YESTERDAY

About

Biographies

Kevin Hartz - The Early Stories Behind Billions

By: Kyan Yang ・ 12 min read

A Town Called Orinda

Take Ashby Avenue east out of Alta Bates Hospital, past the clamor of Berkeley’s campus and into the three yawning bores of the Caldecott Tunnel. The atmosphere shifts when you emerge on the other side of the Oakland Hills, away from the “cool, hipster side” of Berkeley and into the “WASPy, middle class, idyllic little neighborhoods and towns.” The fog shrinks away. The air dries out. The eucalyptus trees give away to manicured cul-de-sacs and backyard pools reflecting the California sun. This is where Kevin Hartz’s early stories were born—in “a town called Orinda.”

It was the early 1970s. Orinda had two private high schools and one public—Miramonte High. The town offered a picture-perfect “Americana childhood,” the kind where bikes lay scattered across trimmed lawns and front doors stayed unlocked. Most neighbors shared the same split-level architecture and the same Republican politics, though with the exception of one outlier—the Hartz family.

Kevin’s parents met at a Democratic Party function in San Francisco, and brought that political alignment across the Bay. In Orinda, they “were the one standout weird, strange liberals in town.” It wasn’t at all a divisive identity, but it would provide Kevin an avenue to develop his rebellious character, as his young engagement in local Democratic campaigns accustomed him to deviating from the norm. For what it’s worth, “if you were a Democrat in [1970s] Orinda, you were a rebel.”


⎯


For the Hartz family, deviating from the norm was a prevalent theme. In the mid to late 1970s, between Kevin’s first and fourth grade, the family left Orinda for a stint in Miami. His father had taken a job as general counsel for a regional bank—a benign-sounding position, except that this was the money-laundering, cocaine capital Miami of the late 70s. The family would later refer to it, half-jokingly, as their “sketchy Miami years.” Nothing happened of course (his dad “literally was a Boy Scout”), but the story wrote itself. A lawyer at a Miami bank in the middle of a cartel gold rush—“the fact set was just so suspicious.”


Miami, for an elementary school Kevin, was paradise. Days were spent “on the bike... or at the beach... or in the water.” There was a looseness to life there, unstructured and wide open. And something of that stayed with him when the family moved back to Orinda in 1980—something restless and eager.


It reemerged in the backyard, in demolitions that were both impressive feats of construction and concerning hobbies for a teenager to engage in. As a “pyromaniac” by his own words, he’d “make model boats, and so on, and put them in the pool and blow them up.”


“My dad would just be like, ‘What’s wrong with that kid?’”


But Kevin wasn’t content with simple explosions. He and his friends at Miramonte High started producing films, such as the stop-motion spectacle Murder in Smurf Land, where Smurfs were obliterated in “all sorts of ways.” Indeed, “it sounded like a very kind of violent and tormented childhood.” But maybe that was just what founders did back then, as “the [original] PayPal crew had all made bombs in high school too.”


By their senior year in 1987-1988, the Murder in Smurf Land group’s plots grew more sophisticated. As Miramonte High’s Senior Cut Day approached, the group—being in the student body leadership—decided to give it official sanction. They drafted a school-wide letter announcing a formal closure, citing a suspicious “specus” found in the walls. And with their access to student government documents, they forged signatures, printed official notices, and mailed the copies using the school’s own nonprofit postage.


The execution was perfect. Students stayed home and faculty “was left up in arms,” but the crew had one small oversight—the letter was too well-written to be believed by some members of administration. The forgery was caught, and Kevin faced five days of suspension on top of being barred from attending his school’s commencement ceremony. Though—that wasn’t nearly enough to deter his rebellious spirit. To Kevin, the “[experience] was good fun.”

A Town Called Orinda

Take Ashby Avenue east out of Alta Bates Hospital, past the clamor of Berkeley’s campus and into the three yawning bores of the Caldecott Tunnel. The atmosphere shifts when you emerge on the other side of the Oakland Hills, away from the “cool, hipster side” of Berkeley and into the “WASPy, middle class, idyllic little neighborhoods and towns.” The fog shrinks away. The air dries out. The eucalyptus trees give away to manicured cul-de-sacs and backyard pools reflecting the California sun. This is where Kevin Hartz’s early stories were born—in “a town called Orinda.”


