Simon’s interview was tied for the most-used in the book, in no small part because of its eloquence. In addition to stunning content, the delivery makes it all especially compelling. It’s more than enough to let me forgive the lack of credibility he assigns to sales books in this interview.
Simon’s views on sales culture and compensation were instrumental in forming my own business, and this is an interview filled with suitably salient views and stories.
You can read Simon’s full biography here
Jamie: Simon, what have you found most fulfilling about your career thus far?
Simon: I’ve been deeply, deeply blessed because I feel as if I have managed to work with some of the nicest people on the planet. I feel that in my career, I’ve managed to collect and hoard golden souls.
The thing that I have probably enjoyed the most has been seeing youngsters join the company and fulfil their potential. For me, it’s actually a lot more about the people than it is about the products or the profit.
Jamie: Has that always been the case, or has that changed over time?
Simon: Almost by definition, the joy of mentoring comes at a later stage, so yes, it has been a particular pleasure of my twilight corporate years. At the start of my career, I was just thrilled to be earning a living wage. I have also always been excited by abstract ideas and their ability to affect change. It was this which first drew me into finance. I didn’t want to be constrained to what I could achieve with my own hands or just through my own direct personal labour. So, finance interested me because differentiated thinking alone could quickly lead to dramatic and sizeable change. It offered the most efficient leverage against pure thought.
Jamie: That drew you towards building something based on an intangible product rather than something tangible?
Simon: Yes, plus the fact I gave up all real-world-skill learning at a very early age. This might be oversharing, but I was also very interested in securing well-remunerated employment. My dearly beloved father was subprime before it was fashionable, and he went bust twice in my childhood. That gave me a deep and lasting respect for solvency, and I’ve been very committed to its pursuit ever since.
A colleague of mine once referred to his life goal as to be “fabulously solvent”, and I’ve adopted that as my own.
Jamie: Is finance a profession that you can go into and expect solvency, or is that just certain pockets of finance?
Historically and empirically, there has always been a very sporting chance of being overpaid to go into finance versus either the corresponding contribution to society or the actual intellectual sweat and toil required.
For me, however, despite the attractions of a fast track to personal solvency, I always had huge issues with its frequent moral ambiguity. In particular, I had a real problem with the prevailing investment bank culture, which was to blur the line between clients and victims. It might all sound rather sanctimonious, but I knew I had to go a different direction by the time I was 28.
Jamie: Do you see investment banking as still being that way, or do you think it has made fundamental changes?
Simon: I remain deeply sceptical about investment banking. I think they’ve got a lot more careful about being caught. I’m sure they’re trying to rein in some of the worst of the excesses, but it still worries me who they’re solving for. Are they solving for the client? Are they solving for their shareholders? Are they solving for their own pay packets? I’m sure there are some decent, honourable bankers, but I think the whole structure is fraught with inappropriate temptation. I fear that finance remains more of a playground for sinners than for saints.
Jamie: Do you think of yourself as being in sales?
Simon: This will sound like a glib answer, but I think at some level, everybody’s in sales. To give you my own background on sales, to earn extra money when I was going to university I used to do door-to-door selling. I think that experience had a considerably more significant and lasting impression on me than anything I actually learned from my PPE (Politics, Philosophy and Economics) course.
My degree was hugely character-forming: it taught me the life-defining importance of enthusiasm and a Teflon-coated soul.
Jamie: Why did you do-door-to door sales in the first place?
Simon: It was just a way to make money without real-world-skills. I bumped into a fellow student, who has gone on to be a Private Equity legend, and we sold paintings. We started door to door at people’s houses, which is really hardcore and then moved on to offices. Not surprisingly, one could receive extraordinary levels of abuse knocking on people’s doors uninvited. But you couldn’t take any of that the next door you knocked on. You always had to convey the impression that you were truly living your best life. That impression has never left me.
Jamie: Now, in your function as Chairman, as someone who’s leading a business, how do you find that you interact with the sales function?
Simon: We have always taken a deeply contrarian approach to sales, and we’ve done this by design from day zero. When we were just three people in a shed, we toyed with whether we should go down the conventional path of commission-based sales. We knew that we could potentially fund this by making our prices higher because it is an effective way of making sales. Instead, we very deliberately and consciously decided against that path. Our reason for doing this was a fear that commission-based sales would lead to an “us and them” type of culture. More specifically, we were concerned that our content producers would resent the salesforce for potentially understanding the proposition less but earning more. This can very easily discourage the producers from enthusiastically supporting the sales process.
