Alex Macdonald. A $300M Exit is No Reason to Retire

18 Feb 2025 · 1 h 35 min

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Exit Paradox Podcast Episode Notes

Episode Title

Alex Macdonald. A $300M Exit is No Reason to Retire

Host

Anastasia Koroleva

Guest

Alex Macdonald

Date

[Insert Date Here]

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Episode Summary In this episode, Anastasia Koroleva interviews Alex Macdonald, a founder who sold his company, Velocity Black, for $300 million. Rather than retiring or taking a break, Alex jumped immediately into a new entrepreneurial venture, SQL. He shares his reasons for avoiding a post-exit crisis, discusses the importance of maintaining a sense of purpose, and provides insights into his new business's mission and structure.

Key Themes

  • Post-Exit Challenges: Many entrepreneurs struggle with identity and purpose after selling their businesses, often leading to an existential crisis. Alex’s approach to avoid this pitfall was to keep himself engaged in building something new immediately after his exit.
  • Building SQL: Alex emphasizes the lessons learned from his previous entrepreneurial experiences while establishing his new venture, SQL, positioned as a tech-first platform focused on high-net-worth individuals.
  • Personal Fulfillment vs. Happiness: Alex discusses how he seeks fulfillment through struggle and creation rather than chasing happiness, drawing a distinction between the two.
  • Community and Relationships: The episode touches upon the importance of community and meaningful relationships, both in personal and professional contexts.

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Detailed Notes

  1. Introduction
  2. Host's Background: Anastasia shares her experience of navigating life after a business exit and introduces Alex.
  3. Guest's Background: Alex sold Velocity Black, a digital concierge service, and discusses the company's journey and his motivations for starting a new venture post-exit.
  1. Avoiding Existential Crisis
  2. Alex chose to start SQL immediately after his exit to avoid the void many founders experience post-sale.
  3. Quote: "I think honestly, if I had had that void... it probably would have not led to a productive use of my energy."
  4. Key Insight: Staying active in entrepreneurship can provide fulfillment and purpose.
  1. Velocity Black Journey
  2. Company Overview: Initially a mobile payment service that pivoted to a digital concierge.
  3. Growth: Rapid expansion and a successful pivot led to a lucrative acquisition by Capital One.
  4. Challenges Faced: Operational intensity and stress during the company's growth phases.
  1. Transition to SQL
  2. Business Concept: SQL aims to connect high-net-worth individuals with promising investment opportunities while providing educational resources to make informed decisions.
  3. Focus on Education: Emphasizes the importance of empowering clients with knowledge about investing and entrepreneurship.
  1. Fulfillment vs. Happiness
  2. Alex articulates his belief that fulfillment comes from struggle and challenge, not from the pursuit of happiness.
  3. Quote: "Fulfillment comes through struggle... it comes through trying things which are risky."
  4. Critique of Happiness Culture: Expresses skepticism towards the societal obsession with happiness, advocating instead for a focus on meaningful engagement.
  1. Community and Social Life
  2. Alex reflects on his social life, noting a small circle of close friends and the importance of maintaining meaningful connections amidst professional commitments.
  3. He shares experiences of adventure and personal growth that contribute to his overall fulfillment.
  1. Angel Investing Experience
  2. Personal History: Alex discusses his journey in angel investing, shifting from an analytical approach to valuing founder qualities.
  3. SQL's Unique Proposition: SQL aims to leverage the influence of high-profile investors (like athletes) to enhance investment opportunities and outcomes for startups.
  1. Legacy and Impact
  2. Long-term Vision: Alex expresses a desire to be remembered for kindness and contributing positively to society.
  3. Quote: "I want to be remembered as a very kind person who would always help his friends... helping mankind."
  1. Closing Thoughts
  2. Alex reflects on the importance of being true to one's nature as a creator and the role of supportive partners in fostering creativity within entrepreneurial ventures.

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Key Takeaways

  • Staying Engaged: Post-exit engagement in new projects can prevent the existential crises many founders face.
  • Pursuit of Fulfillment: Focus on fulfillment through challenge rather than the elusive goal of happiness.
  • Community: Maintaining meaningful personal and professional relationships enhances well-being.
  • Education for Investors: Empowering individuals with knowledge about investing can lead to better decision-making and outcomes.

Final Thoughts The conversation offers valuable insights into the journey of entrepreneurship after an exit, emphasizing the significance of purpose, community, and personal growth as foundational elements for sustained fulfillment.

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Transcript

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0:01The world doesn't need lots more investors, to be honest. There's no shortage of capital really. There's a real shortage of talented people to go out and build stuff. Willing to work very hard to create value for sure. So what would you do if you sold your company for$300 million? Retire? Explore the world? Do all these other things you had no time to do while building a business? Well, this is not what my friend Alex McDonald did when he sold his company Velocity Black two years ago. In fact, Alex made it quite impossible for himself to have any kind of post-exit sabbatical. That is what you got fulfillment through is probably building something, right?

0:44You're likely to get that fulfillment if you do it again. And the second time around, you can do it in a different way, right? It happens all the time. And also, you're absolutely right about the danger of being stuck in this limbo for a very long time. Maybe just having a holiday for a few months is a better way of doing that and then starting again. That's exactly the conclusion I came to. In this episode, we're going to explore why he made this decision and how he applies the lessons from his first full entrepreneurial cycle to building his new business, appropriately called SIGPOL.

1:25Hi, Alex. Thank you for coming. Thank you for having me, finally. You know, you and I met, if you remember, on the day when the news about your exit leaked. I do remember, yeah. And we had lunch with 14 other post-exit founders. And our mutual friend Timo Armour put you on the spot and said, oh, he sold the company today. He should pay for lunch for everyone. That's how I met you. Yeah, he did. He did. That was the day that the news leaked. Exactly. It was yet complete, right? So we were a bit, I mean, we were a bit upset that it leaked. But obviously, once Timo did that and put me on the spot, I had to actually pay for lunch.

2:09You can't. I know. That was your first post-exit investment. There we go, yeah. But yeah, no, it was an interesting, look, you know, mixed feelings about everyone knowing. But yeah, it was a very intense period, obviously, trying to get the actual transaction closed. I remember you looked a bit confused because you probably yourself didn't quite fully realize that you no longer owned the company and a new chapter started. I want us to focus on what happened since in this interview. But before we go there, tell me about Velocity Black, the company you actually sold on that day. Yeah, so we started Velocity Black, which was originally called Velocity, at least the company was called Velocity, in 2014.

3:01It was my very first business, so I was a first-time founder. I'd previously worked in turnaround, so managing distressed companies, but decided I wanted to build something myself. had seen you know companies like Airbnb and Uber rising at the time and thought it was an interesting opportunity to build something in the mobile space and I phoned the smartest person I knew from school back from when I was in school and convinced him to quit his job at Goldman Sachs and come and join me and we started Velocity in 2014 and our first product was actually around mobile payments so we did we were one of the first companies where you could see the bill on your phone in a restaurant and get up and leave pay on your phone and get up and leave whenever you want without waiting for the bill right which is something which will split the bill with your friends which is something which a lot of people can identify with right no one likes waiting for the bill in restaurants it was quite a popular idea investors could easily understand it customers could easily understand it and we raised quite a lot of venture capital for that initial idea quite quickly raised close to$20 million within a year and a half and grew it quite rapidly from the UK into the US and Canada.

4:17But it was a terrible business, terrible in economics. And so we had this sort of moment after 18, 24 months where me and Zia, we just closed our Series B. we were sat in in a glass I still remember the exact room this glass room in our office in Soho um thinking you know being having the most money we'd ever had in the history of the company's existence sitting in the bank account but also being the most stressed we'd ever been because we were like this business doesn't work we're gonna have to change um and so we did quite a hard pivot to velocity black which was uh which still is a digital concierge so if you think about the traditional concierge services like quintessentially or amex centurion um you know where they have people sitting in call centers sort of answering calls and you have a personal lifestyle manager our plan was to digitize that put that into an app um and then enhance it with artificial intelligence, make it much more, firstly, much more efficient to run as a business, but secondly, a much better customer experience.

5:28And this is before AI was cool. Yeah, exactly. I was just about to say it. Unfortunately. That time. So we would have been able to raise a lot more money. But this is way before AI was cool, but we were using sort of natural language processing, basically, rather than large language models to do a lot of automation in that space. And the pivot was successful, right? We already had like good relationships with the restaurants from our first business and so it was a question of adding travel experiences luxury goods and then you know obviously kind of perfecting the actual digital product to make it work properly but yeah very quickly grew to sort of millions of dollars in revenue and so we knew um at that point we actually had a business which was good um and it had great unit unit economics right so we had really good sort of cact ltv ratios and we had really happy customers and yeah we then went on to grow that business we did raise a bit more capital after the pivot but the new business was very capital efficient had a great working capital cycle right people paying annual memberships up front and then transacting through the platform as well so we didn't actually need to raise a lot more a lot more at least equity capital to raise a bit more debt and continued growing that for five or six years.

