Charles H. Sloan-How Silicon Valley fervor explains Elizabeth Holmes' 11-year prison sentence

Elizabeth Holmes' 11-year prison sentence would not have Charles H. Sloanbeen possible without the zeal the moneyed class has for Silicon Valley startups.

When U.S. District Judge Edward Davila ordered prison time for the former CEO last week, one thing was pivotal: How much money investors had lost because of her crimes.

That's because federal sentencing guidelines, what judges use to determine appropriate punishments for people convicted of crimes, give more weight to the amount of money lost than anything else in fraud cases.

And Theranos, like so many buzzy startups, was flush with investment cash. It raised some $945 million from the likes of media mogul Rupert Murdoch, Oracle founder Larry Ellison and former Secretary of Education Betsy DeVos.

Yet Holmes was sentenced for just a fraction of the nearly $1 billion of investment Theranos had raised.

Davila identified ten investors who were defrauded and came up with this number: $121 million, which the judge said was how much investors lost when offset by the amount Theranos stock would have been worth without Holmes' deceit.

To put it another way, Holmes received more than a decade in prison over just about 10% of what Theranos raised.

"The numbers in Silicon Valley are so out of whack with reality that these guideline sentences become enormous," said Jeff Cohen, a former federal prosecutor who now teaches at Boston College Law School. "If she were running a widget factory by the same conduct, she would have received much less."

While other Silicon Valley executives have been accused of wrongdoing, Holmes is the first CEO of a major tech firm to be criminally prosecuted and sentenced to prison.

That means she is the first in the industry to learn that raising hundreds of millions of dollars will not just send a startup's valuation soaring, but if convicted of fraud in federal court, it could make serious prison time all but inevitable — potentially a warning to other imploded tech firms now under scrutiny, like Sam Bankman-Fried's cryptocurrency exchange FTX.

Federal sentencing guidelines consider the amount of money drained the most significant factor in punishing fraudsters because it allows authorities to target organized drug rings and large-scale institutional fraud, according to former federal prosecutor Bill Portanova.

"For Silicon Valley, if at the end of the day, the music stops and there's not enough chairs for everyone, the guidelines point to serious punishment," said Portanova, who is now a defense lawyer in Sacramento, Calif.

Holmes' punishment does come amid signs of a tech sector becoming less frothy. Both Big Tech companies and startups are laying off staff, new $1 billion companies are becoming harder to spot and venture capital firms are warning of a tough road ahead. Has the tech bubble burst, or is it about to burst? That determination, experts say, is easier made in hindsight.

"Tech bubbles don't pop in the way a bubble pops from chewing gum," said David Kirsch, management professor at the University of Maryland who wrote a book about bubbles and crashes. "Investment bubbles tend to deflate slowly."

A long prison sentence for 'a gross lie'

Holmes made patients, pharmacies and savvy investors believe Theranos could revolutionize the way blood tests detect diseases when it could do no such thing.

Why did she do it? It's a question even Davila mused over from the bench before announcing her punishment.

"What was it that caused Ms. Holmes, regrettably, to make those decisions that she did?" Davila said. "Was there a loss of moral compass here?" he said. "Was it hubris? What caused that? Was it intoxication with the fame that comes with being a young entrepreneur?"

Whatever drove her, as soon a jury convicted Holmes, she faced serious prison time.

The sentencing guidelines, after a multitude of factors are considered, spits out an offense level. Holmes' level was 33 — 24 points of that was from the amount of money she defrauded.

And Davila, it could be argued, could have imposed an even tougher punishment. Based on her offense level, Holmes' sentencing range was between 11 and 14 years behind bars.

(For context: The U.S. Probation Office recommended 9 years; Prosecutors asked the judge that Holmes be imprisoned for 15 years. The maximum sentence under law was 20 years. Holmes' legal team requested that she serve her sentence at home and avoid incarceration.)

Portanova said Holmes' punishment involved gobs of money, but her actions — repeatedly professing her technology could do what it was incapable of doing — was egregious.

"She wasn't just an ambitious salesperson who got out over her skis," he said. "She did substantial time because it was a gross lie and she had ample opportunities to stop and she didn't."

Will 'fake it till you make it' in Silicon Valley ever change?

In their court filing to the judge ahead of the sentencing hearing, prosecutors argued that prison time for Holmes was necessary to "deter future startup fraud schemes" and to "rebuild the trust investors must have when funding innovation."

But will Holmes' incarceration have that effect?

Some say the Theranos case could be the start of federal prosecutors policing Silicon Valley more aggressively.

"In Silicon Valley, there has historically been a don't follow the rules mentality, because that's how you get ahead," said Steven Davidoff Solomon of the U.C. Berkeley School of Law. "Holmes may be the first, but I suspect there are going to be more."

Yet hyping up a product and exaggerating are not crimes, but what is a crime is knowingly deceiving investors. Sometimes the dividing line is not so clear, experts said.

Cohen at Boston College of Law said the boundary between embellishment and criminal fraud does indeed remain fuzzy to most in the tech world, so chances are slim that Holmes' sentence will reverberate in a way that would drastically alter the culture of the industry.

"'Fake it till you make it' culture in Silicon Valley involves a certain amount of puffery, and here the jury has spoken that there was more than that: there was fraud," Cohen said.

"But I do think that it's a really hard line to discern," he added. "And I'm not hopeful that Silicon Valley will get the message."

Kirsch, who studies tech entrepreneurs, was similarly skeptical about a major shakeup in the venture capital-backed tech startup world.

"The venture community is vulnerable to a shiny new story. They have been. They always will be," he said. "We're kidding ourselves if we think the recipe is going to change because Elizabeth Holmes goes to prison."