14 years building BoS

After over a decade of hosting BoS Conferences, and inviting hundreds of smart and amazing people to come and learn and share their experiences with one another at conferences across the globe, it was about time someone sat BoS’s Mark Littlewood down to find out what he has learnt, enjoyed, and tore his hair out over in his journey running Business of Software. There was only one team member brave enough to take him on.

Join Kirk and Mark on the 100th episode ever of the BoS Podcast.

Kirk Baillie  

So I know you’re busy prepping for BoS conf online. So let’s dive into finding more about you and the journey you’ve been on with BoS over the years. You’ve ran BoS for over a decade, and this is Business of Software’s 100th podcast episode. So just in case there’s anyone out there who doesn’t know who you are, and what, what you do, do you want to give us a bit of backstory about you and the Business of Software?

Mark Littlewood  

Yeah, I’m Mark Littlewood. I’ve been running businesses software for over a decade, and have been involved in tech and venture capital and investment and all sorts of things. For the last 20 years or something, I knew a guy called Neil Davidson at university, I taught him to row which was about the one skill that he never mastered. He’s managed to do everything else in his life. He co founded a company called Red gate software, with Simon Galbraith grew that didn’t take any funding, just wanted to build a great business. And he got to a point where the company was 40 or so people, was profitable, was growing. And he looked around the room and was like, I don’t know how to run a business. He wasn’t doing a bad job at all,

Kirk Baillie  

I’m sure a lot of people have been there as well. And they know that feeling.

Mark Littlewood  

I think everybody goes through life like that, or they’re lying, or self deluded! So he kind of looked around and said, Well, I don’t really know what to do here. I like to learn. So I go to some conferences and teach myself. And he looked around, and there were lots of conferences for coders. And there were lots of conferences for startups and lots of conferences for people that were raising funds and IPO going and all sorts of crazy old things. But nothing really about actually the mechanics of growing a business and learning to be a CEO that can lead a successful company.

So being a pretty amazing entrepreneur, he decided to set that event up. And he put a shortlist together of all the people that he wanted to learn from in an ideal world and got in touch with them and said, Hey, I’m running a conference, will you come speak and Geoffrey Moore and Jason Fried and Joel Spolsky, from Fog Creek, and all sorts of people said ‘absolutely, love to’. And that’s where business software started. And it was designed in a very different way to most events at that point, it was very much a content driven thing wasn’t there to become a massive event, it was built to scratch an itch, build a network for Neal, help him learn from other people. And it took off. And he decided pretty quickly that he wanted someone that ran events to come in and do it. He was still co CEO of a company he was running. And that’s when he got in touch with me. And said will I come and help him. And I did and eventually, I’ve taken it on. And the rest. It’s not quite history, because history is important stuff you learn in school.

Kirk Baillie  

So you’ve come in and you’ve been running annual conferences since 2007, and then bi annual conferences since 2014, when you launched the EU as well as the US conference. 

Mark Littlewood  

Correct. 

Kirk Baillie  

So this this will be an interesting question. I know that I know some of your BoS conferences can seem like children with the amount of time and care and you’ve put into nurturing them. So if you’re asked to be you know, to pick a favourite, I can understand that may be quite hard to do. But are there any particular conferences or even individual talks which stand out to you as being your favourite or most memorable?

Mark Littlewood  

So can I start with the most memorable in a bad way? 

Kirk Baillie  

Please do. 

Mark Littlewood  

which was way back in 2011, I think and we were running a conference in Boston. We’d taken a new venue on because it was growing and getting bigger and we couldn’t accommodate everybody in the old venue. It was pretty interesting. We had about 700 people signed up. About three weeks before I realised I my visa had run out and I had to get a visa. I ended up spending 10 days in a really horrible Hotel in Brussels. While the American embassy in Brussels processed my visa application. I got my visa two days before, we had to fly. So the run in wasn’t super chill was going to get the flight, got on the flight was actually on the on the runway about to take off, had a call and my dad had gone into hospital and was having a heart bypass. And they were like, I don’t worry, it’s all fine. And flew off to Boston, did the conference stood on the stage and the first morning and saw everybody was like, Oh, it’s too big.

