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Exit Paradox Podcast Episode Notes
Episode Overview Title: Ben White. 'Dark Decade' After $800M Exit: Addiction, Divorce & Financial Losses Host: Anastasia Koroleva Guest: Ben White Description: Ben White shares his journey through a tumultuous decade following his $800 million exit. This dark period included personal challenges such as divorce and addiction, and financial losses. Despite these struggles, Ben has emerged as a happier person and discusses his insights on happiness, entrepreneurship, and authentic relationships.
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Key Themes and Discussions
- The Impact of the 2008 Exit
- Significant Life Change: Ben sold his company, MessageLabs, during a turbulent time (the day Lehman Brothers collapsed).
- Sudden Loss of Identity: The transition from being an entrepreneur to not having a business left him feeling lost and alone.
- The "Dark Decade"
- Personal Struggles: Post-exit, Ben faced divorce and addiction, leading to a decade of turmoil.
- Coping Mechanisms: He turned to drugs and alcohol, which exacerbated his feelings of loneliness and poor decision-making.
- Lessons on Happiness
- Grounding Oneself: Importance of taking time off to assess life and personal happiness after a major exit.
- Avoiding Materialism: Material purchases, such as homes and cars, do not equate to happiness.
- Value of Relationships: Highlighted the importance of surrounding oneself with genuine friends who challenge and support you.
- Parenting Reflections
- Engagement with Children: Emphasizes the need to be present for children, especially during tough times.
- Teaching Empathy: Discusses how kindness and connections with others lead to personal fulfillment and happiness.
- The Role of Wealth
- Changing Views: Initially, wealth was equated with happiness; however, Ben learned that real fulfillment comes from simplicity and authenticity.
- Legacy and Impact: Focus on leaving a lasting, meaningful legacy rather than just chasing financial success.
- Transitioning Back to Entrepreneurship
- Creation of UP: Transitioned from a VC firm back to entrepreneurship with a new venture focusing on automating paid media for businesses.
- Feeling Alive Again: Ben expresses excitement and fulfillment in his current entrepreneurial journey.
- Importance of Nature and Simple Pleasures
- Connection to Nature: Highlighted how experiences in nature contribute to happiness.
- Appreciating Mundane Moments: Learning to find joy in everyday activities, such as cooking and interacting with family.
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Key Takeaways
- Take Time for Reflection: After a major life event, it’s crucial to pause and reflect to ensure decisions are made mindfully.
- Simplify Life: The fewer moving parts in life, the happier one tends to be.
- Authenticity Over Wealth: Genuine relationships and personal integrity are more valuable than financial success.
- Boredom as a Catalyst: Allowing children to experience boredom is important for creative growth.
- Kindness and Empathy: These are essential for personal satisfaction and should be practiced consistently.
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Final Thoughts Ben White’s journey encapsulates the complexities of life after significant financial success. His experiences serve as a reminder that happiness often lies not in wealth, but in relationships, self-awareness, and a connection to the world around us. The episode concludes with a powerful reflection on the importance of being present, embracing simplicity, and cultivating kindness in both personal and professional spheres.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00Welcome to the Exit Paradox podcast, where we discuss how to build a fulfilling and meaningful life after selling a business. I'm Anastasia Koroleva, an exited founder who spent the last 13 years researching and collecting stories about life after a successful business sale. Don't go and buy lots of stupid things. As I said, do nothing includes buying. You can buy something, but don't change your life. Go and buy an enormous house, a fleet of cars, an airplane, if you've made enough money. That won't make you happy. The less moving parts you have, the simpler your life, generally the happier you'll be and the happier your family will be.
0:40Ben White. He's sold three businesses so far for$80 million,$88 million and$800 million. It was the last exit 16 years ago that hit him hard. What people don't tell you is you have, when you build these businesses, you build your little world where you're respected, where you're developing people and watching them grow. It was a family. And so suddenly your family's gone. And no one to prepare me for that. That day felt like the loneliest day of my life probably. What followed was a dark decade filled with divorce, addiction and significant financial losses. However, today Ben is the happiest he's ever been.
1:23In this episode, we discuss his hard-earned lessons on happiness, why he started his fourth business now and walked away from running his VC firm.
1:39Hi Ben. Hello, good morning. You are unique in so many ways. You had three super successful exits, but I know that it was the last one, which was in 2009, that hit you really hard. It was 2008, actually. Okay. We closed the day Lehman Brothers went bust. Oh, of course you did. Of course, it had to be 2008, of course. So in 2008, which is long ago, which is great, because it means that you had a chance to process the lessons of that. But I also know that you refer to the following 10 years of your life as the dark decade. I would love us to go straight into that, because it would be very helpful for my audience to understand that experience before we start talking about your previous exits or the way you build businesses, because I know that experience changed you quite a bit and the way you look at the world.
2:34So could we go back to that day in 2008? And just tell me to start with how you felt when you sold MessageLabs. So it didn't just change me, it changed my whole life, it changed everything. Or it was the start of the change, if you like. RBR Networks with Rory, my school friend, in 95, 96. And then we grew Star out of RBR Networks and we grew Message Labs out of Star. So Message Labs was the only one that I sold where I didn't have a nascent business that I'd been working on for a while that I could then spin out and start working on. It was the first time since I was a teenager, really, that I didn't have a business that I was working on.
3:22So that had never happened to me before. Yeah, yeah. So that hit you hard, that suddenly you no longer had the business. Why do you think that happened? Well, first of all, I don't think anyone prepares you, right? You've done something, you've obsessed about it day in, day out, all hours for years and decades, in my case. And then suddenly you sign something. And in my case, I'd already left the business. There was a professional CEO in the business, but I was pretty involved. I was speaking to him a lot. And suddenly you've sold it. You've got a huge amount of money in your bank account. And then that's it.
4:02There's like nothing, right? I've got nothing to do at all. At the same time, I was getting my wife and I, probably a lot of it my fault. I'd already made a decision we weren't going to work. So at the same time, we decided to go our separate ways. So I had no business that I was working on. and I was going through a messy divorce. So not a great combination. I can very much relate to it, as you know. I had exactly the same combination. It was my first exit, but also a divorce at the same time. These are two huge changes in life. So, okay, and how did you handle that? Oh, just huge amounts of drugs and alcohol, really, I suppose.
