Michael Sonnenfeldt. Post-Liquidity Ultimate Wisdom

My guest today - Michael Sonnenfeldt - is the source of ultimate wisdom on the life after a liquidity event. He has built and sold multiple companies and is the celebrity founder of TIGER 21, an exclusive global community of ultra-high-net-worth investors. Michael creates exquisite art, collects photography and runs a venture philanthropy firm focusing on climate change. We discuss the importance of post-exit introspection, how a liquidity event teaches us humility, rules of prudent spending, capital preservation vs angel investing, and how to decide whether to start a new business or focus on passive investing.

What We Discussed:

00:00:37: Introduction of Michael, Founder of Tiger21

00:01:53: Discussion on investors

00:02:05: Challenges of investing

00:02:39: Handling Success and Entrepreneurship

00:04:17: Discussion on Turning into an Investor after Being an Entrepreneur

00:06:44: Setting realistic passive returns

00:18:49: Discussion on Family Offices

00:23:49: Michael's personal motivations and the foundations of his success

00:24:55: Michael's ambition and challenges in the early years

00:27:37: Michael's personal experience of hearing loss and its impact on his life

00:28:53: Reflection on the role of luck in building businesses

00:29:04: Discussing the Role of Luck in Success

00:32:46: Overcoming Responsibility and Trauma After Business Success

00:34:46: Navigating Early Success and Future Ventures

00:39:46: Balancing Entrepreneurship and Introspection

00:43:59: The Intersection of Politics, Philanthropy, and Investment

00:49:02: Discovering Philanthropy

00:55:14: Importance of Travel and Cultural Awareness Post-Exit

00:56:22: Passion for Art, Photography and Fashion

00:58:00: Building a Large Photographic Archive

00:58:44: Handling Estates of Important Photographers after they Pass On

00:59:40: Estate Management of Deceased Photographers

01:00:20: Fulfillment in Life

01:01:41: Artwork and Business

01:02:37: Loneliness After Founders Exit

01:03:10: Isolation After Wealth Creation

01:05:10: Inherited Wealth Management

01:06:02: Shift in Wants After Selling Business

01:09:36: Turning Down Family Members' Investment Requests

01:12:07: Generosity Vs Enabling Bad Behavior

01:12:47: Parenting with Wealth

01:14:50: Responsibility Coupled with Inherited Wealth

01:15:14: Preparing Children for Inheritance

01:16:30: Selecting People to Surround Yourself With

01:20:15: Striving for a Life of Meaning and Purpose

01:24:50: Evolution of Tiger Organization and its impact

01:26:54: The Experiences and Learnings from a Long Term Marriage

Michael Sonnenfeldt - Post-Liquidity Ultimate Wisdom

Anastasia Koroleva: [00:00:37 - 00:01:00] Welcome to the Exit Paradox podcast. Here we meet remarkable exited founders to uncover what comes next after selling a business. Did they sustain success and find fulfillment? Let's learn together. Please subscribe to join our community.  Michael, thank you so much for being here with me today. 

Michael Sonnenfeldt: [00:01:01 - 00:01:02] My pleasure. 

Anastasia Koroleva: [00:01:04 - 00:01:34] There is no one on the whole planet who knows more about post exit founder journeys than you. For the past 25 years at least, you've been mentoring and guiding and supporting exited founders with amazing generosity and kindness and grace. For me, as a member and the beneficiary of you creating Tiger 21 in the first place. Given that the name is an abbreviation which includes an investment group, it's the Investment group for enhanced results. 

Michael Sonnenfeldt: [00:01:34 - 00:01:45] Investment group for enhanced results. Not returns. Results. Very important. We don't promise returns, but we do hope for better results. 

Anastasia Koroleva: [00:01:45 - 00:01:53] But I also personally don't necessarily see it as an investment group as much as a community of people who understand each other. 

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