Jason Connolly: Thank you so much for joining me today on this podcast, it’s so delightful to have you with us.

Iain Dale: Absolute pleasure.

Jason Connolly: One of the first questions I had for you and I think you’ve mentioned it before on the radio is about career success, what does career success look like or mean to you, Iain, because you’ve been highly successful?

Iain Dale: It’s really weird because when you put it that way, I don’t really think about whether I’ve been successful or not because everyone has failures in their lives, I’ve had some, and I suppose if you look at what I do now, people think, ‘Well, yes, he’s successful at what he does.’ When I left university, there were 2 things I wanted to do. I wanted to be a member of parliament or I wanted to be a radio presenter and I’ve achieved the latter but not the former. I did fight an election, I tried to do it but the electorate fought back and so I never made it. I was going to say I regret it. I don’t really have many regrets in my life, I would have liked to have done it but sometimes things happen for the best and if I had been an MP I wouldn’t have had the last 10 years and it’s the best job I’ve ever had. I also very rarely look to the future. I don’t think, ‘Right, I’m doing this now. In 5 years time I want to be doing X, Y, or Z.’ I don’t really think like that. I’ve had to constantly reinvent myself over my working career and when things go wrong, you pick yourself up, you dust yourself off and you try for something new and luckily, each time I’ve done that it’s worked out. I have, in my business life, been sacked from a company that I helped form, so that was a pretty shattering experience but you recover from it in the end, even though at the time it feels like a devastating blow.

Jason Connolly: When you said that you had to reinvent yourself, in what way do you mean? Is that to move with the times, or working in media, or working in publishing?

Iain Dale: Well, I think when one job comes to an end, my 2 first jobs effectively had a limited time span. The first one I worked for a Conservative MP in the House of Commons after I left university and that’s never a job that you’re going to stay in very long. This was in the 1980s, I was paid £6,000 a year, can you believe.

Jason Connolly: That was Patrick Thompson.

Iain Dale: That was Patrick Thompson but even in those days, £6,000 was a pretty poor salary to live on if you were living and working in London. So, that was in 1985 that I started that and I knew that once the general election was over, that was when I should go, so I did. I had nothing to go to but I applied for a job with the ports industry as a lobbyist trying to lobby the Thatcher government to get rid of a piece of employment legislation called the Dock Labour Scheme and I knew that once that was successful, though I didn’t know if it would be at the time, that would be the end of that job. On each of those occasions, I had to reinvent myself and when I got sacked from the Waterfront Partnership which was a transport consultancy and a conference organising company, I had a big falling out with a guy that I went into business with, I literally was out of a job, had not go a clue what I would do next so I started my own business, a political book shop and then 7 years after that it became clear that the market conditions for bookshops were getting worse with Amazon just starting, the congestion charge came in and I thought, ‘I can’t renew the lease here,’ so again I had to take that online but it was never quite the same and that was about the time I started to try to stand for parliament.

So, every 5 years or so, I’ve had to think, ‘Okay, well I need to do something different now.’ Luckily, on each occasion I’ve found something which I’ve enjoyed doing. Virtually every job I’ve ever had I’ve enjoyed. I don’t regard what I have now as a job because it’s a slightly portfolio career but you take the opportunities that come, sometimes you have to make your own opportunities as well.

Jason Connolly: Do you think these knock backs that you’ve had throughout your career have been quite defining to you moving onto the next thing and strengthen you?

Iain Dale: They do strengthen you. In the end, you regard these things as threats or opportunities and it’s so easy, particularly when you’ve been sacked from something and I can go into the reasons for that if you want but it was basically that my business partner’s wife came into the company and she basically wanted to try to get rid of everybody that worked for me and I resisted that but in the end, who is he going to choose, his wife or his business partner? It was a really traumatic period but you either let it overwhelm you and you think your working life has come to an end or you think, ‘Okay, well it’s happened, there’s nothing I can do about it,’ you pick yourself up and you start again. When I lost the election in 2005, I’ve actually only stood for 1 election, you said it was 3. When I was at university I was a paper candidate in 1 or 2 council seats but in a parliamentary election I’ve actually only stood once. I tried to stand in 2010 but didn’t get selected. When I lost in 2005, I knew I was going to lose in the last few months so that didn’t come as a surprise but in the end I thought, ‘What do I do now?’ Then there was a Tory leadership contest and my friend David Davis was going to stand so I rang him up and I said, ‘Do you fancy a new chief of staff,’ and he said, ‘Yes, come on board,’ so I did that for 6 months but of course he didn’t win that. Everyone had expected that he would and in that case I would have then no doubt continued to work for him, if he became prime minister I would have gone into Downing Street and so on, but he didn’t. So, 6 months later, another point where I thought, ‘What do I do,’ and I actually took 6 months off to think about what I wanted to do and in the end started up an internet television station which was 10 years ahead of its time. That lasted a year and again I thought I’m going to leave this.

