Story 21: You've Got A Week And Then You're Out

Cameron Laird

Cameron Laird

Published on: 07 July, 2022

Updated: 10 March, 2023

UK's Most Hated Sales Trainer

Broke, Selling & Persistence

You know how every couple of weeks we tell you about how great of an episode you missed on the last go-around of The Chirp? Well, guess what, you missed another amazing episode and not just any episode, you missed our very special 20th episode of The Chirp! Last week, we took some time to recap on all of the amazing conversations we've had on The Chirp thus far. From Daniel's incredible jaw-dropping tale of financial ruin from a divorce gone bad to Rahama's impact in the world of sustainable agriculture and gender equality in Africa, we took a trip down memory lane and revisited our greatest hits so far! So before you dive into our regularly scheduled programming, circle back to our culminating episode, and relive some of our favorite conversations we've had on this podcast - check out Story 20: Our Best Moments So Far.

This week we took a trip across the pond and are bringing you a special guest from the UK. Dubbed The UK’s Most-Hated Sales Trainer, we got a chance to sit down with Benjamin Dennehy and talk about the world of sales and the journey he took to go from failed starving lawyer to a renowned salesman. Filled with high-energy jokes, riveting tales about drunken nights in England, and stories ultimately of triumph, this episode is sure to keep you in tune for its duration. Enjoy the show!

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This Episode In A Nutshell

Finding your calling is not easy. Some people search their whole lives to find that one thing they are good at, while others are just born with a natural knack for something. Our guest this week, Benjamin Dennehy has experienced a little bit of both to get to where he is today. Having earned the name The UK's Most Hated Sales Trainer, Benjamin was a lawyer by education but found out that sales was his true calling all along. After a grueling 20+ year journey of learning the ropes of his craft, while trying to scrape together just enough money to put food on the table for himself and his family, Benjamin has now amassed quite the name for himself and turned his life around for the better. Listen to our conversation with Benjamin as he walks us through what it takes to not only be a great salesman but to have enough persistence to make it through tough financial times.

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Audio Transcript of Story 21: You've Got A Week And Then You're Out

Opening Monologue

Hello everyone, welcome back to another episode of The Chirp: A Podcast By Pigeon where we interview amazing guests and hear their stories about relationships being affected by money and by loans. I’m your host, Cameron, and I’m very excited to bring you this episode here today. 

During my online travels on LinkedIn,  I stumbled upon a sales trainer a couple of years ago by the name of Benajmin Dennehy. A few things struck me straight away that made him memorable, and I don't think these memorable things were by accident. 

Firstly his no-nonsense approach to selling, saying things like that over 85% of people in sales don’t want to be there. Also, his big red hat with the phrase “make salesmen great again”, and his witty LinkedIn posts detailing the awkwardness but necessity of cold-calling. But the best thing for me was his self-proclaimed title, The UK’s Most-Hated Sales Trainer. 

Now as an ex-salesman myself I know how tempting being in sales can be and how your relationship with money can lead to a different lifestyle. For me, I always had the money coming in when I was working in sales but I was still always asking for loans from friends and family because my salary wasn’t the issue, it was my money management. 

So I wanted to invite Benajmin on to the show and hear his story, hear about his relationship with money himself and did loans play a part in his early relationships before his success as the UK’s Most Hated Sales Trainer. 

To my delight, he said yes to being our latest guest and I’m very excited to share Benjamin’s story with you all. Expect honesty, humor, and, if sales is your jam, some relatable facts! So enjoy.

Cameron Laird 

Benjamin, I'm a big fan of your LinkedIn presence, of your mantra as well. You're known as the UK's most hated sales trainer. Can you tell us a little bit about, you know, how you actually came to be in sales and how you were able to adopt this amazing moniker as well?

Benjamin Dennehy 

Yeah, sure. So like most people in sales, this is not what I had planned for my life. I didn't want to be in sales. Never thought I'd be in sales, but I fell into it. So I qualified as a barrister back in New Zealand. The plan was to be a lawyer - that was my life goal. That's what I wanted to be growing up.