So, we chose the path of lower prices, with no commission-based salespeople, hoping that all colleagues would buy into supporting a sale. Or stated differently, we see everybody’s job as selling the firm, directly or indirectly.
A related obsession was that I always wanted to keep politics out of company life. Politics creeps into things like transfer pricing; sales targets; functional budgets and resources, but most especially it can dominate the allocation of sales-based commissions. We often get teased about having a hippie culture. As with a lot of teasing, however, it reflects at least a partial truth.
This approach should not be confused with any lack of respect for the importance of reward and remuneration. Rather, we have decided to primarily address these issues via our approach to equity participation.
When we set up the company, I started with an 80% stake while my business partner, Guy Ingram, had a 20% stake. That was the high-tide of both of our stakes, and we have been diluting ourselves ever since. We have been making equity, or equity options, available to colleagues ever since after making a proven contribution to the firm. My share has since slipped well below 50%, and I would probably be stripped of my MBA if I had one, but I totally believe that the people who’ve contributed to the firm should participate in the success of that firm. I think that’s both ethically right and good business: it creates the sincerest alignment of interests. I think that the one currency that’s stronger than actual currency is dignity. If you treat people with dignity, they will repay you with trust and patience. With patient, fine-spirited people that trust you, you can change the world.
Jamie: What do you think your sales culture looks like today, and how do you think it compares to other sales functions?
Simon: The people that I think make great salesmen wear their heart on their sleeve. They’re genuinely enthusiastic, they have great interpersonal skills and almost an overdeveloped sense of empathy; I want them to really care about our clients. I actually think that salespeople, more than anyone else, need a sense of team, companionship and to be appreciated. I think there’s a public preconception of salespeople as being quite hard, often self-centred: the lone-wolf. I do not think that we have any salespeople like that.
I think that actually everybody craves applause and appreciation. We try to treasure, nurture and augment that sense of team, that feeling of a shared adventure, fuelled by pride in what we’re doing. Salespeople that you want will feel pain when they lose to a competitor. There’s also a micro-bereavement when they lose a client. As I have mentioned before, I think that all the best salespeople are optimists and enthusiasts. I think that salespeople can also be amongst the most gullible people in the world because they live on an optimistic plane.
We want to create an environment where they are loved, feel loved, support each other, and feel supported by everyone else. I think that this true for everyone but I think that it is particularly true for salespeople!
As I mentioned before, I think everybody needs and craves recognition. When we host events, my advice to my more junior colleagues is that you can always congratulate an industry legend or a multi-billionaire just as they finish giving a speech, and they will appreciate it, as they will crave validation at that precise moment.
Jamie: Have you found that recognition works as well as cash incentives when it comes to recruiting and retaining salespeople?
Simon: Certainly for retaining. I think culture is key to retaining people. For recruiting, I think it is key that you know what you are looking for and give a damn about whether your firm is the right place for the candidate.
I see my role as trying to find, attract and then hoard golden souls. We do not typically do a hard sale on someone thinking of joining us. In keeping with being a hippie cult, we assume that they will find us when they are ready to join the Mothership.
I hope that when someone is thinking of joining our firm, it is not just about the money, or even mostly about the money. We do believe that what we do is good for clients, good for the markets and good for the world. For a candidate to be right for us this would need to matter to them. We need them to care about the “how” and not just the “how much”.
We are fiercely competitive when it comes to our firm’s aspirations, which might be where the hippie commune analogy breaks down a little, it is just that we will not compromise our values to achieve success. We actually see our values as being the most assured route to success, at least in the long term.
Just going back to the sales, it is a job that can easily end up just feeling like a scoreboard. As consultants, we pretty much make an art form out of keeping score because it’s a large part of what we do. A scoring system can clarify what you’re trying to achieve, but it is also fraught with danger if you become a slave to a scoreboard. And the wrong scoreboard can have severe unintended consequences, and it can be torturous for the people who are thus enslaved. Life is a game; you get to play once. You have to enjoy it. You will do your absolute best when each living, waking minute is a thrill. The key test is: do you jump out of bed in the morning? ”
If you’re a slave to a quota then there’ll be times when you’re doing well, and you beat it, and that feels kind of good, but there are also times when it just haunts you. That’s the wrong thing to be haunted by, in my opinion.
Jamie: And did think having an alternate sales culture, where you don’t pay a commission, where it’s all about the team, where equity is the motivator, has that had any impact at all versus competitors in terms of winning business or recruitment?
