Duane Jackson: Pride of Britain – His Story

Duane grew up in childrens’ homes in the East End of London, left school with no qualifications and ended up serving a 5 year prison sentence for drug trafficking. He served time in US and UK prisons.

On his release, with a baby on the way, he decided to “go straight”.  He struggled to use products like Sage and Quickbooks to keep accounts so developed a web-based application for his own use. He eventually spotted the opportunity to sell this product to other small businesses and KashFlow was born.

KashFlow was one of the first Software-as-a-service (SaaS) products and was at the forefront of the move of software from he desktop to the Cloud.

By 2013 KashFlow employed 40 people and was serving nearly 20,000 customers. In October 2013 the business was sold to IRIS for an undisclosed sum that has been reported as being “in the tens of millions”.

His extraordinary story is recapped in his recently released book Four Thousand Days and seen him be honoured in events such as the Pride of Britain Awards in October 2015.


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Mark Littlewood: So in your bag, you’ll find this book. And this is a bit of Duane’s story. And it’s a real ripper. You wrote this beginning of the year?

Duane Jackson: Been a process over the last eighteen months or so.

Mark Littlewood: Okay. I read this, and I read it because I wanted to pick up on some of the things that, Duane has been doing over the years that have been about marketing… and how you start, this very very teeny little company. And stay in control over your business and do good things. And it’s a little disappointing, if I’m honest, cause it’s not enough of that. So I think that’s volume two. But Duane’s got the single worst CV of anyone I’ve ever met. [Laughter]

Do you want to give us a rundown?

Duane Jackson: I suppose so.

So, if I start with education, that would be a blank section on the CV. [Laughter]

So I left school at fifteen. Got kicked out of two schools at fifteen. Prior to that, I’d grown up in children’s homes in the East End of London. And then followed, what’s unfortunately a typical route for kids that grow up in care. I was getting involved with criminality. So, often when I tell my story, I get asked how I fell into crime. And I didn’t fall into it, I grew up around it. Fact in my early teens, I was the exception, because I wasn’t involved with anything too dodgy. Ah, little bit, but not too dodgy. [Laughter] So, but then it did get quite dodgy, cause…

“by the time I was 19, nearly 20, I was arrested in Atlanta airport, in Georgia, with six and a half thousand ecstasy tablets in my hand luggage. That didn’t go down too well.”

Mark Littlewood: Okay. Let’s just think about this. [Laughter]

So, I was trying to imagine what six and a half thousand ecstasy tablets look like in your hand luggage. Who came here, flew with hand luggage? Hands up… Six and a half thousand ecstasy tablets. I thought okay, I can do this with tic tacs, [Laughter]

…and there are forty tic tacs in a box of tic tacs, and it would have cost me about two hundred quid to buy the tic tacs, to then empty out into a bowl, and then kind of go, there you are. Or, it’s about two packets each, for everybody in this room, and imagine sticking that in hand luggage.

Duane Jackson: Ryan Air would charge excess baggage definitely. [Laughter]

“Don’t do drug trafficking with Ryan Air, it will eat into your margins, definitely.”


Mark Littlewood: What on earth possessed you?

Duane Jackson: What possessed me? A lack of thought really, and not thinking about it too much. [Laughter] So, I’d grown up around it and it’s easy for me to tell the story of growing up in care and getting involved with drugs, and coming out and starting a business that’s a success. But I always miss a little bit, cause it doesn’t fit into a narrative, which is, when I was kicked out of school at fifteen, I actually taught myself to program.

There was a ZX Spectrum at the school. Between nine and three, I was meant to be in education, um, but they’re social workers right? They’re not teachers, so they didn’t care what I did, as long as I wasn’t watching TV. So I picked up this spectrum and taught my self to program. And when I was sixteen, seventeen, I ended up being an IT contractor. Making pretty decent money for a sixteen, seventeen year old. I met a girl in New York, so I actually knew her online from a thing called interface pirate radio, online radio station in the late nineties. Ended up out in New York. And I could afford to pay to go out there and see her. On one of the trips, my best mate, Allen, said actually I’m gonna be out there. I was like, you haven’t even got a job mate, how are you managing to fly out there? [Laughter] He said “Oh, don’t worry about it, I’ll see you out there.” And when I got there, I went and met him as his hotel room.

