The vast majority of us would not take the risk of playing that game even once. After all, it seems morally atrocious to take a 49% chance of all human civilization disappearing, for a 51% chance of doubling the value of our civilizationessentially a coin flip.

Yet when asked exactly that in a March 2022 podcast with Tyler Cowen, Sam Bankman-Fried (SBF) was quite willing to play that gameand keep playing it, over and over again. Cowen asked SBF about the high likelihood of destroying everything by going double of nothing on a series of coin flips. SBF responded that he was willing to make this trade-off for the possibility of coin-flipping his way into an enormously valuable existence.

Listening to that podcast made me realize that this high-risk, high-reward decision-making philosophy is what made his wealth possiblebut also fragile. Indeed, he was worth $26 billion at the peak of his wealth. He was the golden boy of crypto: lobbying and donating to prominent government figures, giving high-profile interviews, and rescuing failing crypto projects. In fact, he was nicknamed cryptos J.P Morgan.

His decision-making philosophy worked out for himuntil it didnt.

FTX filed for bankruptcy on Nov. 11, along with 130 other entities associated with it. That filing stemmed from the revelation of some very shady bets and trades, which led to a run on the exchange and federal investigations for fraud.

SBF resigned as CEO as part of the bankruptcy filing. His wealthall tied up in FTX and related entitiesshrank to near zero. His coin-flipping luck finally ran out.

As his financial empire was collapsing, SBF tweeted: I f**ked up a poor internal labeling of bank-related accounts meant that I was substantially off on my sense of users margin.

Certainly, we shouldnt simply take SBFs word for the situation at hand, given the circumstances. Yet at least the atrocious book-keeping part of the explanation and excessive optimism about user funds is supported by the only external investigation of the matter so far.

Binance, the worlds biggest cryptocurrency exchange, originally offered to buy out FTX as it was collapsing. However, after taking a look at FTXs books, Binance saw that the problem was too big to solve. Binance backed out, citing revelations of mishandled customer funds and describing the books as a nightmare and a black hole, according to a person familiar with the matter.

Messing around with customer funds is a big no-no. The Securities and Exchange Commission (SEC), Commodity Futures Trading Commission (CFTC), and Department of Justice (DOJ) are all investigating FTXs handling of customer funds. Specifically, theyre examining whether FTX followed securities laws related to the separation of customer assets and trading against customers.

Reuters has reported that SBF built what two senior employees at FTX described as a backdoor in FTXs book-keeping system, created using bespoke software. This backdoor enabled SBF to execute commands that would not alert others, whether at FTX or external auditors. The two sources told Reuters that SBF allegedly secretly transferred $10 billion of customer funds from FTX to SBFs own trading company, called Alameda Research.

In conversations with investors, SBF reportedly described his decision to loan $10 billion to Alameda as a poor judgment call. This coin flip landed on the wrong side. Double or nothing turned into nothing.

The underlying story here is of a fundamental failure of compliance and risk management. The inner circle of executives at FTX and related companies such as Alameda lived together at a luxury penthouse and had very strong personal and romantic bonds. Fortune spoke to several former and current employees at FTX who described the inner circle as a place full of conflicts of interest, nepotism, and lack of oversight. Naturally, this context of personal loyalty at the top makes it hard to have any oversight and risk management. It allows things like secret software backdoors, shady bookkeeping, and mishandling of client funds to flourish.

Such nonchalance toward risk management stems fundamentally from SBFs decision-making philosophy of high-risk, high-reward bets. SBF is unquestionably a visionary and financial genius. One of the most prominent venture capital firms in the world, Sequoia Capital, invested $210 million in his company and a partner at the firm said that SBF had a real chance of becoming the worlds first trillionaire. Yet it ignored the serious dangers of SBFs decision-making philosophy.

SBF is not the only multi-billionaire who ignores risk management and oversight. Consider Elon Musks approach to Twitter.

