Sunday, November 30, 2008

A New Setup

A little more than a week ago, we moved into an apartment in Foster City/San Mateo. The big plus here is that we don’t have to rush through an hour of traffic to get to meetings in the Valley. Suburbia provides fewer distractions here than you would have in San Francisco, but the hipness level is low, and a good bar is hard to find.

Fewer distractions have allowed us to make progress on the prototype. It turns out that this is more productive than working in a coffee shop. My commute now takes 10 seconds, and my workspace has a nice Dell flatscreen monitor and my favorite ergonomic keyboard. In addition, we have blocked YCombinator’s Hacker News and similar sites on our router, which resulted in an additional productivity boost.

Things are progressing well on other fronts, too - I’ll keep you updated. For now, it’s back to work.

Tuesday, November 18, 2008

Welcome Fabian!

I'm happy to announce that for the next 3 months, I'll be working with an old high school friend, Fabian Siegel. He's in Germany but he'll help code up prototypes and the initial product. He's not my cofounder: I'm still working on that (watch this space!).

I met Fabian over a decade ago in school where we shared a common love of computers. Together, we wrote a Command-and-Conquer-like isometric real time strategy game. We had DirectX graphics with little vehicles moving around the a map. However, we never got to the point where the vehicles would shoot at each other, thus severely limiting the game's commercial potential. Fabian went on to study Computer Science in Munich, Germany, and later switched his focus: He now has an M.D. and can resuscitate us in case we pass out from working too hard. On the side, he's also been running a web hosting company and is a mail server guru.

In his words: Let's rock!

Monday, November 17, 2008

A Model of Your Inbox

I've been thinking a lot about how users view and manage their inbox. This post is about the model I came up with. I'm basing this on my own experience and on having talked to dozens of people about their email habits. But since this blog also is read by lots of email enthusiasts, I'd love to hear your feedback: Does this make sense? What am I missing?

Four Quadrants

Every single email message youreceive can be classified into one of the four quadrants below. Important emails are the ones you need to take action on. Urgent emails are time-sensitive. Urgency does not necessarily imply importance: Your coworker's cake will be gone in a few minutes, but it's not necessary to take action on that, especially if you're on a diet.

The key insight here is that the stuff you care about are the emails on the left. These are the emails that make it worth checking your Crackberry every few minutes. They emails that keep you awake at night.

Filtering the Important

How can you filter out what's important? My theory is that for humans, that's actually the easy part: You often easily determine importance by just looking at the sender of the message. Roughly, senders fall into three categories:
  1. Crap: these are easy to remove: iTunes Receipts, Amazon notifications, LinkedIn emails, frequent flier statements, and the like. Not important.

  2. VIPs: You know who they are! Major customers, your manager, and your girlfriend belong in this category. Important.

  3. People you know: These are the non-VIPs that you still want to deal with. I like to think of this category as the intersection of your Facebook and LinkedIn connections. Mostly Important.

  4. Everyone else: Recruiters and salespeople, senders you don't recognize. Mostly not important.

Research indicates that people use senders as their main importance indicator [1, 2]. The task of filtering out important email is easy, and you could probably train a classifier to very high degrees of accuracy.

Managing Later vs. Now

I believe that this is the heart of email overload. Remember how I said that the left side is what matters. I like to label the two subcategories as "Later" and "Now" [3].

The workflow should be that you decide whether you want to deal with an email now or later. You respond to the "now" emails and they disappear into the archive. The "later" emails haunt you until you're done with them.

This is the point where today's email clients fail. Users try various mechanisms to manage now/later and to do/done: Keeping emails unread, starring them in Gmail, and filing away stuff that is done into an intricate foldering system. The number of email management strategies that users come up with impressive [4].

But none of this works. Emails that are unread and starred disappear from your main view. Out of view, out of mind. Poof. There is no pressure to act upon them. In contrast, filing away emails that are done requires an amount of discipline that few users have. I think that the inability of managing now/later and to do/done is one of the main reasons for email overload.

Wrapping Up

Let's review. I've outlined three theories here:
  1. Your incoming all fall into one of the four quadrants of urgency and importance. What really matters is the important stuff, which breaks into "Later" vs. "Now".

  2. It's easy to filter important vs. not important.

  3. It's hard to manage Later vs. Now because the current tools are broken.

I'd love to hear your views on my theories. Drop me a line or leave a comment.


[1] Gina Danielle Venolia, Laura Dabbish, JJ Cadiz, and Anoop Gupta. Supporting email workflow. Technical report, Microsoft Research - Collaboration and Multimedia Group, September 2001.

