Beyond Billions: What Drives the World’s Most Successful Entrepreneurs After the Big Win?

NEW YORK, NY – January 12, 2026 – For most entrepreneurs, a multi-million or billion-dollar exit is the end of the game. But for a select few, it’s the beginning of a new, far more complex one. This is the uncharted territory explored in Season 2 of NEXT with Michael Sonnenfeldt, a podcast that pulls back the curtain on the private conversations of the world's most accomplished wealth creators.

Hosted by Michael Sonnenfeldt, the founder and chairman of the elite peer network TIGER 21, the biweekly podcast returns today, delving into the profound question he has helped entrepreneurs navigate for over 25 years: What’s next? The series offers a rare public window into the challenges and opportunities that arise after extraordinary financial success, moving beyond balance sheets to explore purpose, legacy, and personal reinvention.

The 'Prism Moment': Navigating Life After the Big Exit

Sonnenfeldt frames this pivotal transition as the “prism moment.” It’s the point at which an entrepreneur’s life, once a laser-focused beam aimed at building a single business, refracts into a wide spectrum of new opportunities, responsibilities, and existential questions. After the relentless grind of wealth creation, the sudden arrival of immense liquidity and unstructured time can trigger an identity crisis.

"What has always fascinated me most is not just how people succeed, but how they think, how they make decisions, and how success ultimately changes the way they see the world," Sonnenfeldt stated in the season announcement. "On NEXT, we slow those moments down. We talk honestly about risk, judgment, resilience, and timing—and about the emotional and psychological shifts that come with building something meaningful."

This “prism moment” involves a profound psychological shift. For many founders, their identity is inextricably linked to their company. The sale of that company can leave them feeling rudderless, despite their financial security. The challenge becomes reconstructing a sense of purpose when the primary driver of their life is gone. The podcast aims to dissect these moments, providing a roadmap for others by examining how today's top leaders navigate this phase, shifting from pure wealth creation to wealth preservation, strategic investment, and long-term legacy planning.

Inside TIGER 21: The Elite Network Opening Its Playbook

The podcast is an extension of the work Sonnenfeldt has done for decades with TIGER 21. Founded over 25 years ago, TIGER 21 (The Investment Group for Enhanced Results in the 21st Century) is arguably the world’s most exclusive peer-to-peer learning network for ultra-high-net-worth individuals. Its membership, which requires a minimum of $20 million in liquid, investable assets, collectively manages over $200 billion.

Unlike networks such as the Entrepreneurs' Organization (EO) or Young Presidents' Organization (YPO), which often cater to leaders actively scaling their businesses, TIGER 21 is designed for those who have already reached the summit and are figuring out what to do with the view. Members meet in confidential, high-trust groups that function as a personal board of directors, sharing brutally honest feedback on everything from asset allocation to family governance.

A core element of the TIGER 21 experience is the “Portfolio Defense,” where members present their entire investment portfolio for critique by their peers. This intense process is designed to challenge assumptions, identify blind spots, and improve decision-making. By launching the NEXT podcast, Sonnenfeldt is effectively democratizing the ethos of these closed-door sessions, bringing the key insights and frameworks to a much broader audience.

A New Breed of Leaders: From Profit to Purpose

Season 2 underscores the diversity of paths taken after the “prism moment” with a lineup of six leaders from varied and demanding industries. The guests are not just retired executives but active investors, builders, and strategists shaping what comes next in their respective fields.

Featured guests include Omar Simmons, founder of Exaltare Capital Management and the former CEO and Executive Chairman of a Planet Fitness franchisee group he grew from 15 to over 100 locations before its sale. With over two decades in private equity, Simmons represents the sophisticated investor who continues to build and scale new ventures after a major exit. Another guest, Peggy Styer, co-founder and Managing Partner at Razor's Edge Ventures, operates at the critical intersection of technology and national security. A serial entrepreneur who has built and sold multiple companies to giants like Raytheon and Boeing, Styer exemplifies the move from operator to strategic investor, funding the next generation of mission-critical technologies. The season kicks off with marketing entrepreneur Mae Karwowski, a leader in the dynamic creator economy, showcasing how the principles of post-success navigation apply even in the most modern industries.

These conversations promise to go beyond typical business success stories, focusing instead on the strategic thinking, risk assessment, and value systems that guide these leaders' decisions in their second and third acts.

Redefining Legacy: Wealth with a Conscience

Reflecting a growing trend among the ultra-wealthy, the podcast also emphasizes the increasing importance of philanthropy and social impact. The concept of legacy is evolving from simply passing down assets to instilling values and making a tangible difference in the world. Season 2 formalizes this theme with a dedicated philanthropic giving moment.

Throughout the first quarter of 2026, the show will match listener donations dollar-for-dollar up to $100 per gift, with a cap of $10,000 per organization. This initiative is more than a marketing tool; it’s a practical application of the show's core message. It aligns the podcast's mission with the actions of its subjects, who are increasingly integrating strategic giving and impact investing into their wealth management strategies.

For many of the world's most successful people, philanthropy is the new frontier of entrepreneurship—a way to apply their skills in problem-solving, scaling, and innovation to address complex global challenges. The podcast provides a platform to explore this shift, examining how leaders are building legacies that are measured not just in dollars, but in impact. As the definition of success continues to evolve, NEXT with Michael Sonnenfeldt provides an essential guide to the questions that matter most after the money has been made, with new episodes available on Apple, Spotify, YouTube, and the MUUS website.