OhLife’s Daily E-Mails Motivate a New Wave of Online Diarists

This is the ninth in a series of profiles of companies funded this summer by Paul Graham’s Y Combinator startup incubator in Mountain View, CA.

Dear Diary,

This will be the last time I write in you. Your crisp pages and smooth leather cover have comforted me through many lonely nights. But I’ve found someone better to share my thoughts with, someone who cares for me in a way you can’t even imagine. He stores my thoughts forever and sends me sweet nothings every day. He reminds me of former happiness. He even lets me rewrite the past if I feel like it! Oh, Diary, don’t be sad. You’re just a book. You couldn’t hope to provide all the same features as OhLife—my new favorite online journaling service. Goodbye forever, my faithful companion.

Yours truly,

–Penny R. Kade

It’s the final death knell for the venerable old paper diary: a Web-based journaling system called OhLife that makes keeping a daily record of your life as easy as sending an e-mail message.

Sign up for a free account with OhLife, and every day at 8:00 p.m., the startup’s servers will send you an e-mail message with the friendly subject line “How did your day go?” All you have to do is reply to the message, and your note will go straight into your online journal at OhLife.com. You can attach a photo if you want, and you can review and edit your entries any time at the website. You can set the service to include a random entry from the past in the daily prompt, just to give you something to reflect on.

And that’s it. There’s no social sharing, no “Like This” or “Tweet This” buttons, no tags or maps or targeted ads. Entries are private, for your eyes only.

OhLife Screen ShotOhLife is brilliant in its simplicity, and the cleanliness of the basic idea spills over into the website’s spare, stylish design. Already, users have left more than 100,000 entries—and have told creators Reman Child and Shawn Gupta that OhLife prompting them to journal regularly for the first time in their lives.

According to Gupta, half of the people who join OhLife send in an entry at least every other day. That’s a level of engagement far beyond what other common blogging or online journaling tools have achieved. “Twenty-five percent of the feedback e-mails we get have the world ‘love’ in them,” Gupta says. “Not everyone has something to blog about, but everyone can write what they remember about their day. So people have a really intimate relationship now with OhLife.”

You’d probably never guess from the cozy look and feel of the site that Child and Gupta are 2006 electrical engineering graduates from UC Berkeley—or that it’s actually the fourth time they’ve built a startup. One of the pair’s distinctions is that their first company, Expensr, landed them on the cover of Business 2.0 in 2007, as part of a list of “15 companies that will change the world.” (It was acquired, then shuttered.) They’re also among a very small collection of founders who have been through Paul Graham’s Y Combinator startup incubator program twice. Their second company, ididwork.com, was part of Y Combinator’s Summer 2008 class in Cambridge, MA. It mutated into something called MeetingMix, which failed to take off. OhLife, their latest venture, was one of 36 startups to participate in the Summer 2010 session in Mountain View, CA.

“Oh, life!” might just as well be a motto for Child and Gupta, who never seem to give up. “One of Paul’s phrases for how you succeed as a startup is ‘You don’t die,'” says Child. “We might be the poster child for that at this point.” How the pair finally found an idea that’s gaining traction with Internet users, and why they think supporting users’ online journaling habit could be a profitable business, make an interesting little blog post.

The story starts with Expensr. After graduating from Berkeley, Child and Gupta were working real jobs and sharing an apartment in San Francisco when they got bit by the startup bug. They decided to try building a Web-based personal money management tool (think Mint or Geezeo).

“It was a struggle,” Gupta recounts. “It was bootstrapped, and we didn’t know any investors or other founders. We did get on the cover of Business 2.0, for their annual ‘Disruptors’ edition, but [the magazine] went out of business the next month.” A venture-funded product recommendations company called Strands bought Expensr for an undisclosed amount shortly after … Next Page »

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Wade Roush is a contributing editor at Xconomy. Follow @wroush

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