Duane Jackson: How I Came to Appreciate Big Companies

When Duane sold KashFlow, his first business, he exited early from his earnout after suggesting he might set up a workforce union – he wasn’t keen on working in a large organisation… 

Two successful company exits later and following the acquisition of his third business, he’s been with the acquirer for over three years. What changed? It wasn’t the acquirer – in both cases Iris Software – one of the UK’s largest private software companies. Duane discusses how his views on entrepreneurship, starting and selling companies has evolved over time and appreciating different perspectives has been a central part of his growth as an entrepreneur. He also shares some of the things that have made his companies such irresistible targets for acquirers.

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Transcript

Duane Jackson 

Hopefully I spoke to enough people, one to one, to lower their expectations for this. I don’t even remember agreeing to do this talk, and I certainly didn’t agree to I’ve disowned the title with everyone I’ve spoken to as well. So where this goes?

Mark Littlewood 

We’ll get to that. Do you want to be here?

Duane Jackson

Yes, absolutely. No, absolutely hate it, and I haven’t done it other than for the Princes Trust, where I have obligations to do it. As soon as I sold the business, one of the things I was really relieved about, other than never debugging a VAT return, the second one, was not having to do public speaking anymore.

Mark Littlewood 

Wow.

Duane Jackson 

So I only agree if you can do a fireside chat, you can do zero prep. If it all goes horribly wrong, it’s at least as much your fault as mine?

Mark Littlewood 

Oh, it’ll be far more my fault. So the reason I asked Duane, and I know him reasonably well, and he’s one of my favorite people to come back this year for this conversation, was that I don’t know if everyone’s heard of LinkedIn, and they’re all those sort of fabulous, hey, blah, blah, celebrating 10 years of unemployment or little notifications you get. You had a notification came up recently saying Glen Jackson is celebrating three years at Irish software.

Mark Littlewood 

That can’t be right.

So that’s a long time to be at Iris Software for Duane, and we’ll put this into context in a minute. The first time Duane started working at Iris Software, he lasted six months. He sold his company to Iris, and obviously, and you’ll start to understand why soon, loved working in a loved working in a big institutional software business. But he worked out pretty quick that there was an exit, and he sat down with his manager and said he was really enjoying stuff, but.

Duane Jackson 

I’d start a union.

So I done the handover. So I agreed to six months do a handover, and they’re holding back 10% of the proceeds to ensure that I turned up to do the handover. And within six weeks, it was done, and I went around to the various people, said, Look, do you agree this will hand over you? Will hand over? You’ve got your hands around this now, and like, oh yeah, you’ve done it, and we’ll also confirm that you did it. You can get the credits. I don’t care who gets the credit. I just want confirmation that you’ve got everything you need from you. There’s nothing more you need from me, right? And speaking to my then manager, whose ancient history hasn’t been there for a long time, at the time that we’re but you’ve agreed to come here, you got turned up for six months. But what do you want me to just be here and set an example? Did you want the CEO?

And the other problem was, of course, I’d never get out of bed early. If my staff see me in the office before 10 o’clock, they worry, why am I there? But there was so in the last minutes of due diligence from the paperwork together when we’re selling the business, my admins, we haven’t got employment contract for you. Of course, you haven’t. I’ve never sung, and we just need to sign Okay, so my employment contracts in a bundle, nine to five. They’re like, well, you have to turn up for the next four and a half months, and you need to be at nine o’clock, because it says that you need to be set an example. And there wasn’t a way out of it until our suggested setting up a union. And, OK, let me go and speak to somebody, because I’m not sure we’re looking to do that. And I got to go home and do my garden leaf.

Mark Littlewood 

Whatever it takes. And the second time you ended up at Iris.

Duane Jackson 

The second time, well, that’s the same company. It’s 10 years later. The company’s significantly bigger, probably 10 times bigger than it was. Iris has grown in that time. Completely different management team. I already knew the chairman there fairly well, and actually, although I had a one year earn out, I’d said I want to be here this time. I want to stay a bit longer, because I’d been on the sell side of a transaction three or four times by that point, and was curious as how it works from the buy side. I also stupidly wanted to get out of my comfort zone. So 40 people in less companies, 5 million or 10 million in less. Arr, I’m fairly comfortable. Iris is a different beast. By this point, it’s two and a half 1000 employees, revenues in the hundreds of millions, profits in the hundreds of millions as well. So I was curious as to what it takes to work in that environment and how those businesses operate.

Mark Littlewood

Interesting. So that’s two companies sold. How many other come? Or have you sold any other companies?

Duane Jackson 

So two that I found, well, it depends what you believe.

Mark Littlewood 

Well, depends in do you want to be a LinkedIn thought leader?

Duane Jackson 

No, exactly. You told me. So after I sold the first one, and you said, I guess what you’re doing now, and I changed probably my Twitter bio to advising and investing, he said, You can’t do that. You sound like an asshole. So I changed it.

But so I’d sold Kashflow. Then in interim, I was very heavily involved with company called Breathe HR, and was very involved in the process of selling breathe, which is a great process for everyone involved, and worked out well financially. I then started, if you remember, something called sup date, that was investor updates. So I’d already built that, but that wasn’t really a start. It was more a product that I think needed to exist and that I wanted to use to get my coding skills up to date. So I built that, and then I had the idea for the next thing, the payroll thing, and I knew the question would be, but what happened to that thing? What happens that? And again, it’s about failure, right? I don’t want that to be seen as a failure, so I arranged a soft landing for that, and cloud cube acquired that. But if you look at the tech one chart, call for the Kashflow acquisition, the price wasn’t being divulged because I was probably embarrassed about how much they paid me with the crowd cube acquisition, which was also on the tech watch. It wasn’t divulged because I was embarrassed about how little they were. I was like, I’ll just take anything so I can have the headline and and the end of the narrative to give me the clear run to them focus on Staffology, payroll.

Mark Littlewood 

So you’ve obviously studied computer science at university. Should we go back to the beginning? Yeah, should we go back to the beginning?

Duane Jackson 

Well, if I start rambling, to reign me in. So I’ve got a very, probably non conventional background. So I grew up in the East End of London, in Newham, in various children’s homes, left school at 15 with no qualifications. So I kicked that at one school, the second school, I just started bunking off. No one seemed to notice, so I stopped going. And I recently done a subject access request on Newham Council, and saw the letters, and basically, we’re not going to put him forward for his exams, because he’s never here. So didn’t see any GCSEs.

