The Money and Drugs That Tie Elon Musk to Some Tesla Directors
Board members have reaped hundreds of millions from stock awards and separate investments, even as some have done drugs with Musk; former Tesla director Larry Ellison offered him a chance to dry out
By KIRSTEN GRIND
Mon, Feb 5, 2024 8:55am 14min
BERLIN, GERMANY DECEMBER 01: SpaceX owner and Tesla CEO Elon Musk (Photo by Britta Pedersen-Pool/Getty Images)
Board members at Elon Musk’s electric-car maker, Tesla, were facing a dilemma.
One longtime director, the venture capitalist Steve Jurvetson, had left his firm after an internal investigation found he had slept with multiple women in the tech industry and used illegal drugs.
Some of the details had been splashed across the press in 2017, and Tesla directors informally discussed how they should handle it, according to people familiar with the situation. Some urged him to resign.
Luckily, Jurvetson, even though the company designated him an independent director, had a good friend with whom he had deep financial ties and also attended parties with, using ecstasy and LSD: Musk.
Musk pushed directors in private conversations to allow Jurvetson to take an unusual leave of absence from the board of the public company, and then step down on his own accord in 2020, the people said. Jurvetson remains a director at Musk’s privately held rocket company, SpaceX.
“The answer was do nothing and see what happens,” said another former independent Tesla director and good friend of Musk’s, Antonio Gracias, in a 2021 court deposition, when asked how the board handled the Jurvetson situation. Gracias and his venture-capital firm held investments recently valued at about $1.5 billion in Musk companies.
Multiple other directors of Musk companies have deep personal and financial ties to the billionaire entrepreneur, and have profited enormously from the relationship. The connections are an extreme blurring of friendship and fortune and raise questions among some shareholders about the independence of the board members charged with overseeing the chief executive. Such conflicts could run afoul of the loose rules governing what qualifies as independence at publicly traded companies.
On Tuesday, a Delaware judge struck down Musk’s multibillion-dollar pay package at Tesla, saying board members who signed off on it in 2018 were beholden to Musk.
Several current or former directors at Tesla and SpaceX attend parties with him, go on exotic vacations and hang out at Burning Man, the Nevada arts and music festival.
Musk and these directors, including venture capitalists Gracias and Ira Ehrenpreis, tech mogul Larry Ellison, former media executive James Murdoch, as well as Musk’s brother, Kimbal Musk, have invested tens of millions of dollars in each other’s companies—Ellison held billions of dollars in Tesla shares with about a 1.5% holding in 2022. Some also received career support and help from Elon Musk.
Most members of Tesla’s current eight-person board have amassed shares worth hundreds of millions of dollars from their seats over the years, significantly more than what board members at other companies make for their service.
Tesla pays its directors mostly in stock options, and the current board, not including Musk himself, collectively has made more than $650 million selling shares from those options. They hold additional options valued at nearly $1 billion. Some directors agreed to return a portion of that compensation to Tesla to resolve a shareholder lawsuit about their compensation while denying any wrongdoing. A judge has yet to approve the settlement.
Some current and former Tesla and SpaceX directors have knowledge of Musk’s illegal drug use but haven’t taken public action, according to people who have witnessed the drug use or were briefed on it.
The Wall Street Journal reported in January that Musk has used drugs including cocaine, ecstasy, LSD and magic mushrooms, and that leaders at Tesla and SpaceX were concerned about it, particularly his recreational use of ketamine, for which Musk has said he has a prescription. The illegal drugs violate strict anti drug policies at Musk’s companies and could put SpaceX’s federal contracts and Musk’s security clearance at risk.
At the upscale Austin Proper Hotel, Musk has attended social gatherings in recent years with Tesla board member Joe Gebbia, the Airbnb co-founder and a friend of his, where Musk took ketamine recreationally through a nasal spray bottle multiple times, according to people familiar with the drug use and the parties.
