Venture Capitalists and Entrepreneurs: The Same – Only Different

Guest post by Paul A. Jones of Michael Best & Friedrich LLP

Venture Capitalists (VCs) and entrepreneurs are a poster child couple for the notion of the love-hate relationship. Any VCs who have been around the block more than a time or two is certain to have their stories of inept, dishonest, and/or overwrought entrepreneurs. Ditto any entrepreneurs who have spent any serious time courting or managing relationships with VCs. And yet, the VC/Entrepreneur nexus is the greatest innovation engine the world has ever seen. Go figure.

It’s said that opposites attract, and in the VC/Entrepreneur relationship there is certainly some obvious opposition. When the dance starts, VCs have money, and entrepreneurs don’t. That surely makes for some serious mutual attraction, even as it is often a point of serious contention as well.

It’s also said that familiarity breeds contempt. That, I think, also goes a good ways towards explaining the friction that comes between so many VCs and entrepreneurs. They have more in common than either wants to admit.

As it turns out, VCs are themselves entrepreneurs of a sort. While VCs are in the money when entrepreneurs approach them as supplicants, most VCs get their money the same way the entrepreneurs courting them get theirs. They persuade a number of people who control a lot more money to send a small portion of it their way. The VC song and dance is based on pretty much the same sort of “invest with us and you’ll get rich(er)” narrative that entrepreneurs make when they pitch VCs.

This concept – the VC as entrepreneur – first occurred to me when I crossed over from the entrepreneur side of the risk capital table to the VC side. Before I even got settled in on the VC side, I found myself wrapped up in the same activities that consumed so much of my time as an entrepreneur: preparing a business plan and pitch deck, and knocking on innumerable doors in search of risk capital. Raising venture capital was pretty much a repeat of my entrepreneurial experience. And, it was equally as challenging and frustrating.

The similarities don’t stop there. As with entrepreneurs, VCs who have a track record of success find the money-raising process a lot easier than those who don’t. Real “newbies” to the VC game will find their capital raising campaigns much more challenging than folks who have “been there, done that” already – just as first-time entrepreneurs do. (Indeed, most of what are marketed as “first-time” venture funds include one or more partners who have had important and successful career stops at other venture fund management groups – just as most startups in the major venture centers include folks with experience at other high-risk/reward startups.) And just as entrepreneurs raising later rounds of financing for their startups, VCs raising post Fund I pools of capital will find that their likelihood of success is tightly correlated with the success of their earlier funds.

Of course, VCs and entrepreneurs have their differences as well. Two, I think, are the most significant when it comes to complicating the VC/Entrepreneur relationship.

The first is that VCs are coaches, while entrepreneurs are athletes. The VC role is to facilitate the success of their portfolio entrepreneurs: to make the entrepreneur’s job easier, and performance better. That is a huge difference, and one that trips up many a VC; particularly, VCs transitioning to the business from the entrepreneur side of the table. Few things can turn a VC/Entrepreneur relationship sour faster than a micromanaging VC who confuses supporting management with supplanting management. Or, an entrepreneur who won’t accept coaching.

The next biggest difference between VCs and entrepreneurs is that, in any given relationship, the VC is like the chicken at breakfast – very interested in the meal – while the entrepreneur is like the pig – fully committed to it. VCs look at deals as pieces of a puzzle: their success is tied to a portfolio of investments. For entrepreneurs, the deal is the whole puzzle. The singular focus of their attention, and measure of their success. Those different perspectives can make for very different levels of interest and commitment; differences that can generate a lot of misunderstanding and friction. It’s a lot easier for the VC/chicken to walk away from the table than the entrepreneur/pig.

And so, my thinking is that the love/hate dynamic that characterizes so many VC/Entrepreneur attitudes and relationships stems from a mix of similarities and differences between the two parties. Similarities and differences that, if properly appreciated by both parties, can help make their working relationships – and personal ones as well – more productive and less stressful.


Paul A. Jones, Of Counsel

Paul draws on his extensive business experience as a successful serial venture capital-backed entrepreneur, investor, and angel investor to represent emerging technology and life sciences companies, and venture capital firms in financing and other strategic transactions and general corporate matters.

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Michael Best & Friedrich LLP

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