Twenty years as an early and founding operator — first employee, founding executive, co-founder — carrying quota and building the commercial engines that took companies from zero to exit. Goodwin Family Ventures brings that operator lens to every founder I work with.
In 2007 I joined three founders in a house in Cambridge as the first employee at FlipKey. What followed was a front-row seat to building an industry-leading vacation-rental marketplace — onboarding hundreds of property managers and tens of thousands of listings — through its acquisition by TripAdvisor. I stayed on to run North American sales and operations, where the team I built hit 120% and 110% of revenue target two years running.
Then came Drizly. Over six years as a founding executive — rising from VP of Sales to SVP — I helped build the commercial foundation of what became the most robust alcohol-delivery marketplace in the U.S., the business Uber went on to acquire for $1.1 billion. After that I took the founder's seat directly as co-founder, President and CRO of TorchPro, a sports-media company, where I learned as much from the hard parts as the wins.
That's three companies, three different markets, and one consistent role: the person who builds the repeatable commercial system underneath the growth. I've carried the bag, owned the number, hired and fired, written the playbook, and lived the messy middle every founder eventually hits. When I tell you something will or won't work, it's because I've watched it play out — not because I read it in a deck.
Alongside operating, I've made 50+ direct angel investments — plus fund positions backing well over 100 startups — and I advise and invest through York IE, a strategic growth and investment firm for B2B SaaS. That gives me a second lens on the same companies — I know what makes a business financeable and where founders quietly lose leverage. Goodwin Family Ventures is the home for all of it: my operating work with founders, my investing, and what my family builds next. The through-line is simple — real results from someone who's been in the seat.
An operator who's run the commercial function at scale — at the moment you need the judgment but can't yet justify the executive headcount.
The goal isn't dependence on an advisor. It's a repeatable GTM motion your team can run on its own — process, stage definitions, cadence, and clarity on what "good" looks like.
I know how your company gets underwritten and valued. That shapes how we build — toward an outcome a buyer or investor will pay for, not just this quarter's number.
If a bet is weak or the math doesn't work, I'll tell you and show you why. You're not paying me to agree with you.
Beyond advisory work, I partner with a small number of companies as an operator-investor — capital and a board seat alongside hands-on operating leverage. Not passive checks; aligned ownership in businesses I can genuinely help build.
The best starting point is a direct conversation about where you are and whether there's a fit. No pressure, no pitch — just an honest read on the situation.
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