Interview: Ben Weissenstein, Major League Young Entrepreneur

Ben Weissenstein Interview: Major League Young Entrepreneur

by Nick Scheidies and Nick Tart

Every kid has started a lemonade stand. Usually it’s not front page news. But, at the age of four, Ben Weissenstein was featured on the cover of The Houston Chronicle, touting lemonade for 25 cents a cup. Ben only earned a few dollars that day, but he came away with a thirst for entrepreneurship that motivates him to this day.

When Ben was 14, he helped his mom with a garage sale. She suggested that he could help friends and neighbors sell and organize their extra junk. So Ben and his friend started a business. In a few years, Grand Slam Garage Sales had expanded to offer more services and employ over thirty part-time workers.

Now 19, Ben and his booming business have been featured in Entrepreneur Magazine and on the Dr. Phil Show. He has started The Entitled Group, a company that helps musical artists like Mike Jones, Little Flip, Young Hash and Cory Gunz book concerts and other events. Ben has moved from Houston, TX to Tucson, AZ, where he is helping launch the first of many Grand Slam Garage Sales franchises.

The following is a short excerpt from 50 Interviews: Young Entrepreneurs (Volume 1).

Q:  How did you plan and organize your business?

A: Everything started as nothing. We started with just the principles of wanting to be professional, keep records, and keep our customers and workers happy. We just figured it out as we went. When I started Grand Slam Garage Sales with my friend Matt, we went to Walmart and bought two red polo shirts for about eight dollars apiece [as uniforms]. We thought we looked professional, at least. The red polo shirts turned into to blue uniforms with Grand Slam Garage Sales logos.

We knew we had to keep records to an extent, so we started by opening a Word document and writing, “We took in x amount of dollars, we had x amount of expenses.” Eventually that turned into a nice excel spreadsheet, which turned into software that we had developed so we could put in [financial] information.

Grand Slam Garage SalesOur first website was all right, but it was nothing special at all. We had a friend do it. Then we had another web guy do it, who did a better job. Then we had another web guy do it who did an even better job. Basically, I started not knowing much and I just kept learning as I went along. That’s the biggest thing: always learn, change, and grow with your business.

Q: How did you get in Entrepreneur Magazine and on Dr. Phil?

A: A lot of the press we’ve gotten has just been random press that’s come to us. It wasn’t from us sending out a press release. For example, I was just at my high school reading an email that said, “We want to do a story on you and blah, blah, blah.” Then I saw ‘Entrepreneur Magazine’ at the bottom. I was so excited that I told all of my friends. That definitely brought more credibility to the table and got the word out about Grand Slam Garage Sales.

Dr. Phil was completely random. I think they found out about us when they were searching the internet and saw the interviews we did when we were on FOX News in Houston. They did a story on us that was a lot of fun and got us a lot more prospective franchisees.

But before we really start franchising here, we’re going to be calling all sorts of press and getting our company’s name out there. The more press we get, the more credibility we have. Good publicity is good. I don’t believe that bad publicity is good.

Q: Anything else you would like to add?

A: Anyone can go check out my personal website and the official website of Ben the CEO Ventures. You can also check out Grand Slam Garage Sales, Entitled Group, and follow me at

This is an abridged version from Ben’s interview in our latest project, 50 Interviews: Young Entrepreneurs. There’s nothing revolutionary about garage sales, but Ben is creating and revolutionizing a garage sale industry. What makes him different is his drive. Ben has a bonfire burning in his belly and Grand Slam Garage Sales is about to blow-up! By the way, Ben is putting on a concert at Texas A&M on March 27th and is looking for sponsors. Contact him if you’re interested in sponsoring the event.

Ben Weissenstein’s Top Quote

“Everything started as nothing.”

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