At The End Of The Day

Can You Build a Successful Entrepreneurship Journey While Running Two Businesses at Once?

Chris Raimo Episode 52

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0:00 | 33:45

What does it really take to leave your 9–5 and bet on yourself?

Are you ready for the pressure, the uncertainty and the 3AM doubts no one talks about?


 And can you actually scale two businesses at the same time without burning out?

In this episode of At the End of the Day, Chris Raimo sits down with Darren Tompkins, founder and CEO of Vader-Rey Companies, to break down the real journey of entrepreneurship, from leaving stable employment to building multiple ventures from the ground up.

Darren shares the unfiltered truth behind scaling teams, accessing global talent, navigating failures, and why mindset and structure matter more than most entrepreneurs realize.

What You’ll Learn in This Episode

  •  How to transition from a stable job into full-time entrepreneurship 
  •  Why setting a “no turning back” date is critical for success 
  •  The reality of scaling teams using global talent and remote professionals 
  •  How to build a business that goes beyond transactional recruiting 
  •  The importance of leadership, delegation, and trust when growing a team 
  •  Why most entrepreneurs struggle with the emotional side of the journey 
  •  Lessons learned from building multiple businesses at the same time 
  •  How to stay focused without getting distracted by competitors

About Darren Tompkins

Darren Tompkins is the founder and CEO of Vader-Rey Companies, a global recruiting and workforce solutions firm helping businesses scale through elite engineering, recruiting, and remote professionals. With years of experience in recruiting and business development, Darren built Vader-Rey to challenge traditional hiring models and replace them with strategic talent partnerships.

He is passionate about entrepreneurship, leadership, scaling teams, and the future of work, frequently sharing insights to help businesses grow through smarter hiring and global talent access.

Connect with Darren

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