Simon: That isn’t easy to assess. We created this business without a penny of outside capital. Could we have done better? Maybe. Could we have done it quicker? I don’t know. I’m 100% sure there are a whole lot of people who will not have considered joining us because of our approach. Do I have any regrets about that? I don’t think so.
We’re not the right employer for all people. Our offering is a trust-based service, not a product. To illustrate the importance of trust we go back to the saying: “In the land of the blind, the one-eyed person is king or queen.” The problem with this saying is that if you’re blind, you’ve got no idea who’s got one eye. Your would-be King might be us blind as you are, but just more willing to bullshit than you are.
Our mantra is that the one thing more important than being trusted is to deserve to be trusted, and I think the essence of deserving to be trusted is to truly be yourself.
I know that you are writing a book about “selling”, but to me, that is a bit like a book on “sincerity”, which is close to being an internal contradiction: If you have to read about sincerity in a book then there is a risk that you’re not being completely sincere.
Jamie: So your argument is that sales can’t be learned or is an art, not a science?
Simon: I think that it is mostly a personality type.
I only have one question in interviews: “What’s your passion? What’s your interest?” There is almost no wrong answer to that, but with one exception and that’s when I think that the person is just trying to guess what will impress me.
I’ll give you an example of the worst answer, and one of the best answers I got as well. Once somebody was in from Oxbridge, and they’d been studying history. I’d asked, “which period of history are you most interested or passionate about?” The person said, “Oh, your colleague asked that and I said the Civil War, but now I feel like that was the wrong answer to give.” WRONG answer? This is meant to be what YOU are passionate about!
The best answer I got when I asked somebody’s passion and the answer I got was “I like cooking. I like baking and making cakes.” So, I said, “Oh, that’s interesting – is that because it is a kind of chemistry, and it’s creative?” To which they replied “No, no. I just like to feed people.” They immediately got my vote.
That person did make great cakes too, but it was the calm self-knowledge that impressed me. Hence, for me, learning to be a salesmen feels like something of a contradiction. For me, find yourself, be yourself, be happy with yourself and let yourself find something that suits you.
Jamie: What advice would you give to aspiring salespeople?
I think you have to lock yourself in a dark room, put a moist flannel on your head, and summon up as much candour as they can muster and then ask yourself what scoreboard internally really drives you, and what life adventure you actually want.
A job that you enjoy doesn’t feel like a job and selling something you believe in doesn’t feel like selling.
Every meeting I go into I think that there are two possible outcomes: either they become a client, or they didn’t really understand what I was saying. If they don’t understand what I’m saying, then it’s because I should have said it clearer. I don’t blame them, I blame me. I like to think that I have too much dignity to spend my waking hours and the good years of my life persuading people to do things they shouldn’t do or buy things that they shouldn’t buy.
Jamie: If you had your career again, what would you do differently?
Simon: I was recently asked what was my greatest failure, and I struggled to think of any. This is certainly not because I haven’t had any. I just do not choose to dwell them. The same is true of regrets. I think that I mentioned earlier the need for a Teflon-coated soul. I guess that this is part of what I meant by that.
If I had my career again and I had to be something else, I think I’d like to be either an Estate Agent or a Buddhist monk. I could get passionate about finding the right home for a given buyer, and I am deeply fascinated by the cusp between mindfulness and neuroplasticity.
Jamie: Going back to sales meetings where, as you say, they either buy or they misunderstood, could you give me an example of a time when that didn’t work out, and there’s something you learned from that?
Simon: When I was selling paintings door-to-door, I went to an office, and this guy must have been having a really, really bad day. I started my pitch with, “I’m from Trinity Oxford, and I’ve got these paintings……” and he jumped in with “You’re going to follow me, and I’m going to put you in this room. I’m going to go into another room, and I’m going make two phone calls, and the first phone call is to Trinity College, Oxford, to ask if they have a student called Simon Ruddick. When I hear that they don’t my second phone call is going to be to the police. They’re going to come here and arrest you.” Of course, I was at Trinity Oxford, so when he rang, they simply acknowledged that there was indeed a student called Simon Ruddick. He came back in and went “God, I am so sorry. I will buy every one of your paintings.”
He bought all the paintings that I had with me.
Jamie: Is that story a failure?
Simon: No, you are completely right. It was the biggest sale at that I had ever made at time….and it all came from simply knowing who I really am!
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