Yearly Archives: 2007

Investor Fatigue?

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The last half of 2007 saw for me an acceleration of deal flow. I’ve spent numerous hours with a host of startups. I’ve passed on a few, gotten further with others. Most I’ve not gotten involved with, and the remaining few I’ve stuck with them through the process and told them verbally that I was committed, as long as other things fall into place.
Some of these deals have taken a long time to close on investment, or finalize my involvement. I find that as the weeks become months, that I am feeling a bit of fatigue on these deals.
I have heard this happening to other entrepreneurs where if they take too long, their investors just lose interest and don’t want to do the deal any more, or just move on to other projects which are taking up their time. Now that I am toe-ing the edge of this fatigue on deals, I can relate to how these investors feel.
As an investor, I told myself I would not be flaky. When I say I am committed, I want to be just that and not be wishy-washy. I do not want to frustrate entrepreneurs and make them do extra work in chasing down investors who can’t figure out if they want to do the deal or not but just stay in that grey zone; I want them to finish the fund raising part of their company building and move back into building the product and business. I have heard too many stories about investors who can’t seem to just make a decision to say yes or no and don’t want to be like that.
But now I feel some fatigue setting in, and start to ponder not just the fatigue aspects but also the reasons why it’s taking so long.
We investors tend to like to pool our due diligence process by watching the reactions and analyses of other investors. So if an entrepreneur can’t get the commitment of prominent investors in a short amount of time, then perhaps that is saying something about the project itself. Perhaps something is amiss; perhaps the entrepreneur’s pitching skills need work, or the pitch itself needs re-work, or the business plan itself. Add to that other projects demanding my attention – I cannot help but feel that fatigue may actually pull myself out of commitment on certain projects due to my own wavering interest, but also the real reasons why it’s taking so long to close on an investment round.
Now that I am experiencing this time lengthening process firsthand, coupled with my own fatigue on projects, I offer this advice to entrepreneurs, which is to close on investment as soon as possible, doing whatever it takes to prepare, make a great pitch, and herd the investments to a close date.
It’s a bit like dating; if I go out with a girl many times and it doesn’t seem to go anywhere, shouldn’t I stop wasting time and move on to someone with whom a great relationship would develop?

Betaworks in New Office 12-20-07

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I just got involved with a new venture called betaworks out of NYC. It’s a new business creation platform which hopes to serve the east coast market for socially driven early stage internet startups, with close ties to the west coast. We just moved into our official first location with Daylife:



I’m excited to be part of this team. We’ve brought together a group of people with wide variety of experiences and are working through our operational details now.

Analyzing Myself Into Ultra-Conservatism and Inaction

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So far, I’ve spent a little over a year angel investing. I’ve noted before that it’s been a fun and rewarding educational process in learning how to angel invest. I’ve talked to people and got some great pointers, read some books on the subject, read some insightful blog posts, and leveraged my own Yahoo! knowledge in trying to figure out whether I should invest in a business or not.
I’ve also noticed that I’ve begun, and now attempting to prevent, a slow slide into “analysis ultra-conservatism.” What exactly is this?
Just recently, I’ve started looking at a lot of deals and but invested in none. I felt like the frequency of my investments has dropped dramatically. Yes, there were many reasons why I did not invest and some of them were out of my control. But I also wondered if something else was at work.
As an angel investor in early stage internet companies, I know that high risk is part of the game. They all have not been in business long enough to show traction, and you need a healthy dose of faith in order to put money in them. Yet, I felt that I was thinking more deeply into a business now than I did before. For sure, I have more knowledge now; I have looked at a lot of companies, heard other peoples’ objections and analysis, developed my own analysis process in what I like and don’t like. It has definitely moved from an emphasis on liking the product and the team to many other business aspects. This is all good and makes me more seasoned. The bad thing is that the more knowledge I get, the more things I find wrong about a business and shy away from investing.
So, as your knowledge and experience grows, you get better at analyzing companies but as you get better at analysis, the list of problems grows and you start finding reasons to not invest, hence, the term “analysis ultra-conservatism.”
A friend of mine once said something very insightful about early stage investing, which is:
There is always something f**cked up about EVERY early stage startup.
I find myself repeating this to myself over and over as I do not want to fall into the trap of “analysis ultra-conservatism.” I cannot remain an early stage investor if I do. I know that it is a good thing to get more experience in analyzing companies and opportunities, but I have to remember my friend’s insightful quote and stop myself from over-analyzing and becoming risk averse simply because an opportunity has faults in it. ALL EARLY STAGE OPPORTUNITIES HAVE FAULTS! I must remember to keep in mind that there will be faults and to decide on the positive factors that remain.

