I am about as passionate as anyone regarding entrepreneurship. I work and play amongst circles of entrepreneurs and always offer guidance to any aspiring business-minds who are trying to hatch their killer idea. Most of the time, I am lending advice to early to mid-stage startups about strategy, product development, or finance. While my strong point is not finance, I certainly understand the process at which an entrepreneur must go through to execute on a funding strategy and ultimately, close the venture deal.

I’ve decided to take some time to write a check-list that an entrepreneur should follow in order to have the most efficient and effective funding strategy. This list is not the end all and be all of how to get venture capital dollars, but will certainly help in your approach to working with VC’s. To round this posting out, I realized that what I’ve got to say is just one side of the equation. So, I’ve asked some extremely active VC friends what they look for in a company. Raj Kappor (Mayfield Fund), Nick MacShane (Progress Partners), Brad Feld (Mobius Venture Capital), Alan Kelley (SJF Ventures), and Keith Benjamin (Levensohn Venture Partners) all have added their two cents into this article with some original answers (thank you guys very much for taking the time to do so!). Read more »

I’ve been involved in many conversations over the past few days about whether or not New York City is sustainable for digital media/technology driven startups or is the San Francisco area the only fertile ground. My stance is/has been that New York has a thriving entrepreneurial scene and certainly is more than adequate for these types of startups.

In the nextNY group which I helped get of the ground and actively participate in, we have been discussing this topic for quite some time through our Google Group and at our monthly meetings. Randal Stross, a writer for the New York Times recently wrote an article about how technology driven startups should exist on Sand Hill Road (or thereabouts) in order to succeed.

New York City is home to the media capital of the world and Madison Avenue. We seem to quickly forget that many startups in the digital media world are driven by advertising dollars. Why wouldn’t you park your startup next to where the dollars are flowing in from? I’m not saying that 100% of ad-dollars are spent in/around New York but there is certainly a heavy influence of advertising spendings from Madison Avenue. In the Valley, you’re about 3,000 miles away from Madison Avenue – away from your revenue source.

The world is becoming increasingly flat thus distance is a word of the past. Skype, AOL IM, etc have all made communication effective and efficient. By utilizing these resources, a company can operate from anywhere in the world and be in constant communication with it’s team. An organization today can be spread across many offices based on geographic regions or technical expertise but can be connected through and intranet and VOIP.

While venture capitalists typically follow entrepreneurial spirits to all ends of the globe there is no doubt that quite a few exist on Sand Hill Road. Some of the top global VC’s have offices here and do earth shattering deals that produce the next hottest startup. However, Sand Hill Road is not the only place where VC’s exist. New York is home to some extremely large and small firms a like including Union Square Ventures, Easton Capital, SJFVentures (their New York Office), and many others. These VC’s recognize that New York is certainly fertile for startups and are here to work with the entrepreneurs that have a strong business plan and management team. While Sand Hill Road has historically attracted entrepreneurs and investors, New York is certainly not to be written off. A fantastic choice for entrepreneurs in the media and advertising industries to anchor themselves, NY offers many opportunities that many places in the world cannot.

I will admit that NY may not have the same entrepreneurial atmosphere and culture that Sand Hill Road posses but each city is it’s own and we here in NY should not try and be someone else. We have a thriving “Silicon Alleyâ€? and nextNY group that is dedicated to spreading the vibe and culture and NY will certainly put itself on the map for entrepreneurship in the not too distant future.

NYC bloggers and digital media evangelists should get together and keep promoting the start-ups here. There is no reason why NY can’t be a fertile ground… after all, NYC is the “Big Appleâ€? and Apple’s grow on trees that have been planted in fertile soil.

Well, not really… however, last night we went to Radio City Music Hall to see Paul Simon perform and it was a fantastic show. To begin, I’ve not been to Radio City for quite some time so the renovations they did years ago are absolutely gorgeous. Secondly, Paul Simon came out on fire and played a fantastic show including multiple encores.

I’ve been listening to Paul Simon since I was a child. My father is from South Africa and has been a fan of him for quite some time and always played his music when we were in the car. Growing up, listening to Rhythm of the Saints and Graceland albums were a common occurrence. Attending the concert with my folks was special because this music is something we always shared together, and finally being able to see him live was extremely moving.

The set consisted of what you’d expect from him. Highlights of the show were Graceland, Mrs. Robinson, Boy in the Bubble, and Cecilia. Paul may be getting old - but is quite a performer. I would love to see him take the stage with Dave Matthews and perform Boy in the Bubble or Mrs. Robinson.

