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Twitter's Ev Williams Was A 'Terrible' CEO Who Created 'Organizational Pileup' In Its Early Days, Bilton's Book Says

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Twitter Cofounder Evan Williams

New York Times reporter Nick Bilton has a book coming out on Twitter. 

It's excerpted today at the Times, and if there's one thing that comes through loud and clear in the book, it's that the company was an operational mess during its early years. 

This isn't unusual with tech startups, of course. Running a brand new business — inventing a new business, in Twitter's case — with little formal experience isn't pretty.

Jack Dorsey was the first CEO of Twitter. There are many examples of Dorsey being a not-great CEO, but here's one detail from Bilton: "Dorsey had also been managing expenses on his laptop and doing the math incorrectly."

Ev Williams eventually forced Dorsey out of the company and took over as CEO. Williams had previously run Blogger, which he sold to Google, so he had some operational experience. 

Unfortunately, Williams wasn't that great a CEO, either. 

While Twitter accounts, and tweets sent, grew under Williams, the company stumbled in other ways.

Essentially, Williams was indecisive and slow-moving, according to Bilton. He struggled to hire key executives like a CTO or COO. When Williams did finally hire people, it was usually his friends — not necessarily the best people for the job. 

Influential Twitter investor Fred Wilson "thought Williams had always been a terrible C.E.O.," says Bilton.

Williams was confronted on the issue at the behest of one of his investors, Bilton writes:

So [the investor] pitched the idea of bringing in, as an adviser, Bill Campbell, the famously foulmouthed former C.E.O. of Intuit and head coach of the Columbia University football team, who had mentored Jobs, Google’s Eric Schmidt and many other top executives. During their first meeting, Campbell’s message was exceedingly simple. When Williams asked, “What’s the worst thing I can do as C.E.O. to screw the company up?” Campbell responded, “Hire your friends!”

Eventually Williams was pushed out, and told he "was creating an organizational pileup" with his indecision. 

When Williams was forced out, Dick Costolo, who had been hired as COO, was made CEO. Dorsey returned to the company as a public face, a creative visionary type.  Williams remains one of Twitter's biggest shareholders.

Under Costolo, the company appears to have stabilized. Employees previously thought Twitter would burn out like MySpace. Now, they think it's going to last. 

This has interesting implications for Twitter, and, to an extent, tech investors generally. Essentially, Twitter was a complete mess in its formative years. But it was such a good idea — and despite its early problems, such a useful tool — that it survived anyway.

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Here's What Happened To Forgotten Twitter Co-Founder Noah Glass After He Was Kicked Out Of The Company

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Noah Glass

Noah Glass, the forgotten co-founder of Twitter who came up with the company's name, stands to make as much money off its IPO as Dorsey's secretary at Square (i.e. very little), according to Nick Bilton's new book, "Hatching Twitter: A True Story of Money, Power, Friendship, and Betrayal."

We already knew Glass' story was heartbreaking.

After his startup — a podcast platform called Odeo — became threatened by Apple's launch of iTunes, he and his coworker Jack Dorsey pitched the initial idea of Twitter to Ev Williams. Williams, an Odeo investor who would become a co-founder and CEO of Twitter, gave the idea the go-ahead. Glass became obsessed with the product.  

In 2011, he told us that "it was a massive labor of love" and that it took "a ton of effort and a ton of energy" to create the company. 

In his book, Bilton describes how Glass came up with Twitter's name:

Glass became obsessive, flipping through a physical dictionary, almost word by word, looking for the right name. One late afternoon, alone in his apartment, he reached over to his cellphone and turned it to silent, which caused it to vibrate. He quickly considered the name “Vibrate,” which he nixed, but it led him to the word “twitch.” He dismissed that too, but he continued through the “Tw” section of the dictionary: twist, twit, twitch, twitcher, twitchy . . . and then, there it was. He read the definition aloud. “The light chirping sound made by certain birds.” This is it, he thought. “Agitation or excitement; flutter.” Twitter.

As the idea of Twitter began to grow and take shape, a power struggle emerged between Williams and Glass. Glass felt protective of his idea and became increasingly nervous that Williams wanted him out of the company. (Business Insider previously described how Glass was the "spiritual leader" of the company.) Meanwhile, he was also struggling through a divorce.

As he grew more anxious, Glass confided his fears with his friend and co-founder Jack Dorsey. What he didn't know was that it was really Dorsey who thought that he should be fired, who had threatened to quit if Glass wasn't let go, Bilton says. 

Sure enough, Glass was ousted from the company in July of 2006 and Dorsey became CEO. Glass ended up with a small amount of cash and stock, he told Business Insider in 2011.

Soon, Bilton writes, Dorsey was erasing Glass from the company's history when he would give interviews. He would fail to give Glass credit for Twitter's name. At this point, many think of Dorsey as the face of the company. In the story of Twitter, Glass reads as a casualty of Silicon Valley's power struggles and politics.

Now that Twitter has announced its IPO, it's clear that the company will make some people incredibly rich — millionaires, or even billionaires. Dorsey, for example, will make as much as $500 million. Glass will make next to nothing. Bilton describes a chance meeting between Glass and Williams, and it's sad, to say the least:

Last month, just days before the I.P.O. news was announced, Noah Glass was walking through the Mission district. Glass, who fell into a depression after his ouster, disappeared from his former friends. Now he lives in an apartment that was built as an earthquake shack that he shares with his girlfriend, his infant daughter and his dog, Ewee. As he was walking toward Dolores Park, with his daughter strapped to his chest and Ewee in tow, he rounded a corner and bumped into his old friend Evan Williams. After a moment of initial shock, the two men, now in their early 40s, chatted amiably, recalling how they had once been next-door neighbors, then extremely close friends, then co-founders, all just a few blocks away. They politely agreed that they should meet up for coffee and went their separate ways.

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Jack Dorsey Almost Joined Facebook After He Was Fired As Twitter's CEO

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Jack Dorsey

Jack Dorsey is generally well-respected as the founder of Twitter and Square.

But he hasn't always done well-respected things, according to a New York Times adaptation from Nick Bilton's book about Twitter.

Dorsey was fired from his position as CEO of Twitter, the company he dreamed up. Bilton paints Dorsey as a distracted, inexperienced manager who was more interested in learning about fashion design than running Twitter.

But when Williams overthrew him as the company's CEO, Dorsey was hurt. 

He was so hurt, Bilton says he nearly went to Twitter's greatest competitor, Facebook. Mark Zuckerberg had been trying to buy Twitter; Dorsey personally informed Zuckerberg when he left Twitter. That led Zuckerberg to make him a job offer, but not for a specific role. Dorsey worried it might look like a demotion.

Bilton writes:

Facebook had been quietly exploring the possibility of buying the fledgling company, and while Dorsey was intrigued, Williams was not. The day after he was ousted, Dorsey called Zuckerberg to confidentially share the news. To Dorsey’s surprise, Zuckerberg asked if there was a way to prevent the firing, perhaps in order to save the deal. Dorsey assured him that there wasn’t, and Zuckerberg switched his plan from trying to buy Twitter to trying to hire Dorsey. So Dorsey met with Chris Cox, who ran Facebook’s product division, at a Philz Coffee in San Francisco. The discussions soon became more serious. But they didn’t have a specific role in mind. Zuckerberg wanted Dorsey to simply join Facebook in an unspecified capacity, and they would worry about a position later.

As he weighed Zuckerberg’s offer, Dorsey began considering the consequences...Twitter’s embarrassment might prompt a leak about what had really happened. Of greater concern was the appearance of joining Facebook without a significant job title. Would that look like a step down? “Let’s just keep talking and see if we can find the right position for me,” he told Zuckerberg. “I’ve got to think about this.” 

Read Bilton's full excerpt, here. Or buy his book, here.

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INTERVIEW: This Twitter Cofounder Will Make Almost No Money From The IPO

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Noah GlassEarly this morning, The New York Times magazine published an excerpt from a book by Times tech writer Nick Bilton. The book is called "Hatching Twitter: A True Story of Money, Power, Friendship, and Betrayal." 

The excerpt tells an incredible story.

One of the main characters is a sad figure named Noah Glass. Glass is the Twitter cofounder you've never heard of because he was booted from the company early on.

The really sad thing is that Glass isn't going to make much money from Twitter's upcoming IPO. Bilton says "Glass stands to make about as much as  [Jack] Dorsey’s secretary at Square."

Back in 2011, we managed to finally get a hold of Glass, who had not updated his Twitter, YouTube, or blog accounts in almost two years.

We've re-published our interview with him below. 

First, some background.

Glass was pushed out of Twitter in 2006. Before that he was the co-founder of a startup called Odeo. He had an investor who would become co-founder and CEO, Ev Williams.

Odeo was supposed to be a podcasting platform. But then Apple launched iTunes and everyone at Odeo panicked.

Williams told everyone: come up with something for us to do next!

Along with Jack Dorsey and a developer named Florian Webber, Glass pitched something called Twitter. Glass came up with the name. Williams liked Twitter enough to put Glass in charge. The product became Glass' obsession. He told Williams he wanted to spin it out of Odeo as its own company.

But by the summer of 2006, Williams was tired of Odeo. He bought it – and its assets, including Twitter – back from Odeo investors. He renamed the company Obvious.

Then he fired Noah Glass. (In his book excerpt, Bilton reports that Jack Dorsey asked Williams to fire Glass.)

The conversation we had with Glass touched on what it feels like to be left out of history, how hard it is to be "betrayed" by your friends, and whether Ev Williams lied to Odeo investors about Twitter's numbers. It went like this …

BUSINESS INSIDER: Tell me if I'm wrong. It seems like you are the Twitter co-founder that no one talks about. Is that it?

NOAH GLASS: Well, yeah. That's true.

I was not in the story, which in some ways was difficult to deal with in the beginning, since it was a massive labor of love and a massive labor to get it created. To create the thing, to bring it into the world. It was a ton of effort and a ton of energy.

To not be included in the story was hard to swallow at first, but when I realized what was happening to the product, this thing I helped create, the thing's not about me. The thing's about itself. Twitter is a phenomenon and a massively beneficial tool and it's incredibly useful and it helps a lot of people. I realized the story's not about me. That's okay.

BI: Tell me a little bit about the beginning of 2006 and how this thing got going.

NG: [Odeo] was in turmoil, honestly. Investors were not really happy with what was going on. Ev, who was CEO, was not really happy with the company with growth and the direction it was going. We were sort of looking for something else. We were looking for a backup plan. We had a certain amount of money and we had a team in place. We just started experimenting with stuff.

I was looking at stuff like how people were communicating on MySpace and other social networking things and seeing how people were trying to communicate and seeing how systems weren't really designed to do what people were doing with them. But people were trying to communicate in a certain kind of way. Non-synchronous. Non-realtime communication. Almost like building on the blogging idea.

Jack [Dorsey] was someone who was one of the stars of the company and I got the impression he was unhappy with what he was working on. He was doing a lot of cleanup work on Odeo. He and I had become pretty close friends and were spending time together.

He started talking to me about this idea of status and how he was really interested in status. He developed this bicycle messenger status system in the past. I was trying to figure out what it was he found compelling about it. At the same time, we were looking at 'groups' models and how groups were formed and put a couple things together to look at this idea of status and to look at this idea of grouping and it sort of hit me — the idea for this product. This thing that would be called Twitter, what it would look like. This ad hoc grouping mechanism with non-realtime status updates all based on mobile phones.

There was a moment when I was sitting with Jack and I said, "Oh, I do see how this could really come together to make something really compelling." We were sitting on Mission St. in the car in the rain. We were going out and I was dropping him off and having this conversation. There was a moment where it all fit together for me.

We went back to Odeo and put together a team. A very separate working team, mostly it was myself, Jack, and Florian [Webber], a contractor. [Florian] was working from Germany at the time. Have you talked to Florian at all?

BI: I've tried to reach him but he's difficult to reach.

NG: I haven't spoken with him in 5 years. He has his own ideas about how life works. He's an amazing guy and a major part of it also.

That's a thing I want to reiterate — you're trying to look for the full story. Some people have gotten credit, some people haven't. The reality is it was a group effort. There were lots of people putting ideas into and it couldn't have been done without this group of people. Whether or not there's individuals who get credit or don't get credit, that may be totally irrelevant. It was a collaboration. And it was almost a collaboration that came out of necessity.