4:47It worked brilliantly. no it was just lonely and horrible it was the fact what people don't tell you is you have when you build these businesses you build your little world that makes sense to you where you're respected where you're you know developing people and watching them grow and it was a family and so suddenly your family's gone and in my and no one had prepared me for that and it felt so to go back to your question that day felt like the loneliest day of my life probably and I would say I filled it with lots of very poorly thought out business decisions or investment decisions that I thought if I invest in this I'll be able to live vicariously through it and I will get that same sense of purpose and anyway that that same feeling would come back if I invested in these businesses.
5:46And I made a lot of poor decisions, partly because I'd never invested in other businesses other than my own. And also, no one prepares you for the fact that you've got, if you've just exited, you're on everyone's list to call if they want to raise money for their new shiny thing. And really, you should spend a year doing nothing, thinking about what you want to do, grounding yourself again, and thinking about what you want to do with the rest of your life with this freedom that you've bought? Do you need to go on working? Do you need to go on making money? Is it making you happy? Am I happy? All the kind of logical questions I didn't ask myself.
6:28Or maybe I did ask myself and I just thought, I'll do it again and then I'll be happy. I'll build a Google and then I'll be happy. Of course. And then now you look back at it and you see a lot of waste, waste of money, waste of energy, waste of health in your case. I wish I could talk to me in November 2008. I wish I could talk to myself then, knowing what I know now, and things would have turned out very differently. Let's do that. You're talking to me, and I'm you back then. What would you tell me? I would say take a year, do absolutely nothing. I would say Ben
7:12we can talk all day long about whether you're an alcoholic a drug addict or whatever actually that doesn't matter what matters is is it materially affecting my life and my happiness yes or no if the answer is yes you need to do a lot less of it or probably none of it and stop doing it I can remember saying to myself well I'm not an alcoholic I don't pick up a bottle of vodka at breakfast and have it with my frosties so I'm fine and I'm sure there are tons of people listening who who who fool themselves in exactly the same way um but whose life is and and whose family not only their life but anyone who comes into contact with them particularly their wife and their children or whatever are whether they like it or not are massively affected by this by this behavior even if it's even if you're doing a half decent job as a parent, you're miles away from being connected to the kids and being present.
8:11Of course. And they can sense that and they can feel that. And it makes them uncomfortable and it makes them feel insecure. And it makes it much less likely they're going to be happy kids. So you would tell me, and now I'm you, back then, to deal with the addiction as the most urgent thing to do. No, I don't want to make too much of the addiction, although that's a massive part of it. You need to deal with this amazing event that has just happened. You need to stop being naive about it. You will be treated differently by some people. Lots of it in a good way, right? But lots of it not in a good way.
8:50People will take advantage of you. And especially if you don't have a next gig or anything to really pour yourself into, you'll probably be fairly gullible. Many of us find it very hard to say no to people like that, and in particular to people who are close to us, family or close friends or partners we feel we owe something to. How did you deal with that, with saying no? I never said no. That was the problem. One of the things that I've learned is if you do great things for someone, whether it's an act of kindness or whether it's helping them out massively financially, don't expect them necessarily to be grateful in the way that you might think they would be because in a way, as time goes on, they resent it.
9:49You've done this thing for them. Perhaps they've been successful themselves. and now it's an inconvenient truth how they got there perhaps that you know because you helped them out in the way that you did so they resent it that's that's their problem of course but it's your problem in terms of how do you deal with that because it doesn't make sense right why are they not grateful i also found for example that giving a loan to someone is always a bad idea in this situation because a if they actually wanted a loan they would be able to get it somewhere else so they're asking for a gift but if you give them a loan when they actually need a gift that destroys the relationships and the formula I came up with years years too late was that you just decide whether I'm I want to give that gift or not without any expectation as you correctly say to get the money back or to get appreciation and gratitude but it's not easy yeah I think you never I mean, you may call it a loan, but never expect it back.
10:51Yeah, but if they know it's a loan, I found that then they resent you even more because then it's very uncomfortable for them. They can't return it. They don't want to return it. You become a creditor instead of a friend or a family member. It changes who you are to them, and that damages the relationship. Unless you're very careful with how you position it, for sure. Yeah. For me, the most important thing is just don't expect it back. Put a red line through it right away. And if it's friends and family, if it's really close friends and family, don't expect them to be grateful for long. Okay, fantastic.
11:30So we have quite a few lessons already. Do nothing for a year. Don't expect gratitude from people. Don't go and buy lots of stupid things. As I said, do nothing includes buying. You can buy something, But don't change your life. Go and buy an enormous house, a fleet of cars, an aeroplane, if you've made enough money. That won't make you happy. The less moving parts you have, the simpler your life, generally the happier you'll be and the happier your family will be. Where's home is a good example for people with multiple homes. That's unsettling for children if they don't even know where home is.
12:12that you're depriving them of the very thing that kids need, which is interaction with other children. But because you're so wealthy and you've got a security detail and this and that, your children are deprived of interactions with other children of the same age. Unless, of course, it's in the confines of some weird security guy sitting in a corner. How strange is that? How many children do you have? Two. When you look back at that dark decade of yours, what would you do differently as a parent? That first year I would have immersed myself in, you know, the one thing that I found as the kids are now 16 and 18, it's that they've just finished GCSEs and A-levels.
12:57And I found when things are tough and when things aren't quite working out at any aspect of my life, immersing yourself in children is an amazing tonic because you have to be present they don't care about your problems and it's a wonderful antidote to problems it's a wonderful way to make yourself feel peaceful and complete if only I'd known that but I didn't have the time I wasn't in the right headspace to do that anxiety I had a lot of anxiety caused by drugs and alcohol, but I also had... Yeah, and therefore I wasn't present. And then the kids didn't, as a result, they wouldn't really engage.
13:45There are lots of people who wonder, why weren't my kids engaged? They weren't engaged. You can't just pick one morning and go, right, I'm going to be a great dad. It takes months for them to know you're there, you're consistent, you're always available, little by little by little. They'll let you enter their weird little world. You need to build that trust for them to open to you emotionally. Yeah. I remember with my eldest, this is back just when I'd just stopped drinking, so five years ago. I'm sure he won't mind me saying, if we had something happen in the kitchen, he threw a plate, it smashed.