So I’d gone out legitimately to see Simone, my then girlfriend. I went and met him at his hotel room, and he has all these drugs all over, so okay, [Laughter] so that’s how you’re funding it. But I didn’t think much of it, because I was around all that stuff anyway. I just wasn’t involved. And then I got greedy essentially, so I lost my contract. I was on forty pounds an hour, and I was waiting for the next contract to come in, and I was offered one at thirty, and I thought, I’m worth forty pounds an hour, hold out for that. Yeah, and got to the point where I was running out of money, I couldn’t pay my rent, I had a girlfriend in New York who I’d not been able to go and see, and obviously this was an easy way to get me trip paid to New York, and make some money on the process. And it’s only ecstasy, it’s not like it’s a class A drug, right? Actually it is, but I didn’t realize that. [Laughter] I thought, it’s not heroin or coke. In the eyes of the law, it’s exactly the same. Yeah, I’d just been completely stupid really.

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Mark Littlewood: So, what happened, I mean what’s the short version from Atlanta to getting out on the streets again? Cause when I say the short version, it’s covered in this, and I can’t recommend this strongly enough.

Duane Jackson: It’s the more fun part of the book, what happened in Atlanta, and, so…

Mark Littlewood: It’s a… yeah, it’s a page turner.

Duane Jackson: Even if you just read the first chapter, so that on its own, that’s probably the best bit to be honest, [Laughter] dump all the rest of it. But the first chapter, I won’t tell you too much, basically it was, I worked with the D.E.A. and we supposedly tried to deliver these drugs to the recipients and it didn’t all work out as planned. Lots of guns involved. But from there, then it went to prison in the states, I was in prison for bout six weeks over there, before I managed to get back the UK, so somebody that I’d used to work with put up bail for me to come and work with him in the UK, with the understanding that I then go back and stand trial a year later. Um, whilst I was on bail, um, the whole gang I was involved with on the East End, they all got arrested as well, and the police ended up getting the D.E.A. to do an administrative dismissal of the charges, so I could be tried in the UK. So, I was tried in the UK and sentenced to five years. And served two and a half years in prison here.

Mark Littlewood: Did you feel lucky?

Duane Jackson: Yeah, very much so. So, you’ve got to remember, when I was arrested in the states, I was looking at twenty five years, easily. It’s the bible belt, they take this stuff pretty seriously there. Even when I got back to the UK, I felt lucky cause, well firstly getting out of the US prison system took a year about, that was expected. [Laughter]

Mark Littlewood: I’ve been through US Customs. [Laughter]

Mark Littlewood: Doing it with all that extra hand luggage is not as much fun. [Laughter] So I was brought back to the UK, then I was told by my barrister here, to expect 12 years. So, when I was sentenced and got five, and the other guys got six, eight, four, we were all over the moon. Hugging each other and everything, because these sentences were half of what we expected. So, yeah, really lucky. And also, lucky that I got caught, ended up where I am now, cause I wouldn’t be where I am now if I hadn’t got caught. I’d have got more involved with it. I’d have… I don’t know, I’d probably got shot, or a much longer prison sentence, who knows.

Mark Littlewood: So, a long term by any stretch of the imagination. What happened when you got out?

