Should you come to Business of Software if you are a small, bootstrapped business?

I thought this would be a good opportunity to run this guest blog from Stephen Kellett of Software Verify, prompted by a note I received this morning… I haven’t had permission to publish the details of the email so I have removed any personally identifiable information. The essence of the question though is, ‘Should bootstrapped businesses come to BoS?’


I run a small bootstrapped software company.

We have a samll US team of 2 employees (me & wife, and some part time contractors)  and have a remote team that is full time from India.

I am trying to evaluate if BoS would be the right conference for me to attend given our stage of the business.

My cell is below if you need to reach me.


My take, in short – while we try to focus the content of the event on the how, who, why, when and where of growing a successful software business, almost all of the content is incredibly valuable to software entrepreneurs who are starting out on their journey. We have a single customer at BoS – you, the attendee. No sponsors or exhibitors to keep happy. Just the delegates. Of course you can go to ‘cheaper’ events, but we think that people come to BoS because they are able to learn, share their ideas, their fears and ambitions with a  very special group of people. You will find people who are incredibly willing to help a single founder/startup – everyone started out at some point and it is wonderful that so many people are willing to “give something back.”

You can also see all of the feedback from delegates at Business of software 2011 here.

I figured it is a question that a lot of bootstrapped companies will ask so I have tried to answer it with the help of Stephen’s guest blog. Stephen is a single founder and Business of Software regular so perhaps his thoughts will be useful…

“In October I travelled again to Boston, MA for the Business of Software conference. This is the number one conference to go to for folks aiming to create a software business to last the long term. This isn’t a place to come if you want to create a Facebook then flip it and walk away with millions. Nothing sustainable about flipping companies.

Twitter seemed to come into its own at and before the conference. People using phones, iPads, laptops to coordinate who they were eating with and when. #BoS2011 became unmanageable. Mark Littlewood’s advice to use Tweetdeck was well received.


Its a self selecting audience. They’re all very bright, self motivated. A lot of the people attending run their own businesses, from one man companies to some larger organisations like Red Gate who brought a good chunk of their staff with them. 30 people? 50 people? I don’t know. A lot – more than many people have on their entire staff. I spent Saturday evening with 5 Red Gate people and most of Sunday with some more Red Gate folk. It seems that Red Gate is being quite entrepreneurial with its staff – exposing them to conferences like this and training them for the future. It seems like a much more thoughtful vision for their future than most companies take.

Microsoft had some people in attendance too. The only Microsoftee I met was Patrick Foley, who was brave enough to give a Lightning talk. One attendee had travelled all the way from Romania, using three planes to get to Boston. He was probably one of the youngest attendees too. I spent a chunk of Tuesday evening chatting with him in The Whiskey Priest. Not sure I’d have been that keen to travel that far for a conference at age 25. Kudos.

The quality of the speakers was incredible. I thought Clayton Christensen would be the top draw (I’ve read most of his books, found them really interesting) but as it turned out I preferred the speakers on the second day – Rory Sutherland and Josh Linkner in particular. Most speakers manage to weave humour into their talks. I don’t know if this was planned, opportunist or just something you get good at.

Note taking

I took very few notes at Business of Software. I was just too wrapped up in what was being presented. When I look at my notes its in my typical unreadable “I should have been a doctor” handwriting, with a good chunk of the notes not about the talk being given but about ideas for improving the software process at Software Verification. Its as if being there was stimulating me to take action over what we will do in future. Part of me is pleased with this and part of me is frustrated I didn’t take more written notes.

[Actually, Stephen’s notes are pretty good. You can read them all here on his blog – Business of Software 2011 – Mind Food].

The Business of Software goodie bag was unusual – full of stuff I will actually read. Books from some of the speakers. Their talks were interesting, so that bodes well for the books they wrote.

Business of Software Team

The team Mark Littlewood assembled were superb. They were always on hand to help. When I asked them for help with some nuts (I needed protein as the vegetarian food was all carbohydate and had no pulses etc) they to my amazement found some fruit and nuts for me. I expected them to tell me where I could find a shop. Later that evening two of them saw me collapsed on a seat at The Whiskey Priest and came over. They wanted to walk me back to the hotel until I explained I’d be alright in about 20 minutes – when my blood sugar had become normal again after eating (I shouldn’t have had the beer so soon after eating with the noise of the Business of Software band – too much).

As well as the BoS team, the conference centre staff were helpful and courteous. Americans really understand service. So often I’ve had bad experiences in the UK.

Coming home

Krishna Kotecha, Patrick McKenzie, Corey Reid, Patrick Foley, Levi Kovacs, Tyler Rooney

After the conference everyone had a chance to grab some food, possibly be interviewed by the roving cameraman. He got me. I don’t think I made a very good subject. I think you’re either good at this or not. When asked a question that required a thoughtful answer I should have paused and thought. But no. So a bit of a disaster on that front. I’m sure other people had better things to say to the camera than I did.

I milled around for a bit then a group of us headed off to a local restaurant for some pre-flight food. Mark Littlewood said he’d come and join us, but he took so long he met us on the way back to the hotel. Better luck next time Mark.

[Ha! You got me. We ran a few optional post-event workshops that started at 1.00 pm. They were supposed to finish by 2.30 pm. The last one finished at 4.30 pm and I figured I should be around to see people off the premises… :-)]

The photo shows (left to right) Krishna Kotecha, Patrick McKenzie, Corey Reid, Patrick Foley, Levi Kovacs, Tyler Rooney.

TO DO List

My notes are littered with TO DO items scrawled done as a speaker sparked something in me. On the plane home, reflecting on the conference, I found that every few minutes I’d have to write something down. In total I have about 4 pages of TO DOs, 1 per line. That’s about 120 items to do or research. All directly from attending the conference. Not all of the TO DO items were new to me at the conference, but the conference reinforced my pre-existing thoughts and coallesced them into an action point.


If I could summarise Business of Software into a few words, it would be “Incredible mind food, stuff to think about for a long time”.

Would I go again? Yes.

Am I glad its on the East Coast of America? Yes. 5 hours out is one thing. 8 hours out another altogether.

If anyone wants to share their experiences in the comments – or via a guest blog, please get in touch.

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