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Gregory Shepard        

Co-Founder BOSS Capital Partners & BOSS Startup Science; Serial Entrepreneur; Neurodiversity Advocate

Part Steve Jobs, Part Forrest Gump, All-American Dream.

Gregory Shepard has built and sold 12 businesses in BioTech, TransitTech, AdTech and MarTech. He is a Forbes Book Author and contributor and has been featured or quoted in publications like Fortune, Entrepreneur, The New York Observer, The DEAL and Thrive Global. A recipient of four private equity awards for transactions between $250M to $1B, Shepard has appeared on TV, Radio, and popular Podcasts. He has also been a TEDX and Keynote speaker at multiple universities and conferences worldwide.

As a founder at BOSS Capital Partners, Shepard co-leads a global investment syndicate that focuses on series seed technology businesses that prefer operational expertise and guidance to achieve rewarding, capital-efficient outcomes. Their most recent success story is Delerrok, which was acquired by Cubic Transportation for $48M in just under 3 years of initial investment as a result of implementing Shepard’s proprietary BOSS (Business Operating Support System) Methodology and Framework. BOSS–an open-source business operating system formulated by his 20+ years of entrepreneurial experience and investor expertise–was developed to empower entrepreneurs and increase the overall startup success rate.

Humble beginnings molded by struggles with neurodivergence and poverty haven’t stopped Shepard from becoming the successful entrepreneur, author, and philanthropist he is today. His success story of overcoming obstacles is what drives him to support young entrepreneurs looking to spark positive change in the world around them, spreading his message of “Altruistic Capitalism”. From growing up with very little, to navigating a world not built for those with neurodivergencies, Shepard continues to be one of the most recognizable examples of how fearless optimism and steadfast determination can guide any intelligent and determined young professional toward success.


Understanding Personality Types Will Help You Develop Your Tech Startup's North Star
As an entrepreneur, you're likely keenly aware that there are many different techniques, strategies and tactics for launching a new tech company, acquiring a company, staffing that company, launching new products and creating user stories. Cognitive bias can affect the success of these activities.
Does Your Potential Acquisition Utilize A System Of Engagement?
As an entrepreneur looking to build or buy a business, one of the most important things to consider is the business' primary method of operation. Does the business operate based on system of record (SoR), or does it operate on system of engagement (SoE)? And how will these two very different methods of operation affect the coming-together of two different companies in terms of operational synergies and customer retention?
w Remote Work Can Transform Smaller Cities
In late 2017, Amazon announced plans to build a second headquarters, sparking a fiercely contested municipal beauty pageant as scores of cities vied to attract the tech giant. One community in Arizona sent Amazon a 21-foot cactus; another in Georgia pledged to de-annex 345 acres, giving Amazon room to build its own private city. The eventual HQ2 winners, New York City and Arlington, Virginia, jointly pledged to hand over $2.4 billion in tax breaks, cash, and other incentives in exchange for the privilege of hosting Amazon's offices.

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