I agree with you 100%. My initial goal was to represent a perspective on the relative pros/cons to both and point out that for most companies, there is a time to consider either approach. Regardless of the ultimate direction, bootstrapping teaches you invaluable lessons that will make you a stronger entrepreneur if/when you decide to raise. Our personal experience was that after bootstrapping for a while, we encountered several obstacles based on our product vision, skill set and market that raising helped us overcome. I wouldn't suggest that this is the case for everyone: different calibrations of founders/products/verticals might have very different equations for success.
I use a PC with Windows 7. I have a Macbook but I'm not crazy about the Office apps on Macbook so use the PC most of the time.
This past week, I spilled water on the PC and took it into the shop. I picked-up a back-up ASUS, loaded with Win 8.
This was the beginning of my nightmare.
1. Win 8 was just terrible. It took me way too long to figure out how to perform simple actions. Win 8 is Frankenstien - it is Microsoft's attempt to unify the computing experience by (a) copying numerous OS UI elements; (b) slapping a tablet version of their operating system on top of a desktop version; (c) burying elements behind keyboard shortcuts and some gaudy, horrible startup screen that advertises other Microsoft products.
In a nutshell, they have built the perfect operating system for a schizophrenic blind person.
After a day of cursing out Microsoft while trying to figure out basic things (like getting to the "start" menu), I tried installing Office, the entire reason I still use a PC. I rebooted the PC and voila - Win 8 told me it couldn't start Win 8 and I had to revert to an earlier point in time.
I tried doing that and after another hour, Win 8 told me it couldn't do that either and I had to reinstall Win 8.
I put the laptop back in its box and returned it and just started learning how to use Office on Mac.
This is why Microsoft is just pathetic. I feel pathetic for giving Microsoft a chance. This isn't hyperbole: Windows 8 is really a complete and utter failure.
Right now, it's primarily through referral and search. It is a well networked industry so figuring out how to get users to refer other users is one key. Also, with most paid channels (which we haven't used very aggressively yet), keep in mind that the cost of user acquisition and be offset by a. conversion into an upgraded account and b. the lifetime value of an upgraded user.
I'm a big fan of what you guys have built at Thumbtack. In fact, prior to BuildZoom, I remember looking at Thumbtack and really digging the interface & design. Its a great company with great leadership, heading in the right direction.
I do question the premise of the services market as whole being a "winner-take-all" space. I do believe this becomes more viable in a more narrowly defined segment of the overall local services market.
I think the marketplace examples of a "winner-take-all" (e.g. eBay and Amazon) are a bit questionable (it isn't the first time I've heard this perspective).
When I want to buy something used (for example), I have probably turned to Craigslist just as many times as I've turned to eBay. When it comes to new items, I always look at Amazon but the overall query covers a much broader space, which will include more specialized e-commerce sites.
Measuring lead indicators of good UX is a little tricky.
Ideally, you would look at frequency of repeat usage against competitors but getting their data seems to be unlikely. Net promoter might be another useful metric but I'm not sure there is a silver bullet for measuring good UX.
Tahoe has been a little tricky. You need a contractor who is regulated in CA however a lot of the contractors near Tahoe are licensed in Nevada (although a number are licensed in both states).
One of our advisors has a house up there and we've been working with him to create a better experience in that region. If you want to let us know a bit more about your project, I'll make sure we get a great contractor out.
There are several players in this space. Perhaps the largest are HomeAdvisor (formerly ServiceMagic) and Angie's List.
There are some distinguishing factors: one of the biggest is that we use a heavily data driven approach. One of our goals is to consider every single licensed contractor in the United States. In most areas, the actual number of contractors who are licensed to practice is an order of magnitude (or two) higher than what is considered by most sites. We actually just look at the actual population of contractors to help a homeowner determine the right choice.
This is one of our goals: mitigating the information asymmetry in the remodeling sector (georgewfraser's articulation). If you are interested in comparing notes, I'd be happy to chat.