I couldn’t see the corners of the room. And so there were some amazing talks. And there was some amazing people. But that really wasn’t my that was really the experience that stands out as being the least pleasant. And as a result of that kind of coming back and my dad’s fine, he’s all good. And now 82 and fitter than I am by quite a long way and came back. And we decided that actually we were going to keep the conference small that we didn’t want to grow. And we’ve never wanted to be the biggest conference in the world, I guess there was that sort of slight reacting to market demand. But ever since then we’ve had a conscious limit on the number of attendees, and focused on quality people coming because there is a real value in having a high density of quality people in a room. And there are, it becomes a less valuable thing if you get too big. So it was certainly quite a pivotal, pivotal point in the growth and development of the conference.

All of the conferences, I mean, I love in different ways, as you say they are my children, and even the ones that had difficult births. Possibly my favourite, possibly 2013 was really lovely in many, many respects. It was smaller than the one from two years previously, it was back at the seaport and the amphitheatre absolutely in a fantastic atmosphere. And we had a number of talks that were I mean, quite groundbreaking at the time, one that I come back to and a lot of people come back to was by a guy called Greg Baugues, who talked about developers and entrepreneurship and depression. Super super talk, one of the funniest things I’ve ever read, seen about depression. I mean, laugh out loud, entertaining. And he also had a heat he stood up at the beginning and he was I’m Greg Baugues and I have bipolar and ADHD and I’m doing my things as you’re always doing at that conference and he was talking about bipolar and it was quite an absorbing and involving and, then he talked about ADHD. And you know, me being me, I thought he must have missed a slide because he was doing the kind of Okay, so this is the ADHD brain or this is the normal brain and this is the ADHD brain. I thought I’d missed the normal brain slide. Because he put this thing up. So okay, that’s normal. So what’s the ADHD brain? Right? I just thought I’d been distracted. That kind of got me thinking.

Greg Baugues, Manager & Developer Community at Twilio.

So wonderful talk and that are rightly been talked about by lots of people. And it made a difference to people’s lives. And I’ve had messages from people who’ve read it at very difficult or watched it at very difficult times in their life, and it saved lives without over stating it. But yeah, that the ADHD thing was an absolute. Hmm, that’s interesting. And my wife was with me in Boston, used to bring her over to help run the event before she actually ran the event. And I remember getting into bed that night, at the end of the day, a great date or just lots of lovely things going on. And it just as I kind of got into bed, I thought oh ADHD thing. That’s interesting. I think I might have that. Like Haha, and she looked at me and she was like Yeah. And conferences are really interesting. Sleeping is very odd and evenings. There, you’re jet lagged. But there’s lots of adrenaline going on. And you’re never quite, fully switched off. And I remember waking up at about 330 in the morning, thinking, ADHD, ADHD, right must not wake up wife. So I got my laptop and went into the, into the bathroom in the hotel room, I’ll open up my laptop and Google it. So I opened up my laptop. And the next thing I kind of looked at the time, and it was seven o’clock, and I was still on Twitter. And I hadn’t actually managed to Google anything. I’m pretty sure that’s kind of part of the official diagnosis. So anyway, as a result, I’m now still married, which is great. And yeah, you know, those are definitely memorable. moments. People often ask what, what are the best talks? And actually, we get asked that a lot. We’ve just wrote written a little blog with some of the best talks. But I like to think that I’m pretty good at finding things that will keep people engaged, suddenly realise that ADHD is my superpower. If I’m convinced someone will keep me watching something for an hour, everybody else is golden. Trust me. So, yeah, they’re always they’re always kind of talks that really kind of bring you up and think, but it’s, I think it’s the it’s the little conversations and the little interactions that you have with people. It’s the little things where people talk about how we’ve made a difference to them. And what the communities are about that really are the things that give you energy.

