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I was honestly unaware. Drunk on the kool-aid maybe? Arguably as a company they were much more mature when they took funding relative to the target market for the book, and many posts on the blog advising to stay away from funding, and to not quit your day job.
http://gettingreal.37signals.com/ch02_Fund_Your...
If you are doing something innovative I think it's much better to create a space and attract investors to it than to enter one awash with startups doing very similar things.
I think one of the difficult things about being in a more stagnant market is that the market is not as receptive to change, which is one of the main advantages of a startup company. Once you start supporting customers / users (if you can even get them), it's real pain to the young company to try and pivot to a bigger market or adjacent space. In more dynamic markets where things are really in flux, customers seem more willing to let you guide them to the opportunity (witness the huge variety of social media dashboards for the enterprise and how often they change).
I think this is a great post-mortem as to why some VC's weren't so hot on your idea; however, you did raise money, so not all VC's thought the way you describe above. I think it would be great to contrast what your investors saw in your business and why they decided to invest. Did they see something in the business that others didn't see? Did they invest because they believed in Charlie? etc..
The more I learn the more it seems to me like an entrepreneur should focus on creating value in their specific industry or market. You saw a huge opportunity in the career path market and you went after it. Once you are able to breakthrough and start to show value then VC's, investors, advertisers, users and partners will come. I do agree that it is difficult to gain momentum (and raise money) in certain sectors, but perhaps there is more room to maneuver because there is less competition. If you pick a trendier sector, perhaps there will be that many more start-ups trying to do the same exact thing as you.
Did you try raising money from people or companies within your Industry who saw the same opportunity as you?
One of the things that keeps me excited about Sportsvite is that we're in a market, within the greater sports media market, where there is pretty much a void -- adult recreational sports. It's not as hot as fantasy, high school or pro sports. We often talk with big media companies that don't see rec sports as part of their strategy right now (and usually ask about high school or youth sports). If we can continue to prove that the opportunity is as big as we think it is, and can unlock some of that value, I believe we'll be in a great position with investors, partners and users. To do that, I really think we have to focus on the "unsexy" parts -- helping league organizers promote, helping teams organize, making it easier to find people to play with. At times we've been distracted by what partners, investors and advertisers want right now to help them achieve their objectives or strategies.
Keep up the posts about Path 101. They are great and I really enjoy reading them.
that you were in"
Unfortunately, my industry sucks and people were content to keep doing
things the old way. :)
On this topic, I enjoyed this old post from Nabeel Hyatt (a great guy who runs Conduit up in Boston):
http://nabeelhyatt.com/post/121840284/navigatin...