It was the early 1970s. Orinda had two private high schools and one public—Miramonte High. The town offered a picture-perfect “Americana childhood,” the kind where bikes lay scattered across trimmed lawns and front doors stayed unlocked. Most neighbors shared the same split-level architecture and the same Republican politics, though with the exception of one outlier—the Hartz family.


Kevin’s parents met at a Democratic Party function in San Francisco, and brought that political alignment across the Bay. In Orinda, they “were the one standout weird, strange liberals in town.” It wasn’t at all a divisive identity, but it would provide Kevin an avenue to develop his rebellious character, as his young engagement in local Democratic campaigns accustomed him to deviating from the norm. For what it’s worth, “if you were a Democrat in [1970s] Orinda, you were a rebel.”


⎯


For the Hartz family, deviating from the norm was a prevalent theme. In the mid to late 1970s, between Kevin’s first and fourth grade, the family left Orinda for a stint in Miami. His father had taken a job as general counsel for a regional bank—a benign-sounding position, except that this was the money-laundering, cocaine capital Miami of the late 70s. The family would later refer to it, half-jokingly, as their “sketchy Miami years.” Nothing happened of course (his dad “literally was a Boy Scout”), but the story wrote itself. A lawyer at a Miami bank in the middle of a cartel gold rush—“the fact set was just so suspicious.”


Miami, for an elementary school Kevin, was paradise. Days were spent “on the bike... or at the beach... or in the water.” There was a looseness to life there, unstructured and wide open. And something of that stayed with him when the family moved back to Orinda in 1980—something restless and eager.


It reemerged in the backyard, in demolitions that were both impressive feats of construction and concerning hobbies for a teenager to engage in. As a “pyromaniac” by his own words, he’d “make model boats, and so on, and put them in the pool and blow them up.”


“My dad would just be like, ‘What’s wrong with that kid?’”


But Kevin wasn’t content with simple explosions. He and his friends at Miramonte High started producing films, such as the stop-motion spectacle Murder in Smurf Land, where Smurfs were obliterated in “all sorts of ways.” Indeed, “it sounded like a very kind of violent and tormented childhood.” But maybe that was just what founders did back then, as “the [original] PayPal crew had all made bombs in high school too.”


By their senior year in 1987-1988, the Murder in Smurf Land group’s plots grew more sophisticated. As Miramonte High’s Senior Cut Day approached, the group—being in the student body leadership—decided to give it official sanction. They drafted a school-wide letter announcing a formal closure, citing a suspicious “specus” found in the walls. And with their access to student government documents, they forged signatures, printed official notices, and mailed the copies using the school’s own nonprofit postage.


The execution was perfect. Students stayed home and faculty “was left up in arms,” but the crew had one small oversight—the letter was too well-written to be believed by some members of administration. The forgery was caught, and Kevin faced five days of suspension on top of being barred from attending his school’s commencement ceremony. Though—that wasn’t nearly enough to deter his rebellious spirit. To Kevin, the “[experience] was good fun.”

Stanford Days and Meeting the PayPal Mafia

The autumn of 1988 Palo Alto brought a stable, cooler temperature compared to the Orindan extremes. Under sun-warmed terracotta roof tiles, sandstone arches beckoned toward Canary Island Palms that casted long shadows across the main quad. Most students scrambled to secure their status in the economics department, while a curious few explored computer science—a burgeoning major as Silicon Valley tech ambition grew alongside the IPOs of Apple, Microsoft, and other emerging giants.


But Kevin’s rebellious spirit brought him down a different route. He double majored in history and applied earth sciences—a rare, “N of one” pairing born from his ambitions to “save the environment and save the world.” And in a staunch continuation of his political involvement back in Orinda, he also ventured into Stanford’s ASSU Undergraduate Senate.


⎯


Kevin was still a freshman senator when he first crossed paths with Peter Thiel, an ambitious graduate senator with a “sharp eye for talent.” It was through that eye in which a student politics friend group coalesced: Peter, Keith Rabois, David Sacks, a handful of other soon-to-be “PayPal mafia” members, and Kevin—their “token liberal friend.”