The way I’m talking it sounds like I’ve gone through loads of things and each time I’ve failed them but it wasn’t quite like that and so I then started a political magazine called Total Politics at another publishing company and stayed with that, I left that 2 years ago so that lasted quite a long time and then I had a period where I always wanted to be a radio presenter and it never quire happened and then in 2010 it did and I’ve been on LBC now for nearly 11 years. For a time, I was running the magazine, the publishing company and doing a daily show on LBC but in the end, something had to give so I decided to leave the publishing world 2 years ago and concentrate on broadcasting.

Jason Connolly: Where did this passion for politics (TC 00:10:00) come from because it’s themed throughout your whole career? It seems to have been there from day dot.

Iain Dale: Politics is a bit of a virus, once you really get into it, it never quite leaves you. Even now, I’m 58 now and I have given up any political ambitions but even now a lot of people say, ‘Are you going to stand again?’ And I would say absolutely not, and I do mean it, but from time to time, the virus comes back. And in 2017, the MP for Saffron Walden, which was where I was brought up in Essex, he stood down and I seriously thought for 24 hours, ‘Shall I go for this?’ because I think I would have stood a good chance of being selected. It was right just before the election and in the end, I wrote down on a piece of paper all of the advantages and all of the disadvantages and I came up with 4 advantages and 15 disadvantaged and I couldn’t let my heart rule my head because my head knew that I shouldn’t do it, because I would be giving up a really well paid job in broadcasting to effectively go into a job where I doubt whether I would have become a minister because I was too old. Nowadays, the job of an MP is not what it was when I worked for an MP in the 1980s and in the end I just thought I can’t do this. I can’t put, certainly, my partner through it and I said to him at the point, ‘If I had become an MP in 2005, I’m pretty sure we wouldn’t be together now,’ because the pressure on an MP’s family is enormous and I think politicians go into it for the right reasons but there is a degree of ego about it and I think they can get carried away with things, all the media attention and all the rest of it, and I’m not going to pretend that I wouldn’t have been as susceptible to that as anybody else.

My mother, when I announced in 2010 that I wasn’t going to stand again, she cheered because she said, ‘You could have got caught up in the expenses scandal. I think I’m, as Tony Blair would say, an honest kind of guy but a lot of people who did get caught up in that were completely honest people, they’d just been given really bad advice by the House of Commons fees office or whatever and then were dragged through the newspapers. So, all in all, I am really happy with my life at the moment, obviously I do things other than LBC, I do quite a bit of television now, I’ve got a book out at the moment which has been a great experience to do, so I don’t have regrets even though I know I would have really liked to have done the MP job.

Jason Connolly: When you were running Biteback Publishing, you published over 600 books, you were MD of the company, you founded it, what was the biggest challenge of working in the publishing industry and especially that of political literature.

Iain Dale: Money. It’s cashflow. A lot of your listeners will completely understand that cashflow is the most important thing to any company and if you run a book shop or a publishing company, it’s always going to be tight and I started Politico’s in 1997 with £20,000 and I borrowed £40,000 from friends and family but to start a business like that with only £60,000 of capital, with virtually no working capital was mad and I vowed never to do that again. So, when I started Biteback, Michael Ashcroft, Lord Ashcroft was our main investor and he was really good, he was very hands off, he didn’t try and influence the company in any way. He provided the starting capital and of course we started up right at the worst point, at the start of the recession. So, getting advertising for the magazine was incredibly difficult. We didn’t really become profitable until late 2011, 2012 and at that point, he also owned Dods, the parliamentary publishers, and they wanted to take over Total Politics and I was given a choice whether I would allow that to happen and I did. In retrospect, I think that was a mistake because I knew that they would probably shut it down within a very short time because it was competition for one of their publications, and they kept it going online but they actually shut down the print magazine and I’m not sure in retrospect whether that was the right thing for me to do. So, I then concentrated on the book publishing side which again did quite well. Book publishing is a very, very dicey industry, particularly for smaller, independent publishers and cashflow was always a challenge, but I got a kick out of managing the cashflow if I’m honest.