Duane Jackson: So, I mentioned a guy who had bailed me out of prison from the states. The condition was that I work for a year, and he’d pay me a reasonable salary, until I had to inevitably go to prison. And what happened during that year I was on bail, I worked for him, but the business he said wasn’t making enough money to pay me, so in lieu of that, he gave me twenty percent of the company. So I had something to look forward to when I got out. The problem with prison sentences is, one of the many problems with prison sentences [Laughter] if you’ve got a legal document and you end up at an open prison like Ford, it’s full of ex-solicitors and people who really know their stuff. So, someone there looked at it for me, and essentially it was an option that was worth nothing cause of how it was written. So, I spoke to Ben and said look, when I get out I’m going to be coming to work for you, and my understanding was that I own twenty percent of the company, but now I’m being told I don’t, and it’s not worth the paper it’s written on. And he admitted, well, yeah, that is true, but the solicitors made me do it, but I’ll get it changed. And he kept saying he was going to get it changed, and I kept pushing for it. And my release date’s getting closer and closer, and it just wasn’t happening. And then the Prices trust came and visited Ford’s prison, and spoke about what they do, and helping ex-offenders, ex care leavers, people with no qualifications. So, tick, tick, tick, um, [Laughter] help them to start a business. And I thought, you know what, I’m gonna go down that route. So that’s what I did when I got out. I got help from the princess trust, to start as a one man web developer.

Mark Littlewood: Fantastic. And this, it’s not the start of your entrepreneurial journey, cause—

Duane Jackson: It started a bit earlier. [Laughter]

Mark Littlewood: It started a bit earlier, yeah. I’ll come back to that in a minute. Um, So you’re gonna be a web developer, but you ended up at a web development company.

Duane Jackson: Yeah, so this was 2003, and being a web developer was working alright. I was okay from it. I wasn’t making lots of money, but enough to pay the rent, but one of the problems I had was with the accounting side of things. So, I looked at Sage, Quick Books, and they were just crap. So, as, most people here that are techies, you probably pride yourself, you can pick up any product, get your head around it really quickly, and I could with any software solution. With Sage and Quick Books, I just couldn’t. I had to go and read the manuals, and men don’t like reading manuals, as we know.

Mark Littlewood: So they come with manuals? [Laughter]

Duane Jackson: Apparently, yeah. What, men? Or accounting software? [Laughter] So the accounting software was just crap. So, I quickly threw something together for me to use, because using word and a spread sheet is okay for a bit, until you end up with two invoices, with the same numbers, same amount, different customers, one’s paid, one’s not. You get in a real mess. So I just threw something together with an access database and some VB scripts, and put it online. Because that was a quickest way for me to program something, rather than do it from the desktop. And I carried on being a web developer. Spoke to other princess trust businesses, was around a lot of them at the time, saying what are you guys using for your accounting? Cause I wanted them to tell me about a great product that I could use. Everyone had given up and gone back to Word and Excel. Said I’ve written this thing, can have a copy of that if you want. So, there literally was a copy and paste of the folder on the server. And I don’t know why it took me so damn long to realize the opportunity that was there. [Laughter] Hang on, I should be charging people for this, rather than selling my time by the hour. Eventually I did realize, and re-engineered it to be, what we’d call a multi-tenant platform and sequence server–

Mark Littlewood: Oh, multi-tenant platform, eh?

Duane Jackson: Oh, yes. We should be playing buzz word bingo here today, shouldn’t we?

Mark Littlewood: Yeah, pro-actively, leveraging, strategic, opportunities, in the European B2B space. Laughter]

Duane Jackson: Can you do that again?

Mark Littlewood: Yeah, easily. [Laughter] People send me press releases. Um, so [Laughter] so there ladies and gentlemen is how you turn from a service business into a product business. [Laughter] Which is one of those things that service businesses really, um, struggle with. But it’s still small.

Duane Jackson: Yeah.

Mark Littlewood: For some reason this sort of reminds me of Derek Sivers. I don’t know if people were around, uh, or if people were listening last year about Derek Sivers and CD Baby. He was a musician who could code, and wanted to sell his cds online, and then so, he put his cds online and it cost him twenty five grand to put up a payment gateway, but he did it, for… to prove that he could, and then friends of his started to kind of come along, and all of a sudden he had CD Baby. So, similar sort of origin, but when did you think, yeah. Did you… Well, first people that were using it, did you give it away?

