Benjamin
Winters

Creative / Operator / 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. I co-founded a stock media brand and marketplace, Punch & UpperCut, which Getty Images successfully acquired.

Wave two — digital agency. I founded the highly-recognized WINTR (2009–2018), serving enterprises and startups. We made whatever we could design and code — from art to apps, for enterprise brands to sexy startups. We won awards, and our efforts were covered in Fast Company Design, Wired, and The New York Times. It was an exciting thing to create. 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 during this time. 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, to lead North American commercialization.

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

Now — AI. Most recently, 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 work spans AI deployment for demand generation, booking, and property optimization across multi-family and short-term (STR) vacation-rental operations. The aim is simple: automate every mundane task in sight, until routine operations — unit turns, maintenance requests, contractor deployments, accounting — run themselves on agentic AI.

• Punch & UpperCut
  Co-founded the stock media brand and marketplace; acquired by Getty Images.
• WINTR  2009–2018
  Founder of the award-winning digital agency for American Express, Coca-Cola, Microsoft, and Nike; work featured in Fast Company Design, Wired, and The New York Times. Acquired by Ideoclick.
• Ideoclick
  Built ad products to the #1 Amazon Advertising agency partner position; Managing Director, then CMO; raised a Series A from Accenture Interactive and GLP; later turnaround CEO.
• Oceanwing Anker Innovations
  Appointed Chief Commercial Officer (2024), leading sales, marketing, and partnerships in North America.
• Investor & Advisor
  Active in real estate and an investor in and advisor to startups.
• Seattle 100
  Profiled in Chase Jarvis’s Seattle 100: Portrait of a City.