Kirk Baillie  

There’s quite a few talks that, although, I wasn’t there, you know, because I didn’t join BoS till 2019. But there’s a lot of talks, I’ve watched that I’ve, I’ve kind of watched and thought, I’m really thankful that they’ve actually done this talk, because it’s either really helpful for me to learn something new, or to see someone doing something that I want to do, or, you know, there’s a lot to be thankful for. And a lot of the talks, which is, which is quite different from a lot of conferences.

Mark Littlewood  

Yeah, we are not really big on the celebrity SEO thing, or they, you know, the other one that talks about the seven sexy secrets of SaaS success. Number eight will leave your jaw on the floor. There is no playbook for any of this stuff. I think everybody’s business exists. And everybody’s existence is very context specific and context dependent. So it’s very hard to say, right, do this and you will be successful. I think what we really try to do is get people to think about the questions they should be asking themselves, the answers are usually much easier to work out once you’ve done that. And that starts from what is good. And I think there is this orthodox narrative very driven by the venture capital community for very sensible economic reasons that part of the process of growing a business is raising money and growing and expanding as quickly as you possibly can. I don’t think that is a very helpful narrative for a lot of lot of companies, a lot of entrepreneurs, and I’m seeing more and more people who are thinking in a different way and challenging that and thinking about the purpose and the why of the business. Thinking about is the purpose of their business to support their users. Well, that’s usually are you doing something good for the world? And are you providing a service that is helping people do something that’s meaningful, but do you exist to grow? Or do you exist to help your stakeholders, your employees, your customers do better things? I’m seeing more or less as we go as well. I remember Natalie Nagele’s talk about her realisation that her company had been growing and it’s really successful super well known super respected, super love business. But she realised that she was feeding the growth monster. And has taken a step away from that and thought about doing things in a very different, different way. And, you know, I think the other person, obviously that embodies this and is almost the spirit of BoS in many respects is Peldi from Balsamiq; just a great, great business, great community does things exactly the way that they want to, and what they want to do is what they think is right. And that kind of comes through in everything that they’ve done. And he’s done a couple of really interesting talks about that. I know that talk about the potential acquisition by Atlassian, which would have been a life changing event for Peldi, as an entrepreneur and significantly life changing event is a real insight into a different way of thinking. Another one of my favourites, but I’ve got about 200 favourite!

Kirk Baillie  

Definitely, one of the things has been covered a couple of times that BoS is imposter syndrome, and we touched on it earlier as well. And it’s a very real issue, which affects a lot of people across the world. I remember my first few weeks at BoS and I mean, deer in the headlights doesn’t even come close to describing, the overwhelming fear of being found out of I don’t know what I’m doing. So, did you ever sit there any of the conferences that you’ve been planning or doing and think, what am I doing here? I can’t do this!

Mark Littlewood  

So I don’t really suffer from imposter syndrome. Because imposter syndrome is one of those things that really successful, clever people suffer from and I’m neither of those. So

Kirk Baillie  

I’m sure there’s a lot of attendees who would disagree.

Mark Littlewood  

I always always think that. I think people think it’s almost a natural state of being there are very few people that don’t have imposter syndrome. There are a few people that should have it. But that’s another another story. I think. I kind of reconciled myself to the notion of being around very interesting, clever, thoughtful people that he on many ways you can’t measure up to but at the same time, you kind of know that they all have their little, their little quirks and foibles. And what was fascinating going back to the 2013 conference, when Greg spoke is that almost everybody that spoke after him and having had that deeply, engaging, deeply moving conversation, then put their hand up and said, Actually, I’ve never said this before, but I suffer from depression. Or I have this or that. Or, remember, Scott Farquhar from Atlassian was like, Okay, this is the moment to tell people.

