Yearly Archives: 2007

Day 3 iPhone iPhrenzy: Figuring Out How I Will Use It

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My original thought regarding the iPhone was to somehow move completely over to the Mac. But I would definitely have to wait until Apple comes out with their much-rumored super-thin MacBook as I need to save my back from lugging laptop weight. I have a Sony T-series which seems to be the best option for lightweight computing so far. However, I will switch if Apple launches a super-thin option.
In any case, I wanted to see if I could remove one device somehow no matter what. Today, I carry a Motorola SLVR with iTunes, and a Treo 680. I do carry my iPod sometimes, but I’m not one of those people who walk around all day with earbuds in my ears, so I’m ok without music.
Comparing the Treo 680 to the iPhone has been interesting. Physically, the iPhone is much more thinner and sleek, and a joy to hold. The Treo 680 is bulky in comparison and seems so yesterday’s technology (it became “yesterday” on Friday when the iPhone launched!). However, I do like it for:
1. I am still faster on the Treo 680 keyboard. I seem to be getting better on the touchscreen keyboard of the iPhone, but the physical keys still are better.
2. I use the Treo 680 for typing out notes and the occasional blog entry. I sometimes use a folding IR keyboard which works really well if I am typing something long. Definitely Apple needs to enable Bluetooth keyboards at some point. That would really make the iPhone useful.
3. I use a program called InfoSafe which keeps all my passwords around securely. I would need to replace this if I were to get rid of my Treo 680.
4. All my silly games are still on the Treo 680. None available yet on the iPhone, but I am sure this will change soon.
So far, what I think about the iPhone:
1. I really like the touchscreen interface! I also love the interactions they put in there for scrolling and resizing.
2. It took me a while to figure out how to set things, which are located in Settings. However, some of it seems kind of dumbed down.
3. It seems to be able to open Word attachments and I haven’t tried PDFs yet. I would definitely love an industrial strength word processing program, spreadsheet, and presentation program as well, although maybe it can open them for viewing at least.
4. No MMS! I use my Motorola SLVR all the time to send occasional shots to family and friends, but can’t do that here! I hope this comes soon.
5. Email is a joy. IMAP for Yahoo! Mail really works well. I wish there was a way to mass delete emails. This could become a problem at some point for my POP accounts and overfilling my iPhone memory. I need to look at the docs to see if there is an auto-delete off the iPhone after some period of time.
6. The browser really ROCKS. It’s probably the main reason I bought it. I can now see web pages in their full glory. The browser on the Treo really blows. I’ve bought books on amazon.com, checked out netvibes, did google searches. It works really well!
7. The keyboard is a bit funky at first due to my right thumb’s touchpoint. For some reason, the pad of my thumb touches down on the screen at a point that is not where my brain expects. I am off by a key! So now I am training my brain to recognize that typing with my right thumb means I have to mentally adjust it slightly to the left in order to hit the right key.
8. No cut/copy and paste! How funny that is. I think this will prevent it from being an office replacement.
9. Syncing was amazingly easy. I love the fact that you didn’t have to screw around with installing conduits and seeing if you got it all right. You just launch iTunes and hit the sync button, and it just does the sync with Outlook. One strange thing. It doesn’t sync my notes into its notebook. How strange. But calendar and contacts come over just fine. I hope they add an update to make this happen. As you have guessed, I am syncing my iPhone with my PC for now for contacts and calendar, and I will load music from my Mac Mini.
10. By the way, I did figure out how to get music and other media synced. Just a few settings in the tabs of the iPhone area of iTunes. But it seems to only let you control syncing via playlists. I will look at this more.
11. WIFI!!!! I locked onto my house network and also to T-Mobile at Starbucks. Very nice! Power drain seems to be ok, and much better than my Treo 680 which probably would have cranked down pretty quick if I had tried to go WIFI continuously with an add-on card.
12. One ridiculous thing: I have all my contacts categorized in Outlook. Those categories have disappeared on the iPhone!
So far, the one limiting factor is MMS for it to replace my Motorola SLVR and being able to type long entries means I will want my Treo 680 around. I think I will carry iPhone around separately for a while and see what updates Apple has for it. It doesn’t work too well as a replacement for a laptop but is more of a hyper-powered mobile phone. Still, I think this device is hugely cool and Palm really missed the boat by not coming out with a Palm version super-thin phone. The Motorola Q and Samsung Blackjack are also nice, but Windows Mobile just kills both those devices.

