The Future of Investment Banking: Inside OffDeal, The first AI-Native Investment Bank

Plus an interview with Colgate alumn and OffDeal’s first employee, Jacob Glassman '20

Goldman Sachs just partnered with Anthropic to integrate AI and automate some of their job roles. As these Wall Street giants begin to embrace this technology, one thing is clear: generative AI is rapidly reshaping the future of the finance industry. 

Yet while legacy banks are just beginning this transition, OffDeal has been built for it from the start. Founded in 2024, OffDeal is the world's first "AI-native" investment bank. Rather than bolting AI onto legacy processes, the firm was designed from the ground up with AI at its core. The firm has already engaged with thousands of business owners, driven multiple transactions to close, and assembled a team of investment bankers from top Wall Street firms. To date, the startup has raised $17 million, offering a unique case study into how AI can be directly embedded into financial services.

What’s so Special About Being First, and What Does AI-Native Mean?

With deals such as Goldman Sachs and Anthropic, AI companies are layering generative models on top of preexisting systems. While the success of such deals remains unseen, an issue may be inherent within these deals: can the technology be woven into traditional banking structures that weren’t designed for it? 

When the idea of "OffDeal" first originated, founders Ori Eldarov and Alston Lin considered two options. If they wanted to, they could build AI software and sell it to preexisting banks. However, this option faced barriers such as convincing traditional firms to adopt this newer technology. As a startup, they would have also faced difficult competition from AI giants such as Anthropic, OpenAI, and Gemini. So instead, they chose the harder and more ambitious path, building an investment bank from scratch, with AI embedded into every layer from day one, hence the term “AI-native.”

What Does OffDeal Do?

OffDeal's platform dramatically compresses the M&A transaction process for small businesses. Within seconds of taking on a new mandate, OffDeal scans its proprietary dataset to identify every relevant buyer, including private equity firms, strategics, and individual operators, then reasons through why each might be a strong fit based on acquisition history, sector focus, and deal size. From there, the system can draft and send personalized outreach emails, generate confidential information memorandums, and produce marketing teasers to advertise the deal. What takes a traditional bank week of analyst grunt work is automated within half an hour, at near-zero cost.

This is the whole point of building a bank rather than selling software to one. Every step of the workflow from sourcing and outreach to materials and diligence runs AI-first, with the human banker managing the models rather than doing the busywork. That frees OffDeal's bankers to do the work that actually matters, like negotiating terms, walking owners through purchase agreements, and guiding them through what is often the most financially and emotionally complex decision of their lives. As Glassman put it, the role becomes "part-time therapist,” building the kind of deep personal relationships that a legacy bank staffed with junior analysts simply cannot replicate at this deal size.

What Does This Mean for Colgate Students in the Future?

In Glassman's specific GTM role, he uses AI to sift through data, analyze the ROI of various marketing channels, and assist with research and development, using OffDeal's proprietary data to deeply understand prospects across their pipeline. Yet even as AI reshapes nearly every aspect of how businesses operate, Glassman believes the real leverage in the years ahead belongs to people who can sell. "The one skill that won't be automated is your ability to build relationships," he says. AI can generate content, run campaigns, and analyze data at scale, but it cannot sit across from someone, earn their trust, and close a deal.

This is why Glassman sees 2026 as "the return of the salesman." The more our world becomes saturated with generated content, the more valuable genuine human interaction becomes. The professionals who thrive won't necessarily be the most technical; they'll be the ones who can pick up the phone, walk into a room, and build real relationships.

Most importantly, Glassman advises Colgate students to take risks. As a fresh graduate, it is the prime time to try something new, such as joining an AI-driven startup. Jumping into these opportunities early may give outstanding returns in the future.

Before joining OffDeal as its first employee, Glassman had already built a track record working with well-established brands such as Grey Goose, Anheuser-Busch, Grubhub, New Balance, SiriusXM, and others. But in November of 2024, he came across what Eldarov and Lin were building, and the problem they were solving clicked. Thousands of small business owners were selling their life's work without real representation, leaving millions of dollars on the table. Glassman took a leap of faith and joined OffDeal as employee one. Today, the company has scaled to fifteen employees. His risk has clearly paid off.