
Tom Ricketts
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- Full Name
- Thomas Stuart ("Tom") Ricketts
- Title
- Co-Founder & Chairman, InspereX (formerly Incapital); Executive Chairman, Chicago Cubs
- Firm
- InspereX LLC (formerly Incapital LLC)
- Firm Type
- Financial services / fintech (securities underwriting, distribution & trading); personal angel investing
- Investment Stage
- Seed through later-stage private rounds (documented angel/strategic checks at Series B)
- Sector Focus
- Fintech / financial software, digital banking, consumer products
- Geographic Focus
- United States (Chicago and Midwest–centric)
- Location
- Chicago, IL / Boca Raton, FL
Background
Thomas S. Ricketts was born May 23, 1963, in Omaha, Nebraska, the son of TD Ameritrade founder J. Joseph ("Joe") Ricketts. He earned an AB in economics (1988) and an MBA (1993) from the University of Chicago, which named him a Distinguished Young Alumnus in 2005. He began his career on the trading floor, working as a market maker on the Chicago Board Options Exchange from 1988 to 1994, then held vice-president roles at Mesirow Financial (1995–1996) and in the brokerage/investment-banking division of The Chicago Corporation and ABN AMRO (1996–1999).
In 1999 Ricketts co-founded Incapital LLC, a firm built to give securities dealers and individual investors more efficient access to corporate bonds. As CEO through 2009, he created the flagship InterNotes platform and diversified the firm into certificates of deposit, agencies, mortgage-backed securities, structured notes, preferred stock and annuities. He was named to *Institutional Investor*'s "40 Most Influential in E-Finance" five times and was Ernst & Young's 2010 Midwest Entrepreneur of the Year in Financial Services. In February 2021, Incapital merged with 280 CapMarkets to form the fintech InspereX, where Ricketts serves as chairman; the combined firm and its predecessors have underwritten more than $350 billion of corporate and U.S. agency bonds. In January 2025, Scott Mitchell was named CEO of InspereX, with Ricketts remaining chairman.
Ricketts is best known publicly for leading his family's roughly $900 million acquisition of the Chicago Cubs, Wrigley Field and a stake in Comcast SportsNet Chicago, completed October 2009, after which he became executive chairman. He oversaw the ~$1 billion "1060 Project" renovation of Wrigley Field and the adjacent Park at Wrigley development (opened 2017), and the team won the 2016 World Series — its first in 108 years. He was named *Sports Business Journal*'s Executive of the Year in 2017. He is married to physician Cecelia Ricketts and has five children; his siblings include former Nebraska Governor and U.S. Senator Pete Ricketts and TMS Health Care founder Todd Ricketts.
Investment Thesis & Focus
- Primarily a financial-services operator and sports-franchise owner rather than a full-time venture investor; his private investing is opportunistic and concentrated in areas adjacent to his fintech expertise.
- Documented investments skew toward fintech and digital banking — a natural extension of Incapital/InspereX's mission of broadening investor access to financial products.
- Has also backed consumer-product companies (e.g., Bartesian), indicating openness beyond pure financial software.
- Typically participates as a strategic/individual investor within institutional rounds (e.g., a Series B) rather than as a lead seed check-writer, bringing capital-markets relationships and distribution credibility.
- Aggregator data (Tracxn/PitchBook) records a small, hand-picked portfolio, consistent with selective, relationship-driven angel activity rather than high-volume seed investing.
Notable Investments
- Verdigris Holdings / BrightFi — Parent of digital-banking-as-a-service provider BrightFi; Ricketts joined the company's strategic B-round investment that closed July 2021 (alongside Sterling National Bank).
- Bartesian — Consumer premium cocktail-machine company; listed among his personal investments.
- *(Note: "BrightFi" and "Verdigris Holdings" refer to the same parent-company investment.)*
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