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I began my start-up career at age 8, taking my grandmother's magazines, clipping articles, stapling them into my own creation and selling them door-to-door. My career as a media aggregator was short lived, but as a teen I joined one of America's first ISPs (Our class B was 155.212), where I built Web sites.

After creating the first online college application, I skipped college to become Netscape's youngest employee in 1996, where I worked with giants (marca, jimb) who were generous in teaching valuable lessons. I was product manager for our browser, worked on the anti-trust suit, and helped launch mozilla.org.

In 1999, I co-founded Tellme with Mike McCue. What followed were ten years of startup lessons learned, with very talented people. We built a profitable business with over $100 million in ARR. Our 300+ employees made speech recognition part of everyday life. We pioneered voice mobile search, years before "Siri." In 2007, Microsoft acquired Tellme for nearly $1 billion.

In 2009, I returned to New England to bring home a Silicon Valley spark, founding Upserve in Providence with to help restaurateurs thrive with an all-in-one platform for point of sale, payments, analytics and more. We were named "One of America's Most Promising Companies," recognized for 6 consecutive years as "Best Place to Work," and first RI firm on the Forbes 100 list. In 2018, after growing Upserve to over $35 mm in ARR and securing a strategic investment from Vista Equity, I transitioned from CEO to a board advisor role to pursue my next adventure as a VC. Lightspeed Commerce acquired Upserve in 2020 for about $500 million in the (then) largest-ever exit for a RI tech startup.

I joined Foundation Capital in 2019, where I partnered with founders building companies from the earliest stages. In 2024, I'm returning to my entrepreneurial roots.

Education Reformer

I had an unusual educational path: skipping college to join "start-up U" in Silicon Valley. My parents gave me opportunities at great schools. I was lucky.

Unfortunately many low-income children, especially children of color, lack access to effective schools. America's achievement gap is the greatest civil rights injustice of our generation, and I aim to do something about it.

In 2007, Rhode Island Governor Carcieri appointed me to serve on the Board of Regents, the state's chief education policy-making body. Soon thereafter, working with Mayor Dan McKee, House leadership, CER, DFER, and others, we passed an ambitious expansion of RI's charter school law, ending a ban on such schools. In 2009, we opened Blackstone Valley Prep Mayoral Academy; by 2014 it became the state's highest-performing school in 8th grade math, reversing the achievement gap: low income students of color outperform wealthier peers, proving demographics do not determine a child's destiny.

Working alongside prominent local leaders, I shared the case for education reform. I recruited Teach for America to our state, and I recruited Deborah Gist to become RI's Commissioner of Education, the first change in leadership in 17 years. Our strategic plan to improve education won President Obama's Race to the Top, the largest competitive federal grant win in Rhode Island history ( $75 million, with another $50 million that followed).

In 2010 I completed my term on the Board of Regents, and joined the board of RI Mayoral Academies, where we are scaling up our success to over half a dozen schools serving thousands of kids across the state.

Given the slow pace of policy change, this is a good start. But in the face of the largest some of the largest achievement gaps of any state in the nation, Rhode Island has only just begun to address this daunting yet urgent inequity.