Why is Ryan Selkis so angry? Inside the Messari CEO’s jump from Biden to Trump

Ryan Selkis likes to pick fights.

The crypto CEO has publicly called Silicon Valley grandees Reid Hoffman, Vinod Khosla, and Ron Conway “old washed-up bitches.”

He has said that “our national leaders are pussies.”

He’s challenged billionaire Mark Cuban, a pro-crypto Democrat, to duke it out.

And he’s reserved his greatest vitriol for Gary Gensler, the chair of the US Securities and Exchange Commission, whom he has called a rat, snake, liar, fraud, loser, beta, toady, sociopath, and the Grinch, among other terms of endearment.

“This government and its proxies deserve total wrath,” Selkis wrote in late April.

Crypto’s more well-mannered inhabitants may wince at his antics, but they can’t deny that Selkis, the 38-year-old co-founder and CEO of the crypto analytics company Messari, is one of the industry’s more influential movers and shakers.

Deep connections

He has almost 360,000 followers on X.

He drafted a playbook to put crypto front and centre in the 2024 election and helped strengthen FairShake, a super PAC that has raised almost $180 million to spend on pro-crypto candidates.

And he has deep connections with some of crypto’s biggest power players. He counts Coinbase CEO Brian Armstrong and venture capitalist Fred Ehrsam as personal contacts. And Messari is backed by the likes of Mike Novogratz’s Galaxy Digital and angel investor Balaji Srinivasan.

Selkis’ business has also caught the eye of Wall Street players. Point72 Ventures, the firm led by Steve Cohen, the hedge fund billionaire and owner of the New York Mets baseball team, is a Messari investor.

‘I have no idea what his deal is.’

—  Mark Cuban

In contrast with Armstrong, who positions himself as a calm, non-partisan advocate for crypto, Selkis has thrown his voice behind former president Donald Trump in his campaign for reelection — and grown more bellicose in the process.

“My rhetoric has been a one-way crescendo for about six months,” he told me.

He insists his name-calling is a counterpunch. None of his insults are “first strikes,” he says.

The main target of Selkis’ ire is the SEC, which has ramped up its litigation against crypto companies since the collapse of Sam Bankman-Fried’s FTX in November 2022.

Selkis, who says he voted for President Joe Biden in 2020, considers the agency to be his mortal enemy and found an ally in Trump — a political shift that mirrors crypto’s broader Trump-ward tilt.

However, Selkis’ taste for hostile language and name-calling is divisive.

“I have no idea what his deal is,” Mark Cuban, the Shark Tank celebrity and billionaire investor, told me in an email.

“He knows exactly what my deal is,” Selkis countered in one of several interviews with DL News.

Reid Hoffman, the co-founder of LinkedIn, also expressed bafflement. “Reid has no idea what Selkis is talking about,” a spokesperson for the billionaire said in response to a query about Selkis’ claims of Hoffman’s role in a “shadowy cancellation campaign” against him.

Consistent antics

Selkis’ public belligerence has also divided former employees.

He is trying to force his own agenda in his attempts to promote the industry, said one. “His delivery is destructive,” the person said.

Another was more measured. “I think his antics have been pretty consistent for the last seven or so years,” they said, though his online chatter has recently become a bit more aggressive.

Some customers have expressed concerns, too, Selkis said. He assured them that he was okay. As for Messari, Selkis said his public commentary hasn’t impacted the business.

More than a dozen people, including competitors, investors, as well as former and current employees, did not respond to my requests for interviews about Selkis and his behaviour.

‘The SEC is a corrupt institution that must be incinerated and rebuilt from scratch.’

—  Ryan Selkis

Bald, bearded, and burly, Selkis lives with his wife and four children in his five-bedroom house in the suburbs of Baltimore. He has a BA from Boston College. His crypto company was reportedly valued at $300 million as of its last funding round.

By most measures, he lives a charmed life. Why, then, does he seem so pissed off?

Twobitidiot

At the end of the workday in late June, Selkis called me from his home.

On the wall behind him hung a signed photograph of Australian golfer Greg Norman. “PLAY HARD. ATTACK LIFE,” wrote the golfer above his signature.

Selkis theatrically cracked open a can of craft beer from a Brooklyn brewery. “Cheers, mazel tov,” he said to me at one point in the interview, sipping from his brew.