Other directors, Gracias, Jurvetson and Kimbal Musk, have consumed drugs with him, according to people who have witnessed the drug use and others with knowledge of it.
Musk and some people close to him, including Kimbal Musk, attend parties at Hotel El Ganzo, a boutique hotel in San José del Cabo, Mexico, known for its art and music scene as well as drug-fueled events, according to people familiar with the parties.
The volume of drug use by Musk and with board members has become concerning, some of these people said.
In the culture Musk has created around him, some friends, including directors, feel there is an expectation to consume drugs with him because they think refraining could upset the billionaire, who has made them a lot of money, some of the people said. More so, they don’t want to risk losing the social capital that comes from being close to Musk, which for some feels akin to having proximity to a king.
Musk and his lawyer, Alex Spiro, didn’t respond to requests for comment.
In response to the Journal article in January about Musk’s illegal drug use, Spiro said Musk is “regularly and randomly drug tested at SpaceX and has never failed a test.”
After that article, Musk tweeted that in three years of undergoing random drug testing after a pot-smoking incident in 2018, “Not even trace quantities were found of any drugs or alcohol. @WSJ is not fit to line a parrot cage for bird [poop emoji].” He later tweeted: “If drugs actually helped improve my net productivity over time, I would definitely take them!”
Tesla’s general counsel and a SpaceX spokesman didn’t respond to requests for comment.
Ellison offer
Some board members worry about the negative effects of Musk’s behaviour on the six companies he oversees and the roughly $800 billion in assets held by investors, according to people close to Musk.
Despite the concerns, the Tesla board hasn’t investigated his drug use or recorded their worries into official board minutes, which could become public.
Around the winter of 2022, Musk’s good friend and former Tesla board member, Ellison, urged him to come to his Hawaiian island to relax from work and dry out from the drugs, according to people familiar with the offer.
The outreach came as friends and others close to Musk worried that his drug use was getting worse, and some asked him to go to rehab, some of the people said.
Around the same time as the Ellison offer, Musk attended a party in the Hollywood Hills where he consumed a liquid form of ecstasy from a water bottle, according to a person who was there. Musk’s security guards asked people to leave the floor of the house for privacy before Musk took the drug.
Across Silicon Valley, executives sometimes invest in each others’ companies and ventures, and might have one or two personal friendships on a company board, especially before it goes public.
Musk, because of the extent of his personal and professional board ties and the enormous amount of money involved, is the most prominent example of a chief executive who is intertwined with directors. The Journal traced connections by reviewing hundreds of pages of court documents and depositions, Securities and Exchange Commission filings and other public records.
The amount Tesla pays its directors is far more than the average compensation for boards at most U.S. companies. The average total compensation for board members in the largest 200 U.S. companies was $329,351 in 2023, according to a new report from the National Association of Corporate Directors and compensation consultant Pearl Meyer. By comparison, current Alphabet board members hold stock valued at about $8 million, and received an average annual compensation for board service of about $475,000 since 2015.
Beyond board pay, some Tesla and SpaceX directors have tens of millions of dollars in additional investments in Musk’s companies, including his brain implant startup, Neuralink, and his tunneling venture, The Boring Co.
Musk, in turn, invests in some directors’ companies. Board members also have invested in Kimbal Musk’s Kitchen Restaurant Group and in SolarCity, a company run by Musk’s cousins that was acquired by Tesla.
Governance experts, such as longtime board members and advisers to boards, say the personal and financial ties could muddy directors’ views, and that it is highly unusual at U.S. public companies.
According to the rules of Nasdaq, where Tesla trades, an independent director can’t be an employee, a family member or someone whose relationship “would interfere with the exercise of independent judgment.” Nasdaq requires a majority independent board.
While rules governing independent directors across the country are murky, financial entanglement is one area where courts have sometimes found public companies at fault for claiming directors’ independence while they hold investments tied to one another.
Amalgamated Bank, which managed around $180 million of investments in Tesla as of September, signed a shareholder letter last year asking Tesla board members to step up their “meagre oversight” of Musk.