So I think being around people that are not afraid to talk about their weaknesses in the darker side of being in business, we’re all working through life together, trying to trying to kind of navigate our way. So yeah, I’m constantly feeling like, I’m way out of my depth. I don’t know what’s going on. But also there’s something quite exciting about the thought of being exposed.

Kirk Baillie  

The thrill of it!

Mark Littlewood  

Yeah the thrill of being caught, and there’s probably something something there; probably kind of keys into that kind of ADHD brain and in a funny sort of way, but yeah, I think we all experience it. It’s really interesting when you hear people like Jason Cohen, who was a five time successful, profitable company, building entrepreneur with four exits and one very successful business that he’s involved in now talking about it. It’s fascinating. When you hear about that from all sorts of different levels, actually, there was a lovely talk last year from Tiffany Da Silva

Kirk Baillie  

Amazing Talk.

Mark Littlewood  

Yeah. Which really, I think just sort of those sorts of things give people, they empower people, and they give people time to think and take a step back. And I think we can all relate to those sorts of things. They’re not, they’re not unusual, and you just have to get on with it.

Kirk Baillie  

Okay, on the flip side of that, have you had any moments where you think, yeah, I got this, I know I’m doing this is good?

Mark Littlewood  

So there’s a really great, hilariously funny American comedian called Steven Wright. And I saw him live about 30 years ago or something, he’s incredibly dry. And he has this line about, you know, when you lean back on your chair, when you’re leaning back on your chair, and then all of a sudden you over balance. 

Kirk Baillie  

Yeah, 

Mark Littlewood  

that’s my entire life.

Kirk Baillie  

[laughter] I see.

Mark Littlewood  

So that is my entire life. And it’s such such a kind of evocative line, but I typically will come away from an event. My job, my wife will always, you know, just be nice to yourself, be nice to yourself, but it’s always the what could we have done better? What would we do differently? That floods in but I’m making a more conscious effort to look back and go celebrate. I mean, literally, when the when the event finishes in, in a venue, and people are leaving the room, I’m thinking about next year’s, the themes and the speakers and things that we can, we can do, but I think it is really important. And I’m, I’m consciously thinking about how I do it, I think, let’s look at 2020. And that was something that you were part of Kirk and a massive part of it. This time last year, because this is recorded in the second/third week of March, we were a week away from our first online conference, having announced it was fully online – oh look at your face your poor thing.

Kirk Baillie  

I remember that day. I was you know, up to my eyes and things and all the brochures and pamphlets and all the print stuff we were planning on and

Mark Littlewood  

What a waste the time that was!

Kirk Baillie  

we just got the proofs of the giveaways of the T shirts, and they just arrived. So we were having all this kinda stuff. I was looking around all this stuff going oh no. And I had Paddy on the other side of the camera going, Oh, no – for a whole different reason. But actually, interestingly, on the day that we were recording this, this is exactly one year since we started working from home, it was a Tuesday the 17th of March 2020 that we left the BoS office and set up in our homes for an undisclosed amount of time, which has now become just a part of everyday life.

Mark Littlewood  

Yeah, I mean, I’m just one of the things we’ll be talking about BoS Spring is is the future of the workplace and the future of the office and what that actually looks like the conversations I’m having with entrepreneurs now. No one is really expecting office life to return to what it is. A lot of people have said, we expect to maybe double the number of employees we have, but not change the size of our offices because work patents are changing. But yeah, I mean, I think the last year has been quite, I mean, you know, a was a kind of Cambrian explosion or a … what’s the one where they all die? We had three options, kind of coming out of our mouth. Last online event one was curl up and die, which was a pretty attractive option.

