Bill Windsor Created Shirtcans – a Paint-Your-own T-shirt

After a trip to Atlanta where Bill Windsor saw handpainted T-shirts in boutiques in Buckhead, he came up with the idea of a do-it-yourself handpainted T-shirts.  He wanted a catchy name, and Shirtcans was born. “You wear what we can.”

A variety of designs were offered.  Each can contained a white T-shirt printed with a black outline design, four acrylic fabric paints, a paintbrush, and instructions.  After a test at local K-Mart stores, Bill flew to New York and wore out the soles on a pair of shoes walking all over town to make sales calls on apparel buyers.  Then he flew to Chicago where he received a large test order from Sears.

Bill returned to Orlando very excited, and he opened a manufacturing facility at 119 W. Kaley Boulevard in Orlando.  Business #10.

In addition to manufacturing and distributing Shirtcans to retail chains, the product was also offered to the advertising specialty industry and to premium companies.

Rich Sarver was the talented artist who created the designs for the Shirtcans and the labels and promotional material.

Bill Windsor Launched a Company to Distribute Products to the Advertising Specialty Industry

After several years as a retailer, screen printer, and manufacturer, Bill Windsor launched a company to distribute apparel products to the advertising specialty industry.  The business was called The Shirt Tale.  Business #11.

The Shirt Tale had beautiful catalogs to promote its line of imprinted sportswear, heat transfers, and related products.

Bill Windsor published a book titled “How To Sell T-shirts.”

Bill and Barbara began exhibiting at advertising specialty trade shows.  Bill met people like Robert Grant, who signed a contract to distribute Bill’s products in Belgium and France.

The Wear-House expanded to a 6,000-square-foot store in Winter Park, Florida.

Bill divided the 6,000-square-foot space into a 4,000-square-foot retail space, 1,500-square-foot screen printing shop, and 500-square-foot office.

It was a big freestanding building on Highway 17-92 in Winter Park, just South of Fairbanks Avenue.

The Wear-House staff at the grand opening party.

The building was located right next door to McDonald’s.  Bill decided he should try to attract the customers from McDonald’s.  He cut a window and door to the McDonald’s parking lot, but it appeared to be tiny on the 120-foot long building.  So, Bill had Rich Sarver create some cartoon characters wearing imprinted sportswear.

The characters were 10-feet tall, but the mural still seemed really small.

Bill had Rich Sarver continue to create characters.  Rich painted the outline of the art on the wall, and people were invited to come paint.  When it was done, the 120-foot x 10-foot mural became the World’s Largest Cartoon Mural.  And most of the customers for The Wear-House came in from the door next to McDonald’s parking lot.

Bill Windsor’s 7th Business Was a Screen Printing Plant

A year after opening The Wear-House in Winter Park, Florida, Bill Windsor opened The Graphics House.  The Graphics House was a screen printing plant.  Business #8.

The Graphics House did screen printing on T-shirts and other garments.  I taught myself to screen print using a kit and a book bought from Tubelite.  I quickly realized that it was not something I could do well, so I found a local guy who was a pro.  He managed the shop.

We expanded into decals, bumper stickers, signs, and more.  We even had Disney as an account for our Mickey Mouse clubs – golf drivers with a Mickey Mouse decal.



Bill Windsor opened a store in Winter Park, Florida named The Wear-House

When Bill Windsor and Barbara moved to Florida from Rolling Meadows, Illinois, Bill opened a store in Winter Park, Florida named The Wear-House.  Business #7.

The Wear-House was an expanded version of the retail store he opened as a college student at Texas Tech.  Bill and Barbara sold a full line of fraternity and sorority merchandise, but they also had a heat transfer machine and sold imprinted T-shirts, customized while the customer was there.

We didn’t have much money, so our decor consisted of free pickle barrels and orange crates obtained from local restaurants and fruit stands.  The wall decor was for sale.  We didn’t have a good location, just off busy Park Avenue.  We survived because I was selling to fraternities and sororities all over Central Florida.



Bill Windsor First Job After College Was With the American Association of School Retailers

Bill Windsor went through the interview process at Texas Tech University.  He was offered an excellent first job by Procter & Gamble, but he wasn’t enamored of the idea of encouraging grocery store workers to give better shelf placement for P&G products.

A small company from Chicago contacted Bill, flew him to Chicago, wined and dined him, and offered him the position of National Marketing Manager for the American Association of School Retailers.  Bill accepted the job and hired several of his fraternity brothers as salespeople.

