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David Brown
Wondery subscribers can binge all episodes of Business Rebuilding Lego early and ad free Right now. Join Wondery plus in the Wondery app or on Apple Podcasts. When Elon Musk bought Twitter for $44 billion in 2022, it was a seismic event. But nearly three years later, it feels like the purchase might have changed the world forever. This is business Flipping the Bird A behind the scenes look at the Twitter sale and its immediate impact on the way we communicate. This was not the place where you'd expect to find the CEO of one of the biggest tech companies on the planet. Sure it was. In San Jose, California, the heart of Silicon Valley, and Brett Taylor looked the part with his confident smile and receding hairline. Brett was the co CEO of Salesforce, and before that he was an ex Google and Facebook employee and a graduate of Stanford. But on this evening, March 31, 2022, Brett found himself in an unexpected location, waiting for an unexpected guest. San Jose is the heart of the tech industry, filled with sterile corporate architecture, palm trees, malls. Deals often get done in glass panel conference rooms or in classic Silicon Valley restaurants like Bucks or Maderas. But not today. Brett whipped out his phone and fired off a text to two business associates. This wind's for the weirdest place I've had a meeting recently. I think they were looking for an Airbnb near the airport. There are tractors and donkeys. He threw in an emoji of a man shrugging. Besides proximity to a landing strip, it's likely the privacy of this rustic Airbnb was a major selling point. It was far from the prying eyes of tech reporters who'd salivated the chance to be in the room for this meeting. Brett Taylor was at this particular Airbnb surrounded by tractors and donkeys. Not in his role as the co CEO of Salesforce. He was there in his role as the chair of the board of the social media company Twitter. He and Twitter CEO Parag Agrawal needed somewhere safe to meet with one of tech's most notorious power players. Less than a minute after Brett sent his text, he received a response from their guest. Ha ha. Awesome. Maybe Airbnb's algorithm thinks you love tractors and donkeys. Who doesn't? Brett didn't respond to that. Later, he received another text. On my way there in about 15 minutes, Brett spotted something in the distance and typed out a reply. And abandoned trucks in case we want to start a catering business after we meet. Brett was keeping things light and chummy, as if all of this was friendly. Sounds like a post apocalyptic movie set. Brett had to agree. Agreeing was probably in his best interest at the time, because the man Brett was texting had been quietly buying Twitter stock and was now one of the company's largest shareholders. The man they were waiting to meet was Elon Musk. Never mind that the way Musk had accumulated his Twitter stock might have violated secur. He had issued Brett and the rest of the board an give him a board seat or he'd either buy Twitter or start a rival company. And that was why Brett and Parag were meeting with him at this Airbnb to hammer out a deal for Elon Musk to join the board and keep Twitter out of his grasp. As Brett watched the donkeys graze, he must have been asking himself a question, one a lot of people would soon be asking. What exactly was Elon's plan for Twitter? When news broke a few days later that Elon had become Twitter's largest shareholder and was set to join its board, perhaps no one was more surprised than the regular employees inside Twitter.
Jim Redmond
I remember being in Slack at that point and there was. There was a lot of discussion there. There were a lot of people who were not happy.
David Brown
Jim Redmond, a systems engineer in the San Francisco office, would find out about Elon's new stake in Twitter. Like most employees at the company, he found out on Twitter. Jim was willing to wait and see what kind of impact Elon would have.
Jim Redmond
I didn't see him as a genius who could do no wrong. I didn't see him necessarily as a smoke blower. I saw him as an interesting guy. I didn't really see him as a monster or as a hero.
David Brown
No one knew whether Elon was going to save Twitter or destroy it. And no one, not the employees inside Twitter hq, not the board, not the CEO, not even Elon Musk himself could possibly predict how Elon's takeover of Twitter was going to play out. Because the drama that started at this Airbnb in what Elon joked looked like a post apocalyptic movie set, would unfold over the next 12 months across boardrooms, courtrooms and group chats. And it would put careers, fortunes, reputations, lives, and even the future of Twitter itself in jeopardy.
Tallulah Riley
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David Brown
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Jim Redmond
I was excited because Twitter's huge. It's planet scale networking, it's planet scale services. It's millions of people at once, billions of users or billions of accounts at least. So it's exciting to work on something that big and that has that much of an impact.
