Monthly Archives: January 2012

Email Innovation Lacking, Still a Huge Opportunity, Hard to Exploit

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For the last two weeks or so, I was having a ton of Mac problems. It seemed that my OS had gotten corrupted, so I thought that upgrading to OSX Lion would clean up the OS and upgrade me since I was going to do it eventually.
The nightmare that threw me into is probably best told over a beer – somehow I was one of the unlucky few where OSX Lion upgrade over an existing OSX Snow Leopard was just not possible and became unstable over a few days, leading to not being able to boot the Mac at all! I managed to roll back to OSX Snow Leopard (no little trick there!) and think I’m back in action.
But this post is not about my upgrade problems. It’s about email. During that small window of time when OSX Lion was working, I opened up the new Mac Mail and saw….a visual makeover and the additions of grouping by conversation. In fact, it defaulted to conversation grouping. What a disappointment. Here was an opportunity to revolutionize email and the most innovative force in technology decided to just do a visual makeover and add what Gmail has had for a few years now?
Like I said, disappointing.
Email has not been innovated in decades. It’s still the same old thing. Oh, people have tried, but then most fail miserably as startups. Some of the things people have tried or are doing:
1. Grouping and viewing messages by sender.
2. Turn email into a social network and view messages that way.
3. Adding windows to email to make it into a professional or personal CRM.
4. Graphical views of email that are beyond the rows of messages we see today.
5. Group email by conversation.
Perhaps item 5 is the most dominant innovation in email, and most notably through Google’s Gmail. In fact, it is dominant because Google refuses to give you another interface. If you sign up for Gmail (or Google powered business email) and you use their web interfaceYou also see this in Facebook messaging, but I believe Facebook’s implementation is subtly better because they always show the conversation that has the latest message in on top. If you use offline Mac mail and pop into Gmail occasionally, Gmail always shows the conversation that came in first on top that you have not read. It takes a few days of working in the Gmail interface before their sorting becomes somewhat effective. This is why I find the web interface to Gmail so annoying; since I go back and forth between Mac Mail and Gmail, Gmail never gets the chance to stay current to what I’m doing and when I do use Gmail in the browser, it’s always sorted in the wrong way. And I always lose key messages because the little flags and bolding are the only signals that something new has come in. And it makes me read those messages in the conversation first before I get to the very last, most recent message. Contrast that to Facebook’s conversational grouping and they are OK because they sort the recency of messages differently.
Which gets me to what I did next after I rolled back to OSX Snow Leopard. Fearing that my rollback was also corrupted, I ran it for about a week now but storing all changed files on Dropbox and only using the browser for email to minimize changes on the hard drive in case I had to start over again. It was also a rare opportunity for me to really see if I could adapt to the Gmail interface because I was now not switching back and forth between Mac Mail and Gmail.
After 7 days, Gmail (and Yahoo! Mail!) still annoyed the heck out of me. But after 7 days, my Snow Leopard Mac seemed stable, and I got my old Mac Mail back minus their conversation grouping which was the annoying part of Gmail to me anyways and I didn’t miss it.
Here, Apple had an opportunity to leap email several levels and didn’t take it. They just made the app look a little different and added what Gmail was doing, which I annoys me when I use it. Really disappointing.
Now follows my wish list for what I want or need in email, but hasn’t been done yet or needs to be redone:
1. A better search.
Searching on Yahoo Mail is miserable. Searching on Gmail is pretty good which is to be expected from Google BUT is a poor solution for the original reason why I lost the email in the first place due to other UI problems. Searching on Mac Mail is pretty darn good but could use some tweaks.
What’s missing in search is the time element. Often I know that an email came yesterday but somehow I can’t find it. Can’t I filter by only showing results from yesterday? No – I gotta wade through all the other crap that gets returned from the search just to get the one I want.
I believe people naturally use time as a memory aid. Where did I put my keys? I go back in time, retracing my steps through the house, and find that left it on the table by the door and not in my usual place. Or I know he sent me an email right after our meeting….last Tuesday. So I go back to last Tuesday and find the email.
Some searches have advanced filtering but they are all inconsistent. If I search on my boss Elon in Mac Mail, I can only pick 2 choices of where to search (All Mailboxes and my current mailbox) and From, To, Subject, and Entire Message. What if I only want to see messages from Elon that are about one of my companies and not any others? Can’t do that. I start typing in the search box all that text and then select Entire Message and then I’ve got all sorts of random stuff showing up.
2. Taking huge blocks of email headers and using visual techniques to highlight or even remove them completely from view.
If we say that we like the email header view that’s been around since the dawn of internet time, then I think this could be optimized further. One of the big problems here is that there is huge information overload. Trying to find something in the clutter is super hard. Spam filters have tried to help somewhat, creative filters which dump certain emails to relevant folders is another.
But one thing I have not seen tried is using some visual technique to highlight or remove completely from view. Well, not completely true. When I search, I remove all the non-relevant results from view. OK one case. Read/unread is now a blue dot in Mac Mail although some mail readers using greying out. So maybe two. I think, though, we need more cases where filtering causes email to either drop back in visual hierarchy or completely disappear from view.
Take my time example. Why can’t I select only show me email from Tuesday? Then all other email would disappear and only Tuesday email would be shown? Or show me only email from my boss Elon. I can sort the column, but then I see everyone elses email also cluttering up my view. I can search, but I get every mention of Elon in every field of the email.
