The Non-Overnight Success: How Twitter Became Twitter


What did Twitter look like before it was Twitter? Let us begin the story with an image…

Jack Dorsey’s first sketch for what would become Twitter (Photo: Jack Dorsey and d0tc0m)

This photo was first shown to me by Peter Sims, a former venture capitalist and now friend.

Pete and I share a number of common interests: wine, K-os, long dinners, and above all… little bets.

It’s a favorite topic of conversation.

Perhaps a year ago, after a quick tour of the Stanford Institute of Design (, Pete and I sat talking about start-ups in Tresidder dining hall. He was working on a new book about innovation, which he wanted to bridge different worlds, to explain the shared traits of the game changers.

The question he posed was simple: if you look at the biggest successes in the world, whether Apple CEO Steve Jobs, comedian Chris Rock, or award-winning architect Frank Gehry, what do they have in common?

Answer: the bigger they are, the more small bets they make.

Becoming the best of the best is less about betting the farm (a common misconception) and more about constant tinkering. Within Pixar or within Amazon, there is a method to the madness, but it’s not haphazard risk-taking.

In the following guest post, Peter will look at the unlikely evolution of a little tool. It’s a little tool now used to overthrow governments, and a tool that’s become a company some value at more than $10 billion: Twitter.

How the hell did it happen?…

Enter Peter Sims

We’re taught from a young age to avoid errors and failure at all costs, yet as any successful creator or entrepreneur will attest, breakthroughs don’t happen without them.

So we have to be willing (and able) to think differently. Instead of trying to develop elaborate plans or perfect ideas, we need to make small, affordable bets in order to learn quickly, build momentum and networks, and expand our abilities and resources in order to discover unique ideas and opportunities.

Consider how Twitter came about. It didn’t happen overnight. Jack Dorsey had been, in his words, “obsessed” by how people moved, interacted, and communicated since the early 1990s. So, he learned basic computer programming, created maps with dots on them, and used information from Manhattan dispatch systems to track the movement of bike messengers, taxis, police, firefighters, and couriers. It was a start.

Dorsey then transferred to New York University and got a job as a programmer with the largest dispatch company in the world. He learned a lot in the role and eventually focused on the short format messages that people sent to large dispatch boards. “This became the basis for all of my work going forward,” he recalled.

After moving to the San Francisco in 2000, Dorsey continued to tinker with short messaging ideas. He started a company that dispatched emergency and taxi services from the web, but soon realized how little he knew about start-ups. Coming at the end of the dotcom era, the timing was bad, too. “The company scuttled and was more or less a failure,” he acknowledged.

Yet he would learn from it.

Dorsey continued to use instant messaging and LiveJournal (the early blogging platform) to post updates on what he was doing – simple things like, “I’m on the phone” or “I’m listening to the Black Eyed Peas.” Once again, these were small, achievable steps toward Jack’s larger interests.

Then one night, Dorsey couldn’t sleep and sketched out an idea on a white board. The idea was to exchange short “status update” emails with friends using his RIM 850, a predecessor to the BlackBerry. The device had four lines of text good for short format messaging, but unfortunately his friends didn’t have RIM 850s.

So that experiment didn’t go anywhere either, but Dorsey got little bit smarter, a little bit better, and a little bit closer to a big idea.

Around that time, Dorsey sketched out what would become the basis for Twitter several years later. On top it reads “STATUS,” followed by a short fill-in the blank where he wrote “Reading.” But lacking resources, Dorsey had to get a real job while continuing to tinker on the side.

Dorsey was eventually hired as an engineer at Odeo, a podcasting company where people weren’t in love with podcasting. The company was, in fact, going nowhere, so founder Evan Williams asked employees for new ideas.

One night in 2006, Dorsey’s colleague sent him the first text message he ever received. “I had no idea what this thing was,” he remembered. But as Dorsey and his colleagues talked more about text messaging, he realized the short message format could be the missing link.

Williams gave him two weeks and another programmer to develop the idea. After the prototype was a resounding success internally at Odeo, Williams upped the ante for a six-month project then launched a full-scale version publically in July 2006. Twitter would consume more and more resources until Williams spun it off as a separate company in 2007.

Of course, luck was an important factor, but Dorsey’s approach was brilliant. He focused like a laser on short messaging and made hundreds (if not thousands) of small, affordable bets in that area, most of which failed. But with each step he got slightly smarter, better, and closer until he ultimately achieved a remarkable feat.

It’s an approach that the best entrepreneurs and creators have learned to do well, but anyone can do it. Jack began when he was a programmer.

It begins with a little bet. What will yours be?

