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Today, we are joined by Brian Chupek, who dove straight into the corporate world with Morgan Stanley after graduating college. He rose the ranks working in securities lending. However, after two years, he knew something was missing. Brian was grinding from 7am-7pm doing the same thing day in and day out. He started planning and saving to be able to eventually strike off on his own. After three and a half years, he quit his full-time job with no plan as to what was next.

Brian knew he wanted to bet on himself and took three months off to figure out what would allow him to control his schedule and put a higher priority on the relationships in his life. Inspired by his mother, who invested in real estate to support herself, Brian chose to become a real estate agent. He knew the first year would be difficult, but he focused on learning from and partnering with others that had already had success in that field. He also worked on creating system to manage his time and hold himself accountable.

Brian has been able to scale his real estate business over the past three years while starting to dive into different business opportunities as well. He did not want to solely rely on selling for his only revenue stream. So he has started getting involved in property management, commercial real estate, and investing in real estate properties. He wants continue to diversify from the selling side to the buying side over the next 3-5 years.

If you live in the Baltimore area and are interested in Brian’s services, please reach out to him at or on LinkedIn!

Check out the conversation as we dive into the following:

  • How he couldn’t envision a long career in the corporate world
  • Why control over his schedule became his biggest “non-negotiable”
  • Why he believes in work-life integration not work-life balance
  • How he mitigates risk by working with other partners
  • How he focuses on education and getting 1% better every day

Listen to Brian share his story and get inspired with his amazing advice to people thinking about following a similar path. Check out the full conversation on YouTube or Spotify by clicking the links below.

Listen on Spotify

Listen on Apple Podcasts

Know someone who should be on Why I Quit? We’re looking for all types of stories and people to feature at the top of the show. To nominate yourself or someone else, email and tell us your name, where you’re from and what you want to talk about.