In a lot of ways, we needed something. We felt a definite pressure. I felt like in two months I'd have nothing to take on. I had no idea what I was going to be doing. I was looking for something else and I wanted to keep the team together.

I put together a bare-bones team and kept it really separate and I ran it by Ev and the investors. I did all I could to keep it separate because there was lots of stuff going on with Odeo. Trying to make it better, trying to sell it. And lots of distractions. It was really difficult. Here I was inside of a sinking ship trying to launch a rocketship out of it. It was a very tumultuous, scary, and nervous time.

BI: I heard from one of Odeo's investors that you approached people at one point to say, "Hey, let me spin this thing off and start a company called Twitter." Is that true?

NG: Yeah. That's totally true. And that's probably part of the reason why I'm no longer involved with it. I felt like Odeo was crashing around me and I didn't want Twitter to be.

We had done a soft launch of it. I kept it really secret. I didn't want anyone to know what we were working on as we were setting up all the technical aspects of it.

Originally, it was all running on my laptop on my desk. An IBM Thinkpad. Using a Verizon wireless card. It was right there on my desk. I could just pick it up and take it anywhere in the world. That was a really fun time.

BI: That's when you wanted to spin Twitter off from Odeo?

NG: That was the plan — take this thing and spin it off. At that time, even in the very early stages, I had this strange feeling that I had never had before — that this was something big. I felt it from the onset. People must have thought I was a crazy person because of the way I treated it. That may have been detrimental. I really felt strongly, more strongly than I felt about anything in the past and since then — that this is something massive sitting right here in front of us. All it needs is time to grow.

I actually had done all the paperwork and was ready to roll. It was ready to go. That's not the way it worked out.

BI: I asked an investor "why did Evan end up running the company and not you?" The person basically said Ev had the money.

NG: Yeah, he had the power. Looking back, it seems to be the right thing now. It worked out, right? At the time, it didn't feel like it.

 Maybe I would have done things slightly differently and that was one of the things Ev and I had a disagreement on early on, and I told him I would do things differently.

This may be cliché to say, but when you speak truth to power, the ramifications can go a lot of different ways. Evan Williams is a powerhouse. Did you talk to him at all?

BI: I've tried to. He doesn't really want to talk.

NG:: He can talk to who he wants to now. He's the creator of Blogger, he's a massively influential person behind the blogging thing. He definitely has some amazing skills. What he did with Twitter definitely resulted in growth that was phenomenal.

I spent a lot of time early-on building a mechanism that would facilitate growth that we saw and facilitate sharing like what we see happening now. Initially, the product was growing because of the social aspect between people. The idea that police departments or fire departments are using it to give updates on the city, that was something we built into it in the very beginning as a concept. A lot of that stuff was hashed out early on.

BI: You said you felt almost immediately that Twitter could go somewhere and be powerful. When do you think Evan sort of saw that?

NG: I don't know if he sees it now, honestly. He's no longer the CEO. That's probably indicative. I think the way he works, and the way everyone works, is to validate it within your community. He saw his friends grabbing on to it early on and thought, "Oh, this is something." Whether he thought it was something big, I never really got that indication.

BI: Do you think he saw something valuable in Twitter before he bought it back from investors?

NG: Yes. Of course he did. Ev is very shrewd. He's a very shrewd businessman, and he's had a lot of practice. He's had lots of failures in the past. He's had some big failures in the past. That's his business — to isolate and spot value where it is.

There's a difference between between fanatical — and I hate to say that I was fanatical — but to be extremely passionate like I am or being very super rational and calculated like he is. Evan and I are two different polar opposites. I am very passionate about certain things and I will get passionate about certain things I believe in. I'll speak passionately and I'll wave my arms and I'll jump up and down and I'll use energy to prove my point or create momentum around an idea. Whereas he'll sit down, think about it, write it down, walk away. He'll write a paper on it, come back and say, "This is my opinion." He's very calculated.

BI: Do you feel like he slow-played Odeo's investors in any way? Let me read you something he sent to the investors. This is September 2006.

"By the way, Twitter, which you may have read about, is one of the pieces of value that I see in Odeo, but it's much too early to tell what's there. Almost two months after launch, Twitter has less than 5,000 registered users. I will continue to invest in Twitter, but it's hard to say it justifies the investment venture Odeo certainly holds, especially since we're in a different market altogether."

He's downplaying Twitter in that letter. Do you think he was really that pessimistic about its chances?

NG: I don't think I want to comment on that. You understand why? You understand the potential implication of what you're saying?

BI: I do.

NG: Of course you do. I don't know.

BI: I think it's important to explore that issue.

NG: You can. Go ahead. I don't know what that would mean for me. Can I ask something, Nicholas?

BI: Yes.

NG: You feel as though — you've spoken to investors who have some sort of unease about this thing?

BI: Here's what I've encountered amongst Odeo investors.

There are angel investors who were just sort of friends of Ev's and maybe Ariel Poler and friends of George Zachary who just put money in, and they all feel sort of dumb. They all feel like, "Oh, my bad. I didn't press hard enough to find out what the Twitter thing was."

Other ones feel philosophical about it and wish Ev had been a little more forthcoming.

And then one or two will ask a question: "Did Evan see numbers that showed people were very engaged with this product in a way that he hid and did he recap the company in order to seize a product he saw would be valuable? Did he? I don't know."

That's what they'll say.

NG: In some ways I definitely feel that there is something to your story. To that angle of the story.

[But] I have to tell you that Ev wasn't happy for a long time. He wasn't happy with the structure before Twitter even happened. He was unhappy with the structure of Odeo. He was unhappy with the relationships with investors.

Think about it — he had the money. He had the power. They didn't really do anything. In the board meeting we would basically tell them what was happening. They'd say yes, no, offer whatever tidbits of advice. He didn't feel as though he needed that structure anymore. He didn't want it. He was trying to find ways to get out of it for a while. For a few months, six months before.

Quite honestly, he didn't want to be CEO of Twitter. I wanted to be CEO of Twitter.  In a lot of ways, he never wanted to be there. The whole time.

In that letter he sent to the investors, he's not lying. He didn't lie about anything. He said, "This is what I'm doing. I'm going to invest in it." Which is a pretty big statement. Whether or not he felt it was going to be a massive thing, he felt it was going to be something.

I think he wanted to set up an incubator company at the time. Obvious was supposed to be something different than what it is today. Obvious was supposed to be this umbrella company where they had multiple projects. Like an incubator. And he stopped until Twitter became one of those things. 

It wasn't something where he saw it was going to be massive and needed to devalue everything.

BI: So Ev didn't intentionally downplay Odeo's assets when he bought the company back from his investors?

NG: Without getting inside of his head, you'll never know. There are a lot of different ways of looking at it too. He was a nice guy. Was he doing anyone a favor? Was he really doing favors? Hard to say. Was it a calculated move? Definitely. Was there lots of thought put into it? Definitely. He definitely made a lot of money. That was a phenomenal investment. He got a great deal.

BI: When Ev stepped down from the CEO position last Fall, The New York Times did a big story on him. They had this one quote in the story, not a quote of his, but one of those weird things when they say someone says something. They say, "Mr. Williams says that all successful businesspeople make enemies along the way."

NG: That's true. Ev had lots of enemies at Blogger before we even started Odeo. A lot of them come from necessity. They come from ego too, of course. He had to shut down the company. At Blogger he had to let everybody go. Then they got bought by Google, and that doesn't make anyone happy. The people he had to let go right before this massive thing happens.

BI: Were there signs in the summer of 2006 that Twitter, even if it was small, that engagement was strong?

NG: It was highly, highly compelling. Highly engaging. I'd been testing, doing the shortcode, writing up the description of what it was. It had to be approved by our gateway provider for our shortcode. I don't know how many users we had at the time, but it was relatively small. The people who run the SMS gateway were like, "This thing is the best thing I've seen. The best thing I've seen using SMS in this way." They were doing thousands of different SMS applications at the time.

There were definitely indicators. It was super compelling, super engaging. Anyone who was using it at the time realized it was something different, something special.

I pitched it at a board meeting. One of the very last board meetings, I think. I don't know if the other guys got it. They kind of got it. But I don't know if they fully got it. They saw it as a distraction.

Unless you sort of beat them over the head with it, they were never going to see the value in it. They saw it as a distraction from what they had invested in. They had invested in Odeo, and here I was telling them this thing is great, this is where we should be going. They'd say, "What about Odeo?"

 BI: The other day I listened to Biz give an interview on Howard Stern, and Howard Stern asked how Twitter was founded. The answer he gave made me say, "That's not reality at all." Unless 13 or whatever people I've talked to ... What do you think when you hear that stuff? How do you deal with it?

NG: I try not to listen. Honestly. For the past few years. I try not to listen. I moved to Los Angeles two years ago just to get away from it, to get away from the noise. Because I couldn't move on.

There was a time I approached them. I approached Jack and Ev and said, "I want to be included in the story. I want some credit." I looked at emails and some documentation and said, "These things should be acknowledged. I should be acknowledged as a co-creator."

I have mixed emotions, of course.

In one way, the story is not told. I think even Oprah asked [Biz] where the name came from, and I came up with the name. I spent a bunch of time thinking about it, what name worked, and that became the name.

There's a creation myth that everyone tells. Everyone is the hero of their own creation myth because they were there. They were in the limelight. They got to tell the creation story.

There's truth in their story, of course. There's some truth in every story.

I didn't create Twitter on my own. It came out of conversations. I do know that without me, Twitter wouldn't exist. In a huge way. But the same is true without Jack. And to some degree it's true without Ev. Ev was involved.

BI: What about Biz?

NG: Biz was involved more than Ev. Ev wasn't involved at all for the creation and launching of it. He'd come in and we'd talk occasionally. I think during a lot of the time he was working on the idea of buying back Odeo. I was working on Twitter, and very intensely.

Biz got a lot of credit after writing a document describing what we were working on. He was working on a lot of other things too. I asked if he would write it because I needed the documentation for the lawyer. I needed something for the lawyer in order to describe the company I wanted to create around Twitter. He wrote the document for me and got a lot of credit, but I told him to write it and what to write. Have you met Biz? Have you talked to Biz?

 Biz is a good guy.

 Biz is energetic and enthusiastic about stuff. That's why he's in all the media. That's why he does what he does. He's a personality.

BI: Did you walk away with equity in Obvious? How did that work out?

NG: I didn't walk away with anything initially. At a later time I received a certain amount of equity in Twitter. Am I okay? I don't really want to comment on whether I'm okay or how well I did. I came away with something. If I stayed, if it would have gone the other way, I would have come away with a lot lot more. I didn't come away with zero. I received a small amount of cash during the buyback. A very small amount for my involvement and shareholdings in Odeo. Everyone else got payback first.

BI: What happened after you left Odeo? How did you feel?

NG: I'm sure you get this impression from the story and I've never really said this before — I did feel betrayed. I felt betrayed by my friends, by my company, by these people around me I trusted and that I had worked hard to create something with.

Afterwards, I was a little shell-shocked. I was like, "Wait ... what's the value in building these relationships if this is the result?"

So I spent a lot of time by myself. And working on things alone. 

I worked on a game for a while. It didn't really come out the way I wanted it to. 

I moved to Los Angeles to work on something totally different. It was an alternative energy system that I had in mind. I built a prototype for that. It just didn't function the way I thought it was going to function.

I've been working on projects that could be something big if they get fleshed out.

Moving back to San Francisco is sort of a step in being involved in collaboration again. It's something I didn't necessarily want to do because of what had transpired. Because of the story you're writing. Collaboration on something where everyone else gets all the credit and all the glory and fame is frustrating. It can be a frustrating experience.

BI: That's an understatement.

NG: To say the very least about that, right?

It kind of turned me off from collaboration for a while which is something I really enjoyed. Being back in San Francisco, it's a very collaborative city. I walk my dog to the park now and I'm talking about some cool application with some random person. It has a cool energy to it that I haven't felt in a while.

It feels good. I'm back here. Right now I'm looking around, sort of looking outside of myself now. Looking at other ideas, other things. Seeing if I can help other people work on things. Seeing what the post-Twitter environment looks like now.

