An Angel in New York: Charles Smith



Charles Smith got into investing and the startup community in the mid-90s because he wanted to “give back in a way that scaled beyond my personal time.” Since then, he has gone on to invest in over a dozen companies, and has worked for and sat on the boards of ten more. He founded Extension Entertainment, a social music discovery platform. He is the owner of The Ineo Group LLC. He spent three years as the vice president of Etsy Inc., ten months as the vice president of sales at Tacoda and executive vice president of corporate development and planning at RealMedia. He is an accredited U.S. investor who invests in about eight startups per year at $25-50,000 each.

As someone who has invested for as long as he has, Smith has a lot of experience and a lot to say on the matter. His first angel investment was in Shelby, a web video and streaming platform. He remembers not being sold on the business originally, but he eventually changed his mind. “I loved the idea, I loved the team, I loved how hard they worked. That [was] something I want to commit to.” His most humbling investment experience was when, a number of times, companies told him they wanted a bigger name to invest. Despite those few rejections, Smith takes his various experiences, learns from them in terms of investing, and uses what he knows to help young entrepreneurs who are just starting out.

A graduate of the University of Richmond with a BA in political science., Smith currently lives in Brooklyn with his wife and children. He is a man of many interests outside angel investing and startups, including organic foods and sports. He keeps a personal blog, where he shares stories and photos of his family and pets, updates on his involvement with Hurricane Sandy recovery, discusses his fanaticism when it comes to football and baseball, and shares anecdotes and helpful advice about startups and investing.

Sector Focus:

Advertising, analytics, digital media, fashion, social media

Selected Investments:

Maker’s Row
Days by Wander
Le Tote
Have to Have
Overtime Media

Current Boards:

Extension Entertainment
First Growth Venture Network

Previous Boards:

Etsy, Inc.

Expertise Areas:

Digital media
Digital strategy
New Media

Social Media:

Personal Website

Memorable Quotes:

On the smartest thing someone said or did while pitching: “’ I am going to continue to use you, even if you decide not to invest. I want help from you.’ He read the way I approach things very well.”

Where he sees technology in 2018: “Wearable health monitors.”

Why he works in startups: “I love nothing more than helping entrepreneurs get companies going.”

How he chooses who to invest in: “I am much more comfortable with people whose desire is not to be an entrepreneur but to change the world.”

About the author: Cassandra Baim

Cassandra Baim is a recent graduate of Syracuse University, now living in Brooklyn, NY. While earning her degree in English, she worked on the editorial staff of a campus magazine and participated in two shows with the university’s radio station. She is a copyediting intern for AlleyWatch and enjoys music, books, crossword puzzles and a strong cup of coffee.

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