But I decided before I settled down, I'd go traveling. So I came to England, and ended up working in pubs and bars. This is at the beginning of the century. So this is like December ‘99. So this is going back a long time. Back then everyone in pubs in England was a Kiwi, an Aussie, or South African. We ran the liquor industry pretty much.

So I did that for many years, and had a lot of fun. Then finally went home and thought, “This is it. Time to grow up, time to be a lawyer”. But I realized I couldn't live in New Zealand. It just hit me like a punch to the face. It's a beautiful country, but it's after years of being in Europe and traveling…

So I came back to England and I had to get a job. And what do you do if you've got a law degree, but no other skills and a law degree is useless? There's literally nothing you can do. So you can communicate pretty well. You can string sentences together and you don't dribble. So you are now qualified to enter the world of sales!

And so I did. My first sales job was in recruitment. I worked for a big recruitment company in London. I set a company record though. I was there for six months and didn't recruit anyone! I was terrible. And I was actually given a week's notice. I was told, “You've got a week and then you're out.”.

And I remember sitting in a pub at lunchtime. This was on a Friday. They told me this. So I went to the pub, sitting there with a pint, nursing a pint thinking, “What the hell am I gonna do? I'm gonna be out of a job in like one week”. So what I did the next week was I came in and I just hit the phones really hard.

They're always prospecting-  canvasing as they called it when I was doing it, canvasing - looking for jobs for the recruitment company to then be able to go in and film. So I just hit the phones hard and I had a really successful week of setting up appointments, which is one of the hardest things for people to do is to get in front of prospects.

So I had a reprieve. I got to the end of the week and they said, “We're not gonna let you go. I want you to do more of what you did this week next week”. Fine. So I spent another week hitting the phones and that's all I did again. So get to the end of those two weeks and they said, “We'll offer you a new job. You're not gonna be a recruitment consultant. We want you doing solely business development for us, and we'll pay you for every new contact and we'll pay you for meetings”. That seems like an all-right deal. So that's what I did. That's what got me into the world of prospecting. And after about a month of doing that, I got poked, I couldn't believe it.

Some company that specialized in setting appointments for advertising agencies had heard about me from a former recruiter that had started work and said, “You gotta hire this guy. He's really good on the phones”. So that took me straight then into the total world of business development. And I was doing it for advertising agencies primarily based in London, setting up appointments and they'd go on it. 

After a few years of that. I decided, why am I working for this company? Why don't I just go out and find my own advertising agencies and offer this exact service? So that's when I became self-employed. So that would've been 2006. So I went out and I sold my services and said, “Look, I'll do a better deal. Instead of sitting in some foreign office and you not knowing what I'm doing, I'll come and work in your offices, come and give you a day a week and you can listen to me. You can hear what I'm saying and we'll set appointments”. Prospects, they all love that. That's much better having you in our offices.

So I'd had two or three clients at any one time, each paying around three grand a month to get four qualified appointments. So it was a pretty good living. But after doing that for about 10 years, I realized I'm gonna be doing this for the rest of my life unless I figure out how to sell. So I started going on all the sales meetings that I used to set up for my clients, and I realized very quickly that nobody knew how to sell.

And it just hit me. I'd never really thought of it before. So I started on a journey, and I met some great people along the way. A guy called Marcus Cauchi gave me a lot of advice and guidance and I learned a lot from him. And then I just went out and I got good. I read a lot of books, studied psychiatry, and just started doing the stuff that people said would make you good at selling.

So rather than just reading every book, like every salesman does, and doing nothing, I decided to get good at the stuff that said you should get good at. And it got good, big, and capitalist. I've repackaged it, rebranded it, and I sell it!

Cameron Laird 

Brilliant. And I'm very interested in you as a salesman, not as much as a sales trainer but how you manage your business being a sales trainer. I saw an interesting comment on your LinkedIn a while back. I think you were talking about sales targets and you said you'd already hit your yearly target already. And you were taking some time to focus on other things aside from sales.