14:19I didn't lose my temper. He went to his room, and I went and sat. There's a baseball glove, you know, like a giant baseball glove, which is a seat. And I sat on that, and I had a packet of peanuts, and I said, I'm not angry. I just wanted to understand what happened then nothing and then I threw a peanut at him and I said I'm going to throw a peanut every 60 seconds until you give me something 45 minutes later and a bag of peanuts and he goes it was I can't say the reason but this was the reason I go and he said that's all you're getting today and then little by little by little you get let in and it's the same with friends they've got to feel that you're in it with them they've got to feel that you're supportive they've got to feel that you care what triggered your decision to address your addiction?
15:09I think my fucking life was a car crash it just suddenly became obvious I looked at my youngest son who was very ill with anorexia and bulimia at that time he weighed 29 kilos so I looked at myself and the impact I was having on him and just thought I'm not happy right I just whatever happened whether it's rehab or whatever I do I need to give someone the keys to my life for a couple of months go away switch off think about what I want and come back with a plan as to how to be I had how to be happy actually because if I'm happy I'll probably be a decent dad and a decent mate it was the first time I'd given someone the keys and said right and then you know what you're eating every day you know what meetings you have to go to someone else's in charge.
15:57I loved it. No one can call you, text you. You're just left with your own thoughts. So that one stay dealt with it or was there more? No, that was it. That was it. For anything you're doing in your life, it's about a decision. And when you've made the decision, it's much easier, whether it's smoking, drinking, whatever it might be. It's a lot easier. What I've noticed is that sometimes people almost want someone else to make the decision for them and I see it in relationships between you know these people and coaches therapists rehabs doctors trying to delegate a difficult difficult decision so did you seek any professional help for other health mental health issues like you mentioned the anxiety for example I was so caught up in you know held by this addiction and constant you know you're constantly hung over or trying to feel better or you might you know in my case I might not even drink for a week a month so I thought I'm fine but you don't realize but then you're doing a two or three day bender and that takes a lot of time especially as you get older to get to get out of your system so you're permanently anxious so you're trapped by in this cycle um and and so no amount of therapy would have helped me at that time unless that therapy had got me to put my everything down and go and take two months to think you know to get to get all of the crap out of my system all of the alcohol all of the drugs all of the coffee all of this all of that so your body has a chance to recover because your brain's a muscle right and if you're permanently pummeling it and abusing it it'll it'll start playing tricks on you there's a reason for that anxiety they didn't just didn't just happen and i think they they'll treat it with a pill or whatever but actually there's probably something there and very often something that they're doing or drinking or snorting yeah but they've thought oh i don't do it very much that's not it's fine but it's not fine yeah i think sometimes it's not even about substances but it's about not addressing something that's important i think anxiety exists for a reason.
18:17Our nature gave it to us for a reason, I'm sure, as everything else. We need it because when we were animals, we need that anxiety. Otherwise, we wouldn't get up and feed ourselves. Exactly. When I look back at my life and I had periods of extreme anxiety, now looking back, I know that I had been delaying some decision or I delayed understanding something. So now I'm trying to be a bit better at respecting these moments of stress and anxiety to try to follow it and see what it is my body, my brain is trying to tell me that I need to address and I'm ignoring it or I'm not being honest with me about some circumstances.
18:55Or maybe you accept the anxiety at that time because you go, actually, I've got that A, B, C and D. I'm bound to feel a bit anxious right now. That's okay. That's all right. Yeah, I guess if you come to the conclusion, it's part of your personality. anyone gets anxious right depending on I don't know it can happen in any situation getting all the kids to school they're all late they've lost something their cricket bat whatever and you're anxious like I'm not gonna make one of them's got to get a train the other one's getting driven of course you get anxious yeah I guess these are more like everyday stresses right and anxiety is more to me something that wouldn't let you sleep at night or just makes you But don't the everyday stresses feed into the anxieties?
19:42Yeah, probably. So you said you would take a whole year to do nothing but figure out what this newly found freedom actually means to you. So you didn't do it back then. You were busy doing other things. But have you had a chance to do it later? Yes. I'm a late starter. I'm 56 years old. It does take me a while. I've never been happier than I am today. And it's just all the little things. Do you know what I mean? Actually, like I talked about, whether it's the children, cooking something for yourself, preparing stuff for yourself, picking strawberries, going to the butchers, picking the meat that you want to eat that night, or the fish or whatever.
20:22I think it's all these little things that seemed so mundane to me at the time. Actually, are the richness of life, and they're what balance you. But I assume that it only became nourishing when you learned to appreciate them. Yeah. And stopped looking at them as annoying chores and actually welcomed them as experiences in your life. Yeah, like coming out of the shower yesterday morning. I know there was a towel where the kids have all come in, they've all had a shower and just taken all the towels away. And of course, I get out of the shower, no towel. and um so i have to anyway like lucky old me i've got to go naked to the cupboard clubs i've got a big house i've got to go all the way to my big cupboard and come back oh poor me right i i i'm feeling pissed off i think why are you pissed off you know because you've got a big house and the cupboards miles away with the towels in or because you've got kids that are all happy hanging out showering in your bathroom and wanting to be part of your life what exactly are you pissed off about oh nothing actually would you have it any other way no I wouldn't actually it's lovely I'll laugh about this tomorrow which I am now yeah so you basically trained yourself to have a different mindset and reaction to situations like this and you wish you would have done it in that year after the exit and would have saved a decade of your life for whatever reason it has got me to this point where I've never been happier more grateful just feeling fulfilled how did you get there so one thing you learn to appreciate the mundane things in life what else you would say go and spend time with your real friends not your business friends that you've made who have all become potentially you know will be very successful like you or whatever but the friends from school who will say ben actually you're being a bit of a dick can we just go to a normal restaurant with normal people and normal food, not some fancy place, you know, and have a normal conversation and just hang out.
