June 2008 Archives

We finally have our very own office, now in the Meat Packing District just next to Pastis. Yesterday I saw for the first time hanging carcasses of meat outside - and I thought the Meat Packing District was just all hipster bars now!

We're in the old warehouse/building of Collier Encyclopedia, whose globe still adorns the main entrance.

Love the high ceilings and loft style openness! Thank god for IKEA whose inexpensive furnishings adorn our new home. We're also right down the street from great restaurants, bars, the swank new Apple Store, and Google is 2 blocks away.

Fun with Wordle


I just got sent a link to Wordle, a fun tool that takes a block of text and creates a word cloud of the text. Check out my bio washed through Wordle below. Interesting to see one particular graphical representation of the information therein:

I am often asked about how many investments I've made and I surprise them by the number I have made in such short a time. I too think I went out too fast as a budding angel investor but, looking back, I think ultimately this had many advantages, some of which were not obvious to me until I did it.

The obvious disadvantages are that I had allocated a portion of my personal savings to do this, and I ended up deploying almost all of it in 2 years! This unfortunately meant that I had to slow down dramatically the number of investments I do from now on, and potentially ratchet down the size of investment into new companies.

The obvious advantages of going wide are that you spread out your risk, just like diversifying your investments in your personal investment portfolio of stocks, bonds, etc.. Putting your eggs in one basket, or a few baskets, increases your risk of losing it all no matter what you put your money in.

The non-obvious advantage of going broad was the knowledge I gained from exposure to different companies and their personnel (and their personalities!), their products, their struggles and solutions.

I always knew I had ADD, and that I enjoyed working on multiple products. In my old position as head of user experience at Yahoo!, I could satisfy my ADD tendencies towards getting my fingers dirty in a variety of projects, and learning about many others. After I left Yahoo!, I wondered about how I would provide an outlet for my ADD-ness and orchestrated a solution through angel investing. By investing in many companies and becoming advisor to them, I was able to continue to satisfy my Internet ADD.

However, being exposed to so many products and projects also allowed me to see across many different products and be able to connect them in ways I would never have been able, had I not had access to the depth of information in each product. I was able to see synergies and feed my creativity, which allowed me to come up with ideas that would not have come to light without the broadness of depth of information (if that made sense). I had always been a big believer that creativity can be enhanced with more information (but also knowing that creativity can often be reduced because you get bogged down by knowing too much) and this was further proof of my belief. Working on one or two projects would never had given me the insight that I can see now. Also, if I was not advising and/or investing in these companies, I would not have gotten the depth I needed to be truly successful.

It was an non-obvious result of the diversity of my investments that I would be a more effective advisor to internet startups. My broadness of vision across many different products and projects means I can bring creative proposals to time starved entrepreneurs whose myopic but necessary focus on their own projects sometimes prevent them from seeing the wide view and potentially better alternative paths and solutions.

Should I Go Back and Help Yahoo?


Earlier this week, a few emails went around the Yahoo Alumni Yahoo Group talking about the recent news about Jerry Yang and how Yahoo was totally floundering and going down the drain. Some of them talked about even going back and helping somehow, although they were quickly retracted in a tone of "that was a really stupid thought."

In fact, after reading some of the news earlier this week, I too had a moment of "Maybe I should go back and help Yahoo." It came and went quickly amidst similar feelings surrounding not wanting to jump back into the frying pan to not knowing what I would do once I got there.

However, instead of mocking such a thought, I'd like to put another spin on it. And that's the fact that we would even have thoughts at all like that.

What was it about Yahoo that would make a whole bunch of us feel like we could go back and actually make a difference? Why would we want to save the company? What could have possibly shaped our feelings and attachments to a place that was our home for many, many years? Why is it so hard to let go?

Yahoo was a unique place. It was like family. It was like a revolution. You bought into it, got emotionally bound to it, and worked your butt off to make it happen. People would applaud the fact that we worked at Yahoo, and we were seen as celebrities of the internet back in the day. We all hung out, we partied, we succeeded and failed and brought it all back from the brink of internet bust.

That's what makes it hard to let go.

It makes me wonder what we could learn from that experience. After all, wouldn't any CEO want to create a workforce which, even after they left (or were fired, or laid off), that would want to come back and work there again despite whatever obstacles and turmoil there could be? What could inspire loyalty in a corporation like that, in a day and age where loyalty to a company is disappearing...?

How Does One Advise So Many Companies at One Time?


Often I get asked by entrepreneurs to become advisor to their company and they take a look at my companies page and they wonder how I can handle so many companies at one time. Where does Dave find the time? Do the companies actually get enough support from me given that I am advising so many?

It's actually not so hard. Here's how:

1. I've found that advisor time commitment varies greatly from company to company. Some entrepreneurs use me as traditional advisors are used, which is to meet up once every month or quarter and give me an update and go through their plans and get my feedback. If all my companies were like this, I could definitely advise a ton more.

Others call or email me whenever they need something. I have many hours in the day and definitely can field calls or answer emails. Sometimes they ask for a site review or recommendations. This takes longer, but blocking out a few hours to do that isn't a problem.

Some have wanted meetings weekly for a while. The weekly meetings never last though; entrepreneurs are pretty busy and they get going on something and they don't have time to meet up any more. Or they learn enough or have firmed up plans enough to keep them going for a while and then they don't need my constant interaction.

