Keith Rabois: A Tech Titan's Journey through Investments, Ventures, and Political Engagements
Biography of Keith Rabois:
Keith Rabois, an American technology executive and investor,
plays a significant role in the tech world. Currently serving as a managing
director at Khosla Ventures, Rabois has a notable history in backing successful
startups at their early stages. Some of his notable investments include PayPal,
LinkedIn, Slide, and Square. Rabois also played a crucial role in the success
of Yelp and the Xoom Corporation by investing in them before their initial
public offerings (IPOs) and securing a position on their boards of directors.
Keith Rabois's most notable investment in recent times is in
the fintech startup Ramp. This startup experienced a remarkable surge in its
valuation, jumping from $3.9 billion to $8.1 billion following a highly
successful Series D funding round in March 2022. This significant increase in
valuation underscores Rabois's astute investment decisions and his ability to
identify promising opportunities in the rapidly evolving fintech landscape.
Rabois is recognized as a key figure within the renowned
"PayPal Mafia," a group of former PayPal employees who have gone on
to become successful entrepreneurs, investors, and executives in the tech industry.
This association further solidifies Rabois's influence and expertise in the startup
and investment spheres.
Early Years and Education
Keith Rabois was born on March 17, 1969, and grew up in
Edison, New Jersey. He pursued his undergraduate studies in political science
at Stanford University, earning his Bachelor of Arts degree in 1991. Later, he
furthered his education by obtaining a Juris Doctor (J.D.) from Harvard Law
School in 1994.
Connections and Controversies
During his time at Stanford, Rabois formed connections that
would shape his future. He crossed paths with Peter Thiel, who was then the
editor and co-founder of The Stanford Review, a libertarian newspaper. Rabois
became involved with the publication, contributing to its content.
However, Rabois's college years weren't without controversy.
He was involved in an incident where he and several other students were
reprimanded for shouting homophobic slurs outside an instructor's home. The
incident included offensive remarks, such as suggesting that the instructor
"die of AIDS." Rabois later explained that the incident was a
deliberate challenge to Stanford's rules regarding student speech.
Support and Defense
Despite the controversy, Rabois found support from Peter
Thiel, who defended him in his book titled "The Diversity Myth:
Multiculturalism and Political Intolerance on Campus." Thiel's defense of
Rabois highlights their enduring connection and Thiel's belief in challenging
prevailing norms and regulations within academic settings.
Early Career Ventures
Following his completion of postgraduate studies, Keith
Rabois embarked on a diverse career path. Initially, he served as a law clerk
for the United States Court of Appeals for the Fifth Circuit for a year.
Subsequently, he spent nearly four years at Sullivan & Cromwell, gaining
valuable experience in the legal field. In 1999, Rabois transitioned into the
realm of politics, serving as an advisor to Dan Quayle's presidential campaign.
Venturing into Information Technology
In the early 2000s, Rabois transitioned into the field of
information technology, marking a pivotal moment in his career trajectory. He
joined PayPal in November 2000, assuming the role of Executive Vice President,
where he oversaw Business Development, Public Affairs, and Policy, contributing
significantly to the company's growth and strategic direction during his
tenure.
LinkedIn and Beyond
From January 2005 to May 2007, Rabois made significant
contributions to LinkedIn, serving as the Vice President for Business and
Corporate Development. This period coincided with LinkedIn's formative years,
and Rabois played a vital role in shaping its business strategies and fostering
key partnerships. LinkedIn, founded by Reid Hoffman, who also had ties to
PayPal, further solidified Rabois's reputation as a discerning executive in the
tech industry.
Joining Square
In 2010, Rabois embarked on a new venture by joining Square,
a pioneering company in electronic payment services, as its Chief Operating
Officer (COO). Despite facing initial setbacks in previous ventures, Rabois
found success at Square, where he played a pivotal role in shaping its
operational framework and driving its growth trajectory. His tenure at Square
underscored his versatility and strategic acumen in navigating the dynamic
landscape of technology startups.
Transition to Venture Capital
After departing from Square in January 2013, Keith Rabois
faced a significant challenge as he encountered allegations of sexual
harassment from an employee. While Rabois maintained that the relationship was
consensual, the threat of a lawsuit prompted his departure. Square acknowledged
Rabois's departure, citing "poor judgment" that hindered his
effectiveness as a leader within the company.
Venture Capital Ventures
In March 2013, Rabois transitioned to the realm of venture
capital, joining Khosla Ventures. However, his tenure at Khosla Ventures
concluded in 2019. During his time there, Rabois assumed various roles,
including serving on the board of directors of Scribd as an observer following
Khosla Ventures' investment in the company in January 2015. Rabois later
returned to Khosla Ventures in January 2024 as one of five managing directors,
signaling a renewed focus on venture capital endeavors.