David Brown
And Jim's job was particularly important. Incident management.
Jim Redmond
So Queen Elizabeth dies, or there's a player who collapses on the field at a football game. When something big like that happens, there's always a huge spike of traffic, and we have to be able to handle it in a timely fashion that has minimal impact on end users. It's tricky, but it's never a dull moment.
David Brown
It was an exciting time to be at the company. And the increased traffic during the pandemic's lockdown gave fuel to Jack Dorsey's business ambitions.
Jim Redmond
Our goal is to more than double our total annual revenue to over 7.5 billion in 2023. We're confident we can hit these goals, and we're confident they will make us even stronger and more valuable to you and people around the world.
David Brown
But even as Jack was touting a bright future for Twitter on investor calls, there were worries that the pandemic boom was simply papering over some major cracks in the business.
Eric Fraunhofer
I mean, In Covid, a lot of people were at home, just like me, looking for something to do.
David Brown
Eric Fraunhofer had been working at Twitter since 2014.
Eric Fraunhofer
They were spending time on Twitter buying things on Amazon. You know, from a short term perspective, it seemed like a pretty good bet that things were going to continue growing like they were.
David Brown
But Eric had seen the warning signs from early in his tenure at the company.
Eric Fraunhofer
When I joined, Twitter wasn't profitable at all. We were burning through cash.
David Brown
And as the pandemic slowly wound down, Twitter's traffic slowed down with it.
Eric Fraunhofer
I think what happens is, you know, Covid starts to end. Things get back to normal. People are spending their time elsewhere.
David Brown
Jack's pledge to double business had always been optimistic. Now it looked hopelessly so.
Eric Fraunhofer
In the end, the growth didn't match the returns. Layoffs felt inevitable to me.
David Brown
None of this slowed Jack's glamorous world tour. But that started to look a lot less like someone who had it all figured out and a lot more like someone who was not paying attention. On the day in January 2021 when Donald Trump was banned from Twitter, Jack was on a secluded island in French Polynesia looking like Tom Hanks in castaway, beard and all.
Jim Redmond
It always felt like Jack was off doing something else. The day to day work was being taken care of by the other people involved.
Eric Fraunhofer
And I think over the years, Jack lost interest in running Twitter and he was more interested in crypto.
David Brown
If some of Twitter's employees had gotten the impression that their boss was quiet quitting, well, Jack finally made it official.
Jack Dorsey
Breaking news this hour. Twitter CEO Jack Dorsey has announced he's stepping down. In a statement put out by Twitter this morning, Dorsey was quoted as saying that he had decided to leave Twitter because he believed the company is, quote, ready to move on from the company's founders. But he didn't provide any additional detail on why he decided to resign to replace Jack.
David Brown
There was no traditional CEO search to fill the job. No outside candidates were seriously considered. Instead, the board picked the Chief Technology Officer, Parag Agrawal.
Eric Fraunhofer
He's the antithesis of Jack Dorsey, right? Jack Dorsey is kind of the billionaire. He has all of these famous friends.
David Brown
Ed Ludlow, a journalist for Bloomberg, extensively covered the succession drama.
Eric Fraunhofer
And at the time, Agrawal was a relative unknown. You know, he's listed on the company's websites in management, but he's ultra focused on his role and what Twitter's doing, technologically speaking.
David Brown
Parag was 37 when he assumed the top job at Twitter. He had joined the company in 2011 and worked his way up the corporate ladder. Publicly, Parag projected a much different Persona than his predecessor. While Jack was off traipsing around the globe with models and celebrities, Parag was every bit the family man. His social media presence was warm, open, and filled with photos of his wife and young son. Jack didn't publicly discuss his reasons for leaving, but in his public resignation letter, he said his belief in Parag was bone deep. To Jim, the systems manager who worked in incident management, Parag seemed to lack some of the key skills that a leader needs.
Jim Redmond
He was definitely learning on the job. There was no question about that. He was not the best, most reassuring speaker because he had spent such a long time as an engineer that he hadn't really built up those public speaking kind of soft skills. So it was not. It wasn't always inspiring to hear from Parag.
