EP 51: Why Cash Flow and Systems Win in Real Estate with Gary Jonas episode artwork

EPISODE · Nov 4, 2025 · 32 MIN

EP 51: Why Cash Flow and Systems Win in Real Estate with Gary Jonas

from Sky's the Limit with Mike & Ryan · host Mike Doherty & Ryan Deasy

In this episode of Sky’s The Limit, host Mike Doherty sits down with Gary Jonas, Owner and CEO of The HOW Group, a full-service investment firm with over $500 million in assets under management.Gary shares how he went from buying his first home in his 20s to building one of Philadelphia’s leading real estate investment and development companies. He also explains how The HOW Group navigates today’s market with a long-term, cash flow focused investment strategy. Gary discusses the importance of local market knowledge, strong systems like EOS, and communities like GoBundance that have supported his personal and professional growth.Tune in to learn practical real estate strategies, market insights, and the mindset that helped Gary grow from 10 rental properties to managing a $500M portfolio.🔗 Useful Links:• Our Website: https://www.skytreeinvestments.com/podcast   • Find us on Social Media: https://linktr.ee/skysthelimitpodcast   • Our Producer: https://capturetheconcept.com  Connect with Gary!Gary's Email: [email protected] Gary's LinkedIn: https://www.linkedin.com/in/gary-jonas-371288a/  The HOW Group Facebook: https://www.facebook.com/thehowgroup The HOW Group Instagram:  https://www.instagram.com/thehowgroup The HOW Group LinkedIn: https://www.linkedin.com/company/thehowgroup/ Website: https://www.impact-howgroup.com/investments #RealEstate #Investing #Multifamily #SingleFamily #RealEstateDevelopment #InvestmentSubscribe to our YouTube channel to watch our podcast and other related content in video form! https://www.youtube.com/@skysthelimit.podcast

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In this episode of Sky’s The Limit, host Mike Doherty sits down with Gary Jonas, Owner and CEO of The HOW Group, a full-service investment firm with over $500 million in assets under management. Gary shares how he went from buying his first home in his 20s to building one of Philadelphia’s leading real estate investment and development companies. He also explains how The HOW Group navigates today’s market with a long-term, cash flow focused investment strategy. Gary discusses the importance ...

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EP 51: Why Cash Flow and Systems Win in Real Estate with Gary Jonas

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