Lessons Learned: Serial Entrepreneur Heels a Pain

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

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

As a 16 year old in 1996, in California, he formed his first company, Design Concepts, which built websites for companies and optimized them for search engines such as AltaVista.

In 1998, Schultz started building content-heavy sites, online forums, and animated interactive wellness sites to bring in passive income. He co-founded a dial-up online service provider, where folks can use chat rooms, shop online, and perform other online activities, shutting it in mid-2000 when high-speed online access became widely available.

Jason Schultz

Additionally in 1998, Schultz discovered a nationally syndicated radio series by an investment company. He contacted the company about building a site which would allow people to receive real time stock information, use online formulas and automatic calculators.

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

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However, it was the site he created in 2003, Heel That Pain, that Schultz enjoys like a”child of mine.” He continues to run the company today.

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

The website made good earnings, but the company had lost money generating items for a big order that never arrived.

“In 2008, my partner Kevin Grimes and I approached the bankers and chose to get the company. They accepted and we’ve been running it ever since,” Schultz said.

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

Shopping Carts

Schultz tried a wide variety of shopping carts available in 2003.

“They all sucked. They did not give us sufficient flexibility to personalize themso in 2004 my development team and I created our own cart. It was fundamental, yet we could establish a single page shopping cart and do multivariate testing of form fields to find out what produced the greatest conversions,” Schultz said.

The website’s shopping cart was rebuilt several times.

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

He’s a distaste for off-the-shelf shopping carts, seeing them as”complex and mostly built by engineers, not entrepreneurs”

Web Design

Schultz admits his first site design in 2003 was quite basic but the following versions were better as his graphic design skills enhanced. Eventually he delegated the layout work to professional graphic designers.

“What we noticed about our site is the best looking images aren’t always the maximum converting. And you are not in business to win awards” Schultz said.

“Do not let your inner biases and opinions get in the way of your success. Listen to clients, perform user testing, and use hard data to make decisions.”

Credit Card Payments

Schultz has attempted several merchant accounts and gateways but has had many bad experiences including”bizarre rolling reserves and unethical terms”

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

“However, we have been operating with Stripe, which generates application program interfaces to take online payments, to personalize their merchant tools to work with the cart we are launching. If all goes well we will use Stripe for our processing in the not too distant future,” Schultz said.

Order Management, Inventory, and Shipping

Schultz has used many transport systems through time and found most of these print different labels for the order contents, address, postage, as well as the company documents.

Schultz has streamlined the order management system in his cart to publish one little delivery label that has all of the essential information.

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


“I have used Rackspace for hosting for nearly ten years now. We have two dedicated servers that are managed in addition to Rackspace’s cloud assistance,” Schultz said.


Schultz works remotely but has three workers, allowing”technology do the heavy lifting.”

“Currently we use one customer service worker, 1 shipping manager, with a part-time helper, and one sales manager. My partner Kevin functions as our product developer and I handle marketing and technology,” Schultz said.

Search Engine Optimization

Schultz says he’s used every white hat search engine optimization technique available, to help clients locate Heel That Pain since he created it in 2003.

“These days SEO has to be readable by spiders, yet the primary focus should be on producing content that is outstanding,” Schultz said.

“Do not create things for the search engines, produce things that people will enjoy. Love, not enjoy.”

Product Sourcing

Heel That Pain creates its products — heel chairs, liquid insoles, splints, muscle soak salts, comfort pads, and socks — in California and China.

Schultz has just spent thousands and thousands of dollars creating a line of footwear for individuals with heel pain.

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

Heel That Pain

Accounting Software

“We utilize the online version of QuickBooks to keep our books updated and complete. A CPA comes in a number of times a year to examine the numbers and then do all of the tax preparation work,” Schultz said.

Social Media

Schultz said among Heel That Pain’s finest sales drivers is happy customers telling their loved ones and friends about the remedies.

The majority of Heel That Pain’s social marketing campaigns on Facebook and Twitter have been ineffective.

“Instead we provide our clients small incentives to talk on social media what Heel That Pain products worked for them, and which helps spread the word,” Schultz said.

Customer Service

“You can try hard to make customers happy, but it is hard, as anyone knows who has ever answered the phone or emails in an ecommerce business,” Schultz said.

“Do not make it impossible for individuals to cancel an order, or exchange a product. Even then, you will have your fair share of hate. I’m convinced no provider is exempt from this so don’t let it dissuade you as soon as it happens.”

Biggest Mistakes

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

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

Biggest Successes

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

These included using SEO in 2003 to get visibility, performing multivariate testing, embracing AdWords as a vital advertising station, and generating useful videos before this became common ecommerce clinic.

“While technology was significant before, the assortment of goods and services available today makes it much easier to make ecommerce companies with no technical background,” Schultz said.

“So do not get hung up on the technician, explore different areas like creativity, branding, and customer touch points where you may have a competitive edge and get the most out of them.”

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