By the time I was 19. I so I need to rewind a little bit. So we won the children’s homes. I picked up a ZX Spectrum in the period where I was out of school. They said, You can’t watch TV. You have to be doing education. And I said, Well, can I play with that thing? So ZX Spectrum, which was pretty old at that point, and the manual for it, sought myself to program and absolutely loved it. And I don’t know, I’m sure some of you are familiar with something called the hackers manifesto. There’s basically a part in there that really, really resonated with me, and that was, if I tell a computer to do something wrong, it’s because I instructed it wrong, not because it doesn’t like me. Didn’t get laid last night. Shouldn’t be a teacher in the first place or a social worker in the first place, and all these other myriad of indecipherable reasons, I just wrote it wrong so that really knowing where I stood with it worked well for me as a 12/13 year old. But anyway, so in that environment, I ended up involved with. People ask, how did I fall into crime? I didn’t fall into crime. I grew up around it. I was the odd one out, not being that involved with too much crime until I was 19/20 and then I was involved with international drug trafficking.

Mark Littlewood 

Logistics.

Duane Jackson 

Yeah. Basically, logistics, yeah, logistics for little white tablets, and ended up being arrested in 2000, no ’99, in Atlanta, Georgia, with six and a half 1000 exit tablets, and went to prison in Atlanta, Georgia, where I was looking at 25 years. Thankfully, I managed to come back to the UK to await trial in the US. And whilst I was here, the UK Police arranged an administrative, administrative dismissal in the States, which means the I can still come arrest me even today, if they weren’t too flimfences, they’ve not been dropped. So I was then charged in the UK, where, rather than 25 years, I was looking at 16 years.

Mark Littlewood 

You got all the luck.

Duane Jackson 

Yeah, I know, really lucky. And then we stood trial, and actually you got five years so, and the judge actually said that he’s for the sophistication that that gang was up, which I can’t take any credit for. I was a small cog in that machine, but he was used to seeing drug gangs of that sophistication, being people in their 40s, not in their early 20s. And so we all obviously had something about us, and he didn’t want to ruin our lives. Therefore, He’s given us the lowest possible sentence he could. So, yeah, served a five year prison sentence in the UK. I’m getting through a lot quicker than normal, which is great.

Got out of prison and started a business with the help of Princes Trust. One man, web developer in 2003 and at the time, noticed that, so I had to build my own bit of software for doing my invoicing, because everything was really clunky at the time, sage and quick works were the only options, and that evolved to become a company called Kashflow. You fast forward to 2013 and I think legally, I’m still not allowed to say I sold it for 20 million by sold it for a number in 2013.

Mark Littlewood 

But an undisclosed number.

Duane Jackson 

Yeah, an undisclosed number.

Mark Littlewood 

Still this morning, working for a well known but nameless British broadcasting company.

Duane Jackson 

Exactly. So that’s the short version.

Mark Littlewood 

Yes. You started again. So, I mean, incredible story. There’s a bunch of stuff that you can dive into there. What were the two or three biggest things that you took away from Kashflow? Actually, what are the other two, apart from money that you took away from Kashflow?

Duane Jackson 

What? In terms of the experience of building it? That’s a wide ranging question, isn’t it?

Mark Littlewood 

You’re a wide ranging kind of guy.

Duane Jackson 

Yeah. So one of the things I realized was all the cliches are cliches for a reason, because they’re true. So you hear time and time again that even though it’s a software company, it’s all about the people and having the right people. It’s true. That that kind of stuff really is important.

One of the things that took me too long to realize was that I needed coaching as a CEO, I was a terrible CEO for a number of years, so I was thinking earlier, when we’re talking about failures, I remember we had a product owner, product manager, Ian, really good at his job, and we been for a few that were awful, and Ian was brilliant. Then he comes to one day and says, right, you’re not gonna be surprised, but I’m handing my notice.

What do you mean you’re handing your notice? Why? you’re brilliant.

He said, Well, you’ve not spoken to me for the last year. Said, Well, why did I speak to you? You’re doing a great job, which was the way I saw it, right? Yeah, so, but yeah, in the last 18 months, so I learned a lot when I tried to sell the business in 2010. So we got to 2010 I was still the majority shareholder in the business, and was all the way through to the exit. I actively tried to sell that business because I wasn’t doing my job anymore. I knew what I wanted to do with it, but didn’t have the capacity to do it because of all the stuff that has taken up my time day to day, to try to sell the business and realize a few things.

So one was, I really thought bigger companies would know how to come and run this properly, right? Show me how this should be done, and you realize very quickly. No no no, they don’t understand this at all. And actually you can probably teach them a thing or two, which was insightful for me. But also I got to the end of that process, no one went to buy that business.

But one of the people I met in the process was a guy called Subrah Iyar, who had founded WebEx, and so it’s Cisco. And he said, Look, I’m not interested in the business, but I’m here for a few, few more days in the UK. Find you really interested in let’s, let’s keep talking. So I spent some time with him, and he helped me to realize the reason I didn’t sell the business, and the reason is the same reason wasn’t enjoying my job. So you remember back when I had a fair amount of media coverage and I got accolades, they’re doing very well because it’s bootstrapped and from my background, whatever else, but Subrah said what no one ever points out about you is you’re doing this all on your own. You don’t have a C suite. You are CFO, CMO, CRO, CPO. You’re everything. That’s why you’re not enjoying the CEOs job, because you’re not doing it, which is also the reason no one wants to buy your business, because if we give you millions of pounds, you’re going to walk away tomorrow, regardless of what you say and who’s going to run this business? So then I spent two years building that C suite around me so that when we did set the business, I could walk away after six weeks.

So yeah, realizing the importance of people in a business, I think, especially as tech is we overvalue code and undervalue people sometimes.

Mark Littlewood 

Yeah, talk to us about the second Iris. I’ll just talk, talk through the founding the company. So did you set that up for a quick sale?

Duane Jackson 

Essentially. So I remember, I can still picture exactly where I was sitting. So I wanted a technical challenge. We hadn’t sold Breve HR at this point, and breve kept asking me that the ball that we really need a web based payroll with an API. There isn’t one. Do you know of one? And looked around, couldn’t find it. So Xero had a bit of an API. But I know Gary Turner was running Xero in the UK pretty well, and had a chat with him. It’s like, okay, so they’re not really majoring on this API. It’s there, but this isn’t going to do what breathe needs.

I was also involved in Crunch, which is a high tech accounting accounting firm, really, they needed the same thing. So payroll was a real bottleneck, because you had to put an army of people to do it, because there was no API driven product. And it was a running joke at both those companies for that, I should go off and build it. But it was said enough times that it obviously planted a seed.

I remember the technical challenge is with payroll, there’s no such thing as an MVP with a CRM product or a HR product. You can do a basic thing and people can use it. Payroll needs to do everything on day one, otherwise no one’s going to use it. Just because no one’s pregnant today, they might be tomorrow, so you need support S and P and everything else. It’s commoditized. You can only charge a pound per pay slip. Hence why there’s not been much innovation in that space, because there’s much more appealing things to do, and you need to do the annual updates every year. So that felt like a real challenge, and I was a bit bored, so I sat down, and before I knew it, I’d built a fully working payroll engine, but I really didn’t want to do a start up again.