At 6 feet 5 inches tall, the CEO comes across as a boisterous crypto bro from central casting. His username on X is “twobitidiot,” and he regularly posts about drinking IPAs.

In conversation, Selkis is measured, but still a bit trollish.

In his home office, he has a telescope he bought for his children. At one point, I jokingly asked him if he uses it to spy on his enemies.

“No, that I do just fine online,” he quipped.

Selkis started his career in investment banking and venture capital. Eventually, he snagged positions as an executive at Digital Currency Group and then CoinDesk.

He’s raised about $61 million over multiple funding rounds for Messari, the crypto analytics company he co-founded in 2018.

Selkis says his public persona is “dumb like a fox.”

“I can be whatever character or put on whatever mask is required at the time — publicly,” he told me. “I don’t change privately.”

Down with the SEC

Selkis dons his masks to a simple end: a complete overhaul of the SEC.

“The SEC is a corrupt institution that must be incinerated and rebuilt from scratch,” he posted on X in June.

The SEC did not respond to a request for comment.

His opposition to the regulator stems from his belief that it’s acting in bad faith. Rather than treat crypto as a new asset class worthy of its own laws, the agency is committed to regulating it in the same way it polices the stock market.

Beginning in 2018, the SEC filed regular litigation against crypto companies. (As it happens, this occurred during Trump’s presidency.)

And, in 2023, the agency ramped up its crackdown and targeted some of the industry’s biggest players, including Coinbase and Binance.

If the SEC prevails in its lawsuits, issuers of tokens will have to register the same way companies issuing shares do, plus shoulder the costly burden of making regular financial disclosures.

This would be bad for Messari.

Selkis compares Messari’s product to EDGAR, the online database where the SEC publishes the financial filings listed companies submit to the agency.

Customers depend on Messari for in-depth reports on blockchain ecosystems like Solana, as well as data on the prices of cryptocurrencies, or the amount of money crypto startups have raised.

(Disclosure: Llama Corp, the parent of DL News, provides some of the same services.)

Messari’s fortunes are directly tied to the rise and fall of the crypto industry. If it goes to zero, so will the need for analytics.

Selkis 2024

So, Selkis has looked for help from politicians.

Since 2018, he has personally contributed more than $115,000 to political candidates, many of whom are explicitly pro-crypto, according to filings with the Federal Elections Commission.

With more recent donations to Trump, he said that number is now closer to $200,000.

He’s even considered entering politics himself.

In September 2021, he announced that he planned to run for the US Senate. “Selkis 2024,” he wrote in a since-deleted post on X. “Time to activate the crypto political machine.”

Selkis told me that he eventually decided against a Senate race because he didn’t believe he could win in the blue states where he resides: New York, Massachusetts, or Maryland.

However, he didn’t step away from the political arena.

In 2022, he pleaded crypto’s case in an interview with Tucker Carlson on Fox News and said he founded the Digital Freedom Alliance to advocate for the industry on Capitol Hill.

Project Leonidas

The next year, after a February meeting with Brian Armstrong, Fred Ehrsam, and other crypto power players, he drafted a battle plan he called “Project Leonidas.”

The pro-crypto campaign involved significant fundraising solicitations of industry executives.

He eventually funnelled his connections into the already extant FairShake and rolled up the Digital Freedom Alliance’s operations underneath the super PAC’s banner.

By December, Armstrong and other deep-pocketed members of the crypto elite had contributed $80 million to the cause.

‘It wasn’t clear to me whether Trump was the chemo or the cancer.’

—  Ryan Selkis

Around then, Selkis said he handed off the daily operations of FairShake to political consultants.

“I told my wife, and then I told my team, ‘I can finally tap out of politics for the next year,’” he said.

But he didn’t stay out for long.

In January, Vivek Ramaswamy, a pharmaceutical executive and entrepreneur, ended his long shot bid to become the Republican Party’s presidential nominee and endorsed Trump.

Ramaswamy was Selkis’ presidential candidate of choice, but Selkis soon found another champion in Trump.

A “right-leaning libertarian,” Selkis was initially turned off by the drama of Trump’s first four years in the White House.

“It wasn’t clear to me whether Trump was the chemo or the cancer,” he told me.

But when the Messari CEO moved from New Jersey to the Beltway in 2020, he got an inside look into the difficulties of navigating the capital’s political scene and began to empathise with Trump, he said.