6:47We launched, so we had the private client side, Velocity Black, where we had our own brand, direct to consumer. And then we had an enterprise side where we would white label the technology and the product for basically any premium or luxury brand that was looking to build stronger relationships with their clients. So people like Rolls-Royce. So Rolls-Royce have an app called Whispers. So if you buy a Rolls Royce car, you get access to the app called Whispers, which had a concierge's part of it, which was Velocity Black, basically. And we did that with banks, credit card companies. And so it's kind of like an enterprise arm of the business.

7:25And, yeah, we grew successfully both the private client side and the enterprise side. And then eventually one of the enterprise clients who we were forming a partnership with, Capital One, you know, started saying they were interested in investing in us. But we didn't need any money. So we said no. And then it gradually led to ultimately them making an offer to acquire us and a bit of back and forth negotiating. And eventually we came to an agreement and sold the company to Capital One. And they're still managing the product. But the product is still live under the Velocity Black brand. And I know they've got some exciting plans to launch some new Capital One products using the technology that we had.

8:08So I look forward to seeing those come out. So it definitely sounds like a very exciting business. So why did you start another one before you sold it? Because that's one of the things we talked about. That's one of the things that makes you very unusual for my podcast. because you actually had another business already at the time that you sold the first one. Yeah, so let me say this. There was some overlap, right? And I ran Velocity Black. I was co-founder and COO for eight years. And roughly two months before we got the acquisition offer, I told the board I wanted to step back to be chairman to start a new company which is Sequel and I didn't know we were going to have an offer but and the reason I thought that was the right time to step back to start this new company is because the company was doing better than it ever had been you know we'd got through COVID successfully the business was you know growing revenue strongly whilst generating strong positive cash flow it wasn't profitable but positive cash flow strong positive cash flow the team were happy we had a great management team in place I felt I was the first time I could actually do that um and uh and then just by luck we had an offer come through right which we accepted now you know did I did I even pause to think at that point in time oh should I should I continue and go and launch this new business or should I take a break and you know take some time off no I didn't um and um I don't you know I often I often and thought to myself, should I have done that?

9:53Should I have taken like six months off? Ultimately, I don't think I should have. And I've got, you know, some of the people who've been on your previous podcast, I know very well, as well as some of my friends who've exited businesses. You know, I typically find they go into this kind of, which is a lot of what this podcast is about. They go through this kind of existential crisis, right? After they have an exit, right? And I think, honestly, if I had had that void and the time to even think about all that stuff, it probably would have not led to productive uses of my energy, let me put it that way.

10:34I probably would have got bad habits. I probably would have got used to an unhealthy kind of lifestyle, which ultimately wouldn't have led me. I'm not sure I'd say I search for happiness, but I search for fulfillment. and I'm not sure I would have felt very fulfilled if I had taken that break. So I'm actually very happy that I had something immediately to jump into which gave, you know, where I could invest all my time and energy and hopefully now some of my own financial resources rather than having to go and raise lots of money from lots of other people. And yeah, that's led to me, you know, not having to go through that kind of challenging period that I see a lot of my friends go through where they're like questioning their identity and everything and for most of them you know and put it this way you know that velocity black journey was very tough you know we've kind of skated over it but there was some really really tough passes a very operationally intense business right we had the most demanding clients in the world it's 24 7 365 it's unsociable times it's you know there's a big human team young all around the world and so it's an always-on business literally always on as in you know occasionally having to wait well waking up I'd say two or three times a week in the middle of the night to deal with a crisis right and for eight years so I think a lot of my friends they kind of go through that particularly their first-time founders and they exit they go through that very intense period and then they're like I need to I need a break um which is understandable but really what they need to do is build something again right particularly if they're a founder yeah and and that's what you know um I think is quite I'm you know we don't the world doesn't need lots more investors to be honest right and um you know as much as anyone says there's you know challenges around fundraising in my view and I think all the data shows there's no shortage of capital really there's a real shortage of talented people to go out and build stuff right willing to work very hard to create value for sure exactly and I think if you are if you are a founder and you've had some success with your first journey you know that is what you got fulfillment through is probably building something right you're likely to get that fulfillment if you do it again and the second time around you can do it in a different way right firstly you've learned a lot of lessons right and you've made a lot of mistakes that you hopefully won't repeat again you probably have some resource now to do it in a slightly different way which may be less stressful right and maybe you don't want to go down this sort of venture capital building a 10 billion dollar business next right but um i feel like most people a lot of founders because their personality types they kind of think oh I built this now I'm going to go spend some time thinking about all these other things I can do right and they go you know do I start buying cash flowing businesses do I do pretty much everyone does the same they go through the same journey of exploring all these different things right and um and and by the way from the outside all those other things look easier right but as you know the closer you get to them the harder you understand you know the more expertise you need right so so ultimately I think the ones that end up most fulfilled come to the end of that sort of six or twelve month or some cases multi-year period of kind of exploring stuff and they they go back to actually I'm just going to found another company and start building something Alex we talked about my interview with Corey Jensen exactly that story he tried everything and then at the end of the day what makes him happy building a business again there we go It happens all the time.

14:23And also you're absolutely right about the danger of being stuck in this limbo for a very long time. Because some people relax too much and then they create whole systems around a beautiful lifestyle. And then it's very hard to pull yourself out of that. Even if you feel this need for purpose in your life, it's still very hard. Absolutely, yeah. And I think, look, some of them have genuine PTSD from their first companies. I think I do. I think a lot of founders do. And they feel like they have to escape it. And I can understand that. But maybe just having a holiday for a few months is a better way of doing that.

15:00And then starting again. That's exactly the conclusion I came to. Because there is this optimal time to start a new business. Probably ideally, it's good to have a break. Because most people are very tired. You're saying you are not that tired, surprisingly. But lots of people are really exhausted. So it's good to have a bit of a break, but then it's so dangerous to get stuck either in decision paralysis or trying all these different things one after another just because others do. Yeah. You're absolutely right. But for me, it's also very interesting because you didn't have any break at all. And you worked extremely hard for eight years.

15:39So how about just physically recovering? Did you do that? Yeah. Look, I think firstly, so with Velocity Black, we were still operating when COVID hit, right? And I was still full-time in the business when COVID hit. And that was a very challenging time for the business, right? So we had, you know, travel was our main source of revenue, right, out of the different categories. So, you know, engagement sort of plunged, I'd say, very aggressively in the first sort of couple of months of COVID. thankfully it recovered very quickly and we pivoted some of our services to deal with that and eventually you know we ended the year flat which I think is better than most other startups in that space but the one positive thing I'd say about COVID after I got through that initial very stressful few weeks where we had to like restructure the team like do all these you know changes to the business we went fully remote and that was when I realized how unhealthy I was right so um so I did it enabled me to invest some more time even whilst running the business full time and actually you know going to the gym eating properly um doing those kind of things um and so by the time we got to the sale I was still doing a lot of that stuff and we were still fully remote um and so that I think that helped uh well firstly it helped during the sale process which was also very stressful um and yeah look I think I was in a you know it wasn't like I came to after I'd sold the company I was like oh phew now I can focus on my health I'd already been doing it for a couple years it was really thanks to COVID that I've been able to do that right because yeah I think if I hadn't I'd have still been going into the office for 80 hours a week right which is what I was doing before so so um so yeah I think that that definitely helped and uh and look i continue to invest some more in my health since then since we since we exited but but yeah thankfully i had the wake-up call and the opportunity with what covet and sort of remote working forced me to think more about health at some point a few months ago we talked about this and you mentioned that you actually approach your work life balance differently with sql your new company comparing to Velocity.

18:00So tell me about that. Yeah, look, I think certainly, and by the way, there's no like right answer to this stuff, right? The right answer for someone at a certain point in time in terms of their life stage, you know, their age, whatever, is not going to be the right answer for someone else, right? But in terms of what was, you know, where I was at with Velocity Black, like let's talk about the period pre-COVID, right? I mean, all I knew was from a diet perspective was like Deliveroo and then eating out, doing lots of like client entertaining and eating out in restaurants all the time. And don't get me wrong, there were nice restaurants, but it was not a healthy diet.

18:41From an exercise point of view, it was like minimal exercise, right? And, you know, it's one of the real lessons that I've, you know, come to learn is I'm a completely different person if I exercise once a day. I make much better decisions. And aside from just being healthier, like mentally, that is what, like, exercise is my therapy, right? And so... Same here. And so if I do that, I'm in a much better mood. I'll make better decisions. The company will run better. And so, yeah, look, I went through a few years at Velocity Black where it was just very intense and sometimes where I didn't leave the office, right, for a couple of days.