But looking around, I knew that these bigger businesses had a problem, especially those like Iris access groups, Sage that have acquired lots of products, they have multiple payroll products upgrade each separate, distinct code base every year with a new configuration. So built something that I knew would make their life a lot easier, and built that to sell to one of those.

Mark Littlewood 

So you really thought about the architecture and the technology.

Duane Jackson 

Yeah, horribleness, yeah, awful. And we were in the process of rewriting that in .net when we were acquired. But even in 2000 and 4-5-6, when I started writing that, VB script was outdated. So by 2013 when I’m selling it, very much. So, so yeah, as well as giving a lot of thought to the architecture of that and building that in a certain way, also to the way I set up the business and kept that very clean and make and making sure that worked for due diligence, so there were no employees to worry about. If anyone were to buy it, it was just me. I use one or two contractors to do bits and pieces, but mostly it was just me. Yeah, and just made sure that if anyone did buy it, it would be very clean to buy.

Mark Littlewood 

So you had no employees when you sold the second or the second company to Kashflow, yeah, which is pretty much the opposite of what you were saying with. Sorry, with Kashflow so you have 40 staff, yeah, you were basically doing all the big jobs and then.

Duane Jackson 

Not by the time, yeah, exactly whereas, yeah, Staffology was the exact opposite. There was just me. So only me that really understood the code. Also, I’d learned a lot negotiation wise, so I was getting paid very well, and they wanted to make sure that a part of that they actually needed a whole bunch of additional features that weren’t there. So I said, Look, stay for a year. Add these additional features help us to understand the code base, so we can manage it internally, and then.

Mark Littlewood 

So you went in even leaner for that.

Duane Jackson 

Yeah, yeah, exactly.

Mark Littlewood 

And that was a conscious.

Duane Jackson 

Yes, exactly. And I even said when I was talking to the chairman there negotiating the deal, and even when I was there for that year, you had this attitude from everyone. Well, what do you care? You’re going to get your own out in a year, and you’re gone. I know I’m staying honestly. I do care about how you’re doing this and how you’re doing that. And I said it so many times in that first year that by the time my payout was all done, by Christmas, 2021. I kind of had to stay now, right? Just because I said to everyone I would otherwise look like a told you so. So, so yeah, so stayed for another two years now, so I’m leaving at the end of next month, which comes the end of that journey. But yeah, stayed for another two years and learned a hell of a lot about.

Mark Littlewood 

So what in that bit? Because this is really interesting to me, because this is what’s. You’ve been tied there. You’re essentially a volunteer. You’re being paid, yeah, but you would not be there if you weren’t.

Duane Jackson 

No, I’m there voluntary and held sort of golden handcuffs or anything like that, which everyone that knows me, including you, like, Sorry, what?

Mark Littlewood 

Yeah. What are the what are the things? And I’m really interested from both the perspective of an entrepreneur selling a business and entrepreneurs that are purchasing other businesses. What are the kind of things that are keeping you excited and engaged, because you have a relatively low tolerance for.

Duane Jackson 

But my main thing so it evolved over the years, and even so today and yesterday, some of the talks about have helped me sort of articulate more what it is I’ve seen. So something Bob said yesterday, right? So I’ve been at Iris, and especially in the first year, the amount of what the hell are these idiots doing moments I’ve had. Why? You What’s wrong with these people? And as Bob said, they don’t. People don’t people don’t make irrational decisions. You just don’t understand their context. And that’s exactly what it was, right? I didn’t understand where they’re coming from.

Yeah. So it was the learning more stuff about how these companies work, and kind of intrigued by it. So what, what attracted me to it? How I, if you asked me three years ago, why do you want to stay there, it would have been, I’ve built this. So I’m really good at really shitting allergies. So I built this little train carriage. So that was Staffology, right? And it was really cool, and I could use it. Iris had this big fuck off train set of all these bits. So I was quite excited to naively think they’re going to let me get my hands loose on that stuff. And I still think we could learn some really interesting technological stuff. But for reasons we’ll come on to it is obvious why they didn’t let me do that. Instead, I was there and trying to get dev process working around what we’re doing on Staffology and learn other lessons while I was there, and also on the buy side of M&A. So I’ve been involved in some of that, which is completely separate sort of stuff all of you stuff, because Iris, some of you might know them, some of you might not, but payroll is a small bit of what they do within HCM, and HCM is a small bit in what they do with because they also got accounting, education, software. They’re a huge company.

And my realization now, right? So you talk about Kashflow and a lot of smaller business or sub 100 employee businesses as a small software company. You talk about Iris as a big software company, and we’re saying the only difference is, one’s little, one’s big, and that completely misses the point. They are completely different animals playing completely different games, and that’s the context, right? So for a start, and I’m really only come to appreciate this in the last few months.

For a start up, your financial recite, resources are fairly finite. You might have raised a load of money, but you’ve got a runway. You have to take risks, because you’re creating something new. If you’re not almost failing, you’re not really getting anywhere. Contrast that with a business that has a couple 100 million in profit, that runs payroll for 20% of the UK paye population, all of a sudden, you don’t want to move fast and break things. One, because you don’t want to damage the cash cow. Two, you don’t want to screw up everyone’s payroll. So you move much more slowly, and it’s a completely different beast. And so whilst I’ve gone in there with this, we’re going to optimize the development process. We’re going to do Agile in a certain way, and we’re going to make this work and predictable development and a good release pattern. They’ve got a different game that they’re playing, right?

Mark Littlewood 

Duane, we might set up a union.

Duane Jackson 

Exactly that. So, yeah.

So, the key point, right? So he’s appreciate so someone said to me, and people said, oh, so what is it you like about big companies? And whoa, whoa, whoa, whoa, whoa. And if you Google the word appreciate it, just means, so I was saying to you before something, I use the word manipulate. And some say, Well, that just means to handle with care. So yeah, I am manipulating you. Okay? No, I like that. So I looked at appreciate, and that just means to fully grasp, right? So I now grasp what big companies are about.

Mark Littlewood 

What were the mistake when you were looking at acquisitions at Iris? What were the things you realized you could have done differently when you were on the other side as an acquired company?

Duane Jackson 

Yes, I probably can’t name names, right, but.

Mark Littlewood 

You can.

Duane Jackson 

Yeah, but I shouldn’t.

Mark Littlewood 

Go on, go on, go on.

