Pickleball Strategy, Drilling & Business Lessons with Jennings Smith

Smashing Plastic hits Episode 50 with returning guest Jennings Smith from the very first guest on the podcast, for a powerful conversation about pickleball growth, drilling, strategy, mindset, and the business lessons that show up on and off the court. Coach Tommy and Jennings break down how players move past the 3.5–4.0 level, why third shot drops and dinking matter, and how smarter decision-making can change your entire pickleball game. This episode goes beyond just swinging harder. Jennings shares how intentional drilling, skinny singles, controlled drops, better footwork, and learning when not to speed the ball up have helped him level up as a player. The guys also dig into the “cliquey” side of pickleball, playing with the right level group, and why self-awareness matters if you want to keep improving. Then the conversation shifts into business, real estate, and entrepreneurship — including how pickleball strategy mirrors commercial real estate strategy. From finding weaknesses, making adjustments, and taking calculated risks, Jennings shares lessons from multifamily investing, commercial tenants, flex warehouse development, and building momentum before everything feels perfect. Whether you’re chasing 4.0, trying to become a more complete pickleball player, or looking for motivation to take the next step in business, this episode is packed with bold, practical takeaways. Watch now, subscribe, and let’s keep smashing plastic.   Follow Jennings and Unlock Your Life: Website: https://jenningssmithjr.com  Pod: https://thepodcastfactory.com/jennings-smith-unlock-your-life/  IG: https://www.instagram.com/jenningsfostersmithjr/    Follow Smashing Plastic: FB: https://www.facebook.com/SmashingPlastic  IG: https://www.instagram.com/smashingthyplastic/