VC Cliche of the Week
Q. What is the venture capitalists' favorite sight coming into his office?
A. A serial entrepreneur.
What is a serial entrepreneur? It's a person who can't stop starting companies. A person who has done it at least two or three times. A person who has been very successful at starting companies and enjoys doing it so much that they can't stop themselves.
I've said this before and I'll say it again. The raw material for venture capital is entrepreneurs. Without them, we have no business.
So the ones who are the most experienced, the most passionate, and the most successful are the diamonds of the raw material of the venture capital business.
I love serial entrepreneurs. I haven't met a VC who doesn't.
I was insprired to make serial entrepreneurs my cliche of the week by this blog post on Artists vs. Entrepreneurs. Here is the part of the post that inspired me:
there emerges a huge problem- entrepreneurs are indeed very much like recording artists- except they get far worse of a deal. Whilst painters, musicians and sculptors may have the opportunity to produce hundreds if not thousands of works prior to seeing maybe three or four become really valuable and accepted, entrepreneurs are limited by nature of their art to making maybe four to six works over their career.
Whilst of course the above is not news for anybody, this severe concentration of risk that entrepreneurs face is a huge, huge problem- probably not for the economy- but for entrepreneurs them selves. Can you imagine if the Beatles produced one record in the beggining of their careers and refused to make anymore because that make would mean they were unfocused? I think, over time, an approach that effectively deals with uncertainties faced by founders will creep in to become a more widely accepted way of doing business.
I agree with the person (in australia?) who wrote this post. The best serial entrpreneurs will probably figure out how to do more than four to six startups in their careers, but the four to six number is probably a good one to work with.
The upside for entrepreneurs on each deal is a lot higher than the VC's upside, but the portfolio diversification that VCs get is a lot more attractive than the "concentration risk" that the entreprenerus face.
This makes me think that serial entrepreneurs do it for the fun and passion not so much for the money. Every day, I wake up and thank god there are people who love starting companies so much that they accept the risk and go for it, time and time again.

Fred - you nailed it this time for sure! ;-) I started writing communications software back when I was 14 and released my first product for sale before my 16th birthday. At the same time I founded an online service (not a BBS, this was a planned competitor to Compurserve based on chat, forums, etc.) Nobody would fund me back then, so I ended up dropping the project, but it set the seeds for my future. This continued on and off through college where I dropped out and started my internet company in 1991. In '94 I started the first ISP in NE Wisconsin and spun off one of the first pure interactive web development firms in late 94. (they're still in business today working with the NFL and other Fortune 1000 customers). My current email security company I founded in 1999, and soon afterwards I sold my ISP as it wasn't a good portfolio fit anymore and I could get a better ROI by moving the cash assets into my email security company.
My wife both loves and hates my nack for starting new companies. I'm more selective today than I used to be, but my little back book has tons of ideas for new businesses - all from where I see "friction" that a new company can reduce and make market share for itself.
My employees also share this philosophy and the development team is always looking at other ways to leverage our technologies into other markets, etc.
I'm not like most other folks I see trying to raise VC monies.... even if I don't raise money, I do the businesses that I plan. Typically I'll rish my own money in the early stage development evolution of a software company and when we've created the product and it's a viable product for the market, then I go seek VC funding to take it to the world.
Fred - I'm sure you might disagree with this bootstrap methodology, but I think it has forced us to be lean and mean in terms of burn rates, expenditures, etc. so that when we do get funding we properly utilize the cash to it's greatest ROI.
David
Posted by: David | May 18, 2005 at 09:08 AM
i don't disagree with bootstrapping. i think its the best way to build a business. vc money is too dilutive to be used unless you have really need it.
Posted by: fred | May 18, 2005 at 10:23 AM
Fred - I agree. Now we're to the point that we need additional funding so we're doing a (small) round. Being that the funds needed are small ($2M) we're going with individual investors and not organized VC. Even though we're not talking to organized VC, they're calling with the mindset of "as long as your raising money, and you can get $2M, you can easily get $4M, which means we want to talk to you about this round."