Duane Jackson 

So one, so a lot of it was more on the stuff they didn’t buy. Because if you’re sending something to a big company, you need an internal champion that really understands why they want to buy you in it, and it ticks a box for them, fills the hole, and they’re the one going to bat for you. So why we should buy this? And there was a company that did something in an adjacent space, so basically, payslip distribution, essentially, and that was up for sale, and I couldn’t get Iris to get interested in it, and I kept pushing it and pushing it to a point where I was like, Okay, well, I might go and buy it, and spoke to the guys, and we could have done a deal before it’s too close, as a conflict was doing. So I didn’t, but I couldn’t convince Iris to buy it. And then, in the end, a big data company that his name might run with Wixberian bought it and use it and and they are doing with it exactly what I was saying to, you can buy this and you can do this. And they hadn’t, they didn’t, but that other company bought it and did that.

Mark Littlewood 

Wow.

Duane Jackson 

So understanding the internal process of how you have to work in this guy. So I’ve learned skills I don’t think I want to have as well. I’m saying so I think now, if I live my time again, I could have got them to buy that company, because I know now how to champion and one of the.

Mark Littlewood 

You’ve got skills that you could appreciate?

Duane Jackson 

Yeah, maybe, turns out we define appreciate.

But the other interesting thing that was really hard and still is is you have to learn to work with people that you didn’t hire and you can’t fire. Because that’s the way these organizations are structured, right? So you have to work with people that normally you wouldn’t, especially when you’re the CEO or your C level, you’re responsible for everyone. Then somebody you don’t think is the right fit. I can’t do the job. You can replace them with somebody else in that environment. You can’t. So that’s definitely a learning experience for me.

Mark Littlewood 

Interesting.

Duane Jackson 

Yeah.

Mark Littlewood 

I open up to questions because in a minute. But what’s next? Because just broken, broken cover on moving on. So how many houses have you remodeled? You’ve probably run out of.

Duane Jackson 

Done enough of that.

Definitely done enough of that. So, yeah. So I think first time around, I tried to learn golf and realize how seriously other people take it. Like, I know this isn’t for me. This isn’t fun. So yeah, learnt like, I can’t, can’t retire. I mean, I enjoy what I’m doing. So why would I? So my mentor, I remember speaking to Sir Lord Young. He was in his 80s at the point, at that point, and somebody else that was very soft. So why are you guys still working? I said, Well, we enjoy it. What’s we going to do. So, yeah, I enjoy building products and software companies.

See, I don’t know the answer to what next. So I certainly don’t want to do a small I keep saying this. I don’t think I want to do a start from scratch again. The space I know really well is the legislation, sort of space in terms around the payroll accounting and that kind of thing. So possibly might do something in that space. I’m barred for a year, so in a year and one day, you might see something if I go down that route.

I think what’s interesting with Staffology. And so Iris acquired that because it’s a very modern cloud platform that they’re then they’re putting a lot of investment into that. As they go forward, cloud platform, where I don’t think they necessarily appreciate parts of what’s on there, in terms of it. It was an API first product, so I built that in such a way that so with Kashflow, we bolted on an API. A lot of people do, right? And then you add a new feature of projects in your main app, and you develop a community like, can we get that to the API? Not yet. We’ll add it there. And I know that was really frustrating for developers.

So with Staffology, what I did was built the API, and the UI is an API client. So although a lot of our customers don’t care about the API, they don’t even know what an API is. There’s nothing you can’t do in there’s nothing you can do in the app that you can’t do with the API. And for Iris, that’s interesting, but not really the main show for them. So I still think there’s an opportunity in that space, because in my head, that dealt with the commoditized issue of one pound per place, it was a maximum, OK, enable lots of throughput, and you do have an API. So I think there’s interesting stuff to be done there still. So I might go back into that space, but then it feels a bit like I’ve done that. So do I really want to do that again?

Mark Littlewood 

Well, you’ve built a decent sized company, 40 people. Sold it for an amount that you can’t talk about, but you probably made less than what you sold as zero person or one person company for.

Duane Jackson 

So, so I made more on the zero person company. Yeah, that I was building for two years.

Mark Littlewood 

Yeah, because you had no investors.

Duane Jackson 

For me, I think it might have been you again that pointed it out when I sold Kashflow for a number that runs with Wednesday million, I think you were surprised how much I’d personally made from it, because we’d see all these headlines in Tech Crunch so and so, so for 150 million. So I thought that’s a fairly small sell, really. But then you find out how much the founders made, oh okay.

Mark Littlewood 

Make nothing on 150 millions.

Duane Jackson 

They’re so diluted from VCs and co founders and whatever else. And I slam the majority of the company when I sold it.

Mark Littlewood 

You had, again, just keep falling on your luck, Duane.

Duane Jackson 

Yeah.

Mark Littlewood 

You got a great investor.

Duane Jackson 

But the point was made earlier that we delete our failures, right? We forget them, or we reshape them. Because you could say this update was a failure. We we retell the story right, to fit with our own narrative. And yeah, and actually, I think my time at Iris is has been a bit of a failure, because I I would love to have worked with the dev teams there and got the processes run differently, and worked with my opposite numbers in management very differently than I have, but it took me way too long to realize the approach I’m taking here is not the right approach. So I think really on reflection, yeah, my time in Iris, I think I failed in doing what I wanted to do there, but I learned a lot in the process.

Mark Littlewood 

Interesting. I think redefining failure is great. Somebody came up to me at lunch and said, Oh, that was classic, the talk before about failure, and then you were talking about failure, and then I backed into the thing and knock the things open and smash.

Duane Jackson 

He done it on purpose, though, right?

Mark Littlewood 

No, I didn’t show it on purpose, but I was just really staggered that was seen as a failure, because that was, like my biggest triumph.

We’re going to open it up to questions, because there’s a few things we haven’t talked about. There’s a whole bunch around. Well, the things that we’ve been talking about here, but the kind of the back story, but I think that’s the things that you have done, from marketing perspective, some of your companies, I think, are nothing short of genius. Who’s been in a little session with Duane over the last couple of days?

Duane Jackson 

So everybody had all the stories.

Mark Littlewood 

Who’s learned something? who’s going to have a question that’s framed around one of those things that we should share with anyone else. I’m going to say for the moment, and we will. We’re going to go to questions a it’s so great to have you back.

Duane Jackson 

Thank you.

Mark Littlewood 

Thank you. Thank you. So so super excited when you said yes.

Duane Jackson 

I didn’t say yes, I still haven’t said yes.

Q&A

Mark Littlewood 

Well, when you said, I’ll think about it. Yeah, what walk on music? Questions. We need a mic at the back. Quick, Calvin. Was it yours? Quite someone had a question. Oh, dear Lord, and there’s ok one. Imogen. There we go. Right. Let’s get Ian on that side.

Audience Member 

My first question. I’m very intrigued to hear about the marketing stuff, if you can go into that. But I was also very interested in how you went from your initial journey, kind of leaving prison to building Kashflow, like, how did you find the problem? How did you set up the company?

