Sometimes I hate meeting somebody I have never met or haven’t seen in a while. It’s bad enough trying to remember someone by picturing them in your mind, let alone trying to figure out who someone is without even meeting them in person before.
But make that worse by asking for those people by name and then being shown to their table and then you realize that the person sitting there is not the right person…AND…they have the same name!
The first time this happened with someone named Lynn whom I had not seen in a long time. I go to Pershing Square and ask for reservations in Lynn’s name, and they say she has already arrived and is waiting for you. I say, great, and follow the server to the table. I see someone sitting there with blond hair, so I approach from her back and then say hi to her face and realize it doesn’t look like the Lynn I knew. I say excuse me, and ask her for her full name, and it’s not my Lynn! She laughs and was also wondering who the hell I was, since she was expecting two other people. She jokes about joining her but I needed to meet the real Lynn so I move off and my Lynn shows up a few minutes later.
The second time was just this last week when I asked for someone named Adam at Olives in the W Hotel at Union Square, whom I had never seen before. I was shown to a table where there was a guy sitting there named Adam, and he and I greet and I get a call from another person meeting us for breakfast but is now telling me he can’t make it. I sit down and then start talking about my flight out and a few other things, and then we realize that I’m not the person he is supposed to meet, and he is not the Adam I am supposed to meet! How funny! I grab my stuff and go back to the front desk and there is the real Adam there waiting for me.
Usually I don’t have a problem finding and meeting someone I have never met or someone I have not seen in a long time. But it’s doubly weird when there are others with exactly the same name having reservations on the exact same day, time, and place to trip me up!

