One of my biggest dreams in this industry has been to attend the Business of Software conference. Business of Software is an annual event aimed at software entrepreneurs and people involved in startup software companies. It is a multi-day event that brings together presentations and workshops from some of the most successful and experienced people in the world of software startups.

Last week I was able to go to Boston and attend Business of Software 2012. In the coming weeks I will write about some of the most useful things I learned there, but today I will talk about each speaker’s presentation to give you a feel for the event. (Recordings or transcripts of the presentations will post to the event’s website in the next month or so.)

Kathy Sierra

Kathy Sierra (probably best known for doing the Head First O’Reilly books) gave a fantastic talk in which she detailed the connection between empowering your users to do great things and building your audience. She brought a ton of knowledge to the discussion. I really liked her emphasis that users don’t use your application for the sake of using it — they use it for the sake of doing something for themselves. When you make it easy for them to look good, they will show off their success and give you some credit.

Jason Cohen

Jason Cohen (of WP Engine and Smart Bear Software) drilled down into the science of statistics to show folks where being “data driven” can drive you off a cliff. He made great points about margin of error and how it is easy to focus on metrics to the detriment of the actual on-the-ground reality. If you do a lot of data collection, A/B testing, instrumentation, etc. to make decisions for your company, I highly recommend watching his talk or reading the transcript when it becomes available.

Joel Spolsky

Frequent readers know that I am a huge fan of Joel Spolsky (Fog Creek Software, Stack Exchange). I had been looking forward to his talk for a very, very long time; unfortunately, I felt that his speech about “the cultural anthropology of Stack Exchange” missed the mark (even accounting for my high expectations). I had hoped he would talk about how they figured out how to make Stack Exchange’s culture work well; instead, it was more like a feature list presentation. There was value in it, but the information was only good to show how to make a Stack Exchange clone, not how to apply the same decision making process to your community.

Dharmesh Shah

Dharmesh Shah (Hubspot)’s talk contained a lot of very useful information about some of the challenges he has encountered in starting and growing a software company, what he tried to overcome them, and what worked and what didn’t.

Peter Bauer

Peter Bauer (Mimecast) did not give an effective talk in my opinion; it was more of a company history, and his presentation style came off as rather boastful. The only takeaways I got were that his company just got a big injection of money and is growing nicely.

Noah Kagan

Noah Kagan (AppSumo,, Facebook) created a bit of a firestorm of controversy with his talk. The content was excellent. He talked about “rogue marketing strategies,” and it was filled with useful information on how to get and retain customers. There were some very honest moments as well, like when he talked about how AppSumo had gone from being really cool to basically spamming people, and he decided to change their marketing techniques even if it meant hurting revenue badly.

Unfortunately, Noah not only used foul language (almost all of the presenters used some), but he made comments that many attendees felt were misogynistic. I can understand why people felt that way. Because of his style of delivery, a lot of people missed his otherwise excellent information. One attendee wrote a lengthy blog about his feelings about Noah’s presentation, and Twitter quickly blew up with feedback on both sides. Mark Littlewood (the event organizer) issued an extremely heartfelt apology the next day, which I greatly respected.

I think that Business of Software is experiencing some growing pains (this year it had around 400 attendees, last year it was about 250), and as the audience includes more people from outside the world of startups, an increasingly professional and inclusive tone must be set. If you are willing to look past the lack of professionalism, watch Noah’s talk when it’s available (I make a cameo appearance as the man in the Magnum P.I. shirt who won a T-shirt).


Peldi (real name: Giacomo Guilizzoni from Balsamiq) did a fantastic job on his presentation, “Coding is the easiest part!” As software folks, it is tempting when we start a business to sit down and start cranking out code. Peldi explained really well that this truly is the easiest part, and like Dharmesh the day before, shared a ton of “lessons learned” from his experiences.

Mikey Trafton

Mikey Trafton (Fire Ant Software, Blue Fish Development Group), like Dharmesh and Peldi, shared real-world lessons. He focused on how culture impacts the business, and how to create a culture that helps the company succeed. This is definitely another must-see talk for folks starting a company.

Adii Pienaar

Adii Pienaar (WooThemes) spoke about starting a company based out of Cape Town, South Africa, an area that is not conducive to launching a technology company. He talked about the challenges of working with a remote team as well as internationally. If you are dealing with a lot of remote workers or are trying to start a company outside of the areas traditionally known for startups, there is some excellent information here.

Dan Lyons

The speech by Dan Lyons (Newsweek, The Secret Diary of Steve Jobs blog) was mixed. The first part was a rather typical “traditional media is dead, long live mobile content delivery!” talk that ignored and overlooked a ton of important things, like the availability and cost of bandwidth compared to broadband. But then he transitioned into a fantastic expose of the tech industry’s relationship with the media. He left no stone unturned as he ripped media outlets like TechCrunch for their far-too-cozy-to-be-objective dealings with the tech industry, the investors who basically pay off “reporters,” and the companies that can cut journalists off at the knees by withholding access to information and devices to sources that are not favorable (ever notice the lack of Apple and Google coverage from me?). The highlight was in the Q&A when someone asked if a tech company really needs to deal with that circus. His answer was no, and I agree. His speech is top-notch if you want insight into how the tech industry deals with the news, PR, etc., and how to get maximum value out of your dealings with the news industry.