Caught Up in the iPhone iPhrenzy

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Friday 6/29 finally arrives. The iPhone goes on sale! One of the most hyped up devices ever, I wondered if I was even going to be able to get one on the first day, but I sure as hell was going to try.
Tracking press releases up the big day helped strategize how I was going to get one of these babies. I originally thought I was going to head to a AT&T/Cingular store, but then I realized that you could get one at an Apple store. And how funny: you could only get one per customer at an AT&T/Cingular store, but you could get 2 per customer at an Apple Store. I theorized that they would probably have a lot more available at the Apple store so I made plans to get to the one at Valley Fair well before 6pm.
It was also a good thing; ever try to get anything at a AT&T/Cingular store? They have the worst checkout and queueing system ever. You go there and sometimes you just wait forever, because reps are sometimes trying to sign people up for an hour as people try to figure out what options they need. I can’t believe they haven’t figured this out.
Thanks to Apple for solving their problem. I found out on their website that you upgrade your iTunes and then when you sync your iPhone, it goes through the signup process in iTunes via the web. Wow. Thank god we could circumvent talking to some AT&T/Cingular rep about it!
So Friday turned out to be full of meetings. My last meeting I even cut short a bit, but the entrepreneurs I met with were thankfully sympathetic to my need to get an iPhone. I left around 5pm for Valley Fair and got there around 520p.
I went to the Apple store and found it to be closed! But, there was this huge line that wrapped around the side of the building, and then crossed through a doorway outside the mall. By the time I had gotten there, there were already about 300+ people in line! So I found the end of line and waited like everyone else.
As we’re waiting, a guy comes up and asks us if we want coffee. Leave it to Apple to serve the people in line some Starbucks coffee, iced or hot! I gratefully grab an iced coffee and sip it while playing with my Treo and taking occasional pictures (which I’ll post later).
I wonder about my Treo. In fact, I just bought a new one because my old Treo 680 was having problems. It’s pretty good, but if the iPhone lived up to its hype, I could potentially get rid of my Treo and my Motorola SLVR (with iTunes on it) as well!
6pm finally arrives and the line moves about a foot.
615pm: Somebody walks by the line and gives a loud rebel yell and says, “I GOT ONE WHOO HOO!” All of us look at each other in line and collectively we wish that somebody would mug him on the way to his car.
6:20pm: Two more people come out and give doomsday talk about the fact that there is no way we’re gonna get one. I don’t want to hear this.
6:30pm: I move 20 ft. Seems like we’re getting in the store now.
6:34pm: The line really starts moving now. Anticipation builds in me. I just hope people aren’t sitting around in the store wondering if they should get one or not.
6:45pm: I look behind me and see about 80+ people lined up. The after work crowd must be showing up now.
7:10pm: An Apple guy gives me a brochure about data plans. Unbelievably, data costs less for the iPhone than for my Treo. I love getting ripped off by the phone companies.
7:20pm: I make up to the doorway into the mall. There is a big, tough looking guy who only lets 20 people at a time into the doorway. In a few minutes, I am in the doorway and now walking down the hall to the mall! Yeah!
7:24pm: I drop into the line outside the Apple store. They let one person in for every person that leaves. It’s pretty funny. Every time somebody walks out with the distinctive iPhone bag, they clap and cheer! Ha. That’s what I would feel too if/when I got one.
7:34pm: I’m IN! Standing in this line that goes to the back of the store, an Apple guy asks me if I want to take a look at one. Shit yeah! I play with it and call on it to check out its voice quality. Wow. The hype is REAL. I love it love it love it.
7:40pm: I grab 2 8GB iPhones and pay for them, and I’m walking out of the store now, grinning like a cheshire cat. I swear, getting one of these is like waiting for concert tickets the day they go on sale!
The next morning, I boot up my Mac and download iTunes 7.3. I go through the signup process and notice that I can’t replace the SIM card, or at least I couldn’t find an easy way to do it. I was going to toss in my old SIM card but looks like they won’t let me. OK. So I signup for a new plan and will cancel my old plan later, as well as switch the phone number to it.
As I read the instruction manual, I find they did an incredible job with the syncing capabilities. I can, through iTunes, set it to sync with all the Mac apps, as well as Outlook on the PC! Pretty cool.
After I activate it, I play with the browsing and typing features. I setup email which is a bit weird, but I figure it out. Supposedly you can download the user manual off the website, but I haven’t been able to find it yet.
Web browsing is great. Now I can see web pages pretty much like they’re supposed to be, not all crappy like on my Treo browser. Email is also great. Using IMAP on Yahoo! Mail, it is really great for synchronizing email between client and iPhone. I also attach my DSV email too and will probably get my other email accounts attached too.
The one thing I could not figure out yet is how to get music on it. I try to drag/drop music onto the iPhone icon in iTunes but it doesn’t accept items that way. I’ll have to see how I can selectively add/delete music and videos to the iPhone a bit later.
All in all, this is the coolest device I’ve seen in a long time. A lot more compact than an iPod and certainly thinner than my fat Treo 680. I was afraid that it might be bulky in my pocket, but it definitely is not. Apple certainly has a winner here and it will be fun to see the rest of the industry just *try* to catch up.