Duane Jackson: Well, yeah. Exactly. So, you got to bear in mind, this wasn’t an accountant’s product early on. It was a two or three page web application. Where you could create an invoice, it’d give you a sequential number, you can put in the amount, not multiply allowance, just the amount, and then paid or not paid. Not part payments. It’s either paid, not paid. It’s really, really simple. And I don’t think I could charge for that really. So I gave it to, I think a group of about twenty princess trust businesses, on the condition that they’d give me feed back on what I’d add to it, for them to carry on using it. Um, and the truth is, from there, all the way through to exit, there was no massive leap in what we did with the product. There was no massive leap in terms of the number of customers. If you were to plot how useful the product was, how useful, uh, how much revenue we got, our customer growth, it’s pretty much just a smooth ride. But the process was, listen to customers, what do you need, adding it, and going back to them, and asking again. But the beauty of it was the whole sass model. Was the… and being a programmer myself, so you as a customer could ask… in fact, you are a customer, aren’t you?

Mark Littlewood: I’m a paying customer, yes.

Duane Jackson: Good. So you as a customer back then, not now,

Mark Littlewood: Not free.

Duane Jackson: You never got it free back then?

Mark Littlewood: No.

Duane Jackson: Sorry bout that. [Laughter] Moving swiftly on. Um, as a customer, you could ask me on a —

Mark Littlewood: Too late for a refund now isn’t it? [Laughter]

Duane Jackson: It is, yeah. Speak to them, I don’t own it anymore. But you could ask me on Thursday night for a feature, I could spend Thursday evening programming it, Friday morning you get told, here it is. And not only are you really happy, you go and tell your mates about this amazing product, and this amazing guy that’s doing all this work for you. But it really helps to spread word of mouth. And I think the other key thing is a well, with SaaS products, versus desktop, Sage, whatever, is now typical what we did back then, was to include support with your monthly subscription. Therefore, we’re incentivize to make the software really easy to use, so that you guys aren’t contacting the support, which is a cost to us. If you then look at something like Sage, I shouldn’t keep saying Sage, they’re not the enemy anymore. If you look at desktop products, that where they charge you for a support contract, they’re incentivize to keep the product really difficult, so you phone up, pay them an extra ninety nine quid a year. So, that’s why I think you see a lot of the sass products a lot easier to use than desktop products.

Mark Littlewood: That’s very interesting. We’ll come back to Sage, but… no actually, let’s go into Sage. I was, cause this was built as a fire side chat, and one of the things you did when you were kind of getting a bit of, um, publicity, and doing a bit of kind of P.R. around what you were doing, and getting people to take notice, was take on Sage. Who were what? Two billion pounds, UK, public company. That’s stupid wasn’t it.

Duane Jackson: Not at all. It was the best thing we ever did. [Laughter] So, if you’re, if you’re–

Mark Littlewood ” I’ll set em up mate. [Laughter]

Duane Jackson: I’ll come in. If you’re–

Mark Littlewood: That was an easy one. [Laughter]

Duane Jackson: I want to be able to set em up, but I’m not gonna spot em in for you. [Laughter] So you might have to kick me when you set them up. Yeah, if you’re in an industry where you’ve got a big company in your space that isn’t, I won’t say, isn’t particularly well liked, but isn’t well loved necessarily, and if you can climb on their back and wave a flag, it really helps you get noticed. No one cared about a small little start up, but the media and analysts cared about Sage, cause they’re a public company. And with this whole technology shift, and Sage not doing anything Sass, and analysts saying what’s this Sass stuff, you could get out there and sort of position yourself as, well, analysts come and talk to me, and I’ll explain what Sass is, with our little spin on it, and get in our little digs at Sage. But–

Mark Littlewood: Quite big digs.

Duane Jackson: Yeah, I suppose… Is burning their software–

Mark Littlewood: Burning their software, I was going to have a little pile of Sage software here to burn–

Duane Jackson: And a box of matches. We stopped short of putting a rocket launcher outside their office. We were going to. [Laughter] So, someone I knew up in Newcastle, Ling Valentine. LingsCars.com. If you’ve not seen LingsCars.com, go and have a look. [Laughter] It’s amazing. She’s got a Russian tank, and a rocket launcher, and we were gonna drape it in the Cash Flow logo and go and point it outside Sage HQ. [Laughter] But my chairman said no it’s a step too far. [Laughter] Thankfully.