Even if this was to visually set back every email that was an advertising email, and bring to the foreground emails from real people – that would be valuable. Now why wouldn’t I want to remove them? Because I’m a shopper and I still want to see some deal emails and not just see them completely. This is why I always go through my junk folder. Who knows what my computer decided to mark as spam? It makes a ton of mistakes.
3. Despite my lack of love for conversations, their OSX Lion Mac Mail visual implementation of conversations is pretty good.
I like how you can just scroll and then you can see conversations, each in its own block. This part I love. On Gmail, they are hidden behind each other once you’ve read them – now I can’t scan them! I have to manually open them all up to refresh my memory on the thread.
I also hate sorting by header to see if the subject can generate conversations. That doesn’t work. I’d love to see this combined with visual techniques to drop back other emails or remove them entirely from view, so you ONLY see emails from this thread and conversation.
4. Search by attachment media type.
Why can’t I view all emails with pictures attached? Or PDFs? Or Excel docs, Word docs, etc.? If it’s all pictures, then why not show them in a UX conducive to that media type, like in a slideshow or grid metaphor, or for docs I have a swipe-able (or equivalent) way of going through them quickly, and then also being able to easily return back to the email that it was attached to.
5. View by calendar.
OK back to my comments on time. Time can also be expressed as a calendar, as a grid with days of the week for any month or similar. If it’s a monthly grid, then I can just pick on it and see only emails that came for that day. It could even have a cool graphical representation that abstracts the number of emails that came in on that day, or some other summary information like 3000 emails, 30 attachments, 12 pictures, etc. If it’s zoomed in to a weekly via with 7 days, maybe the graphical view abstracts in more detail, like showing me a bar graph of emails that came in at each block of time. I could click on one of those blocks, and then it would show me all the emails that came in within, say, that hour. There would also be easy nav to jump to the next hour.
6. Better personal information tool integration.
My Mac Mail is always open. I have often written notes, keep key information like lists of designers I’ve worked with, and even written whole blog posts in draft emails. On the Mac, I don’t really have a good place to take notes. I’d have to start using Evernote to really get some power but that is a separate thing. And Word just blows for that. Every time MSFT releases a new Word version, it takes that much longer to launch. Sucks!
Maybe notes can be treated like Mail that you never send – you just can file them away, you can search on them, attach them to calendar events, or associate them with emails.
Scheduling often comes with an attached invite.ics which, upon clicking, opens up my calendar and presents the opportunity to reply to the invite. At least on the iPhone, Mail has some nice features where you can auto-create calendar events and the iPhone is smart enough to link some text that seem like dates. But I want more than that. When I create a calendar event, I want it linked back to the email that created it, and I want that email accessible so that when the day of the meeting comes, I can quickly go back and review the purpose of the meeting before the meeting starts.
And I want to only see that as a self contained context; don’t show me all the other crap around it. Just show me the emails associated with that calendar event and that’s it.
7. Better view by person, and info about that person.
Again, email UIs fail here. You sort in the sender column and then try to find the send there. Man that sucks. Try doing that in Yahoo Mail when your inbox is huge. Their paging eventually stopped working for me.
I should have a way of searching by person, and then having all the time and visual filtering that I have, only I’m acting only on one person’s emails with me.
It would be nice to be able to pull up additional info about someone, especially those I don’t know. I think this is potentially a more advanced business CRM function than for personal use.
8. Better integration with address book.
Mac Mail’s integration with Address Book is pretty good. But it could be better. When I find a contact, I want to be able to easily get to all meetings and emails with this person, perhaps even getting back to the first email or email introduction I had with this person. Right now, when I meet someone new, I always type it in the notes. This is because later, I often forget the person, but I remember I met that person through another person. I search on my friend’s name and pull him up because I put that in the notes field.
9. Search the SPAM folder.
This is so simple but ignored. Why can’t I search my Spam folder too? At least once a week I always open up my Spam folder because I don’t trust the filter to grab and hide stuff I wanted to see. I have to remind myself to do it regularly because there are always emails that get stuffed in there that I want. And it seems that even if I say this is not spam, eventually they get caught again. What’s up with that? Woe be to the guy who has a new domain; he’ll get tossed in there for sure. Or woe to me for starting a new business with a new name; I have to prove to the spam filters out there that I’m not spam.
10. Better Spam filtering.
No matter what we do, Spam manages to always get through. And non-Spam seems to get caught also. Somebody needs to do this better.
11. Local and location integration.
Everyone else is doing location based services, so why not email? If I knew where an email was sent, that would enhance searching a great deal. Sometimes I remember where I sent an email, as a way to find an old email. Perhaps I was on a business trip in NYC, or at a conference. Speaking of conferences, if I was emailed from someone I didn’t recognize and I looked up from where and saw it was at a conference that I was at, it could help jog my memory of who this person was and why he was contacting me.
What other innovations on email are out there? Here are two I recently encountered:
LookAcross – magically, they are able to determine when someone is most likely to respond to various communication modes, like email!
Tout App – templated emails, email management and analytics, plus connection with CRMs.
There is a plethora of email clients on Wikipedia but seems like the dominant ones are the ones we all know and love according to this report from Campaign Monitor.
Anything else interesting out there?
In any case, history has shown that email is hard to create to a successful separate business out of. This is why my disappointment with Apple was so acute; they had the chance to release something really innovative with Mail and didn’t do it, AND didn’t need to worry about survival as a startup.
In the meantime, I will have my decades old, time sorted, header interface that I’ve come to know, love, and hate….