BI: What do you think of Twitter right now?

NG: I feel like Twitter has something at its core that's valuable. It's relatively obvious to those who use it, those who experience it.

It needs to grow. It's needed to grow a lot. I think they tried a lot of things in the past few years that weren't necessarily the right things. I think its real potential still hasn't been revealed yet.

It needs someone who's not just mesmerized by its sparkliness, but can see it as a product. Who can look at how people are actually using it and how people want to use it.

Whoever's there now needs to reinvestigate the product: how it's being used, and what its core functionality is. Because there are still people out there who don't get it. How can something be so popular and widely discussed and visible, and yet people aren't understanding it? It's not overly complicated. It's not. It's super-simple. That's the thing that someone needs to address. Those core concerns.

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13 Bizarre Things We Learned About Twitter's Jack Dorsey From His Big New Profile In The New Yorker

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jack dorsey selfie

The New Yorker has written a great, long profile of Twitter founder Jack Dorsey. (And it's a huge counterpoint to Nick Bilton's book on Twitter, which makes Dorsey look like a backstabber.)

The New Yorker story, by D.T. Max, contains these bizarre details, which we've quoted in indented text:

1. His skin once turned orange:

Formerly a vegan—too much beta-carotene turned his skin orange—he is now on the Paleo diet, which forbids refined sugar and grains.

2. He rides the bus to work every day:

A ride costs two dollars, but Dorsey has a monthly pass, so the actual price, he told me on a recent commute, is closer to a dollar seventy-five. “If you buy it in bulk, it saves you a little bit of money,” he explained.

3. He never reads real books:

When people give him books, he says, he gives them away, then downloads the e-book, which he usually deletes from his iPad after he’s finished.

4. He eats at the same restaurants every week:

He has a weekly restaurant schedule: “Zuni on Tuesday, Aziza on Monday, 54 Mint on Wednesday. Thursday, Tiburon. Friday, I don’t go anywhere.”

5. He is a semi-reluctant billionaire:

According to Forbes, Dorsey is America’s sixth-youngest billionaire. Seven years ago, he was in debt. He seems somewhat discomfited by this turn: he likes money but dislikes himself for liking it. At one point, he commented, “One of my ex-girlfriends said to me, ‘Money is round. It’s made to roll.’ I definitely took that in.” He quickly added, “It really weighs on me. I definitely feel the most fundamental issue is economic equality.”

6. He once had dreadlocks that were blue and orange:

At the end of 1999, [he] moved to San Francisco and started a Web-based dispatch firm. (Dorsey withdrew from N.Y.U. a semester short of graduating.) Dorsey took on the look of a bike messenger, with dyed dreadlocks that ranged from bright blue to peroxide orange.

7. He's a failed massage therapist:

He hoped to open a chair-massage service for programmers, in San Francisco. He imagined having a place that “gave programmers code therapy and massage therapy.” (He promises that he was serious.) But when he went back to San Francisco, in 2005, he discovered that “everyone was a massage therapist,” and dropped the idea.

8. He once got a nose ring:

“That really hurt,” he says. “That was a mistake.”

9. He once rewrote the online ticketing program for the Alcatraz ferry:

He searched ads on Craigslist and found an opportunity: the ticketing program for the tourist ferry to Alcatraz needed a revision. The system was beset by fraud, and Dorsey wrote a more secure program.

10. He once hired two anarchists to work at Twitter:

Dorsey remembers the two anarchist programmers refusing to sit during sit-down meetings and refusing to stand during the standup ones.

11. He once stole some money from New York mayor Mike Bloomberg. He used the mayor's credit card to demonstrate Square before people realized that money would be deducted from their accounts:

... he pulled the same trick on Mayor Michael Bloomberg, who demanded the money back.

12. Facebook CEO Mark Zuckerberg used to cook him dinner:

For a time, Zuckerberg and Dorsey met regularly for dinner. When they got together, Zuckerberg cooked. During the meal, they warily conversed about technological trends. Dorsey says, “He’d ask me if I had any ideas. Am I seeing anything in video? And, immediately, I’d turn back the question: ‘What are you guys seeing?’ ”

13. He thinks about chucking the whole thing in and disappearing from the tech world:

“I’m at a point in my life when I want to go deeper,” he said. “I could just move down to Marfa and become an artist.”

SEE ALSO: Jack Dorsey's Reputation Is Crushed In Nick Bilton's Book On The Early Days Of Twitter

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JACK DORSEY: Did I Want To 'Screw' My Twitter Co-Founder Ev Williams? 'I Don’t Know. Maybe.'

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Jack Dorsey

The reputation of Twitter co-founder Jack Dorsey took a big hit when New York Times reporter Nick Bilton published an excerpt from his forthcoming book on the founding of Twitter. 

In the excerpt, Dorsey was portrayed as a vindictive, narcissistic dilettante, who took much too much credit for the founding of Twitter.

Dorsey has responded to the excerpt from Bilton with his own take on his early days at Twitter, via a long New Yorker profile. The most interesting bit in the 11-page profile comes when Dorsey is asked if he was behind the ouster of Ev Williams at Twitter. 

In case you're unfamiliar with the story, Dorsey was the first CEO of Twitter. He had never run a company, and struggled to learn the ropes. He would frustrate coworkers and investors by failing to deliver a vision for Twitter, and by knocking out of work early to attend fashion, yoga, and drawing classes, according to Bilton. 

Eventually, Williams pushed Dorsey out of the company, taking on the role of CEO for himself. Dorsey, in Bilton's telling, was very hurt by Williams, and over time planted seeds of doubt about Williams and pushed him out of the CEO slot. 

Dorsey was asked if he worked to get Williams forced out of the CEO role. He tries to downplay his power, but he admits there's something to the idea that he wasn't fond of Williams. 

Here's the New Yorker:

He was deeply hurt. He says of Williams, “He didn’t want to be C.E.O., and then he did.” Williams insists that he prefers starting companies to running them, and that he took action only because Dorsey was in over his head. In his view, Dorsey simply wasn’t ready to be a C.E.O. Neither was Williams, it turned out—in 2011, he was removed by Twitter’s board. Williams’s allies believe that Dorsey engineered his ouster. Biz Stone says, “They think he worked on the board for two years, like the Count of Monte Cristo, to get his revenge.” Dorsey insists that he was not the cause. When he left the C.E.O. job, he ceded his voting rights to Williams. “I didn’t have that much control,” Dorsey says. “He was the largest shareholder.” But Dorsey acknowledges that he may have been working to turn the tables. “I was chairman,” he says. “Many people were coming to me. I would say, ‘You should bring that up with the board, not just to me.’ ” He adds, “Was I thinking, Screw Ev? Emotionally, was I asking that? I don’t know. Maybe.” After Dick Costolo, a Twitter executive, was promoted to C.E.O., Dorsey resumed an active role at the company.

Note that Dorsey says, "Was I thinking, Screw Ev? Emotionally, was I asking that? I don’t know. Maybe."

That's not a denial by any stretch. At the same time, so what? This only makes Dorsey human.

There's no denying Twitter was, at least in part, his idea. He was pushed out of the company, which really hurt. 

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Square Has A Super-Cool New Way To Send Cash To People Using Just An Email's Subject Line

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If you have a debit card, you can now send cash to anyone at any time simply by sending an email.

That's the premise of Square Cash, which launched yesterday, for any debit card holder with an email address. Square is the mobile payments company from Jack Dorsey, c0-founder of Twitter. 

Here's how Square Cash works:

If you want to send money, compose an email to the recipient, type the amount you want to pay in the subject line, and cc cash@square.com:

Cash 1

 If this is your first time using the service, you will receive an email from Square directing you to the Square Cash website, where you will be prompted to enter your debit card number. 

The idea of money changing hands by changing phones instead is hardly a new idea. Services like PayPal and Venmo have made it simply to link up debit cards to apps and websites so that payment processes become more streamlined. 

So what is it about Square Cash that makes it better? Moving money takes only one step: enter your debit card number. Services like PayPal require you to enter your checking account number and your routing number. Plus, you have to visit its website or download its app. 

If you do want a Square Cash app on your phone, it's available in the Google Play Store for Android devices and Apple's App Store.

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CONTROLLING CHAOS: Twitter's Wild Ride From Doodle To IPO

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Twitter Cover new

In the fall of 2010, Twitter was in chaos.

The micro-blogging site, which had been founded four years earlier, still wasn't generating much revenue despite having 145 million users. The site was still crashing constantly. The staff were at each other's throats.

Chaos, moreover, was not an unfamiliar state for Twitter to be in.

Twitter's first CEO, Jack Dorsey, had taken the company from idea to reality, but then made a mess of the place before getting fired. Twitter's current CEO, Evan "Ev" Williams, had overseen huge user growth but was now moving too slowly and indecisively.

Twitter's board decided it now had to fire Williams, too. But who would take over?

A former stand-up comic and entrepreneur named Dick Costolo was one possibility. He was Twitter's COO. But Costolo had never run a large company before, so he hardly seemed the guy to finally get the chaos under control.

The largest company Costolo had managed, in fact, was the one he had founded, Feedburner. A content syndication service, Feedburner had had fewer than 100 employees when Google acquired it in 2007. Twitter already had more than 300. Also, Costolo was 47. In Silicon Valley, that's old. Famous founders like Mark Zuckerberg and Drew Houston were half Costolo's age and more accomplished.

At wits end, the Twitter board reviewed its options.

It could make Costolo an interim CEO until it found someone more established. Twitter had worked frequently with an executive recruiter, Paul Daversa, to unearth talent, and the board had a few more serious-seeming candidates in mind.

Or the board could take a chance on Costolo, who had risen to the occasion once before. The Twitter COO job had been a leap for Costolo, and he had excelled at it. Costolo also already knew the company's inner workings, and he had the respect of Twitter's management team, partially because he had helped hire most of them. Fred Wilson, a Feedburner investor and partner in Union Square Ventures, and one of Twitter's board members, trusted him. 

Dick Costolo

In typical chaotic Twitter fashion, the choice was ultimately made by the man who was getting sacked.

In addition to being Twitter's CEO, Evan Williams was its largest shareholder. Williams and Costolo had known each other for more than a decade, having been introduced by a mutual friend in the mid-1990's, Eric Lunt. To soften the blow of his ousting, Twitter's board told Williams he could be part of the CEO search process. Initially, Williams wasn't thrilled with the idea of Costolo taking his place. But he came around and eventually pushed for Costolo to permanently take his job. 

On October 4 2010, Williams resigned as Twitter's CEO. Costolo took over.

With Twitter set to go public at a $15+ billion valuation next month, the company's success seems as though it has always been smooth sailing.

In fact, it has been anything but.

The whole Twitter story, for example, even starts with an argument: Who is really responsible for the company's success?

Does the credit belong to Jack Dorsey, who came up with the original idea? Does it belong to Evan Williams, who backed the concept and then took over as CEO?  Should it go to Dick Costolo, who turned Twitter into a real business? Or do Twitter's investors or other lesser-known heroes deserve the nod?

The truth is that, more than any other rocketship Silicon Valley startup in memory, Twitter's success has been a product of collaboration, not one genius visionary. At different times in its history, different people have provided the leadership, vision, and skills that the company needed. 

But this group collaboration has been the farthest thing from pretty.

When Costolo was handed Twitter three years ago, the company was a mess. Its four-year history was bloodied with founder feuds, failed products, office politics, and executive turnover. 

"The act of getting from there to here," Benchmark Capital's Peter Fenton says, "was violent."

Why was Twitter's early history so chaotic? And how did it finally get the place under control?

Over the years, we've reported many episodes in the Twitter story. Recent interviews with a number of sources, as well as reporting by other tech journalists, have helped us fill in some gaps.

So here is the wild ride of this year's mega tech IPO...

Part 1_Twitter_Chapter

People close to Twitter during its first five years describe the company as "chaotic,""stressful," an "absolute mess" and "a zoo."

That's because founders establish a company's culture. And Twitter's founders fought a lot.

They fought about what the company's product should be. They fought about who should run it. And, right from the beginning, they even fought about who had created it.

The Twitter founding story most people know includes three people: Jack Dorsey, Christopher "Biz" Stone, and Evan Williams.

