With over 25 years and nearly $2.5B in closed deals, Jim Small helps real estate founders lead like seasoned CEOs. Whether you're aligning your executive team, raising institutional capital, or building systems that scale—you'll get real frameworks, direct guidance, and measurable results. Join the CEOs who are leading smarter, growing faster, and building businesses worth investing in.
Years of Real Estate Leadership
Executives Coached
Portfolio Value Managed
Industry Awards
Tailored coaching solutions designed to address the unique challenges faced by real estate leaders and entrepreneurs.
Align your executive team with systems that drive growth and execution. Perfect for real estate CEOs who need structure, accountability, and team-wide clarity.
Raise $30-$250M using proven frameworks built by a real estate insider. Designed for operators ready to pitch, structure, and close institutional capital.
Real estate-focused coaching with no fluff—just clarity, structure, and execution. Built for founders navigating scale, team complexity, and capital strategy.
Hear from real estate leaders who have transformed their businesses through our executive coaching programs.
Managing Partner at Workforce Partners
“Working with Jim has completely challenged how I think as a CEO. He brought fresh and meaningful ideas, helped me prioritize the right levers for strategic growth and avoid costly missteps. In just a few months, we refined our investment strategy, overhauled internal priorities, and created a level of momentum I hadn’t experienced in years. Jim’s frameworks aren’t theoretical—they’re built from real-world battles, and it shows. I’ve made sharper decisions, moved faster, and built a leadership muscle I didn’t know I had.”
Chief Executive Officer at CAPREIT
“Jim’s advisory around capital formation was nothing short of transformative. We wanted to develop a new Fund strategy but our team was too busy and lacked the critical market knowledge to bring this idea to fruition. His insights into institutional capital dynamics and long-term alignment is helping us secure partners who actually fit our unique vision. This wasn’t just about raising money—it was about raising the right money.”
Land Investor
“We thought we understood capital raising—until we worked with Jim. He immediately pointed out structural inefficiencies, revamped our pitch strategy, and gave us tools that elevated our credibility in front of institutional investors. Within a quarter, we secured a strategic anchor LP and built a pipeline of aligned capital partners. Jim brings precision, speed, and serious market intelligence to the table.”
Founder & CEO of Harrington
“Working with Jim gave me the clarity and conviction I needed to scale with intention. As a CEO, you don’t often have someone who can challenge your thinking, offer proven frameworks, and still operate with full alignment to your mission—but Jim does exactly that. The impact was immediate—and lasting.”
CEO, Founder at Gryphon Financial Partners
“When we started working with Jim, we had the ambition to scale but lacked the structure to support it. Jim’s deep expertise in founder-led businesses and alternative investments made him the perfect fit. He's helping us align our leadership team, implement the right systems, and shift from reactive to strategic. Jim isn't just helping us grow—he's helping us grow the right way.”
Real Estate Developer
“Jim’s team coaching brought a level of alignment we’d never had before. Our leadership team is evolving quickly toward understanding the vision, owning their role in scaling the firm, and collaborating in a way that actually moves the needle. Our off-sites have gone from long lists of busy work to action-packed, measurable planning sessions. We’re more focused, more united, and better positioned for growth than ever.”
President at LGE Design Build
“Jim took a fresh look at our capital formation approach. His engaging questions helped me refine our Fund mechanics to ensure clarity and alignment with our internal stakeholders as well as our institutional investors. The impact was immediate as he didn't have just theories to share but actual real-world examples and experiences. His insights into sponsor economics alone have the potential to multiply long-term GP upside.”
With over 25 years as a real estate operator and capital strategist, Jim Small has led nearly $1B in transactions across complex markets. His coaching isn't theory—it's grounded in firsthand experience navigating growth, raising institutional capital, and building high-performance teams.
Jim’s coaching goes beyond generic business advice. He delivers real estate-specific strategy, leadership alignment systems, and capital formation frameworks designed to help ambitious CEOs scale with clarity, confidence, and results.
Sign Up for Executive CoachingTake the first step toward transforming your real estate business. Schedule a complimentary strategy session to discuss your goals and challenges with Jim.