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I have been building companies for over 2 decades across a range of verticals, from lending in 1994 to performance marketing in the the late 1990’s where I was the first agency, the first to go global and the first to be acquired.

- Gregory Shepard

My Startups

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BOSS Startup Science provides education and products grounded in BOSS methods to give start-ups a better opportunity to succeed.

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BOSS Capital Partners is focused on applying the battle tested BOSS Startup Science methodology to assist companies that have found product–market fit yet need additional operational assistance to achieve a reasonable financial exit.


Pepperjam is a performance marketing company offering brands a true all-in-one wholistic approach to “the new affiliate”. Formed out of a carve-out from Ebay Enterprise Marketing Solutions transaction and enhanced by the acquisition of AffiliateTraction, AdAssured and NDA, the business went through a transition to become one of the 3 largest networks in the world. The SaaS offering leverages unique data and preferences to acquire and optimize high-quality partners while providing data tracking with custom reporting dashboards and integrations for customized commission strategies that align with attribution models and incorporate affiliate into overall cross channel efforts. This is all accomplished while providing brand and traffic protection to minimize revenue loss and protect investments across search, social, domain, code, and content. Pepperjam was acquired by Partnerize in 2020.


AdAssured was a SaaS business that was founded out of AffiliateTraction’s need to offer its customers a wholistic multi-channel compliance solution. There was no such service available at the time, only fragmented technology stacks were available. The Business offered a single point platform for search, domain, content and coupon compliance. After two GTM strategies that settled on an aggregator approach offering its technology to agencies and networks to enhance the quality of their traffic delivered by affiliates to brands. The business was acquired by the newly formed Pepperjam in 2016 following the acquisition of AffiliateTraction and merged into the businesses' overall product stack.  


AffiliateTraction was the first affiliate marketing agency, the first to go international with offices in, UK, CA, US, AU and the first to be acquired. The business was the result of a pivot in the more general online marketing space, to a pure affiliate focused services offering and finally into a SaaS/Tech enabled services offering to strong established retail brands. The business survived many challenges including, the DOT BOMB, a recession and was caught in an industry and ecosystem transition to, analytics, attribution, compliance and an increase in brand expectations. Additionally, the industry went through a late expansion and contraction in affiliate networks and agencies. The business was acquired by eBay Enterprise Marketing Solutions in 2015 as a part of a cross-brand deal totaling over $900M. The transaction comprised the purchase and sale of numerous companies and was awarded, Tech Deal of the Year Over $250 million, Private Equity Deal of the Year Over $500 million to $1 billion, and Cross Border Deal of the Year Over $500 million to $1 billion.

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Affiliate announcement - Acquired by IBG 2006

In 2000, the affiliate industry was a highly fragmented space and at the time program directories were a requirement of a strong affiliate program GTM to get in front of the affiliates in tandem with the affiliate networks. Established in 2000, AffiliateAnnouncement was proven to be the webs most comprehensive full service affiliate directory submission company. The business was a technology enabled services offering. It was first the rollup of 10 affiliate directories and finally a technology to automate the process completely along with a SaaS offering that finally completed the business. The business was sold to a publicly traded business out of the UK in 2006.


EMagazines - Acquired 2004

A retail direct to consumer website offering virtually every Magazine available, EMagazines was at the time a new concept in an emerging market. The business offered consumers and offline customers a subscription to groups of Magazines of their choice. The business was acquired in 2004 by a private party.

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Alaya labs - Aquired 2003

Alaya Labs manufactured and included an online retail business selling S-adenosyl-L-methionine (SAMe) which is a compound found naturally in the body. SAMe helps produce and regulate hormones and maintain cell membranes. People generally use SAMe to treat osteoarthritis, liver disease and depression. However, SAMe can also interact with antidepressant medications. The business used a GTM focused on osteoarthritis, liver disease and depression content and both online and offline resellers. The business was acquired by a private party in 2003. 

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Magic Shine - Acquired 2001

The business was founded by Jay Stolpestad as a solution to the low quality, battery time, and brightness of bicycle headlamps. The product, manufactured out of china, presented the market with the brightest, longest lasting battery with the smallest and lightest footprint in the industry. The business became among the most used headlamp in law enforcement and grew to over 250,000 unit sales monthly. The GTM was a content marketing strategy to specific industry thought leaders, combined with a strong “insider” feedback loop. Acquired in 2001 by the manufacture in China, the business now operates under the name MagicShine.

all-travel-insurance.webp - Acquired 2001 offered the first online travel insurance comparison website with the ability to purchase policies online in realtime. The business included not only the resale of current insurance offerings but its own policies the business had underwritten specifically for AllTravelInsurance using said data. was ahead of its time using stored “data” on popular policy specifics and restrictions which developed extremely profitable policies for the underwriting carrier and the right coverage for the insured. The business was acquired by the insurance carrier in 2001.

all-passports-visas (1).webp - Acquired 2001, an additional spin out to the travel insurance business, was built with an optimization of the travel insurance customer base and an integrated partnership with affiliate marketing. The technology we built and the services that were provided by an offline Passports & travel visa service business was revolutionary for the time. The business offered the fastest turnaround time and the customers did not even need to leave home, a huge competitive advantage. The business was acquired in 2001 by the service partner and became the backbone of their new online service offering. 


allcurrencyexchange - Acquired 2001

Spinning out of the travel insurance business, AllCurrencyExchange utilized and optimized travel insurance customers. An international partnership with a Foreign Exchange business in the UK provided the technology and services to offer a range of local currency prior to a travelers trip at better rates than what would be available in airports or banks. The business utilized affiliate marketing programs built in the travel insurance business and partnerships with cruise lines and transportation services like Super Shuttle. The business was acquired in 2001 by Advanced Data Systems in 2001.


Vision environmental solutions - Acquired 1997

Vision Environmental Solutions was founded based on a product designed by Dr Howard Warren, the creator of Applied BioTechnology. The company focused on the remediation of hydrocarbon in municipalities and commercial food service businesses. The product is a highly concentrated microbial ecosystem containing specialized natural microorganisms selected for maximum efficiency in the biodegradation of organic contaminants in industrial and municipal wastewater, supplied as a dry fine granule, packaged in water-soluble bags. The business was merged into a new entity and then carved out to be acquired by Epicore BioNetworks in 1997, which was then acquired by Neovia Group.


American Federal Lending - Acquired 1994

In 1994 American Federal Lending, a direct lender to the real-states industry, provided lending to real-estate agents, and borrowers backed by real-estate. The business was founded with the concept of a more customized approach and GTM focused on aggregators of borrowers. I was bought out in 1994, however the other co-founders stayed in to continue the companies journey.

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