Mark Littlewood: Where do you draw the line. So, how did that… so you had a battle with a massive company.

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Duane Jackson: They started it. It was their fault anyway. They bloody started it. [Laughter] So, I went along to the business start up exhibition, um, in London. An annual event. Lots of software business companies are there, and Sage are there as usual. And I notice in the corner, this laptop running something in a web browser with the Sage logo. So, I’ve gone over, hid my name badge, said, what’s this. And they start something about this Sass product that they’re bringing to market in the next couple of weeks, and this is its first hour in. I said, oh, who’s your main competitor for this? Oh, there’s this company called, Cash Flow. Said, oh, tell me more. [Laughter] So, they were telling me about how Cash Flow were causing them problems, and therefore had to build this solution, and it’s going to be released soon. So I said, okay, I can actually tell you who I am now [Laughter] This buzz went around the Sage stand. It’s the Cash Flow guy. [Laughter] But I said to the guy who was demoing the software, I said, I’ve not seen any PR about this. Said, no, we’re not doing anything yet. I said, well, I’m gonna write about it as soon as I get home. And he was actually really pleased that I was going to [Laughter] because his marketing team hadn’t worked really had on this product, so I said I’d write about it. [Laughter] Which, of course meant, if anyone searched for the product in the future, guess who was the number one hit on Google. [Laughter] Um, but he also made a strange comment to me. Said we’re not meant to talk to you cause of these legal problems. I said, what legal problems? I don’t know. We were told we’re not allowed to talk to the guy at Cash Flow cause of legal problems. And I forgot about it. So, I get home, I write the Sage live as it was called, blog post, and the whole industry, which was like that big, it’s really an echo chamber. It was all abuzz about it , and loads of traffic was starting to raise our profile. The following day I get a letter from Trade & Standards. So what had happened, Sage had asked us to change five things in our website, cause they thought they were unfair. And, okay, three of them were, I was taken a piss a bit, [Laughter] so I changed them. The other two, I thought, well, no, that’s a fair comparison, I’m gonna keep it. And they asked me again, I said I’m not changing it. And essentially, they reported us to Trade & Standards. So, then I realized what they meant about the legal problems. So, when I started poking around their product, I noticed it has some serious security issues. So, I know there are a few techies in the room. But part passwords didn’t get request, and all sorts of silly stuff. So, it was just absolutely ridiculous. And I know what you’re meant to do in that scenario is to let the company know, give them a chance to fix it, but you go and scream publicly. But I thought–

Mark Littlewood: But you weren’t allowed to talk to them. Legal issues. They told you.

Duane Jackson: Well, their legal issues. So, they weren’t suing us. They had no customers on this yet, cause it was in beta. And also, there was a PR opportunity, so [Laughter] all things considered. I blogged about these security issues that I found on there, and at some point when I was poking around, I got into some internal pages I shouldn’t have seen. And I had a real air of drama to the blog for the non techies, and said, at this point, I thought I better log out the software, because I thought the FBI would be knocking on my door any minute now. [Laughter] Fact we were in the UK, but it was a nice bit of drama. And Sage of course denied they had any problems, but, and they were using some Oracle software that doesn’t exist anymore, so these were problems they couldn’t even fix. So, I’m going round to the media saying, Sage can either, um, admit I was right and withdraw the software, or say they don’t care about customer data, and carry on with the product. So, really caught between a rock and a hard place. And of course by the time they decided to do anything about it, which was to admit we were right and withdraw the software, we’d moved on to another angle of attack. Which I think was setting fire to the software [Laughter] was the next move.

Mark Littlewood: You were gonna get involved in a SaaS marketing workshop. I have to say, there are so many other things. You did a guest blog post for us six months ago, which were your thirty one lessons that you learned in building Cash Flow, and I’d strongly recommend that. But also, a bunch of your other blogs. One of which, was picked up by the FT and Telegraph. Which was why drug dealers–

Duane Jackson: Yeah.