Why and How Do Startups Move So Fast?

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The question of how do startups move so fast comes up surprisingly often. I finally gave it some thought, after the question came up again in a recent meeting with one of my companies. Over the last year or so of working with startups, I came up with some observations:
1. Small teams, 1-3 people. Makes sense right? Less time lost, less arguing, etc. Less meetings.
2. Everybody resonates with the idea and generally agrees with direction. Since everyone is either a participant or expert in the field in which the site is created for, then everyone does not need to learn but knows instinctively what to do. Nobody is working on a product that they do not use themselves. It’s a great way to find people like yourselves, when you recruit from the level of common interest in a certain product area.
NOTE: It’s really hard sometimes to get someone to resonate with your idea. You may hire them for their intrinsic talent, but it may be really difficult to get them to feel the instinctive bond with your product area.
Sometimes it’s impossible. Doesn’t mean that great work can’t get done, but it does mean a level of independence can’t be achieved, as non-resonating employees need more directional advice than those who do resonate.
3. Along with 1, the teams usually only consist of engineers cranking away. Most of them are multi-talented to a point, so they play multiple roles of programmer, GUI, html/css, product manager, product visionary.
4. Strangely enough, I have not found location to be a common factor for moving fast. Certainly it enhances the process, but a lot of teams are working with people remotely, since engrs are so hard to find and many just don’t want to move. Somehow, they have found ways of working together and can still make progress. Lots of travel involved and constant communication are two of many key points in making it work. If I get a chance, I’ll dig into it more with some of the startups I work with as to how it’s working and how it’s not. In my startups, 6 out of the 8 companies have resources external to their main location, mostly engineers who are working in remote locations. I have not seen any dramatic slowdowns with their teams.
5. People are generally just cranking. They see something needs to get done and then they just do it. There is less the asking for permission. Everybody needs to get on the same page and just keep moving forward in a very independent way. Early on at Yahoo!, many of our engineers would just do stuff and we would rarely ask them to do some particular thing. The product would constantly evolve while we worried about other stuff. Although when we asked them to actually do something and if they did not agree, it never got done which was frustrating from another viewpoint. So it worked until they got to a point when their initial sensibilities finally turned out to be wrong. Sometimes they could be convinced that they were wrong, but sometimes not…
While speed may be intuitive to some, I think it’s harder to achieve than you think, unless you have the right people with the right sensibilities and right alignment in thinking.
One of the hardest things I’ve seen is when a non-engineer comes up with an idea and tries to get it done. Because they can’t write code themselves, they need to find someone who can. But more often than not, they find only someone who can code but not become resonant with the idea to just work on it and take vague direction and execute on it.
It’s the magic bullet that everyone searches for:
“Dang it, I just want to describe my idea to someone and that someone just deals with the details and makes it happen!”
Unfortunately, it’s the details that often count…you want something done right, you better sweat the details!