One MEEEELLEEEEE-UN Miles

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About a month or so back, I get this message that I just joined the Million Mile Club for American Airlines.
ONE FRICKIN’ MILLION MILES!
My butt has sat in AA plane seats for one million miles since I started flying AA as a kid to today.
On one level, I’m happy about it. I got this little icon on my Exec Platinum card that says 1 Million Miles, and I get lifetime Gold status.
On the other hand, I’m not so sure.
ONE FRICKIN’ MILLION MILES!!!!
One million miles of sitting in back wrenching, trapezoid tightening, swollen leg plane seats whose failing cushions and poor ergonomics challenge any sane person while propping up the chiropractic and inflatable pillow business. One million miles of sitting in seats designed twenty years ago when humans were of smaller stature and now through trans-fat fast food and working out humans are just that much bigger. One million miles of watching security getting beefed up to the point where we’ll have to strip naked soon to get on the plane.
And how many hours spent just sitting in airports waiting…and waiting…and waiting….
But yet, the world is truly smaller. Decades ago, the expense and difficulty of flying made the world seem so much less accessible. Today, I think nothing of hopping on a plane to go to another country, or just cross-US to do some business or visit family or friends. So one million miles of growing, mounting discomfort for one million miles of watching the world grow smaller, more accessible, and less lonely.
To me, this is a potential positive balancing act turned a zero sum game. If we improve all the crappy things about flying, the positives are actually pretty compelling. But no, we get benefits and sacrifice other things for it. It’s really a shame.

It Sucks to Not Be an Engineer…

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It’s gotten pretty clear to me that if you’re not an engineer, then starting a new Internet startup becomes a difficult venture.
Consider the non-engineers out there with great ideas. You want to start a company but haven’t been able to convince someone that you have a great idea through Powerpoint alone. Everyone wants to see something working so they can wrap their brains around it and see if it is truly viable. But you can’t show them anything. So you go try to build it.
So far it becomes an expensive project…well, in Web 2.0 terms it’s expensive. In normal terms, it probably costs what it should cost. You go find some money, and you pay people what they need to get paid and whatever you build gets built.
But not so in the world of Web 2.0. It turns out that full on products can be built for so much less than normal. Well…less than normal if you are an engineer and program it up yourself. You are programmer, product manager, visionary, business development, designer all rolled up in one. You spend a few months coding at night after your day job and, poof, you have a working web site. The only expenses you may have are your own; nobody else needs to get paid.
For non-engineers, it’s a tough to build a Web 2.0 company without being an engineer, or having one as a partner. You could hire an outsourced engineering firm but that could run your costs up to $30k to $100k per month for many months. You could raise that but you’d need 6-12 months to build something. That would put your angel raise at the very high bounds of what is achievable with a Web 2.0 concept. And you’d have to do it without a working prototype. Makes it that much more difficult as investors know they should see something first and have gotten spoiled by all the other Web 2.0 companies who do come in to present a concept with working prototype in hand.
Best bet: Find an engineer or two and bring them on board with your concept. Without engineers, it’s a long hard road and I’ve already encountered several entrepreneurs who are trying to start something, as well as those who are well along the way. Those who have built something could only get money from friends and family, so having rich friends and family goes a long way. Very few have gotten money from a fund, and those were people who had track records in entrepreneurship, experienced and persuasive in the pitch, and had all the important questions answered.
Second best bet: buy Ruby on Rails for Dummies and start programming.