Finally, he did some basic maths.

Under Trump, the total value of all cryptocurrencies increased fivefold between 2017 and early 2021, to $1 trillion, according to data from CoinGecko.

For the bulk of Biden’s term, the market has been relatively flat, he said. While the market value of crypto hit an all-time high of $3 trillion in November 2021, it has settled at $2.5 trillion after a severe contraction in 2022.

“Ball don’t lie,” Selkis, a basketball player in high school, told me.

Rhetorical journey

Initially, Selkis planned on supporting Trump privately, not publicly.

Crypto has long been amenable to Trump-style politics, and business leaders are often right-leaning.

Selkis acknowledged this, but he was wary of blowback for becoming an explicit Trump supporter.

“The risky thing is saying it out loud and saying it loudly,” he told me.

Selkis likes Trump’s long-standing promise to reduce the size of the federal government and curtail what his supporters call “the Deep State” of Washington’s bureaucracy.

Builders and creators

Selkis hopes for less government and more freedom for “builders and creators.”

Even though Trump was convicted in June of 34 felony counts of falsifying business records to cover up payments to porn star Stormy Daniels, Selkis believes the criminal prosecutions of the former president are “political charades.”

“We don’t elect angels, we elect leaders,” he told me, in reference to Trump’s character.

For Selkis, debates over Trump’s character or his policies are ultimately secondary. He’s largely a single-issue voter, and he believes Trump beats Biden on crypto, full stop.

More Trumpian

Selkis has deleted his X history up until late April, but by then, his rhetoric had become more overt.

“We have one shot at this: ensure a Trump presidency takes on the Deep State and is populated by libertarian-leaning cabinet members,” he posted.

As Selkis grew more Trumpian, he saw that, at least on Crypto Twitter, no one cared.

Moreover, because of his large platform on X, he hoped his increasingly vocal support would prompt Trump’s campaign to reach out.

It did, he said, but he declined to say who he’s connected to in Trump’s camp. The Trump campaign did not respond to a request for comment.

Crypto president

In May, Selkis’ public support of Trump reached an inflection point when he flew down to attend a gala at Mar-a-Lago, Trump’s Florida resort, for holders of Trump NFTs.

“If you’re in favour of crypto you’re gonna vote for Trump,” said the former president during the event.

As Trump was fielding questions from the audience, the CEO of Messari heard his name called mid-salad bite. He went to the stage, said a few words, and then shook Trump’s hand.

Afterwards, Selkis decided to “double, triple, like 100x down” on his support for the former president.

Since then, other crypto CEOs have come out in support of the former president.

These include Tyler and Cameron Winklevoss, the co-founders of crypto exchange and custodian Gemini, and Jesse Powell, the former CEO of crypto exchange Kraken.

“I think it’s hard to deny that I’ve had a pretty material impact on shifting things,” he said.

Neither the Winklevoss twins nor Powell responded to a request for comment on whether Selkis’ rhetoric encouraged them to publicly support Trump.

‘Unifier of genius’

Since May, Selkis’ online bombast has grown even more off-the-wall.

“Study Gandalf and the Balrog,” he posted in mid-June. “Lessons there,” he said in an apparent allusion to taking a stand, as the wizard Gandalf does in “The Lord of the Rings” against a demonic monster.

“I am crypto’s Thanos. The unifier of genius,” he wrote one week later, in reference to the supervillain from the Avengers movies.

And he can’t stay off social media.

From mid-June to July, he posted an average of 117 times per day, regularly tweeting between 3 and 5 am New York time, according to an analysis I did of his X account.

Selkis, who told me he wakes up early to get on edge on competitors, is mindful of how his rhetoric may be perceived and says he’s engaged in a coordinated “information war.”

“Is this issue going to create too much of a divergence between me and my personal comms strategy and the company and our product strategy?” he wondered in June.

No investor in Messari was willing to talk with me about Selkis. His co-founder, Dan McArdle, didn’t respond to repeated requests for an interview.

Selkis told me in early July that he’s dialling down on his posts.

Yet after the assassination attempt on Trump on July 13, this changed.

“A lot of people cosplay at anger,” he posted. “It’s difficult for me to function right now, I am so consumed with rage.”

Ben Weiss is a Dubai Correspondent at DL News. Got a tip? Email him at bweiss@dlnews.com.