Firstly, what a wonderful place to be in. But can you take me back to a time maybe things weren't going as swimmingly in your career and what you did to survive financially as well.

Benjamin Dennehy 

Very easy. I mean, you go back, uh, it feels like a long time ago now, but it wasn't really a long time ago!

So you go back to around 2016, time. I was broke. I wanted to get really good. I wanted to make sales training my primary source of income, but I still have my prospecting business. And what you discover is human beings need to find some compelling reason to motivate themselves. 

To motivate yourself without compelling reasons is really hard. Now, some people are very good at setting a future goal that they're motivated to achieve. I'm not that strong. I need something that motivates me in the present. So most people set a goal for pleasure, but I'm gonna move away from pain a lot faster. So I realized that the only way I could motivate myself to really pull my finger out and get good at this sales training light was I had to get rid of all my clients.

And literally, try and make money only selling in what I do. And that was scary because I'd started that in 2014, that actual thought process was about 2015 that I decided to do it. And I had a baby that was just over a year old, my daughter, we were living in rented accommodation.

And my wife, she goes, “How are we gonna survive?” I said, “The world's awash with credit, right?” So banks were chucking credit cards left, right, and center back then. So I said, “We're gonna live on credit cards ‘till I make it”. She goes, “Okay, what's the worst that can happen?” I said,” The worst that can happen is I go bankrupt!”

That's literally the worst that can happen, right? And I said, “Right now we don't have anything really to lose so it’s do or die here”. And she said, “Well, I trust you. I'm pretty sure you'll make it work”. I said, “Let's do it!” 

But it was hard. People say to me, it must be easy for you because you teach what you do. And I say to people, “You try selling what you do when you're not very good at what you do!” The hardest thing about being a sales trainer is actually getting really good at the stuff you do. So the journey on that way was fraught with difficulties and I wanted to quit so many times I was in tears, many times thinking I couldn't get some of this stuff to work.

My mindset was shitty struggling for money. I'm glad it happened. I think people need to experience not having a lot of money to appreciate money. And I remember when I was doing my prospecting, money wasn't an issue. And then when I had no money, 20 quid suddenly became a lot of money!

And I remember before then now saying, how could you not afford 20 quid? You'd hear people say, “I can't afford to do this because we just don't have the money”. And I used to say, “What the hell's wrong with you? Why can't you have 20 quid?” 

But experiencing being in a position where that was a lot of money really changes your appreciation for other people. You can be more compassionate. But it also motivated me. I don't ever want to be like this. So, I stuck at it at and at one point I had to go on working tax credits, you know, that's like a bit of a bailout from the bank. I mean, it turns out a lot of people can get it, but that was one of the most humiliating moments in my life.

It's like, oh my God, I actually have to ask for help. But those little bits of money kept me going. So I nearly went bankrupt. I nearly lost everything. And also I think it was hitting rock bottom where I thought, well, I can't go any lower now. The only way from here is up and I just kept at it.

This is what I teach people. There's no quick fix to this. It was just persistence and consistency and doing the same thing and learning from the mistakes, writing down my mistakes, figuring out what I'd done wrong, going back and trying something different. Fast forward though, to today. And you know, in the last three years I've done over a million pounds in fees.

I own my own home, paid cash for it. As you say, I hit my sales target six months into the year and all I've done is got really good at the things that I was really struggling at when I first started. COVID helped because it moved me online. So it opened up the world. So I went from just focusing on the UK to suddenly the world.

So people say, “Well, that's luck!” I don’t know if you can call the pandemic ‘luck’. But what you can say is preparation and opportunity came together. And I had prepared all these years of working hard. So I was in a place. I created a brand, I created a reputation, and then COVID hits, which was the opportunity. And I pivoted very quickly - That's the business smart-man word! 

And, from that, it just went from strength to strength. I mean, the business started really growing in 2018. 2019 was a very good year. And then we had the pandemic and the last three years have been really good. So, yeah it's been a long road, it's been hard, but people never see the hard stuff.