22:33Yeah. So you didn't realize that you were kind of avoiding something that would be very nourishing for your soul? Yeah, 100%. Because you thought you needed to do what instead at that time? I was searching for that security that I'd had for those two decades of building those businesses. I was someone I had, you know, life made sense to me at that time. And I was trying to make life make sense to me again. So by investing in other silly businesses. Can we talk a bit more about that? Why that was the case? How it felt for you after you lost those businesses that you also lost that sense of security?
23:17Well, you don't know. You drive into work or you get the tube or whatever and you go there and your receptor says, Morning, Ben. You've got that lovely sense of everything works. It's I'm known. I know them. They know me. I've worked with them for a very long time. I feel I belong. I feel I've got purpose. I think they respect me. You know, you've got all of that and suddenly you just, it's gone. And that's removed. and for anyone to think that that's not going to have a very profound effect on how you think and feel you'll be that's a bad error you are it's gonna it's gonna have a massive impact on you and you will fill it with something yeah it's a question of what you fill it with yeah no absolutely and yeah I bet you if you interviewed a hundred founders who'd had successful exits they would all tell a very similar story yeah if you like so so when you mentioned that you invested into all of those silly businesses they weren't all silly businesses you understand there were there were lots of there was there were some deep decent decisions but there were an awful lot of bad decisions as well yeah the way i just understood you is that what you regret is where these decisions came from that they didn't necessarily come from the right place because you actually were looking to restore that comfort zone, that security.
24:48Yeah, I wasn't doing it for a commercial return. I was doing it to make myself feel better because I thought that I would belong again. I didn't even know that at the time, but that was what was behind that. This is exactly what happened to me, so I very much understand it. But it took me years to understand that I was looking for that belonging again. Another part of it was identity. I didn't want to admit to myself at the time that I really suffered from not having a clear identity that I could kind of, a label even, that I could put on myself. I felt kicked out of the ecosystem where I belong.
25:24It is your identity if you do it. So I would love to hear how you now, looking back, feel about the loss of identity at the time. If I was talking to myself then, I'd go, it's okay to feel weird. It's fine. You're finishing one book, but you're picking another up. And for anyone that reads regularly, you know that feeling at the end of the book, and you go, oh, I'm feeling a bit down a bit, until you find another book. And you might find several other books before you find one you really like. It's okay to feel a bit shit and a bit weird and a bit lost for a while, but take ownership of that vacuum and decide what to do with it.
26:05So how would you go about it differently in addition to what you've mentioned before. I just want to make sure I extract all lessons from you. Well, the first thing, you can't pick your new book up unless you're centred. And you can't be centred if you're doing too much of anything, whether it be sex, drugs, alcohol, whatever you need to be centred, or mixing with a lot of people, and I mean people who get big exits, especially my business friends in America, if you're starting to hang out with billionaires, that's weird. If that's now your life, that's a very weird, myopic, not a good representation of people more generally.
26:53These people have nobody saying no to them. They start to believe their own bullshit. and generally how many friends do they have that were friends when they're at school or university? Probably not many, right? So that's probably not a healthy group for you to hang out in. But did you, talking about that, because you went back to having real friends quite a few times in our conversation, So didn't you find that those old friends also changed the way they talked to you after they knew that your financial situation changed dramatically? A bit. How did you deal with that? My real friends, no. They were still, they were, Ben, you're being a dick.
27:43Why? Could be anything. They were still authentic. but I should have seen these friends on their terms not on my boat, on my plane I was starting to stack the cards in my favour so I could basically behave the way that I wanted because they had to so I would have kept it much lower key if I had paid for a holiday for them I would have paid for a half decent villa somewhere not in a fancy pants area where everyone felt more comfortable. Where I'd have probably got a more genuine response from them. So how do you go about it now? In terms of when you think about your social circle, whom do you want to see there?
28:29In the five years since I stopped drinking, I've worked pretty hard. I've worked incredibly hard on my family. And I've got a small number of very close friends. And also we've had COVID and stuff, and it just hasn't been a very social time. What is your criteria for what you want to keep in your life and what you want to remove from it? Keep? Just my dogs, really. But, you know, the less stuff you can have, the better, basically. Because the kids fucking hate it. They come down and go, Dad, who's this? I mean, my children are permanently taking a piss. Can you not do that yourself? But recently I was called a domestic weapon.
29:12apart from my cooking's got to improve and my ironing shit but the fact that they watch me struggling to do it even if i fuck it up is brilliant you know how many friends i've got who every half term and every holiday their kids are off they're off to another fancy place but they're never allowed to be sat at home bored so again when i say simplifying your life that it means holidays it means everything yeah really i love that you mentioned boredom why do you think it's important kids get bored because that's where creativity comes from right you have to be bored from time to time it's important yeah and all we do is fucking over stimulate them continually yeah and you i mean and for ourselves right we can't we can't sit on our own can we yeah i mean i i don't use social media really um because it's just you can't help it can you it's like i'll stop it uh and then of course another addiction yeah and then of course anything you do look at you get fed more of um and and that's happening to every one of us all over the world and whatever views opinions or how we feel it's just getting reinforced reinforced reinforced even if that's only the view of a very small minority we think it's not and i think we'll look back at it as the kind of cancer of our generation because again i think nature created us in such a way that we copy other people's behavior because we are tribal animals so lots of that copying happens very subconsciously so we look at social networks we see all these people and we don't filter them in terms of whom we want to copy yeah for children it's even harder but it's also extremely hard for the adults so for example what i noticed in the post exit founder community is that lots of people keep copying each other's mistakes so they look at what other exited founders do within the first few years pretty much everyone does the same thing it's angel investing or starting a new business and they just do the same thing because that's considered the right thing to do and often it's not conscious there's not much original thinking anymore and that's the problem with AI as well it's just reinforced it's just you know anything we do is just reinforced yeah and the social media actually shows us more of what we like to see.
31:35So we end up not seeing the other side of the story. And you know, you and I talked about it before, you actually need to go at great lengths to hear the other side of an argument, because it will not come to you naturally. Even newspapers are clickbait now, aren't they? So journalism used to be a bastion of people would die trying to write the truth. They may be left-leaning or right-leaning, but they wanted to print it. Is that true anymore? No, absolutely. So going back to your life, because that's what we are focusing on today. At some point, you and your brother together created a venture capital firm after your third exit.
