TIGER 21 Chicago

TIGER 21 Chicago is part of the premier global peer membership organization for ultra-high-net-worth entrepreneurs, investors and executives. With success comes challenges and opportunities, and TIGER 21 Members, through deep, trusted relationships, rely on each other to take their lives to the next level.

Chairs

  • Ron Diamond - TIGER 21 Chair, Chicago

    Ron Diamond

    Ron Diamond

    TIGER 21 Chair, Chicago & Family Office

    Ron Diamond is the Chair of Chicago 02, 03 and Family Office 02. Diamond is a longtime investor and entrepreneur and the Founder and Chairman of Diamond Wealth with divisions focusing on philanthropy, wealth transfer, investment banking, social impact, and governance. Ron serves on the Advisory Board of 10 privately held companies and acts as Chairman for 4 of them. He is the Founder of Family Office World, a podcast whose mission is to educate the market about Family Offices. Diamond is deeply committed to giving back and is an active philanthropist and civic leader. He is serves on the Leadership Circle of the Aspen Institute, a global nonprofit organization committed to realizing a free, just, and equitable society. He also sits on the Board of several other charities and non-profit organizations in his community. Diamond studied at Northwestern University, graduating Magna Cum Laude and earning his degree in Economics.
  • David Kirshenbaum

    David Kirshenbaum

    TIGER 21 Chair, Chicago

    David Kirshenbaum is Chair of Chicago 04 and 05. Kirshenbaum has had a varied and diverse career in real estate development, business development and transaction management. As a late-in-life entrepreneur, Kirshenbaum launched MeadeCo LLC–a virtual merchant bank in 2021. At MeadeCo, Kirshenbaum connects clients in CBD, cannabis, healthy food+bev, tech and real estate with capital and opportunity. Kirshenbaum has a large and diverse network and has created a good deal of value “connecting the dots” as a function of his “Slumdog Millionaire lifestyle.” He has been an active investor in a range of early-stage, seed, and start-up companies along with real estate, credit, and other investment vehicles. He graduated from Emory, Northwestern Law School, and the Kellogg Graduate School of Management and has taught as an adjunct professor at the UN schools from which he graduated. Kirshenbaum is married with three adult children.
  • Mason Phelps

    Mason Phelps

    TIGER 21 Chair

    Mason Phelps is Chair of Chicago 06. He started his career as a trader at the Chicago Board Options Exchange and eventually became one of the largest independent equity options traders in the country. Phelps stepped away from trading in 2013 to focus on investing in real estate, private lending, venture capital, and proprietary trading. The events of 2020 created new market opportunities and he has now returned to trading his own capital full-time. He is a board member at Beat The Streets Chicago Wrestling and Daniel Murphy Scholarship Fund. He teaches financial literacy classes at high schools around the city; coaches volleyball at the Latin School of Chicago; and is the community advisor to the school’s investment club. He holds a Bachelor's Degree in Economics and Psychology from Northwestern University. He currently resides in the Old Town neighborhood of Chicago with his wife Abby and their three young children. He and Abby spent 18 months traveling the world and have been to over 70 countries and all seven continents.
  • Ron Diamond - TIGER 21 Chair, Chicago

    Ron Diamond

    TIGER 21 Chair, Chicago & Family Office

    Ron Diamond

    TIGER 21 Chair, Chicago & Family Office

    Ron Diamond is the Chair of Chicago 02, 03 and Family Office 02. Diamond is a longtime investor and entrepreneur and the Founder and Chairman of Diamond Wealth with divisions focusing on philanthropy, wealth transfer, investment banking, social impact, and governance. Ron serves on the Advisory Board of 10 privately held companies and acts as Chairman for 4 of them. He is the Founder of Family Office World, a podcast whose mission is to educate the market about Family Offices. Diamond is deeply committed to giving back and is an active philanthropist and civic leader. He is serves on the Leadership Circle of the Aspen Institute, a global nonprofit organization committed to realizing a free, just, and equitable society. He also sits on the Board of several other charities and non-profit organizations in his community. Diamond studied at Northwestern University, graduating Magna Cum Laude and earning his degree in Economics.

    David Kirshenbaum

    TIGER 21 Chair, Chicago

    David Kirshenbaum

    TIGER 21 Chair, Chicago

    David Kirshenbaum is Chair of Chicago 04 and 05. Kirshenbaum has had a varied and diverse career in real estate development, business development and transaction management. As a late-in-life entrepreneur, Kirshenbaum launched MeadeCo LLC–a virtual merchant bank in 2021. At MeadeCo, Kirshenbaum connects clients in CBD, cannabis, healthy food+bev, tech and real estate with capital and opportunity. Kirshenbaum has a large and diverse network and has created a good deal of value “connecting the dots” as a function of his “Slumdog Millionaire lifestyle.” He has been an active investor in a range of early-stage, seed, and start-up companies along with real estate, credit, and other investment vehicles. He graduated from Emory, Northwestern Law School, and the Kellogg Graduate School of Management and has taught as an adjunct professor at the UN schools from which he graduated. Kirshenbaum is married with three adult children.

    Mason Phelps

    TIGER 21 Chair

    Mason Phelps

    TIGER 21 Chair

    Mason Phelps is Chair of Chicago 06. He started his career as a trader at the Chicago Board Options Exchange and eventually became one of the largest independent equity options traders in the country. Phelps stepped away from trading in 2013 to focus on investing in real estate, private lending, venture capital, and proprietary trading. The events of 2020 created new market opportunities and he has now returned to trading his own capital full-time. He is a board member at Beat The Streets Chicago Wrestling and Daniel Murphy Scholarship Fund. He teaches financial literacy classes at high schools around the city; coaches volleyball at the Latin School of Chicago; and is the community advisor to the school’s investment club. He holds a Bachelor's Degree in Economics and Psychology from Northwestern University. He currently resides in the Old Town neighborhood of Chicago with his wife Abby and their three young children. He and Abby spent 18 months traveling the world and have been to over 70 countries and all seven continents.

TIGER 21 offers Members a confidential place to discuss, learn, and network as you navigate these issues of wealth and success through:

Candid Monthly Group Meetings

with up to 15 peers who become your trusted confidantes

Cutting-Edge Thought Leadership

through virtual and in-person conferences and events

Access to an Unparalleled Network

of wealth creators worldwide with deep collective intelligence

I never thought I’d find a group aligned with my core vision of trying to evolve, grow, preserve wealth, be a great human being, and raise great kids. TIGER 21 changed my life. It changed me as a person, and it changed the future of what it means to be a Dyrdek.

Rob Dyrdek

When you’re blessed and you’re growing your world, it’s very difficult to talk to people about how much you have and what plans you have. But TIGER 21 offers a platform where you can openly share with people who are in the same position.

Sanjay Singhania

When you have a lot of success, it’s a great thing, but it’s also a little isolating. Now I’m in a community of people that are faced with the same things I’m faced with.

Doug McKeige

Explore the Issues
That Keep Wealth
Creators Up At Night

TIGER 21 is an exclusive global community of ultra-high- net-worth entrepreneurs, investors, and executives. Fill out an inquiry form, and a member of our team will be in touch.