Duane Jackson 

So when I was finishing my sentence at Ford prison, I don’t think I knew anybody that had started a business or ran a business from where I grew up, nobody. And I haven’t given it much thought, this is before the Apprentice and Dragons Den, right? So it’s a different world now, but I’m sure if you asked me back then, I’d have assumed you need to have gone to Oxford or Cambridge and you probably need a license to start a business. Would have been my assumption.

Mark Littlewood 

Your guess.

Duane Jackson 

Yeah, but some volunteers from the Prince’s Trust came in towards the end of my sentence and spoke about what they do. Was called the Enterprise Program. And not only was I allowed to start a business, even given my big black hole, my CV that I was going to have when I got out in a few months time, that they’d support me in doing it and give me a small amount of cash to get started as well. So that really got me excited. And I started working on a business plan when I was in there, you have a different class of criminal at fault. So there were people that could help review my business plan, dodgy, solicitors, barristers, all sorts of. Yeah, completely different.

Mark Littlewood 

This lot would go hard enough.

Duane Jackson 

It’s very different. So Brixton and the Isle of Wight where I done, or even America, yeah. So when I got released, I went straight to Prince’s Trust. And I think I genuinely thought they were going to say, well done. Pat on the back, here’s a check for five grand, off you go. But no, actually, they made me work a lot hard on my business plans. You’ve not done any competitor analysis. I’ve done any what analysis? So they helped me do that through a course that they put on. And I went through that journey with the Prince’s Trust. And then I did get a grant and a loan to start that business, but that business, but that was starting as a one man web developer, and it was only when I was in that position as a web developer, and again, through courses that Prince’s Trust put on, realizing selling my time by the hour, I was limited to how much money I could make, so really need a product. And by the time they said that, I’d already built this little thing for my own invoice in and a few other Prince’s Trust businesses were using it, but I hadn’t joined the dots. Go, hang on, I need to build this. And that’s where the idea of Kashflow came from. And actually I became, although I got help from the Prince’s Trust to start a business, and 1000s, hundreds of 1000s of people have over the years, I became the first to go full circle, and when I sold the business, wrote a big check back to the Prince’s Trust and became a patron of the trust. So now the king goes around telling my story and gets it wrong, but nobody will correct him, because he’s the king.

Mark Littlewood 

That’s pretty awesome.

Duane Jackson 

Was there a second part to that question? Did I cover it?

So, there’s a lot of it was guerrilla market and stuff, I think we’d call it now. And what I spoke about in the groups was specifically that the sage wars is what I’d call it. So I wrote about that there’s a book called 4000 days on Amazon. You should be able to get the Kindle version for free as from tomorrow, because it takes a while when you mark it as free. But there’s a chapter in there on it, and we basically found the giant in our industry that was sage, a big elephant with a little mouse and jumped on their back and waved a flag to get attention. And that really worked well for us. Very low cost.

Mark Littlewood 

Really annoying. I mean, like, I mean, not just like, yeah, really annoying.

Duane Jackson 

So I’m trying to remember her name now the news reader. So I only did this stuff for the Prince’s Trust, right? And what the last time I was on stage was with Michael Dell and Zach somebody that runs an F1. That’s one Zach Brown, yeah, so Zach Brown and Michael Dell, so they were on first talking about the market, and they’re done. And me foolishly, was on, was on the table with the news reader that was interviewing us all, and having a casual chat with her and talk about the someone else brought up the sage stuff. So we’re talking about that. She was very friendly. And then I got on stage. She turned on me. Because, because it was very aggressive. And some of it you, I mean, none of it was ever personal of anyone there, but it was very aggressive. And she was somewhere you obviously must have annoyed a few people doing that. And it’s only after I got off stage I thought was the right answer, right? So for Zach Brown and Michael Dell, they were gentlemen boxers. What they were doing, right? That they could afford to lose. And they were scrappy. They were gentlemen boxers. What I was doing was street fighting, and that was the difference. Whatever I said on stage that day was not that nowhere. It was a mumble and a bit apologetic, but that’s the true answer.

Mark Littlewood 

Yeah to be fair, you didn’t really hate them. They hated all the people there. Hated you. You didn’t really.

Duane Jackson 

Not even the people there. They thought was great, the people, they found it really insane, other than maybe the board I saw some. So my mentor died just over a year ago. So, and there’s all this stuff that he said to me that you can’t say this until I’ve died. He’s now died, and these things keep coming back to me.

Mark Littlewood 

Tell us about your mentor.

Duane Jackson 

So my mentor was Lord Young who ran Caleb and wireless. He was in Maggie Thatcher’s cabinet. So Maggie said about him, other people bring me problems. David brings me solutions. There’s a famous quote about him. He’s in David Cameron’s cabinet as well as an enterprise advisor. Yeah, an incredible guy. He put a lot of time and energy into mentoring me, but because he was a very high profile business figure, the board at Sage got in touch from said, What the hell do we do about this guy? Yeah, so seeing some of the emails, they were confused. They didn’t know what to do.

Mark Littlewood 

What did he say to them?

Duane Jackson 

I can’t remember. I can’t remember what his reply was, but he very much enjoyed sharing and and he even said like so he done well for me. It was an investor as well, and he’s had lots of other successes. But yeah, he did say that actually some of the most fun he had was, was Kashflow with me, and we did have a lot of fun doing it. Yeah. So where did that come from?

Mark Littlewood 

I think was guerrilla marketing.

Duane Jackson 

That was it.

Mark Littlewood 

What are the, yeah, two most entertaining guerrilla marketing activities that you annoyed stage with?

Duane Jackson 

Yeah, okay, so you might remember better than me now, because I wrote the book on this, and then I kind of deleted. So I wrote the book, so then I keep remembering them. That’s why I don’t get dragged on stage anymore.

But the one I remember and enjoyed the most was a promotion we done was if you send us your copy of Sage with the receipt, we’ll give you a copy of our software for free for a year, so you can use our web based off. Sage actually retaliated and done the same. Send us your copy of Kashflow web based software, and we’ll give which was great because we because we had people that were then coming to us, and I’d always ask customers, where did you hear about us? And we were, oh, you were mentioned on Sage’s website. Sage mentioned you in their marketing. Never heard of you before, so we thought we’d had a look. It looked really good.

But so yeah, we’ve done this promotion. Send us your but we got, we wanted to get that promotion out there, right? No one’s going to write about a slightly clever promotion until you make it interesting. So we made it interesting. When you send us your box of Sage, we’re going to build a bonfire with all these boxes we get, and it’s going to be amazing. So that got the media to pick up about it and write about it. So that was sort of bite one at that cherry, if you like. And a few weeks into it, getting quite so how’s it going? Because we’re looking forward to seeing this bonfire. So we’ve done a YouTube video of just one box slowly burning to the funeral march, one copy of Sage, so literally burning their products. Yeah, I can see why. I got in trouble, I guess.