Increasing Site and Social Engagement in Detail

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Over the last few years, social media has really become a popular buzzword. People talk about social networks and the importance of implementing them, as well as the drawbacks and potential dangers. Rather than talk about social media as a strategy, I wanted to point out some actual detail level things to try rather than stay at the 10,000 foot level of discussion. Based on working on social media projects over the last year, I have found the following techniques to be effective at creating and maintaining a vibrant social environment that produces results:
Voyeurism
Related to: Dating/Hooking Up, Expression (receiving end of)
People love to follow other people for a variety of reasons. From telescopes in apartments buildings to eavesdropping on a nearby conversation to hearing and passing on gossip, the lives of others around us seem infinitely more interesting than our own. We follow other people for many reasons: to keep up with what our friends are doing, to check out hot women, to see what trouble celebrities get into – we are always curious, sometimes to the point of obsession, about what other people do day to day. Successful social networks allow people to post and describe their daily lives so that others can take a look.
Communication
Related to: Dating/Hooking Up, Connecting with Context, Entertainment, Validation
It is human to want to contact someone else. We are social creatures and we want to talk to others. Providing a way for people to contact and maintain communication with others is crucial to the lifeblood of a good social network. Just as important is the ability to shut people out, and give people ways of *not* talking to everyone or only certain people (ie. annoying people, spam, ex-boyfriend).
Dating/Hooking Up
Related to: Voyeurism, Communication, Masquerade, Entertainment
Let’s face it. Lots of guys surf pictures just to check out hot women. But then sometimes you’ll want to make contact and see if you can get a date. Simply providing a means for surfing photos in profiles and a system for communication can enable this activity, but providing additional functionality to facilitate this activity can make the experience more enticing and fun. Think HotOrNot.com and the ability to rate people, and then pick out only the HOT rated people to contact, or show interest by sending someone a virtual flower. Or I’m In Like With You where auctions meets dating and you bid on the ability to meet someone.
Entertainment
Related to: Communication, Dating/Hooking Up, Competition, Fame
Having a good time on a site increases engagement. Providing ways of having fun keeps people coming back to have more fun. Games are the obvious one, and playing by yourself is good but playing against others is often better. Sometimes it’s the content posted by users, like funny videos of themselves posted on YouTube or pictures on Flickr to be watched on their Flickr streams. Or if a fun spin can be put on mundane activities, then the unique fun that activity brings will draw people in and keep them interested.
Fame
Related to: Competition, Expression, Entertainment, Showing Off/Vanity, Validation
It’s fun to do an activity and play a game, but enabling a way for people to get acknowledged and recognized for their skill rewards people by the notoriety they get for being good at something. Leaderboards on gaming sites allow users to show the world that they are #1 in a game, and they’ll screen shot that and put it on their blog. It also means that they’ll keep coming back to keep achieving or maintain their #1 position on the leaderboard for bragging rights.
Competition
Related to: Fame, Entertainment
There is something in the act of striving against other humans that people love. They want to test their ablities and measure themselves against others and be measured and will keep coming back to try. They like to see continual improvement and enjoy a rise in skill. There is also competition against themselves so it’s not always about other people. And, there is the ultimate prize of being number ONE. Perhaps we’ll never get there, but maybe we will. No matter what, we love the struggle and the journey to number ONE. In games and sports is where we most often see competition, but it can also be other things like getting the most views on posted content like a video. Great games and activities constantly provide the ability to raise the bar just a little more each time to keep people competing, but don’t raise the bar too high or else people will give up. Not raising the bar at all will cause people to achieve that level and then move on because it’s too easy. This bar can be set by other users, like when you’re competing against other players in a sports game, it can be set by a computer which auto-adjusts for your skill level.
Expression
Related to: Fame, Voyeurism (contributing to), Showing Off/Vanity, Validation