32:15So tell me why and where it is today. So this is a great example of I should have taken the year off. I didn't really think about it. The guys wanted to do it. and the idea was that we could have much more of a work-life balance as a venture we could take August off you know what as they all do but that's not criticism it's fine but that's what they do and I thought that I could live vicariously through these investments and sit on lots of boards and help them and blah blah blah none of that is true right you can't help them you're not in it you're not in the tent you can introduce them to the to some helpful contacts you can nudge them so they don't come off at the faster bends but that's it they're going to do it with or without you you know you're not going to be the reason they're successful or they fail you know that successful founders will find a way to be successful um and and it won't be because they've been on some course run by some venture capital firm on relative successful SaaS metrics.
33:31You don't need to look at a firm to know whether it's successful or not. Do you have customers? Is the margin decent? Are the customers happy? Are they going to stay with you? And have you got a decent sized market? And are you able to build a pipeline with a relatively modest sum of money that you convert over a period of time and if you pour money in the top of your machine roughly what comes out the other end it's no more complicated than that is it yeah common sense is the most important thing in business yeah yeah you know you don't need to look at all the metrics it's obvious i was the founding money of the venture firm 70 percent of it came from me or whatever what i hadn't considered i've made a lot more money than my team um who worked for me And they were all very wealthy in their own right, but nothing like as wealthy as I was.
34:18So I didn't need to work. They did if they wanted to live in Notting Hill and continue to do the whole thing, as it were. I also hadn't expected what it would feel like not to be their boss. And I also hadn't thought about the sorts of behaviours that I might see coming from them. The greed. once that you know we sold the business for was a little under a billion dollars and I saw behaviors from some of them that I'd never seen before of greed and horrible and that I started to see that and I'd never seen that from any of them a bit but but not quite and that and I'd start I started to become uncomfortable at that point like what give me an example illustration we sold the company and like like all these exits you've probably got one or two percent of unallocated share options someone said to me well let's just split them between you and i ben and i said but what about people who were unfortunate with the last grant or whatever let's go through the 700 people and work out who was unfortunate why do we need to do that we don't need them anymore.
35:30Right, okay. That kind of horribly egregious, you know, self-indulgent behavior. When we started the venture business in 2009, we decided to concentrate on B2B and software as a service. And it's hard then because the cloud hadn't really quite happened. And everyone, when we were raising money, people went, Ben, it's very niche, this B2B cloud thing. and I was like what I should have done which I wanted to do on several occasions is bugger off for five years and say I'll come back when it's a thing and so I went from in some ways having had this amazing sale to running around with my bucket trying to raise money for my new thing and people so it's like I suddenly felt oh god this doesn't feel great and we just didn't at the early stages we didn't find many interesting companies to be honest it was quite early for us I think it's not not to say that people that do them are bad people or anything like that just wasn't me no absolutely because you're probably much more of a builder and operator right than an investor but you have a brother and that brother built message labs together with you and then you guys both started the venture capital firm together why do you think it worked for him but it didn't work for you.
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36:55He loves sitting down, he loves shows, meeting new people. And the only new people I wanted to meet were potential customers or potential employees, anyone else I'm not interested, or I'll spend the time with my family. And he likes that. He likes going to shows, he likes going around the world, meeting other members of the venture community. Can you quickly tell my audience what Up is and how you came to the decision to start a new company after trying to be a VC? Because you're basically an entrepreneur who became an investor and then went back to become an entrepreneur. So one of the businesses I invested in, I met a 26-year-old guy called Drew Smith, ridiculously bright, slightly socially awkward, but a brilliant brain.
37:47and he's only got better at the time and I've now known him six years and together we were you know I was selling the business that he was currently working for and he came to me and said look I've got an idea for a new thing so when you sold it maybe you could take the money you sell it for and put it into my new thing so I got him to pitch it to me and I kind of knew what it was going to be I'd already told him I want to be in the intelligence business and data business. This is going back four or five years, so before AI had become the buzzword. And we quickly worked out that paid media, so in other words, so paid media would drive 80 % of Google meta being TikTok's revenue, it's all paid media.
38:37If it's shopping, it's on Google, it's the carousel that you're in when you're searching for a product. If it's a form fill, it's a you need to try to give you a form fill um if it's true you know holidays we've all done searches for holidays and you've been pointed to you know there are the uh one of 20 holiday firms that will advertise extensively um and paid media drives about 20 of all e-commerce sales is driven by paid media sometimes up to 50 so if you turn over 100 million as a retailer you're probably spending 10 million between Google and Meta every year, 10 million pounds. So they're in essentially your new landlord, if you like.
39:22That's quite complicated driving paid media because you essentially take in all of your 10 ,000 products and deciding which ones to spend most money on that might sell. And they currently do that manually, basically. And because they do it manually, it's very hard to look at all the data they should look at when they're doing this. And so Drew's idea that we evolved together was, what if we were to automate, drive paid media in an automated fashion? We could, by doing that, machines can look at far more data in real time than people ever can. Also, if you automated tons of disparate activities, once you've automated them, you can then have them all connected to one outcome.
40:15It might be, I'm prepared to spend£30 for every new customer. I want to make a minimum of 20 % contribution on every pound of sales that I do, or whatever. But if all these activities are disparate, it's very hard to connect them all to one North Star. By automating something, you align all of these activities, connect them to a North Star, and you drive an infinitely better result for whoever you're doing that for. And we're just at the beginning of that journey, basically. How do you feel about the whole thing and being an operator again? Alive. Alive. I think it's sometimes alive and scared, sometimes alive and excited, but never alive and bored.
41:03How much do you work? 50, 60 hours a week. so would it be comparable to how much you worked on your previous businesses harder you work hard enough yeah interesting obviously those first but it doesn't bother you no no I love it because most people and you mentioned you were there as well when we sell our businesses the first idea is that oh my god it was so hard I want to do something that's easier which is why so many people are pushed into more passive investments. We don't want to go through the pain again. But now you've embraced that pain. Why? I'm a man, so I've never had a child. That's not possible yet.