Mark Littlewood: Are great at business.

Duane Jackson: And picked up by the department of justice as well. [Laughter] That was interesting. Um, yeah. If I go back to how I… So, I said that I wasn’t doing anything too dodgy, we might have different scales of what’s too dodgy, but when I was sixteen, I was selling weed to my friends, which was not too dodgy, but that’s the starting point for most people to get into bigger drug dealing. But if you look at how and why people like that would start selling weed to their friends, it’s because they’re all going out and seeing the local drug dealer buying, and paying fifteen quid for an eighth of weed. And someone else will go, hang on a minute, I can buy half an ounce, and sell it to all me friends, and I can get mine for free. If that’s not entrepreneurial, I don’t know what is. [Laughter]

So, even when we’re doing the drug trafficking we had couriers that were taking ecstasy from the UK to the US, but they were coming back with nothing. We were all getting to bring coke back. And today that’s just called sweating the assets.[Laughter] So there was lots and lots of peril. Drug crime, see I think there’s a real wasted opportunity. There’s a lot of people in prison in this country, that if they use their powers for good, instead of evil, would actually be very positive, positively contributing citizens. I’m sure you’ve got a much better phrase I could use.

Mark Littlewood: No, I haven’t. Um, I think that’s actually the expression… remember a few years ago we had dinner with Ken Clark. Where you sat next to him.

Duane Jackson: Of course, you were actually at that dinner.

Mark Littlewood: Yes. And you sat next to Ken Clark. And it was just like… it ws a very kind of moving moment. Yeah, you got to kind of hump with him [Laughter]

Duane Jackson: Well, because of this blog post on when I was in prison, the M.O.J. got in touch, and they said we want to do something about this, so I arranged a lunch with people like yourself, people that are really busy, but are passionate about start ups, entrepreneurial, and doing good for society. So we managed to get some, other than you, we got some good people there as well. [Laughter]

Mark Littlewood: Yea. No, no no. It was a last minute call. [Laughter]

Duane Jackson: Yeah, you were just filling a seat. It was a good group of people who had given up their evening, and then the Sped, the special adviser to Ken Clark, just opens the conversations. And I’m sitting there thinking, this guy’s brought the wrong notebook, what’s he talking about? Cause he’s talking about using prisoners as employees in your business as cheap labor.

Mark Littlewood: That’s the American way actually. One percent of the population

Duane Jackson: We do it over here as well to a degree. Not necessarily as bad as it’s done over there. Actually, I think that’s something that can be positive if done right, but that a separate thing. But the M.O.J hijacked that dinner, and tried to change it for that. And I just got pissed off with trying to deal with government stuff. Working with charities can be hard enough sometimes, but you know their heart’s in the right place. Um, but yeah, working with government is another thing all together.

Mark Littlewood: Yes. But you’re still involved in Princess Trust and mentoring, and all that sort of stuff. Let’s fast forward to eighteen months ago? You had lots of people chasing after you. To invest and… you were doing really well and kind of growing. You kept pretty much very good control of the business, but what’s happened in that time? What was your kind of thought process in there, cause you sold Cash Flow a year ago?

Duane Jackson: October 21st, eighteen months ago.

Mark Littlewood: Okay. Cool.

Duane Jackson: So, we’d never really taken any significant investment. I had Lord John who mentored me very early on by the Princess trust that became a share man– Share man? That’s a new word. [Laughter] shareholder and chairman. It’s the share man. I like that. [Laughter] So he was the chairman, the shareholder, and also importantly, a mentor. But also, he was there, although he didn’t put any significant money into the business, he was there as a sort of financial safety net if you like. So I took a lot of risks with the business, I wouldn’t have took, if he wasn’t there ready to write a check to cover any losses if need be. So I managed to maintain a majority of the company. And we’d have companies that were interested in buying us. And in fact, two years before we were sold, a Dutch company tried to buy us, and we’d gotten to a point where we were about to sign a silent purchase agreement.