19:21So I'd be... And, like, when we were hiring lots of people and it was, you know, we had engagement skyrocketing and we literally didn't have enough team members to deal with the demand that we had. Those were very intense times and I became very unhealthy. You know, if I was to rewind, would I do it differently? Probably not for that point in time, right? Okay. Because I genuinely think the company would have failed if I didn't do it, right? Wow. Now, I have changed what I do now, right? and you know I prioritize doing some exercise every day ahead of everything else right and that's like blocked out my diary it doesn't change right and nothing will come up literally unless I have to take my wife to the hospital to stop that right so so yeah I think that's the one main change is I prioritized exercise certainly first of all and then diet and sleep afterwards ahead of everything else.

20:20And then hopefully that will enable me to make better decisions, right? But at that point in time, you know, would I go back and change my habits? I'm not sure, you know. I just feel like if I had taken a different approach at that point in time, because, you know, me and Zia didn't have lots of financial resources. You know, the company was kind of surviving, right? And, you know, so you're kind of investing everything into the business and you're worried that if you don't, that it might fail right in a couple of months so um so I'm not sure I would change that as I said I think there's a right answer for you at whatever stage you're at in your life and whatever stage your company's at right like there may be times at Sequel where I'm gonna have to you know be in the office for 20 hours I don't know it hasn't come up yet but there may be some time where I have to do that and maybe that's a short period of time where I'm doing that but certainly for now I'm absolutely prioritizing things like exercise and stuff ahead of it because hopefully that will lead me to making better decisions.

21:17But do you think this happening, this is happening at the expense of the company? Or it's actually good for the company? I think it's good for the company, yeah, for sure. That you're more stable and you're taking care of yourself better. Yeah, for sure. And look, you know, that there's, I think with Velocity, me and Zia were still having to do a lot of, we're having to do everything, right? And really, as a CEO, So, you know, quality of decision making is the most important thing. And at Sequel, I'm still doing some of the things. I do a lot of our content and I speak to a lot of our clients.

21:54I still do sales calls, so to speak. We don't call them sales calls, but I speak to a lot of our clients. I organize some of our events and things myself. But most of the things I do and the highest leverage things I do are obviously making decisions. right and um those the quality of those decisions are much more impactful than you know me doing a particular piece of content or me hosting a particular event or me doing a particular sales course so if i'm healthy and if i'm in a you know in the right space mentally those quality of decisions should be much higher right and therefore the business should do much better so generally yes the bit that you know i'd say the business should be much better off if you're prioritizing your health first yeah so um i noticed that lots of people who sell their businesses then look at the next business very differently some look at the new business as sort of a lifestyle thing to stay busy and not necessarily as driven or working very hard and other people try to be very rational about it and they plan for an exit to happen as soon as possible.

23:11Which group you belong to or are you in the third group altogether? Yeah, I'd say neither of those groups. I'd say what I'm trying to do, what we're trying to do with SQL. So, you know, in the long run, we're building a next generation Goldman Sachs, right? So we're focused on high influence, high net worth individuals, people who can bring more than capital to the underlying assets. And we're creating a tech-first platform to engage with those clients and enable them to invest. And eventually, we will do some wealth management through the platform as well for them. But for now, it's just we're connecting them with individual investment opportunities and our first asset class is venture.

23:49So in the long run, this is an ambitious project, right? It's not a lifestyle business. And I believe it can be a$10 billion plus business one day.

24:00I am doing it differently to how we did Velocity Black. you know i have not raised i've raised from some friends and family but that's mainly to keep me accountable and on track um most of the capital in the business has come for myself and that will continue to be the case until it becomes so big that that's no longer possible but um but yeah most of the business the capital for business come for myself and i've you know i see this i see us as having certainly a 10 billion dollar opportunity here you know a typical venture timeline for building that might be 10 years and I don't have a an aggressively short timeline like that like for me I see this as being like a 15 to 20 year journey um we're dealing with clients who you know that they're very influential very wealthy and therefore it's a very high trust business right and I think taking a venture approach to trying to scale that too quickly will lead to failure and will lead to mistakes.

24:59And it's very hard to build trust with this kind of client and it's very easy to lose it. And so our approach is, you know, not to go and raise hundreds of millions and pump loads of money and grow this as quickly as possible with a big risk that it fails. It's to take it a bit more slowly, build trust and build products based off our client needs and build trust over time and hopefully do it in a more capital efficient way right and in a lower risk way right where there's a much lower risk that the company fails because we're you know we're not you know foie grasing the the the company with capital yeah you're much more careful and you actually listen you focus on your customer rather than the abc investor who is pushing you to do something and i wouldn't say like i'd also say i'm not working towards an exit with this right like i i have like obviously i want to provide liquidity for my team and for the friends and family that did invest in the business right at some point in time there are lots of ways to do that um so i'm not working towards a particular exit i think to get to the business that i envision right now in terms of the opportunity i think is like a 15 year journey right um at least and we'll see what happens after that but i i don't there's no like plan to kind of build and sell and i know we have some friends some mutual friends who literally just think of things that way.

26:21Exactly. And there's nothing wrong with that. That's great. And I'm invested in some of those companies as well, right? It's not bad to be an investor in one of those. No, there we go. Yeah. And look, you know, and again, so yeah, so we're neither a lifestyle business. We're neither like build to sell. I'm trying to build something impactful, which I think will be a generational brand one day. And it's going to take longer because we're not going to do it by raising hundreds of millions of dollars of venture capital. And, but importantly, the second, I guess, kind of related to that point, you know, one thing I've noticed with founders who exit their business, there's like kind of, there's two extremes, right?

27:03And I've seen some founders who've exited their business for very significant sums of money. They might have 50, 100 million dollars in their bank account. And they start the next business and they go out and raise lots of money from other people, which I find interesting. and then you have like kind of the opposite end of the scale which is like elon musk right selling paypal and putting all the proceeds into spacex and tesla right and i'm definitely more towards the elon end of that scale right um probably not on iq but certainly in terms of risk appetite so and you know i i personally believe like if you're an exit founder and you believe what you want to do firstly if you actually believe in it you're probably going to be a little bit greedy right and want to keep more of the company for yourself right and um and uh and secondly yeah i just um i find it strange to kind of i i there's a lot of dissonance in the fact that someone's got a lot of money personally but they're raising money from other people i i personally can't get my head around that but i i'm not saying either one is wrong but um but yeah that's the other thing i found with post-ex like there's a lot of those those two groups basically there's the ones who kind of do that for me.

28:12They use their success to leverage their kind of personal brand to go and raise money from other people. And then there's those who kind of invest their own capital in the business because they want to keep more of it to themselves and grow it themselves. You know, since I look a lot at people who existed long ago, I try to zoom out and see like, you know, their stories 10, 15, 20 years later. I have to say that there is a danger there in that path. And the danger is that people put their money in. They believe in the business exactly as you said. They feel it's natural. I mean, I actually did that as well.

28:48But then they run out of motivation. Yes. And then they keep throwing good money after bed. They can't really raise money and don't want to because they lost motivation in the business. And I think this managing your motivation is extremely important and people don't expect this to happen at all because at first you have this momentum carrying you. yes right but then oftentimes it's not there anymore because financial hunger is gone and people are not sure what should motivate me now yes so have you thought about it do you feel anything like that happening i um i think i'm motivated by building right so um i as long as you know I'd say look I'm I'm most interested when there's a lot of innovation happening and when there's a lot of okay you know we're going to try and launch a new product so we're going to try and incorporate a new technology into what we're doing to kind of you know change the business right like I thrive in I guess chaotic or changing circumstances right I like I like a bit of chaos because there's opportunities in chaos to improve things or change things.

30:02And so I think as long as there is that, and by the way, I think businesses today need to embrace chaos and adaptability more than ever before, right? And the evidence for that is the average age of a company in the S &P 500 is getting shorter and shorter. The average lifespan of a country in the S &P 500 is getting shorter and shorter, right because they're getting disrupted so you need to embrace change and you need to be constantly adapting your product if you want to be successful and as we're seeing at the moment with AI right AI is going to kill a lot of huge huge companies um so so yeah as long as I think I have that right and I'm not just some figurehead overseeing a machine with you know everything is predictable and repeatable processes and not much is changing, as long as I have that, I think I will always have motivation.