Frequency of Product Usage in Startup Strategy

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I just read Mark Hendrickson’s post-mortem for Plancast on Techcrunch and the section on sharing frequency hit a chord.
When I meet startups, I mentally run their product or service through this test, which is the test of frequency of product usage by their customers. Simply put, if the frequency is high, then their product idea stands a greater chance of surviving in the marketplace. If the frequency is low, then the probability of dying is much much higher.
What do I mean by frequency of product usage?
When a user uses a product tens or hundreds of times a day, this is the dream – to work on a product that is so necessary by a large customer base that they need to use it that much! An example of this would be email – too bad it was created and set free to the world because someone could have made a lot of money on that, or at least in the early days.
Once a day is not bad either. Once every few days still OK. I read the New York Times email digest and website once a day generally, so I can remember to go there. What about the other news sites? Hard for me to remember which ones I do read when I visit them so infrequently.
Once a week – hmmm – getting to that limit. Once every 2 or more weeks and I think you’re in trouble.
That’s because people forget very easily what services and products they use, especially in this crowded world of me-too products. When your memory is sketchy, it’s easy for someone else to hop in there and supplant you.
Take travel services for example. How often do people really go on vacation? Normals tend to go maybe once a year, if that. If I find your site, use it to plan a vacation, and don’t worry about going on vacation until next year, do you think I would remember to come back to you? If you’re a startup, the odds are against you that you’ll even be alive by then.
This goes for both consumers or enterprise customers – if a business customer doesn’t find a daily or constant use for your product, then how can it find some justification for buying your service?
That doesn’t mean that what you’re working on shouldn’t exist, or couldn’t become a big business. The big problem is that you’re a startup with limited resources and survivability and some lower frequency services should really be done by more established companies. You, on the other hand, need traction and revenue as fast as possible before you run out of money. This is why frequency of usage is critical at early stage; if you have a product that people only occasionally want or want at special situations, you’ll never be able to build enough customers before you die.
So you have three choices. Either you must work on something that has a high frequency of usage, enough to attract users who find you useful enough to use often enough to keep coming back; OR you must find a way to buckle down and exist long enough for enough customers to sign up and generate enough traction and revenue for you to survive as a company. There is one other possibility and that is to add some high frequency elements to your low frequency of usage service to keep interest in and around your main service, despite the fact they may actually use the main service only intermittently.
Any of these could work and convince me to invest but working only on a low frequency of usage service in today’s super crowded marketplace definitely will not.

