Patrick Ryan, founder and CEO of Ryan Specialty Group, built a global specialty insurance powerhouse by focusing on complex, hard-to-place risks underserved by traditional carriers. A veteran of the industry who previously founded Aon, Ryan launched Ryan Specialty in 2010 to create a wholesale brokerage and underwriting platform centered on expertise, analytics, and specialty distribution. Under his leadership, the firm scaled rapidly through organic growth and acquisitions, went public, and became a key intermediary for insurers and brokers worldwide. Ryan’s career reflects decades of industry shaping, disciplined execution, and category creation in specialty insurance.

P. J. Hyett, cofounder of GitHub, helped create the platform that became the default home for modern software collaboration, reshaping how developers build, review, and ship code at global scale. As GitHub evolved from a developer tool into a foundational layer of the internet’s software stack, Hyett played a key role in its early product DNA and community-first growth, helping turn open-source momentum into a dominant enterprise platform. GitHub’s rise culminated in its landmark acquisition by Microsoft, cementing Hyett’s place among the entrepreneurs who defined the modern developer economy.

Neil Bluhm, real estate developer and casino magnate, built a diversified empire spanning luxury hotels, gaming, and urban real estate through long-term vision and disciplined capital deployment. As cofounder of JMB Realty, he helped shape landmark developments across major U.S. cities before expanding aggressively into gaming as a principal owner of Rush Street Gaming and Rush Street Interactive. Bluhm is also a major civic philanthropist, supporting education, healthcare, and cultural institutions in Chicago and beyond, blending large-scale commercial development with sustained community investment.

Michael Polsky, founder and CEO of Invenergy, is one of the most influential builders of the modern renewable-energy landscape in North America. After immigrating to the United States from Ukraine, he launched multiple successful energy ventures before founding Invenergy in 2001 and growing it into a global leader in wind, solar, and advanced energy-storage development. With billions invested in clean-power infrastructure and a portfolio of projects across more than a dozen countries, Polsky has become a pioneering force behind the energy transition—pairing engineering rigor with long-term capital and policy leadership to accelerate the shift toward sustainable power systems.

Michael Krasny, founder of CDW, built one of America’s largest and most enduring technology solutions providers from a small Chicago basement startup into a multibillion-dollar enterprise. Beginning in 1984 by selling IBM personal computers to local businesses, Krasny expanded CDW into a leading distributor of hardware, software, and integrated IT solutions for corporations, government agencies, and educational institutions nationwide. Under his disciplined leadership and customer-centric philosophy, CDW went public and sustained decades of growth through strategic acquisitions and deep vendor partnerships. Krasny’s journey from entrepreneur to tech industry titan exemplifies long-term execution and operational excellence in enterprise technology services.

Matthew Roszak, cofounder and chairman of Tally Capital, is one of the earliest and most influential institutional investors in blockchain and digital assets. A former private equity executive, Roszak pivoted to crypto in the early 2010s, backing foundational projects such as Ethereum, Blockstack, and numerous Web3 infrastructure companies before the sector entered the mainstream. Beyond investing, he has played a key policy and advocacy role as chairman of the Chamber of Digital Commerce, helping shape regulatory dialogue around blockchain adoption in the United States. Known for his long-term conviction, ecosystem-level thinking, and bridge-building between technology and policy, Roszak remains a central figure in the maturation of the crypto economy.

Mark Walter, cofounder and CEO of Guggenheim Partners, built one of the world’s largest and most diversified global investment firms, overseeing hundreds of billions in assets across insurance, asset management, and advisory services. A former attorney, Walter helped architect Guggenheim’s distinctive structure, combining long-duration insurance capital with alternative and fixed-income strategies. Beyond finance, he is widely known as the controlling owner of the Los Angeles Dodgers, where he led a dramatic turnaround of the franchise, delivering multiple championships and setting new standards for investment in professional sports. Walter’s influence spans global finance, infrastructure, and elite sports ownership.

Kenny Troutt, billionaire entrepreneur and founder of Excel Communications, built his fortune by pioneering long-distance telecommunications sales through network marketing, later selling the company to Teleglobe for billions. After exiting telecom, he turned his focus to thoroughbred horse breeding and racing, creating WinStar Farm in Kentucky, which has produced multiple classic winners, including Kentucky Derby and Belmont Stakes champions. Known for his competitive spirit, strategic investment style, and passion for racing, Troutt has become a major figure in American equestrian sports while maintaining a diverse personal investment portfolio.

Justin Ishbia, founder and managing partner of Shore Capital Partners, has built one of the fastest-growing private equity firms in the lower middle market, backing healthcare, business services, and food companies through a disciplined strategy of operational improvement and platform roll-ups. Under his leadership, Shore has completed hundreds of acquisitions and created scaled national platforms across dental, veterinary, behavioral health, and specialty manufacturing, while consistently generating strong returns. A former practicing attorney with a sharp eye for founder-led businesses, Ishbia is also a major investor in sports as co-owner of the Phoenix Suns and Phoenix Mercury alongside his brother, Mat Ishbia. His combination of analytical rigor, deal intensity, and strategic focus has made him a rising force in private equity.

