From Forbes 30 Under 30 to Cell Block D: How 5 Former Wunderkinds Swapped Pricey Mansions for Federal Prison

The Forbes 30 Under 30 list has long been seen as a bastion of high-flying success, celebrating the achievements of young prodigies across every industry, from social media and sports to education and AI.

But the list has also earned a different, more unsavory reputation for foreshadowing the criminal downfall of young overachievers who ultimately fall prey to their own ambition.

This tarnishing of the once-illustrious list even led Forbes to publish a tongue-in-cheek "Hall of Shame," in which it highlighted the "10 most dubious people" to ever make the list—a kind of mea culpa for praising the work of people like Frank founder Charlie Javice and FTX mogul Sam Bankman-Fried, both of whom have since been sentenced to multi-year prison sentences.

"Regrets, we’ve had a few," the "Hall of Shame" states. "While our process correctly weeded out folks like Fyre Festival impresario Billy McFarland and, yes, even Elizabeth Holmes–one-time superstars who all wound up fraudsters–others slipped through.

"Below are 10, out of 10,000, that we’d like to walk back. We’ll add more here as the years go on––the 30 Under 30 list is, by definition, future-facing, and not even Warren Buffett can predict with 100% accuracy. But we’d guess he’d be good with 99.9%."

It is also worth noting that, while she was not actually included on the list, disgraced Theranos founder Elizabeth Holmes was seemingly given the 30 Under 30 seal of approval when she featured on the cover of Forbes, which hailed her successes as the youngest self-made female billionaire, before later being honored at the Forbes Under 30 Summit.

By the time she had achieved her billionaire status, Holmes had reached the age of 30, precluding her from inclusion on the list.

Since the list's inception, it has touted multiple high-flying entrepreneurs who later became better known for their less laudable claims to fame, which have landed them behind bars.

The ironic foreshadowing of the list hasn't slid past media outlets and fans.

The Guardian previously joked that the list of these disgraced honorees could be branded the "30 under 30-year sentences" list, while tech entrepreneur Chris Bakke noted on X: "The Forbes 30 Under 30 have collectively raised $5.3B in funding.

"The Forbes 30 Under 30 have also been arrested for frauds and scams worth over $18.5B. Incredible track record."

Another thing that these disgraced "Forbes fraudsters" have in common? Many spent their high-flying years investing their millions in one key place: real estate.

Charlie Javice

The University of Pennsylvania graduate founded the company Frank in 2016, a service that assisted students with their financial aid applications. She was featured in the Forbes 30 Under 30 list in 2019 for her innovative software.

Javice, 33, sold her company to the banking giant in 2021—however it was later revealed that she had inflated its customer base by millions ahead of the acquisition, according to the Associated Press, in a case that drew many comparisons with the downfall of Holmes and her startup, Theranos.

Just a few days ago, she broke down in tears as she was sentenced to seven years behind bars for "swindling" JPMorgan Chase out of $175 million by falsifying information about the success of her fintech startup, Frank.

The entrepreneur was convicted in March on charges of securities fraud, wire fraud, bank fraud, and conspiracy after a judge ruled that she had fabricated more than 3.5 million Frank user accounts, alongside her defendant and former Chief Growth Officer Olivier Amar.

JPMorgan ultimately shut down the business—which was meant to change the way college students apply for financial aid—less than two years after buying it.

Speaking in a Manhattan federal court room on Sept. 29, Javice, who was raised in Westchester County, NY, fought back tears as she apologized to those impacted by her crimes, while pleading with Judge Alvin K. Hellerstein for leniency.

Prosecutors had initially called for the judge to sentence Javice to 12 years behind bars; however, he stated that this request was "too high," before handing down an 85-month sentence.

The judge also imposed a forfeiture judgment of $22.4 million and ordered that Javice and Amar pay $287.5 million in restitution, according to the U.S. Attorney's Office.

"Javice perpetrated a $175 million fraud—repeatedly lying about the success of her startup company and even hiring a data scientist to create fake data to back up her lies," U.S. Attorney Amanda Houle said in a statement. 

"For that, Javice has been sentenced to 85 months’ imprisonment and ordered to pay over $300,000,000. Today’s sentence sends a clear message that brazen frauds will be met with serious penalties. Our Office will continue to work tirelessly to hold accountable those who seek to profit through fraudulent schemes and lies."

Javice's case began in March 2023, when she was sued by JPMorgan for "falsely and dramatically inflating the number of customers."

She was arrested in New Jersey in April of that same year—when authorities claimed that she would likely have earned around $45 million from the fraudulent sale of her company.