Read about more of the presentations, and find out whether I recommend the event.

Gail Goodman

Gail Goodman’s (Constant Contact) presentation was one of the top three I heard. Her talk was deeply focused on the internal relationships within companies and between companies and customers. Best of all, the information was presented in the style of “this was the challenge, this is what we tried, this is why we tried it, and this was the outcome,” which makes the lessons a lot easier to apply to your company. The most illuminating part was when she talked about how you have to find out where your customers live and breathe and go there. Constant Contact had to do some decidedly traditional marketing (radio ads, Chamber of Commerce seminars) to get customers for her high-tech company. This is another talk you should not miss.

Paul Kenny

Paul Kenny (Ocean Learning) went into depth on the nature of sales. Wait, sales? We’re tech people! Yes, we are, but startups need to sell something in order to survive, whether it is selling VCs on a vision, ad space to advertisers, or something else. Paul went deep into how to actually sell. This is a good speech to watch.

Professor Noam Wasserman

Noam Wasserman (Harvard Business School) went deep into numbers to show exactly where startups fail, and his talk completely blew me away. He had data spanning thousands of startup companies. One of the most shocking things to me was that 65% of startups fail due to things that aren’t really business related (e.g., the quality of the product or marketing techniques) but people related (e.g., arguments between founders, wrong employees, poor company culture). I would watch this talk as soon as I could if I were you.

Bob Dorf

Bob Dorf (co-author of The Startup Owner’s Manual) gave a humorous look into his experiences in starting successful and failed companies. He had fantastic insights that dispelled some myths I had about starting companies. For example, he showed how (a site dealing with a ton of physical inventory) was able to use a money-losing proposition in the first few months (driving around town to buy diapers from stores to fulfill orders at a loss) to prove the usefulness of a business model in order to get funding to build a logistics organization and become profitable. I loved his talk, and I can’t wait to read Bob’s book (copies were given away at the event).

Daniel Pink

Daniel Pink (author of Drive) closed out the event with a talk about how sales is as important as ever… and we are all salespeople. Like Noam Wasserman, Dan had a pile of data, some of which was quite surprising. One of the biggest takeaways for me was that ambiverts (people who fall between introverts and extroverts) are the most effective sales people, despite popular thinking that extroverts are. Another unique insight is that it is easier to win a sale by placing yourself in a position of disadvantage, which makes you better able to understand the customer’s reluctance to make a purchase and therefore overcome it. I have Drive on my Kindle, so I declined the free copy, and I already pre-ordered his upcoming book (To Sell is Human) that the presentation was based on. You will want to watch his speech.

Overall thoughts about the event

The conference was very well run. It started on Sunday night (Sept. 30) with a reception. If you arrived in Boston on Sunday evening and left right after Dan Pink spoke, the only meal you would have needed to buy the entire trip was Tuesday night’s dinner. The food at the InterContinental Boston hotel where the conference was held was absolutely fabulous. I was still recovering after a bout with pneumonia in September, and the food went a long way in helping my body rebuild its reserves after that illness. The staff at the hotel were amazing (which was in stark contrast to some of the folks at the Hilton on 89 Broad Street where we stayed, who were among the rudest people I have ever dealt with in a customer service role). Everything about the InterContinental Boston was perfect except for the Wi-Fi, which was a mess to get onto and very slow.

It is a very costly event. Tickets are expensive, the price of hotel rooms in Boston is crippling, and travel is pricey unless you live nearby. If you aren’t going to network, there aren’t as many reasons to go in-person rather than watch the live streaming presentations. I went with a team of people, and we ended up being a bit insular. It was a great team-building time, but I lost out on some of the networking chances. Next year, I will either try to mix a lot more or watch the live streaming. In fact, I’d even be willing to pay to watch the live streaming — the content was that good.

I struggled to get much value from just two presentations (Joel Spolsky and Peter Bauer), which is an excellent ratio for such an event. The workshop time was great; my team was led by Red Gate’s Neil Davidson (one of the people I look up to most in this industry), and we got to do some very creative things and get to know each other. The “lightning talks” (presenters were given only a few minutes, and their slides automatically rotated every 30 seconds) were fun, refreshing, and provided interesting content.

The issues people had with the Noah Kagan speech were inevitable. When you are already pushing the envelope on these things, it is much easier for something to go wrong. In this case, an event where nearly every presenter was using language that would get you fired at a lot of companies and that you couldn’t say on broadcast TV is likely to eventually have a speaker who says something offensive to a significant portion of the audience. It is a shame that an otherwise great event got caught up in a controversy.

Most of the content was of the “I can take this and use it” type. Best of all, Business of Software 2012 was inspiring. You leave the event ready to quit your job and start a company with your loose change and pocket lint, even if you are already running a company. If you run or work for a startup or are thinking about launching one, I cannot recommend the event enough.


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