Union Square Ventures and a new kind of Venture Capital firm.

Yesterday’s, NYTimes article on Union Square Ventures (USV) entitled “A New Kind Of Venture Capital Firm” is an interesting read and I’m glad to see the media beginning to pick up on this.

I’ve been following USV for a whlie now and actually interviewed Brad Burnham in preparation for a session at the Open Everything Retreat on Investing in Open. They seem to have a knack for investing in webtech ventures like Twitter and Wesabe that have models that can be deeply disruptive to the systems they are taking on and where the question of how they are going to make money from them is far from answered. And now they’re turning more of their attention to conventionally ‘social’ issues including education and the environment.

Coming off my latest exploration of the social venture capital sector, I’m looking forward to seeing USV coming into this space – and I don’t think it’s much of a stretch. Investments like Twitter and Wesabe are not too dissimilar from making investments in social change and innovation. Both are venturing toward systems level change – and come with a high degree of complex ambiguity.

At the same time, we are beginning to see a new mode of organization taking shape that challenges how ventures are built and therefore how we invest in them. Where all of these things come together is where I’m betting we are going to find some deep innovations on the new kind of venture capital firm I think USV and others are all working their way towards.

In the meatime, if you’ve encountered – or are thinking of – any innovations in this area please pop them in the comments or over in the public wiki on ‘Investing and Open‘. I’m playing with some ideas myself and will be adding them in there and here on this blog as they develop.

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The dynamics of the frontier: complex ambiguity

The frontiers of venturing are the places where conventional venturing and planning approaches become least effective. It is the effective limit of conventional approaches to venturing that define the edge of the frontier with the deepest depths of the frontier being the pre-concept stage of a systemically focused venture.

Conventional approaches loose effectiveness the earlier a venture is in the development phase because of increasing ambiguity.  The less that is known the harder it is to do linear modeling and planning.  Choices made continually reduce ambiguity as the venture moves along the development and into the realm where conventional planning approaches can be effectively used.

On the depth axis, the more systemic the purpose, the greater the complexity. As the system changes, so will the problems and opportunities being addressed as will the community addressing those challenges and opportunities. The interrelatedness of planning decisions and planning context can be an all consuming black-hole. The more you are trying to shake things up, the less you know how things are going to shake out.

While all ventures face a degree of ambiguity, the depth of your foray into the frontiers depends on the depth of complex ambiguity being taken on – a function of complexity and abmiguity.  Conventionally, managing this is accomplished either through blind faith in the entrepreneur and management team or by reducing the complex ambiguity by advancing the planning horizon and responding to situational opportunities and problems. Taking the latter approach often serves to reduce near-term operational risk but also severely limits or eliminates the potential for achieving systemic level impacts, while the former approach is limited by the abilities of the entrepreneur/management team in the unique situation of this specific venture. Neither option suggest even modest probabilities of success particularly at the depths of the frontier… which describes the venturing and venture investing community as it currently operates.

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