTV Capital. Under his leadership, TTV has been an early investor in Green Dot, Bill.com, Cardlytics, MX, Greenlight, TaxBit, SmartAsset, among many others. Gardiner began his venture capital career in the late 1990s and was one of the first to recognize the broad implications of financial technology, or what we now call ‘fintech,’ on businesses and...