It goes something like this:

Odeo Ev Williams Noah Glass Biz Stone

Biz Stone and Evan Williams had worked together at Google, after Williams sold a company called Blogger to Google. The pair then started a company called Odeo, a podcasting company that soon ran aground. Jack Dorsey, one of Odeo's employees, came up with the idea for Twitter. Stone and Dorsey made the prototype, and Evan Williams then built a company around it.

That's the story Stone told Howard Stern in a 2011 interview and that Dorsey has since repeated. But it's a lot different than the story Williams told on the day Twitter launched publicly in 2006.

"[Twttr is] a 20% project, if you will, that we—esp. Noah, Jack, and Florian—have been working on on the side for a couple months,"Williams wrote in July 2006. "It has nothing to do with audio or podcasting [like Odeo did], but we think it's kinda neat."

Who are Noah and Florian?

According to early Twitter employees, they're the company's forgotten founders. Particularly Noah Glass, who started Odeo in his apartment before he ever even met Evan Williams.

Glass and Williams had met four years before Twitter was founded, in 2002. They were neighbors in San Francisco's Noe Valley. Glass had recognized the Blogger logo on Williams' computer and later spotted Williams in a magazine as the blogging site's founder. That's when Glass mustered up the courage to introduce himself.

Kevin Systrom Noah Glass

"He was working on this wacky idea he later pitched me, which let people call a phone number, record a message, and then publish it to the web (via Blogger) by pressing a button,"Williams wrote of his first meeting with Glass.

That "wacky idea" became Odeo, a podcasting startup. And Odeo eventually morphed into Twitter.

At first, Williams was an investor and advisor to Odeo, not a founder. Then he took on a more active role, acquired co-founder status, and became the company's CEO. 

Technically, Christopher "Biz" Stone was an Odeo co-founder, too. But he came into the picture later. 

Eventually Odeo moved from Glass' apartment to Williams' apartment. Williams had used some of the money he got from selling Blogger to buy a house. His old apartment was a perfect headquarters for the startup. 

In those days, Glass was Odeo's leader, not Williams. "I think [Odeo] was something Ev was interested in, but it was mostly Noah's thing," says former Odeo employee Ray McClure. Other early Odeo employees included Evan "Rabble" Henshaw-Plath and his wife Gabba. "Mostly it was the four of us working out of the apartment," McClure said.

jack dorsey youngSoon, Odeo moved into a true office and started hiring more employees. One was a quiet, on-again, off-again web designer named Jack Dorsey, who had ruffled hair and a nose ring. Another was an engineer named Blaine Cook. 

Odeo also had an intern named Kevin Systrom, who would later go on to found Instagram. Systrom sat next to Dorsey and talked a lot about photos.

By June 2005, Odeo had a functioning podcasting product. But when it launched, people were skeptical of its potential.

"We apologize if the following profile lacks our usual excitement and enthusiasm,"TechCrunch founder Michael Arrington wrote while profiling Odeo in 2005. "We just have a funny feeling that iTunes 4.9 is going to have a somewhat substantial impact on the podcasting portal market."

Arrington was right. Apple came out with an iTunes podcasting platform that it built into its iPods — and it then went on to sell 200 million of the devices. Also, Odeo employees found that they weren't even using their own product. "We built [Odeo], we tested it a lot, but we never used it," engineer Blaine Cook recalls.

In fall of 2005, Odeo investor George Zachary of Charles River Ventures says, the "shit hit the fan."

By that time, Odeo had 14 full-time employees. Biz Stone was one of them.

Williams and Glass still had money in the bank from the $5 million the company had raised. But the pair knew they either needed to shut down or pivot to a new idea. They told Odeo's employees to start coming up with new startup ideas that Odeo could try. "Hackathons"— entire days or nights dedicated to coding new products —became regular occurrences. Some employees broke off into groups.  

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Odeo co-founder Noah Glass gravitated toward Jack Dorsey, who Glass says was "one of the stars of the company." 

Dorsey had an idea for a completely different product, "Stat.us." Stat.us would show people what their friends were doing at any given time.

The quiet designer had sketched out the idea for Stat.us on a piece of notebook paper years before joining Odeo. Now, he shared this idea with his Odeo co-workers over Mexican food on a playground near Odeo's office, South Park in San Francisco. 

At first, Glass wasn't impressed. "He started talking to me about this idea of Stat.us," Glass recalls. "I was trying to figure out what it was he found compelling about it."

Suddenly, the brilliance of Stat.us struck Glass.

"We were sitting on Mission Street in the car in the rain," he says. "We were going out and I was dropping [Dorsey] off and having this conversation. It all fit together for me."

In February 2006, Glass, Dorsey, and a German contract-developer named Florian Weber presented Dorsey's idea to the rest of the company. Glass changed the name from "Stat.us" to "Twttr." With Twttr, a user could text a message to a phone number, and the message would be broadcast to all of the user's friends.

Text messages are limited to 160 characters. But each Twttr user needed a user name or handle attached to the message. To make room, each Twttr text was eventually limited to 140 characters. 

Glass pushed for Odeo to drop other side projects and pursue Twitter. For that reason, other Odeo employees considered him Twitter's "spiritual leader." Williams green-lighted the project and put Glass in charge.

"In terms of our new projects, I feel most strongly about Twitter," Williams wrote Odeo executives in an email, excluding Dorsey. Williams was often indecisive and relied heavily on his gut when making decisions, as he did in this case. "We could have a lot more discussion, and I may change my mind, but I think I just need to make a call at this point, and my gut is pulling me to Twitter."

sketch twitter bizDorsey was still just an Odeo engineer then, but he held an important role in the development of Twitter. He and Florian Weber coded the service while Stone worked on designs. Glass worked on product development and came up with hallmark Twitter features such as time stamps on tweets.

At one point, the entire early Twitter service was running on Glass's laptop, an IBM Thinkpad, and a Verizon wireless card. "It was right there on my desk," says Glass. "I could just pick [up Twitter] and take it anywhere in the world. That was a really fun time."

Glass and Dorsey were more captivated by Twitter than anyone else at Odeo.

"There were two people who were really excited [about Twitter,]" says Odeo investor George Zachary. "Jack and Noah Glass. Noah was fanatically excited about Twitter. Fanatically! Evan and Biz weren't at that level. Not remotely."

Glass was excited about Twitter because of its ability to connect people in real time. In 2006, Glass especially craved emotional connections; his marriage was on the rocks.

"You know what's awesome about this thing?" Zachary remembers Glass saying. "It makes you feel like you're right with that person. It's a whole emotional impact. You feel like you're connected with that person."

His emotional investment in Twitter made it difficult for Glass to deal with what was about to happen.

young jack dorsey nose ringBy March of 2006, Odeo had a working Twttr prototype. In July, TechCrunchcovered Twttr for the first time. This time, Odeo's employees were actually using the product.

Odeo employees became obsessed with Twitter. In those days, Twitter messages were sent by SMS, a texting service that phone companies charged for. Odeo employees racked up SMS bills that totaled hundreds of dollars a month.  The company agreed to pay their bills.

That August, a small earthquake shook San Francisco, and word about it quickly spread through Twitter. That was an early 'ah-ha!' moment for Twitter users and company-watchers alike. By that fall, Twitter had thousands of users.

That's when Odeo engineer Blaine Cook began to feel that there were "two companies" at Odeo – the one "Noah and Florian and Jack and Biz were working on" (Twitter) and the one everyone else was working on, Odeo.

Twitter, says Odeo employee Ray McClure, "was definitely the thing you wanted to be working on." 

Not everyone saw Twitter's promise. At an Odeo board meeting that summer, Noah Glass presented Twitter to the directors. He and Stone even made a video about "Twttr 101." The board hardly blinked at it.

The Smartest Stock Buyback In History

The board's lack of enthusiasm for Twitter, in fact, soon helped Williams make the most lucrative business decision of his life. 

In September 2006, a couple of months after Twitter launched, Williams wrote a letter to Odeo's investors. In it, Williams told them Odeo was going nowhere and that he felt bad about that. He felt so bad, he said, that he wanted to buy back their shares so they wouldn't take a loss.

In this letter to Odeo's investors, Williams wrote briefly about Twitter.

By the way, Twitter (http://twitter.com), which you may have read about, is one of the pieces of value that I see in Odeo, but it's much too early to tell what's there. Almost two months after launch, Twitter has less than 5,000 registered users. I will continue to invest in Twitter, but it's hard to say it justifies the venture investment Odeo certainly holds -- especially since that investment was for a different market altogether.

Williams proposed buying back Odeo investors' stock with his own money. Eventually, the investors agreed. Multiple investors, who combined had put $5 million into Odeo, say that Williams made them whole.

In other words, all of Odeo's assets — including Twitter — were sold to Evan Williams for approximately $5 million. That's why Williams is the largest shareholder of Twitter today, owning 12% of the company.

By comparison, Jack Dorsey now owns less than 5% of Twitter. It's not clear how much of Twitter Biz Stone or Noah Glass own. They either sold their shares, or their percentages are so trivial that they're not mentioned in Twitter's financial filings.

One big question Odeo investors still have is this:

Did Williams have an inkling of how valuable Twitter might become when he offered to buy back Odeo? Was the buyback offer a Machiavellian ploy? Or did Williams really just feel bad about the failure of Odeo's original idea and want to make his investors whole?

"Could Evan have known this would be the world's best thing ever and hid it while re-capitalizing the company?" one investor asks. "If there's ever any litigious stuff in the air it will be: How much did Evan know about the user engagement and numbers of Twitter at the time of buying it out?"

Those are fair questions. Williams knew that some Twitter's early users were highly engaged because he was paying monthly SMS text bills — as high as $400 — for his employees. Glass remembers mobile carriers telling him they'd never seen so much SMS activity before Twitter.

"You're going to want to bump up to the unlimited txting [sic] plan," Williams had written when he announced Twitter on his blog in July 2006. 

Most Odeo investors, with the benefit of hindsight, echo the sentiments of James Hong, the cofounder of HotOrNot.com and an Odeo angel investor.

"Obviously, I wish what happened hadn't happened," Hong says. "There was a dark period where I didn't want to hear about Twitter."

There was a dark period where I didn't want to hear about Twitter.

Another investor agrees. "I wish he had reached out to me," says Mitch Kapor, still an active and successful investor in the Valley. "I think he could have, but he didn't. And I'd say it's sort of a shared responsibility."

One reason people feel comfortable bringing up questions about Williams' motives is because the Twitter co-founder has a reputation for being shrewd. He was described by many Odeo investors and employees as "calculating." And he had taken some flak for his behavior at his earlier company, Blogger: His co-founder, Meg Hourihan, told The New York Times' Clair Cain Miller after the Google buyout, “I don’t think [Williams] took care of the people who got him to where he was." The Times also quoted Williams as saying that "all successful businesspeople make enemies along the way."

One early Odeo employee thinks Williams knew exactly what he was doing:

"Ev decided there was something interesting enough in Twitter that he wanted to buy all the assets and buy everyone out," he says. 

Another employee, however, gives Williams the benefit of the doubt.

Blaine CookOdeo engineer Blaine Cook recalls a meeting during the summer of 2006, a couple of months before the buyback, about whether or not to shut down Twitter. Cook says it wasn't obvious that Twitter would a big hit until six months later, in the spring of 2007, when it captivated the South By Southwest Interactive conference in Austin, Texas.

Also, a few months after buying Odeo back from its investors, Williams offered to let a select few buy into Twitter at a $25 million valuation, including Charles River Ventures, Silicon Valley angel-investing godfather Ron Conway, and Conway's SV Angel fund.

Tim O'Reilly, an Odeo investor who once employed Williams and runs O'Reilly Media, reflects: "It's certainly possible that Ev is more Machiavellian than he appears. I don't know. I take it at face value that he was doing what he thought was best. It's very easy to look back and say, 'Wow, I'd like to have a bigger piece of that.' It's very easy to say that."

playground twitter san franciscoIn any event, by the fall of 2006, Williams had successfully purchased Odeo's assets back from investors. He promptly changed the company's name to Obvious Corp.

Williams had also concluded that one key Odeo employee wouldn't be part of the new company: Odeo founder Noah Glass.

On July 26, 2006, shortly after Glass presented Twitter to Odeo's board, Williams had asked Glass to go on a walk. The pair wandered over to South Park, where Dorsey had first mentioned the idea for Twitter that spring.