Jason Connolly: Why?

Iain Dale: I’m not a financial person, I’m not an accountant, I don’t even want to understand accountancy. I can just about make my way through a balance sheet but that part of it doesn’t excite me, but I remember at Politico’s, we were on a knife edge basically for the whole time and I would have an Excel spreadsheet of each of the companies that we owed money to, all of the companies that owed money to us, and it was literally fire fighting the whole time. Maybe I’m a masochist, I don’t know, but that gave me some sort of perverse satisfaction to be able to manage it and we did manage it. I do remember the bailiffs turning up one day though and that was actually for something that I had paid but convincing them wasn’t the easiest thing.

Jason Connolly: When you hired people to work for you in the past, what is it you assess someone on? Do you follow your gut? Do you have a way of looking at people or assessing them?

Iain Dale: I’m afraid to admit that I make up my mind about someone within 30 seconds of meeting them. Let me qualify that. I usually decide whether I think that they’ve got a chance or not of getting the job and I find it very easy to weed out the definite nos. There’s only once where I’ve really been undecided over an appointment. Most of the time I’m fairly decisive. In 2010, when I got the LBC job, I thought I need a PA because I’m trying to run Biteback and do the LBC job, I need a PA. So, I advertised thinking that it would actually be quite difficult to get one but I had 60 people apply which I was astonished at, and it came down to 2 people and one of them was a guy that I’d met at a Tory party conference the year before. He was 17 from a Newport council estate. You know sometimes you meet people and you think, ‘They’ve got something, I cant define what it is but there’s just something about them that is different,’ and he fell into that category, and there was another candidate who worked in a theatre in Liverpool. So, 2 very different personalities and I interviewed them both twice and I just couldn’t make up my mind. So, I got my partner to interview them, I got my business partner to interview them. In the end, I went with my gut and his name was Grant Tucker, he’s now entertainment editor for the Sunday Times at the age of 27 and he’s the best networker that I’ve ever met and he was just brilliant.

He did start a university course at the same time, he decided to delay it. I don’t think he’s ever gone back and finished it actually, but he’s one of these people who he’s got the gift of the gab. I remember, he walked up to Cilla Black in the street once and engaged her in conversation, she ended up taking him to tea at the Dorchester. John Major came to a book launch in the office and he started talking to Grant and then an hour later he left and then he came back and said, ‘Oh, I didn’t say goodbye to Grant.’ He got a former prime minister feeling beholden to this 18-year-old from Newport. He’s just a real character and I know one day he’s going to be a massive TV star I think, he’s just got that sort of thing about him. I always remember talking to the former managing director of Associated British Ports once where I had appointed a book shop manager and I had to sack him after a month because he was so awful and useless, and I was bemoaning this to Stewart Bradley his name was, and saying how did I misjudge that, I can’t believe that I appointed to someone who was so useless, and he said, ‘Well, don’t blame yourself. If I get 1 in 3 right, I think I’m doing a good job,’ and I thought that’s interesting. You’re not going to get it right every time but you can’t let things just carry on as they are, you have to grip it and it’s the hardest thing I’ve really ever had to do in business is sack somebody and I’ve had to do it on a few occasions. Never gets easier and anybody that says that they can just do it, I think they’re a bit warped because it is a horrible thing to have to do.

Jason Connolly: (TC 00:20:00) Do you think the younger generation today lack the social skills of older generations despite the fact we’re more connected than ever?

Iain Dale: I think it’s very difficult to generalise. There are lots of young people who would fall into that category but I’m sure they did in 2000, I’m sure they did in 1980. I think nowadays, I’m constantly inspired when I interview 18, 20-year-olds about what they’re doing and would they even have been able to do a radio interview 20 years ago? I’m not sure. I think they’re much more media savvy, I think they’re much more comfortable with a camera in front of their face for obvious reasons with social media and the fact that everyone has a camera phone nowadays and can make videos and all the rest of it. I don’t think you can really generalise like that.

