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April 29, 2025 29 mins

In this engaging conversation, Lee Rotenberg shares her entrepreneurial journey, emphasizing the importance of fun and authenticity in her work. She reflects on the challenges of defining success and happiness, the lessons learned from founding and selling companies, and the significance of being present and true to oneself. Lee discusses how her recent LinkedIn post about prioritizing fun in her next career chapter resonated with many, and explains why internal success matters more to her now than external validation. The conversation highlights the evolving nature of entrepreneurship, from the excitement of early-stage creation to the challenges of scaling and fundraising, offering valuable insights for anyone navigating their own path to fulfillment.

Key Topics:

  • Prioritizing fun and authenticity in your career decisions
  • Redefining success beyond external validation
  • Finding happiness through presence and mindfulness
  • Navigating the emotional roller coaster of entrepreneurship
  • The joy of early-stage business building versus the challenges of scaling
  • The drawbacks of fundraising for founders
  • Learning how to evolve and adapt throughout your journey
  • The importance of taking action on ideas rather than overthinking
  • Moving from ArtSetters to Ivy to Clay to Hulken

Notable Quotes:

  • "This next era of my work chapter will be one where I'm essentially focusing more on fun."
  • "I want to have delight in my day to day more than I want to have success."
  • "Being successful is being happy... being very present and not trying to think about what is next."
  • "When you're able to truly just be you and not worry about the external voices or external wants, that makes me invigorated."
  • "If you want something too badly, it rarely happens. When you're living your best self, you become a magnet for all different areas of your life."
  • "People's biggest mistake is they wait to launch or they're overthinking the steps. You need something very shitty in a sense, because that's the only way it's going to get better."
  • "Fear can still stay there and you can do it while you're scared."

Lee's Powerful Question: "What's the why behind what you're doing? Ask yourself the why and be really honest with yourself on that answer."

Resources Mentioned:

 

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