Constantly we are on stage. The world is a theater and we are its actors. From the clothes we wear to what we say or do, we are always showing the world who we are. Providing a means for people to express who they are means they will continually do it, especially if there is a mechanism for validation like commenting on photos in Facebook.
Showing Off/Vanity
Related to: Expression, Fame
The extreme form of expression is showing off and trying to show that we are special and unique. Showing our crazy stunt videos, or photos of us drinking a 3 foot tall beer, or next to a movie star all show the world that we are not boring people but that we have the biggest peacock feathers. Allowing people to show off and giving validation mechanisms like commenting on photos, or leaderboards, or graphical badges of honors on our profile pages reward us for posting and showing off, and encourages us to do more.
Validation
Related to: Communication, Fame, Expression
We always want to know that who we are is noticed and special by others. We like it when we get comments on our photos and videos from our friends. It makes us feel that others care and that we are not alone in the world. Implementing means of giving validation gives users that special feeling that others do notice them, and they’ll keep on posting to get more validation. The simplest form is commenting on photos and videos, but it can be focused by providing context like on Dailystrength.org where you can post an issue and get support from strangers and friends via the internet.
Masquerade
Related to: Communication, Community
Sometimes we’re boring. Our lives are so mundane that we get sick of it. Or maybe we’re not in the social mainstream. We feel shunned by the general masses and can’t seem to get in the flow of society. Or maybe we’re just tired of being ourselves and want to try being someone else. On the internet, the ability to be someone else is very easy. Simply creating a new screen name and building a personality underneath it has been done since the early days of the internet. People can pretend they are the opposite sex, older or younger, more fun, more engaging – whatever. It is something that is not easily achieved in the real world. Acting out the fantasy that they have either personality traits not in the real world or entirely someone else can be an activity that keeps people returning. The unfortunate thing is that people often masquerade for negative reasons like stalking children, and this needs to be guarded against.
Community
Related to: Masquerade, Connecting with Context, Communication
Humans want to belong. It’s often to easy to feel outcast in the real world. On the internet, communities can be more accepting of people than in the real world. If a site can create a means for people to be a part of something, they will want to come back and continue to participate to be part of that community. Think of the instant groups that Facebook has, based on tags created from your interests, or your hometown. These are ways for people to find commonalities on which to connect on, which foster communication and validation.
Connecting with Context
Related to: Community, Communication
In watching social networks over the years, I am a firm believer that social networking for social networking’s sake is a path to declining activity. It is much more engaging for users when you create a context for which socializing happens. MySpace’s usage came from the fact that they were always about promoting indie music. Yes, other things happened there, but you knew that you could always find indie music on MySpace. Facebook started out by being exclusive to colleges and there was no way to taint the population with random people who were not attending your university. Everyone you found there went to your college and you could relate easily. LinkedIn’s network is built on professional networking, another popular activity in business and its functionality is focused on making that activity easier. Contrast that with Friendster, who had a meteoric rise when it first came out and then usage tapered and dropped because people got bored there when applying this list of social techniques was not done well or not at all.
For all my projects, I try to think about applying some or all of these techniques in creative ways. I also think about the context since not all techniques are effective in every context. For example, dating could be a hard sell in a social stock picking application, but competition and fame would definitely work well. Some of it is experimental, as there could be unexpected results of applying something you thought wouldn’t work in a context. So let’s turn my example around. Suppose you did create a social stock picking site which had an underlying dating application underneath? Perhaps it could link up all the superficial, money hungry people by allowing you to find, meet, and date the richest, best stock pickers in the world…? Socially unacceptable? Perhaps. Successful? Who knows…