The investors expressed concern that the close ties between Musk and several Tesla directors make the board ill-equipped to act in the best interest of shareholders.
CEO with leeway
Some directors view Musk as a once-in-a-generation genius, with a brilliant mind and unusual methods. In depositions and courtroom testimony, directors have said they think Musk’s leadership is crucial to both Tesla and SpaceX, and believe in his long-held mission to colonize Mars. He is seen as the soul of his companies and intertwined with their success. Tesla’s stock is up more than 300% in the past four years, but has dropped about 25% since the beginning of January.
When striking down Musk’s pay package on Tuesday, the Delaware Court of Chancery judge called the process for approving it “deeply flawed” and cited Musk’s “extensive ties” to some of the directors who negotiated it. A Tesla shareholder had sued, alleging Musk played too big a role in deciding his own pay.
Musk “enjoyed thick ties with the directors tasked with negotiating on behalf of Tesla, and dominated the process that led to board approval of his compensation plan,” wrote Chancellor Kathaleen McCormick in the opinion. She described board Chair Robyn Denholm’s approach to her oversight obligations as “lackadaisical.”
Tesla board members can appeal the decision to the Delaware Supreme Court. After the ruling, Musk posted on X saying, “Never incorporate your company in the state of Delaware” and said Tesla would hold a shareholder vote about incorporating in Texas.
Board members had signed off on the pay deal in 2018, with Tesla valuing it at a maximum of $55.8 billion. It was the biggest pay package ever to the chief executive of a U.S. public company, according to governance-data firm Equilar.
While negotiating the pay package, Musk emailed the company’s top lawyer explaining how he would use the additional compensation. “The added comp is just so that I can put as much as possible towards minimising existential risk by putting the money towards Mars,” Musk wrote. Ehrenpreis, a yearslong friend, was head of the board’s compensation committee.
Company directors frequently allowed Musk an unusual amount of leeway on issues big and small.
After he bought Twitter in 2022, for example, Musk tapped Tesla employees to review the social-media platform’s engineering talent. Also around that time, SpaceX signed off on an unusual $1 billion loan to its chief executive, the Journal has reported.
A 2018 settlement with the SEC, following Musk’s tweet about plans to take Tesla private, required Tesla to establish more controls and form a new committee of independent board members to oversee Musk’s communications. But according to court documents, Denholm said Musk “does self-regulate” compliance, and some directors said they don’t review his tweets.
Tesla disclosed in 2022 that it had received a subpoena from the SEC seeking information about how the company was complying with the settlement.
Musk’s freewheeling commentary on Twitter, now X, and in interviews has injected volatility into Tesla’s share price and affected his other companies. In 2020, Tesla’s stock closed down more than 7% for the day after Musk tweeted, “Tesla stock price is too high imo.” Last year, major companies stopped advertising on X after he described an antisemitic post on X as “the actual truth.”
Investors have for decades pressed for independent directors, especially at public companies, because it allows them to push back against management and closely monitor what is happening inside the business.
The sweeping set of rules known as Sarbanes-Oxley in 2002 mandated that public companies have independent directors, including on the audit committee. The rules came after the collapse of energy trading giant Enron, which later was found to have hidden its financials amid improper board oversight.
Stock exchanges generally spell out how they define independence on boards and other expectations. At private companies, there are no requirements for the number of independent directors, or what constitutes one. At Nasdaq, if a company doesn’t comply with its majority independent board rule, it gives the company one year or until its next shareholder meeting to make a change; if not, it may be delisted.
Questions about a public director’s independence have gone to the courts, with judges sometimes finding problems with deep financial ties.
The Delaware Supreme Court in 2016 ruled that the majority of videogame developer Zynga’s board weren’t independent. Among the reasons was that a venture-capital firm two directors worked for had invested in a startup the CEO’s wife co-founded and that another director and her husband co-owned a private plane with the CEO.
