Raise with one serious investor. Not twenty tiny checks.

William Christopher Skelley’s through line started in Boston with his father. His father attended Harvard and law school, then spent more than twenty years at Polaroid as head of the Western Hemisphere. He left Polaroid in the early 2000s as Will was beginning his career. Will tagged along. Together they worked with startups across Silicon Valley and Boston on fundraising, marketing, operations, and board work, whatever the company needed next. Across about thirty years he has worked with 40 plus startups in those operator and advisory seats.

He then worked at General Electric and Bain Capital, and at Olympus from New York reporting to the board in Tokyo. He attended Harvard Business School’s Owner/President Management program. He connected with the Clayton Christensen network and joined Rose Park Advisors, working on the portfolio and sourcing companies through Christensen’s disruption lens. He was at the firm in the years it held Coupang.

He founded iFunding, one of the early real estate crowdfunding platforms in the US, and exited in 2017. CNBC quoted him calling iFunding “the e-trade of real estate investing.” The company shipped what was described as the first mobile app for real estate crowdfunding. The platform raised nearly thirty million dollars across deals for projects from Brooklyn to Austin.

When it was time to raise for the company itself, he crowdfunded the crowdfunding platform: a Crowdfunder raise toward two million dollars at a twenty million dollar valuation, with more than one million in the first days. Crowdfund Insider covered the CNBC Power Pitch, where the audience vote was seventy two percent in. The Real Deal covered the New York crowdfunding wave.

He now lives in Da Nang, Vietnam, builds Santara AI, which provides AI operations for short term rental operators, advises founders on business model and relationship first capital, and publishes on Substack. Advisory work is cash only. No equity. No success fees.