Founders Fund Involvement
Following his departure from Khosla Ventures in 2019, Rabois
made a significant career move by joining Founders Fund as a general partner.
His tenure at Founders Fund saw the co-founding of OpenStore, a Miami-based
retail-holding startup aimed at acquiring brands within the Shopify ecosystem.
OpenStore garnered substantial attention, raising $75 million at a valuation of
$750 million in 2021.
Ongoing Responsibilities
Despite leaving Founders Fund in January 2024, Rabois
continues to maintain his involvement with the firm. He represents Founders
Fund on the boards of Ramp, Found, and Trade Republic, showcasing his ongoing
commitment to fostering growth and innovation within the startup landscape.
Entrepreneurial Ventures Beyond Venture Capital
Keith Rabois's entrepreneurial spirit extends beyond his
roles in venture capital, encompassing diverse ventures that have made
significant impacts in various industries.
Co-Founding Opendoor
In April 2014, Rabois co-founded Opendoor, a groundbreaking
home buying and selling marketplace. Opendoor revolutionized the real estate
industry by streamlining the process of buying and selling homes, offering
convenience and efficiency to both buyers and sellers. Rabois's involvement in
Opendoor underscores his penchant for disruptive innovation and his ability to
identify opportunities for transformation within traditional markets.
Investment in the Alliance of American Football
In March 2018, Rabois diversified his investment portfolio
by investing in the Alliance of American Football (AAF), a professional
football league. Alongside notable figures such as Peter Thiel and Peter
Chernin, Rabois recognized the potential of the AAF and became a significant
investor in the league. He also assumed a position on the league's board of
directors, contributing his expertise to guide its strategic direction and
growth. Rabois's involvement in the AAF highlights his interest in supporting
ventures across different sectors and his willingness to explore new
opportunities beyond the tech industry.
Political Engagements and Views
Keith Rabois's involvement in politics reflects a diverse
range of engagements and perspectives, demonstrating his active participation in
shaping political discourse.
Contributions to FWD.us
In April 2013, Rabois emerged as a major contributor to
FWD.us, a lobbying group dedicated to advocating for immigration reform and
other policy issues relevant to the tech industry. His support for FWD.us
underscores his commitment to addressing pressing societal issues through
political advocacy and engagement.
Keith Rabois's Midas List Success
Keith Rabois has secured his second appearance on the Midas
List, a prestigious ranking of top venture capitalists. His debut on the list
last year was attributed to his leadership in investments that yielded
significant returns.
Investment Successes
Rabois's notable investments include leading investments in
DoorDash, which went public in 2020, and Affirm, which went public in 2021.
These successes underscore his astute investment strategies and his ability to
identify promising opportunities in the tech sector.
Fintech Triumph with Ramp
Rabois's most remarkable bet is on the fintech startup Ramp,
which experienced a remarkable increase in valuation from $3.9 billion to $8.1
billion following a highly successful Series D funding round in March 2022.
This achievement further solidifies Rabois's reputation as a savvy investor
with a keen eye for disruptive innovations in the fintech landscape.
Entrepreneurial Ventures
Aside from his investment prowess, Rabois is also known for
his entrepreneurial endeavors. He co-founded the online marketplace Opendoor,
which went public via a SPAC (Special Purpose Acquisition Company) in 2020.
This venture exemplifies Rabois's ability to identify market gaps and build
successful ventures to address them.
Rabois is recognized as a Co-Founder and Executive Chairman
of Opendoor, a groundbreaking online marketplace for home buying and selling.
He also holds the position of Co-Founder and Chief Executive Officer at
Openstore, showcasing his leadership in innovative startup ventures. His
entrepreneurial endeavors extend to co-founding Y Ventures, further
highlighting his commitment to driving innovation and growth in the business
landscape.
Role at Founders Fund
As a general partner at Peter Thiel's Founders Fund, Rabois
plays a pivotal role in leading the firm's growing Miami office. His tenure at
Founders Fund follows his previous experience at Khosla Ventures, showcasing
his expertise and leadership in the venture capital landscape.
Member of the "PayPal Mafia"
Rabois's affiliation with the "PayPal Mafia," a
group of former PayPal employees and founders who have gone on to found and develop
other prominent tech companies, further highlights his influential role in the
tech industry. Alongside notable figures such as Peter Thiel and Elon Musk,
Rabois continues to shape the trajectory of the tech sector through his
investments and entrepreneurial pursuits.