Just recently, I saw two startups go into “overdrive” mode. By overdrive, I mean the days of working 24/7 come into being, and you can see the bleary eyed entrepreneurs staying up late for nights on end, working to get their products up or maintaining them, doing it knowing that resources are tight and that there is no one else to turn to but themselves and that there is no where for slackers to hide.
Startups are inevitably short staffed. There isn’t enough cash in the early stage to hire enough people to do everything they want to do. I often warn them about the work that is required and hope that they have some forewarning. But I balance that with not scaring them so much from backing off on what they need to do and motivating them to stay up 24/7 and do what it takes, no matter what.
It’s easy to just give up. Go home and go to sleep. The leader needs to whip them into working every day and not going home until it’s done. The leader constantly needs to remind them that the survival and livelihood of the startup is at stake and that the future rewards are what everyone is working towards, and yeah it sucks in the present because you’re working 24/7 and getting butt tired.
To me, motivating them is easy. I tell them about my experiences in the early days of Yahoo. Surely they sucked from the standpoint of us getting no sleep, being perpetually tired, and knowing that your social life is gone. But I will definitely say the bonding experience of working in a small team and doing what it takes to get the product out the door is one not to be missed. Staying up late knowing that you’re not alone, and that there are others depending on you, and that you all are there working your butt off means you build trust with your teammates. You really find out what you and your cohorts are capable of, and who is going to give up or not.
It is like when you build a squad in the Army and you go out on patrol in hostile territory. You have no choice but to watch each others’ backs. Once you go out on patrol a few times and the enemy pops up and tries to shoot and kill everyone in the squad, but it doesn’t happen because your squadmates have saved you and you have saved their asses more times than you can count – there is no substitute for the bond that forms knowing you’ve all been through the trial by fire and come out knowing that you can depend on others to watch out for you.
You never know how someone will react until they are put under stressful situations, and in depleted situations where your personal resources are stretched to the limit. A lot of people can’t take it. They collapse, give up, run away. The Army or early stage startups is not where they should be.
But those who survive the test, and you, knowing who does and who does not, will know who you can trust at the eleventh hour and who you cannot.
It is a badge of honor amazingly enough. I used to tell stories of the old days at Yahoo and the new hires would be so impressed about the endless weeks of staying up all night getting stuff done. They seemed to idolize that. I shrugged it off mostly and just chalked up to storytelling about the old days, but I think deep down inside they wish they could have been part of that energy to do what it takes and don’t stop until it’s done.
The team unity of creating something and getting to the end is a huge factor. The satisfaction you get from watching something launch, after weeks upon weeks of working on it 24/7 is a feeling of accomplishment that transcends. You know you’ve accomplished something super difficult and watched it birth out to the world. On the Internet, the unfortunate thing is that you can’t fire and forget products; you need to worry about after they launch as users come onto the system and you then worry about post-launch things like the servers going down under unexpected load or maintaining editorial content on the pages, etc. The funny thing about Web products is that really there is no end. I’ve often stayed up late with teammates watching products go up, and then I go home to get a few hours of sleep, and get into the office before everyone else just to check on what we launched the night before. Most of the time you hit the site with your browser and everything still looks good; however, there are times when you login at 7am (after going to sleep at 3am) and….nothing pulls up…! You pick up the phone immediately and wake everyone up to figure out what’s wrong with the servers and the game goes on…
By the way, if you’re the leader of a team, I would strongly suggest you stay up with the team. Nothing is more demotivating than the leader who tells you to work all night, and then goes home at 5pm leaving the team to continue working. If you want respect from the team, there is nothing like telling them to work all night, and then staying up with them. This is even if you have nothing to do. I’ve just sat in my office at times, reading a book or sometimes even taking a nap while my team works around me.
So today I am out of that environment mostly, but I still retain the ability to operate on virtually no sleep. I thought about this a lot and offer some tips on increasing your ability to work endlessly on no sleep:
1. Vitamin C. I drink a packet, sometimes two of Emergen-C which is 1000mg of Vitamin C. Back in the old days, we’d have bottles of chewable Vitamin C and pop them like candy. There is conflicting research into whether Vitamin C really keeps you healthy or not, but I for one am a huge believer that pumping your body with Vitamin C prevents a lot of diseases that you can catch due to lowered resistance from lack of sleep.
2. Tums. Sometimes stress and no sleep can cause your stomach to do weird things. I used to take Tums to calm my stomach from excess acid and gas. It helps a lot.
3. Working out seems to increase your tolerance to operating without sleep. Dean Karnazes is noted for his ability to operate on four hours of sleep a night, getting up at 3am to run his daily 4 hours for ultramarathon training. My belief is that exercise is key to training your body to be able to function with less sleep. You keep healthy, you achieve deeper sleep during your lesser sleeping hours from being tired from exercising and it removes your stress. It clears the mind and helps you think clearer as well.
4. Along with exercise, you just adapt physically to operating on less sleep. Remember in college when we used to study all night? We seemed to be fine doing that for months on end. I think humans can build the ability to operate on less than 5 hours of sleep a night. Hunker down mentally and just get up even though your body and brain doesn’t want to. Keep moving all day and don’t stop moving. Coffee helps, but try to do it through mental fortitude and not drugs.
5. Having a sleep recovery day is beneficial. I try to do this on a weekend night where during the week, I may be getting 4-5 hours a sleep a night but then on Friday I don’t go out, crawl into bed at 9am and wake up whenever I feel like it. Recharging one night a week really helps.
6. The last and most important: POSITIVE ATTITUDE. Here is where I think the mind-body connection really comes into play. If you feel like whatever you do is dragging you down, you WILL GO DOWN. On the other hand, if you are energized with what you’re doing, you enjoy it, you are driven by it or any one or more of many other reasons, you’ll be able to do it and more. Try to find something that really interests you, that you can sink your teeth into and enjoy, something that TURNS YOU ON. Believe me, you’ll be able to work 24/7 for months on end and not look like the cat dragged you through the mud.
The days of working all day and all night are not to be missed. Everyone should experience it. It’ll take you to heights of creativity, turn you inside and out, bond you to a group of people with common purpose and you’ll party like it’s…well, not 1999 but maybe 2999 when you launch. I highly recommend it. You’ll thank me.

I really love this office space operation in Manhattan, Sunshine Suites, this one at 419 Lafayette near Astor Place:



The tree branches around the conference rooms is a bit freaky. Makes you feel like they are going to reach out and grab you. Don’t have a meeting here while on drugs!
It’s only about $400-$500/month for a desk. You get a phone, internet connection, unlimited usage of xerox and fax. And it’s decorated in New York chic. The entrance to the floor looks like the W Hotel. There is even sexy house chill music playing in the bathrooms to relax you when you…well…you know…

I just bumped into these guys in Manhattan: EastMedia:

Really cool bunch of guys and really good at Ruby on Rails. If you’re looking for a small development shop in NYC, you should definitely check these guys out.

