| 2001 | MEMatan EvenEntrepreneur, Investor | Investors | $50M |
| 2002 | MHMellody HobsonBusinesswoman, Investor | Entrepreneurs | $50M |
| 2003 | MCMike CessarioEntrepreneur, CEO | Executives | $50M |
| 2004 | MHMiriam HaartCEO, Entrepreneur | Executives | $50M |
| 2005 | MTMonika TuReal Estate Entrepreneur | Real Estate | $50M |
| 2006 | PCPaul CastellanoCrime Boss, Businessman | Entrepreneurs | $50M |
| 2007 | RHRyan HalsaEntrepreneur, Investor | Investors | $50M |
| 2008 | VSVick StrizheusInternet Entrepreneur, Digital Marketer | Entrepreneurs | $50M |
| 2009 | ABAl BoscovBusinessman, Philanthropist | Entrepreneurs | $50M |
| 2010 | BSBalaji SrinivasanEntrepreneur, Angel Investor, Former CTO of Coinbase | Investors | $50M |
| 2011 | CMClara Chia MartiEntrepreneur, Investor, Philanthropist | Investors | $50M |
| 2012 | ESEli StefanskyInvestor, Entrepreneur | Investors | $50M |
| 2013 | FMFrank MecumBusinessman, Car Auctioneer | Entrepreneurs | $50M |
| 2014 | HMHeather MillsEntrepreneur, Businesswoman, Activist, Former Model | Entrepreneurs | $50M |
| 2015 | ITIlan TobianahEntrepreneur, Investor | Investors | $50M |
| 2016 | ISIman ShokuohizadehBusinessman, Investor | Entrepreneurs | $50M |
| 2017 | JMJose R MasCEO of MasTec | Executives | $50M |
| 2018 | KLKenny LloydEntrepreneur, Network Marketer, Author, Public Speak | Entrepreneurs | $50M |
| 2019 | LHLesley HoEntrepreneur, Investor | Investors | $50M |
| 2020 | MBMark BaumCEO of Spruce Capital, Investor | Executives | $50M |
| 2021 | RKRich KleimanSports Manager, Entrepreneur, Producer | Entrepreneurs | $50M |
| 2022 | RSRoman SharfEntrepreneur, CEO of Luxury Bazaar, YouTuber | Executives | $50M |
| 2023 | SFSalt Life FounderEntrepreneur, Businessman | Entrepreneurs | $50M |
| 2024 | SBStephen BarclayEntrepreneur, Investor, Television Personality | Investors | $50M |
| 2025 | SHSteve HuffmanCo-founder, CEO of Reddit; Entrepreneur | Founders | $50M |
| 2026 | TCTodd ChrisleyTelevision Personality, Real Estate Mogul | Real Estate | $50M |
| 2027 | TMTopper MortimerBusinessman, Socialite | Entrepreneurs | $50M |
| 2028 | VMVeggie MamaEntrepreneur, CEO | Executives | $50M |
| 2029 | YCYasin CengizEntrepreneur, Investor | Investors | $50M |
| 2030 | BKBrianne KimmelInvestor, Entrepreneur | Investors | $50M |
| 2031 | CYCharles Michael YimEntrepreneur, Investor, Television Personality | Investors | $50M |
| 2032 | CCChase CominskyEntrepreneur, Investor | Investors | $50M |
| 2033 | CMCheryl McKissackPresident and CEO of McKissack & McKissack | Executives | $50M |
| 2034 | CCClara ChiaEntrepreneur, Investor | Investors | $50M |
| 2035 | DMDavid MicheryCEO of Mullen Technologies, Entrepreneur | Executives | $50M |
| 2036 | DPDavid PridhamCEO of Dominion Harbor Group | Executives | $50M |
| 2037 | DWDel WalmsleyEntrepreneur, Real Estate Investor, Radio Host | Real Estate | $50M |
| 2038 | DDDennis DeGoriEntrepreneur, Nightclub Owner | Entrepreneurs | $50M |
| 2039 | DJDuke The JewelerJeweler, Entrepreneur | Entrepreneurs | $50M |
| 2040 | EGElliot GraingeFounder and CEO of 10K Projects | Founders | $50M |
| 2041 | FBFootball BillionaireEntrepreneur, Board Game Developer | Entrepreneurs | $50M |
| 2042 | FLFrank LucasDrug Trafficker, Businessman | Entrepreneurs | $50M |
| 2043 | FRFrank RoesslerReal Estate Investor, CEO of Ashcroft Capital | Real Estate | $50M |
| 2044 | GBGreg BeckerCEO of Silicon Valley Bank | Executives | $50M |
| 2045 | HHHugh HefnerPublisher, Businessman | Entrepreneurs | $50M |
| 2046 | IAIssa AsadEntrepreneur, Businessman | Entrepreneurs | $50M |
| 2047 | JGJason GuttermanEntrepreneur, Investor | Investors | $50M |
| 2048 | JLJeff LazkaniCEO of Icon Media Direct, Entrepreneur | Executives | $50M |
| 2049 | JSJeff ShellCEO of NBCUniversal | Executives | $50M |
| 2050 | JHJelani HarrisonEntrepreneur, Investor | Investors | $50M |
| 2051 | JWJonathan WeinbergerEntrepreneur, Investor | Investors | $50M |
| 2052 | JKJosh KesselmanEntrepreneur, CEO of RAW Rolling Papers | Executives | $50M |
