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Entrepreneur Weekly


Jan 13, 2024

 Alan welcomes Jonathan Beskin, a serial entrepreneur and bestselling author of "The Least Likely Millionaire." The book tells the story of how Jonathan overcame crippling anxiety, toxic parenting, and a total lack of support to start and build a wildly successful company, despite everyone telling him his ideas would never work and that he would be a failure. The book is a triumphant memoir highlighting Jonathan's journey, including the ups and downs, and providing actionable advice to help other entrepreneurs.

 Jonathan also owns Singlesswag.com, worth 80 million dollars in subscription boxes. Aspiring entrepreneurs overcoming challenging obstacles can hopefully find inspiration in his story and become "least likely millionaires." During the interview, Alan asks Jonathan about three points of success. The first point is the concept of healthy obsession and how one can channel negative experiences into positive energy.

Alan welcomes Raj Jana, the CEO of Liber8. Liber8 is a company that develops programs to help people overcome emotional and childhood trauma, as well as any limiting beliefs that prevent them from living a meaningful and authentic life. The company's mission is to remove any barriers that may be stopping people from achieving the things they desire.

Raj shares his personal experience of burnout while building his first company in 2019, at the age of 27. He worked tirelessly, hustling day and night, until he reached his breaking point. He realized that his need to prove himself, his obsession with making money, and his constant busyness were all rooted in trauma. He understood that if he was living his purpose, he wouldn't have been burned out. Instead, he would have felt more alive.

After selling his company, Raj faced even more challenges. He felt purposeless and lost, and his relationships were in shambles. He realized that he needed to work on himself and his relationships. He had to address his trauma with being vulnerable and intimate in partnerships. He had to learn how to connect and be seen.

Raj's experience was both liberating and a trap. He had the resources to address his issues, but he also felt lost and directionless. Raj's story is a reminder that success doesn't always bring happiness and that it's essential to work on oneself, both personally and professionally.

Raj Jana emphasizes the importance of having a clear vision for your company, which includes how much money you're making, how your customers feel, what your products are, and what your brand is. By inspiring people with a vision, you can get talent to show up in ways that no paycheck will. 

Another important tip from Raj is to empower your team by delegating tasks. Remember that a 90 is still an A, so relax your standards and delegate to open up your capacity for more support. This is the ultimate entrepreneurial journey – letting go of control.

  • [00:00:00] The Least Likely Millionaire
  • [00:07:32] Triumphant Memoire
  • [00:12:30] Actionable Advice
  • [00:19:50] Liber8 with Raj Jana
  • [00:28:37] Tools and Resources
  • [00:36:24] Let Go!