The South African investor headhunted by Elon Musk 

Roelof Botha, grandson of former foreign minister Pik Botha, now leads the world’s largest venture capital firm, Sequoia Capital, and is responsible for $55 billion in assets. 

Many consider his membership in the PayPal Mafia as Botha’s proudest achievement, being hired directly by Elon Musk to oversee crucial parts of the business. 

Botha had rejected two prior job offers after finishing at the top of his MBA class at Stanford before Musk asked him to work at X.com.

Musk made sure the extremely talented and hard-working student would sit at the desk next to his at X.com as it developed into online payment giant PayPal. 

Botha still has the original recruitment letter signed by Musk himself and thinks fondly of his time as director of corporate development. 

He eventually rose through the ranks to become PayPal’s CFO before being headhunted by Sequoia Capital’s Michael Moritz to join the venture capital firm. 

Moritz grew Sequoia into the world’s largest venture firm, investing heavily in tech start-ups during the early days of the Internet. 

The company started in Silicon Valley’s initial growth phase when it emerged from the Cold War era military-industrial complex. 

Founded by Don Valentine in 1972, the firm was one of the earliest investors in Apple. 

Some of Sequoia’s best investments include Reddit, Apple, YouTube, Airbnb, and PayPal. The company currently holds stakes in SpaceX, Square, and Stripe. 

Today, the company, overseen by Botha, has become an umbrella organisation for venture capital firms worldwide, including those in India and China. 

Botha has led a substantial overhaul of the business to improve its efficiency and ensure it captures increasing value from its early investments. 

Controversially, this has led Sequoia to stay invested in some of its companies longer than the traditional 10 to 15 years of other venture capital firms. The firm also, in rare cases, looks to stay invested in companies after they list publicly. 

Below is the story of how the son of an economist and grandson of Pik Botha was hired by Elon Musk and oversaw the world’s largest venture capital firm. 

From UCT to Silicon Valley

Roelof Botha was born in Pretoria to economist Dr Roelof Botha and soon moved to Cape Town to be raised in Hout Bay. 

Botha is the grandson of the late minister of foreign affairs, Roelof Frederik “Pik” Botha. The youngest Roelof shares his grandfather’s middle name. 

In Cape Town, Botha attended Hoërskool Jan van Riebeeck and flourished academically. After never speaking English at home, he was set on attending an English university to enable him to move overseas. 

He swiftly moved into finance after graduating from the University of Cape Town with a BSc in Actuarial Science, Economics, and Statistics. 

The young Botha landed a job as a business analyst at consulting firm McKinsey & Co. in Johannesburg and worked there for a few years. 

At the time, Botha said he was reading about what was going on in Silicon Valley and was set on challenging himself against the world’s best and riding the wave of the internet. 

He said he never even knew what venture capital was or that he would work at a tech start-up. “I just had an intuition that I needed to be here,” he says. 

After two years at McKinsey, Botha enrolled at Stanford University for an MBA and finished top of his class. Job offers flooded in after that.

One immediately stood out. After rejecting two offers, Botha was introduced to Elon Musk by a mutual friend, after which the X.com founder convinced him to join the fledgling startup. 

Musk thought traditional banks were outdated and set out to disrupt them, launching X.com as an online financial services company. This would morph into PayPal. 

When he joined X.com, Botha became responsible for its financial and risk management, creating a clever model to deal with the challenges of corporate fraud. 

In 2000, X.com merged with Confinity to form PayPal, and the wheels began to fall off. Musk preferred the name X.com, while most employees preferred PayPal. 

Musk’s management style became increasingly intense, resulting in a small group of employees persuading the board to oust him as CEO and bring back Peter Thiel. 

Botha rose to become PayPal’s CFO, and once he left, he said that Musk had not provided the board with a full picture of the company’s problems. 

“I think it would have killed the company if Elon had stayed on as CEO for six more months,” Botha told Ebbe Domisse.  “The mistakes Elon was making at the time were amplifying the risk of the business.”

At the age of 29, during the Dot-com Bubble, Botha was overseeing the financial operations of a billion-dollar company and led it through its IPO in February 2000. 

PayPal was soon sold to eBay for $1.5 billion, making Botha a millionaire overnight. 

In 2007, Fortune published a photo of thirteen former PayPal employees in gangster attire, creating the moniker ‘PayPal Mafia’. Botha was among them, but Musk was absent. 

Botha received an offer to stay on at PayPal, but Sequoia’s Michael Mortiz offered him a chance to enter the venture capital world. 

“When Mike Moritz asked me to come interview at Sequoia, that was just another door opening. Where might this one lead?” he recalls on the firm’s website. 

Botha has been tremendously successful as an early-stage venture capitalist, growing Sequoia’s assets under management and his own wealth. 

He led the firm’s early investments in YouTube, Instagram, and Square – netting the company hundreds of millions of dollars. 

Botha attributes this success to his focus on the unconventional and his lack of shame in being made fun of by other investors, forged by his South African background. 

He admitted in Domisses’ Fortunes that it is easy to feel intimidated when you come from a small country such as South Africa.

“In America, there are many people who attended one of the top high schools in the world and who’ve studied at one of the top universities, and there is always this question mark at the back of your mind – Can I compete with these people?”

“But immigrants have a lot to prove, and of course, there’s the fact that the immigrants had to overcome many things just to be here in the first place.”

“How many of the South Africans who apply are accepted at Stanford? It’s a small percentage. So the people who come here are already a tiny fraction of the population of their home countries.”

“Because you don’t have this established network, you have to work hard. It’s not just a given that you’re going to be successful; it’s not through your family connections or friends that you will get a job or something. You have to roll up your sleeves and get to work.”

In making early, contrarian bets on YouTube and Instagram, Botha said there is some pleasure and defiance in saying, “We’ll show you!”. 

He recalled an article in 2001 titled Earth to Palo Alto, which called PayPal’s executives deranged. A few years later, they became millionaires when PayPal was bought by eBay. 

“There’s something intriguing to me about somebody who’s an original thinker, who is quirky, and maybe an outsider. I love spending time with people like that.” 

“Often, I judge based on how I feel when I meet someone the second time. With most people, you can have a pretty interesting conversation once. The real test is the second conversation – do I lose interest?” 

Botha took over responsibility for the firm’s US operations in 2017 and later replaced Doug Leone as Senior Steward of Sequoia’s global operations in 2022.  

He has overseen one of the most turbulent periods in the firm’s history, from FTX’s collapse to the split of its China business. 

Botha personally apologised to investors on whose behalf Sequoia invested millions into FTX when the crypto exchange collapsed in November 2022. 

A few months later, Botha had another crisis when Silicon Valley Bank collapsed, threatening $1 billion of Sequoia’s deposits.

The company’s deposits were saved by the Federal Deposit Insurance Corporation, which backstopped funds held by the bank. 

In June 2023, Botha oversaw the split of Sequoia’s business into three entities to make the firm more efficient and avoid any geopolitical tension between the US and China. 

The firm’s businesses split into the US and Europe-focused Sequoia, the China-focused HongShan and the India-centric Peak XV Partners. 

In October 2023, the United States House Select Committee on Strategic Competition between the United States and the Chinese Communist Party announced a probe into Sequoia Capital’s investments in China.

Since then, Botha has enjoyed a more stable 12 months leading the world’s largest venture capital firm, which has around $55 billion in assets. 

“Whenever I interview people, I ask about those key moments in somebody’s life where they’ve made career decisions.”

“And I think about companies in the same way – there are these crucible moments that have an enormous bearing on ultimate outcomes.”

“For me, 2023 was a crucible moment for the new Sequoia.”