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 the Business 2.0 article, but quickly shut it down, assigning Gupta and Child to spin up a related product called moneyStrands (which is still around today). The pair left Strands after about six months.

Their next startup idea, and the one that got them into Y Combinator the first time, was ididwork.com. It was a bid to fix annual performance reviews—a ritual despised by both supervisors and supervisees. “The idea was, people on a team would keep a work log, and when they did something they’d just log that,” says Gupta. “The manager would periodically review the log and give you continuous feedback, rather than waiting a full year.”

After about nine months of work, Child and Gupta found that they were having trouble selling their system, mainly because annual reviews are, well, annual—meaning the pain they cause is more acute than chronic. “It’s such a seldom-faced problem; the second it’s over, you say ‘Thank God, it’s another year until I have to think about that again,'” says Gupta.

But the pair observed something interesting: customers who bought ididwork.com weren’t using it in the way it had been designed, as a substitute for annual reviews. Instead, they were using it as a way to keep their colleagues up to date, as a substitute for meetings of all sorts.

That led to a classic startup pivot. “The product shifted completely and we launched something new called MeetingMix,” says Gupta. “The premise was that we’d give you a wiki page for all of your meetings. You could send a link to this page to every attendee so they could suggest agenda topics and add action items, all on one page, and then document the meeting and all the key decisions.”

But MeetingMix, too, got into a fix, with little uptake from users. “There was adisconnect,” says Gupta. “Everyone would say ‘If meetings actually did that, it would be awesome.’ The problem is that creating an agenda takes extra work, which offsets any benefits accrued.” MeetingMix is still online today (as is ididwork.com), but most of its remaining users are “diehard people” with a specific interest in the art of running productive meetings.

So Child and Gupta set off in search of a new problem to solve. At this point, they’d been through a lot—three product launches in less than four years. “A lot of stuff has happened, and I’m afraid I’m not going to remember all of it,” says Child. But he wasn’t much good at writing it down. “I have a stack of Moleskines in my closet where literally, the first 10 pages have stuff, and then it dies out.” Gupta, too, says he’s tried to keep a regular journal, but that he was always more of a “serial attempter” than a serious diarist.

From their previous ventures, Child and Gupta had learned how difficult it can be to get users to adopt new behaviors. But everyone already uses e-mail, and the pair eventually hit on the idea of using it to help would-be journalers jumpstart their daily writing practice. “This notion of applying it through e-mail made the whole idea of keeping a journal make sense,” says Child. “There are no new habits or anything like that.”

OhLife debuted in August, and by the time I first met with Child and Gupta in early September, the service was already home to over 100,000 entries. They think the fast early adoption is partly the result of the fact that OhLife entries are meant to be personal and private, which makes it the virtual opposite of blogging. Writing for yourself, Gupta points out, doesn’t require as much thought or caution as writing in full public view. “I wouldn’t put any of my entries out in public,” he says. “Not out of embarrassment or shame—it’s just that everyone else would find them so mundane.”

Word about OhLife has spread entirely by word of mouth. “I think people really like the design, which has gone a long way for us,” says Gupta. “We’re putting a lot of effort into simplifying how it works.” The fact that entries are secret means OhLife’s content is, in a sense, anti-viral—so the startup isn’t benefiting from the usual social media boost that it might get if, say, the whole service were a Facebook app with entries visible to friends. But “people are constantly tweeting about it” nonetheless, Gupta says.

For now, Child and Gupta aren’t anxious to monetize OhLife; expenses are low, consisting mainly of storage and bandwidth. Premium subscriptions providing extra storage space for photos or even video diary entries could be one possible revenue stream. Targeted ads inserted into the daily e-mail prompts are another idea. “We have permission to e-mail our users every single day,” Gupta points out. “You could put an ad into that, and people probably won’t mind. Having that 25 percent ‘love’ goes in our favor a bit.”

The startup is working to raise a round of seed funding, but since “the core feature set is pretty solid,” in Gupta’s words, much of the money will probably go to marketing and distribution rather than product development. “The more money you raise, the more you can pay to acquire users through ads,” he says.

