We recently connected with Gary Lipsky and have shared our conversation below.
Gary, thank you so much for making time for us today. We can’t wait to dive into your story and the lessons you’ve learned along the way, but maybe we can start with something foundational to your success. How have you gone about developing your ability to communicate effectively?
I developed my ability to communicate effectively by being more aware of how my words landed with others. I wasn’t very good at it and when I noticed that I wasn’t getting the reaction and results I was setting out to achieve. I realized that in order to become the leader I wanted to become I needed to think how about how the person receiving the communication would hear it. I had to better explain my reasoning and be sure to answer the questions that I would want answered if I was receiving the communication. A good communicator can get a lot more out of people because they better understand and that is a powerful thing.
Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?
I’m the Founder and President of Break of Day Capital, a boutique real estate investment firm that has done about 1/4 Billion in real estate transactions. We help busy professionals build generational wealth through passive investments in recession resistant apartment communities without the hassle of being a landlord. We provide investors with opportunities to earn cash flow, equity appreciation, and tax advantages while carefully safeguarding their precious capital. We focus on acquiring underperforming multifamily properties in high growth markets in the Southwest by implementing strong repositioning strategies to maximize value for all stakeholders.
Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?
I think the three most important qualities that were impactful in my journey have been curiosity, perseverance and vision. Curiosity to learn about the potential that this journey could provide and to never stop learning. I attend conferences and I’m part of groups that help me continue to grow and improve as a person and as a business owner. There is always room for improvement and if you have high aspirations curiosity is key. You also need perseverance. There are many obstacles thrown your way and there are good times and bad. You have to have perseverance to keep going, to get up when you have fallen. Everyone goes through adversity but no everyone gets back up and keeps going. The last quality that you need is having a vision. If you don’t have a vision, how do you know where to head to or strive for? It doesn’t mean that vision can’t change but you have to have a direction.
One of our goals is to help like-minded folks with similar goals connect and so before we go we want to ask if you are looking to partner or collab with others – and if so, what would make the ideal collaborator or partner?
We are always looking for folks to partner with. Real estate is a team sport and having passive investors, capital partners, allows us to provide passive opportunities for busy professionals while our team of experts can purchase properties with great economies of scale. Passive investors have included people that want the diversification, tax benefits, a hard asset and a hedge against inflation that real estate provides. It also allows hard working professionals to do what they do best and not have to worry about toilets, trash or tenants. Creating win win scenarios for our investors and for our residents has allowed us to grow and have a positive impact!
Contact Info:
- Website: www.breakofdaycapital.com
- Instagram: https://www.instagram.com/breakofdaycapital/
- Linkedin: https://www.linkedin.com/in/gary-lipsky/
- Youtube: https://www.youtube.com/c/breakofdaycapital