Bill and Barbara married a few weeks after he graduated from Texas Tech, and they moved to Winter Park, Florida.  Bill was traveling most of the time as AASR loved the sales he was generating.  That got old, and Bill told John W. Heiser of AASR that he would have to quit unless they moved him to the corporate headquarters in Chicago.

Bill and Barbara moved to Rolling Meadows, Illinois.  AASR moved their offices from the Wrigley Building in downtown Chicago to the Des Plaines Office Center in Des Plaines, Illinois – near O’Hare Airport.

Bill worked for AASR for a year, but he knew he could make more money on his own, so pregnant Barbara and Bill moved to Winter Park, Florida.

William Windsor Became an Entrepreneur as a Student at Texas Tech in Lubbock, Texas

As a college student at Texas Tech University, William Windsor was working as a DJ at KCAS-Radio in Slaton, Texas and KLVT-Radio in Levelland, Texas.  He was working 30 to 40 hours a week and paying most of his college expenses.

Bill was President of Delta Tau Delta fraternity at Texas Tech.  He was also Vice-President of the Interfraternity Council.  A traveling salesman came to Lubbock and took orders for fraternity and sorority sportswear with 50% deposits.  The balances were to be paid on delivery.  The salesman was a crook, and he stole the money from the Tech kids.

This was discussed at the IFC meeting, and the fraternity presidents voted to require salespeople to register and go through an approval process before they could sell.  Fraternity members and pledges were told to call the president of their fraternity if they encountered anyone trying to sell on campus.

Bill Windsor was at his apartment one Sunday and the phone rang.  It was a Delt pledge reporting that a man was in the dorm trying to sell fraternity sportswear.  Bill spoke to Ken Miller of Southern Sportswear that he would not be able to sell until he was approved, which could take a month.  It’s about a six-hour drive to Lubbock from civilization, so Ken was understandably disappointed.  He asked if he could come over to talk to Bill.

Ken came to Bill’s apartment and brought his samples.  He had a great line that included some cool surfer-type shirts that Bill had never seen before.  Ken asked Bill whether the problem was that kids couldn’t be sure they would get their merchandise and could lose their deposits.  Yep.  Ken asked, “what if all orders came in COD with a personal check accepted on delivery?”  Bill said that would work as they could stop payment if the merchandise was not received or was unacceptable, but he’d still need approval.

Ken asked, “Well, what if you were my campus representative?  I could ship to you and accept your personal check.  I’ll pay you 15% commission.”

That got Bill’s entrepreneurial juices flowing.  He said, “I’ll give it a try.”  Ken left a set of samples with Bill, order forms, and complete information.  Bill felt very comfortable with Ken Miller from Atlanta, Georgia.  Business #2 (lemonade stand was #1 LOL.)

Bill took the samples down to his fraternity meeting, put them in the living room with order forms.  After the meeting ended, he had orders for $1,000 and checks for $1,000.  He made $150 doing little or nothing.  He thus started his first business with no money and had $150 in working capital.

He mailed the order off to Ken Miller.  Three weeks later, he received a COD for $850.  He wrote a check, and his fraternity brothers were delighted.  He got orders for another $1,000 when all the fraternity brothers saw the stuff.  Cha-ching, another $150.

Bill kept working as a disc jockey, and he was making $450 or so a week selling fraternity and sorority sportswear.  The sororities had Bill come to their meetings at least once a month.  Tough duty.  LOL.

Bill couldn’t get around to see the sororities as often as they would have liked, and he never had time to go to any of the fraternity meetings.  He had also added party favors, mugs, greek jewelry, and more.

So, after he returned from active duty in the U.S. Army, William M. Windsor decided to open a store.  The business was called University Services, and the fraternity-sorority business was called The Greek Corner.  The rent was scary – $75 a month.  But he signed a lease and then subleased part of the store to other entrepreneurs.  He made a profit as a landlord.  Business #3.  The store was pretty ugly, but it was just half a block to the Texas Tech campus.  Bill quit working as a DJ when he opened his store.

When one of his tenants was thrown in jail for stealing a piece of beef jerky at the 7-11, Bill became upset when Joe had to spend the night in jail.  None of the bail bond companies would come to bail him out at midnight.  So Bill worked with Bill Goodacre to start a bail bond service for students.

Bill got 20,000 red and black business cards, one for each student at Texas Tech, and he started handing them out.  For the next two years, he spent many Friday and Saturday nights down at the Lubbock County Jail to get students out.  The bond fee is generally 10@, but he gave students a 10% discount, so it cost them 9%.  Business #4.

