April 15, 2025
Episode 217 – Jeremy Delk – Failing His Way to Success
“Everything works out for a reason; you’ve got to keep moving forward and changing your perspective on failure. I do not believe anything good happens to you or anything bad happens to you. I think life’s a series of events and it’s the actions and the emotion that you apply to those events that will later determine if they were a good thing or a bad thing.” – Jeremy Delk
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- 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.
- Show Notes
- [00:42] Patrick introduces his next TEDM guest Jeremy Delk.
- [02:00] Jeremy and Patrick get going on their conversation where Jeremy defines what he’s currently doing, how his early career shaped what he did not want and inspired his move to do his own thing.
- [05:38] Two major fork in the road moments that were catalysts for Jeremy’s path to Wall Street which ultimately led to big changes and big results.
- [12:24] Patrick and Jeremy reflect on standing in support to help our children avoid the mistakes we’ve made and the reality that the lessons we learn are what make us who we are!
- [21:15] Patrick shares a story of a trust funder and the skepticism that they’re met with.
- [22:21] Venture capitalist vs. angel investor. How Jeremy works it and his industry criteria.
- [26:36] Jeremy describes his more ideal types of business start ups.
- [28:34] Jeremy’s top 3 tips for a venture capital pitch!
- [32:57] Delegation for elevation. Jeremy offers his perspective on putting time into what we’re good at.
- [38:40] Walking away from $600 million. Jeremy shares the story of why he walked away from the deal – part 1 and 2. Life doesn’t happen to us; it happens for us.
- [44:41] Action and forward momentum are our saviours. Jeremy’s certainty is that his success is thanks to the failures he’s made. He takes action which doesn’t always work out, but he keeps moving forward. Just take one step. There are only two scenarios – it will either work or won’t. Both produce good information. How big would you dream, if you knew you could not fail.
- [49:54] The quality of our life, is a reflection of the quality of the questions we ask ourselves. “What if I fail?” is not the best question in Patrick estimation, “what happens if it works” helps our brains get creative. Jeremy takes another step or multiple steps to inquire “WHY do you want this?” Resources are great, but it can’t be the only reason why.
- [54:00] Passion and unwavering, authentic belief in your product or service is the secret sauce in sales.
- [55:44] It’s true, the first million is the hardest to make. Jeremy offers both his observation of how other people are wired for financial uplevelling and how he’s wired. The difference is not surprising and there is always another level (stay out of comparison though.)
- [61:58] Patrick shares the “King of Spain” story.
- [63:53] Jeremy shares a nugget of coaching wisdom around the question “what will other people think of me?” Jeremy strives to be the best, most authentic version of himself, but does not care what people think of him. Embracing vulnerability and working with it in his coaching practice is far more impactful and fulfilling.
- [69:58] Wrapping it up with the rapid fire. Apple or Android; diverse musical tastes; favourite movie; room-desk-car; favourite swear word; message at the pearly gates.
- [73:09] Jeremy’s gratitude.
- Selected links and people mentioned from this episode:
- Jeremy Delk
- Die With Zero by Bill Perkins
- Without a Plan by Jeremy Delk
- Connect with REIN Canada
- REIN Canada
- [email protected]
- REIN Channel
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