Scale and Exit

Who We Are

Alexander Enterprise is the family office of entrepreneur Greg Alexander. The family members, and their advisors, invest their time, talent, and treasure in one thing- boutique professional services firms. The combination of growth capital with years of accumulated expertise in this segment results in exceptional returns for the family, and its partners.

“90% of firms fail to scale and exit because they lack capital and knowhow. We can solve that problem.”

What We Do

Alexander Enterprise is hyper specialized in its approach. The organization is focused on solving one problem and it believes if this problem is resolved, extraordinary returns are available.

The problem of focus is there are approximately 2 million professional services firms in the US, but 90% of them never reach scale. Because of this, the owners of these firms rarely create wealth with a successful exit. Yet, they should because companies spend $560 billion annually on professional services.

There is a solution to this problem which results in significant wealth creation. The solution is specialized management know how and plenty of available growth capital. Alexander Enterprise has developed these two missing ingredients by specializing in six ways.

  • 1-The industry: We only work with professional service firms
  • 2-The segment: Pre-scale boutiques are our focus
  • 3-The individual: We work with ownership
  • 4-The funds: We invest our own personal capital
  • 5-The know how: Relentless accumulation of specific management knowledge
  • 6-The team: A family office staff with proven experience handling boutique professional firms
Alexander Enterprise Team

How We Do It

We provide you with growth capital and management knowhow. The lack of these two resources is why 90% of firms fail to scale and exit. We partner with firms who have what it takes to reach the pinnacle of their success but may be lacking the resources to capitalize on the opportunity.

Like steel sharpens steel, we take the proven strengths of your business, add our personal growth capital and specialized business knowhow in boutique professional service firms and together we successfully scale your firm and ignite your exit.

Alexander Enterprise What We Do
Alexander Enterprise Who We Are

Why We Do It

The mission of this family office is to create opportunity for the family members, and the owners we invest in. The family’s original wealth creator, Greg Alexander, is driven by the idea of leaving a legacy by taking risks and pursuing extraordinary accomplishments.

The purpose of the organization is to serve the next generation by preserving, and evolving, the body of work of Greg Alexander who laid the foundational building blocks of success. The ongoing accumulation of wisdom from each investment contributes to growth and opportunity for all involved.

Alexander Enterprise Greg Alexander

The Team


Greg Alexander is the Chief Investment Officer for Alexander Enterprise. Greg contributes to the family by deciding which entrepreneurs to bet on, and which firms to invest in. He contributes to entrepreneurs by helping them scale and exit their firms by sharing how he scaled and exited his.

Prior to partnering with his family, and opening the family office, Greg had two careers spanning 25 years. He co-founded SBI, a professional service firm, and served as CEO for 11 years. After scaling the firm he successfully exited in 2017 by selling his interest in the firm. Prior to SBI, Greg was an executive at EMC Corporation, a leader in the data storage industry.


Doug Alexander, the older brother of Greg, is a Partner at Alexander Enterprise. Doug contributes to the family by sourcing investment opportunities, and deploying the family's capital.  Doug contributes to entrepreneurs by helping them develop a strategy which allows them to scale faster and exit for larger sums and on better terms.


Doug has 25 years of experience in growing pre-scale firms. He is an expert in culture development, sales, marketing, operations, finance, service offering development, and recruiting top industry talent to fill strategic positions designed to drive growth for companies.  Under Doug’s leadership, his companies have won numerous industry awards and have been recognized as best places to work.


Matt Alexander, the son of Doug, and the nephew of Greg, is an Associate at Alexander Enterprise.  Matt contributes to the family by assisting in opportunity screening, and due diligence.  In addition, Matt contributes to entrepreneurs by helping them overcome the obstacles of scaling and exiting their professional services firms. He is a graduate of the University of Massachusetts-Amherst.