I see where they are coming from, and if we can raise more money in the same timeframe, the question I need to answer turns to, "You know what you can do with $2M, so what could you do with $4M or $5M? Can you acheive results faster and/or get more market share as a result? And what's that worth to you?"
Am I missing something?
David
Posted by: David | May 18, 2005 at 12:09 PM
Fred -
Have you read Paul Kedrosky's post on The Myth of the Serial Entrepreneur? He tries to explain why the much-loved serial entrepreneur is in short supply, at least among people seeking VC funding. A snippet:
I'd be interested to hear whether this breed is as rare as some people think...
Posted by: David Gilford | May 18, 2005 at 02:40 PM
I posted yesterday on my blog (broadwayfrontofhouse.blogspot.com - dedicated to the Broadway Theatre Industry) about producers who face the occasional failure and the occasional success who are somehow able to get right back on the horse - and how strong they must be to be able to do just that. Thinking of them as serial entrepreneurs - which thanks to you I realize they absolutely are - suggests that they do it because they have the passion, the love, the need. They still might be crazy, but where would I be without them?
Posted by: Jeff Matisoff | May 19, 2005 at 10:05 AM
Fred,
I'm a couple of years into my third venture. The first two exited successfully via acquisition. What keeps me coming back? It's pretty basic, actually - I'm a builder ... of software, of teams, of companies. There is something in a venture about balancing creativity and science that has just the right symmetry for me. And the fact that I have had the same incredibly talented co-founder in all three companies has been a huge motivator to jump back in at the conclusion of our prior projects.
I've learned things about myself over the course of my ventures (or "adventures", as my father, a lifer at Polaroid, refers to them). Among those lessons, I've come to believe that fretting over risks and rewards is mostly a waste of time. These are "leap of faith" topics. A person either has, or doesn't have, the cast iron gut to tolerate massive risk. I believe that risk preferences are pretty much baked into peoples' DNA, and entrepreneurs with high tolerences don't burn a lot of cycles thinking about risk.
As a first-time entrepreneur, I often thought about reward senerios. After a while, though, I got tired of doing the math and figured out that building things and helping them to grow was much more satisfying. My obsession about potential rewards was replaced by an obsession to work with really smart, creative people to solve really thorny problems. I've never looked back.
My point in all of this is I do believe that some people are wired from the get-go to try their hands at a venture. Of those, the ones who are most likely to jump back in are those capable of internalizing the lessons that are born from failure and success, because that knowledge makes the next building experience even more interesting. Entrepreneurs whose primary motivation is money are less likely to return for another bite once they've achieved their financial goals.
Fred
Posted by: Fred Holahan | May 19, 2005 at 02:33 PM
Speaking of serial entrepreneurs, there's a site for them at www.startupjunkies.org.
Posted by: Beef Jezos | May 19, 2005 at 11:30 PM
There is an overlap between people with a taste for doing business and people who have are drawn irresistibly to do things which nobody has ever done before.
As you observe, it's not very large.
Happily into my fifth decade, three years into my fifth start-up, just days away from finding out if it is going to work.
A way to lay off some of the risk sounds nice, but this time around I was offered that and turned it down.
Actually I think it's more accurate to say that giving up more control, even to our very friendly VC who has invested in me before, seemed like an increase in risk.
I enjoy your blog.
Posted by: ZF | May 20, 2005 at 09:00 AM
"... they can't stop themselves."
That resonates.
Each of the startups I've done, Restaurant City, Silicon Alley Reporter, VentureReporter.net, and WeblogsInc.com, I had no choice but to do. Once my mind got working on them I couldn't stop myself.
My belief has always been that being delusional is one of the biggest assets a entrepreneur can have... you really have to believe that what you're doing is going to happen. You have to look at it as if completing the mission is your destiny.
Of course, there is something to be said about VCs who can't stop placing bets on people. :-)
I mean, you've never thought about starting a company right? So, in some way your a compulsive gambler.... you really believe in people--you want to believe in people right?
Except VCs in some ways they are coaches betting on their own team. They want to find Michael Jordon, back them, and coach them.
The best VCs are addicted to setting up the situation in which people can win... like Phil Jackson or Pat Rielly.
We're all very, very sick people... but what else would we do with ourselves?
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