20 minutes of Sales Advice - Rory Sutherland, Daniel Priestley and Benjamin Dennehey

22 May 2026 · 19 min · 10 chapters

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In short

Sales advice focused on relational selling, direct outreach, and defining “leads” as detectable signals of interest. Guests argue against short-term “efficiency” tactics that avoid real conversations, and for building long-term customer value through trust and reciprocity.

Guest backgrounds

Rory Sutherland (direct marketing influence; cites Drayton Bird and Cialdini/Dan Ariely-style ideas). Daniel Priestley (runs ScoreApp; claims rapid UK growth). Benjamin Dennehey (sales/marketing strategist; emphasizes being “hated” rather than liked; permission-based openings and skepticism of self-labeling as an expert).

Key claims

Do the “disgusting” work of 3,000 customized cold DMs; optimize for future need (“next car” question). Transactional capitalism vs relational capitalism. Fixing problems can increase loyalty. Cold calling isn’t dead; LinkedIn posts that “tell people what they want” outperform.

Notable examples

ScoreApp growth via ~100 DMs/day (late 2019–early 2020). DoubleTree cookie as unexpected generosity. Car salesman story (ask a different question). Online travel business: website converts 0.8% vs phone 35%; don’t hide phone number to chase low acquisition cost.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Importance of Direct Messaging

0:45 to 2:00

Discussion on the necessity of direct messaging for business growth.

“So all through late 2019 and 2000 and early 2020, I'm firing off 100 DMs a day.”

Building Relationships through Cold Outreach

2:00 to 5:10

Exploration of strategies for building client relationships through cold outreach.

“And there's a story I really love about this, which comes from Drayton Bird, who's the great guru of direct marketing.”

Salesperson Behavior and Accountability

5:10 to 7:30

Analysis of common issues with salespeople and their responsibilities.

“Anything to avoid having a conversation.”

Understanding Sales Meetings

7:30 to 9:50

Insights into how to analyze the effectiveness of sales meetings.

“the double tree does this spontaneously fundamentally primes you for reciprocation OK, but also establishes trust, which is this is obviously long term relation.”

Transactional vs. Relational Capitalism

9:50 to 13:00

Discussion on the difference between transactional and relational capitalism and its impact on customer loyalty.

“And I get it, you're using it to sell something.”

Lead Generation Strategies

13:00 to 14:03

Overview of effective lead generation strategies for businesses.

“But what we have to work is we've got to play the odds.”

The Dilemma of LinkedIn

14:03 to 14:36

Explore the mixed feelings about LinkedIn as a necessary tool for sales.

“it's proof of why LinkedIn is just a bit of a cesspit in some ways.”

Cold Calling Challenges

14:36 to 15:10

Discuss the frustrations and challenges of cold calling in sales.

“You know, I've been self-employed for 20 years and I love it and I would never work for anyone.”

The Importance of Timing

15:10 to 16:38

Understand the significance of timing in receiving cold calls.

“What's your what's the reason behind that?”

Value Over Cost in Customer Acquisition

16:38 to 19:07

Learn why focusing on acquisition costs can undermine customer value.

“So it's a mixture of repeat purchase and size of overall market.”
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Transcript

Automatic transcript. May contain errors.

0:00They don't have a massive network. They've got this idea and they post it on social media and no one does anything. So that's like, is it a bad idea that people don't want to join the waiting list? No, it just means you're lazy sod. So basically you need to do the disgusting, horrible, annoying work of direct messaging 3 ,000 people. So, you know, ScoreApp, right? So score ups, we've just been notified that we're one of the fastest growing companies in the UK. We're on the fast growth index. We won scale up of the year. We're less than five years old. We're probably a 50 to 100 million dollar business at the moment.