Following the court’s decision, Zynga expanded its board and formed a special litigation committee to investigate insider trading allegations. Zynga settled the suit in 2019 for $11 million.
“To me, it’s really: Are you capable of making a disinterested, objective decision uninfluenced by the relationship?” said Lawrence Hamermesh, former director of the Widener Institute of Delaware Corporate and Business Law, who has also served as senior special counsel in the SEC’s corporate finance division.
Surrounded by friends
When Tesla was looking to replace a departing director, it turned to a familiar face in JB Straubel. The board believed the company’s former chief technology officer, whom Tesla considers a co-founder, was someone Musk would listen to, could fill Ellison’s shoes and had technical expertise, according to people with knowledge of the board’s thinking.
Last year, ahead of a vote to approve Straubel, some shareholders pushed back over his close ties to the company, saying if he were added to the board then at least five of the eight members would lack independence. Straubel was elected anyway. A Nasdaq spokesman said it doesn’t comment on specific companies and referred a Journal question on how Straubel can be classified as an independent director to Tesla.
Musk has long surrounded himself with close friends as he built his business empire. He has turned to them for advice on new business ventures and on daily operational help.
In addition to Musk on the Tesla board, his brother, Kimbal Musk, is a member. He previously served on the SpaceX board and has counselled Musk on numerous ventures, including whether to start OpenAI and Neuralink. He and Musk are also close personally, often attending the same events and parties.
Ehrenpreis, who chairs two of four committees on the Tesla board, is designated independent by the company and has been close to Musk for years.
The venture capitalist held the right to buy the first Tesla Model 3—which some covet for bragging rights. Around Musk’s 46th birthday in 2017, he gave it to Musk, tweeting, “Much love and respect for everything you do.”
Ehrenpreis has personally or through his venture-capital firm, DBL Partners, invested in many of Musk’s ventures, totalling about $70 million.
On the Tesla board, he has made more than $220 million on stock sales earned through board service and has additional options worth more than $200 million at recent prices.
James Murdoch, former chief executive of 21st Century Fox, also is classified independent by Tesla. His friendship with Musk dates back to around 2006, and he has vacationed with Musk and their families, including on trips to Israel and Mexico.
In court testimony in 2022, Musk said he didn’t know Murdoch well, though Murdoch in an earlier deposition affirmed his friendship with Musk.
Murdoch, who is the younger son of Rupert Murdoch, chairman emeritus of News Corp, which owns The Wall Street Journal, has said in court testimony he considers himself independent and has described a director as “having an ability to exercise independence of thought in governance and oversight as a member of a public company.”
Murdoch poured $20 million into SpaceX, and a company controlled by him invested about $50 million in the space company, court records show.
Denholm, who is designated independent, is based in Australia and doesn’t socialize with Musk. She has said in court testimony she doesn’t have personal investments in Musk’s other companies.
Her decade-long position on the Tesla board has been lucrative, earning her more than $625 million in the company’s equity. Denholm has exercised about half her options, profiting more than $280 million from the sales.
Denholm runs Tesla board meetings as informal, family-style occasions. Directors sometimes ask softball questions of Musk, such as future Tesla product colours, according to people familiar with the board.
Musk, meanwhile, would sometimes arrive two hours late, or hours early, and then blame his staff for not getting him there at the appropriate time, according to one of the people.
Musk said he handpicked Denholm, who replaced him as board chair in 2018 under an agreement with the SEC, according to an interview on “60 Minutes” that year.
The idea Denholm would watch over him was “not realistic” given his status as the company’s largest shareholder, he said in the interview, adding: “I can just call for a shareholder vote and get anything done that I want.” Musk later tweeted that the show had edited the interview in a misleading way. A “60 Minutes” spokeswoman said the show stands by its reporting.
Gebbia, the Airbnb co-founder and friend of Musk’s, joined the Tesla board in 2022, lives in Texas and is designated an independent director.
Former Walgreens Boots Alliance executive Kathleen Wilson-Thompson, who joined the board in 2018, is designated independent and doesn’t have public ties to Musk.