Outspark Explosion 9-27-07

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I was over at Outspark the other day and was floored by their growth. Back in February, they were still just filling out their space with IKEA furniture:

When I walked in this last Thursday, about 7 months later…

What amazing growth after only 7 months. They are moving like gangbusters on their game platform and watch for cool things to come soon!

The Anti-Digital

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I admit it. I’m totally digital. Wired to the hilt. Can’t live without it.
Well, almost not. I force myself to be totally digital because it’s my job to know and experience what it is like to be totally digital. It makes me more effective in designing products and services for the next digital generation. I suppose I could live being NOT so digital, but I want to be better at my work so I be more digital than not.
In being so digital, it’s strange, funny, and sometimes frustrating when I encounter what I call “The Anti-Digital.” These are people and places which abhor having digital stuff around for one reason or another.
Take Cafe Dante in the West Village of Manhattan. Here is the sign right at the door when you enter:

Cafe Dante is a quaint cafe that serves old school espressos and eats and if it’s hot, you can always get a refreshing dish of gelato there. I like hanging out there because it isn’t as contrived as Starbucks, and it’s quiet so that you can enjoy a conversation with whomever you’re with.
But NO LAPTOPS ALLOWED. They don’t even like you talking on the cellphone with somebody. To preserve their atmosphere of being an old school, they don’t want people hanging around all day typing on laptops, even if it could mean that they get more business from the constant flow of caffeine to people typing on laptops. They just want you to have a great old fashioned conversation and enjoy a cup of coffee with your buddy or date.
Then there are “anti-digital” people. These are people that are barely can manage having a cellphone, and just don’t find value in being connected. They have email addresses but rarely think about looking on their laptops to check for email. They never buy gadgets and almost always sit in the follower part of an adoption curve, after a technology becomes so commonplace that they can’t avoid it.
One person I know at least checks email somewhat regularly, but takes forever to reply. I know this, so I rarely send emails but call instead. This person has also left their cellphone at their summer home for weeks and didn’t even bat an eyelash! Most of us would freak out if we lost or left our cellphone somewhere and could not live without it. This person just calmly told me that if someone wanted to find them, they would know how to do it. The cellphone is an afterthought in any case; most of us could not leave home without filling our pockets with our gadgets. But even when this person had a cellphone around, it would often be forgotten and left at home, or not turned on, or even left to completely be drained of power and not recharged.
Another person I know does have a cellphone, but practically never turns on their laptop. In this case, forget even sending emails to their email address; it won’t get read. But at least the cellphone is always on their person. So I must either text or email to the cellphone in order to get in contact. Otherwise, forget about websites; an iPod is barely manageable (it’s probably the worst looking, scratched up, dented iPod I’ve ever seen), and the most advanced gadget in their home is a Tivo without which shows would be missed.
To both people, there is no Facebook, no Youtube. Digital cameras get used, cellphones maybe, laptops aren’t a necessity.
When places are “anti-digital”, I’m sometimes OK with it. I seek them out to either have a decent conversation or just to get some quiet and think to myself, or perhaps read a book. Other times I can’t go there because I do need WIFI and I want to get some work done and need to be online. “Anti-digital” places don’t fit in that.
As for “anti-digital” people, this is where it is most frustrating. I’ve either developed more efficient ways of communicating or get used to communicating to the majority of people I connect with through technology. I always have to shift my normal way of communicating to another way just to get hold of these people, which is often back to some old way like picking up the phone, and that’s annoying to make that shift when you’re trying to get a lot done fast.
Is my life better being maxed out digitally or is it better being “anti-digital”? I think it’s a personal choice and a challenge. Personal choice in being maxed out digitally because I am an early adopter, and it’s important for my work, and because I have a natural curiosity about technology. A challenge in that I am a big believer in simplifing my life and while you could simplify by dropping all this digital craziness, I am a big believer that we’re going to have to live with technology and we must challenge ourselves to simplify in the face of more technology rather than less.

Facebook Messaging vs. Old School Email Part II

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Following on my last post about Facebook messaging…
Today I exchanged Facebook messages with someone. I connected this person via traditional email (via his last known email address that I had for him) with some folks. It was an urgent communication, so I immediately logged onto Facebook and sent him a Facebook message telling him that he had an email waiting for him, so that he could respond quickly.
Isn’t it funny that since I had not corresponded with this person for a while via traditional email but rather Facebook messaging, that I would tell him he had a traditional email waiting for him via Facebook?
As soon as I clicked on the Send button in Facebook, I paused and thought that I should check out where his notifications (that he got a Facebook message) were going. When I looked, they were going to same place that I had sent a traditional email to him!
Facebook…Email….Facebook…Email…?

