Unlocking Success: A Journey from Tennis Courts to Boardrooms with Gregg Hill, Co-Founder of Parkway Venture Capital

“I’ve always been super locked in and a little crazy. But it’s made me one of the best tennis players in the world, and now I’m on track to be one of the best VCs in the world, maybe ever.”  

Gregg Hill, Co-Founder of Parkway Venture Capital and accomplished entrepreneur, was the keynote speaker for Crummer’s 2024 commencement ceremony. His career spans from tennis success to groundbreaking investments, emphasizing vision and innovation. As managing partner, he’s led deals and introduced transformative AI software, shaping global industries and leaving a lasting impact. 

Gregg began by stating that his life path isn’t textbook. He comes from a small town in North Carolina where few people leave, and there was little of his beloved sport, tennis. He was born to teenage parents with little resources. At eight years old, he left home to live and train with Coach Nick Bollettieri to become a professional tennis player. “I desperately wanted to be the best. It was a pressure cooker. There were a lot of expectations on me, and I had to be perfect all the time.” He was required to hit 1,000 balls every day, improving his mental toughness. His life became about discipline and achieving perfection at a young age instead of having a normal childhood. He emphasized that dreams require sacrifice and can often lead down a lonely path.  

When he was on the cusp of breaking into the professional rings, disaster struck. Gregg was in a devastating car accident that ended his dreams of playing tennis. He had to work through physical and emotional pain for quite some time, but he realized, “hitting rock bottom has the best view for figuring out your next move.” He decided to pivot and took all the skills he learned—focus, discipline, an intense drive to win—and applied them in a new realm, business. He became determined to dominate the world of startups, fueled by grit to rewrite his future and invest in himself.  

Gregg offered a playbook for achieving dreams in order to invest in oneself and become the next big thing. Here is what he emphasized: 

Mental Toughness: Sacrifices Today, Success Tomorrow

The world is full of distractions, and it takes laser focus, mental toughness, and delayed gratification to be successful. You need to have the ability to make decisions others don’t want to make. Create a life that excites you, one that you’ve truly earned, and don’t be afraid to pave your own path. It’s also important to say no sometimes, even to fun events or invites from friends to stay focused. Gregg and his business partner, Jesse Coors-Blankenship, started then sold one of the earliest AI companies ten years ago, way ahead of its time. Today, over 20% of the world’s products are designed using their generative AI design technology.   

Lock In, Visualize, Conquer 

Gregg worked closely with Dr. Jim Loehr, a sports psychologist, who taught him that you want to be mentally prepared for every single day. Visualize what you want every day and see it playing out. This gave Gregg a mental edge for his tennis matches. Today, he still practices this technique, visualizing his future goals and seeing himself reaching those goals. It’s important to turn every obstacle into a steppingstone. The world awaits your unwavering focus; your dreams are just a series of visualized steps away. 

Every Day Perform for an Audience 

Imagine yourself stepping on a stage every single day. Gregg thrives in pressure-cooker situations with an audience watching his every move. He’s had large audiences when he played at Wimbledon, rung the bell at the New York Stock Exchange, and was featured on 60 Minutes thirty years ago when 15 million people watched. Almost thirty years to the day, Figure AI, a company in which he is an investor and board member, was showcased on the show with a world-changing humanoid robot he and Jesse helped create. Approach every day as if it is your own opening night performance, your own 60 Minutes special. Potential employers, future collaborators, and your future self are all watching. Make sure they see a performance worthy of a standing ovation.  

Surround Yourself with Visionaries 

Look for the visionaries, the disrupters, the high achievers, the risk takers. For the companies Gregg invests in, he wants a founder who bleeds ambition like the owners of Figure AI and Sandbox AQ where they are turning ideas into empires. Picking winners is paramount. Identify people crushing it in your field, build relationships with them, and learn from their triumphs and failures. They will be your mentors, your sounding board, and your inspiration. The company you keep shapes your trajectory, so invest in yourself by investing in those around you.  

Gregg wrapped up his address by encouraging the graduates to have the audacity to discover the unimaginable and to engineer the future their parents couldn’t even dream of. He emphasized the importance of embracing AI and becoming an active participant in this technology revolution. “Understanding AI is the foundation for future success.” He also discussed the game-changing potential of quantum computing and how it will unleash a new era of innovation. He left the graduates with this important point: “Happiness lies in self-achievement and feeling proud of what you’ve done.”  

We are immensely thankful for Gregg’s words of wisdom and for his participation in the commencement ceremony.  We are extremely proud of our graduates and look forward to the wonderful contributions they will make in their communities.  

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