There, on a bench, Williams fired Glass.

Glass was stunned.

Williams offered Glass six months of severance while his Odeo stock continued to vest, according to a comprehensive new book by Nick Bilton of the New York Times. If Glass didn't accept the offer, Williams said, he would be publicly fired.

Glass took two weeks off and then told fellow employees he'd be leaving. Everyone seemed shocked.

"I remember when Noah told me he wasn't going to back to Twitter," says former colleague Ray McClure. "[It was] hard to hear him say that. It kind of blew my mind because I felt like we all identified with this, and of course I was worried about the team."

It was heartbreaking to see someone who cared so much about Twitter forced to sever ties with his product. 

"Noah got really into it," says early Odeo employee Rabble Henshaw-Plath. "Seriously obsessive. I-don't-care-if-my-marriage-dies-I'm-focused-on-this into it." 

So why did Williams fire Glass?

One reason may be their clashing personalities. Glass is loud, and Williams is quiet.

"Noah, you can always hear him talking," says McClure. "Ev, you can always hear him thinking."

crystal taylor early twitter odeo employeeOne Odeo employee speculates that Williams fired Glass because Glass could get too emotional. After all, he was dealing with a failing company paired with a failing marriage. The employee remembers a time when Glass was "a little hard" on girl named Crystal Taylor, who remained at Twitter for a long time and ran its customer service division. "I think it was a day that he was kind of stressed. He was a little volatile."

Glass felt his firing was the result of a power struggle. Glass thinks he might have expressed too much interest in running Twitter for Williams' liking. Early on, before Williams or Stone were believers in Twitter, Glass wanted to split the product off as its own company and become CEO.

"I actually had done all the paperwork and was ready to roll," says Glass. "[Twitter as a stand-alone company] was ready to go. That's probably part of the reason why I'm no longer involved with it...I told [Williams] I would do things differently. When you speak truth to power, the ramifications can go a lot of different ways."

When you speak truth to power, the ramifications can go a lot of different ways.

Another reason for Glass' firing may have been because another Odeo employee — an employee Glass thought was his friend — wanted him out.

According to Bilton's book, Hatching Twitter: A True Story of Money, Power, Friendship and Betrayal, Jack Dorsey met with Williams a few weeks before Glass was fired and told Williams he'd leave if Glass wasn't canned. 

At first, Glass walked away with no Twitter shares. Later he was given some, although the amount he'll make when Twitter goes public is hardly life-changing.

Florian Weber, the other early employee who never received much credit for Twitter's founding, got even less. In 2005, Weber was hired by Williams and Odeo as a contractor, not a full-time employee. To this day, he owns no Twitter stock.

"It’s not something that I pushed terribly hard for,"Weber recently told The New York Times' Nick Bilton and Vindu Goel.  Weber says he has no regrets and that he's happy with his life.

dom sagolla twitterNor were Glass and Weber the only Odeo employees who missed out on the Twitter bonanza. Dom Sagolla, Odeo's Head of Quality, was fired by Williams in May 2006. He, like Weber, never received Twitter stock. "To see it come to life and have it taken away, I was devastated," Sagolla told Bilton and Roel. Early Odeo employee Rabble also left Williams' company that spring. Odeo's head of business development, Adam Rugel, departed that summer. Its VP of Product, Tim Roberts, was gone by fall.

For Glass, being ousted from Twitter has been hard to stomach.

"I felt betrayed by my friends, by my company, by these people around me I trusted and that I had worked hard to create something with," Glass says. "I was a little shell-shocked. I was like, 'Wait...what's the value in building these relationships if this is the result?' So I spent a lot of time by myself. And working on things alone."

It's important to note that while Williams may have fired Glass, he has mentioned Glass' involvement in Twitter multipletimes since letting his former friend go. 

"Some people have gotten credit, some people haven't. The reality is it was a group effort," says Glass. "I didn't create Twitter on my own. It came out of conversations. I do know that without me, Twitter wouldn't exist. In a huge way."

When news of Twitter's impending IPO broke in September, Glass crafted a message on the network he founded for the first time in months.

noah glass twitter

His Twitter bio still reads: "I started this." Another early Odeo employee agrees, "He did."

Part 2_Twitter_Chapter

In October 2006, after Williams bought back Odeo's assets, he announced Obvious Corp to the world. He said Obvious was a new company fully funded by him, and that he alone owned Odeo's assets, including Twitter.com. 

"I believe there is a lot of value in what we've built—both Odeo and Twitter—but I did not believe the [old] structure was going to lead to the kind of success we wanted," Williams wrote then. "In the new company, with a new structure, and a new model, I think they are great investments."

By early 2007, Twitter began to take off. Williams says rapid growth kicked off around January 2007 after Twitter opened its application programming interface (API) to the world.

twitter sxsw 2007 jack dorsey evan williams biz stone jasonOther companies soon built apps like Twitterific and TwitterVision, which displayed tweets in new, interesting ways, and these boosted Twitter's numbers. Twitter's users doubled and tripled month over month. Twitter also began to take off in Japan, where usage soon rivaled U.S. usage. Chinese micro-blogging site Sina Weibo soon copied and began to compete with Twitter in Asia.

In March 2007, Twitter won a prize for best startup at the South by Southwest conference. Twitter received so much attention there that its site crashed for two days.

One month later, Twitter had become big enough to become its own company. It spun out of Obvious Corp and Jack Dorsey, who was then 30, was named CEO.

"Ev called Jack a 'genius' but the word we use more often in the office is 'mastermind,'"Biz Stone wrote when the news was announced.

These days, Dorsey is widely praised for founding Twitter and another highly successful company called Square. Now 36, Dorsey has already accomplished so much that he's occasionally compared to Steve Jobs. But in April 2006, when he became Twitter's CEO, Dorsey wasn't yet well known. He was also inexperienced, and leading Twitter proved difficult for him. It wasn't long before his relationship with Williams began to sour. 

Jack Dorsey business card twitter

In the summer of 2007, an earthquake shook Mexico City. Seven people there gave updates on Twitter. Their messages spread before the U.S. Geological Survey reported the earthquake, and an hour before CNN caught wind of it. By then, it had become clear that Twitter was no longer just a tool for telling friends where you were at all times. It was a fast way for news to spread, from people who were experiencing events in real time.

That summer, Twitter closed its first round of funding at a ~ $25 million valuation. Some of Odeo's investors were invited to participate. New faces, such as Netscape and Andreessen Horowitz founder Marc Andreessen, also joined the group.

One of these new faces would prove to be particularly important.

Williams reached out to an old friend, Dick Costolo, about investing in Twitter. The paid had been introduced a few years back, and Costolo had just sold Feedburner to Google. Williams asked Costolo via email if he would consider investing either $25,000 or $100,000 in Twitter.

It only took three minutes for Costolo to reply, according to the New York Times's Bilton and Roel. 

"I'm on the $25,000 bus," Costolo replied. "Thanks Ev, this will be a lot of fun."

With its fresh infusion of cash, Twitter's growth continued to soar. Users were getting more creative with their tweets and crafting more of them. In August 2007, the hashtag was used for the first time. By March 2008, Twitter reached 1.3 million users. That May, it closed another round of financing, this time $15 million, from top investors like Union Square Ventures, Jeff Bezos, Spark Capital, and others.

As Twitter's public profile grew, however, its foundation began to crumble.

Twitter under Jack Dorsey's leadership, sources say, was chaos.

"Jack is crazy-smart and a product visionary and all that," says one source. "But Jack wasn't ready to be CEO at that time."

Twitter downtime 2007

Dorsey struggled with the transition from engineer to boss. He wasn't leading teams well, and employees weren't happy working for him. He wasn't hiring new people fast enough. The site constantly crashed, making the Twitter "fail whale," which appeared when the site went down, a more prominent mascot than Twitter's blue birds. In 2007, the year Dorsey became CEO, Twitter's total downtime was six days. The constant crashing was a source of stress.

"Jack's role was that of a founder and a heavy influencer at the board level," one source says. "But he is not operational...he's not broadly effective."

"Jack is very smart, but he is not a leader," says another. "He can inspire investors more than employees." 

Dorsey's interest in and facility with the financial side of the business left much to be desired. Dorsey, according to Nick Bilton's book Hatching Twitter, made mathematical errors while keeping track of Twitter's expenses. He set up partnerships with texting companies but SMS fees were so high, Twitter was spending nearly 6-figures per month.

Dorsey had also not yet focused entirely on Twitter: He wanted to be a fashion-designer, and he'd often leave work to take night classes. He also left early for art and yoga classes. His extracurriculars eventually became such a distraction, Bilton reported, that Williams eventually sat down with Dorsey and said, "You can either be a dressmaker or the CEO of Twitter. But you can't be both."

Sometime during 2008, Williams got fed up. He  decided that he should be — and would be — the CEO of Twitter.

Williams had more money than Dorsey and three or four times as much Twitter stock. As Twitter's majority shareholder, when Williams made a decision, it was final. The Twitter board agreed that Dorsey wasn't working out, and they backed the decision to remove Dorsey.

When Williams came after Dorsey's position in the fall of 2008, it was an ugly "violent exchange," a source says. 

Jack Dorsey and Evan Williams"Jack wanted to be CEO, but it wasn't really the right call," this person said. "It was very clear Ev wanted to be CEO and it was pretty clear to people in the company that Ev was a better choice."

Unlike Dorsey, Williams was a proven entrepreneur. "Ev had more credibility than Jack," says the source. "He wanted the job. He got the job. That's why their relationship is a little touchy...He made it happen."

Publicly, Williams lay Dorsey's firing at the board's feet. And, ultimately, the board may have done the dirty work. Two of its members, Bijan Sabet and Fred Wilson, took Dorsey out to breakfast and delivered the blow, Bilton reports. They told Dorsey he'd receive $200,000 severance and become a silent chairman; Williams would be Twitter's new CEO.

On October 16 2008, the news was made public. "While the board of directors and the company have nothing but praise for where Jack has taken us, we also agree that the best way forward is for Jack to step into the role Chairman, and for me to become CEO," Williams wrote then.

facebook jack dorseyDorsey knew who had sacked him. For the next four years, Dorsey and Williams barely talked. Dorsey nearly joined Twitter's greatest competitor, Facebook, out of spite. Dorsey later told Vanity Fair's David Kirkpatrick his ousting felt like "being punched in the stomach." 

"Twitter held all my desires in the world,"he said.

Dorsey learned a common startup lesson the hard way: Coming up with an idea doesn't mean you own the business. 

"I let myself be in a weird position because it always felt like [Evan Williams’s] company," Dorsey later said. "He funded it. He was the chairman. And I was this new guy who was a programmer, who had a good idea. I would not be strong in my convictions, basically, because he was the older, wiser one.”

One year later, in 2009, Dorsey founded another company, Square, with a new group of investors. It was a startup no one would be able to rip away from him. So far, it has been a phenomenal success.

Part 3_Twitter_Chapter

Dorsey's distracted management style left Twitter in a bind internally. But, externally, the startup's profile was skyrocketing.

Dorsey had been what the company needed to get off the ground. When he became Twitter's CEO, the company only had a few thousand users. When Williams took over a year and a half later, that number exceeded 1 million, and millions of tweets were being sent per day.

Still, Twitter's next three years, from mid-2008 until mid-2011, were "crazy intense," a source says.

"The website was going down all the time while usage was going up. The valuation kept going up, and pressure kept going up," this person said. "It was never calm. Ever."

Evan Williams

By his own admission, Williams made a lot of mistakes as CEO. "I’ve screwed up in many, many, many ways in terms of managing people and product decisions and business," he told the New York Times' Claire Cain Miller in 2010. But, more importantly, Williams oversaw spectacular user growth and kept the company headed in the right direction.

Williams had trouble making decisions, which frustrated his board and fellow executives. When it came to hiring, he moved slowly and preferred to pull in family and friends, who weren't always the best candidates. 

Plus, the same growth problems that had plagued Dorsey also plagued Williams. While Twitter's site crashed less frequently under Williams, it was still an uncomfortably common occurrence. 

Williams could have made all his Twitter problems go away quickly by selling the company. And he could have made a fortune doing it. 