Stop Showing Product Screen Shots at Board Meetings

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This week I went to a board meeting. It was one of the best board meetings I’ve been to in a while because it was organized, efficient, and it went fast – about 1.5 hours. We talked about the important high level strategic things we needed to talk about, set actions, scheduled our next board meeting and adjourned.
I thought back over the last year about the many other board meetings I’ve attended. I thought about why some of them took much longer than 1.5 hours and seemed to drag on and on. One thing I could think of that did stand out was the presentation of product screen shots and the subsequent discussion about the product.
Now I’m not against all discussion of products in the board meeting. You should present the product development pipeline over the next few months or quarters. You can give an overview of the important major products, features, and services you’ll be launching (or killing). You can talk about holes in your offering and what competitors are doing that you are not and to have board level approval of a given direction.
But almost always, what derails a board meeting for some lengthy period of time has been the presentation of a product, some deeper dive into features, and the dreaded product screen shots throughout.
When this happens, then the comments come out. And ideas. Lots of them. Innovative ones, some good, some terrible. Everyone wants to chime in and make the product better. They start commenting on the design – the colors, the interface, the copy – everything.
Why not? It’s up there on the wall projected for all to see.
Is this bad?
At a high level, no. We should have these discussions about the product. They should involve all the important people they should.
But I would argue that this should not happen at a board meeting.
Board meetings are time to touch on all the major strategic, high level initiatives of the company. It provides oversight and governance, and drives the strategic direction of the company. You get a lot of experienced people in the room who have run companies before and they tell you where you are doing well, where you are doing better, and where you are heading towards danger.
And you take care of board level business like approving acquisitions, key hires, option grants, etc.
I just don’t think a board meeting is where you’d want to also have a big product discussion.
Then everyone jumps into the fray, and these discussions go every which way. The discussion is good, but the clock is ticking. All the while I’m glancing at my watch wondering when we’re going to get back to the main agenda since we’re off on a tangent now and have no idea when we’re getting back on track.
Eventually we do, but now a 1.5 hour board meeting has turned into a 3 hour affair. I look back and always note that if we didn’t have that product deep dive and discussion, this meeting would have been less than 2 hours.
There is a time and place for product reviews and discussions. Let’s schedule a separate meeting to do a focused presentation on it. We can ask for specific feedback, ask people to try it out, present research and findings on why we’re doing things a certain way or not.
Board meetings just aren’t the time to do this. Every time, inevitably the board meeting drifts and valuable time is used up when it shouldn’t be. So please, let’s just let board meetings be board meetings, and if you want to have a great product review, let’s set up a separate meeting for that where we can be prepared and have a great focused discussion on it, and not waste valuble board meeting time with it.

