I’ve had several interesting conversation following the article on negotiating a better series A deal. Entrepreneurs write and ask for advice on a specific situation. Unfortunately, it’s really hard to give specific advice in these cases without a fair amount of additional information. There are too many variables and a lot depends on the goals of the entrepreneur.

I wish there was a standard questionnaire, like one of those pop psych personality tests, that entrepreneurs can fill out to get the background information out. However, I’m not interested in whether someone wants to be an entrepreneur (they are rarely talking to me if they are not entrepreneurs already). I’m more interested in what they consider a success, what type of company they want to build, the impact they want to create, etc.

Here is some of what I’ve found.

• Personality tests for entrepreneurs
• Online personality test for entrepreneurs

Have you found a test you’ve liked? Have you seen a test that goes after what I’m interested in?

A few days ago, WSJ’s startup & VC blog referred to an NVCA study where entrepreneurs complained about the lack of operational experience in some VC board members.

I’ve been an entrepreneur as well as a VC. The biggest travesty that VC firms can visit on a portfolio company is putting an inexperienced representative onto its board. Too many VCs have no real operating experience (sorry, having been a I-banker or recruiter does not count as experience).

I think this is an overly simplistic way of looking at things. Here is a quick test. Which one would you choose as your VC board member for your pre-product Series A startup:

• A really experienced former CEO who can’t get used to being a board member and thinks he can run the company better than you
• An really experienced former head of sales who has scaled companies from $10M on several times but who has never been in a pre-product startup
• A former lawyer or banker or accountant who’s had more than a decade of experience as a VC and a fantastic early stage investment record.

Not sure about you but, assuming the personalities work out well, I’d go with the VC w/o operating experience any day of the week. In fact, my first startup, Allaire, went exactly this way.

Two take-aways:

1. Comparing between board members is very, very hard. Especially if you don’t have competing offers to compare. Do not underestimate the impact that your investor board member will have on your life. First and foremost, talk to good people with good track records. Do not get tempted by the cash. I know this is very hard to say in the abstract but it is true. Go talk to CEOs of companies who’ve had a serious falling out with their investor board members. Listen closely to what they tell you.
2. There is no simple rule of thumb for comparing between investor board members. The key is to understand what you are comparing. You are not looking for a CEO or an exec. You are looking for one board member who’s part of a larger board. Boards are about strategy, governance, fundraising, exits and supporting the CEO. They should not be a crutch for your team, unless this is by design, e.g., with an executive board member.

from Start-Up CEOs Gripe About VCs’ Lack Of Operating Experience – Venture Capital Dispatch – WSJ.

A comment on my recent post about social commerce pointed to the Wikipedia article on social commerce, which was started in September of 2007, according to the history. Which is funny because I started the first Wikipedia page on social commerce in December of the previous year but, despite the help of multiple friends interested in the space, we couldn’t prevent the Wikipedia police from taking the page down. The reason for the takedown was that they wanted citations and not just of blogs and links to startups that were in the space.

Wikipedia is nearly infinitely more flexible and up-to-date than its precedessors–the multi-volume encyclopedias. Yet, still, here is just one example of how it refused to accept new knowledge because it was stuck on looking for validation from the very same backward world of paper.

Google just nabbed AdMob for a handy $750M. Congrats to AdMob founder Omar Hamoui who got into the space early and executed very aggressively. More details on the acqusition here.

The background story here is of the explosion in mobile browsing and mobile applications driven by the iPhone. That s what fueled a lot of AdMob s growth in the past 18mos. I was at a dinner with Omar about a year ago. He had the numbers in his sights and predicted growth will accelerate.

This is mixed news for the other players in mobile advertising. The gap between the largest player and the next one down just got much, much bigger. Key takeaways:

• Google s reach with advertisers and their targeting technology are likely to improve the performance of the AdMob network measurably. It s difficult to see how others can compete meaningfully on scale.
• Startups main advantage is technical innovation and business agility. Both should be severely discounted in mobile where, in addition to the device & network fragmentation, operators and app store owners exert a significant degree of control which, often as an unintended consequence, slows the pace of innovation.
• There is an opportunity to shift competitive advantage from volume to quality as Quattro has done but that s a tough business to scale even in a growing market. In the end, the biggest risk here is that large players such as Google can always buy your customers with guaranteed minimums.

It s time for mobile publishers to take more control over their inventory by looking at players such as Nexage.

I got credit for a great post on social commerce I didn’t write.

As for whether 2010 will be the year for social commerce, I’m not sure. I think 2009 really accelerated the social advertising trend. Some of my posts are here.

Social commerce still has a ways to go. I named this as a key e-commerce 2.0 trend back in 2006 and didn’t explicitly distinguish it from social advertising. I should have.

Well, it seems that the Mike Arrington’s pointed critique of social marketing practices is getting even the very large players to move quickly.

Today, we’re adding a fifth principle that clarifies a specific use case that we feel is particularly damaging to the user experience: promotions that include hidden renewals without specific opt-in will not be permitted. Because it’s our belief opt-out offers are misleading and do not have the best interests of the users in mind, we will be updating our Terms of Use this week to better clarify this for users and developers.

via MySpace Says Zero Tolerance For App Scams, Changes Terms Of Use

There is a simple principle at work here. Visibility is key. There are many shady things quietly going on on the Net today.  Once someone shines a big, bright light it becomes harder to hide. Everything starts with visibility.