They only see the finished article. And I try to get that across to all my students and most of them get it. Some don't! Most companies don't get it. They're after a quick fix! Just come and give our guys some training and everything will be fine. It's like, no it doesn't work like that. So yeah, that’s my story!

Cameron Laird 

Amazing. Thank you for sharing. I'm not too sure of the percentage but a lot of people in sales don't want to be there. I think it's as high as 80 something percent. Am I correct? 

Benjamin Dennehy 

Probably even higher, yeah it's high. 

Cameron Laird 

But you know, maybe they are there because they have mouths to feed, they have their own mouth to feed, they have a lifestyle they have to keep, they've rent to pay, whatever it might be, but they don't love what they do. And you famously say that if you don't wanna be in sales, don't be in sales! 

Do you train a lot of people that don't want to be in sales, but have to be because of financial implications? Do they have families? And if so, how do you train those people? 

Benjamin Dennehy 

The thing about being at sales is if you fall into it, as most people do, you get about two to three years in and, just like me, when I had just graduated from law school and needed a job, you realize very quickly you have no real transferable skills.

What do you do if you've been a salesman for five years, what other job can you just walk into? Other than another sales job? There's really nothing. And I keep scratching my brain. You end up doing something which you consider even worse than selling something, meaning like data entry, or you have to go work in a coffee shop because you suddenly realize, what skills can I take?

We see a lot get stuck. Because what else can you do? You don't have the money all the time to go and retrain. So for a lot of people, it's not a career, it's more like a community-based sentence. And so they have to tough it out. And I'd say, out of the people I train, there are two types of people. You've got the corporate and you've got the individuals. The individuals get the stuff the best and run with it because they're investing in themselves.

They've come to the conclusion they're gonna be in sales and if they're gonna be in sales, then they'll get really good at it. When you do corporate gigs, though, a lot of the time you're invited in and you've got a room full of hostages. They're only there because the employer sees you need sales training, and they're not gonna do anything because they don't care.

So I'd say about 70% of people that you train in that environment don't change. You get a handful, 10% really grab it and they run with it and they have success. But the majority of people don't like change. And salespeople have to change if they want to get good at selling. And if you don't really wanna be doing something deep down, would you put in a lot of real energy and effort outside of office hours or in-office hours, when all you need to do is just maybe miss the target and you'll be fine? 

Yeah, so the incentive is not to get good. And you see everyone say salespeople are motivated by money. If that were true, they would be so much better! 

Cameron Laird 

And yourself Benjamin going back to your earlier years, moving from New Zealand to England, when you were younger, it must have been very challenging, very scary.

Can you talk a little bit about that period when it came to money, specifically, and was there ever a time where you asked for help when you were making that transition? 

Benjamin Dennehy 

My first job in England… actually turns out it was a sales job… I never really made the connection there!

So that was my theoretically… I got a job working in Paddington (London), and it was for a company that basically sold… It is sales. I completely blanked this out until you brought that up, that's interesting! And basically they created magazines which they said had articles in it, but basically you would sell the advertising and in an exchange for buying the advertising, you got to write an article.

So they had all these different categories, so that was my first job and that paid me 150 pounds a week. And by the time I'd paid my tube fee for the week, by the time I'd paid my board, by the time I'd bought food, I had about 15 pounds a week left, in my pocket. So I was back to living like a student!

So that was challenging, but it's amazing how drunk a 23-year-old can get on 15 quid if they really wanted to try, right? So it was a bit lonely at times because I didn't have any friends. I'd come over on my own. So, I had no friends over here so it was tough.

My father was over here as well. He'd come back to England because he'd spend a long time in New Zealand. He wanted to come back to spend time with his parents because they were getting older. So I had him to fall back on worst-case scenario, but I never wanted to. Dad said, “But you're a quantified lawyer, what the hell is wrong with you?” 

So I stuck it out. And I had no plan for my life as I said. And then when I finally got my first sales job, I hated it. I'll be honest. I absolutely hated sales because no one showed you how to do it. All they did was you'd have two days of product knowledge. They’d say, “This is what we do. This is how we do it. This is how you should present yourself in a meeting”. They give you all this stuff. 