David Brown
And while Twitter was in a state of transition under Parag, Elon Musk saw an opening to, in his words, save Twitter, the platform that allowed him to express these pearls of wisdom freely. I put the art in fart. Stop gendering memes. I mean mimes. Just dropping some friends off at the pool. His tweets could be more than just off color gags. One of his tweets, for example, a dumb joke about weed, got him in trouble with the securities and Exchange Commission when he tweeted that he had the money to take Tesla private at the high price of $420 a share. They ended up investigating him for potentially manipulating Tesla's stock price. Elon clearly loved tweeting, but it was arguably hurting his reputation. If he was worried about that, he didn't show it. Instead of backing away from Twitter, he turned his hobby of tweeting to his growing number of followers into a business investment. In January 2022, Elon started quietly buying up Twitter stock, amassing more and more until he'd acquired 5% of the shares, the threshold where he was technically required to notify the SEC of his stake. But Elon didn't file the paperwork. He kept his acquisition quiet until it was time to make his move. And that time was coming soon.
Tallulah Riley
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David Brown
In March of 2022, Elon Musk got a series of texts from his ex wife, Tallulah Riley.
Tallulah Riley
Can you buy Twitter and then delete it please? America is going insane.
David Brown
Tallulah is a B list actress who has had roles in HBO's Westworld and in various made for TV movies. She and Elon had met in 2008 at a bar in London and married and divorced twice, most recently in 2016, but they still stayed in touch that day In March, Tallulah was particularly outraged by one of Twitter's content moderation decisions. Rachel Levine, the first ever trans woman to be named Assistant Health Secretary of the United States, had been named by USA Today as one of their Women of the Year. In response, the conservative website the Babylon Bee had named Levine their Man of the Year. Twitter suspended the Bees account, saying the tweet violated its policies on hate speech.
Tallulah Riley
Tallulah Rage texted Elon, the Babylon Bee suspension is crazy. It was a joke. Why has everyone become so puritanical?
David Brown
A couple of minutes later, she texted another ID to Musk.
Tallulah Riley
Or can you buy it and make it radically free speech?
David Brown
Musk replied a few minutes later, maybe buy it and change it to properly support free speech. Elon hadn't gone public about how much Twitter stock he owned, and he didn't want to. Yet. The next day he tweeted a poll to his followers. Free speech is essential to a functioning democracy. Do you believe Twitter rigorously adheres to this principle? He quickly followed it up with more context. The consequences of this poll will be important. Please vote carefully. More than 2 million Twitter accounts voted in the poll. The result? An overwhelming no. They did not believe that Twitter rigorously followed the principle of free speech. Over the next few days, Elon shared his poll results and a series of tweets critical of the platform. Given that Twitter serves as the de facto public town square, failing to adhere to free speech principles fundamentally, fundamentally undermines democracy, what should be done is a new platform needed? Am giving serious thought to this. Soon after Elon's phone buzzed was a text from someone unexpected. Among the thousands of private text messages that later became part of lawsuits surrounding Elon's purchase of Twitter was this exchange between its founder and its would be owner. Yes, a new platform is needed. It can't be a company. This is why I left. It was Twitter co founder and former CEO Jack Dorsey. Elon asked Jack what this platform should look like. Jack had plenty of thoughts. A new version of Twitter should have no investors dictating policy, no advertisers controlling content. A pure flow of free speech around the globe. He made another surprising admission, one that the public had no idea about. I tried my hardest to get you on our board and the board said no, that's about the time I decided to leave. As hard as it was for me, I think the main reason is the board is just super risk averse and saw you as adding more risk, which I thought was completely stupid and backwards. But I only had one vote in 3% of the company. We can discuss more. The time had come for Elon to show his cards. He revealed the size of his ownership stake to Twitter's board, 5% of Twitter stock, and he presented them with three choices. He could buy the company, he could start a rival platform, or they could give him a seat on the board. It was that choice that led Twitter's board chair, Brett Taylor and Twitter CEO Parag Agrawal to meet with Elon at that strange Airbnb near the San Jose airport in late March 2022. The board had decided it was best to pursue the path of least resistance. Instead of antagonizing Elon, now apparently a sizable shareholder in their company, they'd offer him a seat on the board, and