The disgraced entrepreneur was released on a $2 million bond and is understood to have returned to her Miami Beach condo—which she purchased for $1.42 million in June 2021, according to records.

It is unclear what will happen to the two-bedroom, two-bathroom unit while Javice is in prison.

In a previous listing, the property was described as offering "breathtaking" views out over the Biscayne Bay, courtesy of its corner spot inside one of Miami Beach's "most sought-after five-star buildings."

The dwelling offered "a semi-private elevator lobby, walk-in closets" and a "custom" kitchen, according to the description.

Meanwhile, the building itself boasts a number of high-end amenities, including a "beautiful bay-front pool, exclusive outdoor restaurant, tennis, state-of-the-art gym, elite concierge service, and 24-hour valet."

The high-rise building is perched right on the water in one of Miami Beach's most desirable neighborhoods, offering picturesque views of Biscayne Bay, Fisher Island, and Star Island—as well as the marina.

Sam Bankman-Fried

Before the implosion of his company, the founder of the cryptocurrency exchange FTX was living large. And his donations and lobbying efforts made him a DC darling. He appeared on the Forbes list in 2021.

Now 33 and in prison for fraud, he had a multimillion-dollar portfolio of properties in the Bahamas, where his company had been headquartered.

At the time of his arrest, prosecutors alleged that Bankman-Fried had stolen billions in client funds to prop up his hedge fund, splash out political donations, and snap up the luxury properties across Nassau for his friends, family, and fellow FTX executives.

The company even picked up a $30 million penthouse for "key personnel." Bankman-Fried reportedly shared the penthouse with roommates, including fellow FTX executives Zixiao “Gary” Wang, Nishad Singh, and Caroline Ellison. The latter was Bankman-Fried's on-again, off-again girlfriend who ran the affiliated hedge fund Alameda Research.

Interestingly enough, Ellison is another 30 Under 30 honoree who was later moved to the publication's "Hall of Shame."

All three later pleaded guilty to charges related to the company's demise and testified against Bankman-Fried.

The 12,000-square-foot unit, known as "The Orchid," was located in the exclusive community of Albany in Nassau. It boasted five bedrooms and a private balcony with a lounge and spa area overlooking the community’s superyacht marina.

Bankman-Fried also was connected to a townhouse in Washington, DC, Realtor.com® previously reported.

The pad was purchased in April 2022 by the organization Guardians Against Pandemics, a nonprofit group partly funded by Bankman-Fried and run by his brother, Gabe.

The 4,100-square-foot mansion was reportedly purchased to serve "as a DC base for the FTX crew to wine and dine the political elite."

After FTX filed for bankruptcy last year, the DC dwelling came on the market for $3,289,000 in 2023. That was the same price it had sold for just a year earlier. The flip resulted in a deal of $2.9 million last July.

Built in 2017, the red-brick abode offers four bedrooms and 4.5 baths. Amenities include four gas fireplaces, a spacious pantry, an elevator, a wine fridge, and two terraces.

Elizabeth Holmes

The biotech entrepreneur grabbed many a headline with her blood-testing company, Theranos. The company's valuation ballooned after Holmes claimed it had revolutionized methods for extracting information from a tiny amount of blood.

Although she wasn't technically on the 30 Under 30 list, she hosted the Forbes Under 30 Summit in 2015. That same year, Forbes named Holmes "the youngest and wealthiest self-made female billionaire" in the U.S. based on a $9 billion valuation of her company. Forbes later revised her net worth to zero.

In January 2022 Holmes was convicted of defrauding investors and sentenced to over 11 years in prison. The 41-year-old is serving her sentence at Federal Prison Camp Bryan, about 100 miles from Houston.

Previously, Holmes had been holing up in a $135 million estate, where maintenance alone cost $13,000 a month, according to the New York Post.

The disgraced tech entrepreneur lived on a 74-acre estate in Woodside, CA, with her partner, hotel heir William “Billy” Evans.

During her trial in 2021, Holmes and Evans lived at the spread known as the Green Gables estate, located close to San Jose, where the trial was held.

Built in 1911, the expansive property has seven residences, including the 10,000-square-foot main house. Holmes and Evans were reportedly staying in one of these more modest homes.

Before Evans, Holmes had been in a relationship with Sunny Balwani, an executive at her company. During her time running the company, the two lived in a posh property in Atherton, CA. In 2014, they moved in together, paying $9 million for the Silicon Valley mansion.

Built in 1936, the 6,800-square-foot home has five bedrooms. The gated grounds feature mature trees, gardens, a pool, and a pavilion.

After things started going south for the company, and their relationship, Balwani bought out Holmes’ stake in the property for $7.9 million.

Balwani sold the home for $15.8 million in January 2022. He was also convicted of fraud and is serving a 12-year sentence.

