Jason Bordainick started his first company from a dorm room at the University of Virginia. Off Campus Partners became the nation's largest online marketplace for student housing and was eventually acquired by CoStar. That success gave him credibility, momentum, and the confidence to take on something harder.

In 2010, he and his childhood friend Andy Cavaluzzi decided to build a business in affordable housing preservation. Expertise, relationships, and regulatory fluency created steep barriers to entry in the space. They had vision but no track record in the asset class, no institutional backing, and no family real estate firm to lean on. For three and a half years, they submitted proposals, chased deals, and came up just short. That grind built the discipline and partnership that would eventually shape Hudson Valley Property Group into one of the leading platforms in the space.

In this episode of The Dealmakers' Edge, Aaron and Jason discuss what it takes to break into a market with high barriers to entry, how to build institutional trust from scratch, and why consistency and execution matter more than having all the answers upfront. Jason shares lessons from proving out a model, earning credibility deal by deal, and leading a business that does well by doing good.

2:57 - Starting Off Campus Partners from a dorm room and winning a business plan competition

4:57 -Teaming up with childhood friend Andy Cavaluzzi to start Hudson Valley Property Group in 2010

6:48 - Understanding capital-A Affordable housing and the role of Section 8 and LIHTC programs

11:49 - Starting with $5,000 and $10,000 checks and compounding investor trust

14:52 - Values-first leadership and how you do anything is how you do everything

16:21 - Using discipline and AI to screen projects and deploy capital at scale

18:16 - Managing adversity and the mental challenges of entrepreneurship

21:14 - How adversity strengthens partnerships and builds equal commitment

23:35 - Career advice for the next generation and the value of specialization

Mentioned In Leading the Future of Affordable Housing with Jason Bordainick

Hudson Valley Property Group | LinkedIn

Jason Bordainick on LinkedIn

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