30:59So a$300 million exit is not the reason to stop working for you. No, no. And, yeah, look, you know, it's obviously very easy for people to say this after they've had an exit, right? Everyone always says, oh, it's not about the money after the exit, right? Yeah, of course, yeah. like and I think that's a bit disingenuous right because honestly when I was 25 I would like that was all a lot of what I was thinking about right and what I was working towards right so um so yeah look it's a bit disingenuous to say that but honestly um again I'll go back to that point around seeking fulfillment rather than happiness right like people have this you know there's an obsession with like today's society around seeking happiness and being happy yeah I don't think it's healthy yeah um I think you know if if you're going to be if you if you're going to describe yourself as happy happy is just a relative feeling right and if if what you're searching for is happiness then there must be unhappiness right at the opposite end of the scale and so the people who are constantly searching for happiness typically they're very unhappy a lot of the time as well and so I try and look for fulfillment and you know and fulfillment comes through struggle right it comes through trying things which are risky which you may fail at right you may fail at something and you may feel a bit of disappointment and you have to learn from that and kind of you know go on to the next stage and and then when you succeed it's really fulfilling right um and And whether you'd equate that to happiness is another question.

32:44But for me, that's kind of what I seek. And if I were to stop working after selling a company, you know, and go on this kind of journey of seeking happiness, the people who I've seen do that, who've sold companies, have ended up very unhappy. Right. Or they've retired too early. Yeah. you know, they get drawn into probably quite an unhealthy lifestyle, even if they're, you know, excluding like alcohol or drugs or anything, even, you know, just not having a structure around your day and, you know, people who are reliant on you and people you are accountable to just makes, I think people lose their way, their brains slow down, right?

33:33You typically see this with people when they retire in old age, right? Their brains immediately slow down and people say it's the start of them dying, right? And yeah, and so for me, given I'd seen some of my friends go through that, I thought I definitely don't want that to be me. And financially, I'll be fine for the rest of my life for sure. um so well unless you know we have world war three or something or the dollar breaks down but um I should be fine and so really it's about like you know having some fulfillment you know I don't yet have kids but I do want to have kids and I think one of the only reasons I've been successful is my mom sent me and my dad sent me a very good example of being very hard working and you know I want to set a good example for my kids I want to be fulfilled in what I'm doing on a daily basis I want to build things and so yeah there was never a question that I was going to stop working or retiring after the set of a company, however much I sold it for.

34:34So for you, it's about your love for challenge and building. I think so. And that's where you find fulfillment. That's where I find fulfillment. You know, I found also that lots of exited founders actually have very healthy lifestyles. Sometimes you would say even extremely healthy. They go into biohacking and they want to optimize themselves. You know, this whole obsession with longevity, you know, in our communities, it's very common. It is. But I think in this case, there's a different problem there, that people become so self-centered, so self-obsessed, that they're doing everything for themselves.

35:08But when we're very selfish, we are never fulfilled. Because when we're building a business, whether we realize it or not, we're creating something for others. And it's our customers, but it's also our employees, right? We have this sense of purpose and sense of duty and sense of meaning of giving something to the world. and sense of community yeah and sense of community too a community where you you have meaning right you mean something don't just define some of those people as being very unhealthy honestly you know and i i mean like spiritually unhealthy i mean you know we can talk about brian johnson but like you know um and he's almost starting what i'd call a religion a modern religion with what he's doing with blueprint so there's some element of community and what he's doing.

35:59But you can see, I don't know if you've watched the documentary that just came out on Netflix about him. It's definitely worth watching. There is a sense of loneliness in his life, for sure. And lack of, you know, he's completely obsessed with this. And to be honest, he's making a lot of sacrifices, I guess, for the wider world, right? By testing all this stuff. But there's definitely a sense of loneliness there.

36:26And yeah, And like some of these founders, yeah, who like are very, you know, do all the right longevity things. They have 80 supplements they take per day. They have every hyperbaric chamber and red light therapy machines in the house or whatever. It's all great. But they, for me, those people are unlikely to be fulfilled. You know, I think one of the big, you know, big lessons that, well, peer reviewed research shows this. even brian johnson says this right and he's come to recognize it it's one of the i think stark things that he comes he kind of comes to inclusion in this documentary about is the people who live longest are the ones who have the most connections with other people right and community is so important to driving to basically having a reason to live and feeling fulfilled right yeah but the reason to live usually comes with you giving to that community right if You sit in the middle of that community and just receive.

37:23You have to have responsibility and accountability. You will not be fulfilled either. Absolutely, yeah. So, yeah, I describe some of those people as being unhealthy from that perspective. Alex, you mentioned religion. Can we go into the idea of starting a new religion? We can talk about it briefly. Yeah, look, this is not a short-term thing. but you know I think one of the sad things if you look at the breakdown of religion in most of the western world right as in you know there are more you know there's growing atheism and pretty much every western democracy certainly and I think that has had a lot of negative impacts on society as a whole right and um you know if you think about people used to go to church every week right whatever church that was right you know whether it was synagogue whether it's catholic church anglican church but you know uh all the different types of churches and at that church they would connect with all sorts of other people from their community all stratas of income importantly right it's where very wealthy people would meet the very poorest people in their local community they'd have they'd feel a sense of obligation to people who live near them and i think that kind of breakdown in in religion and in i guess religious participation has led to a lot of other negative issues in you know crime rates various other things in in society today i think there's definitely a link there and so as that's broken down you've seen lots of people search for that a similar sense of community elsewhere right and a lot of those are now online right you have all these online communities where you know some of those are very healthy some of those are not very healthy at all right very negative but people want to belong and they want to feel a sense of community and if it's not you know a church it will be something else right and look maybe it's you know um you know it's a it's a biohacking community right maybe it's something you know where they feel like a real sense of community that but people will find it somewhere and um I think that trend of, you know, I guess the traditional religions gradually, you know, losing participation, I think that may reverse at some point soon.

39:55I think people are starting to see the value. Obviously, there's a lot of challenges in the world that come from those religions, including war, etc. But I think there's a lot of value from those religions. and you know i think and i talk about brian johnson again because i think what he's doing with blueprint is in some ways a modern religion right um and he's growing a community of people who all have a shared goal you know don't die or whatever it is um and and yeah look that's not a church religion um but it is a religion which believes in the power of humans you know it's human it's humanistic right like yeah you know that was one of the big reasons the brain becomes the god yeah and look we're maybe we're creating gods at the moment that's another uh thing to talk about but if you you know if you look at like why did the religions break down originally it's because science developed and we gradually you know it was a move from like the theocratic to the human-centric humanistic view of the world which is actually we have power to do all this stuff right that's one of the main reasons but I think there's opportunity to create like modern day religions around believing in humans and humans power to you know solve the biggest problems in the world and Brian Johnson's doing one of those right now I think with what he's doing with blueprint in my view that's a modern day religion and so yeah look if one day I were to ever have time beyond sequel and you know I'm talking about in 15 or 20 years time probably to do something else you know it'd definitely be my goal to I don't want to say start a religion because I'm people going to call me a cult leader but start something which has the you know the elements of a religion the positive elements in terms of building community among people with shared values which are positive for society bring people together from all different parts of society all different backgrounds all different wealth levels and and create like positive outcomes and externalities for people that is something that I would love to do one day I haven't thought about it in too much detail but but it's something I think is like I've gone from you know the kid at university who used to like laugh and debate at people who believed in God right and I now look back thinking that is very cool and I to actually thinking well actually there are so many positive things about religion um you know it's a shame that that is kind of has become a much smaller part of the modern world than it was like four or five hundred years ago yeah and uh um you know when you casually mentioned to me when I asked you how are you and or what your plans are, and you said, oh, well, I'm thinking of starting a new religion.

42:48It was a bit shocking, but then I actually kept thinking about it for days after you mentioned it. And I thought, you know, one of the things that we probably need to do is to update stories that religions are telling us. Because one of the reasons we are disconnecting is because those stories are so irrelevant to our modern lives. There's so much mysticism coming from just the stories from a thousand years ago about goats and some exotic plants that we don't know how they look, right? So if anything, we need to keep the core of the religious message, but update the stories. That's a very good point.

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43:34Because if you look at all religions, they have the same core messages there. like be kind you know love love your neighbor do something for others be good with your community they just wrap them up in different stories and maybe today we need new stories yeah new stories and then it becomes a perfectly realistic project it's not for sure you know we can you know you can create you're amazing at creating stories so of course you could create a religion why not yeah i look i agree storytelling is like the core of it right and there's you know and there's a reason by the way that those stories are still very old stories right it's because that's one of the things which like the human mind works very well there's a we can remember a story right i can tell you a story right now right which should last five minutes long and in a week you'd be able to retell that story yeah if i told you just a sequence of 50 numbers now and i asked you to repeat it in five minutes you wouldn't be able to tell me right and so the human brain really is perfect like vessel for for telling stories remembering them and pass them on through generations so i agree you know more modern stories would be useful and then you know the medium that those stories told in i think is is interesting as well i think i'd love this religion to keep the core messages yeah because when we're trying to reinvent what's good what's bed as happens in some of those modern communities i'm not sure it's very helpful for to help people find that spiritual fulfillment because you know for example even with with exited founders you we see it a lot people realize when they have this space and they're not busy they're like oh my god i actually want to develop spiritually i have no idea what it means yeah I just, I'm so drawn to that direction, but it's too complicated.