In the fall of 2008, Facebook came after Twitter. Facebook offered to buy Twitter for $500 million in a cash and stock deal. Twitter's previous round of financing had valued it at $98 million, so the offer was tempting. Williams alone would have made hundreds of millions of dollars.

Facebook and Twitter spent a few weeks discussing the deal. Facebook, although it initiated the talks, didn't love everything about Twitter. Twitter wasn't generating much revenue, and its SMS fees alone could have cost Facebook up to $75 million annually, AllThingsD's Kara Swisher reported then.

131_picture 1Twitter, meanwhile, didn't like that Facebook's offer valued Facebook stock at a seemingly inflated valuation of $15 billion. Facebook was worth closer to $5 billion then, Twitter thought, and a $150 million buyout offer wasn't very appealing.

Twitter's team asked for a final night to sleep on the offer. When Twitter's board woke up, there was a page-long email from Williams in each member's inbox.

In the letter, Williams asked his board when it's the "right" time to sell a company. He then expressed why he didn't want to sell Twitter. Williams didn't need to convince his board. The email was more of a courtesy since Williams still owned a controlling stake in the company.

"He would have made hundreds of millions," says a source. "He could have said, 'This is Zuckerberg's problem now.' But he was a huge believer in the company."

Williams' decision not to sell Twitter to Facebook for $500 million was one of many smart decisions he made as Twitter's CEO. 

Under Williams, Twitter began making strategic acquisitions. A Twitter search company called Summize was Twitter's first and arguably most important acquisition, because it helped solve Twitter's "fail whale" problem. The Summize deal was finalized under Dorsey's CEO term, but Williams led the project.

jack dorsey signs summize acquisition"[Summize] was really important for Twitter for a whole bunch of reasons," a source says. "Twitter needed the technical capability to make the site work, and the Summize guys were instrumental. Their search engine was great, but the team [practically] saved Twitter."

Twitter's hyper-growth continued under Williams, in part because it began to be adopted by celebrities. Oprah Winfrey signed up for Twitter and received more than 100,000 followers within 24 hours. Ashton Kutcher signed up for the service in 2009 and encouraged other Hollywood stars to follow. Also, Twitter broke its first true news story.

On January 16, 2009, a US Airways jet made an emergency landing on the Hudson River. No one was killed, but all the passengers had to climb out of the plane and wait on its wings to be rescued. A Twitter user snapped a photo of the passengers and it spread quickly online. Soon, mainstream media picked up the Hudson plane crash story. Every outlet credited Twitter with breaking the news.

Hudson River plane crash US Airways SullyThat was the moment that the ousted Jack Dorsey says he realized Twitter's massive potential. Twitter was more than the "what I'm doing" status updates that Dorsey had initially envisioned. It was the fastest way for important news to spread.

Williams also persuaded Twitter's executive team that the company needed to create its own mobile apps. Until 2010, Twitter had relied on third-party developers to develop excellent tools for Twitter. But Williams believed staying on that course would create too much brand confusion. And, eventually, Twitter itself would become irrelevant and die.

On April 10, 2010, at Twitter's first-ever "Chirp" conference, Williams announced the acquisition of the first of many application companies. Twitter bought the parent company of an app called "Tweetie," AteBits. At the time, Tweetie was the number one Twitter app in Apple's App Store.

Williams also radically expanded the size of Twitter's staff. He grew the team from 20 people under Dorsey to 300 by late 2010. He made subtle product innovations, too, like perfecting the retweet process, introducing a Twitter url shortener and fixing how @ reply messages worked.

dick costolo twitterAnd he persuaded a small Twitter investor, his friend Dick Costolo, to join Twitter full-time.

By the fall of 2009, Dick Costolo was already a Twitter board member. Earlier when Twitter had been hunting for an independant board member, Costolo came to mind. He was a Twitter investor and a friend of Williams. He was also a former CEO the board already knew well.

Costolo took the board seat and began working closely with Williams. Everyone liked what he brought to the table and wanted more of Costolo, not less. Williams decided to change the nature of his meetings with Costolo. At a party in 2009, Williams offered Costolo the Chief Operating Officer position. Costolo accepted.

When Costolo joined Twitter full-time, he was one of the only business people on staff. There were only about 30 people at the company then. 

Costolo set up the structure for Twitter's finance and sales divisions. He ran business development, began driving international strategy, and put an early ad strategy together.

By mid-2010, Twitter's traffic had grown to 160 million users. Instrumental executives like Ali Rowghani and Adam Bain had joined, Rowghani as CFO and Bain as the creatively titled "President of Revenue."

As the company grew, Williams seemed less and less interested in running Twitter. Gone were Twitter's startup days. In their place were piles of paperwork, HR headaches and performance reviews. The board and other Twitter executives noticed Williams' lack of enthusiasm. It also noticed the great job Costolo was doing as Twitter's COO.

It isn't clear if Williams agreed to resign, or if the board forced him out. The truth is probably somewhere in the middle. Regardless, according to Nick Bilton of The New York Times, Twitter advisor and honorary board member Bill Campbell sat down with Williams in 2010 and told him the board wanted to replace him as CEO with Dick Costolo. Costolo may not have been comfortable replacing the man who had brought him to Twitter. But eventually, with Williams' blessing, he took the job as interim CEO. Williams nudged the board to make the position permanent. 

On October 4, 2010 Costolo was officially named Twitter's third CEO. 

Everyone hoped the third CEO would be the charm. 

Part 4_Twitter_Chapter

People who know Costolo describe him as a "funny,""directed,""self-possessed guy" who "manages to be likable without alienating people."

He had to be someone with a positive outlook to wade through the muck that was Twitter.

"Dick certainly describes [his early days as Twitter's CEO] as a mess," a friend of Costolo's says.

The mess lasted well into 2011.

Costolo's first big mission was to clean up Twitter's board. It had somehow become full of uninvited bystanders, and too many Twitter stories were getting leaked to the press. 

Dick Costolo tweet becoming ceo crash

Twitter's actual board members then consisted of Spark Capital's Bijan Sabet, Union Square Ventures' Fred Wilson, Benchmark Capital's Peter Fenton, Williams, Dorsey, and Costolo. But these were not the only people who attended the board meetings.

"There were lots of observers and people dialing in," one source said. Kleiner Perkins' partner John Doerr, for example, floated around. Representatives from IVP and other institutions popped by, too. Executives at Twitter who had never been appointed to the board felt entitled to pull up chairs.

"There was a moment when the people in the board room became so many it was silly," one person said. "It was almost like crashing the board meeting with these people coming to the party. You had the IT guy coming to the board meetings. You had John Doerr who wasn't even an observer coming, I guess because billionaires can do whatever they want. Bill Campbell, who was an advisor, [was also] coming to the board meetings."

john doerr tbi

The messy board may have personally affected Costolo too. A report from Bilton's book Hatching Twitter suggests that in September 2010, when Costolo was still COO, honorary board member Bill Campbell nearly fired him in a fit of frustration. A source who has spoken with both Campbell and Costolo, however, says that never happened.

One by one, Costolo tracked the unofficial board members down and asked them not to come back. No one is quite sure how Costolo did this. All they know is that the offenders never showed up again. 

As Costolo was cleaning up the board, two of Twitter's long-standing board members volunteered to step down. Spark Capital and Union Square Ventures each owned large portions of Twitter. These positions made their portfolios lopsided, and they were eager to sell some shares. But Fred Wilson and Bijan Sabet, the two board members, worried that selling shares while remaining board members would send mixed messages. 

Dick Costolo

Costolo agreed and these two investors dropped off the board. Each sold a minority portion of their Twitter stock to Rizvi Traverse, a firm that quietly amassed the largest outside stake in Twitter — more than 15%. Evan Williams reportedly sold shares to Rizvi Traverse, too. Union Square Ventures and Spark Capital are the next largest outside shareholders. Each firm has more than the 6.7% stake owned by Benchmark Capital.

After Wilson and Sabet dropped off the board, seven true members remained: Costolo, Jack Dorsey, Evan Williams, Benchmark's Peter Fenton, Flipboard CEO Mike McCue, former DoubleClick executive David Rosenblatt, and Peter Currie of Currie Capital. McCue later left Twitter's board later when Flipboard became a conflict of interest.

With the board cleaned up, Costolo could begin running a tighter ship. But internally, the company was still in shambles. One person who was at Twitter during the Williams-Costolo transitional years describes that era as "a shitshow." "There were so many politics," this person said. "Like, a funny amount. I guess it was the culture."

Many executives were fired that year. Others quit. Twitter's VP of Engineering Mike Abott left in October 2011. VP of Product Satya Patel left in June 2012. 

At Google and Facebook, some antics occur at the senior level. At Twitter, bickering trickled down to middle managers who tried to claw their ways ahead.

"If you look at Google, the same people have been running it [for 15 years]," the source said. "Once you see the top [people fighting] then people next to you start getting fired, you try to get leadership and [secure] your position. You do stuff you normally wouldn't [do]."

There would be a big road map meeting one day, this person says, then the people in that meeting would never be seen again.

Mike Abbott"We were like wait, where did they go?!" the source recalls. "I had never seen so many senior people get fired in such a short period of time."

There also wasn't a lot of trust among colleagues at Twitter. "A lot of people at Twitter told you what you wanted to hear," this person said. "Then thirty minutes later they'd be in a different meeting saying something different to someone else... [Some of the managers] tried to be okay with anything, but that's not a leader. The best leaders tell the same stories to everyone because [if you don't], you turn people against each other."

Some of Twitter's turnover and confusing culture problems were caused by growing pains.

"Startups are all messy inside," one person says of Twitter's tough years. "During those years, Twitter grew to hundreds of millions in revenue...I don't know how you go through that kind of growth in the public eye without it being crazy. It's like going through your teenage years and not being mad at your parents every once in a while. That's not dysfunctional, that's normal."

Slowly but surely, Costolo and a few of the executives he hired sucked the poison out of the company. 

Even more impressively, they found a way for Twitter to start generating real revenue. 

Part 5_Twitter_Chapter

 In April 2010, with the help of CFO Ali Rowghani, Twitter launched its first paid product: Promoted tweets. Advertising Age was the first sponsor. 

Promoted Tweets show a sponsor's message to targeted users outside the sponsor's follower lists. Promoted Accounts, a second product, are used by brands or individuals who want to obtain more followers. A third product, Promoted Trends, stick a sponsored hashtag among other trending topics on Twitter. Promoted Tweets are now Twitter's most popular product.

Rowghani had worked with Steve Jobs at Pixar, and some of that management style rubbed of on him. He is widely respected at Twitter.

"Ali was my favorite," says a former employee who asked not to be named. "He was no bullshit. No politics. He would tell you what he thinks. He's very, very smart in the way he understands people and technology. And he knew how to grow the company from 200 to 2,000 people. He had good instincts. "

Ali RowghaniSources describe Rowghani as quiet but not overly introverted. He is "laser focused"– "a massive adult." In meetings, he "sucks your brain," asking probing questions and retaining all the useful information presented.

Rowghani is said to be the perfect complement to CEO Dick Costolo.

While Costolo, a quick decision-maker, can be "frenetic," Rowghani is "more deliberative and reflective." 

They are a good team, one source says, because Costolo "needs to be out in the world glad-handing, and he feels he can do it because he trusts Rowghani to manage home base."

On December 19, 2012, Costolo made Rowghani Twitter's COO. Since then, Rowghani has developed Twitter's relationship with Apple (Apple now builds Twitter directly into its iPad and iPhone operating systems), and pushed Twitter into TV.

adam bain ignitionWhen TV shows are heavily discussed on Twitter, it often causes other Twitter users to tune in and watch. Brands spend a huge pile of cash on TV ads, so this insight is helping Twitter win some of that business. Earlier this year, Rowghani helped Twitter acquire BlueFin Labs, a social TV analytics company.

Like Rowghani, Adam Bain, the leader of Twitter's sales force, has excelled. 

"The two key intellectual thought partners in terms of strategy [at Twitter] are Ali and Adam," says a source. "Adam runs the sales part. Adam is an effective leader of that group and they've done really well."

Bain's team performed so well last year that he maxed out his commission package and was listed the third highest-paid employee at Twitter. 

