10 Inspirational “How I Did It” Stories

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The best way to learn is often times to just jump in and do it, but hearing how other successful people did it first can be inspirational. The ten stories below detail how other people got their web startups (or freelancing or consulting businesses) off the ground and some of the lessons they learned along the way. Paying attention to what people have done before can help us to avoid making the same mistakes and emulate the successes. Please feel free to share other “How I Did It” stories in the comments below.

1. Peldi Guilizzoni

This is the story of how a young coder from Italy, who was until fairly recently working at Adobe, quit his job to launch Balsamiq. Balsamiq is a Micro-ISV that makes a product that helps developers create UI mockups easily in Confluence, JIRA and XWiki. Guilizzoni details how and why he left his job at Adobe to bootstrap his startup, and how he balanced his personal life, which includes a wife and kid.

2. Tom Preston-Werner

$300,000 is a lot of money. For most people, turning down that kind of guaranteed cash and a 3-year contract at a large software company would be difficult. For Preston-Werner, the decision was difficult, but it has so far turned out to be the right decision to make. He details how he turned down a huge contract at Microsoft after Powerset was acquired to work full-time on GitHub, the startup he was bootstrapping with a couple of partners.

3. Loic Le Meur

For Loic Le Meur, it paid to have powerful friends when he was pitching his idea for video startup Seesmic. Even so, his story of how he framed the pitch is inspiring and helpful to read for anyone out there looking for cash for their startup — or just trying to figure out how to talk about their idea.

4. Carlo Feliciano

Getting started as a freelancer is tough enough. Now imagine doing it in a field you’ve got no formal experience in. How do you get people to buy your services if they’re the first to do it? Carlo Feliciano knew he wanted to do freelance copywrting, but was just out of college. In this post at Freelance Switch he details how he went from “clueless about freelance copywriting to consulting with my first client over Skype” in just a couple of months.

5. Nina Monk

Business writer Nina Monk’s story from the New York Times actually comes from the year 2000. But it’s a fascinating read about what it was like to start a web startup in the heady days before the bubble burst, nonetheless (a taste: “No one will take you seriously with that $50,000 figure,” I was told. “You need to give potential investors something to dream about.”). And her startup, urbanhound, still exists, so she’s definitely done something right.

6. Markus Frind

A lot is made about how Frind bootstrapped his way to creating one of the most successful dating sites online, and did it all by himself. This is the story of how Plentyoffish.com owes its start to Frind accidentally learning about the concept of Search Engine Optimization in 2003 while working for what appeared to be a tanking startup.

7. Jordan Goldman

Goldman’s path to funding just out of a college is a unique one. Armed only with an idea, this is the story of how he essentially cold called a list of wealthy alumni from his college until one of them would give him a few minutes to talk about his idea. From there, 23-year-old Goldman used his natural gift of gab to land funding for his user-generated college guide site Unigo.com.

8. Ryan Carson

Getting down to the nitty gritty of what it actually takes to make a web app, Carson uses a guest post a TechCrunch to detail how he and a team of nine people (though he says you only need three), took 32 hours out of their busy lives at Carson Systems (which makes web applications and holds conferences and training sessions), and created a web app for $10,000 — a week of salaries at the company. The post has some great tips and ideas about how to build the perfect work environment for your startup team.

9. Matt Inman

Inman, who is the former CTO of SEOmoz, has been called a “SEO genius,” and he put that talent to good use to get his dating site Mingle2 to the top of key Google searches in a very short time. This post, however, is more technical, and details how Inman actually built the site in just about a week and a half worth of work. There’s some great advice here about how to actually conceive, code, and design your web startup, and do it in a very short amount of time with limited resources.

10. Seth Godin

Seth Godin has a the ultimate personal brand. His books sell, his blog is widely linked to, and he is in super high demand as a speaker. But attaining guru status didn’t happen by accident. This story in BusinessWeek details how Godin followed his own advice to become a web superstar.

Bonus: Derek Sivers

Bonus number 11 — because it was published today after I had already completed this post. Derek Sivers talks to Venture Voice (a podcast) about how he built CDBaby.com to an 85 employee company with $100 million per year in revenue, and all with no outside funding. Oh yeah, he also sold the company this summer for $22 million and controlled 100% of the equity when he did it.

Josh CatoneJosh Catone
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Before joining Jilt, Josh Catone was the Executive Director of Editorial Projects at Mashable, the Lead Writer at ReadWriteWeb, Lead Blogger at SitePoint, and the Community Evangelist at DandyID. On the side, Josh enjoys managing his blog The Fluffington Post.

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