Before Shopify, YouTube, and Facebook, there was OverstockArt. David Sasson launched the company on the Yahoo Store platform in 2002 in Wichita, Kansas. It sells original, hand-painted reproductions of works by Van Gogh, Monet, and more.

Much has changed since 2002, but not Sasson’s passion and resilience. He has faced legal crises, replatforms, and competitors. Yet OverstockArt thrives.

In our recent conversation, he shared his journey and outlook, and advice for budding entrepreneurs. The entire audio is embedded below. The transcript is edited for clarity and length.

Eric Bandholz: Tell us about yourself.

David Sasson: I’m the co-founder and CEO of We launched in 2002. We’re an ancient company by ecommerce standards. We sell art online. Our main product line is hand-painted oil reproductions of works by Van Gogh, Monet, Renoir, and artists of that caliber. We reproduce them by hand, and customers can choose the frame. We do all the framing in our facility in Kansas and ship to consumers nationwide.

Bandholz: How does copyright come into play?

Sasson: Everything we deal with is in the public domain. Copyright law is complicated. I’m not a lawyer, but the vast majority of art in the U.S. is in the public domain if produced before 1923.

There are global limitations due to treaties among countries. For instance, there’s art in the public domain in the United States but not in Europe. We stick to art produced before 1923.

Bandholz: How does your operational system work?

Sasson: We work directly with studios overseas. We built our own supply chain software, which we use to create orders for the studios. The orders include imagery, part numbers, and the quantity to make. The studio produces the reproduction and uploads a photo. We then approve or reject it. Once we approve it, the studio will prepare the shipment to our facility here in Kansas.

Our site shows photos of the reproductions, not the originals. Once customers place an order, it will usually ship the next day for three- or four-day delivery. Selling art requires holding very broad and very shallow inventory. We have a lot of variety. We anticipate what will sell and how many to hold of each piece.

We’ve built a fairly sophisticated supply chain and demand planning tool that tells us how many to order for each painting. The model helps us hold stock profitably. It’s not simple.

With Prime, Amazon changed consumers’ delivery expectations. Now everyone wants an item in two days. The closer we get to that, the better we are, although customers understand longer waits for custom orders.

Bandholz: You’ve seen many changes since 2002.

Sasson: In 2013, we almost went out of business due to copyright claims. We had to take down a lot of questionable art, including Picassos. We paid attorneys and others — the stress was heavy.

We had a strong 2012, and our studios struggled to meet the demand. We started 2013 at the same pace and suddenly faced a copyright legal crisis. We had to remove a considerable percentage of our stock, plus many of those items were in transit from our suppliers. So I’m paying for a product that I can’t sell, and I don’t have suitable replacements.

Our sales dropped by 50%, but our costs stayed the same. We went through all our cash, and I had to put money back into the company. We couldn’t focus on increasing sales because of legal problems. For a time, I was convinced we would go under.

We finally turned a corner in 2016. By 2017 we saw real success. By the 2017 holiday season, we were suddenly flush with cash and doing what we wanted, not what we had to.

I believed in our mission, and we came through, but it wasn’t without doubts and difficulties. If you’re a new business owner, be ready because these situations can happen. It can be challenging in the moment, but it will get easier.

Bandholz: Have you considered selling OverstockArt?

Sasson: An entrepreneur’s goal should be to build a great business. If you’re having fun, why not keep doing it? If I sold the company, I would probably start another one. It’s what I do. If the perfect opportunity presents itself, I might sell, but I’m not seeking it. I want to build a great company. If founders set out to create something amazing, everything flows from there. I don’t see a reason to do something else.

Every decision in life has consequences, especially for business owners. Many folks don’t want the responsibility, and it’s common to run into problems. But if we are willing to step up, do the work, and believe in ourselves, we can push through obstacles.

My number one suggestion to newer entrepreneurs is to take time to think. I spend much of every Friday away from the office, often at a coffee shop. I’ll bring paper and write. I’ll think of a question or a topic, start writing, and read what I wrote. That’s how I come up with solutions to problems. Entrepreneurs seek action. We see something and go after it. But we can improve and develop an edge by pausing to reflect and brainstorm.

Bandholz: Where can folks connect with you?

Sasson: Our website is I’m on LinkedIn.

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