Tim Beyers, a Motley Fool analyst, dives into how Apple's Fitness+ is becoming a headache for Peloton, thanks to its strategic pricing and incremental upgrades. Meanwhile, Jason Moser sheds light on Boston Omaha, a versatile small-cap holding company with interests in billboards and broadband. The conversation highlights Apple's ability to maintain prices for new iPhones while expanding its ecosystem, all without compromising on innovation in products like personalized AirPods. Leadership styles and investment strategies round out this engaging discussion.