His new album, Suprise is certainly one to pick up. I highly recommend downloading it via iTunes or purchasing it in the stores as it’s stylistically very different. Let me know your thoughts about the album!

It was fantastic meeting everyone today at the Soy Luck Club.  We ended up talking about a range of different topics including VOIP, funding, online media exchanges, in-game advertising, next generation consoles, outsourcing, and many other topics.  We also learned that it is currently Diwali (holiday) and we were graciously treated to some delicious cookies from Ram.

This was a fantastic get together and I look forward to many more.  Maybe swing these once a month?  Thoughts?  Any feedback would be much appreciated!

An open invitation to all - I’ll be at the Soy Luck Club in the West Village (New York) tomorrow (Saturday) from around 11am-3pm working on future media strategies and helping out other entrepreneurs. Feel free to come on down to the West Village and lets chat!Â

Would love to learn more about what your working on, be it entrepreneurial ventures, financing, advertising campaigns, etc.
Feel free to email me for my cellphone number to confirm tomorrow.

Many different brands are embracing Linden Lab’s Second Life including most recently Sony BMG, Reuters, Toyota Scion, American Apparel, and MLB (to name a few). However, what happens 6 months down the line when the PR buzz surrounding an integration into Second Life is diminished?

Lately, if your brand enters Second Life, you are almost guaranteed placement in the trade publications (ad) and the major newspapers (NYC article). Readers are getting tired of hearing about these integrations and the law of diminishing returns will kick in.

Is Second Life sustainable for your brands once the PR buzz wears off? That is the question. How do brands benefit from being in Second Life? There are just more than 1,000,000 registered users in the virtual world and roughly 8-10k logged in at any given time. Reach is not exactly ideal… so what is the benefit? If you are going after an extremely niche target audience of techno-geeks, science fiction, and content generators, then it may be ideal… but that’s a small subset of society. How sustainable is it for brands? Thoughts?

If you read any gaming magazine, online forum, website, or blog, chances are, you’ll come away feeling as if PS3 is doomed and that the Nintendo Wii will take over as the winner between the two of them. While the Wii may sell more units than the PS3 (or vice versa), one thing is being left out of all this pseudo-analysis…. the console manufacturers are targeting different audiences with them.

The Nintendo Wii is going after the casual to medium gamer who doesn’t want to spend a lot on a gaming system but wants to enjoy the entertainment surrounding it. Games will probably be on the cheaper end of the 3 majors and you’ll certainly see classic Nintendo games come back to life. With the Sony PS3, it’s targeting a much more hardcore gamer though potentially a bit less than the XBOX 360 and appeals to the technosaavy high-end gamer.

People all over the world are saying that the PS3 is doomed but remember, historically, Sony has sold plenty of Playstations and this is a flagship product for them. Also, Nintendo with it’s superb price point will sell well also. Research shows that console owners have more than one console - I’d assume plenty of people will pick up both a PS3 and Wii.

I received an IM today from a friend who works as a partner at a large Venture Capital firm who wanted to get my take on Paul Graham’s posting about 18 Mistakes That Kill Startups.  Paul, one of the founders of the Y Combinator, has put together a great outline of some common mistakes:

1. Single Founder
2.  Bad Location
3.  Marginal Niche
4.  Derivative Idea
5.  Obstinacy
6.  Hiring Bad Programmers
7.  Choosing the Wrong Platform
8.  Slowness in Launching
9.  Launching Too Early
10.  Having No Specific User In Mind
11.  Raising Too Little Money
12.  Spending too Much Money
13.  Raising Too Much Money
14.  Poor Investor Management
15.  Sacrificing Users To Profit
16.  Not Wanting To Get Your Hands Dirty
17.  Fighting Between Founders
18.  A Half-Hearted Attempt

I’ve been through most of these issues with my startups and ones that I am consulting with.  However, I’d say that #16 (Not Wanting To Get Your Hands Dirty) and #5 Obstinacy are the most common threads that I see these days.  Many corporate executives who want to get in touch with their inner entrepreneurial self have a tough time doing all the operational work that is required with a startup.  I can’t tell you how many times I’ve heard the phrases, "I need an assistant" or "Lets hire an analyst to do that."  Just get it done!

Obstinacy is also a big issue as many founders want to hold onto their ideas and don’t want to adapt to the marketplace.  You must embrace this.  As the current teenage generation is growing up, I feel that this will be less of an issue as they are always adapting to new technologies but it is still a common theme I have seen lately with startups.