41:48And I'm sure if you asked a young mother one year in, or sorry, six months after the birth, and you said, we're having another child. Never again. but two years on the little person is running around and and you're there you know it's lovely and they're having getting joy out of it and they think life's amazing they go should we have another one right um and of course you get you go on and have another child and i think building businesses is a bit like that you remember all the good stuff um and that's why you and when it works It's just, it's the best. There's no better drug. You know, when you go and speak to a customer and they go, do you know what, Ben?
42:36You know, all of the machine learning and AI stuff, I've been reading about it all. I've bought lots of it in the past. Almost none of it worked. I pay you whatever it is, 50 grand a year. And by the way, I get 10 times that back in value. That's my dopamine. Of course. I was just about to ask you about dopamine and adrenaline addiction, which you probably have. but embrace. So that's my dopamine. They go, you know, wow, we've got something. They're getting value from it. We're making money out of it. People who are building it and writing the software can see that people are using it. So that's great.
43:14And it's a very special feeling. Does it give you a sense of purpose? Yeah. Yeah, but I'm more balanced now. I have both. I have home and work. So home's tick at the moment. touching wood and work if I get the opportunity for up to be it's got the potential to be the biggest business I've touched and I hope it'll be us yeah sounds like you're in a good place also also personally because you you know what you're doing in terms of the skills but you also seem to be in a much better place in terms of quality of your decisions we mentioned that earlier right after you exit your quality of decisions was very poor but now it's different because you're in a different place this time it's going to be interesting you feel every speed bump you're not drinking, you're not taking any drugs
44:07you feel everything whether that is good or bad I guess you could psychologically escape I'm being a bit childish
44:18and I can't wait for that feeling as it starts to scale feeling all of it if you know what I mean and reading the room whether it be a room full of customers a room full of you know employees who are going fuck this is actually working this is going to be a really big company he's not mad he said this would happen and it is happening yeah so you invest in your own money in it yes and some other people as well we've got West Coast investors so let's talk about how your view on wealth changed over time. If we go back to the very first business you started, how important money or financial freedom was for you at the time?
45:06Not at all. I just wanted to find... Well, actually, I just wanted a job. No one would employ me because I didn't have any A-levels or a degree or anything. And in truth, I just wanted to make enough money to pay my golf club membership buy a half decent bottle of wine on a Friday and take a girlfriend out for dinner and not embarrass myself I think when you're young, dumb and full of cum you think I'm going to make when I make tons of money of course I will be happy because you only need to look at the pictures of people with money they're all happy right? of course they're not but um when i started out i didn't it wasn't about money it was just about having a purpose having a business that made money to be honest and going fuck i found something i can do actually yeah um and it was only once i got into it i thought well this is fun i'm quite good at this um wow this hang on this this actually could be a properly grown-up business.
46:18I hadn't even considered that that was possible. I remember there weren't loads of role models and loads of you know, there had been bugger exits in software at that point. You know, in the mid to late 90s, it just wasn't a thing. And then you suddenly becomes obviously, you suddenly cross the line of I'm not just doing this to pay the bills and buy a half-dise and bottle of wine on Friday. I could, we could sell this for a lot of money. And so your psychology changes. You move from one person to another or one mindset, it's probably better, to another. And you get the copies of the Country Life and Fast Car Magazines or whatever it is because you start changing because you suddenly know this might be possible.
47:10and you're still loving the business but your expectation is changing without you even knowing it and you're suddenly going from shit i'm going to be in all likelihood i'm going to be someone worth many millions of pounds or many tens of millions of pounds um and then without knowing it you the people around you are changing their how they talk to you how um they react to you you're someone you've got status um and you don't even know this is all happening around you it's happening without you knowing it um and you're changing as a result even if you're not very careful you change completely um then in my case you sell one business and then you double down going away i'm going to sell one for 80 million i'm going to sell one for 800 million and you keep doing it and and then suddenly without knowing it in my case you're on a right well i need to keep doing it because every time i do it i i'll have more money and i'll be happier uh i sold the biggest one for a little over 800 million that suddenly that became i realized well hang on that's this isn't true ben you don't every time you make more money you don't get happier that's not it's not a binary outcome um and i don't think a lot of people ever go through that realization maybe they you know have a new wife or husband they start mixing with new people holidaying in all the inverted commas right places upgrading their friends trying to go to all the there's a there's a circuit isn't there in london in new york starting with the met gala and they're on that and getting invited to fundraisers and your whole life has completely changed and become the one thing it doesn't have is authenticity and it's not grounded in anything it's not real with my children I would argue that a lot of people say don't spoil them I think that misses the point really to spoil children and it's, are they real?
49:30Because we all spoil our children compared to someone in other countries and other parts of the world. We're all spoiling them to a greater or lesser extent. It's a question of, are they real? Do they get it? Do they understand where the UK sits in terms of fortunate to be just in this country compared to other countries? Are they fortunate to have the chances that they have? And even if they do go on a fancy holiday or a fancy restaurant, they're real. They go, I'm fortunate to be going here. And that's what I mean by real. And I hope mine are real. And that's as a result of doing full circle over the last 10 or 12 years on going, right, so all of this money is great, but I'd stopped being real for a while, I think.
50:21Yeah. And I think I've gone back to be Ben again and being real. so what role does wealth play today in your life how do you see it is it it purely pays the bills that's it and when up is successful i hope it'll be the most successful one i've ever done i want to use that money and do something interesting with it i don't know what because there's no point in thinking about doing something when you don't know how much money you've got and you don't know if you're going to have a big slug of money again. But I, yeah, I would do something real with it, basically. I'm not sure what that is. Probably involve children.
