Sometimes I Don't Know What I'm Doing
Chrissy Crawford | Art Advisor + Entrepreneur

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Why Should You Care

With more and more affordable options opening for young people starting an art collection, more and more affordable options for art buying are becoming available. Meet ArtStar, an online art gallery that offers art lovers the chance to collect museum quality, limited edition fine art prints by some of the best contemporary artists working today for a low cost, with the help of your own online advisor.

Chrissy Crawford, ArtStar founder, did some soul searching in her 20s. After college, Crawford headed out west to teach skiing and wait tables, waiting to find her “thing.” Harnessing an interest in art stoked while working at a museum in Aspen, Crawford moved to The Big Apple to pursue a masters in Contemporary Art. After finding the high price of a collecting an unfortunate barrier to entry for young people, ArtStar was born.

In her 20to30 interview, Crawford tells antics from her 20s and how every decision she made, good or bad, led her to found her own successful e-commerce business.


Chrissy Crawford is a New York-based art advisor who runs two scuessful online art galleries, ArtStar and Little Collector.

After earning her master’s degree in International Art Business from Sotheby’s Institute of Art in London, Crawford opened her art advisory business in New York City in 2006.

With the onset of the recession, many of Chrissy’s clients were faced with shrinking art budgets. She created a platform that would enable collectors to discover, collect, and live with the best contemporary art without having to hire a private art advisor, travel to art fairs or spend their entire art budget on one work. Thus, ArtStar was born. is an online art gallery that offers limited edition fine art prints by leading contemporary artists.

Chrissy also founded Little Collector, which works with leading artists to create contemporary art for kids. Their mission is to engage children with contemporary art from a young age.

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Moments where I don’t know what I’m doing? Daily. The highs are very high; the lows are very low.

It’s scary. You know, you don’t have something consistent, and you don’t have something that you can really count on. And you have to make a lot of decisions that really impact other peoples’ lives, and that’s scary as well. I think that’s more frightening for me than what impacts my life is thinking…can we grow at this rate, do I hire more people, can I keep it going, can I get people health insurance? All of that is very frightening.

But wacky stories from work? I wanna write a book about entrepreneurships and startups. They’re so many. The submissions we get sometimes… We had a woman when we started doing children’s books on LittleCollector who submitted her book of male nudes for us to sell on LittleCollector.

We definitely make like top 10 lists from every art fair of crazy questions that we’re asked, which are always fun.

I had a guy at an art fair in Miami approach me at my LittleCollector booth and wanted to sell me other children’s artwork that he had collected, which I thought was really weird. Or maybe it was photos of children. It was something like… I didn’t wanna see it.


Made By

Cinematography: Danielle Calodney

Edited By: Mert Erdman

Interviewed By: Laura Lehmann

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