Lessons learned from my failed startup after 2 years, 300 users and 0 revenue

Well, it's that and a lot more.

Some of the really established guys --20+ year career in the industry-- can come with this "I can walk on water" attitude as they drive their leased Jaguar into their parking slot. Then they cave when they realize this is a new market segment and a new product segment in the industry. They are used to people coming to them to buy the old stuff. Now they actually have to work, learn the new product, learn the new lingo and also identify customers who might be receptive to the message.

Then you have the guy who worked for a rather large company and is used to the fish jumping into the boat. No fishing rod or fish finder required. You don't even have to know how to bait a hook. These guys, amazingly enough, actually think they are selling. When faced with a situation where the phone only rings if they make it ring they don't do very well.

There's the guy who faked it in a good market, got lucky and built a reputation on circumstance rather than skill. When things change (i.e., the economy tanks) the reality of their capabilities comes to the surface.

Then there's the inability to adjust to a change of audience. You don't sell to an engineer the same way you might sell to a manager or the president of a company.

One of the most frustrating things for me has always been the sales person who attempts to take credit for a sale that came in because I spent tens of thousands of dollars in marketing. They think you are stupid. Or at least they act that way. Some of the most memorable moments in my experience have been after major trade-shows. Imagine having a sales person come to you like he just climbed Everest to close a sale after you just spent over $100K to exhibit at a trade-show for a week. You look further and you see the sale was due to a years-long relationship with the customer as well as a meeting at the trade-show where the sales guy didn't even interface with the customer. What did happen is that he got and printed the purchase order because he was in charge with monitoring sales@company.com. In retrospect it is really funny and it also reveals interesting character flaws.

And, of course, there's the mercenary sales person who will hand out discounts like they are candy in order to book sales and look like a genius to anyone except for the person who actually looks at the numbers.

There's more, of course,

The advantage of the motivated newbie is that they can learn the product, the market and the approach. It takes six months to a year of real work to get someone up to speed, but it can really pay off. Most business owners I reached out for advice would roll their eyes when I asked for the secret to hiring good sales people. Everyone had horror stories galore.

One of the toughest skills to learn for in-person sales is to know when to close your mouth and let the process happen. When I started my business I would talk and talk and talk. I probably lost more sales to that than any other blunder. A year later, I'd show up to a call, "read" the room, meet some of the people I didn't know, setup the demo and mostly let the customers sell themselves on the product. Selling by saying less, not more, is a skill that takes time to develop. Most really good sales people are very relaxed and confident during a sales call.

One of my friends put it like this: It's like the hotel business. You can print beautiful brochures; exquisitely redecorate the rooms; have amazing food and all manner of services. You can't force people to take a vacation.

I think he is saying that a CEO can have salesmanship skills like the ones listed in order to "sell" people on the idea of working for the company, but it doesn't mean that he is also able to pick up the phone and do cold calls to sell widgets.

A mistake I made early on was trying to provide a product as cheap as possible. Constantly worried that no one would pay what we asked for.

Basically being afraid to ask for the value it was really worth.

I think there was a comma/period swap, but if I'm reading correctly it looked like the product was positioned at $30 / mo?

Assuming that's correct - it's really not a meaningful amount to any company that has enough employees and management to actually be a user of the product.

I think a $30 / mo with a free 30 day trial period (once product launches and they can actually try it ;) ) that requires a credit card for the trail could have worked.

Would still need a product to actually try, but that's not much different than saying get a free trial and just taking in email addresses.

If anyone remembers the Minimalytics / Small HQ folks - I thought they did a good job with their signups. The only thing for me was I disappointed by how minimal their product was in beta. It was so basic I didn't have any use for it, and running our own startup, didn't have time to wait. We ended up building it internally.

I probably would have converted to a paying user if it was more developed at beta. Not their fault though, they did a good job I thought(if you're reading Small HQ).

I think you missed the reference. They were referring to a company from the TV show Parks & Recreation. See here https://www.youtube.com/watch?v=jX0ZF8f8G0A

Would you look for anything in particular when choosing a newbie? Maybe expeirence in used cars or insurance?