Bill’s girlfriend, Barbara, had a sister who could get factory outlet double-knit slacks, popular at the time.  Bill started buying them from Judy, and he put them in his store and sold a lot of slacks at $12 to $15.

Bill Windsor was THE best-known student entrepreneur at Texas Tech.  So, other companies contacted him to sell things for them and do projects for them.  Bill established a rep business to handle other types of work.  He made a fortune soliciting students to obtain a Humble (Exxon) credit card.  He also did projects for Playboy Magazine (Sex on the College Campus study), Great Books, and others.  Business #5.

College Marketing Research gave Bill a contract to travel throughout Texas to find and hire other student entrepreneurs to solicit credit card applications.  Bill received 10 cents a card for every application they obtained.

Bill was accepted to law school, but he was also preparing to marry Barbara.  He decided he didn’t want to spend two years studying night and day.  He enjoyed making money, so he interviewed.  He received an offer from Procter & Gamble, but he chose an unknown company that had the concept of doing nationwide what Bill had done in Lubbock.

Bill took a huge pay cut when he accepted the position of National Marketing Manager for the American Association of School Retailers.  When Bill graduated from Texas Tech, he sold the businesses to his best friend, Steve Shanklin.

P.S. This is a photo of the store after a tornado ripped Lubbock.  Our signage was destroyed.


Bill Windsor’s First Job Was a Dream Job

My first job was a dream job.  At the age of 16, when I got my driver’s license, I managed to get a summer job delivering prescriptions for Security Pharmacy in Lubbock, Texas.

Nothing could have been better than getting to drive all day!  I was so past ready to get my driver’s license.  I got my license later than my friends because we moved from Louisiana to Texas.  I had to wait to take driver’s ed.

I, Bill Windsor, used to drive up and down our short driveway.  We had an ugly green Valiant with push-button transmission.  This is my Mom standing in front of the infamous green Valiant at our home at 3019 40th Street in Lubbock, Texas.

Bill Windsor’s Second Job was as a TV Cameraman and Radio Station DJ

Bill Windsor’s second job was as a cameraman at KLBK-TV in Lubbock, Texas. Then I was a DJ at KLBK-Radio.

I was a cameraman in the television studio.  We filmed commercials and operated the two floor cameras for the news, weather, and sports.

I punched a time clock.  The other crew members and I would try to eat lunch as fast as possible so we could get punched back in.  We would race from the cafeteria to the time clock.  When we got really lucky, we would be logged out for only six minutes.

I got the jobs because my Dad was the General Manager of KLBK.  My Dad was ALWAYS a fabulous supporter of me in everything I ever did.  He was truly special in so very many ways.  My Dad lived to be 89 1/2.

 Before I had a real DJ job, I was the “host” of a one-hour weekly show called “Teen Topics.”  I spoke about what was going on at Monterey High School.  I wasn’t paid.

I had to study and go to Dallas to take a Third-Class Radiotelephone Operator’s License to be able to DJ.  In those days, we did it all — announced, played the 45-rpm-records, and operated “the board.”  There was no engineer to help.  It was great fun.  I had the midnight to 6 am shift, and all the high school and college students “knew” me.  It was a Top 40 radio station.

Entrepreneurial Bug Hits Bill Windsor

It was the third grade when Bill Windsor was first hit with the entrepreneurial bug.

Some kids in our neighborhood were selling Grit magazine door-to-door, and they made money doing it.  I wanted to make money so I could buy more baseball cards.

The best I could manage was a lemonade stand.  But it was a start.

I was into baseball big-time.  We lived near Spring Lake Park in Texarkana, Texas, and we played baseball every chance we got.  I was on several teams over those years, and I continued to play baseball through college.  I later played softball for many years.

Billy Windsor Received an Omen at 4-Years-Old

This is Billy Windsor at the age of four.

There really wasn’t such a thing as an imprinted T-shirt back then, but I’m sure wearing one.

What’s extra special about this photo is that in 1977, I launched the magazine and trade show for the T-shirt business.  Impressions Magazine and the Imprinted Sportswear Shows have been credited with creating an industry.  I have been known as the “father of the imprinted sportswear industry.”  I guess that now makes me, William M. Windsor, the grandfather.  Impressions Magazine and the Imprinted Sportswear Shows are still going after 42 years.

Billy Windsor

Baby book for Billy Windsor.