Our entire business was hiring expensive room, get people to pay to come into it, shake the room up, send people away. So we could die. And we could put our hands over areas and go Lalalalala, hold our breath and hope that something will change in a month or something, and it will be okay. And that’s not a very same way of doing things. Or we do what we did, which is say, okay, we’ve always talked about online, let’s think about how it becomes our main thing for let’s say, two years or five years. So we’re just totally focused on it. And what can we do that is valuable, is useful, is a sustainable business and coming out of that, when we switch physical events back on – Happy Days – we’ve got a better business, it’s stronger. And we’ve got two different sets of things that we’re doing. And it was pretty brutal. And I think there were three months when we didn’t sell a single ticket for the conference and something. But I think we’ve we came out with the master classes, and the format for the Masterclasses seems to be far better than a Masterclass. So a real world master class is hire a room in a Holiday Inn with nice fluorescent lights, get everybody to travel, come and drink rubbish coffee, listen to a lecture in a darkened room, and then do exercises. And at some point in the day your brain is full. So any more information that comes in, there’s something going out.

But you have to do it at a day, because everyone’s travelled and time is precious online means that we have a different format. And I think the idea of giving people that lecture, and some reading, and a little bit of work to do in their own time beforehand means that people do that bit at their own pace. And then we run to two hour sessions, separated by, say a week. And those are focused on discussion and problem solving. And it’s a much much more effective way of learning for people. So, there are there are lots of things I think that kind of come out of this that are exciting. And we’ll be doing more of in the future, not because we can’t do physical events, because we can, but I think you know, we serve a very different market in a very different solvent, a different set of challenges for people, which is exciting.

Bounce it back at you, your experiences.

Kirk Baillie  

I suppose I’ve come in a lucky point in BoS’s history, where you just came back from boss USA, so you just travelled back from Boston in 2019, which was your last in person conference. So I had all the fun and joys of planning an in person event, and then not having to actually go through with it. 

So I have a very, very different, my viewpoint is very different from what everyone else in BoS had to see what was going on at the same time. So in that way, I really enjoyed the online format, I think it works really well. It’s much easier for people to kind of engage with, because even the introvertish people, if they really, you know, if they are feeling a bit extra shy or whatever, they can turn off their camera, but still be part of the class and still be there and be present without having to be on show. And for some people even like, you know, going to the Holiday Inn, and even if a dark room, you know, they’re in clothes, they think people should see them, so they’re not comfortable, and they’re in an environment that they’re not comfortable with because they don’t know it or they’ve had to travel however far. And it can be it can be quite alienating to go into a room full of people you don’t know, when you’re not comfortable. 

So being able to do, and be able to learn and get access to some amazing people and speak to the other attendees who are also, you know, really smart, really thought provoking people and do that from the comfort of your own home and your own security blanket.

Mark Littlewood  

Yeah, it’s interesting. I agree. You do you know by the way that we’ve never actually run a physical event, all we did, before you joined was spend time putting Photoshop pictures together.

Kirk Baillie  

I’ve seen your graphic skills, I don’t believe that.

Mark Littlewood  

[laughter] How dare you!!
I think it’s one of the things that I hadn’t expected about the online stuff, we’ve always been very consciously thoughtful about how we can make things introvert friendly. And I think one of the nicest pieces of feedback that I had from an attendee one year was, these are the three days in the year where I am an extrovert that’s kind of coming from a place of people feeling that they can have those conversations, and they feel comfortable doing it. One of the things we’re doing the physical events is we have quiet tables for lunch. And what’s fascinating about those is they are almost invariably the noisiest tables. But having a big sign saying, quiet table, you don’t have to talk to anybody, you can just sit and have your lunch attracts a certain group of people who always have really interesting things to say, but they’re in a space where everyone else is in that kind of mindset. And it just goes to show how, how much they have got to say and what intelligent and positive contributions that people have in those in those situations, if you give them the right, specs, and I’m not a psychologist, I’m not some kind of that open mind bending thing. But a lot of what we do and think about putting together both physically and online is around, well, that’s tricking people into behaving in a slightly different way, and hopefully a more thoughtful way and more open, open way. But that, again, that’s one of those really lovely things about BoS, I think people come or people go to a lot of events and conferences and big things and multi stage events with exhibition halls, and everyone’s kind of on broadcast mode. And look at me, look at me, I’m great. We’re doing this, we’re launching that, we’ve raised this, we’re doubling our revenue, employee count, whatever, every month. And I think BoS people in those environments might do that as well. I don’t think that’s their natural comfort zone. I think when people come to boss, they come on listen, not broadcast mode, and that there’s some some things we do to encourage that. But it’s also a kind of a natural, state of mind of the people that come I think. It’s great.