Joe Mansueto, founder and executive chairman of Morningstar, transformed a one-man startup launched in his Chicago apartment into one of the world’s most trusted providers of investment research, ratings, and financial data. Since founding the company in 1984, he has championed transparency, independent analysis, and investor empowerment, expanding Morningstar into a global platform serving millions of investors and thousands of institutions across more than 25 countries. After taking the company public and stepping back from day-to-day operations, Mansueto has become an influential civic leader, philanthropist, and sports owner—acquiring Major League Soccer’s Chicago Fire and supporting major cultural and educational initiatives. His legacy combines entrepreneurship, integrity, and a long-term commitment to investor advocacy.

Joseph Grendys, owner, chairman, and CEO of Koch Foods, built one of America’s largest vertically integrated poultry producers from a small Chicago-based chicken distributor into a multibillion-dollar industry giant. Joining the company in the 1980s, he expanded Koch Foods through strategic acquisitions, processing plant development, and an aggressive focus on efficiency across farming, processing, and distribution. Today, the company supplies major retailers and food-service chains nationwide, ranking among the top poultry producers in the United States. Known for his low profile and disciplined operations, Grendys has become one of the most successful self-made figures in American agribusiness.

John Calamos, founder and global CIO of Calamos Investments, is a pioneering figure in convertible securities and risk-managed equity investing. After serving as a U.S. Air Force fighter pilot, he launched his investment firm in 1977 with a strategy centered on convertibles—an overlooked asset class he helped bring into mainstream institutional portfolios. Under his leadership, Calamos Investments grew into a multibillion-dollar asset manager serving global institutions, public funds, and private wealth clients, while Calamos became known as a leading author and educator on volatility, capital structure, and portfolio construction. His disciplined, analytical approach has earned him a reputation as both an innovator and one of the most respected long-term investors in modern finance.

Jerry Reinsdorf, longtime owner of the Chicago Bulls and Chicago White Sox, is one of the most influential figures in American professional sports. After building his wealth in real estate and tax-shelter investments, he purchased the White Sox in 1981 and the Bulls in 1985—guiding the teams through eras that cemented their place in sports history. Under his stewardship, the Bulls won six NBA championships in the Michael Jordan era, while the White Sox captured a World Series title in 2005, ending an 88-year drought. Known for his sharp business acumen, loyalty to his organizations, and major impact on league governance, Reinsdorf remains a defining and sometimes controversial presence in modern sports ownership.

J.B. Pritzker, billionaire businessman, philanthropist, and the 43rd governor of Illinois, is a prominent member of the Pritzker family whose fortune stems from the creation of the Hyatt hotel empire and a vast portfolio of industrial holdings. Before entering politics, he founded and led private investment firm Pritzker Group, backing technology, manufacturing, and venture capital ventures and helping shape Chicago’s modern startup ecosystem. As governor since 2019, Pritzker has focused on economic development, infrastructure, education, and social policy, leveraging both his business background and philanthropic commitments to influence public life on a statewide and national scale.

Jack Schuler, veteran healthcare executive and investor, is best known for his leadership at Abbott Laboratories and Stericycle, where he helped build two of America’s most successful healthcare companies. After serving as president and COO of Abbott, he became CEO of Stericycle, transforming it into a multibillion-dollar medical waste management leader. Later, through his investment firm, he backed numerous biotech and medical device startups, shaping the future of healthcare innovation. A noted philanthropist, Schuler has also supported education and healthcare initiatives through the Schuler Education Foundation.

Eric Lefkofsky is a tech entrepreneur, investor, and philanthropist. He co‑founded Groupon, InnerWorkings, Echo Global Logistics, and Mediaocean, and now serves as CEO of Tempus AI, advancing precision medicine using AI. He also co-leads Lightbank, a venture fund backing disruptive startups, and chairs the Lefkofsky Family Foundation.

David Steward is an American billionaire tech entrepreneur who founded World Wide Technology (WWT) in 1990 with minimal capital. A Central Missouri alumnus, he transformed WWT into one of the largest African-American–owned companies in the U.S., generating over $11 billion in annual revenues. Known for his faith-driven leadership and civic engagement, Steward also founded Telcobuy and chairs major nonprofit boards.

David Kabiller is the co‑founding principal and Head of Business Development at AQR Capital Management, the global quantitative investment firm he launched in 1998 alongside Cliff Asness and others. He spearheaded AQR’s international expansion, retail mutual fund offerings, and educational initiatives such as AQR University and the AQR Insight Award. A former athlete, he holds degrees in economics and finance from Northwestern and continues to support research via prizes at Northwestern and London Business School. 

Craig Duchossois is an American billionaire investment executive and lifelong leader of the Duchossois Group, the diversified family firm originally built by his father, Richard L. Duchossois. Under his tenure, the firm became the largest individual shareholder of Churchill Downs, with over $700 million in equity. He has served in the U.S. Marine Corps, earned an MBA from SMU, and led the evolution of Duchossois Capital Management into a family office powerhouse.

Carl Thoma is a veteran private-equity pioneer and co-founder/managing partner of Thoma Bravo, one of the world’s largest software-focused buyout firms managing more than $130 billion in assets. A Stanford MBA and Oklahoma State alumnus, he began his career in 1980 with the predecessor firm GTCR and helped invent the “buy and build” consolidation strategy that underpins his longtime success in PE.