Elon accepted. Later that night, Elon texted Brett and Parag great dinner. He added a smiley face at the end. But Elon wasn't content with simply getting a board seat. He had not stopped buying up more and more Twitter stock. The day after the meeting with Brett and parag, he surpassed 9% the shares, which made him officially the company's largest shareholder. Four days after his meeting with Brett and Parag, and more than a week after he should have filed SEC paperwork, Elon finally made his ownership of Twitter stock Public New this morning, Elon Musk is taking a 9.2% stake in Twitter. The Tesla CEO bought more than 73.5 million shares, according to a regulatory filing. Right away, Elon's phone blew up. Venture capitalist Joe Lonsdale was optimistic, excited to see the stake in Twitter. Awesome. Hope you were able to influence it. I betcha the board doesn't even get a full reporting of the censorship decisions and little cabals going on there. But they should. The lefties on the board likely want plausible deniability. Podcaster Joe Rogan also texted his excitement. Are you going to liberate Twitter from the censorship happy mob? Even Elon's doctor had something to say. Time for a latter day Gutenberg to bring back free speech and buy Twitter. But there were plenty of people who were less thrilled, and some of them used Twitter as the forum to vent. Former U.S. labor Secretary Robert Reich tweeted, so let me get this straight. Elon Musk made $156 million by violating securities laws and he was rewarded with a seat on Twitter's board. And this quote from Stephen Colbert went viral. Elon Musk asked in a poll if we wanted an edit button on Twitter. I'd rather you cancel the accounts of all the Nazis, but an edit button would be nice. Inside Twitter, the top brass simply weren't talking. But Twitter's thousands of employees were to each other. Jim Redman recalls that opinions on Musk were divided.
Jim Redmond
There were people who were a little confused by it, like why is Elon taking interest in Twitter like this? We know he was a pretty heavy user. He still is, but we weren't quite sure why he was going to take an ownership interest in it.
David Brown
Things were moving fast. At 5:30 in the morning Pacific time, Parag posted two tweets announcing the news. I'm excited to share that we're appointing Elon Musk to our board. Through conversations with Elon in recent weeks, it became clear to us that he would bring great value to our board. He's both a passionate believer and intense critic of the service, which is exactly what we need on Twitter and in the boardroom to make us stronger in the long term. Welcome Elon. Elon spent the days between the announcement and his start date getting up to speed. And he texted extensively with paragraph. I have a ton of ideas, but let me know if I'm pushing too hard. I just want Twitter to be maximum amazing. For his part, Parag seemed to warm to Elon's unabashed enthusiasm. I want to hear all of your ideas and I'll tell you which ones I'll make progress on versus not and why. It seemed like that was all the encouragement Elon needed. It would be great to unwind permanent bans except for spam accounts and those that explicitly advocate violence. I would like to understand the technical details of the Twitter code base. This will help me calibrate the dumbness of my suggestions. I used to be CTO and have been in our code base a long time, so I can answer many of your questions. I wrote heavy Duty software for 20 years. I interface way better with engineers who are able to do hardcore programming than with program manager MBA types. Frankly, I hate doing management stuff. I kinda don't think anyone should be the boss of anyone. But I love helping solve technical design problems. In our next convo, treat me like an engineer instead of CEO and let's see where we get to you got it. Maybe the two men could bond over the cold minutiae of coding and bring order to the chaos of Twitter's C suite. They made arrangements to talk on the phone the next day. Things seemed to be going well. But on April 9, the day he was set to join the board, Elon did something to ice this budding relationship. He posted a list of the 10 accounts with the most followers on Twitter and observed that many of those accounts barely tweeted anymore. He cited examples Taylor Swift hadn't tweeted in three months. Justin Bieber had only tweeted once in 2022, and he asked a simple but brutal question, Is Twitter dying? Parag quickly texted him, his tone less friendly. You are free to tweet. Is Twitter dying? Or anything else about Twitter. But it's my responsibility to tell you it's not helping me make Twitter better in the current context. Elon didn't appreciate the reprimand. He snapped back, what did you get done this week? He didn't wait for an answer. Thirty seconds later, he sent another text with a declaration, I'm not joining the board. This is a waste of time. Fifteen seconds after that, he declared war. We'll make an offer to take Twitter private. Coming up on this season of Flipping the Bird. Musk offered about $43 billion to buy Twitter.