After taking over the company, he fired the vast majority of the existing executive team, as well as the Board, and replaced them with a select inner circle loyal to him. Then, he started experimenting with various Twitter features, most notably selling blue checkmark verification badges for $8 a month without any mechanism for confirming a users real identity.

Previously, Twitter only offered verificationfor freeto those who had some public status and could prove it. After Musks offering, thousands of new accounts popped up with a blue checkmark impersonating real people and companies, such as an account that looked like Eli Lilly claiming that insulin is now free. Musk seemed very surprised by this outcome, and paused the paid blue checkmark program in response.

The outcome of introducing paid blue badges was clearly predictable. Yet there was no meaningful risk management and oversight check on Musks actions, just like there was none over SBF.

The outcome of Musks risk-taking at Twitter might be bankruptcy, which would mostly be a loss for some big banks and investors. The outcome of SBFs risk-taking at FTX is definitely bankruptcy. That bankruptcy not only harms large investors: it also destroys the savings of many thousands of ordinary people who held their money in FTX.

SBFs misdeeds also harm the many worthwhile charitable causes to which he donated, such as pandemic preparedness. A committed philanthropist who already gave away many millions focusing on evidence-based charities, SBF raised hopes for inspiring billionaires to give away their wealth rapidly, just like MacKenzie Scott. However, many charity projects to which he promised funding are now in limbo, with their funding withdrawn. The employees at SBFs granting organization, the FTX Future Fund, resigned due to the revelations of misdeeds at FTX, saying they are concerned about the legitimacy and integrity of SBFs business operations that were funding the grants.

Such harmful consequences resulting from a lack of oversight and risk management highlight why its critical for founders to have someone who can help them make good decisions, manage risks, and address blind spots.

Risk managers need to be in a strong position, able to go to the Board of Directorswhich needs to have true control over the CEO, and not have the CEO able to fire the Board, as did Musk. When I serve clients in this role, I insist on being able to access an oversight body as part of my consulting contract. I almost never need to use this optionbut having it available helps me rein in the double-or-nothing impulses of brilliant founders such as SBF or Musk, since they know I have that option.

If youre deciding to make an investment with a seemingly brilliant entrepreneur, do your due diligence on risk management and oversight. If it seems like the entrepreneur has no one able to rein in their impulses, be wary. They will take excessive risks and youre gambling rather than investing your money wisely.

Gleb Tsipursky, P.h.D, is the CEO of the boutique future-of-work consultancy Disaster Avoidance Experts. He is the best-selling author of seven books, including Never Go With Your Gut: How Pioneering Leaders Make the Best Decisions and Avoid Business Disasters and Leading Hybrid and Remote Teams: A Manual on Benchmarking to Best Practices for Competitive Advantage. His expertise comes from over 20 years of consulting for Fortune 500 companies from Aflac to Xerox and over 15 years in academia as a behavioral scientist at UNC-Chapel Hill and Ohio State.

The opinions expressed in Fortune.com commentary pieces are solely the views of their authors and do not necessarily reflect the opinions and beliefs of Fortune.

More must-read commentary published by Fortune:

Former chief financial officer Allen Weisselberg, the prosecutions star witness in the trial of two Trump companies, took the stand Tuesday in state court in Manhattan in a charcoal suit and blue tie. Weisselberg, 75, said that after entering his plea in August and agreeing to testify against the companies which are accused of hiding taxable income inside luxurious perks   his title was reduced to senior adviser.

My location changed as well, he told the jury, under questioning by Executive Assistant District Attorney Susan Hoffinger, explaining that he lost his perch on the 26th story of Trump Tower and was moved down a floor. He then described a party that Trump Organization executives nevertheless threw for him.

Much to my regret, Weisselberg said, my son wanted to make sure I had a birthday party and arranged for it at Trump Tower. 

It was a small birthday cake, he added.