Deal with ex-girlfriend
Three current and former Tesla and SpaceX board members have been among Musk’s closest personal and financial partners.
Ellison, the co-founder and current chief technology officer of Oracle, was designated independent during his board tenure at Tesla between 2018 and 2022. He has said “I’m very close friends” with Musk and has hosted him multiple times at his Hawaiian island, Lanai.
When Musk revealed his plans to buy Twitter, Ellison committed $1 billion in 2022, while still on the Tesla board, to help fund it, surpassing the investments of many of the venture-capital firms involved in the deal.
Gracias, whom Tesla classified as the company’s lead independent director from 2010 until 2019, has been close friends with Musk for more than two decades. Musk turned to Gracias for support after his baby son died in the early 2000s, according to a 2021 court deposition.
He is also one of the friends who attends private parties around the world and sometimes consumes illegal drugs with Musk.
In court testimony in 2022, he called Musk “extraordinary,” “an amazing engineer” and “a product genius.”
For his work on the Tesla board, he has made more than $100 million by selling shares he earned.
Former Tesla and current SpaceX board member Steve Jurvetson, shown in 2016, is among the directors who have used drugs with Musk, according to people who have witnessed it and others with knowledge of it. PHOTO: NIKKI RITCHER FOR THE WALL STREET JOURNAL
When Musk needed cash, Gracias lent him $1 million, Gracias said in a court deposition, though it is unclear when he gave the money or what it was for. Musk has also personally invested about $10 million in Gracias’s Valor Equity Partners.
When asked in a court deposition whether his close friendship and business relationships with Musk affected his ability to act as an independent director at Tesla, particularly related to Musk’s 2018 pay package, Gracias said it didn’t. “Otherwise, I wouldn’t have done it,” he said.
Gracias stepped down from the Tesla board after more than a decade in 2021 in response to the pressure to improve its corporate governance. He remains a SpaceX director.
Jurvetson is one of Musk’s closest friends, and the two have mixed friendship and business for years. Jurveston was an early investor in SpaceX, and the two have used LSD and ecstasy together.
Jurvetson, who is an amateur rocket enthusiast, often hosts Elon and Kimbal Musk for parties at his house at Half Moon Bay, a small beachside city south of San Francisco.
One episode, soon after the 2017 scandal that led to Musk and Jurvetson working to keep his Tesla board seat, shows the extreme intertwining of personal and business relationships around Musk.
Tesla’s general counsel at the time, Todd Maron—who had been a divorce lawyer for Musk—helped negotiate an understanding with one of Jurvetson’s ex-girlfriends, Keri Kukral, according to emails between the company and Kukral reviewed by the Journal.
As part of the 2018 arrangement, Kukral was given permission by Maron to review and approve public messaging, such as press releases, related to Jurvetson and his Tesla board seat, the emails show. After Maron left Tesla, his successor general counsel, Jonathan Chang, continued to communicate with her, the emails show.
In return, Kukral wrote a professional recommendation of Jurvetson to Tesla as he campaigned to keep his board seat.
It is highly unusual for a company’s general counsel to get involved in such personal matters of board members, or to give an outside person the power to review company messaging, corporate governance experts said.
Musk also tried to persuade board members to let Jurvetson vote while he was on a leave of absence, people familiar with the conversations said. Kimbal Musk, Murdoch and Denholm pushed back, the people said.
Jurvetson made more than $9 million selling Tesla shares received as a director before leaving the board in 2020, according to the documents reviewed by the Journal.
At least two former board members have bristled at the company’s lack of corporate governance and deference to Musk.
Former Tesla board member Linda Johnson Rice wasn’t close with Musk or other directors outside of work, although she sometimes saw fellow director Gracias at work events in Chicago, where they are both based.
She didn’t stand for re-election to the board in 2019 after serving less than two years over frustration with Musk’s volatile behavior, including his drug use, the Journal reported. She informally asked whether the board should investigate and was brushed off.