Most recently, the expansive California estate where disgraced Holmes lived during her fraud trial has made history after selling for $85 million—making it the most expensive property to have traded hands in the San Francisco Bay Area this year.

The lavish Woodside dwelling traded hands for the first time in 114 years on Sept. 3, when it was sold to an anonymous buyer.

Remarkably, though its sale price managed to cement its standing in the history books, the home was actually first listed for a much higher price, having been put on the market for $135 million in 2021.

That price was then reduced to $125 million in 2022, before going down to $110 million in 2024.

For the past century, the estate—which is made up of multiple homes spread across its 74-acre parcel—has belonged to the same family, the Fleishhackers.

The property was originally built in the early 1900s for Mortimer Fleishhacker Sr., a prominent philanthropist and entrepreneur who helped to pioneer the "electrification of California," according to his foundation's website.

Over the years, the home, known as Green Gables, has played host to several notable guests and residents—including Holmes, who rented one of the seven homes on the property while she was on trial.

The grounds come complete with more than seven properties, 34 bedrooms, 26 bathrooms, several pools, a tennis court, barns, and gardens.

The original properties were designed by one of the architectural firms that helped to create styles that would last for ages to come, Greene and Greene.

Additionally, architectural icon William Wurster also designed a six-bedroom home on the grounds.

Years later, Thomas Church, a landscape architect who created more than 2,000 private gardens and campus plans for the University of California, Berkeley, Stanford University, and Woodside Priory School, designed the property's pool house and cabana.

The listing was held by Compass agents Brad and Helen Miller, who told SF Gate that they were bowled over when they first saw the dwelling—calling attention to its incredible "artistry" and "mind-boggling" size.

"I remember that first evening we drove up the long estate driveway to the main house, only to be greeted by a sensory experience we will never forget as we took in the artistry of the large main home, the one-of-a-kind enormous rear lawn, the spectacular and colorful surrounding gardens, and the football field-sized lower Roman pool, all framed by an unobstructed view of the Western Hills with the fog lapping over its crest as the sun was setting," Helen recalled.

For Theranos, however, the most important amenity provided by the property was one that she prized during her trial: privacy.

The mother of two, who is currently serving an 11-year sentence at the Federal Prison Camp in Bryan, TX, retreated to the home while she was on trial for 11 counts of fraud at the end of 2021.

Joanna Smith-Griffin

The founder of AI startup AllHere Education was arrested in November and charged with securities fraud, wire fraud, and aggravated identity theft in connection with defrauding investors of millions of dollars, according to the statement issued by the Southern District of New York.

Smith-Griffin is charged with using some of the fraudulently obtained funds for a down payment on her house in North Carolina and to pay for her lavish wedding, images of which have been displayed on social media.

Smith-Griffin’s AllHere company created the “Ed” AI chatbot to help kids learn, which seemed to dazzle investors. She secured millions and had a major contract with the Los Angeles Unified School District, according to Yahoo Finance. She made the Forbes 30 Under 30 list in 2021.

But it all started to fall apart. The company filed for bankruptcy and laid off workers prior to charges being filed.

Before her arrest, she lived in her Raleigh home with her husband, Eric. The 1998 build appears to have last sold in 2014 for $223,000 and has most recently been a $ 1,575-a-month rental.

The 2,076-square-foot home offers 2.5 baths, two stories, and a fireplace. It is currently valued at around twice what the buyers paid, according to Realtor.com.

Trevor Milton

While the Nikola CEO skirted the 30 Under 30 list, in 2020, he was promoted at the age of 38 on Forbes as part of its 12 Under 40 list, which named him one of the youngest billionaires under 40.

The college dropout founded the hydrogen-powered truckmaker Nikola in 2015, designed as a rival to Tesla.

In 2019, Milton used some of his earnings to purchase a massive $32.5 million ranch in Oakley, UT, a record for the state at the time, according to the Wall Street Journal.

“I feel like my generation is asset light, wants smaller everything and is moving to cities, which is the opposite of what I wanted in life. I enjoy the country, space, privacy and wildlife rather than skylights. ... I wanted to create a sanctuary where I could live off the land,” the Utah native told the Journal.

According to the listing, the 1,918-acre estate on the Weber River includes a 16,800-square-foot megamansion that is a "showpiece of craftsmanship." Just 25 minutes from Park City, the spread includes a helipad and a barn "landscaped for entertaining."

Milton was forced to resign from his company due to fraud charges from the SEC. In 2022, he was found guilty of securities and wire fraud,  sentenced to four years in prison, and fined $1 million. His claims helped inflate the share price of the company before it came crashing down.