51:07Yeah, but I guess building a useful, valuable business is real because you're giving value to the world yes but I would have done it four times at that and I'll be whatever close to 60 or beyond 69 probably don't I wouldn't do it again I think I've had a good run at that I'd like to leave behind something which is more of a legacy and also something that my children could maybe get involved in in to a greater or lesser extent because the challenge for kids who have very wealthy parents is how do because you can't hide it right you can't it's there yeah even if they're never gonna get their hands on the capital they're still gonna have some of the trappings he can so they've got something to some sort of whether it's a charity of foundation a thing which is great you know then that's maybe something they could do so what do you do to help them move in that direction if that's what you want i i think you're doing it all the time it's not one thing it's it's little things you go into a garage and they'll see me uh and i will always try and make the person working behind the till laugh i'll do something stupid and and they've they've learned that i said because that person's probably not having much fun you could be the bright spot of their day and that will make you feel good and her or him feel good
52:43just interacting with the world around us at every possible given every opportunity an old lady walking across the road that needs help someone's dropped a bag in Sainsbury's and needs it picking up all these little things these interactions that we all used to do 30, 40 years ago as a matter of course but now we've become more and more disconnected that's the irony right, we're in a more disconnected world than ever and therefore those soft that lovely all those lovely interactions that used to happen don't happen anymore and so that's a massive part of our self which doesn't develop kindness, empathy in every aspect of what we do.
53:30And that kindness and that empathy makes you happy. Yeah. And people miss the point. It's not just for who you're doing it for, it's for you. Definitely. Yeah. You could argue kindness and empathy is quite selfish because it makes me feel good. Do you see what I mean? Yeah, absolutely. And you don't have to... I think we miss the point with all the... the way that we're being told to and we're being forced to speak to each other in a certain way. But what these minority groups miss is if someone has a different opinion to them, they're not allowed to have that in today's world, right? So I want you to be open to all of these things going on, but I'm not going to be open to you because if you don't want to change and you're not interested, I hate you.
54:19If you behave in a certain way, that's how you influence your children best, right? They watch you. They learn, right? didn't yeah they just learn they pick it up if you keep doing it and keep doing it when do you think you you realize that kindness and compassion are the sources of happiness more than what you used to think i wasn't unkind but it wasn't it wasn't as front and center you didn't connect kindness and happiness right because you you said you connected money and happiness yeah a little bit yeah so when did you connect back reconnect reconnect yeah probably five years ago I've never been as happy as I am today and it's no coincidence that's one of the things and when your children watch the happy, kind, empathy they pick up on it they become little people with that built in and programmed it and they become happy and that's what keeps them real because they know the real source of happiness Yeah, you put that well.
55:27And I think that's what we miss as a society today. So when I went off on my rant, rather than trying to tell people the way to speak to each other, we're treating the symptom, not the cause. Symptom is we should be kind, thoughtful to everybody. We shouldn't be told to be to a specific group or minority. It should just be a default, right? And that's what we need to change, go back to. Maybe, we'll see. or we're just not going in the street line? We are very resilient as a species. And we tend to pull back from the abyss, don't we? Just when it looks like there's no way back, we pull back. We've certainly done it before.
56:05Yeah. I keep digging into your wisdom. So you talked about how enjoying little mundane, simple things in life, appreciating them makes you happy. Are we missing any other important sources of happiness? Nature. nature nature you know you can't look at isn't this the best time of year in the in the west in the northern hemisphere rather you know it's just june july when everything's green and you look out it's not as grim or whatever um particularly if you're in the countryside that maybe you just it's hard not to smile you know what i mean especially if you've got a couple of dogs doing stupid things and then you're watching other people enjoying it it's amazing it's just such a simple thing the other thing I've done since I've stopped since I've been a bit more available I've found people I used to work with coming back to me and saying just lately actually saying Ben you've got me to do stuff and I I know that I did you know on reflection that I've probably got a hundred letters that I've collected over the last 30 years some big some small but yeah so having that impact on on the people helping them achieve more of who they can be people have much have much more capability than they realize they can go further than they think it's often their own anxiety around failing maybe did you achieve that by pushing them hard or by inspiring them or both?
57:45If you inspire them, you don't need to push them. They'll push themselves. How did you do it and how it changed over time? Did you always have this? I think I've always had that. I've always been very lucky. I've always had that. I've always been able to sell a vision, a dream, an idea and get people excited about it and get people to
58:07rally behind that and come play on my team. You didn't need to be too pushy, nasty. No, I was never like that. You mentioned legacy before. How do you want to be remembered? As someone who was part of the first wave of software entrepreneurs in Europe,
58:34and very successful in that area that paved the road for future generations. Someone who did it the right way, right, who wasn't a dick. They were kind and empathetic, inspirational,
58:57and got more out of people than they ever thought was possible. I want to be remembered for also for making a lot of people a lot of money which I have I like the fact that whether it's friends or investors, whatever, I've made a lot of people a lot of money or share options, I don't know there are 30 or 40 people who've made several million quid because of me, I like that and I want to be remembered as a good friend and a good dad basically I think. Brilliant. How's that sound? If you don't mind, I want to quickly go all the way back and ask you, what do you think your parents did right to help you get where you are today?
59:46And maybe what they did wrong. I think they provided a happy, loving home to nurture three children in. Dad gave me a lot of... Dad is very competitive. He's 86. He's still very competitive. He did the other day. He showed me his new LinkedIn profile. I said, right, why do you... He said, well, I'm thinking of starting again. I said, what, you're 80? Right, okay. Anyway, the profile's good. day so um he said to me once we had an offer for the company for a couple hundred million and i said i'm going to take it i've had enough he said you can't do that i said why is that he said because that's an insult to all the people who haven't been lucky enough to get to this place that you've got to and you owe it to them to make the most of the opportunity that you have now now actually the the deal fell through and we ended up selling it for four times that but that was his mindset.
1:00:48You're lucky to be in that position. Because generationally he wasn't about being happy, fulfilled and content. He was about making the most of everything that you have and all the opportunities that come at the expense of whatever. Because I think that's the way that generation were wired. It doesn't make him a bad person. That's just who he was. You seem to combine contentment and drive, entrepreneurial drive, quite well. How do you reconcile them? Sometimes they're not good bedfellows. Yeah, that's why I wonder how you reconcile them. How do you put them in bed together? I mix them up. Doesn't matter how much money I make, I won't get this time back.