Avoiding Blur

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I was just talking to a startup about their website and we were strategizing what it could become. We noodled, talked, brainstormed, argued, and finally agreed for over 5 hours and developed a sense for what we want the future site would be like.
At the end of the session, I was still feeling uneasy about what we came up with. The main reason was that it was merely a combination of what other sites were doing in part. One site would have this feature, but not the main direction for the site. Another site had people doing the activity, but in a different way. Some of the bigger sites out there also had the ability to do what we were doing, but of course their missions were much more broader and not focused like ours. Could we do better by simply having a niche, focused mission but having many of the same tools as other sites, and also competing against the fact that users were already using our competitors for that same mission we wanted them to focus on with our site?
This was the source of my unease. If there are competitors or near competitors, or even non-competitors, who allow users to accomplish the same thing on their sites, whether it is their main mission or not, AND these competitors exist already, this is a danger point. I call it “blur”.
The blur occurs in users minds when they hear about what you want them to do, but can’t figure out where to do it. They may already be doing it on some other site, by either using some existing functionality, or jacking some other functionality to get the job done.
Blur is heavily related to product differentiation. You want something to cut through the blur. When they think of something they want or need to do, you want them to think of you. Whatever functions you have must be cool, creative, and original enough to attract them to you despite being in a similar place with other existing sites.
Here is an example. Suppose you want to build a site to allow users to connect with friends. Let’s say your main interface is email, as a possible differentiator. However, as a user who hears about your offering, “connect with friends via this new way, but with email”, they’ll think all sorts of things like:
Hmm I’m already on Facebook and that works for me.
I have my address book on Outlook and email people just fine.
All my friends are on MySpace. Why switch?
I don’t have time to try something new, let alone learning it and THEN getting all my friends on it.
The problem here is that when you express your mission to users, they get caught in the blur of other competitors being able to do pretty much the same thing and you don’t have something to justify the switching cost of going to your service to do something they can do already somewhere else.
You need to find that one (or more) things that people can do on your site that no one else offers, AND is cool enough to get them to come over and learn something new.
It’s always a danger point for me when I hear of entrepreneurs who design something supposedly really cool but then I point out that people are already doing these things on other sites. I ALWAYS get pushback because they think their creation is the best out there, and nobody has mashed up the functions in such a focused manner.
It might actually be great. I’m just talking about risk here and the realities of getting users attention in a crowded space. You might actually have something that is a ton better at doing something, than for them to do it on some existing site.
I’m into risk reduction. Why try to fight with through user blur with something that isn’t shouting “Come here and try me because I’m different” loud enough? You could run out of resources and funding trying to bulldoze your way into users’ attentions. If you had several million dollars in the bank, yeah potentially you could market your way to success in a certain category.
Or you could spend a little more creative time and figure out something to build that is actually cooler and hasn’t done before, and that users will want to spend time with. Enough to get past the switching cost and try your service.
WIth that previous startup I mentioned, after 5 hours of discussion, we spent another 20 minutes talking about something that wasn’t mentioned and was something very unique in their offering. I think that 20 minutes is going to turn out to be most valuable part of that day. Because I think we added back something that would cut through the blur and thus reduce our potential risk in attracting users to our site, to do something that they could do somewhere else in general, but being able to do that one thing that they CAN’T anywhere else.
We could have gone home after 5 hours. But spending that little bit of extra time and effort to find something to avoid the blur was worthwhile and I believe, critical for the success of the company.