Facebook Messaging vs. Old School Email

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One thing I heard about the young generation is that they never use email anymore. I began to wonder why that was, where corporate America and us old folks who grew up with nothing but email couldn’t live without email now.
Lately, I started trading messages with people on Facebook through their messaging system. I wasn’t sure what to make of it at first. Some people began sending me messages while I would initiate some just for kicks. It seemed like a novelty more than something that was useful.
But I started recognizing the advantages of messaging like this:
1. Email is filled with spam. Yet, Facebook messaging is not. I guess spammers haven’t figured out good ways of getting into the messaging system. Each time you create an identity on Facebook, there are verification steps to show that you are a real person. Once someone creates a fake identity for spam purposes, it’s pretty obvious, even if you get past the verification steps. They often have a big link posted to their website and I immediately report them as inappropriate to Facebook authorities. I once met Jonathan Abrams, founder of Friendster, who tossed out the idea of using a social network as an email system, because it would effectively eliminate spam. I think he was right.
2. It sorts emails by the conversation. It presents each message thread, which is incredibly useful from a conversation standpoint. In Outlook and other email programs, somehow the sorting by sender or subject doesn’t solve the entire problem. It doesn’t do auto-grouping by conversation, which I am finding to be very useful in a Facebook GUI; subject sorting just doesn’t cut it. And last, threading never seems to work well, because sometimes attempting to derive threading via the RE: of a message subject can be daunting, especially if it has been editted.
3. Going further, the presentation of each conversation once you click into it is very nice. There is no antiquated ‘>>’ for presenting the previous body of the message into replied email, which can make for difficult reading. You can see the whole thread at once and see where people replied. I do wish I had the option of copying some of the previous message into my current message. Sometimes there are multiple points in a message and you want to reply to each one separately and clearly. I have cut-pasted message sections into a new message and then typed a reply to that, just so the recipient knew I was talking about that section of a message and not another part.
4. If you want to start a new topic, you can just start a new message thread. This helps keep conversations organized instead of devolving from the original message where you may forget to change the message subject or just too lazy to, and then the conversation starts going every which way.
4. You can only receive messages from friends. Thus, you have already designated a list of safe message senders, which along with item 1. above helps to eliminate spam.
5. Private messaging is available, but you can also do public messaging. This is not available to the email world. Via the wall, you can have a more public conversation which can be entertaining and/or useful, if you intend on others to see it.
6. There are many types of communication happening on Facebook. People can comment on your photos, write on your wall, have activity and you get notified of it, and send you personal messages. Having all that accessible in one place is very useful. Otherwise, I’d have to flip between Outlook and several other websites to check activity. Sometimes I can send activity to my email, but then it just gets mixed in with all the other spam and normal important conversations I’m having. It’s not very optimal. On Facebook, the newsfeed gives it to me all and a light notification on the front page gathers for me all the communications one can have with their friends and community in one convenient place. It’s no wonder that people today have switched to Facebook from email as a primary communications vehicle.
The moment of epiphany for me happened when I began my Facebook messaging to friends AND I left a browser window up with Facebook in it. I would find myself hitting reload on that page many times during the day as well as checking on Facebook through my iPhone. I began to understand why today’s youth almost never use email and just use Facebook messaging.
As my usage of Facebook messaging grew, I could also see parallels with another project I’ve been deeply interested in, which is email innovation. Facebook messaging solves so many things that I hate about current email. But could email innovation just be a dying concept as email gets supplanted by Facebook messaging?
Four wishlist items for Facebook messaging:
1. Offline messaging.
2. Save messages and conversation threads on my hard drive.
3. SMS messaging.
4. File sending.
Still, I do not see myself totally removing myself from email. The corporate world, and most of my generation, still use email as a primary communication vehicle. But for a significant and growing population of people I associate with, Facebook will become my primary communications method with them.