Richard Chess

Richard Chess

VA, US

Learn how to grow your business or real estate portfolio, structure deals, and maximize value before a sale. Rick Chess is a former legislator with decades of experience guiding owners through growth, governance, and strategic exits.

Rick Chess works directly with business and real estate owners to navigate the critical decisions that determine value and exit outcomes. His programs focus on growth strategy, deal structure, governance, and exit planning, giving audiences practical frameworks they can apply immediately.


Rick has:

  • Led major real estate and business transactions, including the acquisition of 50,000 apartments and 10 shopping centers
  • Raised over $100 million in equity for each of three firms
  • Advised owners, boards, and family businesses on growth, governance, and leadership transitions
  • Served as a founding NYSE REIT trustee, adjunct instructor, and legislative committee member
  • Provides guidance on capital markets, 1031 transactions, and business exit strategy


Rick’s presentations are actionable, insight-driven, and owner-focused. Audiences leave knowing how to think like a buyer, protect value, and make the strategic moves that unlock growth or a successful sale.

Rick Chess works directly with business and real estate owners to navigate the critical decisions that determine value and exit outcomes. His programs focus on growth strategy, deal structure, governance, and exit planning, giving audiences practical frameworks they can apply immediately.


Rick has:

  • Led major real estate and business transactions, including the acquisition of 50,000 apartments and 10 shopping centers
  • Raised over $100 million in equity for each of three firms
  • Advised owners, boards, and family businesses on growth, governance, and leadership transitions
  • Served as a founding NYSE REIT trustee, adjunct instructor, and legislative committee member
  • Provides guidance on capital markets, 1031 transactions, and business exit strategy


Rick’s presentations are actionable, insight-driven, and owner-focused. Audiences leave knowing how to think like a buyer, protect value, and make the strategic moves that unlock growth or a successful sale.

Grow and Exit: Strategic Moves for Business and Real Estate Owners

Format: 60–90 minute keynote or workshop

 

This program is perfect for:

  • Business owners and principals
  • Real estate investors and portfolio managers

 

The audience will leave with:

  • Clear frameworks to grow and scale their business or real estate holdings
  • Actionable strategies to maximize value and prepare for a successful...
Real EstateStrategic PlanningBusiness GrowthGovernmentEducational / InformativeStrategic Planning

Deal Structuring and Capital Strategies for Owners

Format: 60-minute workshop or virtual presentation

 

This program is perfect for:

  • Business owners looking to raise capital
  • Real estate investors scaling their portfolios

 

The audience will leave with:

  • Practical steps to structure deals and attract equity efficiently
  • Insights to optimize transactions while protecting value and preparing for...
BusinessBusiness GrowthFinanceReal EstateEducational / InformativeStrategic Planning

Governance and Strategic Planning for Owners

Format:  60–90 minute keynote, workshop, or virtual presentation

 

This program is perfect for:

  • Business owners and executives preparing for growth or a sale
  • Real estate owners or investors navigating leadership transitions

 

The audience will leave with:

  • Clear frameworks to strengthen governance and board oversight
  • Practical strategies to manage...
BusinessStrategic PlanningBusiness GrowthGovernmentEducational / InformativeStrategic Planning

Capital, Equity, and Deal Structure for Growth and Exit

Format: 60–90 minute keynote, workshop, or virtual presentation

 

This program is perfect for:

  • Real estate investors raising capital
  • Business owners seeking growth funding
  • Entrepreneurs preparing for liquidity

 

The audience will leave with:

  • Clear strategies to structure equity and attract capital
  • Frameworks to reduce tax exposure and increase...
Real EstateBusiness GrowthEducational / InformativeFinancial Management