Something Ventured by x7lpXA6w


									Something Ventured

October 28th, 2005

Ambition Recognition

“Only shooting stars
Break the mold.” – Smashmouth, Allstar

Eighteen months ago I wrote about leaders
( and it was
referenced as one of my better columns by some of you. In fact, it will
be referenced in a book soon:

Dear Mr. Holliday,

I am an American law professor writing a book on women in combat. I
have been reading some of the leadership literature and came upon
your column from last year entitled "Born Leaders." I thought your
column had more wisdom in it than 99% of the academic literature. If
you have no objection, I would like to quote the excerpt below in my

Best regards,
Kingsley Browne

{I didn’t add the excerpt, but it was the part about employees being
able to smell a bad leader.}

In a follow-up to that column, which was oriented very much as a
lecture on leadership, I wanted to look at the same issue again solely
from the eyes of investors. I have been asking those in my industry
and those that invest (angels) about the criteria that they want to see
in a “backable” CEO and more specifically, what they have learned
through good and bad experiences in trying to identify the right

The biggest issue we face is that we see great technology
opportunities and large market opportunities, but experience (usually
bad) has taught us that the number one factor is whether the
management team, mostly the CEO, has the strategic and tactical
capability to take the idea to the moon. Can this person in front of
you hit it out of the park when they have never done so before?
Forget the Paul Terry, Adam Lorant, John Seminerio threesome that
has done it twice already. That’s a no-brainer. I’m talking about the
bright-eyed entrepreneur with no start-up-to-the-moon track record.

First, some legendary anecdotes about backing a CEO with no previous
proof of capability:

Arthur Rock invests $60,000 in Apple after meeting Steve Jobs and
attending the Home Brew Computer Show in San Jose, seeing the
wild-eyed enthusiasm of the computer crowd around Apple’s booth
(1977). Rock would say that he had his doubts in the first meeting
with the un-shaven, sandal wearing guy whose diet at the time
consisted entirely of fruit. Jobs’ first business plan called for $500M in
revenue in ten years. He had never run a company before. To be
honest, Rock based his decision to invest on Mike Markkula, Apple’s
first angel investor and former Intel executive who would help them
with marketing. But he did see the un-believable passion in Jobs and
considered the support he had around him and bought in. By the way,
they reached $500M in sales in 5 years.

From John Battelle’s new book about Google, “The Search”: In August
1998, Larry Page and Sergei Brin sat on the porch of a Stanford
professor’s house and showed Andy Bechtolsheim (founder of Sun,
among others) their search engine. Andy asked them a bunch of
questions and then said “‘Well, I don’t want to waste time. I’m sure it’ll
help you guys if I just write a check.’” He headed to his car to get his
checkbook and Brin and Page were left to figure out a) at what
valuation and b) who to make the check out to because they didn’t
have a company yet. Andy was acting in the true angel investor spirit
and, to be truthful, was focused on the technology opportunity rather
than the team in front of him. But his decision to back these guys
sprung from the fact that others had backed him, Bill Joy and Vinod
Khosla in the early 80’s to start Sun Microsystems after none of them
had started a successful business to that point. Good decision. Based
on the valuation discussed that day and subsequent dilution in the VC
rounds, if Andy was still holding all of his stock, it would be worth
about $10B today.

Of the conversations I have had around BC recently, the best term I
heard about how to recognize whether a person could be a winner,
even without proof at the start-up level, was “vaulting ambition”.
Passion is critical, but having that passion tied to huge ambition
seemed to be the right formula for a venture type of bet.
My favourite pop-culture reference to “vaulting ambition” would be
Plankton from the Sponge Bob Squarepants cartoons. For those of
you without the 8-16 year demographic in your house, Plankton is,
well, a plankton with a huge booming voice and massive ambition to
be the leader of the underwater world, via his restaurant, the Chum
Bucket. In essence, he is the evil figure and nemesis of Sponge Bob.
He is convincing, despite his stature. He persuades those around him
and inspires their loyalty. He has big dreams and even bigger drive to
deliver the goods. Alas, bumbling SpongeBob always de-rails him, but
that part doesn’t fit my analogy…

Simply stating your ambition is not enough to qualify. In the absence
of proof of previous success, qualifying the ambition with solid
analysis, strategic insight and a believable implementation/operational
plan… that is what impresses. You may say you will do $500M in ten
years (everyone does), but the investor sees the ambition, hears the
plan and believes. Plankton, but with a plan. Angels will write the
check right then and there.

Institutional investors need to go back to their group and convince
them that this is a person to back. What you want them to say around
the board room table back at their office is that the entrepreneur “gets
it” and clearly has the ambition to drive it forward. You want them to
say, “I know they haven’t done it before, but this guy’s/gal’s a winner.
I can feel it.” They will have to justify backing the entrepreneur
without experience and you can help them do that by surrounding
yourself with good advisors, board members and other team members
that have been through start-ups before.

Far too often, we (the investors) make mistakes… but that is the game
we play. We bet on the wrong people or the wrong technology or the
wrong market. Our successes have to make up for those mistakes
(and more). In the downturn, we started to equate failure with
inexperienced CEOs. We have equated mediocrity with failure to
execute by our management teams. In some cases, this is true, in
others, circumstances got in the way. The unfortunate by-product of
these painful lessons is that we don’t give the un-proven entrepreneur
a chance.

To help make the decisions, some institutions use HR professionals to
quantify the characteristics of un-proven CEOs to see if they match up
with successful entrepreneurs. Some investors choose to stay with
their “gut”. Either way, it is incumbent upon all investors to recognize
deficiencies that might come from inexperience and decide if the
opportunity is worth the effort to manage them. That’s the key folks…
we can look at inexperienced entrepreneurs if the opportunity is
exceptional. Once again, an anecdote for this is Don Valentine’s initial
investment in Cisco where the founders were a husband/wife team
that everyone else had rejected (basically everyone thought they were
nuts). He was willing to work with and around them because of the
opportunity he saw.

