He starts an after school program focused on leadership development that he scales to where they were working with over 9,000 kids daily. After 16 years he sells this business and this gives him the ability and capital to get into real estate full time.

Gary Lipsky Interview

Key Points from a Full Time Investor

full time investor
Photographer: Austin Distel | Source: Unsplash
  • Has always been an entrepreneur. He would detail cars in the summer and would shovel snow to make some extra money in the winter
  • He started a restaurant delivery service while he was in college but that business failed
  • After he graduated, he started up another delivery service full time but he didn't have any real passion for the company
  • He co-produced a few low budge independent films and that was significantly more satisfying for Gary
  • While he was doing that, his wife got pregnant. So, on the side Gary started an after school outdoor leadership development company for children
  • Over 16 years, he scaled up the company to 9,000 students daily in 90 different schools
  • Started grooming the company to sell, by distancing himself from the company as a whole and giving more responsibility to his execs
  • While he was growing that company, he was also investing in real estate. He then sold the company to help boost his investing portfolio
  • Started buying and fixing up single family homes and renting them out for a few years and then selling them
  • Joined Sunroc group, which helped because it allowed him to be around a lot of like-minded people full time
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Moments of Truth Graphic
  • Who is your success role model? He doesn't look up to any one person. It's more about the balance of a happy healthy lifestyle
  • What is your biggest success? Building a 200 piece kitchen set for his daughter is his Mona Lisa. While his biggest success in business is his previous company becuase he was possitively affecting 9,000 students daily
  • What does a typical day for you look like? No two days are alike. He sets up a triage and handles the most important thing at any given time. He gets up at 5:15 a.m., tries to work out, then gets to work around 7:00 a.m.
  • What is your favorite quote? "Carpe diem"
  • What are your hobbies? Beach volleyball and hiking
  • What is the best business book you've read? Fierce Conversations by Susan Scott
  • If there was one key piece of advice you could leave our listeners with about achieving success, what would it be? Be around like-minded people as much as you can: it will add a lot of fuel to your fire

About our Guest, Gary Lipsky

Gary Lipsky Headshot
Gary Lipsky Headshot

Real Estate Experience

Gary has been a real estate investor since 2002. He runs a few real estate meet-up groups in Los Angeles and Phoenix, is a regular at real estate conferences nationwide and has been on a bunch of podcasts. He’s a personal student of Brad Sumrok, who’s group has closed $513 million in real estate in 2018. Gary is Real Estate Financial Modeling Certified. He’s also an experienced and successful business operator.

Business Experience

Gary is the Founder/President of Break of Day Capital since 2017 which syndicates real estate opportunities. They focus primarily on C Class value add opportunities in high growth population areas. Prior to that, Gary was the Founder/Co-President of arc from May, 2001 to December, 2016. He grew the company to over $12 million in revenue and over 700 employees while positively affecting over 9,000 students daily throughout Southern California.

Gary is also one of the founding Board Members of CORE Educational Services. He founded the non-profit to change the lives of under-served youth throughout Southern California in 2005. Gary was also an independent Film Producer from 1994 to 2001. He went to Boston University and graduated with a Bachelor of Science in Business Administration in 1992.