45:24And the word spirituality is very scary for some people because it's associated with this confusion and mysticism and something unrelatable, unfortunately. Yeah, and look, a lot of religions focus on what happened after you die. And I'm not sure that that's an interesting thing to think about. I think it's much more interesting to think about what happens while you're alive, right? And, yeah, so look, my view is... People are afraid of death, right? So those ideas, they didn't come out of the blue. They address this core fear of death. Yeah, fear of the unknown, yeah. They try to answer the unanswerable and use that to have power over people, which I don't necessarily think is a good thing.

46:13So, like, I think there's a way to get a lot of those values around helping other people, being kind to your neighbor, you know, being, you know, interacting with your community, right? Like people don't know their neighbors anymore, right? Like in London, like people who are listening to this, you live in a big city, I bet you they know one or two of their neighbors used to know everyone in your street, right? And so there are, there are ways to, I think, kind of get all those positive externalities of religion and religious communities, whilst perhaps having a more humanist approach, as in believing that man has the power to do things without necessarily deferring to some sort of spiritual entity um yeah so i think there's an opportunity there but look i haven't thought about it in detail and you're this is like the first detail conversation i've had about it but but yeah look it's definitely something for for post-sequel yeah alex you said that uh because you already had SQL before you sold Velocity.

47:16You didn't end up in existential crisis. I think you may not be in an existential crisis, but you're clearly thinking about existential issues quite intently. Yes, probably. Yeah. Yeah. Look, so it's a good thing I have something else to do. Otherwise, God, I'd definitely be in a crisis. Okay. But realistically, how much time you spend working on sequel uh it's 90 90 of my time so i'd say less less hours a week than i was uh with velocity black to be very honest but still still a full-time job it's still definitely a full-time job yeah um you know my other job is looking after my wife but um but yeah it's it's definitely 90 of my time i i don't really do you know i stopped angel investing to kind of focus my time on sequel so I'll occasionally make like one angel investment or incubation every couple of years.

48:11But yeah, SQL is 90 % of my time. I'd love to talk about your wife. Yeah, sure. So Miriam worked with you in Velocity and she was with you through all the ups and downs and the exit and everything and the SQL. So how did your exit affect her? And you're not working now together. So how did she handle that? Sure. Yeah. So the story is, I mean, she started working when we were right at the beginning of Velocity. She originally joined us as like almost an intern and then became a marketing assistant. And we didn't have a relationship while she was at Velocity. And I actually fired her. We've got the firing letter framed in our hallway.

48:56But I actually fired her. That's like a movie. I love it. She didn't do anything wrong. She was great, actually. that we we'd bought this company in the US and so we were moving all our marketing operations over to the US and it just wasn't feasible for her to go so we let her go and then it was you know a few weeks later she reached out and asked me to go for lunch for some career advice so that was the I guess start of the relationship and then yeah we got married really just before the exit actually um or around the time that it was happening because it was quite a long process and um and she had had a you know career after leaving velocity and pr and communications uh she worked in a pr firm then she worked for what three words which is like a location technology company in the uk and then also went to work with um andre who who founded a number of companies like Bumble and various other dating, Badoo and various dating platforms.

50:03But yeah, and then we had the exit and before the exit she unfortunately got quite ill with long COVID and chronic Lyme disease, which we think is triggered by the vaccine rather than COVID. um but um but yeah so how did the how did the exit affect her um i think she she yeah she i i think she's definitely more affected by it than me i hope she won't mind me saying that and like worried um because probably she you know she didn't feel in control of and she had less information about what was happening it was also quite you know the actual exit process for us was very intense right was publicly listed bank who was buying us and you know had the federal reserve involved various other regulators etc so it was long and intense um and so that period was very stressful and then obviously you get out the other side and uh you know for me the day that it closed wasn't like oh i'm super happy or whatever you know it was more relief that we got it done for everyone right and i think the peak happiness actually was when we got the offer right and then it's sort of then you go through a big dip as though you're going through all the due diligence all the challenges that come from that and then you know it closes and you're kind of relieved that it's that it's done um but um yeah I think you know I think a lot of I think um I definitely underestimated I think how it would impact her and how you know I think it impacts relationship dynamics and things like that I didn't I didn't impacted our relationship dynamic that much because I had already had some success in my previous career so I didn't think it had a huge impact on us but I think for a lot of people it does and so it's something they should think about and we didn't do any therapy or counseling around it but I would suggest that's a good thing for people to do if they do go through an exit at least have a few conversations together with someone else um who can kind of media and kind of help you talk through anything that you're feeling because um yeah look certainly as a man who's like you know my wife would say uh my wife would say I'm not you know my emotional intelligence is is a fraction of hers so you're probably you're probably underestimating the impact that it might have in your partner right and so it's definitely I think it's definitely something you should have a conversation about yeah but it's interesting that maybe the fact that you kept working and didn't take that break also was good for your relationship because lots of I think that existential crisis often makes it harder I think so yeah yeah it's not working suddenly being at home after you know ten years of not being at home right I don't think she would have liked that no so um and look to be honest you know would i if she wasn't ill um would we have taken some time off to go traveling together for a little bit maybe maybe we would have done that right um so and i think that's probably a good thing to do if you can do it um but um but yeah look i think that it was a good thing that i wasn't just suddenly sort of you know sitting at home doing nothing and having existential crises every day but it sounds like there's quite a lot of structure in your life for the business but also from you know the responsibility to take care of miriam that's also yes a form of a structure and maybe it's not a bad thing you know it's so interesting we we're dreaming about this financial freedom and this absolute freedom and in the western world generally there's a cult of freedom but freedom is tough you know it's actually you're so confused and there is decision paralysis and there's guilt because you think oh I'm free now so I should be doing this that and the other thing but I'm not doing it freedom is so tough and talking about happiness it doesn't bring happiness it brings a challenge it brings an opportunity to make your life more fulfilling because you can step back and think about things and learn new skills or you know reassess your own position in the world to make it more intentional but freedom requires work to be converted into fulfillment.

54:34I agree, yeah. And freedom brings about a lot of ambiguity and a lot of people don't know how to deal with ambiguity. As you said, and particularly founders, feel like they need to do something, right? So they feel uncomfortable doing nothing. And so if you have that void and you have that freedom, They're tempted to fill it with lots of things. That's where they go and do all this stuff. I'm going to look at cash flowing businesses or whatever it is. So, yeah, I'd agree with you. Because I think your situation is really great in many ways because you started a new business before you exited. So you just kind of transitioned smoothly.

55:18But I think once you've exited, then you have to take a bit of sabbatical because an exit triggers so many emotional challenges, then you're so likely to jump into a wrong activity. Yeah, that's true. Just because somebody else is doing it. Because when you started SQL, you had a chance to think about it and just choose. And it was before the exit. It was before the exit. You were not affected by all this freedom. No. Yeah, look, absolutely. And the challenge with the freedom is even bigger if you suddenly have a lot of financial resources, right? Of course. Because it's like, oh. Then you really have freedom.

55:57There's no, let's just throw some money at this. And, you know. So, yeah, look, I think that's definitely a challenge for a lot of people. So, yeah, taking some real time to, and look, maybe that time is three months, maybe it's six months, maybe it's a couple of years, right? Like, however long it is for people, right? But I feel that for most founders, that for most of them, the fulfillment will come through building something again. I think so. And what that is may take you a while to figure out. But I feel like for most of them, that's what will bring them fulfillment. Yeah. That brings me to angel investing.

56:35and your evolution of how you think about it. Yeah, well, I started Angel Investing around the same time as I started Velocity. So it's been like over 10 years now. We should be enough time to figure out if you're any good at it or not. Well, you become good, hopefully, while doing it. So maybe you were not good on day one. yeah look I think there's definitely some luck involved but yeah look I I'm I started angel like you've got to think about like why are you angel investing like what are the goals like you know financial returns may be one of them but typically it isn't if you're not like a full-time investor typically it's like you want to learn about things or you want to help other companies and you feel like that's a good way to start helping other businesses and for me it's definitely a mixture of those two it's like learning from other founders helping them a bit and then financial returns and um yeah I start I started off just you know because when you're a founder you just see other founder friends like starting businesses and the ones that you think are good like okay I'm invest some money in that and um got lucky with the first couple and um when they you know when they exited I thought oh I should really think about this a lot more I should structure this and went through this whole period where I was using quite complicated models to assess things at a very early stage, which was just a big mistake and a complete waste of time.