“She served her term and that was it,” Musk tweeted about Rice, following the Journal’s January article about his drug use. “No negativity at all with Linda!”
Similarly, Hiromichi Mizuno, a former chief investment officer of Japan’s Government Pension Investment Fund, left the Tesla board in 2023 after three years in part because of the lack of ability he felt he had to work on improving the company’s governance-related practices. At issue was the board’s deference to Musk, who had different priorities for Tesla, according to people familiar with the board.
Mizuno found the board to operate more like a family company with fiefdoms, rather than a public company with stringent rules and regulations, even if it did usually perform well. He has made a practice of avoiding close relationships with others in the workplace to remain objective. While Mizuno was sometimes invited for a drink with Musk, he never attended his private parties or events, according to the people.
Musk has been recently pushing for even greater control over Tesla. He currently owns around 13% of the company.
In mid-January, before the Delaware court ruling on his pay package, he wrote in a post on X that he was uncomfortable transforming the electric vehicle giant into a leader in artificial intelligence and robotics without voting control over roughly 25% of the company.
“Unless that is the case, I would prefer to build products outside of Tesla,” Musk wrote.
The tweet was effectively an ultimatum for Tesla board members to revisit his compensation. The board so far hasn’t acted.
—Berber Jin, Lisa Schwartz and Jim Oberman contributed to this article.
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Five Minutes With Five Executives
From early financial mistakes to hard-earned habits, five high-performing leaders share how they spend, invest and think about wealth.
By Nina Hendy
Tue, Sep 22, 2026 9min
Five minutes doesn’t sound like much. But it’s enough time to tell whether someone really understands money or just talks about it. Because once the gloss is stripped away, what’s left is instinct. The early mistakes. The bad calls. The quiet pivots that no one brags about but shape everything that follows. Making money is one thing. Living with it, and not mishandling it, is another. Here, five executives talk about what they got wrong, what they’ve learned, and how they now actually spend, invest and think about wealth.
Andrew Raso: Founder, Online Marketing Gurus
Andrew Raso, founder of Online Marketing Gurus.
Self-made millionaire Andrew Raso grew up in an ethnic household with a father in construction. Investing was not a priority, he recalls.
The co-founder and CEO of Online Marketing Gurus, a digital marketing platform that generated more than $30 million in revenue in the 204/25 financial year, admits he’s had to learn about handling money as his wealth has grown.
“If I had my time again, I would change my spending habits and would probably be a lot more wealthy as a result,” the Sydneysider tells Kanebridge Quarterly.
Raso, in his mid-30s, says that his biggest lessons have come from his losses.
Buying the wrong property and copping the losses upon sale. Feeling FOMO when buying crypto and making a purchase that lost money.
“I’ve learned a lot from the errors that I’ve made,” he says.
Raso admits that he gets more of a thrill out of working than watching money hit his bank account.
“I’ve had the cars, I’ve had the property, I’ve had the watches. Once you’ve had them, they’re not that exciting, but the process of earning money is pretty cool.”
What he won’t forget is being $45 million in property debt a few years ago.
“I’d never want to be in that position again,” he says.
“My investing strategy is a lot safer these days. I’m very cautious. I’d prefer to invest in things that don’t take as long to be realised so my family can be financially secure.
“Once you have a house paid off and a few investments, it then becomes about enjoying your money, rather than hoarding it. Giving back gives me a much bigger kick than spending these days.”
Daniel Wessels: CEO, Jacaranda Finance
Daniel Wessels, CEO, Jacaranda Finance. Photo: Glenn Hunt.
Fintech founder Daniel Wessels knows only too well that money remains a taboo topic in Australia with many people.
He points to consumer surveys that reveal people are more likely to talk about their sex life with friends than their finances.
It’s a major concern for the man who founded Jacaranda Finance in 2013, which has helped countless people lift their credit scores and get their finances back on track.