Under Rowghani, Bain, and Costolo, Twitter's revenue has grown like this:

  • 2009: $0
  • 2010: $28 million
  • 2011: $106 million
  • 2012: $317 million
  • 2013: $600+ million (estimated)

Two other people have helped Costolo excel as Twitter's CEO: Frenemy founders Jack Dorsey and Evan Williams.

While his tenure as Twitter's CEO wasn't perfect, Williams' work set Costolo up for success.

"Dick did a masterful job [as CEO] 50% because he's awesome and 50% because Ev did a fantastic job picking up all the pieces from Jack," says one source. "I think people have forgotten how critical Ev was. When he took over the company [from Dorsey] it wasn't a company. It was a product that was crashing. He did all these things that were critical to the company."

Dorsey, who briefly returned to an active role in Twitter in 2011, has found a way to help Costolo, too. He has become invaluable when it comes to spotting must-have technology and talent for Twitter. 

Instagram team visiting Facebook"Dorsey is so good at what he's good at it's almost uncanny," said one person who knows Dorsey's work at Twitter.

For example, in April 2012, Dorsey led a hard push for Twitter to acquire Instagram.

Kevin Systrom, Instagram's co-founder, had worked with Dorsey and Williams as their intern at Odeo. Dorsey always supported Systrom. He personally invested in Instagram. 

In 2012, at an Allen & Co. conference in Arizona, Dorsey and Ali Rowghani spent a lot of time schmoozing with Systrom. The three of them sat around a fire at the Ritz Carlton resort at Dove Mountain, where Rowghani and Dorsey made Systrom an acquisition offer, Kara Swisher reported for Vanity Fair. Twitter, they told Systrom, would be willing to buy Instagram for about $500 million in an all-stock deal.

This was a massive offer, given that Instagram was only a year and a half old. But Systrom had other options. Facebook CEO Mark Zuckerberg was also courting him. And Systrom wanted to run Instagram independently. Instagram soon accepted a $50 million investment from Sequoia Capital. 

Facebook's Mark Zuckerberg, unlike Twitter, didn't take no for an answer. He spent a weekend convincing Systrom to reconsider — and he succeeded. Ultimately, Facebook acquired Instagram in a $736.5 million deal, $300 million of which was delivered in cash.

dom hoffman

The missed opportunity was a blow to Twitter and Dorsey. Dorsey's instincts about Instagram had been right. The failure to win the deal motivated him to try harder on the next one.

A few months after Facebook bought Instagram, in the summer of 2012, Dorsey set his sights on a new startup, Vine.

Vine was a video app that hadn't launched yet. It was built by three New Yorkers, Rus Yusupov, Dom Hofmann and Colin Kroll. People who saw the early prototype fell in love with it.

"Everyone on the app knew this thing was special," a Vine investor says. "It was such an awesome product. It wasn't even fully built and yet it was still special."

Investors could hardly contain their excitement. One, in fact, did not contain it.

SV Angel's David Lee, who is an investor in Dorsey's other company, Square, showed Dorsey the video app over dinner in California. 

Dorsey instantly felt Twitter needed to own Vine.

After that first sighting, things moved quickly. Dorsey flew to New York and told Vine's founders they had to join Twitter.

When Vine's founders met Dorsey, they felt he was smart but intimidating.

Dorsey calmed their nerves. He told them Twitter wouldn't re-brand or shut down Vine. Instead, Vine would be part of Twitter's long-term vision. Dorsey also made the founders an offer few first-time founders could refuse. 

Twitter offered to acquire Vine in a deal valued at tens of millions of dollars. It was a great deal for Vine's founders, who would all be joining the company and getting a lot of stock. It wasn't a great offer for Vine's investors, who wanted to see the app through to launch.

One source says Twitter offered Vine a cash and stock deal "magnitudes" higher than $10 million. Another confirms the buyout offer was higher than $10 million but less than $100 million — again, not bad for first-time founders and a startup that had yet to launch.

Some Vine investors tried to fight the acquisition. There was talk of making a counter-offer in a new round of funding that would have let Vine's founders personally pocket millions. But this time, Dorsey won. Vine's founders took Twitter's offer. Hofmann is now Twitter's General Manager of Vine. Kroll is the app's CTO. Yusupov is Vine's Creative Director.

Today, Vine has more than 40 million users and Twitter has added to the Vine team in New York. 

"The brilliance was that Jack immediately recognized how important [Vine] could be and how good the team was," a source with knowledge of the deal says. "Jack met with [Vine], recognized immediately that Twitter needed to get the thing done, and Dick made it happen. They worked well together on that." 

Part 6_Twitter_Chapter

 Over the past year and a half, the drama has died down at Twitter. Jack Dorsey and Evan Williams are even speaking to each other again. The pair broke bread over dinner at a Moroccan restaurant in San Francisco, Aziza, last May. 

This year, Twitter has been aligned around one common goal: going public. But as people familiar with the company readily admit, Twitter still has a lot to prove.

Twitter will generate more than $500 million this year, but the company is not yet profitable. It lost $69 million on $254 million revenue during the first half of 2013. 

twitter founders

Also, Twitter is struggling to attract more mainstream users. In the second quarter, its growth in the United States slowed to just 1 million new unique users. Even with its 250 million total active accounts, Twitter is one-quarter the size of Facebook.

Some Twitter shareholders worry what will happen once the company goes public.  

"Twitter has tried a lot of things that have really failed miserably," one person says. "All they have [working] is the original [140-character] concept. Twitter hasn't innovated in the way you would expect a tech company to."

Twitter is a simple product, and for that reason it's also easy for competitors to duplicate, although the network effect that goes with Twitter's massive user base is hard to build from scratch. Instagram came out of nowhere and threatened Facebook. The same could happen to Twitter.

"One thing no one talks about is it can all go away," a Twitter shareholder who asked not to be named says. "All it takes is one company doing something a little bit better. Twitter doesn't do anything that incredible that a new startup can not do better, and if that happens, then its $15 billion valuation becomes worth much less very quickly."

But if anything, Twitter's rocky road to success proves the company is relentless. 

graham

Paul Graham, the founder of high profile startup accelerator Y Combinator, often says startups should be more like cockroaches. Ugly and tough. In many ways, that's Twitter.

"Apparently the most likely animals to be left alive after a nuclear war are cockroaches, because they're so hard to kill,"Graham wrote in April 2007. "That's what you want to be as a startup, initially. Instead of a beautiful but fragile flower that needs to have its stem in a plastic tube to support itself, better to be small, ugly, and indestructible."

Some shareholders think Twitter's best days are still before it. Lately, instead of founder feuds, Twitters has become known as the ultimate source for breaking news. Twitter is where the world first learned of Whitney Houston's death, for example, as well as Osama Bin Laden's death and the Boston Marathon bombings

Saudi billionaire Price Alwaleed and his investment arm, Kingdom Holding, invested $300 million in Twitter in 2011. Alwaleed doesn't plan to sell a single share when Twitter goes public.

"We believe that it is just beginning to touch the surface," Alwaleed recently told Reuters. "We will be selling zero, nothing, at the IPO."

Twitter's tumultuous story and ultimate success has been a true collaboration for which no one person can take credit. Dorsey's passion for real-time updates ignited Twitter. Glass ran with the idea and pushed Williams to pursue it. Williams funded the company when it needed a cash infusion, saw Twitter's importance went far beyond a vanity tool, and accelerated growth. Costolo cleaned up the company internally and monetized the already-blockbuster product.

Most impressively, Dorsey and Williams were each forced out as CEOs. But despite wounded pride and bitterness, they still returned to make Twitter better. 

Bijan Sabet of Spark, who's been a part of Twitter's bumpy ride since 2008, is understandably thrilled with the outcome.

"For me personally," he tells NYT, "this is a once-in-a-decade or once-in-a-career kind of investment."

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Boom! From Twitter Alone, Jack Dorsey Is A Billionaire

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Jack Dorsey

When Twitter stated its $26 price per share yesterday, co-founder Jack Dorsey was expected to make a lot of money. 

He'd have made north of $600 million at that price, but he wouldn't have been a billionaire from Twitter alone.

Now, Twitter is trading at $45.

So Jack Dorsey and his 23,411,350 shares are now worth about $1.05 billion. If Square, his other company, goes public next year, his billionaire status will be solidified.

UPDATE: As Forbes correctly points out, Dorsey has technically been a billionaire since 2012 between his involvement in both Square and Twitter. That would require him to sell his Square stock on a secondary market though. Now, from Twitter alone, he's reached billionaire status.

Congrats!

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See The Advice Mark Zuckerberg, Jack Dorsey, And 8 Other Tech Founders Gave To A Class Of Entrepreneurs

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Mark Zuckerberg

On Oct. 19, 2013, thousands of programmers, engineers, and designers joined a lineup of amazing speakers for Y Combinator's Startup School 2013.

The list of speakers included industry heavyweights like Facebook's Mark Zuckerberg, Twitter and Square's Jack Dorsey, and venture capitalist Chris Dixon, among others.

Gregory Koberger attended each of their presentations and put together a set of wonderful, illustrated notes using the Paper app for the iPad. He graciously provided high-quality versions of his notes for the benefit of Business Insider readers.



Phil Libin - Evernote



Dan Siroker - Optimizely



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11 Of Twitter Co-Founder Jack Dorsey's Favorite Things You Can Buy Online

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Jack Dorsey

It's not often that we get to see the exact products that the rich and famous are into.

That's why it's pretty neat to see Jack Dorsey's page showing his favorite products on Square Market, his payment startup's online store.

The items reveal quite a bit about his taste. All of his favorite goods are high-quality, simple, and practical (more or less) — with one $5,500 exception.

We really like this artistic map of St. Louis, Dorsey's hometown. ($30)

Click here to see it on Square Market >>



When Dorsey looks at this simplified map of Moscow's transit system, he sees: "A city, and an octopus." ($28)

Click here to see it on Square Market >>



Why does Jack Dorsey need a fancy whiskey knife? "For just about everything." ($68)

Click here to see it on Square Market >>



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Square Is Talking To Investors About A New Round At $5 Billion Valuation – But What About IPO Plans?

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twitter jack dorsey on floor of nyse

Jack Dorsey's payments startup Square is talking to investors about raising a new round of financing at a $5 billion valuationJessica Lessin and Eric Newcomer of The Information report.

Lessin and Newcomer say the company would use the money to buy stock from some of its employees.

The news may signal a change in plans for Square.

In November, The Wall Street Journal's Douglas MacMillan reported that Square was talking with Goldman Sachs and Morgan Stanley about a 2014 IPO. 

MacMillan said Square's 2014 revenues could approach $1 billion, up from $550 million this year. 

It's possible that Square could do a final late stage round in the next couple months and an IPO in 2014.

But again, Lessin and Newcomer say the point of the $5 billion round would be to allow insiders to sell their stock.

Why would insiders want to do that instead of waiting for an IPO?

They wouldn't – unless they think there's a chance Square might IPO at a valuation less than $5 billion.

So what's going on? 

Don't know! But let's speculate.

Maybe Dorsey suddenly doesn't feel like Square is ready for an IPO.

Maybe Dorsey took a look at taking Square public and decided no thanks. 

The only reason for a company to go public is to get employees and investors liquidity and to have liquid stock to use for acquisitions.

Otherwise, being public is a big pain. You have to spend a lot of your time kissing-up to big shareholders who control your fate – shareholders who have your number on speed-dial.

 

This $5 billion round would take of liquidity for Square. And maybe Dorsey doesn't feel like Square has any big acquisitions ahead of it. So why go public ever?

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Jack Dorsey Gives Employees 10% Of His Square Stock — Worth Over $150 Million

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Twitter founder Jack Dorsey

Square founder and CEO Jack Dorsey has returned 10% of his stock to the company, reports Fortune.

Dorsey previously owned 30% of the company, and gave back 3% of his own volition.

Depending on the current estimates of the company's valuation, this frees up some $150 million of stock.

As Fortune explains, the move will not only help out existing employees eligible for further equity in the company, but will also help out new hires who will be able to get more stock options.

Given the relatively generous nature of the news, it's only fitting that Dorsey made the announcement at the Square holiday party last weekend.

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Twitter Cofounder Jack Dorsey Is Joining Disney's Board (DIS)

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Twitter cofounder Jack Dorsey Jack Dorsey is joining the board of Disney. 