I visited Facebook’s new space a few months ago. VPE Mike Schroepfer gave me the tour. I did like it a lot, although I found a few of the areas quite dark. Maybe it was the jet lag. See the link below for an awesome visual tour.

SU – Facebook Headquarters by Studio O+A & CONTEMPORIST

Space can have a profound effect of culture, communication and productivity. Unfortunately, most entrepreneurs don’t think (or perhaps know how to think) about this enough. Make it a priority. It doesn’t have to be expensive to be good.

Yes, your startup won’t have as much money to invest in its space but that doesn’t mean you can’t create a really cool environment. Agile methodologies have helped spread the concept of more open office spaces. With less to spend on buildouts and partitioning systems there is more to spend on making the space project the energy and culture you want your company to have.

You’ll find two great examples of good spaces that didn’t cost that much in Boston at Allurent in Cambridge (which also houses Polaris’s Dogpatch Labs) and Visible Measures in Boston.

Who else’s space do you really like?

In some markets, the presence of even a few players willing to do shady business can have a profound effect on the ecosystem. Advertising, particularly the hard ROI kind, is one of these markets.

Here’s what ad networks struggle with—to either run what ads make the most money or else be forced out by other ad networks willing to be shadier than them.

via How To Spam Facebook Like A Pro: An Insider’s Confession.

Every conference having anything to do with entrepreneurship and venture capital has the obligatory “pitching & fundraising” panel. I’ve been on enough of them to have a sense of how disappointing they can be for the audience. Experienced folks hear the same old cliches with a slight twist based on the current environment. Newbies find what they hear random and mostly inapplicable to their attempts to raise money. So it may be a little surprising that when the organizers of the MIT Emerging Technologies Conference asked me to moderate just that type of panel I was excited to do it. The reason is that we’ll try to talk about pitching and fundraising in a different way. This post explains how and why.

First the details.

• The event: Tue-Thu next week (September 22-24) @ MIT. This is part of the Lab to Market workshop.
• The time: Tue @ 3:45pm at the Kresge Auditorium
• The panelists:
  • Bill Aulet, serial entrepreneur who’s run an Inc 500 company now at MIT
  • David Frankel, entrepreneur and super-angel now at Founder Collective, a new seed fund in Boston
  • Jeff Glass, former CEO of m-Qube now at Bain Capital
  • Rich Levandov, co-founder of Phoenix Technologies now at Avalon Ventures
• The details: follow @simeons and you’ll know

The secret to why we’ll do things differently lies in data. I asked the conference organizers to survey the audience about the types of financing they were interested in.

• A whopping 55% want to know about very early stage, non-VC financing (bootstrapping, customer-financing, pre-seed, seed, angel)
• Only 18% (1/3) were interested in early stage financing from traditional VCs (top-tier and smaller funds)
• 10% are looking to Uncle Sam for money
• The rest want to know about follow-on financings and M&A

At previous events, when I’ve asked about the split between VC and non-VC early stage financing the interest has been about evenly split. Here it’s 1 : 3. Is it just the MIT audience? I doubt it. More likely, the change is due to a big shift in the nature of startup creation as a result of the drop in the cost of building and distributing high-tech products and services. This is especially true of Web and cloud-based businesses but is also affecting life sciences and cleantech. (For more on that, stop by the panel I’m doing on cloud computing on Tuesday, the MTLC Innovation unConference on October 1st and by the Democratization of Innovation conversation Ray Kurzweil and I will have at the MIT Enterprise Forum on October 14.)

It’s a good time to have  a conversation about what’s the right funding path for companies and the value-add of various investor types. The dialog has been heating up. The NVCA recently made some outlandish claims about the economic impact of VCs. TechCrunch responded with a guest post from Vivek Wadhwa. The summary is “when things go well, VCs take too much credit.” My two cents are that if VCs are guilty of claiming or receiving too much credit when things go well, they certainly get too much blame when things go poorly. And I certainly think it’s foolish to only blame VCs for investing too much money in companies. It takes two to tango. In the background there is the “the venture capital industry is broken” refrain delivered by groups with alternative investment models and Bill Gurley’s data-driven commentary (the strong will get stronger, the weak will find something else to do). All in all, a great setup for a no holds barred discussion about fundraising.

I recruited the panelists with the audience’s interests in mind. They have all been successful entrepreneurs. They all are or have been investors and they all know early stage well.

Come armed with hard questions and help make this a great event.

I’m excited to join the Entrepreneurs in Residence at the MIT E-Center. It’s a new structure for fostering innovation and venture creation pushed forth by Bill Aulet who runs the center now. I’m fortunate to be doing this with great group of entrepreneurs including:

• Susan Whoriskey (Cubist Pharmaceuticals, Momenta Pharmaceuticals, Whoriskey Associates)
• Jean Hammond (AXON Networks, Quarry Technologies, Spider Systems, ZipCar, HubAngels)
• Brian Halligan & Dharmesh Shah (HubSpot)
• Roger Freeman (Solventera Energy)

Having been involved with MIT for years in various ways, I look forward to more regular contact and engagement.