“If people aren’t learning money habits at school and they aren’t discussing it with their friends, learning new strategies and better habits is difficult,” says Wessels, who is based in Brisbane.
He wants to see more people take the time to proactively understand where and why they are spending money.
“Everyone needs to have a financial strategy and a plan to measure if it’s working,” he says.
The father of two young children admits his week can be pretty fast-paced. Pomodoro clocks, sleep optimisation techniques and saying ‘no’ keep him on task during the week.
“I used to think I was fairly decent at managing time, but the whole game changed when we had kids,” he says.
“Now, I’ve got to get out of the house at a certain time and leave the office at a certain time for daycare pickup. I’ve got to be really specific about my tasks to maximise my week.”
Before he had a family, he loved heading out to one of the trendy new restaurants popping up in Brisbane.
But that happens less these days. He’s saving to build his forever home but admits that price rises have resulted in rising costs.
“It’s such a big project with so many variables that change quickly,” he says.
These days, Wessels likes to optimise his professional and personal life. “With only a finite amount of money, time and energy, you’ve got to be really good at deciding what you want to be good at,” he says.
He calls this ruthless prioritisation. He has a very specific focus on activities that prioritise health and wealth, adding experiences into the mix more recently. This has meant the addition of micro-holidays to his annual calendar.
Wessels works with a couple of financial advisers. That said, he also does his own due diligence before agreeing to investments.
“One likes private equity investments that pay cash every month and another prefers to focus on the NASDAQ Stock Exchange for buying shares because he’s bullish about that.” he says. “They’re each experts and really good at what they do.”
Jim Penman: CEO, Jim’s Group
Jim Penman, CEO, Jim’s Group.
He may have invested a lifetime building a franchise juggernaut that is reportedly a $1 billion a year empire, but Jim Penman insists he’s a frugal guy who prefers to spend time planting a tree in his garden than contemplating his wealth.
What started out as Jim’s Mowing back in 1989 became Jim’s Group. Today, there are 5,700 franchisees across Australia and New Zealand in the business that has become ubiquitous for being the local handyman company that households could rely on.
He may have built a successful business empire, but the Melburnian insists he’s stingy when it comes to money.
“I wear my clothes even today until they wear out. I’ve always had a very lean and mean attitude. I live a simple life. My personal needs are very modest and my finances are simple,” he says. Jim reveals he’s usually in his garden these days and rarely eats out or takes holidays.
He is also running for state politics in the November Victorian election.
“I’m not particularly money focused. I could tweak the franchise contract to put more fees in and double my profitability, but that’s not my goal or my aim. To be honest, I often make decisions that go against my financial self-interest,” he says.
Jim purchased his first brand new car three years ago, opting for an electric Volvo.
“Being rich is not my aim and it never has been. People think I’m a lot richer than I am. They think I’m a billionaire, which is kind of ridiculous,” he says.
In fact, he insists he carries debt, which is common for anyone in business. “If I wanted, I could pay it off in 18 months.”
While his competitors were spending on fancy office space, Penman was running his franchise from his basement, keeping business costs low. “When I started out, I didn’t have any concept of how big this business could be. But there has never been a plan to grow franchisee numbers.
“Our attrition rate is far more important, and how to reduce complaint rates and drive more enquiries through new software.”
He believes people these days worry too much about impressing others, which leads to spending on superficial things.
“I would rather than offer people advice on how to be happy, rather than how to become rich. It’s important to have a good income so you can support yourself. But life is more about purpose.”
Jim doesn’t bother with stocks or bonds. He only invests in his own business. “My rate of return on my business is substantial. I could buy back a regional franchise when they come on the market and get a 20-25 per cent annual rate of return, plus capital gains. There’s nothing like that available in the investment space.”
Nicola Beswick: Founder, White Rabbit Advisory
Nicola Beswick, White Rabbit Advisory founder.
A clothing allowance provided by her parents and then a part-time job during high school was the first taste of financial freedom for Nicola Beswick.
She quickly became a spender rather than saver, but she’s changed her tune over the years.
