On the footsteps of Evan Williams (Odeo) and Andy Sack (Judy's Book) talking about decisions, strategy and executions that didn't go so well on their company, I also decided to write my own version of it with regards to Sampa.
There are two reasons that I'm doing this. First, it helps me flush out some of the stuff on my head and think more clearly. Second, and most importantly, it can help some other entrepreneur out there that might look at this and learn about it.
The list is not in priority order, but more or less in occurrence order.
#1: Taking too long to get started
I had this idea 3 years before I left Microsoft and started Sampa, circa 2001. The idea was not very solid, but by 2003 it was mostly what you see today. Between 2003 and end of 2004 I tried to convince Microsoft on doing it. That was a huge waste of time. I should have packed my stuff and started Sampa back then.
#2: Being in Stealth-mode for too long
If you are a Startup that is entering a big market, there is no reason on being stealth. What? Do you think Microsoft or Google will look at your 2-person company and say let's copy what they are doing? Get real. Only about 5 people knew what I was doing for the first 9 months. After I started telling people, a wonderful thing happened. People started connecting me with other people doing similar or complementary work. If I could roll back time, I would have told everybody that I knew about what Sampa was going to be.
#3: Not having a partner in crime.
This has been said already on many books and blog posts. You are much more likely to succeed if you have somebody else working with you. Back when I started Sampa, it never occurred to me that somebody else would even be interested in joining me. This goes back to #2. If I had been more open about it, maybe I could have found somebody that had the same passions and motivations that I did.
#4: Taking too long to decide between Small Business vs. Consumer
Sampa was never meant to serve a medium or large-scale site. So, the obvious choices were Small Business or Consumer. I did what every ambitious (and dumb) people would do: I decided to go for both! This was mostly a R&D mistake at the time because I had no product, brand or marketing, it wouldn't affect those disciplines. But I spent a lot, a lot of time developing features for Small Businesses that are not useless. We actually even removed some of them from the site. Sampa is officially a consumer product.
#5: Not preserving user data during Alpha tests
Alpha was meant to be alpha, so, I didn't want to have to be backward compatible. Every Alpha release meant all user data was gone. Everybody had to sign up and try again. The vast majority of users understood that and were ok with it, except they didn't come back later.
#6: Swing too much vertical
Sampa was a very horizontal offering, meaning, it was a product without a niche. It works for anyone. Marketing 'experts' will tell you this is a bad strategy for Startups because you cannot get past the noise level and you never create a brand. The suggested solution is to go vertical, find a niche where your product can provide a great solution for their problem, build a few features focused on them and market like hell for that group. So, we picked a niche, then we started picking sub-niches, and spent a few months working only on features, branding and marketing strategy for those. That was too vertical. We are a horizontal platform, and this is how the service was designed to be. Being "too" vertical meant going against the grain of the platform. Right now we think we can pick a niche without being vertical.
#7: Hiring 'A' players that didn't fit the culture
You know how every single Entrepreneur book tells you to only hire 'A' players, the best -- well, they are wrong. You should hire the people that will produce the most results for your company, and that is usually a combination of excellent people and synergy with the existing culture. And culture being the broad term that represents everything a company is and has.
Great post. I especially agree with your point about stealth mode. The more feedback you can get as an entrepreneur, the better. Also, your point about preserving data through the alpha is a great one and makes perfect sense. Thanks for taking the time to share.