But even after pleading guilty to the entire 15-count indictment against him, including charges of conspiracy and tax fraud, Weisselberg is still drawing his full, $640,000 salary and hopes to collect his $500,000 bonus in January, he told the jury.

How Perks Worked

Prosecutors are trying to show that the alleged tax fraud scheme at the Trump companies wasnt secretly hatched by Weisselberg and Controller Jeffrey McConney, as the defense contends, but part of the firms entrenched business practices. Trump himself, who isnt charged, has called the trial a baseless vendetta.

During his first day on the witness stand, Weisselberg presented a stark contrast to McConney, the DAs first witness, who faltered and was so evasive that the judge on Monday declared him a hostile witness, giving prosecutors more latitude in questioning him. Weisselberg, by contrast, seemed at ease as he told the jury how he received perks and bonuses.

Weisselberg said he reaped a host of benefits totaling about $1.7 million, including an apartment with a garage, and his-and-hers Mercedes Benzes to go in it. He testified that he also received unreported cash and got various personal expenses for his homes and his sons apartment covered, including flat-screen TVs and new furniture. These items should have been taxed like income. 

Between 2005 and 2017, Trump Corp., one of the two companies on trial, paid almost $1.2 million in rent for an apartment for Weisselberg and his wife, according to the DA. Weisselberg explained to jurors Tuesday that the perk came about after his wife became ill and moved to Florida. Trump offered him an apartment on Manhattans Upper West Side to be nearer the office, he said.

Donald knew I was going home to an empty house and nobody was there, Weisselberg told the court. He said, Move into the city instead of spending three hours on the train. 

Trump later personally paid for about $359,000 in private school tuition for Weisselbergs grandchildren, prosecutors said. 

Why Not a Raise?

Hoffinger asked Weisselberg why he didnt just ask for a raise. Weisselberg said he was helping the company save money.

In order to get a raise, the Trump Corp. would have had to give me double the amount, because taxes wouldve been withheld, he said.

Under the terms of his plea agreement, Weisselberg must testify truthfully and is hoping for a sentence as brief as 100 days in jail, according to his lawyer Nicholas Gravante, rather than the maximum 15-year prison term he otherwise could face. He continues his testimony on Thursday, when the trial resumes.

Sign up for the Fortune Features email list so you dont miss our biggest features, exclusive interviews, and investigations.

Advocate: Toyin Ajayi, co-founder and CEO of Cityblock 

Courtesy of Cityblock

In November 2022, Toyin Ajayis Cityblock raised $400 million to expand its geographic footprintan important step for the community-based healthcare provider. Cityblock focuses on the most underserved communities, including people on Medicaid, and offers a personal care team for each patient encompassing primary care, mental health, social services, pregnancy care, and urgent care. Knowing that social inequities have a great impact on health, Cityblock offers not only medical support but also helps to coordinate safe housing, food security, and childcare support, working with local shelters, housing agencies, and food pantries. Importantly, Cityblock works with insurance companies to provide in-home, community-based, and virtual-care at no extra cost, including no copays. Currently, Cityblock is in six states and D.C. (NY, NC, CT, MA, OH, IN), but it will be expanding soon thanks to the recent fundraising. 

Problem solver: Stephanie Strong, founder and CEO of Boulder Care 

Courtesy of Boulder Care

More than 75,000 people died from opioid overdoses in 2021, according to the CDC. Stephanie Strongs Boulder Care aims to decrease that number, through medication-based treatment for opioid addiction. Boulder Care delivers thousands of naloxone dosesa life-saving drug that can reverse an overdoseand buprenorphine prescriptionsa medication approved in 2002 to treat opioid use disorderto patients who need it. The company also offers telehealth support, including peer coaching and assistance accessing basic needs like safe housing, employment, or even help getting a phone, through partnerships with social services like emergency departments, safe-use spaces, needle exchanges, housing services, and more. In the summer of 2022, Boulder Care, which boasts excellent retention rates, with more than 70% of patients staying with the program for 12 months or more, announced it raised $36 million series B funding. Thanks to partnerships with 20 enterprise customers, many patients have access to Boulder Cares program via health plans and employers and pay no more than a $4 copay for treatment.