2. Perhaps the greatest time commitment is just thinking about each company daily. I often have at least one (or more) of my companies swirling in my brain and I try to record any ideas down asap. If I am in front of my Mac, I'll open an email and just record the ideas in that; also, I have a small moleskin notebook that I carry around with me constantly to jot down ideas. Once I get all my ideas down, I check it over, do some rewrites, insert additional ideas that come to me on the fly, and then send it to the entrepreneur.

I like to get into the mode of a single company and its product and try to immerse myself in the product as a user, and the experience of needing/wanting that product. That enables me to really get into what I would want, and also what others could want in that product and where improvements can be made.

I multitask on this throughout each day, but sometimes I take some focused time and do this too.

Still, once a company receives these ideas and acts on them, they usually don't need further time from me for a while.

3. Another task I do for my startups is connecting them with potential partners and sources of capital (although definitely I do not bill myself as a fund raiser). This requires me to network a lot with both old and newly met folks. Thus hour long coffees and lunches are the norm and these take time out of my week.

Also, I write a lot of emails introducing my companies to these partners as well. Thinking about which partner to send the company to and also sending the email does take up time, but not all that much.

4. My favorite thing to say about advisor time commitment is that almost all companies need the most time at the beginning of our advisor relationship. There is a big spike in time and thinking from my side and also in interactions and then somewhere between 2 and 6 months later, that time drops to near zero, with little peaks of time to do emails and check-ins.

The rationale behind this is that the company is supposed to learn everything I tell them. They finalize their plans with my input and feedback. They take this knowledge and are off and running building their product. They don't need my interaction so much after this time because they have what they need from me.

This is one of my main goals: To transfer knowledge from my brain to theirs so that they don't need me any more. If I do this successfully, they should be able to function for a long period of time without my input. Over time, my goal over the term of my advisorship is to help them find resources that would manage what I help them with day to day. This is finding and hiring a great full time design resource and great product management resource. It can also mean finding/hiring a great sales program person as well, to help them monetize their advertising programs.

I've been advising for about 2 years now, so many of the companies on my companies page are off and running without further need of my help.

4a. One thing that I have consistently observed is that if my time requirements spikes again after the initial peak, the company is in trouble...so I keep watch for this and hopefully help prevent this from happening.

5. OK OK I admit it. Even working like the above, I still can get pretty busy in the short term. In fact there was a time when I thought I was overextending myself due to the pace of advisorship signups. So now I am very aware of the pace of companies I advise and have slowed down dramatically based on my current support load.

6. Next, I tell people I shouldn't be put on critical path for anything. It's not what advisors do anyways.

A lot of people ask me to be advisor, but really want me to do the design of their site for them. If they want this, they should either outsource their design or find a designer to hire full time, and not try to turn an advisor into a fake full time person. I think this is especially true in product design; in order to do a great job, you have to be immersed 24/7 with the product and team. It's hard to jump in and out or do it on the side.

If I'm not on critical path, that reduces time commitments from 24/7 to something much, much less and less frequent.

As advisor, I always tell people that I shouldn't be expected to be put on critical path for anything because we're both going to end up being disappointed and frustrated. Very bad!

7. Last, I love being involved in many things. It helps keep my interest level up and allows me to see the entire world of internet startups across the board, which is an advantage. I purposely try to get involved across a myriad of projects, across a range of areas.

It takes me out of being myopic into one thing, and allows me to help my startups by being broad in my thinking and not get too trapped into the details of one project. While this is important from an execution point of view, it doesn't help when you're helping to plan the strategies of these startups by not looking outward and seeing where the trends of the industry are going. Often I bring the broader view to my startups because they don't have time to look at it themselves. They're often too busy to do that. On the other hand, I want them to spend all their time executing and not get distracted.

I've really come to love advising startups. The connection with smart, energetic people working on cool new things is really great, and I enjoy helping broaden their vision and give them the help and knowledge they need to be successful.

Stealth Startup in SF 6-13-08


Yet another (stealth) startup in their second location, and up to 6 people.

This building is one of those housing a few other notable startups. Many such buildings exist in SF, and the startups all seem to pile together in these old buildings whose remodeled interiors make conditions much more bearable inside.



In Macworld magazine, I read about a great software program for writers called Scrivener. My writer and I have been using Google Docs and MS Word to write and we were reaching a point where this book was getting harder to manage as one long stream of text. We were using Kinko's online service to print the whole thing out, but working this way, which is a more traditional way, would be time and money consuming. It was also difficult as we didn't have outlining capabilities in MS Word, or at least hadn't been able to figure out whatever was available in MS Word.

Enter Scrivener. Wow. What a difference. The software allows writers to separate the work into sections and gives you many different views on the work, whether in corkboard mode or in outline mode. You can then work on the doc section by section which is much more faster for me, and also take a look at the whole doc with the sections assembled to see if it all appears together correctly. The transitions then can be worked on separately, which is fine because my biggest barrier is to just focus on a particular section first and get the text out of my brain.

Then, you can always export the doc into one long Word or text file. The sections get all assembled and you can print it out or send it to a publisher.

The one thing that would have been nice would be to have some collaborative method of working together that doesn't mean coordinating file versions and passing them back and forth. Perhaps some merge method? Online site support where the files are synced? For now, we'll email the file back and forth when changes happen.

If you're writing an article, book, or whatever, I would highly recommend Scrivener!

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This page is an archive of entries from June 2008 listed from newest to oldest.

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