Forbes 30 Under 30: How 5 Former Honorees Swapped Lavish Multimillion-Dollar Homes for Prison Cells

The Forbes 30 Under 30 list has long been seen as an illustrious honor achieved only by the best and the brightest from a wide spread of industries. But the prestigious feature has earned a much murkier trademark in recent years: foreshadowing the criminal downfall of once-brilliant business leaders.

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.

Theranos founder Elizabeth Holmes, crypto entrepreneur Sam Bankman-Fried, and “Pharma Bro” Martin Shkreli are just a handful of the former honorees whose less-than-savory business dealings have seen them trade boardrooms and megamansions for courtrooms and prison cells.

This trend has not gone unnoticed.

The Guardian 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.”

Even Forbes has acknowledged the unfortunate trend, publishing a “Hall of Shame” list of the “10 most dubious people” to ever be featured in its 30 Under 30 list.

But there is another trend that can be noted among these disgraced honorees: their shared love of high-priced properties. Several of them built up incredibly impressive property portfolios, which they have since swapped for a literal pad behind bars.

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 32 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.

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 40-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.

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.

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.

In 2021, she sold her company to J.P. Morgan Chase for $175 million and was named a managing director. But just a year later, she was terminated from the company and then accused by the bank of wildly inflating the number of student customers by millions, which duped the bank into buying her startup in the first place. Javice was subsequently charged with fraud by the SEC.

Her trial has been postponed until 2025, and she has been reportedly accused of securities fraud, wire fraud, bank fraud, and conspiracy.

Released on a $2 million bond, she has had her travel restricted to New York City and Southern Florida, where she currently lives in a Miami Beach apartment.

Javice purchased the high-floor perch in 2021 for $1.4 million. Located in a 2003-era waterfront tower, the luxe two-bedroom, two-bath condo features 1,500 square feet of living space.

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.