And then they just released you onto the phones and say, “Now get appointments!” And then when I got the other job with the actual company that specializes in setting appointments, there was no training, literally nothing.

It's just, “You sound good on the phone. You should be alright, just get on with it”. So no one really helps you. Now there are some companies that do help you, but a lot of sales training is all product knowledge and it doesn't teach you anything practical. So it was a struggle.

And I was lost for many years. What am I gonna do with my life? You know, what do I do? What do I do?  But I knew I could get no other job. I looked at other jobs, but sales, that's the one I'm stuck with because I can make a living. And I think that's it for a lot of people. They can eak out a living doing this and you are never not gonna get a job.

Yeah, it's very hard not to have a sales job. You get fired one day but you can have a job within three weeks at somewhere else and you'll take any job that's willing to pay you. It takes them at least three to six months to figure out your crap anyway. And then in that that three to six months, you're looking for a better sales job anyway, that's what you do.

So I know what it's like for the average salesman, because I don't consider myself brilliant, but I know I'm much better than most people. It's been an amazing journey. It's taken a long time too.

I mean, it's 2006 to 2022. Yeah. So I dunno what that is but that's a while. That's what 16 years doing this? And I've only made my money in the last four. 

Cameron Laird 

Brilliant. I'd love to pick your brain as well in terms of behavior and psychology. I heard you talk about why salespeople suffer sometimes because of how they're programmed as children not to talk to strangers, not to interrupt people, fascinating stuff.

Do you think any of that early molding also contributes to us being hesitant about talking about money, in general, or asking for help with money? I know obviously, you're in sales, so it's different to asking for a loan, but in terms of behavior, is there something there in terms of why we're hesitant to discuss money or lend money?

Benjamin Dennehy 

Yeah. Well, growing up you got messages about money from your parents. And so things like, well, you know, it's alright for rich people or people like that, they stand on the little man, you know, so that your very socialist look towards money. 

If you come from a real working-class sort of background, you hear. “Rich people just stomp on the working man and that's how they make their money”, or, “No one in our family's ever gone to university”, or “You have gotta be corrupt to be rich”. So you get all this fed into you and you're constantly told that 20 quid is a lot of money. It's very expensive and all this.

So you form this over your whole life and then you carry it through with you to adulthood. And it's amazing the number of salespeople that don't like talking about money, they feel uncomfortable. And so your money concept is gonna determine your success. Now money concept can change. I had a pretty shitty money concept. And I've now fundamentally changed. I mean, the figures that my head used to consider to be an insulting figure is now so much higher! If someone says, “Benajmin, we want you to come and talk to our people. I want you to come and spend a couple of hours talking to them. We're willing to pay you like a thousand pounds”. 

I say, “No, no. My minimum speaking fee is five grand!” And I say it with certainty. And if you don't wanna pay that, I'm leaving. But you go back five years, that's quite a lot of money, so it can change. So the better you get, the better your mindset gets.

If you are selling million pound homes, but you only live in a 400,000 pound home, sometimes you can win but when you're talking about the price, prospects pick up on these things. So you have to project utter money. There's nothing wrong with money. You have to tell yourself that. There's nothing wrong with money.

You can misuse it, but there's nothing wrong with the concept itself. It's a perfectly good concept. So yeah, money programming, the Romans had it, you know. Give me the boy until he's seven and I will show you the man. So long before modern psychiatry, they knew that the first seven years of a child's life was the most important because it will set the person on the trajectory that life is going to take.

Now it's not a hundred percent, you know, some people can fundamentally change if they've had rotten programming, but most of us have rotten programming, particularly around money.

But again, rich people don't have it. It's funny how rich people perpetuate rich people and poor people perpetuate poor people.

Why is that? And it's not because of the money. Something enables that it's the programming. So everyone must check their programming. How do they view money? How do they feel about it? Do you have to save it for a rainy day? Do you have to work hard for your money? All of this sort of stuff. So yeah, it's in there.

