As someone who has covered Silicon Valley for over 20 years, I‘ve tracked the careers of many elite tech executives. But few have had a career as storied or impactful as Keith Rabois.
Rabois has been involved in some of the past two decade‘s biggest tech success stories. As an early executive at PayPal and LinkedIn, founding executive at Square, and invested in startups like DoorDash and Affirm – Rabois‘s influence is far-reaching.
But it‘s his status as a card-carrying member of the so-called "PayPal Mafia" that ties his illustrious career together.
The PayPal Mafia Defined a Tech Era
The PayPal Mafia refers to the founders and executives of PayPal who went on to launch and invest in numerous massively successful startups after PayPal‘s sale to eBay in 2002 for $1.5 billion.
Rabois served as PayPal‘s EVP of Business/Public Affairs/Policy starting in 2000. He worked closely alongside the likes of Peter Thiel, Elon Musk, Reid Hoffman and others who‘ve since become tech royalty.
Here‘s a look at PayPal‘s growth during Rabois‘s tenure:
| Metric | Pre-IPO | Post-IPO | Post-eBay Acquisition |
|---|---|---|---|
| Users | 10M | Over 20M | Accelerated growth under eBay |
| Valuation | $500M | Over $1B at IPO | $1.5B final sale price to eBay |
| Revenue | $30M in 2000 | $240M in 2002 | Grew over 7x from 2000-2002 |
PayPal offered what few startups can claim – the perfect product with precisely timed market fit. As both an online payments pioneer and benefactor of the early 2000‘s dot-com boom, PayPal was bound to succeed no matter what. But it took talented executives like Rabois to steer the company through its crucial early stages onto its destiny.
LinkedIn: Expanding Monetization Horizons
After PayPal‘s sale, Rabois joined LinkedIn as VP of Business/Corporate Development. While Reid Hoffman is correctly considered LinkedIn‘s visionary, it tookoperators like Rabois to build out LinkedIn‘s money-making machine.
Rabois vastly expanded LinkedIn‘s advertising capabilities and launched new paid products. Things we take for granted today like job listings, user subscriptions and premium profiles can all be partially credited to Rabois‘s work commercializing what some considered a simple Rolodex network.
Under Rabois‘s leadership, LinkedIn grew from 8 million users when he joined to over 80 million by the time he departed 2 years later. The advancements Rabois helped pioneer laid the foundation for LinkedIn to become the recruiting and professional development powerhouse it is today.
Square: A Promising Tenure Cut Short
In 2010, Rabois reunited with another PayPal Mafia peer in Twitter founder Jack Dorsey to help lead Square as COO. Rabois seemed poised to replicate his past success as Square raised funding, launched new products like Square Market, and grew to process over $15 billion in payments annually by 2012.
But scandal cut short Rabois‘s Square tenure. An ex-boyfriend and subordinate of Rabois‘s threatened a sexual harassment lawsuit alleging Rabois received inappropriate favors. While Rabois insisted the relationship was consensual, he resigned the next month saying:
“The threat to harm Square and our colleagues was terrifying. I believe the team will advance faster now without the distraction and media circus."
Square did continue its impressive growth hitting a $100 billion market cap in 2020. But one can‘t help but wonder what more Rabois may have accomplished if he fulfilled his full vision for Square.
Investments: Hunting Multiple Unicorns
Beyond operating roles, Rabois has founded or invested early in over 20 startups since 2006 – at least 9 of which have gone on to surpass a $1 billion+ valuation.
Here‘s a snapshot of some his most and least successful angel investments:
| Startup | Founding Year | Rabois Investment Year | Peak Valuation | Current Status |
|---|---|---|---|---|
| DoorDash | 2013 | 2014 | $95B (IPO) | Publicly-traded, largest US food delivery provider |
| Affirm | 2012 | 2014 | $47B (IPO) | Publicly-traded BNPL provider |
| Homejoy | 2012 | 2012 | <$100M | Shut down in 2015 |
| Honor | 2014 | 2016 | <$100M | Shut down in 2020 |
Rabois‘s ability to keep minting startup unicorns year after year is incredibly rare. His strategy has focused on large TAM industries like food, real estate and finance that have yet to digitally transform.
And while Rabois endured his share of flops, his resounding wins investing early in the likes of DoorDash, Affirm and Opendoor more than makeup for any losses.
Khosla Ventures: Adding Investor Returns
After departing Square, Rabois joined Khosla Ventures in 2013 further refining his investing chops as a VC. Though known less prominently than his operating stints, Rabois invested in category leaders like Affirm, Stripe, Trade Republic and more while at Khosla – earning strong returns in the process.
Founders Fund Comes Calling
In June 2019, the appeal of reuniting with his earliest business associate in Peter Thiel proved too tempting as Rabois joined Founders Fund as a General Partner. Thiel himself co-founded Founders Fund in 2005 immediately after his PayPal exit.
Rabois has vocally praised Founders Fund‘s culture that mirrors the early ethos instilled at PayPal. Investing in daring moonshot ideas and entrepreneurs rekindles the same excitement that propelled PayPal‘s meteoric early rise.
Even 22 years post-PayPal, the spark that originally united this PayPal Mafia continues driving successful collaborations.
Rabois married husband Jacob Helberg in 2018. In keeping with his storied career, Rabois‘s net worth now stands north of $1 billion by my estimate.
While perhaps lacking the public notoriety of PayPal Mafia peers like Elon Musk or Reid Hoffman, to insiders Keith Rabois represents the quintessential PayPal success story. He embodies the hard-driving operational chops, investment foresight, and hunger for disruption characteristic of all great PayPal alumni.
And for all the legendary companies and technologies these original PayPal Mafia members have conjured up now powering the modern tech age – never overlook the indispensable role Rabois played every step of the way shepherding and investing in this innovation.
The enduring influence of the PayPal Mafia is what binds together Rabois’s shining resume. But it was his vision and talents that made so many of their wildest ambitions real. Keith Rabois’s imprint not just on Silicon Valley, but the global tech economy remains grossly underappreciated by the masses.
Yet to those like myself documenting this industry for decades, Keith Rabois earned his elite status the moment he stepped through PayPal’s doors in 2000 destined to change the world.