Kirk Baillie  

Sticking with the online format for a moment, if you could go back to the start of 2020. So before you had to pivot and turn everything online, is there anything you would have done differently? Or would you have just done the same as what you what you did do?

Mark Littlewood  

So that’s an interesting question. I think there’s different… knowing what I know now. Absolutely.

You know, I think I certainly went through a quite difficult period, mentally, emotionally, I sort of was like, break in on one level, I’ve got this thing. And this is the opportunity to do this stuff. But oh, my goodness, it was exhausting. And I mean, it really was there we’d come through 2019 was pretty good year 2020 was looking great. It was all kind of coming together, remember, was that kind of drip drip drip. I think I would have been aware. And so if we were starting that year, again, knowing what we know, now, I think, you know, number one thing we know it’s going to be okay. And we can be much more much more sure of that, I think thinking about, okay, what does this mean, not just for the event, but actually what does this mean for the company and the people in it? I think, you know, you are in a difficult environment working in a small space, you’ve got a massive house now,

Kirk Baillie  

Let’s not get carried away. It’s not massive, it’s just got got a couple of extra rooms where we can work now, rather than being in on top of each other on the dining table and not being able to have a sit down dinner for a year.

Mark Littlewood  

So you know, but it’s, it’s it’s hard. And I was at home working on the kitchen table. We had two children that were being homeschooled. So there’s just all of those, all of those kinds of things that I think, you know, knowing that you’re going to get through that and there are solutions to that and probably addressing them much quicker would have been helpful to know. I was very, very keen that we didn’t cut people. I think, you know, we’ve got a really Small super team and attempting no on one level. I know a lot of organisations have have put people on furlough, we could have. And we would have done less. And we would have not come out in the same way as that as a result, I’m really we’re blessed, we haven’t over expanded, we haven’t been on it. When a huge hiring spree or hiring tear to do things, we haven’t been reliant on ever increasing 50% 100% year on year growth, which some event businesses have been on that incredible tear, and they collapse. And you know, that’s a difficult, a difficult thing, but allow them being more more focused. And I think being more conscious that remote is probably out it’s going to be forever. And I think it’s probably quite quite reticent to talk about that. I mean, partly because the thought of it kind of filled me personally with dread. But what I don’t think it’s what I think it’s like kind of addressing that within the business, I think would have been, I think I do do differently. But overall, I think we came a long way last year, and have come out stronger as a result. And now I’m really kind of quite excited about this year. Really, how about you?

Kirk Baillie  

What would what would I have done differently last year? I don’t really know, like I said, everything that I’ve done at BoS has been other than the first kind of month or two has been geared towards online learning. And, you know, Paddy, who was up in Manchester, so even my line manager was remote. So having that remote aspect has been ingrained into my BoS adventure from day one. And it’s very strange that, like, I’ve only been in the same room as Paddy for what 10 days out of my entire my entire year and a half of being here. But it’s someone who I worked with very closely, every single day.