Inventor: Yonatan Adiri, founder and CEO of Healthy.io

Courtesy of Healthy.io

What if doctors could give a diagnosis based on a photo from your smartphone? This is the idea behind Yonatan Adiris Healthy.io. The company partners with health insurers, healthcare providers, and hospital and pharmaceutical systems to ship testing kits to patients homes. Along with the testing supplies, it takes advantage of smartphone cameras to run virtual diagnostic tests, including urinalysis, digitized wound care, and routine pregnancy monitoring. In July of 2022, Healthy.io received FDA approval for its Minuteful Kidney test, which allows people to test their kidney function from home, increasing adherence to the important annual urine test that about 80% of at-risk people skip. The startup teamed up with a large insurer and sent 100,000 free testing to kits to Americans at high risk for chronic kidney disease. Too often, the disease is caught late, when the kidneys have already suffered extensive damage or are in failure. Healthy.io test is a simple, convenient, and cost-effective way to detect kidney disease early. Results from tests are shared with clinicians, so patients can get prescriptions and advice without leaving home.

Creator: Taylor Morrison, founder of Inner Workout 

Courtesy of Inner Workout

The big idea behind Taylor Morrisons Inner Workout is that self-care requires a support system. Too often, we prioritize others needs over our own and give up the time we had set aside for ourselves. Inner Workout creates accountability for members who join the subscription-based community of like-minded people who also want to focus on self-care. The community includes a group chat, online events like mindful moments and taking care together, self-care workshops, and coaching. Morrison says she wants the Inner Workout experience to go beyond taking care of the physical body and encourage people to listen to themselves, understand what they need, and respond with love. Specifically, Inner Workout focuses on five dimensions of well-being: physical, energetic, mental and emotional, wisdom, and bliss. With this in mind, Inner Workout released the Instead card pack in the summer of 2021 with prompts to give people quick and concrete ways to care for themselves instead of scrolling through social media. 

Educator: Lorenzo Lewis, founder and Chief Visionary Officer of The Confess Project 

Courtesy of The Confess Project

After trying to hold meetings for Black men and boys to discuss mental health, but seeing that no one showed up, Lewis decided to meet the community where it is: in barber shops, where they feel comfortable opening up. The Confess Project trains barbers to be mental health advocates, through a free, year-long online course. Interested barbers are trained on four pillars: active listening, validation, stigma reduction, and communication. They learn to look for subtle changes in personality and signals of depression and anxiety in regular customers and help them open up about whats going on or even refer clients to local therapists or 988, the new mental health crisis hotline. In early 2022, The Confess Project moved its headquarters to Atlanta with satellite locations in Little Rock, Ark., and Los Angeles, and Lewis took on the role of Chief Visionary Officer. The Confess Project also started an ambassador program, training barbers to train other barbers and extend the projects reach and impact. 

Changemaker: Katy Milkman, co-founder and health director of Behavior Change for Good 

Peter Murphy/Courtesy of Behavior Change for Good

Wharton professor Katy Milkman co-founded the Behavior Change for Good initiative (BCFG) at the University of Pennsylvania to dramatically accelerate the development of interventions that work to change common human behaviors. A large part of BCFGs strategy is a new type of scientific approach called the megastudy, in which multiple teams of researchers examine the same problem from different angles and compare results. Partnering with big organizations like Walmart and 24 Hour Fitness gives them access to sample sizes large enough to test several interventions and get a good sense of what works, what doesnt, and what might be successful with one community but not another. BCFG uses the research to guide policymakers. As health director of the organization, Milkman oversees research on exercise frequency, vaccination uptake, among others. In December of 2021, BCFG published its first megastudy findings, which was done in partnership with 24 Hour Fitness and simultaneously tested 54 strategies to incentivize exercise. About 45% of the interventions significantly increased gym visits during the four-week program and 8% positively affected gym visits after the program ended. 