0:41I started that by messaging 3000 people. Now I messaged 3000 people because I didn't want to post on social media about something I wasn't sure about. So all through late 2019 and 2000 and early 2020, I'm firing off 100 DMs a day. and when i say firing off like not just cut paste send but cut paste customized send cut paste customized send i'm like cold outreach um cold dms uh across you know social media hey i noticed this such and such i want to share a quick story with you uh over the last five years we've been doing this campaign and it's really worked well i want to explain it to some more people you interested in knowing how we did that would you like the full story oh yeah i'd like the full story okay cool so here's the full story um if you're interested to know uh some of the tools that we use just join this waiting list right so um or in that case actually i went with a um an introduction workshop come along to this little introduction workshop i'm going to do a one hour explainer workshop where we introduce you to how we've been doing this and yeah 3 000 cold dms i always get frustrated when people say oh but it's easy for you you've got a big audience i don't put most of that stuff on the on on the social media i i a cold call a cold message you know i kick off the same way you guys would kick off so so what i'm saying is that there's this weird cult of short-term efficiency gains which i think in lots of areas of business are deeply deleterious to what a real brand relationship and what the customer value exchange over time should really be.

2:19And there's a story I really love about this, which comes from Drayton Bird, who's the great guru of direct marketing. His book Common Sense Direct Marketing. For American listeners, he's kind of the British Lester Wonderland. He's still alive. He's in his 80s. He actually gave his last talk about direct marketing probably about a year and a half ago. Brilliant, brilliant man. He was my first boss and, you know, a huge influence on everything I believe and think and how I think and so on. And Drayton told the story, I think it's in his book, of America's most successful car salesman. And presumably sometime in the 60s or 70s, this particular title existed, and it was just this guy who had an extraordinary record of car sales.

3:03And they asked him what his secret it was. He said, it's very simple. He said, I do something that no other car salesman does. As soon as someone comes in who is vaguely interested in some sort of car, I ask a completely different question to everybody else. Everybody else asks, effectively, how do I sell this person a car? How do I make sure they don't walk out without buying a car? I optimize for something completely different. So the question I ask myself is, what can I do now that makes it absolutely certain that they'll come to me when they need to buy their next car? Wow. Typically, if you're watching this and you're running a business with salespeople, what are the symptoms of having problems with salespeople?

3:51What are the things, the tangibles? Well, what you'll be noticing, and you'll spend a lot of time justifying their behavior. and people that hire salespeople justify poor sales behavior because one, they hired them and if you admit that they suck, then you have to admit that you didn't know what you were doing in the first place. So there's a lot of resistance at times. So a lot of excuses can be listened to but you'll know, you'll have salespeople, you're frustrated because they spend most of their time farting about on LinkedIn, social messaging, trying all these different ways of reaching out to people other than picking up the phone or when they finally pick up the phone.

4:24I swear, every time we go into a company, I say, why don't we hit the phones and I just want to hear what you like. Do you know how long it takes from the moment you say that to someone to actually make the first call? Because by the time they slowly walk to their desk, sit down, turn on the computer, load up the CRM, then they start flicking through. No, can't call him. No, can't call him. No, can't call him. And this can go on for 15 minutes. For fuck's sake, just call someone, anyone. I'm not after a meeting. I just want to hear you. So there's a real reluctance to do it. And then when they finally do it, they get stopped by gatekeepers.

4:57They blame the data. The numbers are wrong. The contacts are wrong. Can't get past the gatekeeper. Or I get through to people. They're not interested. They say, send me an email. Our competitors have all this cool collateral, so can we create really cool shit to send? Anything to avoid having a conversation. Yeah? And then maybe they get in front of people. But then you spend your life hoping and quoting. Yeah? And you know that your sales guys, you know a sales meeting's gone badly when they come back. You go, how was it? That was good. Why was it good? Well, you know, they liked us. They asked all the right questions.

5:31Really very interesting. So what's the next step? Well, I now have to go away and put together a proposal or a quote or a document for them. I call it document your stupidity. Yeah, yeah. And then we've got to send it. And then what? Then we wait. What's their budget? I'm not sure, but I think it's around X. How are they going to make the decision? I think. And any time you hear the word I think come out of anybody's mouth, what they're saying is I have no fucking clues and I'm going to make an educated guess. So you think, what the fuck were you doing for the last 90 minutes? Getting your emotional needs met.

