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What I learned from Twitter's leaders

By Anil Dash, Special to CNN
updated 6:48 PM EST, Fri November 8, 2013
STORY HIGHLIGHTS
  • Anil Dash: It's worth looking at skills of Twitter execs who led company to successful IPO
  • He says CEO Costolo is a former stand-up comic; improv thinking spurs company adaptability
  • He says other top figures guided principled stances, showed value of civic-mindedness
  • Dash: Founders brought money, attention to detail, ability to explain in human terms

Editor's note: Anil Dash is an entrepreneur and writer in New York. He is the co-founder of ThinkUp, a new tech startup in New York City . He blogs at dashes.com Follow him on Twitter.

(CNN) -- The Internet is buzzing with news of Twitter's initial public offering on Thursday, inspiring enough enthusiasm from investors to push the company to a $23 billion valuation in its first day. It has been quite a ride for a company started just seven years ago, attracting just a few geeky users at first, and then accelerating to eventually reach more than 232 million active users each month.

The company has been through an extraordinary set of triumphs and tribulations along the way. I've watched much of this happen—I work in the tech industry and count many of the leaders and founders of Twitter, since its earliest days, as friends—and I think I can identify some of the more human lessons we might take away from Twitter's milestone. The rest of us aren't going to get rich from Twitter's IPO, but the people who are embody some basic truths about what it takes to take a small company big.

Anil Dash
Anil Dash

Their work informs the work I do each day, both in my own new startup ThinkUp and in my life overall.

Dick Costolo, CEO: Costolo is widely acknowledged as one of the most innovative executives in the tech industry, creating a series of companies focused on delivering real-time information. But while he famously has a background in stand-up comedy (he shared the stage in Chicago years ago with folks like Steve Carell), there's a bigger lesson to be had here: That serious business can be informed by a sense of improvisation. Improv is based around the idea of saying "Yes, and..." rather than "No, we can't," and that's a fundamental philosophy for building a business that can adapt to the real world.

Katie Stanton, head of international strategy: In between her stints building products at Yahoo and Google and her current role heading international efforts at Twitter, Stanton worked both at the White House and the State Department. That she did this showed an awareness of the importance not just of having a global perspective, but of serving—and interacting with--one's community, one's city, or country. More of the tech industry, and every industry, would benefit from being more civic-minded.

Jason Goldman, former vice president of product: One of the least-heralded leaders of Twitter during its early days, Goldman was a quiet but forceful voice for improving the process of running Twitter as a company. Much of the hardest work in building anything big and ambitious gets done in roles that aren't glamorous, that focus on just trying to get a little bit better each day.

Chloe Sladden, head of media: Sladden was one of the first people at Twitter to think systematically about how the company would connect to more traditional media, like television. Inside the tech industry, people are used to making big distinctions between technology and media, or between "new media" and "old media," but it's a huge insight to realize that those boundaries are increasingly arbitrary. That kind of thinking is how opportunities are created.

Behind-the-scenes drama at Twitter
High stakes for high-profile Twitter IPO

Alex Macgillivray, former general counsel: At several points in its history, Twitter made choices to do the right thing when it didn't have to, choices that a lot of companies have backed away from. From its stand on free speech to its efforts to be more transparent about the ways it utilizes users' data, many of Twitter's initiatives happened because the company and its lawyers were willing to do extra work on behalf of what was right. One of the most consistent advocates for fighting the good fight was Alex Macgiillivray, who left the company last summer. His advocacy has hopefully influenced all kinds of companies to stand up for people's rights.

Biz Stone, co-founder: In the many stories and books that have already been written about Twitter's history, the role of Christopher "Biz" Stone is one of the least understood; reporters have often left it as, essentially, "He seems like a nice guy." His contribution to Twitter, and to the many projects he has worked on before and since, has been so much more than that. He has displayed a consistent ability to articulate—in human language, understandable to all-- what's valuable about a piece of technology. This is perhaps best exemplified by his early description of Twitter itself: "The messaging system we didn't know we needed until we had it." In a tech industry that often seems disconnected from regular people, this is one of the most crucial skills to have.

Jack Dorsey, co-founder: Though he's become one of the most famous names in technology, the most striking thing about Dorsey's career is his focus on every small detail of how things are presented, whether that's a product or a company or a process. That kind of sweating the small stuff is what propels a company's ambitions, and it's a trait Dorsey has carried into his mobile payments company, Square.

Michael Sippey, vice president of product: Sippey was among the earliest people to create a blog on the Internet, and more than a decade and a half later, he's working on building more features like photos and video into Twitter, based on the fundamental ideas of multimedia sharing that were pioneered during the early days of the blogosphere. That kind of fixation on a big, meaningful problem like finding better, richer ways to communicate with friends and communities, is a tough thing to stay focused on in the short-attention-span tech world, let alone on which to build a long career.

Evan Willams, co-founder: Perhaps no one person is more responsible for Twitter's existence than Evan Williams, who bankrolled the company out of his pocket in its early days, and serves on its board today. The headlines from the financial press will be about how Williams became a multibillionaire after Thursday's IPO, but the bigger story is one of his sheer persistence. Williams was co-founder of Blogger, where the company went through a near-death experience before being acquired by Google, and just a dozen years ago, he was tapped out. But he kept with it, and brought that same persistence to the ups and downs of Twitter--and is putting the same ethos to work in his new company, Medium. There's an important lesson in that example of never giving up.

The strengths and stories of the people who built the company to its success—and there are many more--are instructive for any company. At the same time, of course, they are just people—smart ones, but imperfect, and lucky, too. Certainly it helps that all these smart people grew up in America, where they never had to worry about clean water or good public schools or political instability.

The privileges we enjoy in the United States allow us to succeed on this level, and it's why I challenge Twitter to extend these kinds of opportunities more broadly by expanding the diversity of its board, and in the process better reflecting its increasingly international and diverse user base.

On a day when many are celebrating Twitter for its financial success, and lauding the value of its stock price, we can find a deeper value in the personal stories of this handful of people who helped build Twitter. Hopefully the positive values that helped Twitter get to this point are what this newly public company can use as its definition of "success" going forward.

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The opinions expressed in this commentary are solely those of Anil Dash.

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