Through OhLife, Child and Gupta have been getting validation of the kind that escaped them with Expensr, ididwork.com, and MeetingMix. “We’ve been getting quite a few e-mails from people who never thought they would journal, but it’s so easy now that they have no reason not to,” says Child.

Even engineers from OhLife’s fellow Y Combinator startups are using OhLife, Gupta says. And perhaps most gratifying of all, the service seems to have a therapeutic benefit for some users. Says Gupta: “We’ve had people e-mail in who said they were depressed, and just the act of using OhLife and trying to write each day about something good that happened improved their spirits tremendously.” That’s the kind of pain point more startups should be trying to address.

Wade Roush is a freelance science and technology journalist and the producer and host of the podcast Soonish. Follow @soonishpodcast

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5 responses to “OhLife’s Daily E-Mails Motivate a New Wave of Online Diarists”

  1. Tim says:

    I’m not sure how I feel about this idea. There’s only been one time in my life where I have kept a journal sacredly – when I studied abroad during my college years in Spain. I wrote in a journal every single day without fail and I’m so happy I did.

    Some concerns I have with this electronic journaling concept:

    1) Journals elicit nostalgia. Over the course of the years as time goes by, the pages yellow, the ink smears a bit, but it’s REAL. It’s physical. You can hold it. I brought that journal all the way to Spain, wrote in it in my little apartment, and it traveled back with me. It accompanied me on all my trips and adventures in Europe. There’s a lot of sentiment in that.

    2) People sit in front of computers all day. I’d be surprised if people don’t find more typing to be a chore or laborious.

    3) What’s OhLife doing to address privacy? Journals are intensely personal, and much of the information is sensitive. Who wants to write a journal, look back on it, and read “I had 3 cups of coffee today, work was long, etc.” It’s about relationships, interactions, personal thoughts – how things made you feel. Could these entries ever be hacked? Does OhLife has access or can they read people’s entries?

    I want to hold my journals and feel a connection to them. Sending my deepest thoughts/feelings out to some “cloud” feels….just not right.

  2. Wade RoushWade Roush says:


    Good points. Shawn and Reman spoke to me about having their own Moleskine notebooks, so I think they understand the appeal of that kind of journaling as well, and they aren’t necessarily promoting OhLife as a replacement. But if you’re on e-mail all day already, it might often be easier to shoot off a note to your OhLife account than to find your journal, find a pen, and find a quiet place to sit down and write. (But one thing that’s missing from OhLife is a way to doodle, draw, paste in found items, etc. — that’s still one advantage of paper journals.)

    Regarding security, I didn’t put this into the piece but I did ask Shawn and Reman about it, and they’re doing all the standard things. The site is secured by SSL; all of their server software is up to date; they close down the usual server ports that hackers go after, et cetera. As long as you protect your password, your entries should be pretty secure. To provide extra assurance, they said they’re thinking about offering encryption of entries as a premium service.

  3. Julie says:

    I’ve been using OhLife since August, and honestly, most of my entries DO consist of “I had a long day at work, now reading a book/watching a movie.” On weekends, I have more exciting days.

    But sometimes I look back, and I see the title of a book I really enjoyed, or see that my boyfriend picked me up from work one day, and it’s nice to read those things.

    I’ve been keeping journals for the last 10 years or so (since I was 13, probably even earlier). I’ve had physical journals, as well as electronic. Both were very short lived. Granted, my life was more melodramatic when I was 13 (omg, new high school! omg, new boyfriend!) so I had much longer entries and more actual thoughts in it. And sometimes I do go back to my livejournal and see those entries–including one about losing my virginity and rekindling a friendship with my best friend from elementary school. It was an interesting period of my life to document. I also didn’t write entries every day–I only wrote them when I really had something to say. Most of them were about fights I had with people–my mother, my boyfriend. a friend. I don’t really have that anymore, so naturally, my entries are more boring.

    I’m still looking forward to reading them in a few years, though. I’ve always been the type of person who likes to keep records of all the little mundane things.

  4. Erika says:

    I’m with Tim… I guess I’m “old” enough that I just wouldn’t feel comfortable storing private thoughts on a server without their being encrypted before they ever hit the other end of the e-journey.

  5. Thierry says:

    I am using ohlife to remind me that every day I have to do something extraordinary. Otherwise my day is lost!