The founder of financial advice firm White Rabbit Advisory left behind a successful career in intellectual property law a year ago to become a financial adviser because she realised the potential that financial education could have on someone’s life.
Her journey began after coming across the book Rich Dad Poor Dad some years ago, which opened her eyes to the power that money could have on her life. This marked a time when she became serious about her finances.
“Financial education and investing over time can have a huge impact on a person, and that book got me thinking about money and financial education in the first place,” she says.
Nicola says years ago, her father was diagnosed with multiple sclerosis. When dealing with the devastating news and an uncertain future, her father discovered he was eligible to receive an income protection payout.
“This was the stone that rippled his pond and mine. A new complex world of finance opened up and I discovered my calling – helping people plan for a financially secure future.”
She hasn’t looked back. “Commercial law was very transactional. I don’t regret quitting at all. I’m much happier now helping people get their finances in order. Financial planning helps people change their lives. That was a really big driver for me.”
The Melburnian admits she’s learned plenty of lessons along the way as she embarks on the process of building wealth. She uses superannuation as an investment vehicle, favouring its tax advantages.
“I also built a nest egg outside of super, because you never know when the rules will change,” she says.
She prefers to set a financial goal and save up for something specific over time than rush out and make a purchase.
“It’s a really powerful thing to wait before making a purchase,” she says.
Her current financial goals involve renovating her heritage-listed home. “We will keep the façade and gut it to rebuild. That’s a major expense for us on the horizon.”
While holidays are rare, she will spend on overseas trips on occasion. “I’m terrible at taking time off. I’m always working.”
Sam Riley: CEO, Drova
Sam Riley, Drova CEO.
Sam Riley was in his 20s when he set out to amass enough money to be able to retire by the age of 40 if he wanted to.
“The goal was always to be doing something by 40 that kept me engaged enough that I didn’t actually want to retire because I was happy,” he says.
An entrepreneur at heart, Sam started a juice and espresso bar when he was 21, which didn’t work out. His next venture was a technology business, Ansarada, an ASX-listed company he ultimately sold nearly two years ago for $250 million.
The sale set him up for life, but he’s not one to rest on his laurels, launching into the complex world of artificial ntelligence with his next technology play, a company called Drova.
The technology startup simplifies risk, compliance and resilience for small businesses. Sam believes it’s got potential to become a tech juggernaut in time.
Having early financial success has meant he has the luxury of slow mornings and working in short bursts throughout the day, problem solving, experimenting with what works and figuring out how to harness AI.
“I favour a more sustainable approach to working these days. More frequent breaks. Making sure not to deteriorate my capacity,” he says.
It was a hard slog. He admits he touched the fringes of serious burnout when he was younger, which he works hard to avoid these days.
“Every business venture has exposed a gap in my skills that I’ve worked to close. Whether that’s marketing or managing people, closing those gaps along the way is how you get more effective at generating wealth,” he says.
The secret to his success has been finding ways to bolster value in the corporate world, finding ways to bring more to the table. Sam admits he spends too much money on travel, food and niche vinyl audio equipment, like turntables. He prefers to invest in experiences rather than things.
But it can get expensive. Like a recent trip to Antarctica to stay in a lodge for a week. “The thing is I didn’t like having these experiences on my own, so I have to bring family or other people and then pay for them.”
Sam describes his investment portfolio as balanced. While he continues to invest in entrepreneurial ventures, he admits he has a safe foundational platform to his investment approach.
“Over the years, I’ve added a lot more dividend stocks and protective assets like gold and silver, and some index funds.
“When I was younger, I didn’t appreciate the value of being safe and boring in the investment world.”
He says a lot of his investments used to be leading edge and visionary. “Some of them work, and some of them don’t. I didn’t really have much balance in my portfolio. I still invest in entrepreneurial things, but am much more conscious of taking a more even-handed approach,” he says.
This article appeared in the Winter 26 issue of Kanebridge Quarterly, which you can buy here.
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