Pioneers: Peter Wang, co-founder and CEO, and Jessica Nouhavandi, co-founder and lead pharmacist of Honeybee Health

Courtesy og Honeybee Health

Jessica Nouhavandi and Peter Wang used to run a small family pharmacy in California and often saw patients who couldnt afford their medications. Knowing that a big portion of prescription costs are the result of the middleman (insurers), Nouhavandi and Wang opened online pharmacy Honeybee Health to sell generic medication directly from FDA-approved wholesalers at much lower costs. Patients using Honeybee Health dont have to be insured to purchase their medications. The need for this model is apparent in Honeybees success. In December of 2021, the company was named Los Angeless fastest growing private company by the Los Angeles Business Journal. The startup became even more critical when the Supreme Court overturned Roe vs. Wade in June, as its one of only two online pharmacies that ships abortion pills nationwide. It works with independent abortion clinics, major abortion telehealth startups, and primary care practices that are just starting to prescribe abortion pills, increasing access for millions of women and transgender people who have uteruses. (Though Honeybee Health is currently unable to ship prescription medication to AL, IN, LA, or MT.) 

Influencer: Rachel Cargle, founder of The Loveland Foundation 

Courtesy of The Loveland Foundation

For her 30th birthday in 2018, Rachel Cargle created a fundraiser on gofundme.com titled Therapy For Black Women & Girls. The fundraiser was a wild success, raising more than $250,000. Following this, Cargle founded The Loveland Foundation to continue the effort and bring opportunity and healing to communities of color. The fund offers sets of four voucherseach covering the cost of a therapy sessionto women and girls of color. In its 2021 annual report, The Loveland Foundation reported growing its impact from eight covered sessions per person to 12. Theyve served more than 5,000 people and funded 51,900 hours of therapy. In addition, The Loveland Foundation offers continuing education courses for the nearly 1,200 therapists it works with, such as classes on recognizing and treating eating disorders in Black women and girls. Under the greater Loveland Group, Cargle initiates other social ventures, such as her program The Great Unlearn, an online educational platform highlighting academics of color on topics such as the history of race, feminism, and more.

Leader: Eric Daza, creator of Stats-of-1

Courtesy of Stats of 1

Most of the time experiments call for a large sample size, but biostatician and health data scientist Eric Daza argues the power of a sample size of one. His blog Stats-of-1 attempts to build a community of statistics-savvy pioneers, mainly researchers and citizen scientists who use digital health tools like wearables and sensors, and personal data to understand what influences their health day-to-day. For example, a person who has migraines can track what happens in their day when they have a headache, recognize triggers, and change their behavior to have fewer migraines overall. As the lead health data scientist at Evidation Health, a digital health company that helps people track progress on healthy behaviors like steps and sleep, Daza is able to contribute to stats-of-1 projects like a collaboration with the VA to enroll veterans in a personalized heart health program. In the fall of 2022, Stats-of-1 started a podcast, speaking to health experts about how statistics can be applied to a single persons life. 

Entrepreneur: Andrew Parker, founder and CEO of Papa

Courtesy of Papa

After watching his family struggle to balance supporting his ailing grandfather (who they called Papa) with maintaining their daily lives, Andrew Parker founded Papa to connect older adults with paid Papa Pals, most of them college students, who work part-time to provide companionship and help with errands, housekeeping, and technology support. Papa started in Florida, but extended services to all 50 states in early 2021. In October of 2022, Papa, in partnership with Meridian (a Michigan-based provider of government-sponsored health programs) announced the results of a six-month program connecting Medicaid members with Papa Pals, which resulted in 33% reduced healthcare costs for participants.