This week and the coming week I am bringing some entrepreneurs to meet with some people in my network. And the results of this week’s meetings reinforced to me the importance of connections in my line of work.
I had originally placed more emphasis on my personal skills, ie. product strategy, user experience, etc., in helping early stage internet companies. I had not thought my rolodex was strong enough to contribute in that capacity yet. But I knew as time went on, old colleagues of mine would leave Yahoo! and have ended up in some companies which I knew would prove useful to my companies. This would be a valuable asset to my business and, thus, I began a side project of networking more and getting out there as much as possible.
I also resolved to approach this networking from a slightly different perspective. There are what I would call professional networkers out there. I have found these people only network purely for business reasons. They get out there and have conversations about how they can work together and it rarely goes beyond business type conversations. I thought I would attempt my networking to have a slightly more interpersonal aspect with it. Yes, we would potentially begin with business focused discussions, but I would always leave the door open for making it not-always-business related. Who wants to keep talking about the industry anyways? Combining this with my belief that working together can be enhanced when you geniunely like hanging out with each other makes things a whole lot smoother and easier.
I am finding that as I do things for other people, that I also get some of that in return. For that, I am eternally grateful. Everybody is busy, but as I make time for others, they make time for me and my projects, like when I ask them to help me review their funding presentation.
We did just that late Friday afternoon and it was extremely fruitful. I brought one of my companies into a meeting with two guys who I thought had just amazing sense for putting creative deals together. When we left the meeting, I thought that it generated some real new possibilities that we hadn’t thought of, and now we’re going to talk about how that affects our final rev of the funding deck. If we can get some of these ideas in motion, it would certainly make our funding deck that much more attractive.
Another meeting I had was with a prominent media company exec I knew. First, I think my chances of gaining a meeting through cold calling was pretty slim. In this case, I had some history with this person and he was willing to take the meeting. It also turned out to be very good. While the person didn’t have anything specific for us, he was willing to introduce us to a person in another division who might be interested in our technology and product.
My strategy with these connections is thus:
1. I know the importance of the interpersonal aspect and thus am willing to try build relationships beyond just business.
2. I am willing to help them as much as they help me. And I won’t charge them for doing some presentations or just a meeting or coffee or two with someone they want to meet me and learn about what I do. I have always been willing to make time for any of my connections.
3. I continue to build trust with my connections.
The first area is with not bringing frivolous time-wasting proposals and startups to meet with them. I won’t do it. Everybody is so busy and time is valuable. I don’t want to setup a meeting unless I think they can really benefit from it. Thus, this maximizes the chance someone will take a meeting with me if they know that 99% of the time it will be something really cool and worth their time.
The second area is with investors. This is trickier. The number of people who claim to be fund raisers is staggering. But I think there is a problem with their business; almost all of the time, they are not investing into the companies they bring to investors. They get paid either on a percentage of successful fund raising or get paid hourly for their work. As an investor, you will never know if these are good deals or not; the person bringing them to you is getting paid no matter what! For me, I don’t want to work that way. I won’t open up my investor network unless I have put money into a company. It is the ultimate sign of confidence in a deal; you have put your own skin in the game.
Unfortunately, my investor network is the smallest out of all my networks. It’s definitely an area I’m working on now.
The third area is with introductions. There are some people who are willing to make introductions quickly. Almost too quickly. Perhaps that is a sign of trust for me. Perhaps not. But sometimes, I think it’s a bit too quick. I think they should think beyond the fact that it’s me and they know me. I think they should get to know why I want the intro, as well as the mind of the person they would be introducing me to, and then think hard on whether there should be an intro or not. Sometimes, there shouldn’t be. Or you might need to wait a while until conditions are better to ensure that there will be a successful response. Or maybe there should be an introduction yesterday.
This is in an effort to maximize value to both parties and minimize time wasted. It also helps the person who is the receiver of the introduction know that you, the introducer, aren’t making frivilous introductions and they just sit in an email inbox forever not read or responded to. My goal is to have 100% of introductions returned and matched up. If an introduction email is not responded to, I know I’m doing something wrong.
Build trust and keep building.
4. Lastly, I intend to be honest, clear, and straight-up about everything. If I can’t do something, I’ll say so. I won’t beat around the bush on that. I want people to know I mean what I say and where I stand no matter what.

In the past few weeks, there have been a number of highly publicized and not-so-publicized upheavals at major companies. Some of my friends work at these places and I ask them how they are doing and whether they will leave.
One pattern that is starting to emerge for me, especially amongst the “job jumping” generation I’ve grown up in, is that people are getting tired. Tired of jumping to a new job and starting over. They’ve done it so many times that it is wearing them down and they don’t want to do it anymore.
As loyalty to a corporation has waned over these last few decades – and I support the selfish behavior of the “job jumping” generation because companies have reduced or removed the reasons why people should be loyal to a company – people have been switching jobs at a huge rate. At one time, it was not looked favorably upon that a resume had a number of companies on it; now it is the norm.
As people have jumped jobs often, they are realizing that starting over in a new job and new company is not easy. The cost of integrating yourself into a new organization and culture is high. You need to rebuild your reputation. You need to rebuild your internal networks and maintain them. You need to learn new ways of doing things. You need to adjust to new styles of working. And the list goes on.
It wears you down to start over again and again. The first few times it is exciting and new; after a while, you get tired of going through the same motions to reestablish yourself in a new place.
It is wearing enough that people are willing to stay in a dysfunctional, negative, or the wrong company when they really should move on.
This bears watching as time goes on.