But there was “no commercial orientation.” Just lofty ideals and the shared conviction to “make a positive impact on the world.” They debated topics like curriculum reform and Affirmative Action amidst the “first big push to change Western civilization,” and they took on internships in the Capitol through Stanford in Washington. The group was a close-knit, “heavy concentration of talent,” and they fed off each other in a way that would go on to produce revolutionary thinkers.


Outside the student senate chambers, Kevin’s pyromaniacal, thrill-seeking instincts were able to resurface in Greek Life. Spring quarter brought fraternity rush, and the fraternity houses staged what could only be described as “barbaric hazing.” Chaotic and relentlessly thrilling, Greek Life gave Kevin a necessary counterbalance to the structured form of student government—a way to continue feeding the rebellious and daring nature in him, though the brotherhood was definitely “more fun than [he’d] like to admit.”

Stanford and Meeting the PayPal Mafia

The autumn of 1988 Palo Alto brought a stable, cooler temperature compared to the Orindan extremes. Under sun-warmed terracotta roof tiles, sandstone arches beckoned toward Canary Island Palms that casted long shadows across the main quad. Most students scrambled to secure their status in the economics department, while a curious few explored computer science—a burgeoning major as Silicon Valley tech ambition grew alongside the IPOs of Apple, Microsoft, and other emerging giants.


But Kevin’s rebellious spirit brought him down a different route. He double majored in history and applied earth sciences—a rare, “N of one” pairing born from his ambitions to “save the environment and save the world.” And in a staunch continuation of his political involvement back in Orinda, he also ventured into Stanford’s ASSU Undergraduate Senate.


⎯


Kevin was still a freshman senator when he first crossed paths with Peter Thiel, an ambitious graduate senator with a “sharp eye for talent.” It was through that eye in which a student politics friend group coalesced: Peter, Keith Rabois, David Sacks, a handful of other soon-to-be “PayPal mafia” members, and Kevin—their “token liberal friend.”


But there was “no commercial orientation.” Just lofty ideals and the shared conviction to “make a positive impact on the world.” They debated topics like curriculum reform and Affirmative Action amidst the “first big push to change Western civilization,” and they took on internships in the Capitol through Stanford in Washington. The group was a close-knit, “heavy concentration of talent,” and they fed off each other in a way that would go on to produce revolutionary thinkers.


Outside the student senate chambers, Kevin’s pyromaniacal, thrill-seeking instincts were able to resurface in Greek Life. Spring quarter brought fraternity rush, and the fraternity houses staged what could only be described as “barbaric hazing.” Chaotic and relentlessly thrilling, Greek Life gave Kevin a necessary counterbalance to the structured form of student government—a way to continue feeding the rebellious and daring nature in him, though the brotherhood was definitely “more fun than [he’d] like to admit.”

Oxford and Early Career Exploration

In 1992, after four years of student politics and fraternity bonding, Kevin traveled across the Atlantic to study in the stone buildings and cobbled quads of Oxford. It was an “incredible, beautiful place” where the weight of history hung in the air. For Kevin, it was a return to principle—a chance to “delve a bit more into the history side of things,” because “what better place than in Oxford?” He attended University College (the same college that had taken in Bill Clinton during his Rhodes years), where he studied under renowned faculty and met extraordinary peers, including a future Supreme Court justice with whom he wished he stayed in better contact with.

Oxford gave Kevin time to reflect. But in 1993, after just a year abroad, he finished his Masters in History and came back to the states uncertain what to pursue next. It was “easy to take the LSATs and … apply to law school,” but he had also completed many premed requirements during his Stanford years.

Kevin took an interest in pursuing medical school, which led him to work “in this eye research lab … where we’d put them [Rhesus monkeys] in front of a screen and have them follow a dot.” They “effectively [had] a BCI—an electrode in their brains that [was] measuring … this area called the superior caliculi” (the part of the midbrain responsible for visual reflexes). And by “following this dot in a screen, you could coordinate it with the firing of these neurons and better understand the brain.”

⎯


But his lab research years were also important years of transition, both in his own life and in the wider world around him. It was 1994—everyone in the lab worked on Unix systems, and “the first web browser [Mosaic] had come out.” Names were beginning to float into conversation—Marc Andreessen, Jim Clark—as Kevin started to see his Stanford friends “go to these different companies [like] Netscape and Silicon Graphics.”

The Valley had begun its gravitational pull, and Kevin was no exception to this migration. As 1995 drew to a close, he joined Silicon Graphics as a product manager—a company that, at the time, was at the forefront of 3D graphics and visualization.

