Gregory Shepard

#411: With No Struggle, There is Neither Story Nor Success

#411: With No Struggle, There is Neither Story Nor Success

Napoleon Hill once famously said, “Strength and growth only come through continuous effort and struggle.”

While that may read well on a motivational poster, we go out of our way to avoid conflict and strife.

Or as Winston Churchill put it, “If you’re going through hell, keep going.”

But it seems inevitable that through our most difficult moments is where we grow the most.

Today’s guest knows this better than most.

Gregory Shepard, a tech superstar who has experienced 14 liquidity events, was diagnosed with seven neurodivergent conditions including autism, synesthesia and dyslexia.

But he believes these so-called deficits are actually his superpowers that have enabled his remarkable success, including selling two of his start-ups to eBay as part of a $925 million transaction. Gregory Shepard says he and folks like him simply see the world a little, or a lot, differently than the rest of us.

“As a Nerodivergent autistic, my story applies to all those who struggle which is all founders. I use my stories of struggle and success to bring knowledge to the founders.”

With a strong background in computer science, Shepard established Startup Science in 2010 to provide business operating support to startups. His groundbreaking Business Operating Support System (BOSS) has transformed the way startups streamline their operations.

Through BOSS, startups gain access to comprehensive tools and services, empowering them to optimize resources and achieve rapid growth.

Under Shepard’s leadership, Startup Science has become a trailblazer in the startup ecosystem, helping numerous ventures overcome operational challenges.

Shepard is also known for his mentorship and advocacy for young entrepreneurs, sharing his expertise at industry conferences. His vision and dedication continue to shape the entrepreneurial landscape, driving the success of startups and fostering innovation.

He is a ForbesBooks author who has also written over 100 articles published in 25 national and international publications. A TEDX speaker and keynote speaker for universities, associations and conferences worldwide, his talks inspire the masses. And he is the host of the Forbes Radio ‘Meet The BOSS‘ podcast.

Discussed in this episode:

  1. How did you go from selling rattlesnakes to make money in your teens to selling to eBay for over $900 million.
  2. Why does every start-up need to go through 7 phases when building a business to sell?
  3. What should all business owners learn from Elon Musk/Tesla?
  4. How improving entrepreneurs’ ability to scale business can change the world?


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