Diamond Wealth Strategies is a boutique financial services firm that offers a comprehensive suite of advisory services catering to the unique needs of family offices, ultra high net worth individuals, and business owners. Diamond represents 85 family offices ranging in size from $250 million to $15 billion.

We serve as an outsourced private equity division for Family Offices that do not currently have a dedicated private equity team, but still want to make direct investments. In addition, through our partnership with Dresner Partners, we offer the services of a middle market investment bank specializing in merger & acquisition advisory, institutional private placements of debt and equity, financial restructuring and corporate turnaround, valuation and strategic consulting. Our clients are middle market companies operating in both the U.S. and internationally. We are deeply committed to exceeding client expectations and maintaining the highest levels of integrity. Our experienced professionals have the foresight necessary to navigate through highly complicated transactions to maximize value for our clients.

Our third division, Wealth Transfer, works with FAMILY OFFICES, ultra high net worth individuals, and business owners in identifying strategies that may minimize transfer taxes such as gift, estate, and generation skipping taxes while maintaining the family’s planning objectives. We accomplish this by working closely with a client’s existing advisor network to understand the nature of their assets, estate plan and objectives in a comprehensive manner.

Diamond was founded on the principles that each client will receive customized advice and an unmatched level of personal service and confidentiality. With an emphasis on providing creative and results-driven services that go beyond what many have come to expect from traditional financial advisors, the team at Diamond is dedicated to creating holistic financial solutions that integrate every aspect of our client's life. Diamond's national client base is served by a team with offices in Chicago, New York, San Diego, and Naples.

We have assembled a team and surrounded ourselves with some of the top experts in the country.

Members of our team include:

  • FORMER COO OF CITADEL -- A $25 BILLION INTERNATIONAL HEDGE FUND
  • FORMER HEAD OF DELOITTE'S FAMILY WEALTH PLANNING AND FAMILY OFFICES PRACTICES
  • FOUNDER AND PRESIDENT OF A BOUTIQUE INVESTMENT BANKING FIRM WITH OVER 30 YEARS OF EXPERIENCE SPECIALIZING IN MIDDLE MARKET BUSINESSES
  • FOUNDER AND MANAGING PARTNER OF A HIGHLY SUCCESSFUL MIDDLE MARKET PRIVATE EQUITY FIRM
  • PAST PRESIDENT OF THE MILLION DOLLAR ROUND TABLE
  • FORMER PRESIDENT AND COO OF A MULTI $BILLION FAMILY OFFICE
  • FORMER HEAD OF A $1 BILLION FAMILY OFFICE IN CHARGE OF THE ALTERNATIVES INVESTMENT GROUP
  • FORMER PRESIDENT, COO AND A MEMBER OF THE BOARD OF DIRECTORS OF CLARK, INC. -- AN NYSE LISTED COMPANY

DIAMOND WEALTH STRATEGIES ANNOUNCES PARTNERSHIP WITH FORMER PRESIDENT OF CROWN FAMILY PHILANTHROPIES & EXECUTIVE DIRECTOR OF OPRAH WINFREY FOUNDATIONS


Caren started Croland Consulting to help high net worth families, businesses, and agencies develop philanthropic practices in line with their values. She focuses on governance, family engagement across generations, strategic planning and portfolio evaluation. She uses evidence based tools to understand both internal and external philanthropic landscapes, and coaches philanthropic professionals to realize efficiency and potential.


Prior to opening Croland Consulting, Caren served as President of Crown Family Philanthropies for eight years as the first professional, non-family leader. While there, she managed organizational redesign and growth, engaged multiple generations of family members in philanthropic activities, planned and facilitated policy development, and guided strategic initiatives in the U.S., Israel, and the developing world.


Caren built and managed Oprah Winfrey’s philanthropies including Oprah’s Angel Network (a public charity), and the Oprah Winfrey Foundation (a private foundation). She was involved in development of numerous programs both on and off the Oprah Winfrey Show. Projects included building schools, education programs, and economic development initiatives in South Africa, building the Oprah Winfrey Boys and Girls Club in Kosciusko Mississippi, and disaster recovery and rebuilding efforts following Hurricane Katrina and the Indian Ocean Tsunami.


Caren is a board director and finance committee member of The Poetry Foundation and a founding director of Leading Edge, a group formed to build organizational strength in nonprofit agencies. She is a member of the Illinois Attorney General’s Charitable Advisory Council, an Accreditation Advisory Committee member at the Spertus Institute, an advisor to the Lily School of Family Philanthropy, and an advisor to the MacArthur Foundation. Caren speaks about philanthropy and social change to groups of donors and to students across the U.S. and Canada.


Formerly she served as a trustee and finance committee member of the Jewish Funders Network, and a trustee of Forefront, (previously the Chicago Donors Forum), where she chaired the board development and executive search committees and continues as part of the Family Philanthropy Round Table. Caren was founding director of Project&, a creative agency focused on addressing critical social issues through the arts. She chaired the Council on Foundations’ 2013 Annual Conference in Chicago, as well as two Council awards committees for excellence in grant-making. She served on UNICEF’s Orphans and Vulnerable Children Committee in the mid-2000s.


Caren has a degree in Broadcast Journalism from Emerson College and a certificate in strategic leadership from Stanford’s Graduate School of Business.


Caren enjoys coaching, mentoring, and working alongside people who believe they can make the world a better place.