6:01Because at least you get to go home tonight and say, look, sweetheart, I haven't sold anything. The kids aren't going to eat this week. But I tell you what, they like me. They really like me. Yeah, so kudos. Yeah, so most are in sales just to get their own needs met. It's never about the money, which is weird, right? They say it's about the money, but actually it's about the validation. It's about getting people say to them, I really like your stuff. You're really cool. I've enjoyed meeting you. Don't have anything for you now. But, you know, you've got your foot in the door. And they live on this hope.

6:30So, yeah. So you'll be experiencing that. Quotes that go nowhere. Proposals that go nowhere. Meetings that get dragged out. Suddenly a decision that was going to happen doesn't happen. And it's always the salesperson's fault for failing to do their job, which is disqualify. So, yeah. So if you're experiencing that, I may be off to help. Or some companies are beyond help. You're just screwed. You've just got to live with it. You're terminally fucked. I love it. Yeah, I know. I'm up front. That's why people hire me. But yeah. Anyway, sorry. But with Cialdini, one of the things you say if you're selling a photocopier is you basically say shortly before the point of sale, you go, look, it is expensive.

7:08But trust me, it's worth it. The admission that, OK, it's not all roses is just fundamentally plausible. follow i think uh dan arieli's point which is give a sign that you're on their side which might be an act of generosity that isn't expected you know that might be the double tree cookie when you check into a double tree hotel hotels aren't obliged to give you a cookie the very fact that the double tree does this spontaneously fundamentally primes you for reciprocation OK, but also establishes trust, which is this is obviously long term relation. Basically, there's relational capitalism and there's transactional capitalism.

7:49Transactional capitalism seeks to maximize the short term value of any transaction, regardless of the value of the relationship down the line. Relational capitalism seeks to maximize the value of the relationship with the customer over time. Economics doesn't understand the distinction between the two. So humans are, I think, always asking the question, is this transactional or is this relational? And if you violate the norms, OK, one of the most fascinating findings from customer satisfaction was that people who've had a problem with a product and yet the problem was very well resolved end up being more loyal to that brand than if the problem didn't occur in the first place.

8:29And economists get really angry about that because they go, well, surely it's better to have a product without a problem than it is to have a product that had a problem, even if the problem was solved. And the argument is no, no, no, no. Because when they called you with a problem, assuming you didn't charge them for solving the problem, your reserves of reciprocation, goodwill and long term investment in the relationship are being tested. And if you solve the problem, okay, then you have proved that you are someone to be relied on because you're actually interested in keeping them as a customer rather than someone who, sorry, your transactional value was six months ago.

9:10Why don't you just piss off? I guess for you, what is your definition of a lead? And then after that, I'd love to know those appointments. How do you run it? I guess from top to bottom, what are you trying to get out of those appointments? so a lead is a strong signal of interest or a detectable signal of interest that doesn't even have to be strong but it's a we can detect a signal of interest so a lead could be that they've liked a social media post through to commenting on a social media post through to filling in an online form engaging within you know i've got my big four lead generators that i use so the number one lead generator is online assessments where people fill in an online assessment to see if they need something assessment based selling or assessment first selling is phenomenal you know I've built most of my businesses off the back of having a really thoughtful assessment where if someone fills in that assessment they're going they're pretty much halfway to going ahead so online assessments are excellent introduction workshops I love intros so registering for an introduction workshop is a lead um i've always for 20 plus years i've had introduction workshops as a cornerstone strategy uh for lead for as for a signal of interest discussion groups where people join a discussion group on facebook or linkedin or whatsapp and they say yes i'd like to join that discussion group um and waiting lists uh waiting lists or expression of interest lists um or the fifth one would be opt in for content so opt in for a report opt in for a video series opt in for some sort of content additional premium content that that you opt in for so any of those kind of big lead generators those those four or five things they are my big go-to lead generators so it's when people engage with one of those those are my pretty warm signals of interest Somebody the other day said 100k a year, and I understand money beliefs, 100k a year is not enough to live on.