But that, again, got some more coverage. But ultimately, we got a few boxes of Sage, not enough to make an impressive bonfire. CDs don’t burn particularly well anyway. Probably not good for the environment. And actually they were useful because we’re building migration sources, useful to have different versions to test that migration source. But we’re still getting asked, where’s this bonfire then that you promise us, especially for industry, press, accounting, web and the like. So it’s very sort of inside baseball. So I found the Environment Agency. So what would happen if I had a bonfire? We’d fine you 25,000 pounds of unauthorized bonfire in a public place, OK? So we put out a press release, and we’ve been threatened by an Environment Agency, and therefore there was not going to be a bonfire. So we’ve got a lot more PR, because we’ve been threatened by the Environment Agency. It worked that. OK.

Mark Littlewood 

Brilliant. My favorite moment of delight in software, because I use Kashflow as a customer.

Duane Jackson 

Was it the bank robber icon for the van report? Yeah, Iris made me move out on day one.

Mark Littlewood 

All the tax this little bank robber icon.

Duane Jackson 

Yes, we had to change it because we were sending a lot for accountants as a channel, and accountants didn’t like it either. So if you log into an account that was provided by an accountant, it would have been a much more boring stack of coins or something. But, you know, I like that where little there’s a lot of personality in that software. There really was, I think that’s important, even now, the software doesn’t have to be bo on boring. And especially if you go, I mean, it’s, it’s almost what I’m pretty just converted here, right? But you go back 10-15 years ago, this whole consumerization of business software, it was. Humans use the software. People, not businesses. So make your software human as much as you can. Yeah, there was a lot of personality in there, which, again, when you go into big business, they need to, for various reasons, pull that out often for fear of getting sued. So even with Staffology, you had dummy data to get started. You want to get to values. Customers get to value as quickly as they can, so they convert. So you had a dummy data in there. And everything I’ve done has been themed. So Kashflow was very Simpsons themed with a lot of the stuff that was in there. Some reason was so I’d just watch all the Terminator movies back to back with one of my daughters. So that was all Terminator themed. So you’d see Cyberdyne systems as the example, coming in lots of bits like that. But with Staffology, it was all based around UK actors. So we had Emma Watson Idris Elba, and so Idris Elba had a Hackney address and stuff like that in there as the demo employees. And they’re like, Oh no, we have to remove that. It’s a bit of fun. Why? Well, we might get sued. Well, that’s great PR, if you.

Mark Littlewood 

Fantastic news.

Duane Jackson 

Exactly, coming back to them being a different beast, right? They don’t need the PR. They already own the market, and they’ve got hundreds of millions of cash. We’re not going to risk it by Idris Elba or Emma Watson or Benedict Cumberbatch suing us. It’s understandable.

Mark Littlewood 

Question back here, put your hands out so we’ve got one. Go, yes.

Audience Member 

Fascinating story. It’s my first Bos, and I think one of my reflections is how open people have been sharing their stories in the authenticity, and I think you’ve just epitomized it with your your story. I suppose my interest is you mentioned that you got to the point where you realize you couldn’t do it all on your own, and you were told that you couldn’t sell the business unless you built people around you. Can you talk a bit about that story in terms of, who did you hire first, and how did you build that team?

Duane Jackson 

Okay, yeah, so, first on the first point. So one of the reasons I sort of agreed to do this talk is exactly that, right? Is that this is a feels. I don’t know how, but this was like a very safe space, right? And we’re all very comfortable. And I think it’s, again, it’s very human. So that’s why I was willing to sort of agree.

So on that building the team. So I’d actually been burnt before that, so I’d hired somebody that, funny enough, was ex Iris. And I spoke to the CEO that had been his CEO, when he was saying, Yeah, I think it’d be great for Kashflow. You need the adult supervision. He’ll be great. So brought him in, and he was absolutely paralyzed by how quickly we’re moving, the fact that he didn’t have people that he can go and get all the marketing stuff designed. We’ll find someone to do it. We have to pay some more people. We don’t have anyone in the company that can do it. I think what really highlighted it was Dominique, who was asked the sort of PA, I guess, kind of COO, should get pens from Tescos, the biros normally when they’re on sale, because they were a lot cheaper. And if you need a pen, that’s where they were. And he came over want to know how he can get a refill for his whatever Mont Blanc pen it was. And she’s like, No, you have one in biros. And that, for me, just perfectly illustrated the clash.

So our, done the usual thing took way too long to hide him, too quickly, too slow, and fire him again. Cliches will be in true. So I’d already been burnt once. So yeah, I was reluctant to start bringing outside people, and actually I recruited from within to build that. So Dominique, who I now talk about as being essentially COO by the time we sold, certainly wasn’t in if you go back two or three years, but had the potential to so a lot of it was developing internal people. And a big thing for me was bringing the CEO coach so to help me develop those people, to help me realize what my weaknesses were, and to also help us. So he done the whole values, mission, vision thing, which I just thought was flaky bullshit. Why would anyone do that? But as soon as we’d done the values thing, so we sat down, all of us in a room, right? Write down what you think, talking what values are, write down what you think they are. And when we compared, we were all aligned already. We knew what the values were, because you don’t choose your values, right? You identify them. They’re there. But once we have those defined that kind of thing helped massively in the hiring process for that top thing, because when you’re interviewing someone you like this just doesn’t feel right. You run through right. You run through the values and you mind you go, Ah, yeah, you’re not exhibiting this, that or the other.

So professionalizing the business, professionalizing myself, getting coaching that really helped to build that and then to put structure around what we’re doing. Okay, let’s have a plan. Let’s look each other and commit to doing this. Lock and load was a phrase we’d use after we’re back and forward and challenge it. And went through there. And it was, it was interesting, because actually, there was a guy that you might know, remember the free beards in London that done various events. So Ben South was one of those guys, and he’d been with me doing the marketing stuff, and was really good. And then when Raj came in, the guy that helped me to professionalize it all, okay, we’re doing this now. Ben like, I’ve been here before, so he helped build big games. He said, I know what’s coming. It’s going to be such hard. Such hard work, I’m not up for it. I’m going and, yeah, actually. And that very first meeting that we had with the what was then, OK, get together your top level people. The first thing Raj said is, some of you guys aren’t going to be here in a couple of months, and that’s because you won’t want to be here, because it’s going to change. And he was right, but it worked very well. But it was having a plan, essentially, is what it boils down to. There was a plan to there was a plan to do that. There’s a structured way of doing it, with some external help from somebody that had been there before, to what it came down to.

Audience Member 

So this is going to be a much more boring question, I think. But when you were deciding to start stuffology, your sort of thumbnail description was that it was aimed very directly at a need that you knew incumbents in the big incumbents would need, which was something to replace their core engine. It’s like you said, to prevent them having to upgrade like several engines at once.

Duane Jackson 

Which is an optional right, because you have to have the new tax codes and new NC codes every year.