Jack Dorsey
You can't break off a deal via tweet.
David Brown
Musk is making a mockery out of it, sharing poop emojis and dismissing the real effort to take it seriously.
Tallulah Riley
He'll like, tweet a thing and then everyone's like, we gotta work on that now.
David Brown
Because he tweeted it.
Tallulah Riley
It seems the markets are still looking for the bottom.
Jack Dorsey
It just felt like everything was kind.
Tallulah Riley
Of descending into chaos.
Eric Fraunhofer
They literally auctioned off the contents of the Market Street San Francisco Twitter head.
Jack Dorsey
Oh my God.
David Brown
Maybe this will work.
Tallulah Riley
Things are going to be okay and.
Jack Dorsey
It just like the next day everything went to hell.
David Brown
From Wondery this is episode one of six, Flipping the Bird Elon versus Twitter I'm your host David Brown. Austin Rachlis wrote this story. Our producers are Nika Singh and Dave Schilling. Julia Lowery Henderson and Karen Lowe are our senior producers. Reporting by Emily Corwin. Production assistance by Emily Locke and Mariah Dennis. Fact checking by Nawal Anjani Voice acting by Michelle Philippe. Consultant is Kurt Wagner, Bloomberg journalist and author of an upcoming book about Twitter and Elon Musk. Sound design by Kyle Randall. Music supervisor is Scott Velasquez for Frisson Sync Senior managing producer is Latha Pantya. Managing producer is Olivia Weber. Coordinating producer is Heather Baloga. Executive producers are Ginny Lauer, Beckman, George Lavender, Marshall, Louie and Jen Sargent. For wondering.
Jack Dorsey
Today is the worst day of Abby's life. The 17 year old cradles her newborn son in her arms.
Jim Redmond
They all saw how much I loved him.
Jack Dorsey
They didn't have to take him from me. Between 1945 and the early 1970s, families shipped their pregnant teenage daughters to maternity homes and forced them to secretly place their babies for adoption in hidden corners across America. It's still happening. My parents had me locked up in.
David Brown
The godparent home against my will.
Tallulah Riley
They worked with them to manipulate me and to steal my son away from me.
Jack Dorsey
The godparent home is the brainchild of controversial preacher Jerry Falwell, the father of the modern evangelical rite and the founder of Liberty University, where powerful men, emboldened by their faith, determine who gets to be a parent and who must give their child away. Follow Liberty Lost on the Wondery app or wherever you get your podcasts.
Business Wars: Flipping the Bird – Elon vs. Twitter | Episode 1 Summary
Release Date: July 9, 2025
Introduction
In the first episode of Flipping the Bird: Elon vs. Twitter, hosted by David Brown, Wondery delves into the tumultuous saga of Elon Musk’s takeover of Twitter. This detailed narrative explores the strategic maneuvers, internal conflicts, and the profound impact of this business battle on the social media landscape.
The Unexpected Meeting
March 31, 2022
The episode opens with Brett Taylor, co-CEO of Salesforce, in an unusual setting—an Airbnb surrounded by tractors and donkeys near San Jose International Airport. Unlike typical Silicon Valley meetings held in sleek conference rooms or trendy restaurants, this rustic location provided the privacy needed for a clandestine discussion. Brett, alongside Twitter CEO Parag Agrawal, awaited Elon Musk, who had covertly amassed a significant stake in Twitter, positioning himself as a major influencer in the company's future.
Notable Quote:
“This is business. Flipping the Bird.” – David Brown [00:00]
Elon Musk’s Rising Influence
Elon Musk’s involvement with Twitter began subtly. By January 2022, he had quietly acquired a substantial portion of Twitter’s stock, eventually surpassing the 5% threshold that mandates SEC disclosure—though he delayed formal filing until strategic leverage was achieved. His intent became clear: to influence Twitter’s direction, especially concerning content moderation and free speech policies.
Employee Reactions and Uncertainty
Inside Twitter, reactions were mixed. Jim Redmond, a systems engineer, expressed ambivalence:
“I didn't see him as a genius who could do no wrong. I saw him as an interesting guy.” – Jim Redmond [05:07]
This uncertainty mirrored the broader sentiment within the company about whether Musk would be a savior or a disruptor.