Fund Raising is a Necessary Evil, A Rite of Passage

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As I’ve said before, ABR. Always be fund raising. It’s just a part of your ongoing activities as a founder. Sure, you might not like it. It might not seem ‘core’ to your business success. It is. Building a business is not about only building a product and seeing if customers like it. You can’t just do those things in business that you enjoy. Make fund raising a habit. Don’t only engage every 18 months.
– How to Develop Your Fund Raising Strategy by Mark Suster
Every year, I meet entrepreneurs who say they hate fund raising. They don’t want to do it, they want to get it over with, they wish they could go back and build their business, doing the coding/designing/etc.
I hate it when they say that.
Fund raising is a necessary evil. YOU MUST DO IT. Without it, your company can’t survive. You need the money to get to the next level.
But I hear that nobody wants to do it.
Yes it sucks. Begging for money sucks. From the first time you begged your mom for money to buy that comic book to now when your begging investors for money, it still sucks.
I’m sorry but I’m tired of hearing it. As Mark Suster says in that quote from his latest blog post, it is something every founder needs to do and do well. If you aren’t good at it, then there is no better time to start learning how to do it then when you’re raising money for your startup.
It never stops. It seems like it does, but as Mark points out, it really never stops. As a founder, you are always out there selling yourself and your company. You need to start building these relationships early, as soon as possible after raising your first round. Big money is best gotten through familiarity over time, not social proof, not a quick glance at a deck, not an emotional reaction to the coolness of your screen shots. So you better get good at selling yourself so that you can get needed money later when you need it.
Raising money is a rite of passage to being a real entrepreneur. Yes it’s uncomfortable. Yes it seems like it wastes your time. But it IS a big part of building any business.
So get over it. Get comfortable with it. Use this time to figure out how to sell your startup and get people to invest in you and your venture. Go out and raise your round whether it takes 1 week or 12 months and stop complaining about how much it sucks. The future is filled with things you’ll have to do for your startup that suck – you need to get used to doing things that you don’t like and get good at all of them if you’re going to excel as an entrepreneur.

Envisioning the Future by Expanding One’s Horizons or VCs Should Read Sci-Fi

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Today, Brad Feld tweeted this great post about science fiction and its role in prediction and driving the future.

In a roundabout way, it took me back to grad school at Stanford in 1989 when I was working on my Masters in Product Design, before the department officially became the d.school.
It was when I first heard someone (my graphic arts professor Matt Kahn) say that designers need to travel more in order to broaden their horizons and in increasing their worldliness and knowledge, they could create better designs and become better designers.
Back then, I wasn’t very worldly. I didn’t care much for traveling or seeing other places. I was from Poughkeepsie, NY and led a pretty sheltered, enclosed life. I hadn’t traveled much as a kid and didn’t really understand why I might want to travel other than to hang out on a beach. Besides, it cost money which I didn’t have at the time.
Time went on, and I got the opportunity to travel more, and slowly but surely seeing other cultures and meeting the people in their broadened my perspective greatly as it related to design. Somehow the expansion of consciousness made me more effective as a designer.
After that, I sought to learn about as much about the world as possible in all aspects. I read everything. I devoured books and magazines on not only design but technology as well. Later, I expanded this to all sorts of topics, ranging from news to economics to everything. I knew enough about a lot of things to be dangerous but it was extremely effective for making me a better designer (and also helped me to be a better conversationalist!).
Which brings me back to science fiction.
Before my consciousness expanding realization, I have always read a lot. But that was limited to almost exclusively science fiction. But now my science fiction reading had another benefit.
As Cory Doctorow wrote in his post, A Vocabulary for Speaking about the Future, science fiction authors are great at painting pictures of the future. Perhaps they are terrible at predicting what the future really might bring; still, they are great at showing us what the future could potentially hold and thus can be extremely useful in expanding our consciousness for creativity in design…or in venture capital.
VCs need to have some intuition about how the world will be in the future as they are betting on things now that will hopefully be big later. In order to do that, you have to be creative and imaginative; you can’t analyze what the future brings – look at how Wall Street experts did back in 2010 predicting what would happen in 2011. You can only imagine what the world will be like and then make your bet.
To beef up your intuition, you need to expand your consciousness through travel and experiencing other peoples and cultures and expand your knowledge base to cut across as many disciplines as you can handle. In doing so, you will release all the negativity that only comes with analysis of the future which is unknown and can’t really be analyzed. And what better way to increase your creativity of vision of the future than to have people lay it out for you in the form of novels and short stories?