One of the things Lord John told me, was don’t put yourself on the yacht.

But what he means is, if someone comes, cause he used to buy a lot of companies, he helped built great universal stores. And they used to buy a lot of companies. They’d go and offer you thirty million, do due diligence, and say actually, only twenty million. By then you’d already put yourself on the yacht. You’d already bought this, and you had the house, the wife, and this, that, and the other. Your partner is also looking at other ways to spend the money. So, when they then knock forty percent off the price, you take it. So, because I had that advice ringing in my ears, the Dutch company did reduce the price at the last minute, and I told em to do one. I don’t know where I got the balls from at the time. My wife wasn’t very happy, but we soldiered on for another eighteen months, and got into a position where I was really happy with the business. I’d struggled to build a good team around me. At that point I’d done that. We’d put a lot of effort into getting the business moving in the right direction, structured well, when an offer had come along. And, so two things. First, I’d long been through the offer from the Dutch firm, also, when the Dutch deal fell apart, Lord John introduced me to a friend of his that bought some equity from me personally. So I had a million pound personally that I’d taken out of the company already. And I think that was a huge, that made a massive difference in the end to my other shareholders in terms of the value they got. Cause I had that money there, when someone then comes and waves a check in front of your face, you’re not grabbing it. It can actually feel quite comfortable already, so I’ll look at your offer on its merits, rather then, I could do with a few quid. Um, so we got offered one price, and I can’t remember how much of the numbers went into the book, cause the final number I’m not allowed to confirm or deny any rumors. It’s around twenty million quid. I’m not allowed to. [Laughter] But the initial offer, I just turned it down straight away, and It was more than what I was offered by the dutch guys not too long ago. And they came back and upped it even more. And, again, can we have a bit that doesn’t get broadcast?

Mark Littlewood: Sure.

Duane Jackson: [Laughter] Good. If you’re deleting stuff.[Laughter],[Cheering]

Mark Littlewood: So, what are you doing now?

Duane Jackson: Looking for a purpose.[Laughter]

Mark Littlewood: Looking for a purpose. Now its been eighteen months, and when I exited, people said, what are you doing next? I said, I’ll start something else. I’m not sure what. And to me it was a given. It would be Sass, and it would be B to B. And as time has gone on, I’ve gotten less and less sure. I’m not sure what I’m gonna do. But I’ll fine something–

Mark Littlewood: taken up web apps–

Duane Jackson: Yeah, I’ve gone back to IoS now, so I got away from the technical stuff when Cash Flow was growing. And still Cash Flow is run largely on VB script classic KSP stuff. So, that was out of date even when I started using it fifteen years old. So, yeah, I’m trying to bring my skills up to date. Not necessarily so I can write the next killer app, but I think one of the advantages for a technical CEO, is you can have good discussions with your team. You have a good understanding of what is possible, and what isn’t. So, I want to make sure that whatever I do, do next, I’m not talking about VB script and ASP. That’s why I want to know about node, and swift, and whatever else.

Mark Littlewood: Cool. Um, you started this discussion, and we’re gonna wrap it up now, um, with a kind of education blank. You are one of the most educated people I know. You just don’t have a formal education. And I think one of the reasons that you inspire me and other people, is—

Duane Jackson: Don’t’ embarrass me now.[Laughter]

Mark Littlewood: I’m gonna make you cry.

Duane Jackson: Um, that was the other thing. Sorry I forgot to tell you that. [Laughter] [Cheering]

Mark Littlewood: Stick you hand up if you’ve got a question. There.

sp3: How do you say do one in Dutch?

Duane Jackson: In dutch, oh.

sp3: Yeah, you told us do one.

Duane Jackson: Oh, do one. [Laughter] Um, it’s verbally. I’d have to see. Cause I’d agreed with their CEO that they would not budge on price. Um, yeah, and their CFO, actually no, it was their general consul. It was a guy that nobody says no to. You got this feeling in the due diligence process. I think I’d just used the phrase, you can sod off. And it translated I think. They understood it.

