Bootstrapped Interview: Mark Littlewood, Business of Software

Our first Bootstrapped interview features Mark Littlewood. Mark runs the Business of Software (BoS) conference, held each year in both Europe and the USA.

Hi Mark! What’s the Business of Software conference? Who it is for?

The Business of Software Conference is a conference and community for people who want to build software/SaaS products customers love and software/SaaS companies people love working for.

We curate a programme of talks that help people do three things:

  1. Product. Think about how to build things people want, will use and pay for. Not all great software products are great businesses. Not all profitable businesses have great software or do things that impact the world positively. How can you build things people will pay for and help you build a sustainable business?
  2. People. Think about how to create and grow a company that attracts the right type of talented people. At the heart of every great business, people make it happen. You need to find, attract and develop great people who need leadership, direction, purpose, vision and bring everything together so the sum of the parts is greater than the individuals in your team.
  3. Customers. How can you ensure that your business will be successful in the long term by ensuring that the software solution you build will continue to grow and attract more profitable customers? How do you find more customers (marketing) and get them to part with their money (sales)? Neither sales nor marketing are dirty words, though a lot of tech entrepreneurs fall into the trap of thinking they are, because of their experiences with the industry norms. There are much better ways.

We steer clear of ‘magic’ solutions – those motivational speakers on the circuit offering the guaranteed SaaS marketing playbook type solutions. We know every business is different. Every business exists in a unique set of circumstances and context is everything. We never offer a ‘one-size fits all’ answer. Quite the reverse.

I think that most questions are relatively easy to answer once you know what the right question is for you. If BoS can help an entrepreneur understand what the right question is, we have succeeded!

The Business of Software conference has been running since 2007. You weren’t directly running it in the first couple of years. How did you come to run the Business of Software conference?

I was friends with Neil Davidson from college and have run events most of my professional life. Neil co-founded RedGate Software and got to the point when the company was 30 or so people. He thought he was out of his depth (he wasn’t), and needed to learn how to build a business. He looked at various events about building software companies and felt they were either about code, being a startup or how to raise venture funding/IPO.

There wasn’t anything about the craft of building a company. He set up BoS to scratch that itch. He also didn’t want to run an event business, as there is far too much hassle and stress.

Neil approached me as I ran events and shared a similar outlook on life and what was important. I got involved in 2010. He is still involved as a shareholder and we run BoS true to the original spirit of the idea, having resisted many approaches to grow, expand, scale, and take over the world.

We’re always puzzled when events market themselves as the fastest growing, biggest event, etc. McDonald’s is a big restaurant, but that doesn’t make it the place you dream of eating at.

Running two editions of the conference on two continents is surely stressful. What motivates you to keep running the Business of Software conference?

It is much easier to run the second event, Business of Software Europe, as it is on my home continent!

I do it because much of the time, despite the daily grind and the constant worry of, ‘Have we got the right speakers, have we got the right attendees, how can we manage the expectations of sponsors who so often expect to sponsor and speak?’, we are making a difference.

Last October, as I walked around a pretty big SaaS conference, someone came over to me and said,

“Are you Mark Littlewood?”

Duh, that is what my badge said.

“You saved my life.”


“I’d been running my company for 6 years, all in. Savings used up. Relationship at breaking point. I was despondent that what we were doing wasn’t working. We weren’t getting there. I was exhausted. Whenever I looked around for help or advice, all I saw was tales about crushing it. Instant success. Brilliant people with growth mindsets killing it. My life was wrapped up in my business, and I’d been telling my wife it was all going to be worth it. It wasn’t. I’d failed and the only way out for me was my life insurance. No use to me but… Then I watched Gail Goodman’s talk, The Long, Slow, SaaS Ramp of Death. For the first time in a very long time, I got some perspective. This shit is hard. Don’t be hard on yourself”.

Happy ending. Five years later that person has a relationship with his wife and kids, some sort of work-life balance and a company with almost 200 people and no outside funding. He is alive and thriving. He recorded a video on my phone and asked that I share it. I don’t think I ever will as while it might be good marketing, it was a very special moment. That’s enough.

There are plenty more times when we’ve been told we made a difference, we have helped, and we have been instrumental in making a pivotal difference in the growth of a business. That sort of thing means I could never walk away.

The videos of all talks from past conferences are a great resource for Bootstrappers. Some, such as Gail Goodman’s talk you mentioned have become widely-shared classics. What are a couple of your all-time favourite talks? Why are they favourites of yours?

All the talks are my favourite talks! Never a dud. Well, there are two I have curated that I am embarrassed to have had talk. They won’t be coming back. They disrespected me but most important, the audience.

A favourite is, Greg Baugues, now at Twilio, on Developers, Depression and Tech. We talked about feelings before it was fashionable.

Greg applied to do a BoS Business Development talk. He didn’t get to talk but I really liked him and we stayed in touch. A couple of years later he applied to do a Lighting Talk about depression. We decided to make it a full talk.

It is the only talk in BoS history that had a standing ovation. It was incredibly powerful and hysterically funny. It got people talking and saved lives - literally. I still get emails.

Greg had a massive impact on me personally, I discovered I had ADHD as a result and that probably saved my marriage but that’s another story.

Us Bootstrappers have limited funds and time. What’s the value to Bootstrappers of attending conferences? How should we choose which conferences to go to?

Conferences do many things and you have to pick the ones that are right for you and what you want to achieve. Some help you promote your business, meet new potential customers, raise your profile, and help you hang out with people that pursue the same groove as you.

We serve a niche. Our attendees want to be the best they can at what they do, spend time with like minded folk, and come to listen. They want to spend time with other smart people and spend time working on, not in, their business.

Whatever you do, you should be clear about why you want to come and what you want to achieve.

Now a chance to pitch Business of Software directly. Convince us that Business of Software is a good choice for Bootstrappers!

We will give you ideas and the connections to help you build a profitable, sustainable, business, or your money back.

@MarkLittlewood, Business of Software

Want to know more about BoS? The next events are

Can’t make it to the events? You can watch videos from past events.

For Bootstrappers wanting to go BoS Europe, Mark is kindly offering us tickets with a 20% discount.


Thank you so much Steve. An honor.

As the conferences have been going so long and we have built up quite an archive of material, navigating all the talks can be quite daunting. If you subscribe to the mailing list, the first thing you will be asked is if you have any particular issues you would like to think about. We will send you a couple of links to talks that we think are relevant. ML Inside. Not so much machine learning as Mark Littlewood.