Born and raised in a small town and from a blue-collar household, Jeremy always held much bigger dreams. He longed to experience the world outside his small hometown of Bardstown, Kentucky. He jumped into entrepreneurial ventures with the naivety of a child and the tenacity of a tycoon. He started day trading at the age of sixteen, learning and failing with each trade. It is this process of adapting through failures that is paramount to his success in business.

Jeremy’s knowledge and skill as a day trader helped him land a job as one of the youngest brokers at Fidelity trading institutional equities in Boston, and later in New York. It didn’t fulfill the entrepreneurial spark within him, so he decided to go out on his own creating Delk Enterprises. More than 20 years later, Delk Enterprises has holdings in biotech & healthcare, consumer brands, technology, building materials, and real estate development.

Jeremy now focuses on investing in and advising entrepreneurs through speaking. His upcoming book shares his reality of the Good, Bad, and UGLY of entrepreneurship. It serves as a not-so-subtle reminder of fundamental principles he’s learned through his journey: while great times don’t last forever, neither do the truly bad.

With so many nuggets of wisdom and lessons learned, you don’t want to miss this episode. Jeremy starts by sharing two impactful fork-in-the road moments that shaped his young life and ultimately his path to big changes and the big results he now enjoys. As a thriving venture capitalist, Jeremy describes his ideal business types and offers his 3 top tips when pitching your investment. Patrick and David have rich conversations about comparison, walking away from a $600 million exit, asking better questions and the value and necessity of the mistakes and lessons that shape who we become.

14x21: Internet Girlfriend