Social Networking is the Web 2.0 “In” Thing to Do

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Yesterday I went through an exercise with one of my companies on the social networking feature set. We went through the basic list first:
1. Add, edit, manage, invite friends.
2. Sending and receiving messages privately.
3. Announcing to friends when some activity is accomplished on the site, with announcements going out via email. Management of such communication to your friends list (instead of knowing and typing in tons of email addresses).
4. Commenting on your friends. Approval of comments to appear.
Then we added some more on top of the basic list:
1. Tracking activity of your friends via RSS feeds or announcements.
2. Affecting your public and private activity setting, by being able to expose your activity only to your friends instead of totally public and totally private.
3. Rating your friends. Enabling reputation building through rating.
4. Enabling reputation building through activity on the site.
5. SPAM management.
After that we talked about something I wrote about a while back, which is about Fame and Competition on the Net. I think fame refers to:
1. Fame amongst your circle of friends so that you feel important and have notoriety and show expertise.
2. The creation of your personal fame, which is a great way to encourage activity on the site. Create a system by which people build up their rating and reputation to create fame.
3. Application of that fame in opening up new functionality to those with higher reputation, versus those with little or no, or negative reputation/fame.
4. The ability to see their fame expressed, in leaderboards, star ratings, in comments on users, in lists sorted by fame.
Competition refers to:
1. With respect to fame, competition encourages activity by making people compete to be more famous than other people.
2. When you make things visible like reputation and ratings to the world, you foster competition when users want to have higher reputation and ratings over their friends. Leaderboards, graphical elements like rating stars, reputation building comments like those found on Yelp, are all great ways to show how great you are, which in turn encourages more activity on the site to make you chase greatness over and above your friends.
3. Getting to the top of certain lists, or placement on a certain page like a home page fosters competition. For example, if there is a module on the home page which shows recent activity, a user might increase activity just to be able to say that he got his activity shown on the home page.
4. Competition amongst people you know is great as well as to the rest of the world. A user will want more notoriety within their circle of friends as well as to the world at large.
5. If orchestrated right, competition can bring an element of gaming into the equation which can make the activity fun and engaging. That’s not to say that gaming needs to be in the arcade sense of the word; it just means that a sense of play, of being able to strive and to win are elements that need to be present.
Social networking for meeting and activity management are the basic functions. But I would argue that they are not enough. There are enough social networks out there where you can perform these functions. A site who wants to employ social networking needs to rise above common functions, such as with elements which generate fame and competition. You want to make your site more than just a place for meeting and hooking up. Design activities which foster meeting AND fame and competition AND encourage activity on your site and you’ll win across multiple goals.

The Chaos of Orgs and How it Hurts Employees: Management by Influence Hurts When Clarity is Absent

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Two weeks ago I met with someone who just left Yahoo!. We commiserated about our experiences at Yahoo! and I asked about this person’s experiences and why they left the company.
It was a familiar tale from many of those recently leaving Yahoo!, and also one that was just beginning to manifest itself when I left in 2004.
As Yahoo! attempts to reinvent itself, a lot of chaos and reorganization is happening under the hood. This person related to me how they had, over a period of only a year, several managers and being passed around to many groups. As this person attempted to do their job, direction was confused in the parties this person supported. As these parties’s ALSO underwent many reorgs and change in management, it caused confusion and a lack of ability to approve anything or willing to make a decision, or even figure out who it was who could really authorize a decision.
That doesn’t mean nothing gets done at Yahoo!. In fact there is (was?) a huge cadre of people who, having grown up with the organization, knew exactly how to get something done. This was accomplished through personal relationships, keeping up with who really supported what technology, and what levers to push in the organization. I call this “management by influence”. The problem is that a huge percentage of the old timers at Yahoo! have or are leaving the company. This leaves a huge void in the company.
So as the people who can really get things done leave, people find it harder to get things done outside their own sphere of knowledge and influence. Add that to a org who may give firm responsibility to people AND announce that publicly and thoroughly enough so that everyone knows who to go to for what they have to get done, and confusion and chaos grow. The funny thing about this is, if you ask any upper level manager if there is clarity in the org, I bet they will say there is total clarity. The problem is that they announce something, but the message nevers get into the lower orgs, or is detailed enough to be clear as to exactly who they should go to for what. Now let’s add communication problems issues to an org too busy to formalize communication. More chaos ensues.
The scorecard now is:
+ Reorganization causes chaos. Too many managers has a negative impact on the employees.
+ Management by influence works for the old timers but they’re all leaving. New timers used to go to the old timers/management by influence experts but now they’re all gone.
+ Communication problems exacerbate the problem.
Employees need stability to perform the best job. They need clarity in their jobs and know that they have a stable manager who cares about them and can direct them effectively. Part of this is because of the dependence on what I call management by influence versus clarity which I argue has obscured the lack of clarity of the organization. By clarity, I mean there is a person you go to for this and everyone knows this. This division does this and does not do that. And on and on.
In small orgs, this is easily achievable. You know someone does something and it easily fits into your mental map of how things work in that company. In large orgs, you have to institutionalize communication and clearly delineate lines of responsibility to the entire company. If you’ve ever worked at IBM, there are huge documents, memos, and directories which document these lines of responsibility. Is it heavy and unwieldy? Yes, probably. But it is definitely clear and removes the need for management by influence alone. People can remove themselves from the org but the position is always there, even if the person is not.
The other part of creating a stable environment for employees is to stop shuffling them around like chess pieces. They are not pawns; they are humans. They need to stop dealing with the chaos and turn that energy on what they got hired for. Those of us in upper management would do well to create these stable environments where employees can flourish, feel needed and valued, and are clear on who to go to to get something done. If you don’t, you’ll get the exodus which ultimately drove this person, and tons of others, to leave.