Jason Connolly: I wanted to talk to you about LGBT matters. In 2003, you became the first openly gay Conservative candidate to contest the parliamentary election.

Iain Dale: No, that’s not true.

Jason Connolly: Oh, okay.

Iain Dale: It’s important because some people have accused me of over claiming here. What I’ve always said was that I was the first person who was selected to be a Conservative candidate having previously told the selection committee that I was gay. I wasn’t the first gay person to stand for the Conservatives, it is a slightly different thing.

Jason Connolly: Did you feel support throughout the party when that happened?

Iain Dale: Yes, absolutely. Theresa May, who was the chairman of the party at the time, she phoned me up immediately after the selection, she had made it her business to get a more diverse range of candidates, which didn’t just mean gay candidates but more from ethnic minorities, more female candidates and I was part of that. I think I actually benefited from that in a strange way, certainly from the top, it was possibly different at a local constituency level. So, I did have the support from the party but when you’re the first to do anything, inevitably you become an object of curiosity. So, I knew that the media would report it and sure enough they did, which didn’t do me any great favours locally. I was described by the Observer of all papers, as the openly gay Conservative candidate, and I took the journalist to task for this, I said, ‘You would never write, “The openly straight Labour candidate,” or whatever, I think it’s a real disgrace that you do that. I don’t mind you mentioning the fact that I’m gay but to do it in those terms,’ I just thought was slightly gratuitous and I’ve never hid. Part of there reason that I hadn’t stood before, and I was 40 years old at this point, part of the reason I hadn’t stood before was because I wasn’t willing to be open about it, I hadn’t come out to my parents but I thought if I don’t start doing this now at the age of 40 it’s going to be too late.

I can remember, and I’ve told this story before so I won’t go on at length but I can remember when I got through to the second round of my first selection in Chipping Barnet, I remember driving up the M11 to tell my parents to tell them and I was thinking, ‘I don’t know how I’m going to do this, I don’t know what I’m going to say.’ I wish I’d done in many years before in retrospect, but you can’t live your life over again.

Jason Connolly: Do you thing being gay has in any way shaped or had an impact, positively or negatively, throughout your career?

Iain Dale: I have said in the past that I think if I had been straight I would have been an MP and I do believe that. Now, that is not to say that I would automatically been selected somewhere else but I think I would have been, I think I would have got a safe seat which means that I probably would have been an MP as well now, but as I say, I don’t live by regrets. I’ll always remember, just after I was selected, a very young guy came up to me a the Tory conference that year and said, ‘I just wanted to thank you,’ and I said, ‘Well, I don’t know you, what are you thanking me for?’ And he said, ‘Because you’ve made it easier for the rest of us,’ and I do think that I did and if that’s my only achievement in politics well so be it but I think if you look at the make up of not just the Conservative party but parliament at the moment, there are I think over 60 out MPs across the parties, more in the Tory party than anywhere else. That was unthinkable in those days and it wasn’t just me, Nick Bowles stood in that election and quite a few others. It just made it a non-issue and I just don’t think it’s an issue for selection committees now. I remember in that Chipping Barnet one, in the end of the first round of the first selection, the woman in charge of the meeting said, ‘Is there anything embarrassing about your business or private life that could cause embarrassment to the local party?’ And I just said, ‘Well, you should know that I’m gay but I’m also a Westham United supporter, I don’t know which might be more embarrassing,’ and they all laughed, but the agent rushed out after me at the end and he said, ‘Why did you say that? You’ve just lost 2 votes there,’ and I said, ‘Well, they asked me a question so I thought I’d answer it.’

Jason Connolly: Which one did you lose 2 votes for, Westham or being gay?

Iain Dale: That is a very good question to which we will never know the answer but before the final, I missed out getting to the final by 2 votes and had I got into the final I would have been up against 2 women and in those days if it was 1 bloke against 2 women invariably the bloke always won. So, I do look back and thing slightly, ‘What if?’ I could have been Theresa Villiers. There you go.

Jason Connolly: Do you think in 2020 there’s still a lot that needs doing in terms of diversity in the workplace?