11:13And it's like, come on, like, come on. The average is 33k in the UK. There's people that are struggling. They don't need to hear that right now. No, they don't need to hear that. And I get it, you're using it to sell something. What are your, because I would never put you in the category of sales guru. Thank God. Because I have deliberately – it was a conscious decision. You guys know this. But when I started out, I knew I had to break through because sales trainers are a dime a dozen. I needed to stand out. And when I went on LinkedIn to look at what other people in the area were doing, they all fell into the trap that I teach against.

11:57And it's this desire to be loved and liked. and it's reflected in how they would refer to themselves, guru, top performer, number one leader, best performer. And I said, see, they still don't get it. They still want to be loved and they still want to be loved. I said, I don't want to be any of that because that's not going to help me. I want to be – and that's where it – I'll be hated. And so if you go over anything that I've written since 2016 is when I really started using LinkedIn, if you read anything, if you can – if it goes back that far, I don't know, You will never once see me as ever referred to myself in anything as an expert, as a sales leader, as a sales professional.

12:31No, because I don't believe in that. Other people can call me that, and that was the whole strategy. Get other people to say Benjamin's the expert because that's when you are, when other people see it. But if you have to call yourself it, then I'm very skeptical. So going back to the permission-based, look, it's like anything in life. Some things work better than others. a permission-based opener will fail some of the time. Just like a non-permission-based opener will fail some of the times. But what we have to work is we've got to play the odds. We've got to play the statistical averages, right?

13:05And I know statistically that when I do the line that you guys love and everyone seems to do now, you kind of just go, look, I'll be up front and this is a cold call. Do you want to hang up now? Let me have 30 seconds. Statistically, that achieves a far greater carry-on than a lot of others. Now, I'm not saying, I get clients who say, I don't want to say that. So rather than I agree with them, I say, well, I don't care. Don't do it. I don't give a toss. If you don't want to do it, don't do it. But let me ask you this question. If it worked, would you do it? Yes. Then do it. If it doesn't work, don't do it.

13:35But if it doesn't work and it's working for someone else, what's the first question you're going to ask yourself? Why does it work for them? And then you have to look in the mirror and say, well, maybe it's the way I do it. Maybe it's the way I say it. Because if it works, it works. So I don't care how you open a call, though, to be perfectly blunt. Yeah. You know? So these arguments, the other argument all the time is does cold calling work? It's just a load of horseshit. The only people that push that, and they always get, this is, again, no, it's proof of why LinkedIn is just a bit of a cesspit in some ways.

14:07If you write a post that tells people what they want to hear, it does well. Of course. And if you tell people you don't have to prospect and you don't have to cold call and all you need to do is send video emails and do all of this, People love it. But if you say the opposite, you don't get the – but it's fine. Because the people that like your stuff are the people that gauge it. The people that get it and they'll use you. So, yeah. No, LinkedIn, I hate LinkedIn. I can't wait to the day that I don't have to use it. It is my office. Yes. You know, I've been self-employed for 20 years and I love it and I would never work for anyone.

14:40But LinkedIn is the office place for me because every day it's the same people. Yeah. And I didn't choose to work with any of these people. People would be surprised to hear that, I think, that you hate it. Oh, yeah. But like I hate prospecting, but I'm good at it. I use LinkedIn because I'm good at using it. Different people live in different places. If you want to get hold of me, you probably best call me and I'd be like, I'm in that world. I'd love it. But actually, if I receive a cold email and it's like, I saw that you did this when you were 21 and this, I'm a bit like, I get it. But it's like over personalization.