# # #

More on Peter Sims: The above guest post is by bestselling author and former venture capital investor Peter Sims. His new book is Little Bets: How Breakthrough Ideas Emerge from Small Discoveries. For a free excerpt, click here.

Posted on: April 20, 2011.

Watch The Tim Ferriss Experiment, the new #1-rated TV show with "the world's best human guinea pig" (Newsweek), Tim Ferriss. It's Mythbusters meets Jackass. Shot and edited by the Emmy-award winning team behind Anthony Bourdain's No Reservations and Parts Unknown. Here's the trailer.

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107 comments on “The Non-Overnight Success: How Twitter Became Twitter

  1. Interesting post….BTW Dorsey has a different kindda mind…..I love square and impress with the fact that he went for a new startup when twitter was/is growing crazy


  2. Dope dude!

    Had no idea you were a K-OS fan. Fun fact, did you know that K-OS stands for Knowledge of Self. Homeboy’s apparently a part of Socrates’s long lost entourage.

    Thanx for the inspiraction Tim!


    • I agree. I have learned so much more from my mistakes than my successes! If you can observe a mistake with curiosity you see it with a mind that finds itself going deeper into solving the problem rather than running away from it.


      • Tim,
        Now THAT’S some quick turn around and excellent customer service! A mistake pointed out and corrected within seconds! 4HrWW was amazing! Thank you for the inspiration! I’d like to share an upcoming endeavor with you and perhaps get your insight as to the viability and automation you speak of.

        Stacey O.


      • Tim, in a “how to start a business” interview you mentioned that there is a book on financial statements. You said Buffet wrote the intro. I would really like ot read that book. What is it?!


  3. Great post, most of the material out there encourages us to plan and have everything laid out before making a move. But I like the advice stated in the post, “We need to make small, affordable bets in order to learn quickly, build momentum and networks, and expand our abilities and resources in order to discover unique ideas and opportunities.” Which is true, because sometimes elaborate planning makes me paralyzed and instead of moving forward I become caught in the process, rather than observing and testing the small incremental gains.


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  5. Always love reading stuff here. I’ll have to read that book now to learn more.

    Do you believe the 4HWW followed the same path with little small bets resulting in becoming a bestseller?


  6. I appreciate the story of the time it took and the continual “failures” as an example of the usual entrepreneurial process. We need a different “ethos”. School teaches you to get it “right” — perhaps because producing workers for manufacturing needed precision of process? Whereas to invent, we need to enjoy the process of getting it “wrong” most of the time on the way to creating something of value.

    Like I tell my kids, if you’re not failing, you’re failing!


  7. I don’t feel so bad now, especially since he struggled since the 1990s :) I appreciate his efforts. I learn so much from my twitter feeds. Yes I stalk you on twitter too, Tim :)



  8. I’ve often had weird serendipities happen to me. One seemingly random experience might prepare me for something much bigger in the future.

    I can see how “Tinkering” — constantly tweaking your way in the direction of a goal, goes hand in hand with serendipity or “getting lucky”


  9. I’m guilty of over-planning from time to time for sure, looking for more information or perfect timing. Classic paralysis by analysis. Love the theme of taking smaller risks, and correcting course along the way…much easier to get and maintain momentum.

    Thanks for the post, Tim


  10. Great article Tim. I already forwarded it to a couple people. It’s interesting because I am in the process of creating a startup and when I saw your picture of what twitter looked like on paper it reminds me of exactly what I am going through right now. Hopefully this can be my muse.

    Keep writing these articles, they help immensely.


    • @Jesse that’s what I got out of this article as well, the realisation that all those notes captured (evernote is brilliant) path the way to significance.

      Just realised the importance of getting the beta out there to let it naturally evolve with the customer.

      Good luck musing.

      Twitter started for me as a free party/live band notification tool, now look at what it’s become.


  11. I love this! I am a business advisor, and lately I have been thinking about the concept of fine-tuning a business. So many owners I work with expect results to be achieved by doing something big – which occasionally is necessary – but most often it’s the small, directionally correct (or not) changes that make the big difference. My mantra lately has been “test and learn,” and now I can refer them to this blog post for more ammunition.

    Thanks for sharing this and I look forward to reading the book!



  12. Very cool. Mainly the “luck” part for twitter occurred when the Miracle on the Hudson picture of the US Airways flight was uploaded to twitter by Janis Krums…


  13. I hadn’t the back story on Twitter thanks for sharing.

    Way too often we don’t hear about the “9,999 tries” just the one that worked. I think too may people really believe that people simply “get lucky.”



  14. Mr. Dorsey must have received or at least heard about text messages (SMS) before 2006. Is it really possible that he had no idea what it was until so late, especially for a guy who is so passionate about, well, short messages?