58:09And then just went back to, it's like that midwit graph, right, where you've got the bell curve, you've got the really smart guy, really dumb guy, and then you've got the midwit. Midwit's got like a thousand questions in their head and all these models they're using to assess whether to make an investment. I'm talking about angel investors, slightly different if you're a VC firm. And then you've got the midwet, you've got the really dumb guy and the really smart guy. And they're both like just back great founders, right? And that's ultimately what it comes down to at the very early stage. So I went through a period where I was like hyper analytical and then regressed back to my original process, which was just, yeah, like, is this a really amazing founder?

58:51you should back them and don't think too much about the products in the market because ultimately the best founders will pivot and find their way to the best products in the best market so um so yeah and yeah i had some some success with it and um i'm now helping through sequel you know our first asset classes venture and we're helping our but this is basically what i'm trying to understand how how that experience of angel investing directly uh transformed into the idea to start SQL? So yeah, I had like a WhatsApp group where I'd share deal flow and it grew quite significantly. And then I had friends and clients, even at Velocity Black, but friends who were in the world of sport and entertainment who wanted to invest.

59:38And, you know, there are two real, I think, challenges with startup investing if you're trying to do it really well. and one of them is getting access into the best companies right and even if you see them right which is the first challenge like just seeing these companies okay now you've seen them and you know around's happening how do you get into them right and um as a founder and operator you have a slight advantage right because founders are really like raising from other founders because they're not going to they kind of understand the problems that they're facing they're going to be helpful they're going to have relevant experience they're not going to cause them loads of problems like some other professional investors might do but I saw with some of my friends who are athletes in the entertainment industry they were able to get into any deal they wanted to right and I thought there's something interesting that and they were also able to help them post post investment right and help accelerate them they're very high profiles they can help tell their story and amplify that story to tens of millions of people right quite easily and they also have that you know athletes have a very similar mindset to founders right like they've they have to be you know they have to be very hard working and persistent they're they you know they're both playing power law games right like very small percentage of athletes reach the top very small percentage of founders end up being successful um and so there's a lot of ways they can help beyond just sort of marketing and and helping tell the story and so I thought there was an interesting opportunity there to kind of leverage the talent and and and in some cases expertise right because we're now we're going to expand beyond athletes into the entertainment industry eventually into exit founders anyone who can bring expertise the underlying assets so how can we leverage that talent to get access the very best investment opportunities right and help them invest in them and us invest in them and then post investment help accelerate those companies and hopefully generate real added value right and added value is something which a lot of people talk about i can just tell you as a founder and from my founder friends 95 of investors add no value um and and most of them well i'd say they can be even quite detrimental right like no and and look let's be honest i'm not claiming that any of our athletes or us are going to be the reason that one of our portfolio companies succeeds.

1:02:07And you will find this, you know, no investor will really make your company, right? They can't break it, right, if you have the wrong investor on your board. But yeah, that was the opportunity. Like, you know, really, if you're thinking about like a startup that wants to solve a big problem for the world in like healthcare, climate, education, you know, what do they need to succeed? They need capital and resources and they need the world's attention, right? And if they can get those two things and they've got a good product, they can, you know, they've got a good chance of succeeding. And so with SQL, we're really trying to help them on those first two things.

1:02:42We can help, obviously, with capital and then we can help tell their story and get it out there into the world and help accelerate them on that path. And, yeah, we'll see if the thesis works. It's still very early for SQL, at least. But it evolved from my personal angel investing and having some friends who are athletes. two of my other ex-to-founder friends Nick Telson Andrew Webster who founded Design My Night originally approached me about hey we should start a syndicate for athletes and I was like yeah it's interesting and then I came back to them and I was like actually I think we can do something a lot bigger here's what I would do and they were like okay can we invest and so yeah we started it so so yeah it kind of evolved very organically from you know it does feel like I have very good founder market fit for it right in terms of I've been a founder obviously I had 10 years angel investing I understand what it's like to work with this highly demanding highly successful high net worth clients from my first business and I had a good network in sport and entertainment so it kind of felt like all the pieces were fitting together and that it's something that has been building up for the past decade rather than from me just having the idea and then going out and figuring all these things out right it felt very natural to me to start it so you know what I find fascinating from my standpoint because I am obsessed about post exit journeys right and um on your website you talk about legacy right that's the word you offer to your clients and um I think it's actually fascinating because athletes don't have their long careers so they end up in this journey which is post exit to just exit that their careers as opposed to business and I have amazing friends who are athletes and I saw them going through very similar psychological issues so I thought it was fascinating to offer these people legacy in a way as a as a help to transition into something meaningful by associating themselves with companies that are solving really important problems, you'll help them avoid this void that we were talking about.

1:05:07Absolutely. That's very good. I think it's an amazing value that you're given, this sense of legacy, creating legacy. It's not just wealth creation. No, yeah, look, we say that we're helping them build a legacy for their families and for the world, right? And for the world, it's about hopefully bringing capital and the world's attention to these game-changing technologies and companies which are going to solve all these big problems, right? And for them and their families, obviously money is a part of it, but as you said like they you know their careers are very short right and this is why we called it sequel it's like what comes next after your relatively short career in sport you know in the nfl it's like four years right it's very short um many many because of injury but even then most athletes by the time they're in their mid-30s they're retired right so um so how and you know that's a long there's still a lot of life left after that right and um and obviously part of that you see a lot of problems as you'll see with founders after they after that you know that their first career ends right and they go through a lot of existential crises you know some of them financially driven right because suddenly your income drops to zero and you know if your lifestyle it's not like you've had an exit right so in some cases it's more aggressive than than a founder's transition out of their career so they you know some of it's financially driven and you know the whole family has to get used to a low you know a slightly different lifestyle to be honest um if they haven't prepared well for their retirement and so you know our approach to this to sequel was okay firstly we want to help them build wealth so that they're set up very well for the rest of their life beyond the end of their sporting career right secondly we want to help them make better decisions right and so what you'll find is a lot of solutions that for athletes that are out there whether it's these athlete-led funds athlete-led athlete-marketed funds um or other sort of wealth solutions financial advisors what most of them do is treat athletes like children they try and take away responsibility and decision making from them and they manage everything for them and in some way that's a that's a good service right okay i don't have to think about it but what happens after the end of your career when none of those people are there anymore right because they're not interested in you because you're not earning lots of money anymore what happens then how do you make decisions every day how do you do you know enough to make basic like financial planning decisions do you know enough to make good business decisions good career decisions and so our approach was we're actually not going to manage all this stuff for you we're going to give you the information the tools and the education through like short form video content and events and things so you learn very quickly about investing about entrepreneurship about startups about big business and we're going to enable you to be good decision makers so we're going to educate you and we're partnering with all these top education institutions to give you like accredited courses on this stuff through through the membership and so not only do we set you up hopefully by helping you invest in the very best you know assets out there which you know on the right time frame are going to provide very good returns into your retirement from your first career in sport but we're going to set you up with the knowledge to be able to make decisions for yourself whether it's during your playing career or after your playing career more importantly when pretty much everyone else around you goes away right and that's where you find athletes have a lot of problems they get into financial difficulties they have health problems and so we're taking the approach of which is a harder approach by the way it's much more expensive for us to do this and it like we have to invest lots of money to create like relevant content and to find ways to engage athletes and it'd be much easier for us to just go and manage their money for them you make them work but people don't like that yeah so it would be easier it'd be much easier to do it the other way right and look and this is our first you know our first target market is definitely those growth mindset athletes who want to learn this stuff right and eventually we will have some manage solutions and wealth management products but we're really focused at the moment on you know if we really want them to build a legacy for their families they need to have the knowledge to make good decisions right and so we're we're equipping them to do that through the platform you know lots of existent founders could could use that because it's very hard to transfer from an entrepreneur mindset into an investor mindset and then we don't have tools just because we are dealing with money much more than an average athlete doesn't make us good investors.

1:09:51Quite the opposite. We often have this hubris post-exit, right? We think, and we have lots of friends in common who invested a lot in angel deals. I did, by the way, as well. I didn't do a very good job. Just to realize that it's very different from running your own business. Yes, it is, yeah. And it's almost the opposite mindset that you need to be a successful investor. Because it's so interesting with angel investing. It's the thing that people do most often post-exit, but it's also the thing that people who exited long ago mention first when I ask them, what do you regret? And I think the answer is not that angel investing is wrong per se, but we have no idea how to do it, but we are very generous with founders.