Leadership Transition
Amid these tensions, Twitter's CEO Jack Dorsey stepped down in favor of Parag Agrawal, signaling a new era for the platform. Agrawal, seen as the antithesis of Dorsey, was perceived by some employees as lacking the visionary leadership necessary to counter Musk’s ambitions.
Notable Quote:
“He's the antithesis of Jack Dorsey.” – Eric Fraunhofer [15:11]
Musk’s Motives and Strategic Moves
Musk’s motivations were multifaceted. Frustrated by Twitter’s content moderation decisions, exemplified by the suspension of the Babylon Bee for a satirical piece, Musk advocated for a platform with minimal censorship. His belief was that Twitter’s role as a public town square was compromised by restrictive policies.
Key Interaction: Elon’s ex-wife, Tallulah Riley, played a pivotal role by urging Musk to intervene:
“Can you buy Twitter and then delete it please? America is going insane.” – Tallulah Riley [20:03]
This personal plea catalyzed Musk’s public stance on acquiring Twitter, culminating in a poll he conducted:
“Free speech is essential to a functioning democracy. Do you believe Twitter rigorously adheres to this principle?” – Elon Musk [20:09]
The poll revealed widespread dissatisfaction, further validating Musk’s interventionist approach.
Boardroom Negotiations and Escalation
The episode details the critical meeting at the secluded Airbnb, where Musk presented the Twitter board with three options: buy the company, start a rival platform, or grant him a board seat. Opting for the least confrontational path, the board granted Musk a seat, allowing him greater influence without immediate ownership.
Notable Quote:
“It was that choice that led Twitter's board chair, Brett Taylor, and Twitter CEO Parag Agrawal to meet with Elon...” – David Brown [15:36]
However, Musk’s ambitions were not satiated. Shortly after joining the board, he increased his stake to over 9%, officially becoming Twitter’s largest shareholder. This move intensified tensions, leading to Musk’s abrupt decision to abandon the board role and propose a full acquisition.
Turning Point:
“I'm not joining the board. This is a waste of time.” – Elon Musk [27:02]
Following this, Musk publicly offered to buy Twitter for approximately $43 billion, marking the escalation from board influence to outright ownership.
Internal Strife and Public Reactions
Musk’s aggressive tactics stirred significant controversy both within and outside Twitter. Employees were divided, with some admiring his boldness and others fearing the uncertain future he represented. Public figures and commentators weighed in, some supporting his free speech agenda, while others criticized his approach as manipulative and destabilizing.
Notable Reactions:
“They were spending time on Twitter buying things on Amazon... ending up burning through cash.” – Eric Fraunhofer [13:00]
“He'll like, tweet a thing and then everyone's like, we gotta work on that now.” – Tallulah Riley [30:36]
Conclusion and Anticipation for Season Two
The episode concludes with the aftermath of Musk’s hostile takeover bid, setting the stage for a multi-part series that promises to explore the ongoing battle’s ramifications on Twitter’s infrastructure, corporate governance, and its role in global communication.
Final Thoughts:
“Things are going to be okay...” – Tallulah Riley [30:58]
David Brown teases the continuation of the story, emphasizing the high stakes involved as Musk seeks to transform Twitter into his vision of an unregulated free speech platform.
Production Credits
The episode was meticulously crafted by a dedicated team, including writers, producers, sound designers, and consultants, ensuring a comprehensive and engaging narrative of one of the most significant business battles of the decade.
Notable Contributors:
Key Takeaways
Strategic Acquisitions: Elon Musk's methodical accumulation of Twitter stock showcased a calculated approach to gaining control over a major social media platform.
Leadership Dynamics: The transition from Jack Dorsey to Parag Agrawal highlighted internal struggles and differing visions for Twitter’s future.
Free Speech vs. Content Moderation: Musk’s emphasis on unbridled free speech clashed with existing moderation policies, igniting debates about the balance between expression and regulation.
Corporate Maneuvering: The negotiations and eventual hostile takeover bid underscored the complexities of boardroom politics and shareholder influence in modern corporations.
For those interested in the intricate battle between Elon Musk and Twitter, and its broader implications on business and communication, this episode of Business Wars provides an in-depth and compelling exploration.