But Kevin’s ambitious spirit sought more. His curiosity wandered towards more thrilling ventures, and just after his second anniversary at Silicon Graphics, Kevin left the company to “meet up with a few friends from Stanford.” With this new team, Kevin would begin his journey into the start-up space.

Oxford and Early Career Exploration

In 1992, after four years of student politics and fraternity bonding, Kevin traveled across the Atlantic to study in the stone buildings and cobbled quads of Oxford. It was an “incredible, beautiful place” where the weight of history hung in the air. For Kevin, it was a return to principle—a chance to “delve a bit more into the history side of things,” because “what better place than in Oxford?” He attended University College (the same college that had taken in Bill Clinton during his Rhodes years), where he studied under renowned faculty and met extraordinary peers, including a future Supreme Court justice with whom he wished he stayed in better contact with.


Oxford gave Kevin time to reflect. But in 1993, after just a year abroad, he finished his Masters in History and came back to the states uncertain what to pursue next. It was “easy to take the LSATs and … apply to law school,” but he had also completed many premed requirements during his Stanford years.


Kevin took an interest in pursuing medical school, which led him to work “in this eye research lab … where we’d put them [Rhesus monkeys] in front of a screen and have them follow a dot.” They “effectively [had] a BCI—an electrode in their brains that [was] measuring … this area called the superior caliculi” (the part of the midbrain responsible for visual reflexes). And by “following this dot in a screen, you could coordinate it with the firing of these neurons and better understand the brain.”


⎯


But his lab research years were also important years of transition, both in his own life and in the wider world around him. It was 1994—everyone in the lab worked on Unix systems, and “the first web browser [Mosaic] had come out.” Names were beginning to float into conversation—Marc Andreessen, Jim Clark—as Kevin started to see his Stanford friends “go to these different companies [like] Netscape and Silicon Graphics.”


The Valley had begun its gravitational pull, and Kevin was no exception to this migration. As 1995 drew to a close, he joined Silicon Graphics as a product manager—a company that, at the time, was at the forefront of 3D graphics and visualization.


But Kevin’s ambitious spirit sought more. His curiosity wandered towards more thrilling ventures, and just after his second anniversary at Silicon Graphics, Kevin left the company to “meet up with a few friends from Stanford.” With this new team, Kevin would begin his journey into the start-up space.

A Quick Flip

The internet was rapidly growing in ‘97—about a third of homes owned a desktop, though mobile devices and laptops were still a business-class luxury. But even with a laptop, finding internet on the road was its own challenge. A business traveller checking into a hotel might be met with a dial-up desk phone and a coaxial TV with pay-per-view listings—and if there was internet access at all, it came through dial-up modems that whined with painfully slow connections, assuming you brought the right adapter.

High-speed internet was still something you found at university labs or corporate IT departments, not at a Marriott in downtown San Jose.

But the demand was growing. As office work grew faster, more connected, and more reliant on the web, the call traffic from business travelers began overloading hotels’ PBX systems. There was a gap in service and demand, and Kevin—with the Stanford friends he’d met up with—moved quickly.

They began “wiring up hotels with high-speed internet access” under the name “Connect Group.” Floor by floor, room by room, they installed Ethernet ports and ran cables behind the drywall. Guests could now plug in, access the internet without software installation or configuration, and get 50x the internet speed of traditional modems.

And in just a few months time, Lodgenet—a public, in-room entertainment company based out of Sioux Falls—offered an acquisition deal of 5 million in stock (almost 10 million dollars today).

In a clean, “quick flip,” Kevin had sold his first company. He’d gotten his first taste of how fast things moved in the tech startup world, and it left him “hungry” in the way only Silicon Valley can make a person hungry.

⎯


Kevin had finally found his passion in tech, and he would only become “further and further enamored” after taking on a Principal role at Outlook Ventures—a firm focused on early stage enterprise software startups. It offered a place to land after the rush of his first exit, where he could invest, observe, and plan for what came next. But the momentum wouldn’t last.

