May 5, 2010
It’s not about homeruns. It’s about more at-bats.

There’s been much talk in the Boston entrepreneurial ecosystem
about the need to get more entrepreneurs building great companies and
how the community can support them. Bill Warner kicked this discussion
off with a great series of posts.
There was much follow-on debate at the Mass Technology Leadership
Council and then most recently at the Nantucket Conference (according to
Twitter anyway!).

For some reason this analogy and its implications – swinging for
the fences - and the whole onslaught of follow-up didn’t sit well with
me. Not sure whether it was the analogy or what, but I felt like the
solution – we need more homeruns - didn’t precisely address the problem.
And while I greatly admire all the folks putting stakes in the ground
on this issue, I wonder whether as entrepreneurs in Boston we’re really
focused on building the next billion dollar idea, changing the game or
“the world.” That’s a lot of pressure and sets a level of expectation
for what a “fundable business” is that I’m not sure it serves the
community so well.

I’ve always been one to want to go big, but equally important I want
to stay in the game. Persistence does payoff according to all
the research
over at the Harvard Business School and that first-time entrepreneurs
fail at a staggering rate of 93%. So with those kind of odds, you can
see why a lot of entrepreneurs always have a shelf of other ideas and
plans that run beyond B to G and H.  Being an entrepreneur
is a repeat game.
And in repeat games you need multiple at-bats. This is where being a
Boston entrepreneur becomes a problem for me, it artificially suppresses
my on base-percentage over the long-term.

This all got me thinking about the costs of failure. For which there
have also been a staggering number of posts recently. The “fail fast”
movement took a beating from Mark Suster here
and then everybody fell into line around the simple notion that “fail
fast” wasn’t quite the right idea but rather that “fail smart” was the
whole point.

So really what we want is entrepreneurs who take risks and fail
smartly (i.e. they try to change the world with real products and pivot
as needed). Nobody seems to disagree with this. The problem is that it’s
just a whole lot easier to fail in Silicon Valley. I don’t want to go
all Tupac-Biggie on
you right now – I think Matt Mireles did a fine job.  But
the fact remains, you show me an entrepreneur with a truly innovative
idea (this is especially true in consumer internet) that requires a
significant “suspension of disbelief” from investors and I’ll show you
an entrepreneur moving to the Valley.  I’m sure there are
exceptions; I’d love to hear about them in the comments.

My point is really about the safety of failing in the Valley. It’s
almost a rite of passage. The stories abound about this company not
working, but then so and so stumbled into this guy in this bar or this
coffee shop and then shit, they built X. You get more street
cred for having failed.  Maybe it’s a folk tale. But you
know where folk tales come from? Tradition and culture built over
generations. The thing is, in Boston when you fail there aren’t a
hundred or two hundred other companies to go work at or a thousand
founders in coffee shops all over the place looking to “do it all over
again”. You could practically throw two darts at University Café in Palo
Alto and be sure to hit one Angel and one Entrepreneur. This is
certainly changing in Boston, but we’ve got a long way to go.

So while I love the idea of thinking big, going big and punching
above our league-tables (if there’s one thing I love about
VC/Entrepreneur blogs it’s the persistent use and acceptance of mixed
metaphors) I think the community would also be served by thinking about a
support mechanism that builds the network between entrepreneurs even
wider so that the thought process when deciding where to start a company
is this “shit, I think I’ve gotten something here, but ya know if it
doesn’t take in 9 months, I will have found 10 other companies to work
for until I start my next one…” instead of “shit, if this doesn’t work, I
might have to take a real job…”

We don’t just need more home-runs we need the chance for more plate

James Reinhart is a
Co-Founder of thredUP in
Cambridge, Massachusetts.  This blog post was originally published on
May 3, 2010.  You can find this post, as well as additional
content on his blog called Hanging by
a thred