Cameron Laird 

Very interesting stuff. Benjamin, It’s been an absolute pleasure talking to you. Before I let you go this morning, how can people find you if they want to follow your funny stuff on LinkedIn and social media, or even hire your services? Where can they get you?

Benjamin Dennehy 

So LinkedIn obviously is the place you'll find me. I don't use any other social platform. So LinkedIn is where I hang out. UK's Most Hated Sales Trainer. You'll find my website, obviously again it’s I'm running an event actually, though on the 7th of October at the Aston Villa football club. Me and the UK's number one, motivational business speaker, Brad Burton.

We've come together. For a day of money, mindset, motivation, and miracles - miracles are not guaranteed. Brad’s built a multimillion-pound networking business, very successful. He's come from a very poor background. So we've come together. We're gonna put on a day of high energy, high learning to share with people the struggles we went through and what we did to conquer it.

Cameron Laird 

Fantastic Benjamin, it's a pleasure to have you on, as I said, big fan of your work, of your LinkedIn profile as well. I've been in sales as well since 2015, and I hated every moment of it. And I dropped out about three years ago just before COVID. So to hear you say that it's not for everyone and it's okay if it's not for you and not to do it was always very refreshing to me. 

However, I do love your take on it and the stories that you tell and your outlook and your program. Brilliant Benjamin. We'll leave it there. Thank you so much and best luck with your event as well.

Benjamin Dennehy 

Thank you very much. And I, I appreciate you having me on Cameron.

Outro Monologue

Great to hear an honest account from Benjamin about his own journey, I didn’t know that his financial success has only really taken off in the last four years, and great to hear how COVID and the lockdown allowed him to access a bigger market which was great to hear. 

But what struck me was when he said that he was glad being broke happened to him, because he became more appreciative towards people and more appreciative for less amounts of money. Benjamin’s right. When you are going through a hard time financially, £20 or $20 is a lot of money and that realization doesn’t leave you even when things improve for you financially. You’re always aware of how little you can survive on.

Interesting to hear Benjamin say how no one ever really sees the full journey of someone’s career and if you were to take a look at his Linkedin and check out his positive, honest, unpretentious content, you would think that life is a breeze for this guy, but I found this story about the broke times very interesting, as he had a small daughter and family to provide for as well. 

And something that resonated with me is Benajmin saying that he went back to living like a student when he moved to the UK as a young man, which brought up the aspect of money vs. happiness to me, and that was a big reason why I was so compelled to have Benjamin on the show. He had his qualification to be a barrister, but he chose to work in bars instead. How does one truly strike the balance between loving what you do for work, and doing a job for money to fund your lifestyle. 

Sales to me was never a passion, it was a means to an end. I would go into the office at 9am, entering what seemed like a prison, and I would dive straight out of there at half 5 in the early evening, thinking my day was only truly beginning then. While my salary was high, I was still looking for loans at the end of the month for rent, for groceries, and I learned after a while I was unhappy in my career. I was wasting my time. 

You have to love what you do and do what you love and if that means taking a hit financially, living frugally once more and, from time to time, taking some loans from friends and family as well, then that might be the better path to take. 

However, if you’re like Benjamin and you love sales, power to you because you are doing what you love. That’s all for this episode. If you have some similar stories to share about your financial journey and relationships, do reach out!

We have another exciting guest for you in two weeks, I won’t divulge but expect to be entertained. Until then, I hope you’re all having a wonderful summer. Stay safe.

About the author

About the Author

Cameron Laird

Podcast Host of The Chirp

Cameron Laird is a professional podcaster for Pigeon and the host of The Chirp podcast. He has a passion for creating content that is both entertaining and informative. Having hosted numerous ventures over the course of his career, his experience in the podcasting industry has made him a valuable asset to the Pigeon team. Cameron's ability to connect with his audience and provide meaningful content regarding topics like financial education has helped grow The Chirp to be a staple within the Pigeon community. He is an excellent communicator and is committed to improving the world through conversation, dialogue, and shared experiences.