A Quick Flip

The internet was rapidly growing in ‘97—about a third of homes owned a desktop, though mobile devices and laptops were still a business-class luxury. But even with a laptop, finding internet on the road was its own challenge. A business traveller checking into a hotel might be met with a dial-up desk phone and a coaxial TV with pay-per-view listings—and if there was internet access at all, it came through dial-up modems that whined with painfully slow connections, assuming you brought the right adapter.


High-speed internet was still something you found at university labs or corporate IT departments, not at a Marriott in downtown San Jose.


But the demand was growing. As office work grew faster, more connected, and more reliant on the web, the call traffic from business travelers began overloading hotels’ PBX systems. There was a gap in service and demand, and Kevin—with the Stanford friends he’d met up with—moved quickly.


They began “wiring up hotels with high-speed internet access” under the name “Connect Group.” Floor by floor, room by room, they installed Ethernet ports and ran cables behind the drywall. Guests could now plug in, access the internet without software installation or configuration, and get 50x the internet speed of traditional modems.


And in just a few months time, Lodgenet—a public, in-room entertainment company based out of Sioux Falls—offered an acquisition deal of 5 million in stock (almost 10 million dollars today).


In a clean, “quick flip,” Kevin had sold his first company. He’d gotten his first taste of how fast things moved in the tech startup world, and it left him “hungry” in the way only Silicon Valley can make a person hungry.


⎯


Kevin had finally found his passion in tech, and he would only become “further and further enamored” after taking on a Principal role at Outlook Ventures—a firm focused on early stage enterprise software startups. It offered a place to land after the rush of his first exit, where he could invest, observe, and plan for what came next. But the momentum wouldn’t last.

Founding Xoom and Lessons on Talent

In the Spring of 2000, the dot-com bubble burst. Startups frantically auctioned off ping-pong tables and ergonomic Aeron chairs, as reservation waitlists at fancy restaurants disappeared within days. Highway 101 traffic began to ease in the following months, and “the economy was in tatters.”

But the founders and engineers that were truly passionate about tech stayed. And one of those teams was PayPal.

A couple years earlier—during Kevin’s Connect Group days—Peter Thiel flew from New York back to Palo Alto, drawn by the startup heat in the Valley after his brief explorations in law and finance. He was no longer the graduate student senator with a “sharp eye for talent,” but an early-stage investor giving talks at Stanford and looking to claim his piece of the dot com gold rush.

⎯


In 1998, during one of Peter’s guest lectures on campus, a twenty-three year old recent UIUC graduate, Max Levchin, happened to be in the audience. The two “hit it off” almost immediately and, after rounding out their team with two other friends, built the first iterations of what would later become PayPal. It started with “smart tokens or VP … some kind of security over early mobile devices,” but evolved rapidly. They narrowed in on money transfers, rebranded to ‘PayPal’ the year after, and before long, it had become “very clear [they] were winning” the digital payments space.

Kevin had been watching closely. It was “always … [part of] a playbook to build adjunct to [winning companies]”—and so in August of 2001, Kevin left Outlook Ventures alongside his coworker Alan Braverman, sketching out the blueprints for what would become Xoom.

Less than a month passed before tragedy struck the nation. In an already “tattered economy” from the ongoing dot-bust, the nation fell into silence. Families mourned lost loved ones, and the economy halted as stock exchanges closed for several days. But Kevin could not be deterred. Alongside Alan, the two moved relentlessly, building “in the wake of 9/11” and becoming “the first developers on the PayPal API.” It was a gamble taken during a moment when the world felt unprecedentedly uncertain—though Kevin knew the one constant they could always rely on. Extraordinary talent. And in an effort to find the best talent possible, he turned to the legendary “talent wrangler”—Peterson Goodwyn Powell Conway VIII.

⎯


Peterson Conway had built a name for himself in the recruiting world through the “gift … in his character” and “his way of engaging great talent.” But seeing potential in Kevin and Alan, he “put his recruiting business on hold to become [Xoom’s] primary relationship-builder,” assembling talent for their early teams and flying internationally to establish partnerships with foreign money transmission networks. He was “a colorful character [who was] just a lot of fun to work with”—being unconventional, memorable, and “an amateur pilot … [who] also lands planes on freeways,” among “many other things.”

One of those things was the set of “clever tactics [he used] to really engage top talent and make it fun.”