15:12What's your what's the reason behind that? Well, my issue is that my diary is scheduled pretty finely. I've got an assistant who schedules stuff into the diary. There's not a lot of times where I'm happy to take a call. If I have blank free time in my diary, it's because I want free time in my diary. I don't want someone calling during that time. I'm working on something. I'm catching up on something. I don't want an unscheduled call. So I'm always going to have my backup of like, how did you get my number? Why? Like all of that sort of stuff. and uh you know i'll give you an example someone lovely and amazing cold called me the other day while i was loading 10 suitcases i was traveling with my whole family through la and grandma and we had 10 suitcases between our group and i'm just pulling up at la airport and they said have i called you a good time and i said absolutely not if this is a cold call i said i'm literally arriving at LAX and I've got 10 suitcases I've got to get onto the sidewalk and I've got to then drop this car back at the thing this is the worst possible time right and they never call back had they just dropped me a long text I'd read it like they've got my number drop me a freaking text you know I'll read it at some point I'm going to be sitting in the airport like you just happen to get me at the exact wrong time so it there's nothing personal about that it's just if you're calling me cold there's a very very high chance that I'm that it that I'm not sitting around I'm waiting for a call.

16:38This is just a point about the obsession with reducing transaction costs in business strikes me as fundamentally misdirected in that most big brands grow because they sell to a lot of people and those people buy them quite frequently. So it's a mixture of repeat purchase and size of overall market. and what we're doing is we're basically saying let's try and force everybody to transact with us in the lowest cost channel and that strikes me as fundamentally wrong you should actually say we will use whatever media are necessary to acquire and keep a customer and some of them will be more expensive than others but that's simply a product of reality.

17:32That's just how the real world works. There are people who will respond to direct mail and there are people who will respond to email. And yes, okay, the people who respond to email may be slightly cheaper to reach. It is not fair to conflate customer value with cheapness of acquisition. And I'll tell you a wonderful story which illustrates this. A very, very wise person who runs a very successful online travel business. We were sitting in a meeting and the chief executive and founder was just sitting at the end. And somebody said, use the phrase, the need to maximize online conversion from the website.

18:10And the guy just said very shrewdly, he said, hold on on this basis. He said that the typical visitor to our website converts at about 0.8%. The typical person, and he acknowledged the fact we're not comparing like with like here, okay? The typical person who phones us up converts at 35%. Now, he said, I appreciate the fact that people who phone us up are warmer prospects than people who visit the site. Nevertheless, he said, do you really want to hide the phone number on the site to minimize the cost of the call center? because, as you could roughly put it, you know, I'd rather have 90 % of a lot than 100 % of not very much.

18:59What you're doing is you're actually effectively privileging low cost to serve over ultimate value.

From the publisher

In this episode, we break down 20 minutes of the most brutally honest sales advice you'll ever hear from Rory Sutherland, Daniel Priestley, and Benjamin Dennehey, three of the sharpest minds in business, marketing, and sales.

We dive into Daniel's 3000 DM strategy, the exact approach he used to launch Score App without a massive audience, and why cold outreach still beats posting on social media when you're starting from zero. Rory explains the difference between transactional and relational capitalism, why America's most successful car salesman asked a completely different question to everyone else, and how businesses obsessed with short term efficiency gains are destroying long term customer value.

Benjamin reveals why most salespeople are lazy, how to spot the symptoms of a broken sales team, and why sales reps spend more time getting their emotional needs met than actually closing deals. He breaks down the permission based opener that statistically outperforms everything else, why LinkedIn is full of validation seeking gurus, and how to qualify prospects properly instead of living on hope and quotes that go nowhere.

We also discuss the cold calling versus texting debate, why Daniel refuses to take unscheduled calls but will read a long text, and how forcing customers into cheap channels to reduce transaction costs is fundamentally misdirected. Rory shares the online travel business lesson that proves maximizing low cost channels isn't the same as maximizing value, and why customers who complain and get their problem resolved become more loyal than those who never had a problem in the first place.

If you're launching a business without an audience, struggling to get your sales team to perform, or wondering why your outreach isn't converting, this episode will give you the unfiltered strategies that actually work.

Hear more from the Hosts:
Jack https://www.linkedin.com/in/jack-frimston-5010177b/?originalSubdomain=uk
Zac https://www.linkedin.com/in/zac-thompson-33a9a39b/

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