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About me

Creative, operator and investor, focused on media and emerging technology.

I’m Ben Winters. Taking what I’ve learned and earned from my ventures, I’ve applied it as an investor. I live on the Puget Sound in North Seattle with my wife, Taylor, and our son, Sebastian.

So far, I’ve trialed and errored — and sometimes succeeded — across three big waves.

Wave one Stock media

Helped build Punch & UpperCut Images, which Getty Images successfully acquired.

Wave two Digital agency

I founded the highly recognized WINTR (2009–2018), serving enterprises and startups, including American Express, Coca-Cola, Microsoft and Nike. We made whatever we could design and code, from art to apps. We won awards, and our work was covered in Fast Company Design, Wired and The New York Times.

I had a life-changing health crash during this ride, leading to a short period of status quo and, ultimately, a sale to Ideoclick, an Amazon-focused firm.

Wave three E-commerce

While at Ideoclick, I established ad products, gaining the position as the #1 Amazon Advertising agency partner, then led all client-facing and revenue-generating activity as Managing Director and then CMO. We raised a Series A from Accenture Interactive and GLP.

The company hit rough tides: the surge to scale brought on by Covid, then the natural contraction as buying behaviors normalized. Post-Covid, I accepted a board appointment as turnaround CEO to find an acquirer and beat the odds.

After a year off, I took on another turnaround, joining Oceanwing, an Anker Innovations company, as Chief Commercial Officer in 2024 to lead sales, marketing and partnerships in North America.

Investing

Over the last decade, I’ve been an investor in real estate and an investor in and advisor to startups.

Now: AI

I’ve been riding the AI wave, writing skills, creating agents and optimizing our interests across real estate (Winters & Co.) and executive leadership coaching (Every Day Future, the executive coaching practice of my wife, Taylor Winters). See examples.

Selected Press

Boards

Get in touch LinkedIn