Engineers “love things like airplanes,” so Peterson would “take them up in his Cessna [and] fly around” the California landscapes, or sometimes “down to Mojave to watch test launches [and] see things blow up”—a spectacle that Orindan Kevin certainly would’ve enjoyed. And during Peterson’s later time at Palantir, he would gamify the interview process by sending out “these embossed, fancy letters that said, ‘You’ve been selected as a top student at MIT’ or ‘top student at Harvard,’ ‘to have the right to [interview at Palantir]’.”


Kevin would later learn from other mentors as well, one notable one being Pierre Lamond. Contrasted to Peterson, Pierre was “hard-driving.” As a physicist from the semiconductor industry and a foundational partner at Sequoia, he was “very wise and … very engineering-centric,” leading unforgettable changes from his first day at Xoom. On that day, Pierre had instructed Kevin to “force rank the E-staff … on a whiteboard.” And when Kevin finished, Pierre “grabbed the pen, walked up, crossed off the bottom two, and said, ‘Fire those two.’”

It was “a revelation” for Kevin. While harsh by modern standards, it made intuitive sense to him: “If everything depends on talent, and you have someone [being the] lowest in there—it's something to really think about.”


Xoom grew steadily through these lessons and strategies, and in 2005, Kevin “moved out of [his] full-time role, relatively early in [Xoom’s] life.” By then, he’d already accrued enough wealth to retire both himself and his then fiance, Julia. But the Oridian restlessness was still there. It wasn’t “a money thing, or anything else” of the sort. There was just that hunger to “build things and do things with really bright people.” And so he would.

Founding Xoom and Lessons on Talent

In the Spring of 2000, the dot-com bubble burst. Startups frantically auctioned off ping-pong tables and ergonomic Aeron chairs, as reservation waitlists at fancy restaurants disappeared within days. Highway 101 traffic began to ease in the following months, and “the economy was in tatters.”


But the founders and engineers that were truly passionate about tech stayed. And one of those teams was PayPal.


A couple years earlier—during Kevin’s Connect Group days—Peter Thiel flew from New York back to Palo Alto, drawn by the startup heat in the Valley after his brief explorations in law and finance. He was no longer the graduate student senator with a “sharp eye for talent,” but an early-stage investor giving talks at Stanford and looking to claim his piece of the dot com gold rush.


⎯


In 1998, during one of Peter’s guest lectures on campus, a twenty-three year old recent UIUC graduate, Max Levchin, happened to be in the audience. The two “hit it off” almost immediately and, after rounding out their team with two other friends, built the first iterations of what would later become PayPal. It started with “smart tokens or VP … some kind of security over early mobile devices,” but evolved rapidly. They narrowed in on money transfers, rebranded to ‘PayPal’ the year after, and before long, it had become “very clear [they] were winning” the digital payments space.


Kevin had been watching closely. It was “always … [part of] a playbook to build adjunct to [winning companies]”—and so in August of 2001, Kevin left Outlook Ventures alongside his coworker Alan Braverman, sketching out the blueprints for what would become Xoom.

Less than a month passed before tragedy struck the nation. In an already “tattered economy” from the ongoing dot-bust, the nation fell into silence. Families mourned lost loved ones, and the economy halted as stock exchanges closed for several days. But Kevin could not be deterred. Alongside Alan, the two moved relentlessly, building “in the wake of 9/11” and becoming “the first developers on the PayPal API.” It was a gamble taken during a moment when the world felt unprecedentedly uncertain—though Kevin knew the one constant they could always rely on. Extraordinary talent. And in an effort to find the best talent possible, he turned to the legendary “talent wrangler”—Peterson Goodwyn Powell Conway VIII.


⎯


Peterson Conway had built a name for himself in the recruiting world through the “gift … in his character” and “his way of engaging great talent.” But seeing potential in Kevin and Alan, he “put his recruiting business on hold to become [Xoom’s] primary relationship-builder,” assembling talent for their early teams and flying internationally to establish partnerships with foreign money transmission networks. He was “a colorful character [who was] just a lot of fun to work with”—being unconventional, memorable, and “an amateur pilot … [who] also lands planes on freeways,” among “many other things.”


One of those things was the set of “clever tactics [he used] to really engage top talent and make it fun.”


