Rebecca “Becky” Connolly

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Becky is a Co-founder and Managing Partner of Tiger Iron Capital and a 25-year veteran of the venture capital industry.  Becky’s passion for the venture capital industry began at Boston College Law School when a partner from Testa, Hurwitz & Thibeault was a guest lecturer in her corporate tax class.  Her innate geekiness was piqued hearing about the start-up companies and venture capitalists that the then-venerable Boston-based law firm represented.  She went on to begin her career at TH&T and served as general counsel and advisor to high growth technology companies, counseling them on a wide range of legal, business and strategic issues.  She also represented venture capitalists in their financing of start-up companies and provided them with general counsel and guidance in their fund formation and fund raising processes.  What Becky most enjoyed about her days as a lawyer, however, were her interactions with the venture capital community and watching the “sausage making” process of her start-up company clients growing from concept to public offering.  This caused her to change careers and become more involved in the investing side of the industry.


In 2000, she joined Everest Ventures as an investment partner, based in Wellesley, Massachusetts and found her calling as a venture capital fund investor.  Everest Ventures was then the venture fund-of-funds affiliate of Bessemer Trust and an affiliate of Bessemer Venture Partners.  At Everest Ventures she was responsible for identifying and selecting managers for the first fully-diversified venture capital fund-of-funds for the Bessemer Trust high net worth platform.  She was responsible for securing initial allocations and building relationships with leading venture capital funds, as well as designing the initial portfolio construction models and due diligence procedures. 

In 2004, Becky joined Fairview Capital Partners, where she was an investment partner and a member of the investment committee for the 12 years before founding Tiger Iron.  At Fairview, Becky was involved in the management of 22 multi-investor and single-investor fund-of-funds and customized separate account programs, representing a mix of institutional investors including state and municipal pension plans, corporate ERISA plans, endowments and foundations.  Although Fairview’s commitments to managers spanned the private equity spectrum from seed-stage venture capital funds through mid-market buyout funds, Becky was primarily responsible for identifying and selecting opportunities for Fairview’s venture capital portfolios and she served on a number of advisory boards of prominent venture capital firms.

When Becky is not researching the technology industry and hearing pitches from venture capitalists, she can usually be found doing something related to Track & Field, either coaching young children, watching her children compete, or running, high jumping, hurdling or pole vaulting herself, as she is a national champion and American record holder masters Track & Field athlete.  If she is not working out or competing, you can find Becky hanging out with her husband of 24 years and her two teenage children, preferably on the shores of Cape Cod.

Becky holds a Bachelor of Arts in Economics from the College of the Holy Cross and a Juris Doctor from Boston College Law School. 

Matthew “Matt” Schaefer

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Matt Schaefer is a Co-founder and Managing Partner of Tiger Iron Capital and a 22-year veteran of the venture capital industry.  After college, Matt settled into what he thought would be a long, if not exciting, career in public accounting with the once venerable Arthur Andersen & Co.  Nine years on, he wisely accepted an invitation to join a client of his, Bigler Investment Management Co, Inc. (“Bigler/Crossroads”), one of the nation’s earliest venture capital fund-of-funds managers.  At Bigler/Crossroads, Matt had oversight responsibility for all operational aspects of the firm and revamped a number of its legacy systems and processes.  He was also fortunate enough to learn about the world of venture investing from the inside, at the knee of some of the country’s best investors.  This led to a role on the investment team of Bigler/Crossroads and its successor organization, which prized his qualitative and quantitative analytical skills.


In early 1999, Matt transitioned to Fairview Capital Partners, where he was an investment partner and member of the firm’s investment committee for almost 17 years.  In that capacity, he was integral to the management of 22 multi-investor and single-investor fund-of-funds and customized separate account programs, representing a mix of institutional investors.  Early in his Fairview career, he experienced the boom and bust of the dot-com technology bubble, and the ensuing nuclear winter in the venture industry.  As he likes to say, “We know where the bodies are buried – and who buried them.”  His experience and good advice has been sought-after by many venture firms, which have requested his participation on their limited partner advisory boards.

Matt spends much of his free time monitoring the educational and career development of his two children to ensure they won’t join the boomerang generation and spoil the peace and tranquility he and his wife of 27 years enjoy as empty nesters.  He also likes to kayak, cook and work on projects around the house.

Matt holds a Bachelor of Arts in Economics and Accounting from the College of the Holy Cross.  (Becky is quick to point out that he graduated before she did.)  He is also a former licensed certified public accountant.