Iain Dale: I think certainly in terms of racial diversity there is. I’m sure there are some sectors where it’s still difficult, more difficult for gay people, less so in metropolitan centres. I think the legal profession and the banking profession are starting to be better in terms of diversity in terms of gay people. So, there’s always more to do. I think in politics and the media, and the arts in general I think you could almost argue there’s an over representation of gay people if such a thing is even possible, I don’t know. Nobody really knows what percentage of the population is gay anyway, some people say 5% some people say 10%, I have no idea. So, the fact that there are about 10% of MPs now you could say job done. I’m not sure we should look at it like that but in terms of racial diversity I think that is the challenge because if you apply for a job in a professional environment and your name is Undab Eningi (ph 27.08), I suspect your chances of getting an interview are rather inferior to those of you who are called John Smith and that’s wrong.

Jason Connolly: Moving on, do you have success habits? Is there things you practice every day which help to make you successful? Some people meditate, some people work out, is there things you do every day which you think drive your success?

Iain Dale: Absolutely nothing. No. I am a bit of a workaholic. If I’m watching television, I’ve got my laptop open and I’m doing stuff on it. I like lists. I wrote a few weeks ago, I do a weekly newsletter to people who are interested in what I’m up to, if you want to sign up go to iaindale.com, and I started off by these words, I said, ‘I think I’ve lost the art of doing nothing,’ and I genuinely think I have. I can’t just sit down and watch television, and watch a box set. I cant just sit down and read a book. I only read in bed which means I only read about 3 pages a night before I fall asleep. I used to be a veracious reader, I love watching lots of box sets but it’s very rare that I will sit and watch something. I’ve got back into cricket recently, so I’ve been watching the different test matches, but I’m doing something while I’m watching. I like playing golf but I’ve found over the years I’ve only got a 9-hole attention span. I get bored after 9 holes even if I’m playing really well, I think I don’t know whether I want to do 18 so I either quit after 9 or 12 or something.

Jason Connolly: I’m very similar to that. You’ve got this passion and you love what you do and I think that’s the big driving force in what continues to keep you going.

Iain Dale: Yes, I am quite passionate about what I do and because I’ve got to a stage now where virtually everything I do I really enjoy, I’ve always got something to do and I can’t remember the last time I thought, ‘Oh, what shall I do now?’ Which is kind of sad. It’s good but its also a little bit sad I think. I would love to go on a 2-week holiday, leave my phone and (TC 00:30:00) computer behind. Could I do it? Not so sure.

Jason Connolly: I’m not sure LBC could have you going for that long.

Iain Dale: Well, that’s true because the management hate you going on holiday because if they think you’re on holiday the listeners might drift off to another radio station and not come back, so there’s always the pressure to not go away for too long. Bearing in mind with COVID and everything, I’ve only had 1 week off this year so far and normally when I get to July, I feel a bit stressed out, a bit tired, I know when I need a break, but having broadcast from home for over 4 months, it felt like a 4-month holiday to me if I’m honest. I’m sitting here now, recording this with you in my bedroom using the microphone that I use to do the programme on and most people didn’t even realise I wasn’t in the studio.

Jason Connolly: One time your internet kept dropping out, I do remember one distinct episode.

Iain Dale: There were 3 occasions in 90 programmes where we had a problem. One of them was actually potentially awful because it was in the mental health hour and I was talking to a man who was saying he was thinking of killing himself and the line went. So, it took me 2 minutes to dial back in and I just typed on the screen to my producer, Robbie, ‘I’m back,’ and luckily Emma Kenny, she’s with us all the time to give professional advice, obviously I’m not qualified to do that, when I came back she was talking to the guy and they didn’t even know that I’d gone.

Jason Connolly: We’re running out of time.

Iain Dale: It’s a podcast, it can go on for as long as you like.

Jason Connolly: That’s also true, I’m thinking more for your sanity, someone starting out in business or someone that’s just leaving school thinking they want to either go into the world of politics, media, or just starting a business, what advice would you give to young people? We have a lot of graduates and young people who listen to this particular podcast.