| 2053 | KTKent ThiryHealthcare Executive, Entrepreneur, Philanthropist | Entrepreneurs | $50M |
| 2054 | KBKevin BrittinghamEntrepreneur, Firearms Designer | Entrepreneurs | $50M |
| 2055 | KSKlaus SchwabFounder and Executive Chairman of the World Economic | Founders | $50M |
| 2056 | LMLalit ModiBusinessman, Cricket Administrator | Entrepreneurs | $50M |
| 2057 | LBLavar BallEntrepreneur, Media Personality, CEO of Big Baller B | Executives | $50M |
| 2058 | MFMark FluentReal Estate Investor, Entrepreneur | Real Estate | $50M |
| 2059 | PLPamela LiebmanReal Estate Executive, CEO | Real Estate | $50M |
| 2060 | PRPasquale RotellaMusic Promoter, Entrepreneur | Entrepreneurs | $50M |
| 2061 | RHRaymond HugerBusiness Executive, Entrepreneur, TV Personality | Executives | $50M |
| 2062 | RTRose TotinoEntrepreneur | Entrepreneurs | $50M |
| 2063 | SSSaubhagyaa R SwainEntrepreneur, Investor | Investors | $50M |
| 2064 | SCStephen Weiss CNBCInvestor, Financial Expert, Author, TV Personality | Investors | $50M |
| 2065 | TWThomas WintertonEntrepreneur, Investor | Investors | $50M |
| 2066 | TSTim SeymourInvestor, Financial Analyst, Media Personality | Investors | $50M |
| 2067 | SSSimon SquibbEntrepreneur, Investor, Mentor | Investors | $48M |
| 2068 | RPRaoul PalInvestor, Financial Analyst, Businessman | Investors | $47.5M |
| 2069 | AWAndrew WittyBusiness Executive, Pharmacist | Executives | $47M |
| 2070 | JHJodie HaydonBusinesswoman, Philanthropist | Entrepreneurs | $47M |
| 2071 | JDJudy DupartEntrepreneur, Investor | Investors | $47M |
| 2072 | CBCorie BarryBusiness Executive, CEO of Best Buy | Executives | $46.5M |
| 2073 | BBBarrie Drewitt-BarlowEntrepreneur, Philanthropist, Author | Entrepreneurs | $46M |
| 2074 | OGOlof K GustafssonEntrepreneur, Business Executive | Executives | $45M |
| 2075 | PMPeter MooreBusiness Executive, Advisor | Executives | $45M |
| 2076 | AOAlfie OakesEntrepreneur, Agricultural Business Owner | Entrepreneurs | $45M |
| 2077 | DBDon BlankenshipBusinessman, Former CEO, Political Candidate | Executives | $45M |
| 2078 | JCJohn CasablancasModeling Agent, Entrepreneur | Entrepreneurs | $45M |
| 2079 | JFJohn FurnerPresident and CEO of Walmart U.S. | Executives | $45M |
| 2080 | NBNarvel BlackstockMusic Manager, TV Producer, Former Steel Guitar Play | Real Estate | $45M |
| 2081 | SESteve EasterbrookBusiness Executive, Former CEO of McDonald's | Executives | $45M |
| 2082 | IJImpractical JokersComedians, TV Personalities, Writers, Producers | Real Estate | $44M |
| 2083 | RHRaymond A. HugerEntrepreneur, Businessman | Entrepreneurs | $43.5M |
| 2084 | MSMarge SchottBusinesswoman, Sports Executive | Entrepreneurs | $43M |
| 2085 | GWGai WaterhouseHorse Trainer, Businesswoman | Entrepreneurs | $42.9M |
| 2086 | SWShemara WikramanayakeCEO of Macquarie Group, Financial Executive | Executives | $42.9M |
| 2087 | CHChris HyamsCEO of Indeed | Executives | $42.5M |
| 2088 | JSJay SnowdenCEO and President of Penn National Gaming | Executives | $42M |
| 2089 | RHRay HugerEntrepreneur, Business Executive | Executives | $42M |
| 2090 | BDBill DemchakChairman, President, CEO of PNC Financial Services G | Executives | $42M |
| 2091 | CRCarter ReumEntrepreneur, Author, Venture Capitalist | Investors | $42M |
| 2092 | NJNate and JeremiahInterior Designers, Television Personalities, Author | Real Estate | $42M |
| 2093 | KWKarl WellnerBusiness Executive, Investor | Executives | $41.2M |
| 2094 | RWRd WhittingtonLuxury Car Dealer, Entrepreneur | Entrepreneurs | $41.2M |
| 2095 | VWVoletta WallaceBusinesswoman, Author, Educator | Entrepreneurs | $41M |
| 2096 | CBCharlie BighamEntrepreneur, Founder of Bigham’s Ltd | Founders | $40.6M |
| 2097 | SKScott KirbyCEO of United Airlines | Executives | $40M |
| 2098 | ENErika NardiniCEO of Barstool Sports, Digital Media Executive | Executives | $40M |
| 2099 | RAReggie Fils-AiméBusiness Executive, Public Speaker | Executives | $40M |
| 2100 | SDSara DaviesEntrepreneur, Investor, Television Personality | Investors | $40M |