1:01:36So I wrestle with that a bit. But I think I do an okay job balancing it. It's interesting because I expected a different answer. I thought you would say that you're content with what you have financially and materially, but your drive comes from the desire to feel alive and hating. No, no, you'd be wrong. I lost a huge percentage of everything that I made. Yeah, which is, you and I talked about it before. I need to top up. It's a very common situation. I'm not doing this particular one. So you feel hungry now financially? Yeah. Oh, interesting. Yeah, yeah. Because I wanted to ask you about that, because just to continue our separate conversation, that my observation is that it's almost impossible to find a successful exited founder who wouldn't go down financially before going up, if they ever go up or stabilize.
1:02:31And that is what happened to you. And you're saying now you're back to the situation when you're actually driven by money. Yeah, well, yeah, I mean, not entirely by money, but it would be nice if something worked, otherwise my lifestyle probably can't continue as it is. Yeah, interesting. So, yeah, it's the first time that I've had a little bit of financial drive. It was before that. That was number two or three on the list of why I was doing things. This time it's probably more front and center. But that's fascinating. Why do you think that happened? Why did you lose so much of your exit wealth?
1:03:07the average founders lost 50 percent of their net worth five seven years after and there's a simple reason for that in their business they know everything about it there's nothing they don't know they it might appear to people they're shooting from the hip they're not that that idea has been synthesized distilled you know to death and they and they they might so the decision was quick but it was quick because they've already thought about it they've given it lots of thought and they know more about their space than anybody on the planet probably. So they can afford to make decisions really quickly and they're probably largely right.
1:03:43They go, they sell that business and they carry on behaving in the same way. The only difference is these are areas where they know fuck all about and they have far less data, yet they continue to shoot from the hip and guess what they miss. So you think that happens in both investing and starting a new business? 100%. Were your mistakes, if you can call them, or wrong decisions financially, more in investing or because you were too generous with your own business? Both. Both? Both, yeah, yeah, yeah. You need to give a business the right amount of money at the right time. So you didn't do that as much?
1:04:28No, I fell in love with the businesses that I invested in. And then I thought that they would, I kept thinking they're almost there. And the truth is I've never been as successful in anyone else's business as I have in my own. It's extremely rare that a true entrepreneur, especially a creative type, becomes a successful investor. These are such different personalities. Completely different. Completely different, yeah. I believe that 100%. did it affect your decision to go back to business after you've tried to invest in yeah i failed dismally and i thought i better get back to doing what i do best how come you dropped out of school i didn't drop out of school they they they removed me i was it was forced dropout yeah oh i mean i you know i i'm sure today i would be dyslexic and and in those days they didn't get it.
1:05:27And so I'd rather be a fucking pain in the ass. When did it happen? How old were you? 16, 17. Before your GCSEs? Yeah. So the age of your younger son? Yes, exactly that, yeah. But I think probably because I didn't go down the academic route, I didn't have all that creativity wrung out of me. Do you know what I mean? I was still childlike. And I think you have to be quite childlike to start. You see the world through those wonderful, naive eyes. And if you lose that, you're probably unlikely to be a founder anymore. And do you think the education system gets it out of you? That's one philosophy, yeah.
1:06:10I don't know, I never went through it. True. Would you support if your sons decided to drop out of school and not go to university? to um only if they couldn't because i think it's different today i think also they've had covid so their friendship group's much smaller than it would normally be um i think it's been with my kids live in a bubble within a bubble within a bubble if they just if they go well so i said what's your other plan then if you're not going to what's your plan b in those days it didn't matter if you didn't have a degree really people not many people did but now it's expected and but most importantly i think it's a stepping stone to the outside world you know you've never had to share a loo a shower i mean all this live they've always lived life on their terms so they go to uni and live in halls and suddenly they've got to live it's not on their terms so it's a it's a step towards um independence whereas they just leave home go fucking hell that's a bit of a shock isn't it so i think you'll meet i think they will meet lots of new friends that will be friends for life very important and they will build up a whole new level of confidence as a result of this completion of their character because they've had to suddenly life's not on their terms they have to share a loo do the washing pay, the council tax all that kind of crap that will complete them as a little person It didn't happen to you though No You found a different way to complete yourself I did, yeah But at what cost?
1:07:45just because maybe if I'd gone down a different route, I would have got happier quicker. Ben, thank you so much. Okay. I so much enjoyed the conversation. Good to say that I.
From the publisher
Ben White. He's sold three businesses so far for $80M, $88M and $800M.
It was the last exit 16 years ago that hit him hard.
What followed was a dark decade filled with divorce, addiction and significant financial losses. However, today Ben is the happiest he's ever been.
In this episode we discuss his hard-earned lessons on happiness, why he started his fourth business now and walked away from running his VC firm.
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00:00 - Introduction
01:33 - The impact of the 2008 exit and the dark decade
03:10 - Initial feelings and challenges post-exit
05:32 - Divorce and addiction struggles
07:51 - The sudden change in life without a business to run
09:55 - Coping mechanisms and poor investment decisions
11:57 - The importance of grounding oneself after a major life change
14:02 - Reflections on making poor decisions and facing addiction
16:10 - The importance of dealing with significant life events
18:08 - Advice to the younger self: taking time off and dealing with addictions
19:53 - The impact of personal struggles on family
21:54 - Strategies for being present and engaging with children
24:02 - The role of family in finding happiness
26:02 - Recognizing the importance of real friends and authentic relationships
28:20 - The danger of wealth changing social dynamics
30:25 - The importance of staying grounded and real
32:23 - Transition from VC firm back to entrepreneurship
34:20 - The creation of UP and its vision
36:19 - The importance of having a clear purpose and passion for work
38:21 - Changes in views on wealth and financial freedom
40:35 - The role of money in achieving happiness
42:22 - Learning to appreciate simple pleasures in life
44:12 - Finding happiness in nature and everyday moments
46:26 - Teaching kindness and empathy to children
48:29 - The role of nature in achieving a balanced and happy life
50:25 - The desire to leave a meaningful legacy
52:26 - The importance of helping others and making a positive impact
54:33 - Reflections on how to be remembered
56:29 - Parenting strategies and guiding children towards real values
58:28 - The importance of independence and real-world experiences for children
01:01:04 - Balancing drive and contentment in personal and professional life
01:03:26 - The journey to finding personal happiness
01:05:20 - Combining contentment with entrepreneurial drive
01:07:30 - Final thoughts on balancing life, work, and happiness