Hotlists from HotorNot.com

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Interesting new widget from my buddy James at hotornot.com.

I can put the persons, places, and things that resonate with me in this widget which denote what’s cool, influential, and important in my life from brands to people and anything. Pretty nifty. I think a way to express this is actually kind of interesting. No other way exists that I know of to do this.
We always express ourselves by the things we wear, or who we talk about or idolize. But we have primitive tools to make this known. We cut out pictures and paste them to our wall. We buy clothes and wear them. At least with this widget, we have an easy way to pick out those things that influence our lives and let others see them.
Something interesting to watch….

Corporate DoubleSpeak is Alive and Well

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Thanks to IBM, corporate doublespeak is alive and well. In fact, they are so good at all those corporate buzzword techniques that they put it all in an ad at JFK Airport:

I suppose if you want to help at getting better at whatever these buzzwords actually mean, you should hire IBM and they’ll “chain optimize” the hell out of those buzzwords into your psyche so that you’ll “process transform” your business for the better.
I once tried to learn corporate doublespeak. At one point, I thought it would make me more successful. But then I read Dilbert. And it was all over.
Corporate buzzword books plague the bookshelves and make you want to buy that book out of sheer curiosity of wanting to find out what the hell that term means. Thankfully, I’ve “re-engineered” my tendency to buy these types of books and now avoid them by at least “six sigma” distance.

Voxpop Moves to Pier 9

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Voxpop just moved from their high rise offices in the financial district to a space much more cooler and startup-chic:

Pier 9 is owned by the city. The rent and view are AMAZING. Looking forward to beer parties on the pier overlooking the Bay Bridge this summer!

Are You Startup Material?