Engineers “love things like airplanes,” so Peterson would “take them up in his Cessna [and] fly around” the California landscapes, or sometimes “down to Mojave to watch test launches [and] see things blow up”—a spectacle that Orindan Kevin certainly would’ve enjoyed. And during Peterson’s later time at Palantir, he would gamify the interview process by sending out “these embossed, fancy letters that said, ‘You’ve been selected as a top student at MIT’ or ‘top student at Harvard,’ ‘to have the right to [interview at Palantir]’.”


Kevin would later learn from other mentors as well, one notable one being Pierre Lamond. Contrasted to Peterson, Pierre was “hard-driving.” As a physicist from the semiconductor industry and a foundational partner at Sequoia, he was “very wise and … very engineering-centric,” leading unforgettable changes from his first day at Xoom. On that day, Pierre had instructed Kevin to “force rank the E-staff … on a whiteboard.” And when Kevin finished, Pierre “grabbed the pen, walked up, crossed off the bottom two, and said, ‘Fire those two.’”

It was “a revelation” for Kevin. While harsh by modern standards, it made intuitive sense to him: “If everything depends on talent, and you have someone [being the] lowest in there—it's something to really think about.”


Xoom grew steadily through these lessons and strategies, and in 2005, Kevin “moved out of [his] full-time role, relatively early in [Xoom’s] life.” By then, he’d already accrued enough wealth to retire both himself and his then fiance, Julia. But the Oridian restlessness was still there. It wasn’t “a money thing, or anything else” of the sort. There was just that hunger to “build things and do things with really bright people.” And so he would.

Eventbrite and Airbnb Rivalry

By now, the dot-com hangover had finally lifted enough for a new kind of optimism to emerge in the Valley. It was post-Web 2.0 online communities and user-generated everything—a belief that if Flickr could turn photos social, then anything could be turned social.

Kevin, immediately after leaving Xoom in 2005, carried his adventurous spirit two blocks south to a second-floor space that smelled of plywood and fresh drywall. In that shared San Francisco office which borne both wedding plans and wireframes, Kevin and his then fiance, Julia, sketched the blueprint for their “next big adventure.” They would bring in technical cofounder Renaud Visage, together building what would become Eventbrite.

It went against conventional wisdom—never start a business with your friend, let alone family. Even Kevin’s own parents’ who “have always loved each other their entire X number of years” could “never work together.” There was just a “different calculus” required for professional partnership, one that had to “kind of be tested out.”

But neither partner’s rebellious spirit would be deterred. They set up the guidepost—that if the venture ever strained their marriage, one “would step out or do something else.” And with that guardrail in place, they “kept going and going and going”—and against all odds, it “just kept working and working.”

A year passed, and it was clear the newly married Kevin and Julia complemented each other perfectly. They were both relentless, and they both understood that about each other. Day by day, the pair would match each other’s obsession—with Julia not even pausing in the delivery room, answering customer service emails until a worried nurse had to wrestle the laptop out of her hands.


⎯


Just down the street from Eventbrite, an industrial designer named Brian Chesky had just moved in. Because the Valley rent outpaced his savings, Brian began filling his space with air mattresses and subletting to short-term guests—a business that would soon turn into Airbnb.

In 2009, Kevin would take interest in the host-and-guest platform, investing during Airbnb’s Sequoia round after they came out of YC. And apart from just being two blocks away from each other, both Eventbrite and Airbnb were GMV-driven businesses with “similar formats” and “around the same net revenue,” inciting “these revenue wars” that challenged the two startups to outgrow one another.

Eventbrite would pull ahead for a moment later that year. But Airbnb had incredible network effects, and “as soon as those network effects took hold, the numbers on the Airbnb side just skyrocketed.” Eventbrite was still growing at a solid pace, but the Airbnb numbers were just “magical.” Kevin had lost the competition, feeling “depressed for about five minutes” before being “very happy” for the success of Brian and Airbnb.

But Kevin’s interest in promising ventures wasn’t limited to Airbnb. In 2010, he backed Pinterest at their seed after being introduced to Silbermann and Sciarra through Ed Baker—an “amazing growth person” from Facebook, Uber, and later Aura. Kevin had also known Uber’s founder Travis Kalanick since his Red Swoosh days, investing in Uber during their 2011 Series B.


⎯


By now, Kevin had established a legendary reputation for himself. From co-founding three highly successful companies to successfully betting on what became era-defining companies, Kevin had an undefeated intuition and an insatiable hunger to match. And with the ever growing network that followed, Kevin would institutionalize future investments into his fourth company—A*.