Mark Littlewood: The beauty of the Dutch. [Laughter] They speak better English than us.

Duane Jackson: I really like dealing with the Dutch. Cause they’re really direct, and straight, and to the point. Actually I find it kind of refreshing.

Mark Littlewood: Gus.

sp4: Two quick questions. Um, can you travel to the US yet?

Duane Jackson: I can now. Yeah.

sp4: Very good. Can you tell me a bit more about your relationship with chairman. How he came on board and how that played into your development into the company and stuff?

Duane Jackson: Mark says to tell you to read the book. There’s more detail in the book, especially about the relationship and how it grew over the years, but initially he met me at an event. I showed him what I was working on. It was very very early days. Um, and he said before he left, if you ever need investment, let me know. Um, and I think a bit of persistence on my part , and some steps I had to take to make it more attractive for him. Which, again, is in there. Initially I wanted him to be my chairman. I wasn’t that fussed about getting money, and those two things I wanted. One was some advice and some support, but also some credibility as well. Because we’re selling accounting software, and we’re starting to sell to accountants, being an ex-con isn’t a good place to start. [Laughter] And early on that wasn’t out there, but I think it was inevitably it was gonna come out at some point. And so, having a lord on the board would be a great way to do that. So I asked him to be my chairman, but he declined. He became a shareholder and mentor, and later I made him become the chairman, as is in the book. [Laughter] But yeah, it was a… I find it hard when people look at the relationship I’ve had with Lord John over the years, I find it hard to give people advice on how to get that kind of angel, because he’s been absolutely amazing. But I think it’s because he’s a unique individual. I don’t think I can give anyone advice on how to find a lord John. And the things he’s done to help me over the years is… um, I mean it’s all in there. It’s above and beyond.

Mark Littlewood: Fabulous. One final one?

sp5: Do we do enough to rehabilitate people in this country? Is there more that could be done?

Duane Jackson: [Laughter] Yeah, there’s a lot more we can do. I could scream and shout about it for a while, but there’s a few things. Rehabilitation offenders act and stuff like that. If you serve a sentence over a certain period of time, you’ve got to declare it for the rest of your life. So, now we’ll sheepishly spend some of the money on expensive art or whatever else we’ve got in the house, I’m paying a fortune to insure it, cause I will have to declare my conviction for the rest of my life. So, there’s things they could change, so people aren’t as hindered when they get out of prison, and there’s certainly a lot more they can put in place. And I think, also, not just from prison, but from the care system. I think forty percent of guys who are in prison, have also been in the care system. So, I actually think they can get to them earlier, before they get to prison. There’s a lot that can be done.

Mark Littlewood: Well, we’re gonna take a break. You’re around for the rest of the event, so, if you’ve got something you think is gonna give Duane some purpose, and some meaning, [Laughter] this is a good time—

Duane Jackson: I’m not writing any angel investment checks. [Laughter] That’s what I found. All these people get in touch, saying with your experience, it’s be great to have you involved.

Mark Littlewood: As an investor.

Duane Jackson: I mean, with your check book, it’d be great to have you involed, is what they really mean. Don’t want to do that.

Mark Littlewood: Um, so you’ll be around for the discussion workshops afterwards as well. And that’s sort of Sass marketing thing that come with your ideas here. Um, but, I just want to say, Duane, thank you so much. It’s a pleasure, and I learn so much from you everytime we talk. And I–

Duane Jackson: It’s because you don’t know much.

Mark Littlewood: It’s because I know jack shit in the first place.[Laughter]

Duane Jackson: You start from such a low point.

Mark Littlewood: Yes, it’s true. Um, but you inspire people, and I know people at every kind of level of achievement or any kind of position in the kind of software world, in the entrepreneurial world, have taken a great deal from what you’ve done. So, keep going and find some people to mentor. Don’t ask him for money. He spent it all anyway.

Duane Jackson: Exactly.

Mark Littlewood: And let’s say, thank you very much indeed.[Clapping]

Duane Jackson
Duane Jackson

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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