Directorships and Board Memberships
Rabois holds key positions as a Director at Affirm and
serves on the boards of Pietra and Trade Republic. His board memberships also
include companies such as Found, The Org, Royal Markets, Forward,
Searchlight.ai, Fam, Eight Sleep, Ghost, Up&Up, Bungalow, Yelp, Xoom, Ramp,
Truework, Teespring, IfOnly, and Even. Additionally, he has served as a Board
Member at companies like Kiddom, Piazza, Ghost Autonomy, and Jetty. His
involvement extends to the Stellar Development Foundation, where he serves as a
Board Member.
Investment and Advisory Roles
In addition to his entrepreneurial pursuits, Rabois is an
active angel investor and serves as a Managing Director at Khosla Ventures,
where his focus areas include consumer Internet, education, enterprise,
financial services, and digital health. He also serves as an Advisor at
Resolute Ventures, providing strategic guidance and support to emerging
startups. Rabois's extensive experience as a litigator at Sullivan and Cromwell
and his previous role as a clerk for the United States Court of Appeals for the
Fifth Circuit underscore his diverse skill set and expertise in navigating
legal and regulatory landscapes.
Past Affiliations
Throughout his career, Rabois has been associated with various companies and organizations, including Cue, Reddit, HealthTap, Homebase, Virtual Kitchen, and the American Football League. His dynamic career trajectory reflects his ongoing commitment to driving innovation, fostering entrepreneurship, and making meaningful contributions across diverse industries.
Political Preferences and Statements
Rabois's political preferences and statements have garnered
attention for their candidness and clarity. In January 2020, he expressed a
preference for voting for Donald Trump over Bernie Sanders, signaling his
alignment with certain political ideologies and priorities. Additionally,
Rabois voiced his support for Pete Buttigieg as his top choice for the
Democratic ticket in the 2019 presidential primaries, showcasing his
willingness to endorse candidates across the political spectrum based on their
policies and leadership qualities.
Recognition of Legislation
In 2023, Rabois publicly praised the Parental Rights in
Education Act law enacted in Florida. His endorsement of this legislation
suggests his approval of policies aimed at addressing specific societal
concerns, highlighting his engagement with political developments at both the
state and national levels. Rabois's recognition of the Parental Rights in
Education Act underscores his involvement in political discourse and his
advocacy for policies aligned with his values and beliefs.
Rabois's contributions to the tech industry have earned him
widespread recognition, consistently placing him on the Forbes Midas list. He
has ranked as high as #4 in the U.S. and #8 globally on this prestigious list,
reflecting his exceptional track record and influence within the technology
investment community. Rabois's continued success and leadership position him as
a driving force behind innovation and growth in the tech sector.
Personal Life
Home Renovation Challenges
In November 2015, Keith Rabois embarked on a significant
personal project by purchasing a house in Glen Park. His plans for renovation
included ambitious additions such as a new penthouse level, a basketball court,
lockers, and a sauna. However, Rabois encountered resistance from six of his
neighbors, indicating the challenges he faced in realizing his vision for his
property.
Marriage and Ceremonial Occasion
In 2018, Rabois celebrated a milestone in his personal life
by marrying Jacob Helberg. The ceremony took place in Saint Barthélemy and was
officiated by Sam Altman, marking a joyous occasion shared with loved ones.
Rabois's marriage highlights the importance of personal relationships and
milestones beyond his professional endeavors.
Relocation to Miami
In November 2020, reports surfaced indicating that Rabois
had made a significant move from California to Miami, Florida. This relocation
underscores his flexibility and willingness to adapt to new environments,
potentially driven by factors such as lifestyle preferences or business
opportunities. Rabois's decision to relocate reflects the dynamic nature of his
personal and professional journey, showcasing his readiness to embrace change
and pursue new opportunities.
Some recent companies where Keith Rabois invested
- Ramp - Financial Software
- Palm Tree Crew – Accessories
- Forward -Clinics/Outpatient
- Roam - Application Software
- Delphi - Business/Productivity Software
- Ghost Atonomy - Business/Production
- Pietra - Business/Productivity Software
- Up&Up - Real Estate Services (B2C)
Also he invested in PayPal, LinkedIn, Square, Opendoor,
Yelp, Xoom, YouTube, Yammer, Palantir, Lyft, AirBnB, Eventbrite and Quora.
Rabois is considered a member of the PayPal Mafia. Rabois has been involved in
investments in YouTube, Palantir Technologies, Lyft, Airbnb, Eventbrite,
wish.com, and theorg.com.
