Rogo Founder and CEO Gabe Stengel: Over $300 Million Raised Despite 40 A-Round Rejections
Investor Patrick O'Shaughnessy released a segment of an interview with Rogo founder and CEO Gabe Stengel: despite the company raising over $300 million in total funding, around 40 institutions rejected the A round, with Keith Rabois being the only one to make the decision at that time.
Gabe stated that he met with almost all top-tier firms, including Sequoia, Kleiner, and Benchmark. The rejections were not just based on reviewing materials but involved meetings, one-on-one hours, investment committee discussions, meals, and even weekend chats, yet they still said no in the end. His judgment was that the rejection at that stage was directed at the founder himself.
Rabois got involved about a month after everyone else had rejected, at that time a partner at Khosla Ventures, questioning whether this was a reverse bet or just a "financial version of Harvey." Gabe countered: if the consensus was so clear, why did your friends all think it was a bad idea and not believe in me? In October 2024, Khosla led a $18.5 million A round, with Rabois joining the board, alongside participants like Jack Altman, Mantis VC, and BoxGroup, bringing total funding at that time to about $26 million.
Rogo was founded in New York by Gabe Stengel, John Willett, and Tumas Rackaitis. Gabe worked in investment banking at Lazard from 2020 to 2022, leaving at around 23 years old, and began coding at a dining table with Willett, who has a computer background from Princeton and was a former banker at JPMorgan, aiming to replace the repetitive tasks of analysts in building models, memos, and slides. He described the early product as very poor, with a fragile architecture of about 60 model call chains, which was later rebuilt each year as model capabilities improved.
Subsequent funding brought back names that had initially rejected them: in 2025, Thrive Capital led a $50 million B round, with JPMorgan Growth Equity, Tiger Global, and Positive Sum participating; in January 2026, Sequoia led a $75 million C round and opened a London office; in April of the same year, Kleiner Perkins led a $160 million D round, with a post-investment valuation of about $2 billion, bringing total funding to over $300 million. Public figures on the client side include over 35,000 financial professionals and more than 250 institutions, including Rothschild & Co, Jefferies, Lazard, Moelis, and Nomura. The new product Felix targets multi-agent processes for transaction screening, CIM writing, buyer outreach, and due diligence in data rooms.
The market structure is event-driven cognitive correction: during the A round, Silicon Valley lacked a sense of scale regarding financial infrastructures like Bloomberg, FactSet, PitchBook, and ION, viewing vertical scenarios as cheap imitations of legal AI; funding first flowed from Khosla, then back to Sequoia, Kleiner, Thrive, and bank strategic capital. The beneficiaries are Rogo, which captured the workflow entry point, and Rabois, who priced early, while the pressured parties are those who used "too much consensus" as a reason for rejection but later replenished positions at a $2 billion valuation in the D round.
Source: Public information
ABAB AI Insight
Gabe's path is not a standard continuous entrepreneurship but rather the productization of the tough work he just learned in investment banking. The two years of analyst training at Lazard combined with a computer background from Princeton determined that Rogo would sell to similar institutions from day one, rather than first developing a consumer chatbot. David Tisch from BoxGroup introduced them into the top-tier circle, resulting in a collective rejection after thorough due diligence, indicating that in 2024, financial vertical AI was still labeled as a "Harvey copy" on Sand Hill Road, while Harvey itself was following a law firm workflow, also founded by former junior lawyers.
The capital path is divided into two segments. The first segment is Rabois using Khosla's check to break the freeze, rewriting "all friends say no" into a non-consensus that can be invested in; the second segment is Thrive, Sequoia, Kleiner, and banks like JPMorgan, Barclays, and Citigroup increasing their stakes after the product has been embedded in the transaction process. Banks are both clients and shareholders, effectively tying procurement budgets and equity exposure to the same system. The money is directed towards London expansion, on-site bankers plus engineers, and agents like Felix who can complete due diligence across steps, rather than burning another round on a generic large model brand.
The benchmarks are clear. Harvey consumes legal documents, Hebbia tackles unstructured searches, Bloomberg and FactSet take terminal rents; what Rogo aims to do is integrate these capabilities into the investment banking production system, becoming the interface for transactions. The industry phase has shifted from validating whether "analysts can work fewer hours" to controlling workflows: whoever becomes the default operating system for data rooms, CIMs, and buyer lists will approach a new Bloomberg position.
The structural judgment is that technological substitution overlaps with the transfer of pricing power. Once the hours of junior analysts are cut by models, software begins to charge based on seats and processes, turning the banks' cost centers into recurring revenue for suppliers. The mechanism is: top-tier funds rejected in the A round with "not enough reverse" but later bought back exposure at a higher valuation after the old employer appeared on the client list; the real reversal occurred in the month when the product was still unappealing and the founder faced rejection in meetings, not in the D round press release.
ABAB News · Cognitive Law
The A round rejected the person, while the D round bought into a system that could no longer be denied.
Projects that are too similar to consensus often have not yet become consensus.
Being rejected by everyone first proves that the track has not yet been fully priced.