In this episode of Lawsuits & Lessons, hosts John Fagerholm and Steve Cooper welcome longtime friend, attorney, and entrepreneur Jesse Rosenblatt for a wide-ranging conversation about reinvention, resilience, and building a life with intention.
With more than 20 years as an executive, creative strategist, and business and legal affairs consultant, Jesse has worked at the intersection of entertainment, media, and technology, helping accelerate ventures and close complex deals totaling over $5 billion. His career includes work with major companies such as Netflix, NBCUniversal, Facebook, Disney, Apple, Sony, Amazon, and Google, always focused on creating non-zero-sum outcomes where everyone wins.
But Jesse’s story goes far beyond big deals. He opens up about leaving traditional corporate paths, navigating entrepreneurial failures, and redefining success outside of titles and paychecks. The conversation explores how curiosity, stoicism, mentorship, and self-trust play a critical role in long-term fulfillment, especially for entrepreneurs and creatives.
John, Steve, and Jesse also dive into digital nomad life, the realities of entrepreneurship post-pandemic, and why valuing your time, energy, and environment may be the most important business decision you ever make. Along the way, Jesse shares how philanthropy and purpose-driven work remain central to his life, including his nonprofit Give Something Bike, which provides new bicycles to foster youth during the holidays.
The episode closes with a forward-looking discussion on emerging technology, as Jesse discusses his role as COO of GEN-X, an NFT and Web3-focused community designed to onboard millions of Gen-Xers into Web3 through education, pop culture, and nostalgia.
What You’ll Learn in This Episode
- Why entrepreneurship often begins with dissatisfaction, not ambition
- How failure becomes a competitive advantage over time
- The mindset shift required when moving from employee to founder
- Why environment, location, and lifestyle matter more than people admit
- The dangers of DIY legal work and over-reliance on AI tools
- How mentorship shapes better decisions in business and life
- Why fulfillment, not just success, should be the real goal
Hosts:
John Fagerholm — Employment Defense Attorney
🌐 defendmybiz.com
Steve Cooper — Comedian & Podcaster
🌐 coopertalk.net
Guest:
Jesse Rosenblatt — Attorney, Entrepreneur & Coach
🌐 Legal & Consulting: jesserosenblatt.com
🌐 Coaching: coachmejesse.com