Dorsey is one of the cofounders of Twitter, and the company's chairman.

He's also the CEO of Square, a mobile payments company. 

Disney CEO Bob Iger is on the board of Apple, so he's no stranger to tech. Iger was friends with Steve Jobs, who was on Apple's board. 

After Disney announced Dorsey's appointment, Dorsey tweeted the following:

Here's the official release...

BURBANK, Calif.--(BUSINESS WIRE)--The Walt Disney Company (NYSE: DIS) Board of Directors has elected Jack Dorsey, chairman of Twitter Inc. and CEO of Square Inc., as an independent director, effective immediately.“I am honored and humbled to join the Disney Board”

“Jack Dorsey is a talented entrepreneur who has helped create groundbreaking new businesses in the social media and commerce spaces,” said Robert A. Iger, Disney’s chairman and chief executive officer. “The perspective he brings to Disney and its Board is extremely valuable, given our strategic priorities, which include utilizing the latest technologies and platforms to reach more people and to enhance the relationship we have with our customers.”

“I am honored and humbled to join the Disney Board,” Mr. Dorsey said. “Disney is a timeless company, one we all grow up learning from and admiring.”

Mr. Dorsey is the co-founder of Twitter, the social networking and microblogging service that allows users to create and share ideas and information instantly via messages of 140 characters or less. Mr. Dorsey posted the world’s first Tweet--“just setting up my twttr”—on March 21, 2006, and since then Twitter has grown to include more than 230 million monthly active users worldwide who create about 500 million Tweets every day. Prior to becoming Twitter’s chairman in 2008, Mr. Dorsey was president and chief executive officer.

Mr. Dorsey is also chief executive officer of Square, a commerce company he co-founded in 2009. Headquartered in San Francisco, Square provides innovative products and services for local businesses including a mobile credit card reader, an iPad point-of-sale system, an online marketplace, and a wallet application that allows consumers to make payments using their mobile devices.

Mr. Dorsey attended New York University and Missouri University of Science and Technology.

Mr. Dorsey will stand for election along with the company’s other directors at the annual meeting on March 18, 2014. Pursuant to the tenure policy in the company’s corporate governance guidelines that limits board service to 15 years, Judith L. Estrin will not be standing for re-election.

“Judy has served Disney shareholders incredibly well during her 15 years of service, and we will miss having her on the Board,” Mr. Iger said. “Her insight and advice on technological innovation and our business, as well as her passion for excellence, have been invaluable to me.” Ms. Estrin, who has co-founded eight technology companies and served as chief technology officer and senior vice president of Cisco Systems Inc., is chief executive officer of JLABS, LLC, a privately held company focused on furthering innovation in business, government and nonprofit organizations.


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Jack Dorsey Thinks Checkout Receipts Are The Next New 'Publishing Medium'

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jack dorseyJack Dorsey spoke at the National Retail Federation expo in New York, sharing his visions for a future in which cash register reciepts are a medium for publishing.

Yes, we're talking about those little slips of paper you get handed at the checkout.

BuzzFeed stopped by the expo and caught a little of Dorsey's speech:

"What if we see the receipt more as a publishing medium — a product unto itself that people actually want to take home, that they want to engage with, be fully interactive with?" Dorsey asked a room of people at the Javits Center today during the National Retail Federation's annual expo.

"What can we do with this everyday tool?" he said. "What can we build into this canvas that's actually valuable, that's independent of the product you just sold? What can you give in this communication channel, this publishing medium, that people want to engage with?

[...]

Another way retailers could better use receipts is by adding their Twitter handle to them, he said.

via Valleywag

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A Washington University Professor Is Suing Square And Claiming He Is A Co-Founder

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jack dorsey

A Washington University professor is suing mobile payments startup Square for fraud and patent infringement, claiming that he should be included as one of the company's co-founders, the St. Louis Post-Dispatch reports

Square, founded by Twitter's Jack Dorsey and a former owner of a glass-blowing business, Jim McKelvey, makes a credit card-swiping attachment for cell phones and tablets.

The legal battle over the patent on that card reader is tangled and has been going on for several years. 

McKelvey told the Post-Dispatch last year that he thought up the idea for the card reader in 2009 and contacted his friend Dorsey to help develop it. He then contacted Prof. Richard Morley, who holds patents on several card-reading technologies, to help develop a prototype. 

In December 2010, Square and its co-founders filed a lawsuit against Morley's company, REM Holdings 3, claiming that McKelvey was wrongly left off a new patent for the developed card reader device. Counterclaims followed and encompassed several patents. That lawsuit is still pending. 

The new suit Morley filed Thursday against Square however, says that Morley alone invented the card reader and the magnetic stripe decoding algorithms on Square's app. Morley's attorney also said that that Morley helped the company on the business side by explaining the way credit cards are processed. 

"Mr. Dorsey and Mr. McKelvey conspired with the objective of owning the lion's share of the company and excluding Dr. Morley from receiving his share as a co-founder," the lawsuit alleges. Essentially, Morley is claiming that he was ousted.

The accusation is unfortunate because Dorsey was previously accused of helping oust alleged co-founder Noah Glass from Twitter during that company's early years.

Amid speculation of an IPO later this year, Square responded with plans to vigorously fight the lawsuit. 

Morley is seeking an unspecified amount of damages. 

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10 Twitter Accounts Every Entrepreneur Should Be Following

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jack dorsey 9:13

Looking for the latest in tech? Or perhaps some inspiration to get your day jump-started? With the start of a new year comes a great opportunity to do some spring cleaning and clean up the clutter. What better way to simplify life than getting your words of wisdom in 140 characters?

If you’re new to Twitter or just looking to freshen your feed up a bit this year, here are 10 people you should be following:

James Altucher

Author and blogger — @jaltucher

Blunt honesty and great motivation are served up daily from James Altucher. He offers up practical ways to live what he calls, “the daily practice” of developing a well-balanced life as an entrepreneur. With a slew of book titles to his name and successful investment companies under his belt, Altucher has a refreshing banter of brutal honesty about his own insecurities and struggles. It’s great to see a success story that can be honest about all the failures that led him here.

Jack Dorsey

Co-founder of Twitter and founder of Square — @Jack

Aspiring entrepreneurs today have access to mentors like never before with the prevalence of social media. And who better to follow than the co-founder of Twitter? Dorsey's micro-blogging platform offers you the opportunity to hear from him daily and even send or ask questions. He may not have the bandwidth to answer, but you have a chance to connect with an incredibly successful entrepreneur who keeps innovating. That’s priceless.

Tim Ferriss

Author, TV Host and lifestyle expert — @Tferriss

Ferriss is a compulsive tweeter and shares the kind of cool insights you’d expect from the lifestyle-design guru who brought you "The 4-Hour Workweek." There is plenty here to keep you motivated and catch the fire that seems constantly lit under Ferriss. With travel, tech and inspirational tweets coming all day long, his updates are tweets you’ll love seeing in your feed updates.

Tony Hsieh

Author and CEO of Zappos — @tonyhsieh

You have probably already read about some of Hseih’s unorthodox hiring practices at his online retail company Zappos. He is a modern day thought alchemist. I mean any guy that’s going to pay you NOT to take his job offer has enough of a contrarian thought process that I’m fascinated to learn more. It’s only through deconstructing the world that you can build it back up again sometimes. He doesn’t tweet often but when he does, it’s worth checking out.

Jillian Michaels

Personal Trainer and fitness-guru entrepreneur — @JillianMichaels

There’s something about Michaels. Maybe it’s her no-nonsense approach of turning a hellacious workout into a therapy breakthrough or her motivating way of telling you to fight back for your own life. Whatever it is, she is a Twitter must. She updates often, interacts a lot and has plenty of upbeat advice to get you off the chair and moving around.

Seth Godin

Founder of Squidoo and author — @thisissethsblog

Godin has a beautiful mind. His books make you think his approach to marketing is fresh and his blog is filled with short nuggets of thought gold. His Twitter handle is no exception. It provides daily thought igniters, along with inspiring blog post updates.

Pat Flynn

Author and podcast host of Smart Passive Income — @PatFlynn

Flynn’s tweets, like his podcast, are a must follow. As a thought leader in online marketing, he offers up weekly guests that are on the leading edge of all kinds of industries and he has great strategies for finding smart passive income. It’s honest, no hype and includes lots of daily updates about the podcast, marketing and more.

Jane McGonigal

Author, gamer and blogger — @avantgame

McGonigal is a gamer, designer and author of the New York Times Bestseller, "Reality is Broken: Why Games Make Us Better." She frequently tweets about personal passions, interacts on a regular basis with her followers and shares some innovative tech-related ideas and news (including of course updates on gaming). Gamification is a growing market sector that doesn’t always get as much coverage as some other tech niches. Following a woman who knows is informative and enjoyable.

Ali Brown

Entrepreneur and CEO of Ali International, LLC — @AliBrown

Hailed by Business News Daily as the “Entrepreneurial guru for women,” Brown has made an incredible mark. Although she specifically focuses her programs to motivate and mentor women entrepreneurs, there’s plenty to learn from Brown on how to be a total rock-star for both genders. She offers lots of resources, tips, inspiration and advice on her active Twitter feed.

Gary Vaynerchuk

Author, entrepreneur and CEO of Vayner Media — @GaryVee

Vaynerchuk’s enthusiasm and hustle are the kind of highly contagious things you actually want to catch. Even with over one million followers, Gary interacts with fans, gives great advice and updates and shares plenty of personal passion. He’s on Twitter a lot and there’s always something to learn from or chuckle at when you’ve got his tweets filtering into your feed.

SEE ALSO: 14 Apps Every Entrepreneur Needs

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Report: Square IPO 'Unlikely' In 2014

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jack dorsey 9:13

Square, the mobile payments startup known for its iconic credit card readers for phones and tablets, will not hold an initial public offering this year.

Earlier this week, The Information's Jessica Lessin reported that the company has been considering raising another round of funding that would push back any plans for an IPO.

Today, Fox Business' Katie Roof reports that the company's IPO has been postponed "indefinitely." 

In November, the company began talks with bankers from Goldman Sachs and Morgan Stanley about an IPO in 2014. A month later, the company met with executives from NASDAQ. 

Business Insider's Nicholas Carlson noted back in December that Square was attempting to raise a round of funding in order to purchase back company stock from employees and speculated that it might mean that the company's IPO was actually being pushed back.

After all, why raise money to buy stock from insiders if they could sell it in a few months on the public markets?

One possible answer is that the company didn't yet have the financials to support its $5 billion private valuation. 

Today's report implies that was the case. One of Roof's sources states that the company's “private-market valuation could not be substantiated by their revenues as a public company." Apparently the company is having trouble with its "revenue run rate," a key metric when looking at startups considering an exit.

That didn't stop the company from releasing 1 million secondary share in recent weeks, giving many employees the chance to sell their stakes in the company — $200 million worth of which were purchased just this week by Kingdom Holding, the investment fund ran by Saudi Arabia's Prince Alwaleed.

While it may not be heading for an IPO anytime soon, Square's financials don't seem to be holding back its actual business operations. The company recently announced that it acquired BookFresh, a startup that makes it easy to implement self-service appointment booking, and has began beta testing Square Pickup, a new service for ordering food from restaurants ahead of time.

SEE ALSO: Look inside Box, the hot storage startup set to IPO this year

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Here's What Successful People Eat For Breakfast

Twitter's Lock-Up Ends Next Month, But CEO Dick Costolo And Board Members Jack Dorsey And Evan Williams Will Not Sell Shares (TWTR)

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A tiny bit of news about Twitter for investors this morning.

CEO Dick Costolo, and board members (and former CEOs, themselves) Jack Dorsey and Evan Williams announce that they will not sell any shares when the company's lock up period ends on May 5. 

This is usually a good signal to investors that the top executives believe the stock has room to grow. 

However, the rest of Twitter's employees are probably going to sell a lot of shares. 

Twitter is trading around $40 per share, which is about flat with where it was after its first day of trading. It's 45% off its high point which came at the end of last year. 

Here's the SEC announcement:

TWTR SEC

UPDATE: Other big investors like Chris Sacca, Rizvi Traverse Management, IVP, and Kleiner Perkins also plan to hold their shares, according to Re/Code.

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