Now there are plenty of good business opportunities to make some
money that don’t require an entrepreneur with “vaulting ambition”.
Operational skills to execute a plan successfully can exist without
Plankton-like ambition. Frankly, only the big opportunities need that
kind of energy and drive. I heard plenty of examples where
entrepreneurs may have lacked start-up experience, but turned their
skills learned in other environments into decent companies. But there
was consistent theme among the big winners…

Perhaps I can give you, from my very un-scientific poll of investors in
BC, my Plankton Hall Of Fame for those entrepreneurs among us who
may not have been there before, but whose backers recognized the
“vaulting ambition” to be enormous and they succeeded (feel free to
send me others who you think may fit. I surely will miss some as I did
not survey everyone):

Amos Michaelson - Creo
Dick Hardt - ActiveState
Don Mattrick – Distinctive Software
John MacDonald – MDA
Norm Francis – Basic Software Group
Geoffrey Ballard – Ballard Power
David Sutcliffe – Sierra Wireless

Not every on of these was the founder, but without a huge success in
their background for an investor to latch onto, they inspired investors
to bet on their big idea and then succeeded. For each Plankton listed
above, there are ten who had the big idea and the ambition, but failed.
But it should not stop us from recognizing the “type” and backing
them. It would be a shame to miss one.

I look forward to your comments.

Letters From Last Time –
Wading into the debate about Web 2.0, as I did last time, and
delivering an argument that it is not a revolution, but an evolution did
cause me some grief among the “technorati” that have adopted Web
2.0 techniques. First, there was the blogs
for instance) making fun of my Web 1.0 column and manipulating
Google search results on my name. Then, there was the VEF event on
October 25th, where they mocked my response and my Google
“identity” in front of a few hundred colleagues. (BTW, Nick and Dick
should be commended for the best VEF event I have been to in 12
years of attending!!!) All of this reminded me of the apprehension I
had writing the column in the first place… that writing on the web
somewhat negatively about people that seem to be permanently
attached to the web and, therefore, are zealous about its apparent
transformation… well, let’s just say it was like standing in front of a Klu
Klux Klan rally and telling them that their pillow case hats look
ridiculous. Burning crosses on my lawn would be just the start of my

Here is what others said in response to my column:

Once again you hit this one dead on Brent.

All these opportunists are looking to make a new play with other folk's
money. ("It’s different this time!") If it was this easy to make a buck in
investing then value investors would not have a play. I am willing to
wait to see this play out.


Hi Brent,

Not sure if you remember me but I used to run Helix Internet, one of
the first ISPs (since then I have been running various ISP/Hosting
companies sales & marketing - the latest Superb Internet). - but
finally got burnout out on the "much ado about nothing" aspect of the
Internet and Web 2.0 is just another example so finally hung up my

Anyways well said and agreed "their time is up"!


…should be an interesting event on Tuesday – I’m already exhausted
with this 2.0 crap. Yes, my newsletter has an RSS feed, I regularly
read blogs (here’s a good posting), we’ve even sent out a few
Podcasts. The technology is wonderful, but I’m not impressed by Flickr
shots of what’s in someone’s briefcase. I’ll leverage some if it makes
me more effective, but the earth is still gonna be tilted the same way.
Shouting louder doesn’t make the message any clearer for those that
are still waiting to hear the real point.

Had lunch yesterday with a few peers, and reveled in all the senses of
rich intellectual interaction and good food (and not blowing my eyes
out in front of 2 computer screens simultaneously).

…wonder how many “Web 2.0 Kool-aid” tickets could be sold at
Tuesday night’s event? Could be a great fund-raiser for a local charity
– I’d certainly be in for $5… ;-)

Nice article.

Hi Brent

I wish you would add RSS and trackbacks to your column. Not sure
why you and Mike have not shifted this to a blog format, it would help
to build the local community if you did so. Anyway …

Regardless of the hype factor of Web 2.0 and its relevance in making
investment decisions (something I will leave to you), the key patterns
that O’Reilly identifies are useful and we certainly use them to shape
strategy at Recombo.

      Services, not packaged software, with cost-effective scalability
          o Key business principle of the Recombo Connector, which
             provides integration middleware as a service
      Control over unique, hard-to-recreate data sources that get
       richer as more people use them
          o Every time a user adds a content type to the Connector
             this enriches our ability to handle new content types
          o Collections of competency models mapped against content
             catalogs are a growing part of our revenue stream and we
            are working to turn this into a Connector service, our IP is
            the mapping and not the competency model or the content
         o Every time we touch a web service we catalog and
            represent it for future integrations
    Trusting users as co-developers
         o Our users tend to be other companies and we are deeply
            engaged in web services development – our goal next year
            is to open this up so that Recombo becomes an open
            repository for web services
    Harnessing collective intelligence
         o This is what is happening with the content types, the
            competency to catalog mappings and from next year with
            the web services
    Leveraging the long tail through customer self-service
         o Need to work on this
    Software above the level of a single device
         o What middleware as a service enable
    Lightweight user interfaces, development models, AND business
         o See comments on REST vs. Web Services stack.
The REST vs. Web Service debate is also something we struggle with.
Our current system is a mix, RESTful where possible and web services
based where a tighter enterprise style integration is necessary. It is
going to be a technical and strategic challenge to manage this
Anyway, I hope you are stimulating thought and discussion in the local
business and investment community. Any chance of getting other local
VCs to publicly comment on Web 2.0 – guess I should go to the
Financing Forum to hear about this.


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