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Multifamily Legacy Podcast

Dec 17, 2019

Going from more than 1,500 passive investments to actively closing more than 170 units and a goal to reach 50 million assets under management in the next year—that’s just the tip of the iceberg.  

Today’s guest is Gary Lipsky, CEO and founder of Break of Day Capital. Knowing how to manage people, having a steady hand, and being a solutions-oriented person led him to the multifamily space. 

Topics on Today’s Episode:

  • Perfect Storm: Applying years of experience, skills, and lessons learned led Gary to multifamily space
  • Pull the Trigger: Education and partnerships provide time and money to invest personally and professionally, in owning multifamily properties 
  • Meetup Host: What happens? What do you learn from others? And why do others seek Gary’s advice?
  • Build in Buffers: Rates and terms can change, nothing’s perfect and things can always go wrong
  • Don’t Chase Deals: Stay patient, steady, and true to your numbers to get deals
  • CapEx Negotiation Needed: Who’s going to pay? Who’s fault is it? 
  • Realistic vs. Best Case Scenario: Over-perform rather than under-promise; give investors what they expect 
  • Raising Capital: Email list, meetups, Webinars, and meaningful relationships 
  • Multifamily Game: Too good to be true? Find, educate, understand, and invest to overcome fear
  • Due Diligence: Take action, don’t work in silo, and partner with others; every deal looks sexy, get to know operator and go beyond memorandum before investing  

Links and Resources Mentioned:


“Everything I have done in the past has led up to this moment. The lessons learned, the mistakes, all the hard work has brought me to this point.” Gary Lipsky 

“Knowing how to manage people, having a steady hand, and kind of being a solutions-oriented person really led me to multifamily.” Gary Lipsky 

“Deals, money, people, resourcesthose are all the things that show up at meetups.” Corey Peterson 

“Dealing with a seller who is a pain in the ass from the beginning, it’s not going to improve.” Gary Lipsky 

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