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It all started with my recruiting woes. I dutifully plowed through my contacts every time one of my startups was looking for new hires. I talked to many of them but almost all of them refused to leave where they were to go take the leap to a startup. After many conversations, I figured out that startups aren’t for everyone. It was a frustrating but interesting learning experience into the changing lives and minds of our workforce, and what was appropriate for one person would be inappropriate for another, and that which could change over time.
Are YOU startup material? Looking now at who you are, what motivates you, and where your life is – would you want to make the leap to join a startup? Some questions to ask yourself (and some discussion on each):
How young/old are you?
Startup people are typically young. At least from a physiological standpoint.
Young people have lots of energy and stamina to stay up late for nights on end. They still have the ability built up from pulling constant all-nighters from college so they still retain this ability even after they graduate. Their youthful bodies still have strong hearts bolstered by endless, sleepless nights partying on beer and chicken wings. Their brains are quick and agile and not dulled by age. The older you get, the more your body has reduced stamina to stay up all night and hack. Old brains just don’t work so fast without proper sleep.
And it really sucks that as you grow older, your chances of entering a startup diminish greatly. This is a shame because the most experienced people you want tend to be older.
Can you go for a long time with a reduced salary? With no salary?
Once you enter a startup, you’re entering a place where reward is typically bound to options and stock, not weekly salary. This reward can be long in coming, ranging from months to years. How long can you survive with reduced salary, given your dependents and lifestyle? Are you willing to risk that? Do you have enough saved up to last for a long amount of time, say months or even years?
Startups can’t pay market salaries. If you need immediate cash, startups aren’t for you. Go find a job at a stable, growing company.
After a startup raises money, they can pay you more, but it can still be reduced from market levels. After all, the money is a great motivator for you to work long hours for the big win; if you get it all upfront, then where’s the motivation? You’re not hungry.
How many attachments do you have? Are you married and have family or dependents? Do you have a lifestyle that requires attention and/or capital?
As for age, young people have little or no attachments like spouses or children or possessions, which is another reason why you find young people in startups. Starting from almost nothing, they have nothing to worry about except themselves. It is very easy to throw your life into a startup when your life is not occupied already.
But perhaps you have other interests which take time. You may like to volunteer at a non-profit and gain lots of satisfaction from that, or train for Ironman. You like these so much that you are unwilling to give them up for something else which will undoubtedly be all-consuming.
Owning expensive things like houses and boats take up resources. You need immediate cash to pay for mortgages and bills. Do you race cars for a hobby?
Are you married? A spouse and family will put demands on your energy and time. Are they willing to give up their time so that you can pursue your interests in a startup? Are they truly OK with not seeing you at home for dinner many nights? Be warned: those that have not experienced the startup world may think they know what it’s like time-wise, but I will guarantee you that they may have zero concept of what it’s REALLY like. Make sure you sit down with them and talk it through in excruciating detail and get their support and buy-in. More than one family has been wrecked because of too much time spent at a startup. Make sure YOU know you’re joining the startup for the right reasons and with the right familial support.
Are you comfortable where you are in life, job, family, etc. or are you hungry?
If you’re comfortable, you may not be willing to give up your current job with nice high salary and which supports your current lifestyle. You may not want to stay up all night working for little pay and for a risky return some unknown time in the future.
If you’re hungry, then perhaps you could be right for a startup. You may want more out of life, more money, more fame. Whatever it is, it’s more than now and you want it fast and not wait decades. The only way you can get this faster is if you take more risk at a startup which could vault you to whatever it is you’re lacking.
Which leads to the next point….
Are you conservative or a risk taker?
If you are a conservative person, STAY AWAY FROM STARTUPS. If you cannot risk your entire career, fortune, whatever, at all, you shouldn’t consider a startup. You’ll drive yourself nuts and everyone else around you.
Can you deal with ambiguity, adapt well to change, be ok with constant chaos?
A startup is not known for stability. Things don’t work as smoothly as you want and you have to be OK when things aren’t perfect, or forgotten, or done in haphazard ways. If you require order in the way you do things and need that around you, a startup is probably not for you.
Do you like to learn and do everything? Do you not mind taking up tasks outside your areas of expertise?
Startups are typically short staffed. Everyone typically pitches in and does a little of everything. Marketing people code HTML pages, Business Development folks take out the trash, Engineers open up photoshop and crank out graphics for the site. If you like to learn and either want to become or are a jack of all trades, startups are the perfect environment to grow your ADD.
If you just like to do your thing and pass the buck on everything else, I am certain you will be shunned by everyone on the team.
Lastly, are you passionate about the startup you may join?
Passion drives humans to do amazing things. If the startup you’re joining seems cool but your heart really isn’t in it, I would highly recommend not joining it. Wait until you find something that you can really get behind. Passion will give you strength and stamina to work long hours, to really resonate with what you’re working on, and give you extra motivation to keep working even when you’ve been not sleeping for days.
Startups can give you the experience of a lifetime. I would not have given up my experience at Yahoo! for anything and it taught me a lot about passion, the thrill of working together with a whole bunch of smart, motivated folks, and a lot about myself and what I am made of. But like it or not, we’re not all startup material. It’s something we need to be realistic about, and also, for us on the other side trying to recruit for startups, it’s frustrating but we understand.