I think knowing that we were going remote at the start of 2020. And knowing that that would have been the forever plan would probably change my mindset a bit quicker. Because it is something that, you know, we ended up, we didn’t have to move, we were already thinking about moving house Anyway, when it changed, it changed our parameters for what we were looking for. Because it was just a matter of it would be nice to have a spare room if we need a spare room and an office. So yeah, it changed our life quite dramatically. And we needed to have a space that wasn’t just big enough for me to work but also for my partner to work at the same time. It’s not just that it needed a small room, or you know, a kitchen table which we could set up in the corner, we needed a full office space for us both to be able to work from home. So yeah, I think getting into that remote mindset would have been the thing that I would have geared towards quite quickly. 

Mark Littlewood  

So easy in retrospect,

Kirk Baillie  

Of course everything is I’d’ve bought stock in Zoom, like from word go.
I wouldn’t need to be working here anymore. 

Mark Littlewood  

Yeah, yeah, but you would Kirk, its for love the love

Kirk Baillie  

It would be much more of a hobby at that point.

Mark Littlewood  

Microsoft has got this group of people that have been there since the very, very early days. And I know some of them are still engaged and still sort of work incredibly hard and fly around the world doing stuff. But they’re known internally as the volunteers because they’ve made so much money and some of them are still around kind of 25/30 years later that they have this sort of this great thing and doing it: we’re not quite there yet.

Kirk Baillie  

But there are companies who have have come out of 2020 much stronger than they went into it because the the provided something that was needed and something that the whole world needed all at the same time. I remember reading that, you know, that Zoom had to increase their servers it was like 300% every week for about two months because they were just being inundated with new registrations.

Mark Littlewood  

There’s some really interesting alumni businesses have been through business software conferences and gone through the process. And now I can’t find it casually. As I said, there’s a Google Docs, you can just kind of track company stocks and do a calculation but there’s six come The knees between them that founders have been divorced more than once. And not all of them have spoken but Shopify, Atlassian, constellation software, mimecast, HubSpot, and Twilio have gained $221 billion market cap. So almost a quarter of a trillion dollars in the last 12 months. Which is pretty staggering.

Kirk Baillie  

Yeah.

Mark Littlewood  

That’s, and that’s been settling down over the last month or so. But yeah, there are certainly certainly some pretty interesting businesses and and lots of private ones as well. Lots of lots of companies like Zapier and Doist have the online collaboration enablement, tools, all those sorts of things have been in a in a great position. But I think we’re very lucky in the software industry in that I think there are clearly a lot of different sectors, everyone has been affected in some way shape or form by what’s been going on in terrible situations worldwide. But we, on the whole, our knowledge workers, and reasonably tech savvy and lot of companies are actually targeting and focused on solving problems that more and more people are having. So that’s a good thing.

Kirk Baillie  

While we’re reminiscing in hindsight, if you were to go even further back all the way to 2006, before your first BoS conference, what would you tell yourself?

Mark Littlewood  

First thing, I think, would be jump at the chance to go to the first one, and kneel and vited me and I was doing something that felt quite important at the time. But if I’d realised quite What a life changing experience, it would have been to go to that I would have made different plans in that first year.

I think I have the courage of my convictions be clearer about laying out a position and a position for what we’re about and talking about, why we why we exist, don’t over expand, I think we probably could have grown in different ways earlier on. I think there is this magic thing about a relatively tight group of people, where you have this kind of high density of quality of people. I always say it’s better to have 25 brilliant people in a room of 30 than 200 brilliant people in a room of 300. And it’s about the math and the the higher the density of people that are sparky and interesting, the more likely you are to bump into other people. And I think, you know, doing more things that really focus on that. connecting those smart people and thinking about how we get them to interact more would be a bigger thing.

I’d also have done more online stuff earlier. Now I’ve realised what a useful thing it was, it was never quite the priority. But I mean, I think for a significant group of people in our community, the online stuff is is way more energising way more valuable. So yeah, 

Kirk Baillie  

Tell me if you could step into my shoes right now – as in you’re sat in front of Mark Littlewood, CEO of Business or Software – what would you ask you?

Mark Littlewood  

Hmm. Oh, Kirk that’s a good question! Thinking very quickly on my feet. What are you most proud of about Business to Software?

