Thomas O'Brien is the Managing Partner and Chief Executive Officer of The HYM Investment Group, LLC. HYM is currently leading the development of over twenty (20) million square feet of mixed-use development in Greater Boston, including the following notable and complex projects: Bulfinch Crossing (the redevelopment of the Government Center Garage), Suffolk Downs, and Parcel 3 in Roxbury. Prior to HYM, O'Brien served as a Managing Partner for JPI, a national developer and owner of multifamily communities, and as a Managing Director in Boston and New York for Tishman Speyer, one of the world’s leading real estate firms.

O'Brien also led the Boston Redevelopment Authority as its Director and Chief of Staff, overseeing the development of over 12 million square feet of projects in Boston, from 1993 to 2000. O'Brien has served as Chairman of The Greater Boston Real Estate Board and is Vice Chair of the Board of Overseers of The Anti-Defamation League of New England, which awarded O’Brien its Abraham Joshua Heschel Interfaith Relations Award in 2016.

In 2011, Governor Deval Patrick appointed O’Brien to the Board of the Massachusetts Housing Finance Agency. In 2016, Mayor Martin J. Walsh appointed O’Brien to the Board of Trustees of the Rose F. Kennedy Greenway Conservancy and in 2024 Governor Maura Healey appointed him to the Board of The Rose Kennedy Greenway Conservancy.

He also serves as a Board Member of the Pine Street Inn, Project 351 and the American Repertory Theater at Harvard University. O’Brien is a graduate of Brown University and Suffolk University Law School and is a member of the Massachusetts Bar.

Throughout the discussion, themes of resilience, strategic vision, and community impact are highlighted. O'Brien elaborates on his firm's focus on developing high-impact projects situated near transportation hubs, transforming urban landscapes while catering to market demands. Navigating economic fluctuations, seeking opportunities in undervalued sectors like office spaces, and maintaining transparency with partners are key strategies shared by O'Brien in realizing ambitious real estate objectives.

Key Takeaways:

• Vision and Strategy: O'Brien emphasizes the importance of a long-term, community-focused vision when selecting projects, considering both investor interests and regional development goals.
• Navigating Challenges: Highlighted are strategies to overcome economic hurdles, such as rising interest rates and building costs, while keeping projects on track.
• Teamwork and Values: O'Brien stresses building a strong team grounded in integrity and shared values, crucial for navigating the complexities of large development projects.
• Resilience in Business: Through his personal and professional journey, O'Brien underscores the ne

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Gary Kerr is the Senior Managing Director at Greystar, where he is responsible for managing new development projects and expanding the development pipeline in the Northeast region. With over 30,000 employees and $79 billion in assets under management, Greystar is recognized as the largest owner, operator, and developer of multifamily housing worldwide. Kerr has played a significant role in the company's growth, focusing on fostering relationships with capital partners, team development, and revenue generation strategies.

Kerr shares insights into the importance of networking, navigating the complexities of development projects, and how Greystar maintains its leadership in the market despite industry challenges, like its modular construction initiative. Kerr elaborates on his personal career journey, shedding light on the critical skills needed to excel in real estate development and the importance of being adaptable, innovative, and a proactive problem solver.

Key Takeaways:

• Networking and Relationships: Gary emphasizes the importance of building genuine relationships over just networking, especially within your peer group and immediately above you.
• Navigating Market Entry: By leveraging Greystar’s breadth of experience and data, Gary explains how they enter and succeed in challenging markets like Everett, Massachusetts, by identifying untapped potential and scalable opportunities.
• Innovative Construction Methods: The discussion covers Greystar's push into modular construction with Modern Living Solutions, highlighting its potential to reduce costs and accelerate timelines in real estate development.
• Growth and Opportunity: Growth isn't just a goal, but a means to provide value and innovation in their projects.
• Crisis and Adaptation: The housing crisis in Massachusetts is dissected with a focus on practical solutions and strategic foresight to address long-term challenges in housing affordability.

Notable Quotes:

1. "Growth provides opportunity. So if you want to maintain the best people in the market, you have to continually create new opportunities for them."
2. "Be the most valuable person in the room you can, and all the success, promotions, all those things will just naturally follow."
3. "The better job is looking for a better you. It doesn’t happen the other way around."
4. "You solve the problems that no one else wants, and that's how you get ahead."
5. "It's important to have the ability to innovate and define success singularly across all your teams."

Resources:

• Greystar Official Website
• The Psychology of Money by Morgan Heisel - A recommended read by Gary Kerr for understanding money management an

Thank you so much for listening and thank you for joining the Design Development community. Don't forget to subscribe to hear about the latest episodes dropping every Wednesday. If this episode resonated with you, share it with a friend.

Our goal is to help people in the industry identify opportunities for growth by sharing the journey of top performers. There is no one path. Success isn't a straight line. There is something to learn from everyone's story. Let's go!

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As listeners prepare to enter 2026, this episode offers a thought-provoking discussion navigating the often challenging interplay between career ambitions and personal life, with the goal of finding contentment in current paths while still striving for success.

This week’s episode explores the balance between pursuing professional goals and maintaining healthy relationships with family and friends, with a warning against subconscious comparisons and ego-driven decisions pulling focus away from real values. By setting constraints on time allocation and problem-solving strategies, the conversation emphasizes self-awareness and disciplined action. Success in career and personal life doesn’t require sacrificing one for the other. It requires smart scheduling and prioritizing what truly matters. The episode closes as a grounded exploration of how awareness and long-term thinking sharpen decisions and drive personal fulfillment.

Key Takeaways:

• The balance between career ambition and personal life is possible without sacrificing meaningful relationships or well-being.
• Self-awareness and disciplined action are key to achieving both professional and personal success.
• Identifying the right problems to solve is crucial to avoiding wasted effort and addressing root causes rather than symptoms.
• Long-term thinking helps to improve short-term decision-making and can lead to greater contentment and success over time.
• A commitment to lifelong learning is essential for uncovering blind spots and enhancing personal growth.

Notable Quotes:

1. "Finding content in who you are, the path you're on, the goals you have, and really the life that you're building."
2. "You can advance your relationship with your kids, your relationship with your friends, your relationship with your spouse and pursue career goals."
3. "You need to set constraints on your time and how you're allocating those across the areas of your life."
4. "The root to all of those challenges we face in life is the root to constant pursuit of learning."

Thank you so much for listening and thank you for joining the Design Development community. Don't forget to subscribe to hear about the latest episodes dropping every Wednesday. If this episode resonated with you, share it with a friend.

Our goal is to help people in the industry identify opportunities for growth by sharing the journey of top performers. There is no one path. Success isn't a straight line. There is something to learn from everyone's story. Let's go!

Leave your thoughts in the comments and reach out if you want to be a valuable guest on the show!

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Find out more at https://h-o.engineering/podcasts/