Audience Member 

So I guess, could you talk a bit more about how you decided that, how you gained enough context, enough knowledge of how the the deep insides of these your competitors were working in order to work out, Hey, this is actually a good thing to build to be a good acquisition target to many large companies at once.

Duane Jackson 

Yes, yeah, really, really simply. So there are annual changes every year, right? And they’re slightly different. Sometimes it’s just the tax code changes and different ni rate. Sometimes there’s other weird stuff. And even more recently, HMRC are driving people mad with some of the crazy stuff mid year tax changes and NI changes, and even the recent drop in ni, they announced that when a lot of people had already started the payroll for that period, and it’s like really? So you have to do these changes every year, and they’re slightly different each year. If I just started this in 2018 and wait for the next change, I’d been waiting a year and then another year. So instead, I built this for 2013 tax regime and put it through five years worth of changes that all this is really cumbersome and fiddly. Rewind, do it again, and then do it. And essentially it came down to a bunch of JSON files. As Steve, Steve weld knows well, he’s doing something similar. And when you said JSON files to me, updates like, yes, good. I was right, because someone told me it’s the wrong approach. But essentially it comes down to a structure in the JSON config, right? Sure all the stuff that you need to change easily you can change easily, and doing it for five years.

Audience Member 

I guess separately from the technical architecture, like, how do you know that was, that was going to be your USP, that was going to get you acquired? Because that involves knowing, like, inside your competitors and what challenges they’re having.

Duane Jackson 

Yeah, so a base level, it’s the does it do what it needs to do? Right? Because this is the great thing about payroll, is it’s very well documented about and HMRC will even give you test cases this input should give you this output. And there’s hundreds of them, so you can check it actually does what it needs to do on the tin. And once you pass that point, that is kind of enough to say that you do the core stuff, but that you write that on its own wouldn’t have been enough. So I had to take this product to market. And did take it to market. But rather than doing what you meant to do, pick a certain segment of the market and target that, I consciously wanted to get a bunch of small employers that were doing just their own payroll, five to 10 people in employ in a business, a bunch of people that are doing direct around payroll, the same thing some big companies that are doing complex stuff and everything in between. So by the time an acquirer looked at it, I had the proof. It was there. I had customers reflecting every single type of customer you’ve got. I’ve got two or three of them on here, so not hundreds, but two or three in each category. Just so I used to know the right phrase, but you’ve got Enterprise Allowance for the small businesses and apprentice levy for the big ones and everyone in between, basically. And a lot of it was talking their jargon as well. Have been able to use those phrases and sorts these people about that. So you have to prove it, and there’s no better way of proving they’ve been in the market with customers.

Mark Littlewood 

Sorry, yes.

Audience Member 

Hi. Is that working? Yes, it is, right. Hi, how are you doing? Thanks for sharing. Though it’s interesting. It’s a story now, but it can’t have been easy for 19 year old. You going through what you did. My question is around understanding the big companies and obviously the three years haven’t aligned with what you thought you were there to do and what you’d get from it. Can you hazard a guess at what they wanted from you out the three years?

Duane Jackson 

Yeah, and it was very different between what they wanted. So again, big companies struggle with entrepreneurs as much as entrepreneurs struggle with big companies. So they knew what they wanted from me. They fought, but had no clue how to get it out of me. So if you ask the ex co there, or the CEO there, what she wanted from me, she would have said one thing, but then when you speak to the people I’m working with that have had a totally different view, but largely again, with hindsight that was on me working with them, but to try and find how to make that happen, and I didn’t put enough effort into that, I just carried on in the trenches and the trenches, doing what I was doing there. So yeah, I think the real point is big companies struggle with entrepreneurs as much as we struggle. They’re as alien to us as we are to them, which is why a lot of entrepreneurs don’t stay in companies once they’re required. It’s and part of that is, I think what I’m starting to realize, it’s a completely different animal. We say big software company, small software company. We should have different terms. It’s apples and helicopters, right in mind, apples and oranges.

Mark Littlewood 

Yeah, someone over here, I think. I don’t know if I said putting advisor and investor would make you look silly. I know a lot of people that look really silly because they call themselves advisors and investors.

Duane Jackson 

I think it’s a bit boring. It’s what everyone does, something better than that.

Mark Littlewood 

What sort of investing have you done, and has that been? Has that been a great way to lose money, or a great way to.

When do you like giving advice? What sort of where do you? Where do you where do you bring value as an advisor? Value? That value that provides value for you.

Duane Jackson 

And to make money. So for me, I’ve really struggled with the early stage stuff. I really think if you think you’re clever and you think you can spot winners, go and do a whole bunch of early stage investing, you soon realize you ain’t got. I think it’s there’s so many variables that you can’t grasp and what’s coming down the line, whether in the business, whether externally, macro economics, COVID, whatever else that you can’t at an early stage, call the winners. So therefore the only way to succeed at that is to do volume. You have to do lots of them, which I can’t do because I want to know exactly not scatter gun. Apparently, it’s a portfolio portfolio. So which one you need the money to do that? Okay, fine, but you need the appetite to do that. And I like to know these businesses that I’m getting involved in, so that early stage stuff doesn’t work for me. So brief, HR is a good example of a not quite so early stage they existed. They already had revenue. I was very involved with that company, and I understood it in and out, and helped shape where they were going. And that was very successful. And separately to that, I’m part of something called scale up group, where we work with businesses at million plus revenue that want to raise money, and we work with them to make sure, one, you’re in the right shape to raise some money, and number two, to make sure you’re only talking to the right investors, and we’re on your side to get you a good deal, and we co invest. So when we do take you out to a fund, the fund knows you’ve been pre vetted by us, so you’re you’re going to have everything in order. And number two, the fund knows us lot, women, scale up group. They’re all exit entrepreneurs. Mike Tolley city, John O’Connell staff, where people little bit older than me that bon at Randall are all tech, tech entrepreneurs. So that that’s what really well, had some good returns from that, and there’s a few that still out there that they might crumble. But I think so far, I’m up overall on that, and that’s worked really well. But I do worry there’s a bit of herd mentality with that. As we’ve got bigger, we used to look at the business and make a decision, have a decision, have a good conversation, and now I found myself looking and going, Oh, you all okay? Yeah, I’ll put some money in as well. Yeah, I think, yeah, we’re in danger of doing something wrong there. We’ll see we’re conscious of it.