Kirk Baillie  

And that was ironically and 100% honestly, that was my next question. 👀

Mark Littlewood  

I think the thing I’m most proud of is the difference we’ve made to people’s lives. And that sounds very soft, but it’s the things that you hear. And we talked about Greg’s talk before I’ve had messages from people who literally have said they watch that and they feel it save their life. You can have much more impact on someone than that. But I think, you know, we’ve helped people think about the challenges. We’ve played a very small part in helping some really, really great businesses have huge impact on the world get going, we actually have made a difference to some of the speakers as well. And some of the speakers that deserve a voice and are super interesting people.

I think, maybe my proudest, so this is Badass – Kathy Sierra’s Book. And in the acknowledgments I get mentioned and Business as Software gets mentioned in the first paragraph as this wouldn’t exist without these people. And I think this is a it’s a super valuable read. It’s super important. But I think Kathy is one of the most amazing human beings out there. I think. We were very instrumental both as a community and me as a conference organiser in getting her back into public speaking. And I think I know, we’ve made a difference because of that, but yeah, it’s the softer things. I think it’s the things that make a difference. So yeah, those are things that you remember.

Kirk Baillie  

Awesome. Mark. It has been a pleasure as always, I mean, I’m sure listeners are very aware of who you are now, but where can they get in touch with you or connect with you online?

Mark Littlewood  

I have a very anonymous online presence. I’m Mark Littlewood – I know that’s always amusing for Americans – on Twitter and on LinkedIn. I’m mark@businessofsoftware.org

So yeah, find me there. I think I’m that on Facebook, but I haven’t been to Facebook since September. So don’t message me that – hopefully people left me birthday messages. That’d be really bad. I go back to Facebook one day like kind of looking at so Okay, I’m gonna go for whatever reason, and literally, no one said happy birthday!

Kirk Baillie  

Before we wrap up, we have BoS Conf Online.Spring coming up on the 26th and 27th of April 2021. Do you want to say a quick something about it before we go?

Mark Littlewood  

Yes, but only in preparation for the quick something that you’re gonna say that’s much better and corrects my mistakes? Yeah, we’re really excited about it. It’s the third online event we’ve done. I think we have got a format that brings together some fantastic talks.

We’ve got Wade Foster from Zapier, Amir Salihefendic from Doist, we’ve got Joel Gascoigne from Buffer, all sorts of really, really interesting people who are talking about growing, running a remote business continuing to grow thinking about resetting the values and the goals and the objectives for their businesses.

We’ve got Yodit Stanton, who’s talking about the future of work and the workplace, she’s got some really interesting things to share about different approaches to what the office is going to look like.

We’ve got Scott Berkun talking about why designing design is important and why it’s not something that you should rely on people with silly glasses to do. Design is a really important part of everything.

Simon Wardley I’m really excited about he has developed this strategy tool called Wardley maps, no idea where you got name from, but it’s an open source tool to help you understand the world that you’re living in, what you’re good at what you’re not, and how you can get to be a long term sustainable business.

And the talks are always designed online to be interactive and collaborative, not broadcast. And that’s something I’m excited about. 

Mark Littlewood  

I think more important than the talks (don’t tell the speakers) I think the breakouts and the birds of a feather sessions and things like that are super interesting, just because you get to spend time with just incredibly bright people, some experts, but small groups of people where you can share problems, and also think it’ll be fun.

Kirk Baillie  

Head over to businessofsoftware.org/spring to grab your tickets for the conference coming up on the 26th and 27th of April 2021.

Mark Littlewood  

What was that date? Was it the 26th and 27th of April?

Kirk Baillie  

26 and 27th of April 2021.

Mark Littlewood  

Wow. Let me just say that again, in case I forget 26th and 27th of April. I’ll mark it in my calendar now. Kirk this is lovely. We should do this like every day. I really enjoyed that. Thank you

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