1:10:38We feel so much compassion, and then we also miss the whole entrepreneurial buzz, and we think, oh, if I invest here, I'll get a little bit of that back. So there are all these wrong reasons, wrong meaning irresponsible financially, reasons to invest. or just we do it for fun together with our friends because they do. We get excited and all these impulsive decisions. And sometimes, by the way, it is greed because even if we have good exit wealth, we start panicking and we think, oh, my God, I need to invest somewhere because otherwise my bankers will only give me a 3 % return. Yes, yeah, yeah.

1:11:19Right? There's definitely, yeah. Look, at some point we will definitely address extra founders. Yeah, this whole education around angel investing is so important. But it's also so hard because you're right. You can't apply difficult, complex formulas to this. So much of it is just psychology and also understanding whether this founder will work this hard for 10, 15 years to deliver results. You want to make it very easy for people, right? So they don't see all the thousands of companies that we look at that we don't invest in, our whole DD process, our investment committee, all the memos and stuff we write.

1:11:59They don't see any of that. They just see a very simple video memo with a very slick app, and they're able to make an easy decision. But in order to do that, they need to have some knowledge. So yeah, I think the education part's super important, and we will definitely address extra founders at some point. but like I have like very much like a definitely a disciple of Peter Thiel in terms of you know focusing on a very niche market initially makes a lot of sense and focusing all your marketing and resources around that niche market winning in it and you know effectively creating a monopoly in that market and then moving into adjacent markets it makes a lot of sense we'll get there eventually but and as tempting as it would be to do it now I think it's you know I think it's stronger for us from a marketing perspective from our messaging to be very focused on on athletes initially and then we'll move into entertainment and it's not just marketing you're learning from your customers right how to deliver the result that that they actually want exactly precisely um so yeah we'll see makes a lot of sense for you but poor exited founders still lack education yeah yeah i think some of them do and yeah and you're you're right like the it's funny that there is hubris, right?

1:13:13Because people think, oh, I've been, you know, I'm a successful entrepreneur. You know, I know what I'm doing, right? I make smart decisions. At least athletes are usually realistic about their financial acumen. Yes, they are. But not successful founders. That's funny, yeah. You're absolutely right on that point, yeah. The athletes are actually much more conservative and are much more careful than a lot of exited founders. Well, at least they get realistic. Yes, realistic, yeah. About their own abilities. Yeah. But we'll see. Exeter Founders is probably, yeah, probably two to three years away.

1:13:48We could start looking at that. So in terms of what type of entrepreneur are you, if you had to choose between a creator, an operator, and an investor as your natural type, what would be your immediate reaction without overanalyzing it? Creator. Yeah, that's what I thought. Yeah. But you know, it also means that you'll probably get bored as soon as your business becomes bigger. Well, it depends. It depends. That plan to do this business for 15, 20 years. Let's see, like a Velocity Black, I did step back to be chairman to start something new. Exactly. There's definitely an element of that. And I don't want to say we weren't innovating at all at that point, but we were innovating far less.

1:14:35And, you know, one of the reasons we were able to successfully go fully remote is because it was a very like a lot of the business was completely systematized at this point. Right. And process in place and everything. And, you know, there was certainly less creativity involved in the day to day work. I don't think that has to be the case as you grow a company. And I think you can grow to be, you know, even a 10 billion dollar business and still have huge amounts of creativity involved in your day to day work. If you think about it proactively. Right. And there's this real push from, and to be honest, pretty much every business book, any person that advises you, any VC that sits on your board, they want to systematize things.

1:15:19They want to put process in place everywhere. Of course. And they want to make the business easy to manage, right? Because as it grows in complexity, you have chaos emerges, right? Exactly. have if you know so my approach is a lot more you know i love what reed hastings did with netflix which is like the way to address complexity in a business is not to put in place more and more processes right it's just to have to be extremely rigorous about the level of talent you have in the company right and making sure you have the very best people in the company means that they can have more freedom they can be more creative because you don't need to have all these processes in place like kind of solving for the lowest common denominator like team member who's the guy who makes a mistake and it costs the business 10 million dollars or whatever right so the higher quality talent bar you have the more I think as the business grows you're able to embrace creativity you're able to embrace not necessarily having a completely systematized you know business where you're just pressing a button and everything else works right And so I think there's a way to build a very big business.

1:16:26And I think some people have proven it where you can continue to have that creativity. You can continue to launch new products. You can continue to innovate. And you can resist the demand from investors, capital markets, people with MBAs. No offense to people with MBAs. To kind of systematize and make your business too process driven. right and so I think you can like if you're a founder and you're a creator type I think you can you know there is a way to resist the demand to to kind of be more of an operator right there's there's a way to resist that and so I hope to be able to prove that with SQL yeah but I guess you still need a partner or or employees who are natural operators and luckily I do have that they should be very good very talented Philip is my co-founder and CTO and he's definitely a lot more I'd still say he's a creator but he's a lot more systematic than I am and then I have a VP of operations Sophie who's very she's definitely an operator without Sophie and Philip my approach would just lead to chaos because a creator would want some chaos otherwise you cannot create I do enjoy chaos I frequently use it I still use it embrace the chaos I found that it's so important to understand who you are even though I generally don't like putting people into any pigeon holes but this particular thing I think it's so important to understand because so many of us rush into this idea that I'm going to be this amazing private equity investor or I'll buy someone else's business.

1:18:17But if you are a creator, you're not going to succeed in this because you start hating that. Yeah, yeah, yeah. You have to start from scratch if you're a creator. Whether you like it or not. It has to be something very creative. It can't be just this passive kind of lifestyle. I'll help make some other business scale. Scaling is not what creators do very well. Exactly, yeah. So, yeah, like you have to embrace what you enjoy for sure if you're going to succeed. And then, you know, hiring the very best talent to help in the areas that you don't enjoy. Right. And where they can have where they can actually add structure and succeed.

1:18:57I think there is, you know, being a creator feels cooler than being an operator. So some people also think they're creators and don't want to embrace the fact that they're operators. And that is also not helpful. yeah definitely yeah you know what i mean i know what you mean yeah um it's kind of sexier to be a creator it is yeah yeah and look with my first business with velocity black i was basically forced into the operator role right like i had to do that because zia was better at being the creator with that business and um which is interesting because he he was the one coming from goldman sachs you would think he would be he's very creative an operator he's very creative but look we look to be clear we both were inputting on product and stuff as well but But I was forced into doing the operator role, which was setting up all these repeatable processes, scaling the operations team, et cetera, which was the revenue part of the business.

1:19:52But it was very much an operator role. And that probably led to a lot of the stress that I had on that journey. And frustration. And frustration, yeah. What would you say you are, Anastasia? A creator. A creator. And you know when I found out in my second business, I hired a CEO quite relatively early on. And that person was so much better than me in operations. It was a very humbling experience, but also it made me think, okay, great. So I probably shouldn't be forcing myself to do that. Because like you, I was very stressed by all of that. And I thought, okay, that's fine. I just embrace who I am.

1:20:35and next time I'll start my next business with a partner who is very happy being an operator. Yeah, yeah, that makes sense, yeah. And look, we'll see what happens as the business grows. I think you can have creator CEOs, for sure, as long as you have a very good operator partner. and yeah look and it also depends on the type of business you know we're our clients are individuals who expect to have a relationship with the CEO right like that's their expectation and I think that will always be the case right even if everything we do is through technology and it's through content you know I might have spoken to all of our clients at least once but they feel like they know me very well through our content right and um yeah and you know they engage through you know messaging and stuff through our product as well so they feel like they have a real relationship with us even though it's very tech driven um but i think you can't like yeah look depending on the business i think creator ceos generally um are more successful um that's that's just my personal view and i think typically and and a lot of fat i think a lot of founders fit more in the creator profile out of the three you mentioned.

1:22:04And I think typically, and you can look at this in the public markets, right, the founder-led businesses still significantly outperform non-founder-led businesses, right? Yeah, definitely. And look, Elon's obviously an extreme example, but he's certainly not an operator. He's clearly a creator right and but he has amazing you know he has Gwyn at SpaceX right she's really running everything right she's she's doing what you what you said you know hire amazing people yeah so um so yeah I think you know I think you've just got to yeah you've got to recognize which one of those you are and make sure you complement yourself with partners who can help with the other areas okay so you you're building these relationships with your clients that makes a lot of sense How about in your personal life?

1:22:53Do you feel lonely at the top? Do you feel you have the right tribe, the right community for you at the moment, at this stage in your life? Yeah, look, I'd say I have a very small number of friends outside of work, like very, very small. And mostly they're friends who I've known since school, right? So it's still very long-lasting relationships. But very small. I'm talking about like five or six people and probably two who I'd see regularly. So and a lot of that is just down to how much energy I have to dedicate towards relationships outside of work and outside of looking after Miriam and my dog.