Iain Dale: I think if you’re starting a business, you’ve got to be sure that your idea is a sustainable one and you’ve got to take advice. You may think that you’ve got the best idea since kingdom come but there may be others out there who’ve got there before you that you haven’t quite realised and if you don’t have a business background you’ve got to get the confidence you can actually run a business because there are lots of people out there with good ideas who are very good marketeers, very good sales people, but don’t know the ins and outs of running a business. In some ways, it’s common sense but there are lots of tricks of the trade to learn as you go along. You need a few mentors I think, talk to people who’ve been there done that. Doesn’t matter how old they are, they will all have experiences that they can share with you to make sure that you don’t make the same mistakes that they did. So, it depends what kind of business it is, I suppose, if you’re starting a manufacturing business, I’ve never done that but there are things you need to know which you wouldn’t if you were starting a retail business or a service sector business. The one thing, and this is what everybody will say, is cashflow is king. If you go into a business with that one thing in the back of your mind all the time, and make sure that you have enough start up capital, I think that was the mistake that I’ve made on several occasions, not to have enough start up money.

A friend of mine started a forestry machinery business and I made an investment in that and he’s just turned 29, started it when he was 26 and I think it’s been really useful to have me there to ask questions of. I’m just at the end of the phone, he rang me up the other day and said, ‘I’ve got all this money outstanding, should I start charging interest on bad debts?’ So, we had a long conversation about how he should chase bad debts because that’s always the most difficult. Not necessarily bad debts but people who had just gone over the 30 days or whatever, the 60 days. So, I think having someone there because it can be a very lonely experience, people who have never run a business don’t get that. The biggest responsibility I felt, certainly at Biteback, was to all my staff because I knew that any wrong decision I made could jeopardise 12, 15, 20 jobs and that dos weigh on your mind. People think that anyone who runs a business can be very harsh, uncaring and all the rest of it, all they’re in it for is for the money that they can get out of it, and of course there are people like that, but I think most employers, particularly for small companies, they recognise that their employees are their biggest strengths and if you treat your staff well, they will treat you well. They will go that extra mile, they will stay until midnight one night to get something finished if it means that the company can make a bit more money out of it because they know that in the end they will be rewarded for it. This is where I hate these companies that think they can get the best out of people just by paying minimum wage, they should be grateful for a job. I’m sorry, that is not how you motivate people.

Jason Connolly: I totally agree with you. I remember when I started my business what used to fill me with dread was the tax side of things and actually I was with a partner at the time and he knew all about business accounting and the day just before my company was about to launch and I opened it on Company’s House, he moved all his stuff out and broke up with me and it was like my world tipped upside down because it was like, do I actually have that inner strength to know how to do any of this?

Iain Dale: What a bastard.

Jason Connolly: I know. If you’re listening now, shame on you.

Iain Dale: You bounced back from that in the way that I was saying before, presumably.

Jason Connolly: Yes, it’s absolutely true. Iain, it’s been so nice to talk to you, I think it’s been such an interesting conversation. Is there any last things you would say to anyone out there that’s listening to this, that’s thinking about a career? Maybe 1 line of advice.

Iain Dale: 2 things. First of all, try and go for it. There are so many people in this world who get to 60 and think, ‘If only I had the courage in my convictions, if only I had tried that.’ The worst you can do is fail and failure can seem awful at the time but you learn from every failure and there is a different between the United States and us here where most people in the United States have had business failures. Here, if you have had a business failure people look down on you and think ‘loser’ and it should be like that because most entrepreneurs have more than 1 idea and if 1 doesn’t work then they go onto the next one, and in the end that’s why risk has to be rewarded and that’s why 1 of the things that I don’t think this Conservative government quite understands that if they remove all the incentives from entrepreneurs, they will go and set businesses up elsewhere, it’s as simple as that. I think if you have a dream, try and fulfil it and I know it’s easier said than done but if you have the determination, you probably will be able to get at least some way towards it and the second thing I would say is to buy my book, ‘Why Can’t We All Just Get Along, Shout Less, Listen More.’ It’s primarily about public discourse but there’s quite a bit of autobiographical stuff in it. I do talk about the business world and why we don’t appreciate business in the way that we should, I talk about some of my own businesses, I mean I’ve run 7 over the years, and so far, touch wood, it’s had quite a good reception.

Jason Connolly: It’s also available on audiobook.

Iain Dale: I don’t do audiobook but loads of people say that’s how they’ve listened to it. Other people have said they’ve read the book and they can hear me reading it while they’re reading it if you see what I mean, they can hear my voice in it, which I think was the nicest thing anyone can say.

Jason Connolly: Thank you so much for joining me, it’s been a delight to talk to you.

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