Investments and Sauron

In the modern venture landscape, where funds are being saturated with startups that parrot the “Peter Thiel competition is for losers” mantra but still dive into a Red Ocean, Kevin Hartz emphasizes collaboration—since “the sum is greater than the parts.”

He partnered with Godam and Bennett, more measured investors who balanced out Kevin’s “impulse to shoot from the hip.” Together, they formed A*, an early stage venture capital firm that stood out for being “a collaborative group.” And they approached partnership differently—rather than having a singular lead partner per deal, the entire A* team would work together “on all aspects of understanding the founders and [their] business.”

This collective immersion also meant more selectivity. A* was more “kind of snipers versus a bazooka,” backing ventures like Decagon’s AI customer service, WHOP’s creator tools, and Cape’s “cloaked cell phone,” which Kevin believes might be “the future of telecom infrastructure.”

⎯


But Sauron’s origins came differently. A mutual friend at Waymo introduced Kevin and Jack Abraham (from Atomic) to Vasu—a roboticist with a Zipline pedigree and PhD focused on self-driving cars. The three had seen “all this investment and work done in self-driving cars,” and wondered where else the tech could be applied.

The team would then come across a realization after an intruder broke into the Hartz house. Kevin and Julia had “two different systems installed—and neither detected this person.” It was only when the assailant tried to “push their way into the neighbor’s house,” that police came and swarmed the street. Kevin would then realize—that amid all the tech innovation of the 20s, “there’s been zero innovation” in the home security space since Ring. And so the Orindan serial entrepreneur, together with Vasu and Jack, co-founded his fifth and most recent company, Sauron.

Mentorship and Life Lessons

There was a common theme between each adventure—from wiring up hotels for Connect Group, building international money transfer networks at Xoom, or guiding early-stage startups with A*. No matter where he went, Kevin had always been drawn to “extraordinary people who [were doing] extraordinary new things.” He had learned it was “best not to be focused on a particular technology,” but instead to be “focused on people.”


Kevin’s people oriented mindset guided his investments too. When evaluating a “seed-stage company—especially first-time founders—they don’t have a rich history you can pattern match on.” So instead Kevin would ask them “about their families and their parents and their siblings—how competitive they are, how intellectually oriented they are.”


And there was a particular grit that Kevin would notice among founders who were first-generation immigrants. Traveling across borders and coming to the U.S., they had “overcome a lot of obstacles to do great things.” They had “this edge—this drive to want to win and work harder than everyone else.”


But then there were the “really extraordinary people” like Peter Thiel. He was not only “smarter than everyone at Stanford,” but also “had a different way of seeing the world”—the “added sort of X factor which makes him an N of one.”


Peter was one of many mentor figures to Kevin—with Peter’s “few words and insights” being “really impactful and incredible,” Roelof Botha serving on the board at Xoom and Eventbrite for more than a decade each, and Pierre Lamond teaching hard personnel decisions with a single whiteboard exercise.

⎯

These mentors guided Kevin throughout his career, helping him avoid common entrepreneurial pitfalls. The one regret Kevin did have, though, “revolved around not staying the course or enduring things for a longer period of time.” It was back in 2015, when Xoom’s billion-dollar sale to PayPal had seemed like “a great outcome” in the moment—but “fast forward ten years,” and the market “just kept getting bigger and bigger.” And now in 2025, Remitly and Wise—two small Xoom competitors who had “stayed in the game and kept compounding”—were now worth over a combined sixteen-and-a-half billion.

The Hartz Values

Throughout the countless ventures Kevin has embarked on, he’s noticed two common values which thread through them all. The two same values that he and Julia emphasize to both their kids and to every founder they back:

One—the drive to learn. The curiosity that pulled Kevin through a history and applied earth sciences double major at Stanford, a Masters in history at Oxford, and now cutting edge hardware at Sauron.

Two—the drive for adventure. The thrill-seeking restlessness of an Orindan teen blowing up model boats, and the dauntless entrepreneur traveling around the world, working with different partners for Xoom.

Those two, for Kevin Hartz, are “the family values that translate over to any founder."

© 2025 Yesterday Media Co.

All Rights Reserved.

Privacy Policy

Terms of Service