So well, that’s where I struggle, right? Is to get the value for me from it. So there are a few companies that I’ve helped so one being a company’s cap tables all over the place. So we’re really trying to do stuff they’re a bit directionless, and really help them out with some initial advice. And you need to do the issues. And you need to do the issues. And they went off and done it, and then came back, okay, what now? And I’m like, you’ve got a lot of value from me, and I’ve got nothing in return, because maybe I’m not pushy enough in terms of defining it. And also I contradict myself, right? Because if I’m talking to an early stage founder, I’m saying, Hold on to every little bit of equity you can Oh, can I have? Don’t give any advisor, don’t give any advice, don’t give it to anyone. And I’m like, Oh, actually, yeah, no, could I? So I enjoy doing that with early stage businesses, and I get a lot of people email me, and I really enjoy what I’m used is when people ask for general advice. You want general advice. You know, when you buy beans, store them upside down in the cupboard, so when you get them out and take the lid off, they just fall out. That’s my best general advice, right? But if you’ve got specific questions with specific problems, I could be more helpful, but yeah, anyone asks for general advice gets told about baked beans, and I’m still chucking at my keyboard when I’m typing it, and just the expression when they get my reply still tickles me.

Mark Littlewood 

One final question, okay, we’ll get Chris. You’ve got a mic.

Yeah. So thanks very much for sharing your story. My question is more around you mentioned that you had a mentor who was quite instrumental in helping you shape and guide your journey. There’s maybe two nuanced questions to it. The first one is, at what point did you realize you needed the mentor and accepted you needed the mentor. And two, how did you go about actually vetting and selecting your mentor, even reaching out to them? Yeah,

Duane Jackson 

so the few points to that. So I had no clue how to run a business or start a business, right? I had no MBA, no formal training. Didn’t even finish school. So the fact that a mentor would even be useful is not something that would have occurred to me that was all because of the Prince’s Trust having decades of experience of helping people to grow businesses, and that’s the framework that they put you in. So you get a mentor for the first two years. And actually the mentor I got assigned by the prince trust was, okay, not brilliant. It was useful as a sounding board. And actually, if you’ve not ever mentored businesses, it’s a really interesting and useful experience. You get a lot of value from as a mentor, but really a mentor, but really, there was a sounding board, whereas Lord Young, and I think this is the way most good mentor mentee relationships come about. You’re not looking for a mentor, he’s not looking for a mentee, and it just happens naturally, which I know is of no help whatsoever, right? When you’re trying to find a mentor. Oh, it just happened naturally.

There are professional mentors out there. Yeah, there you go. What he said, but yeah, it comes about from finding someone in your industry that you get on with that understands your business or your industry well enough that can give you a bit of advice that becomes a recurring thing, and before you know it, they’re your mentor. So I probably have mentees that I would not think of them as mentees, and they won’t think of them as mentees, and they won’t think of a mentor. But really, you look at relationships, that’s exactly what it is.

Mark Littlewood 

You’re learning from each other.

Duane Jackson 

Yeah, absolutely, and especially in one excuse coming, oh, I’m running a business, I’m too busy, or I’m too early stage, I have nothing to give. Is never true. One, there’s always someone further behind you in the process. Two, to get that and I remember when I was running Kashflow, I used to meet people over at London Bridge and would have what you call mentoring sessions, I guess, with businesses that were a little bit behind me, and that always gave me a fresh perspective on whatever I had gone on back at the office when I had a break from it for an hour, but talk to these people about their problems. Yeah, it really gives you a new perspective on your own. So you do have the time for it. You do have something to give.

Mark Littlewood 

So Lord Young told you not to tell a load of stories to.

Duane Jackson 

Start working out which ones they all were now, yeah.

Mark Littlewood 

And you were, I mean, Lord Young died last year.

Duane Jackson 

He died 20 years to the day after I got out of prison. So night for December 2022.

Mark Littlewood 

And you spoke at his.

Duane Jackson 

Yes, he had a memorial service at Freemasons Hall in London, which is a impressive venue, and there was an impressive lineup of people there, given the histories I had. And what amazed me, so I’d known the guy for 20 plus years by this point, and there are other people that known him for longer, and everyone in that room learned something new about and they didn’t know because people were getting up and telling stories, because he wasn’t one to be boastful for that stuff, but he told me seven times about opening the first box of Apple leases that came into the countryside. Why can’t you tell me the other stories, rather than that same one, seven times?

Mark Littlewood 

Duane tech guy.

Duane Jackson 

But it’s interesting because he was in David Cameron’s office. It was an enterprise advisor in the 2010 cabinet. So David Cameron was on stage just before me and talking about. Back in 2010 only two people had a private office in number 10, one being David Cameron himself as prime minister, and the other being Lord Young. And everyone else was in sort of communal or hot desk spaces. But apparently the Rex cons in and out of Lord Young’s office, he said, with a look on his face. So I was, I quickly changed the beginning of my talk which fight with I was that ex con. So it’s a good, really good segue to my part.

Mark Littlewood 

Just call me Dave.

Duane Jackson 

Yeah, but, but yeah, he did blush.

Mark Littlewood 

Excellent. No, you had a very and I know.

Duane Jackson 

He’s a very important figure for me, because he backed me, believed in me, gave me a lot of advice along the way, incredibly support. So early on, I had the opportunity to sell the business for 2 million quid, very early days, and I was up for that. And he said, Well, why do you want to sell that? Because I’m going to make over a million pounds. And he said, right? But if you realize, if you Cameron, grown business, if it’s worth that today, and I agree it is worth it will be worth a lot more in the future. So look, here’s an option, right? If you want to sell it, sell it, and I’ll do whatever I need to do in my shares, I’ll either sell them as well. I’ll stay whatever they want me to do to make this deal happen for you. Here’s an alternative. I’ll lend you 100 grand. You pay me back when we sell the business. If we sell the business, if we ever sell it, interest free. Because yes, please. So took the 100k that helped pay off all the credit card debt I had and whatever else, and made me a bit more comfortable at home. Yeah, and seven, eight years later, when we eventually sold the business, he said, Of course, I don’t want that repaid, because he had done very well. But yeah, it’s just little things like that along the way that it’s incredible having that kind of person in your life, definitely, especially given the way I grew up, right? I mean, he was a father figure for me. I didn’t have anyone else around like that, no? So, yeah, very much.

Mark Littlewood 

Duane, it’s always a pleasure. Thank you and a privilege. Thank you. Thank you.

Duane Jackson

Founder, KashFlow & Staffology

Duane is an entrepreneur with a bio that includes the words, ‘which culminated in my arrest at Atlanta Airport with 6,500 ecstacy tablets‘, He became an entrepreneur after the subsequent, almost inevitable, prison sentence because he was left with no alternative given the ‘large black hole in my CV’. 

He set up a web design business with the help of a grant from The Prince’s Trust a UK based organisation to help give people a second chance. His realisation that accounting programmes sucked was the inspiration for KashFlow, a SaaS based simple web accounting package for small business. He sold KashFlow in 2013 and has subsequently created and sold two more SaaS companies, most recently Staffology.

If you’re interested in the early story and how he applied his marketing brilliance to growing KashFlow, you should watch this conversation from BoS Europe 2015.

You should also read his book, Four Thousand Days: My Journey From Prison To Business Success.

More from Duane.

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