Lessons Learned: Serial Entrepreneur Heels a Pain

Like many serial entrepreneurs who build something from nothing, Jason Schultz was blessed with insight and good timing.

Born and raised in California, Schultz began experimenting with Tandy and Commodore 64 computers and bulletin board systems as a child. When the Internet blossomed in the early 1990s, he taught himself how to program and create digital graphics.

As a 16 year-old in 1996, in California, he formed his first business, Design Concepts, which built websites for businesses and optimized them for search engines like AltaVista.

In 1998, Schultz began building content-heavy websites, online forums, and animated interactive health websites to bring in passive income. He co-founded a dial-up Internet service provider, where people could use chat rooms, shop online, and do other web-based activities, closing it in mid-2000 when high-speed Internet access became widely available.

Jason Schultz

Jason Schultz

Also in 1998, Schultz heard a nationally syndicated radio show by an investment firm. He contacted the firm about building a website that would allow people to get real time stock information, use online formulas and automatic calculators.

Schultz worked with the firm until 2005. Always the entrepreneur, he used all his online experiences in his next business, a full-service Internet marketing company called Brutal Brainpower. Launched in 2004, it focused on search engine optimization, pay-per-click advertising, branding, and email marketing.

But it was the website he created in 2003, Heel That Pain, that Schultz loves like a “child of mine.” He continues to run the business today.

“Originally I created it as an affiliate business to help a friend sell his medical product, the HTP Heel Seat, a heel insert that helps people with heel pain and Plantar Fasciitis,” Schultz said.

The website made good sales, but the company had lost money producing items for a large order that never came.

“In 2008, my partner Kevin Grimes and I approached the shareholders and made an offer to buy the company. They accepted and we have been running it ever since,“ Schultz said.

In 2009 Heel That Pain, which continues to sell heel pain and Plantar Fasciitis products, earned $1 million in gross revenue, doubling to $2 million in 2012 and increasing to $2.5 million in 2013.

Shopping Carts

Schultz tried a variety of shopping carts available in 2003.

“They all sucked. They didn’t give us enough flexibility to customize them, so in 2004 my development team and I created our own cart. It was basic, yet we could set up a single page shopping cart and do multivariate testing of form fields to see what produced the highest conversions,” Schultz said.

The website’s shopping cart has been rebuilt several times.

“Today’s version lets us fully customize the purchase experience, manage customer information and product details, keep track of product inventory, and print picking and shipping labels for orders,” Schultz said.

He has a distaste for off-the-shelf shopping carts, viewing them as “complicated and largely built by engineers, not marketers.”

Web Design

Schultz admits his first website design in 2003 was very basic but the subsequent versions were better as his graphic design skills improved. Eventually he delegated the design work to professional graphic designers.

“What we noticed about our website is the best looking graphics are not always the highest converting. And you’re not in business to win design awards.” Schultz said.

“Don’t let your internal biases and opinions get in the way of your success. Listen to customers, perform user testing, and use hard data to make decisions.”

Credit Card Payments

Schultz has tried several merchant accounts and gateways but has had many bad experiences including “weird rolling reserves and dishonest terms.”

For the last few years, he has been satisfied with Wells Fargo for merchant account services, and Authorize.Net for his payment gateway.

“However, we’ve been working with Stripe, which creates application program interfaces to accept online payments, to customize their merchant tools to work with the new cart we’re launching. If all goes well we’ll use Stripe for our processing in the near future,” Schultz said.

Order Management, Inventory, and Shipping

Schultz has used many shipping systems over the years and found most of them print separate labels for the order contents, address, postage, and even the company records.

Schultz has streamlined the order management system in his cart to print one small shipping label that has all the necessary information.

Heel That Pain houses inventory in, and ships orders from, its 4,000 sq. ft. warehouse in Orange County, in southern California.


“I’ve used Rackspace for hosting for almost 10 years now. We have two dedicated managed servers as well as Rackspace’s cloud service,” Schultz said.


Schultz works remotely but has three employees, letting “technology do the heavy lifting.”

“Currently we employ one customer service employee, one shipping manager, who has a part-time assistant, and one sales manager. My partner Kevin works as our product developer and I manage technology and marketing,” Schultz said.

Search Engine Optimization

Schultz says he has used every white hat search engine optimization technique available, to help customers find Heel That Pain since he created it in 2003.

“These days SEO needs to be readable by spiders, yet the main focus should be on creating outstanding content,” Schultz said.

“Don’t create things for the search engines, create things that people will love. Love, not like.”

Product Sourcing

Heel That Pain manufactures its own products – heel seats, liquid insoles, splints, muscle soak salts, comfort pads, and socks — in California and China.

Schultz has just spent hundreds of thousands of dollars developing a line of footwear for people with heel pain.

“We are tooling our first pair of sandals, which should be available for sale this summer,” Schultz said.

Heel That Pain

Heel That Pain

Accounting Software

“We use the web-based version of QuickBooks to keep our books updated and complete. A CPA comes in several times a year to review the numbers and then do all the tax preparation work,” Schultz said.

Social Media

Schultz said one of Heel That Pain’s best sales drivers is happy customers telling their family and friends about the treatments.

Most of Heel That Pain’s social marketing campaigns on Facebook and Twitter have been unsuccessful.

“Instead we give our customers small incentives to share on social media what Heel That Pain products worked for them, and that helps spread the word,” Schultz said.

Customer Service

“You can try hard to make customers happy, but it’s tough, as anyone knows who’s ever answered the phone or emails at an ecommerce company,” Schultz said.

“Don’t make it impossible for people to cancel an order, or exchange a product. Even then, you’ll have your fair share of hate. I’m convinced no company is exempt from this so don’t let it discourage you when it happens.”

Biggest Mistakes

“We make mistakes all the time. Typos, funky code, you name it we’ve probably got them. Ecommerce companies are a work in progress. What works today might not work tomorrow,” Schultz said.

“You build, test, break, fix things, rinse, and repeat, and do the best you can with what you’ve got. If you wait for everything to be 100 percent perfect, you’re probably not going to make it.”

Biggest Successes

Schultz said Heel That Pain’s biggest competitive advantage has been its early adoption of new technologies and trends to increase awareness and win sales.

These included using SEO in 2003 to gain visibility, performing multivariate testing, adopting AdWords as a key advertising channel, and producing helpful videos before this became common ecommerce practice.

“While technology was important in the past, the range of products and services available today makes it easier to create ecommerce companies without any technological background,” Schultz said.

“So don’t get hung up on the tech, explore other areas like branding, creativity, and customer touch points where you can have a competitive advantage and make the most of them.”

Elizabeth Hollingsworth
Elizabeth Hollingsworth
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