My favorite conference both as an attendee and as a speaker is the Business of Software Conference. I've spoken there for the past three years and am once again speaking this year. There's a full video and transcript of my 2010 talk.
To give you a sense for how much I like the conference, I will share this embarrassing piece of data: Though the conference has been held in Boston for a couple of years (and again this year), and I live in Boston, I still stay at the conference hotel. I do this for one very simple reason -- I just enjoy hanging out with the BoS folks. They're my peeps. 
Note: I do not make any money promoting the BoS conference. I don't even charge for speaking there (note to self: I probably should charge and just donate the proceeds or something). The only reason I write articles like this one, is I enjoy the conference and think others would too. I'm selfishly trying to draw in as many cool software people to the conference as possible, for my own amusement and enjoyment.
One quick word of warning: The registration fee is not cheap (the ticket price is currently $2,295). The show is just about sold out, but I have a discount code for OnStartups readers that brings the price down to $1,895. Use the code OSBoS11 and register on the Business of Software website.
In terms of price, I think the time you spend attending a conference far exceeds any registration fee. BoS does a great job making the most of your time. You will not hear speakers making sales pitches. No sponsored speaking slots. No booths. No multiple tracks or boring panels. Just great attendees, great speakers, in a great venue and well managed.
The conference is coming up (Oct 24-26) in Boston. If you can make it out, you should.
Here are some of pithy insights learned from prior Business of Software conferences (to whet your appetite)
Pithy Insights From Business Of Software
1) The right time to hire the first person is when you think you are going to die. [tweet]
2) Do what you are naturally good at. Starting up is hard enough as it is. [tweet]
3) Be prepared for serendipity. Viagra was originally a failed heart medication. [tweet]
4) Don't reward people with bonuses. They don't remember them. Give them experiences. [tweet]
5) HubSpot has an unlimited vacation policy. No one has abused it. If someone did it means we hired the wrong person. [tweet]
6) Long term thinking: I've always wanted to build something that will survive beyond me. [tweet]
7) One model doesn't take you through. We had to move from generalists to specialists. [tweet]
8) If no one is copying it try harder next time. [tweet]
9) Venture capital is not a necessary evil. It's neither necessary nor evil. [tweet]
10) Tech support is sales. [tweet]
11) The power of being ready to walk away is amazing during M&A. [tweet]
12) Forget about competitors! You want to create something so good people will want to copy it. [tweet]
13) Developers like email, sales people prefer the phone. They're just a different kind of human. [tweet]
14) Negotiation 101: "Shut up" [tweet]
15) Build your software with your customers. [tweet]
16) You set the rules in your start up. Don't live inside someone else's box. [tweet]
17) If selling your company having multiple offers makes it easier not to have to compromise what's important to you. [tweet]
18) Ask simple direct open questions and LISTEN! [tweet]
19) At Squidoo every job that can get written down is done by a freelancer. [tweet]
20) Be so good they can't ignore you. [tweet]
21) B2B tribes are much more valuable than sexy consumer tribes who won't pay you anything. [tweet]
22) Companies spend about 10% of the time hiring a person compared to getting rid of a bad one. [tweet]
23) Different & Crazy can look the same at first. Real difference requires some risk. [tweet]
24) Don't change the model! Change your management practices! [tweet]
25) Don't follow a map. Make a map. [tweet]
26) Founders bring with them personalities and philosophies that set the tone for the company culture. [tweet]
27) Great ideas are fragile at birth because they are indistinguishable from crazy stupid ideas. [tweet]
28) If you can write it down I can have it built cheaper. [tweet]
29) If you invest in the experience (not just the product) everybody wins. [tweet]
30) Just because the tide is out doesn't mean that there's less water in the ocean. [tweet]
31) Passion is an extreme version of caring and believing. [tweet]
32) Love your inner salesperson. [tweet]
33) People like to be sold to in their own language not yours. [tweet]
34) Pricing is a lot about psychology. $25 and $35 feels the same to people. [tweet]
35) Problems should be the currency in your company. [tweet]
36) Prototyping helps figure out what to leave out. [tweet]
37) The factory is about interchangeable parts -- and interchangeable people. Factories don't work in software. [tweet]
38) Customers will always tell you how to improve but not how to be different. [tweet]
39) Southwest Airlines value people who 'get it' vs people who 'know it'. [tweet]
40) Steve Jobs doesn't go home at night and boot up Windows. [tweet]
41) Traction requires friction. The mini cooper chafes. [tweet]
42) When selling your company walk away at least two times or you have probably been screwed. [tweet]
43) Work definitely feels like work unless you're passionate. [tweet]
Hope to see many of you at the conference. If you're there, please say hello.
And, if you've been to Business of Software before, how did you like it?