1:23:39So I keep it very small and concentrated and I'm very happy with that. And I'm probably like increasingly like kind of grumpy old man type person. like do i need more do i need more friends now you know do you know what i mean um so yeah look i uh i i would like to i i generally i don't have much of a social life at the moment um again mainly like if miriam was better and was able to leave the house like we would um we'd obviously be so well she'd be forcing me to socialize a lot more let me put it that way um but as she used to before she was ill so um so yeah look i think um i'm happy with my social life as it is i like you know the things that like give me inspiration or make me kind of fulfilled outside of work is doing things like adventures or whatever with my friends right like a couple of times a year doing something crazy um or fun you know like last year i ran an ultra marathon in africa with um with uh russ cook did you see that guy who ran the whole length of africa no really interesting like a russ cook he ran the first guy to run so you did it with him part of the last the last leg i flew out at two days notice i decided to fly out with some friends and we ran the lot and i'd never run a marathon before and it was like how did this feel 40 degree heat i mean it was intense but i did it right i completely wanted to do something crazy yeah yeah so i like doing that kind of thing a couple of times a year with a small group of friends.

1:25:15That sounds like something a creator would do, not an operator. Probably, yeah, with almost no planning. Exactly. So, yeah, those are the kind of things. Look, I think people go through different phases in their life. I don't have any kids yet. I do want to have a lot of kids, and so that will obviously take up a lot of time when I have kids. But, yeah, look, I think if you're getting, you know, who did I see? You said it the other day. The situation you want to be in is you want to be really looking forward to going to work in the morning, and you want to be really looking forward to coming home in the evening.

1:25:55And if those two things are true, you probably have, like, a happy or fulfilled life, right? And so I definitely feel that at the moment. I agree. It's a perfect formula. And then, of course, you also need to make sure that you feel satisfied with what you have. yes sometimes it's our fears or inner battles that actually prevent us from realizing that we can happily go to work and happily come back home yes we just need to think about there we go right yeah it's you know it's like it's that classic conundrum which is like desire is both the source probably of all human progress ever yeah and it's also probably the source of all human misery and so it's like those two sides of that coin and knowing when to control your desire and be satisfied and be fulfilled I think is the real challenge so you still want that desire because that's what kind of whatever it is, it doesn't have to be for money or anything but you want the desire to do things to achieve things Don't you think desires can be very different because it depends on where your desire comes from So if it comes from fear or greed or comparison, which is a fear of feeling worse than other people, that feels very different from the desire to solve a big problem for the humanity.

1:27:25Yeah, yeah, absolutely. Yeah, for sure. The level of fulfillment is very different when you get what you desire. Yeah. Yeah. OK, so again, let's say this to extreme. what do you think Elon Musk thinks? Because, you know, firstly, he's obviously achieved amazing things with humanity. Do you think he feels happy? Do you think he's, like, fulfilled? I think he feels fulfilled. I think he feels fulfilled, yeah. Happiness probably doesn't happen very often to him. I agree, yeah. You know, there's this interview where he actually said that, you know, guys, you don't want to be like me. You know, my life is so hard.

1:28:07It's so difficult. It's so this and so that. But then you look at him and you're like, yeah, but you're fulfilled. You know, when I read this biography of Steve Jobs, I completely changed how I thought about him. Because for many years, I thought of him as a miserable man. Really? who sacrificed for the... He was amazing at what he did as an Apple founder. But I thought, but, you know, he was a miserable man because people often talk about how he was a miserable man. But when I read his biography, I thought, no, he was actually deeply fulfilled. He just didn't care much about this happiness. Happiness, yeah.

1:28:48He didn't chase it. He didn't chase it. And people thought, because he's not chasing it, he's miserable. but this is what you kept talking about in the beginning of our conversation you know fulfillment and happiness are different things and fulfillment comes through struggle right it doesn't it again it comes from being in uncomfortable places and doing uncomfortable things and and from taking risks and being willing to fail and unfortunately like pretty much every piece of media out there mainstream media education our education system our psychiatrists and mental health and public health systems all teach us to search for happiness and that's why i think so many people are miserable yeah honestly i think it is right it's like the pursuit of happiness leads to misery and um yeah look i you know uh which which biography was it by the way was it the The Isakson one.

1:29:45Isakson, yeah. I still haven't read it. I need to read it. It's fantastic. Because there are so many other biographies, but this one was the one who, for me, made it very clear. Even though Walter often talks about how Steve made other people miserable and how he felt miserable and how he was angry, but if you look through that, it's actually very clear that he was fulfilled. Yeah, and it's the pursuit of excellence, right? You have to care about what you're working on.

1:30:19We often get taught, I did this leadership training with my team, and we had a former U.S. Navy SEAL commander and FBI special agent, a guy called Errol Dobler, a really good guy. I highly recommend him as a leadership trainer. He came and did a lot of work with us. And a lot of what he talks about is like, you know, controlling your emotions or at least knowing how you're feeling and kind of separating that from making a decision and reacting. And I think a lot of people in like the corporate world or in the startup world mean, interpret that to mean don't show any emotion. That's not what it means at all.

1:31:05It means being conscious about the emotion you're showing. and I'm very sure that when Steve Jobs was having those outbursts and you know smashing the prototypes on the ground it was intentional and he like and it wasn't fake that was how he's feeling but he had a reaction he thought about it and he was intentional in how he reacted and and and and that is that is how it should be right and that is that is demonstrating a care for your work and that you care for your team right it sounds strange but it is showing that you care for your team because you want them to care about this as much you want them to succeed on the project and succeed in their careers and try and i think he cared about some members of his team those who were aligned with him uh probably yeah yeah probably not the rest well there we go he should you know he should have had a better hiring process but um no he was just brutally honest to those who didn't quite perform or didn't quite care But that is caring.

1:32:03But that's caring. That is caring, right? This is what I tell my team, right? Like, you know, the biggest gift you can give someone is feedback, right? And real feedback, honest feedback, right? And, you know, there's all these books, Radical Candor and various others that go through this. But that is caring, right? You know, telling someone something's great when it isn't, that is not caring. That is, you know, that's jeopardizing someone's growth potential. That's jeopardizing someone's future career, right? So, you know, yeah, I will definitely read that biography. I've listened to a few before, but I haven't actually read that one.

1:32:45So I will read it. So, Alex, my last question. I always ask the same question at the end. How do you want to be remembered? um so I was funny because I was reading over Christmas my uh I was reading over Christmas my yearbook from my primary school okay and you write like a little page this is when I was 12 years old and you write like you know there's certain things you have to write on this page and there were two things on the page that really stood out to me so the first one was I said and by the way I wrote this I would have written this in like April 2000 so it's like peak of the first internet boom right and the one of the first things one of those is to be up to me as I said when I'm older I want to run a big computer software company and make lots of money right so that was like funny obviously um and the other thing which um I noticed and I noticed it a lot because a lot of my friends from back then replied to me uh highlighting it saying I think when I'm uh when I'm older or when I'm gone I want to be remembered as a very kind person who would always help his friends right um I'd still say that's very true um but I'd kind of I'd want to expand it to be helping more than just my friends and hopefully helping helping mankind right and and you know that word kind is interesting and that the discussion we just had around Steve Jobs is an interesting example like my definition of kind is often very different from other people's My definition of kind is helping people learn, helping people progress, helping people do better.

1:34:24And sometimes that involves saying a brutally honest truth, right? And pointing out the inconvenient things and pointing out the hard path that we have to take and the struggle that we have to do in order to progress, right? And that's my definition of kind. And look, I hope that I'll be remembered as someone who is kind and helped in some ways progress humanity in various different ways. That's so beautiful. I'm sure you will. Thank you. Thanks. Thank you so much. Thanks. I really enjoyed it. Awesome. Yeah, so did I. Thank you very much.

From the publisher

What would you do if you sold your company for 300 million dollars? Retire? Explore the world? Do all these other things you had no time to do while building a business?

This is not what my friend Alex Macdonald did when he sold his company Velocity Black two years ago. In fact, Alex made it quite impossible for himself to have any kind of post-exit sabbatical. Why?

Well, Alex has seen enough of his post-exit founder friends getting stuck in full-blown existential crisis after they sold their company. He didn't want that to happen to him. I think honestly, if I had had that void, it probably would have not led to a productive use of my energy. I'm actually very happy that I had something immediately to jump into. And yeah, that's led to me not having to go through that challenging period that I see a lot of my friends go through, questioning their identity and everything.

In this episode, we're going to explore why he made this decision, whether two years later he still feels it was the right one, and how he applies the lessons from his first full entrepreneurial cycle to building his new business, appropriately called SQL.

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