[2] Olle Baelter and Candace Sidner. Bifrost inbox organizer: giving users control over the inbox. In NordiCHI '02: Proceedings of the second Nordic Conference on Human-computer interaction, pages 111-118, Aarhus, Denmark, 2002.

[3] The "Getting Things Done" school of thought has a more intricate system than this, but I think that Later / Now is the essence of it.

[4] Steve Whittaker and Candace Sidner. Email overload: exploring personal information management of email. In CHI '96: Proceedings of the SIGCHI Conference on Human Factors in Computing Systems, pages 276-283, Vancouver, British Columbia, Canada, 1996.

Wednesday, November 12, 2008

Questions for Cofounders

I'm in the middle of solving the highly nonlinear equation of idea, cofounder, and investment. I wrote about my cofounder search here (if you're interested, drop me a line).

Startups fail for many reasons: Running out of money, no product-market fit, and cofounder drama. Now is the time to protect against drama. I want to set reasonable expectations on both sides and have good conflict resolution mechanisms.

Below is the list of questions I want to address with potential cofounders, somewhat inspired by Dharmesh Shah's list (his list is more generally applicable - mine is more about personalities).

  1. What's your long term life goal? Some want to be the next Bill Gates, Larry Page, or David Filo. Others want to get rich and retire. How did they come up with their goal? How does this startup fit into that goal? If this fails, would they do another one?

  2. What kind of company do we want to build? Should it be a 37signals – a profitable thought leader? Or do we want to shoot for the moon and be a Google? Get a clear reading on your cofounder's ambitions and long-term commitment.

  3. What kind of work environment do we want to create? How are we going to treat employees? Lavish perks like Google? Strict hierarchies like GE? Think about what kind of employees you want to have, how open you want to be with them, and whether you want to hire fresh hotshots or experienced veterans.

  4. How are we going to split responsibilities? What will we be doing on a daily basis? The best situation is where founders all have clear ownership of one part of the product, or processes like fundraising and bizdev. Make sure you can trust the business guys. Avoid situations where cofounders with similar backgrounds all focus and battle about one part of the puzzle.

  5. How are we going to resolve conflicts? Is it enough if we have a one-on-one meeting every week where we discuss problems, or do we feel more comfortable with a written mechanism? A friend pointed out the book Under the Radar which described the Red Hat founders' protocol: A founder with a problem could write a one-page memo on letter paper. The others would have to respond in writing within the next 24 hours.

  6. What are our preferred work patterns? You'll have to be able to stand each other all day. Make sure you understand each other's work styles, hours and quirks.

  7. Who makes the final decision? I.e., who's the CEO? Multiple founders might want this this position. It seems prestigious but it's hard. Choose wisely.

  8. How much of the company will each of us own? A conversation that can easily get heated. Equal parts are probably wrong. Cofounders who contribute less to the equation should get less. Yet it's hard to measure contribution. Also, you should vest - agree on the parameters.

Once you get into the details, the list goes on endlessly. Are we going to sign emails "Founder" or "Co-founder"? Do we have full access to each other's calendars? Who's going to authorize payroll? Do we reimburse our cell phone bills? Most of these won't make a difference though.

Let me know if I'm forgetting something. I'd love to hear your thoughts and experiences from similar situations. What results did you get out of these conversations? Any sources of drama I forgot?

P.S.: I recommend keeping Dharmesh's questions and conflict lists bookmarked.

Wednesday, November 05, 2008

Making up Emails for Mockups

When mocking up communications software, you have to make stuff up: You want to show a realistic inbox, messages that seem real, and clearly illustrate the use case you’re trying to support. Mockups help others grasp what you're building, and they help get you rolling on the prototype.

Photoshop and Corel Draw are my friends, and it's easy to find design inspiration on the web.

But how do you come up with the data? Some ideas:
  1. Use your own email. Duh. Sounds reasonable. But you don't want your confidential emails in your business plan. The girlfriend might not appreciate the shoutout. And startup founders’ emails do not represent a common use case.

  2. Enron Corpus. This is good for business scenarios, with some small problems: No attachments, no sender names (although you can make them up), and the depressing emails towards the end of the company: "Dear top management, please don't fire us now!". Use the Trampoline Enron Explorer to get to the data.

  3. Celebrities. Great for consumer email scenarios. My friends at Google used to mock me for including Natalie Portman in most mocks, but People Magazine is your friend: Just use your personal email and add celebrity names. Added benefit: If you choose the right celebrities, that will trigger positive emotions with people looking at the mocks.

If you have a more ideas, let me know.