23 Oct 2026 · 85 min
In this segment of the podcast "The Exit Files: The Long Way Out," several founders discuss three inter‑related themes that shape the exit journey. Speaker E explains how re‑hiring trusted colleagues from a previous venture (Whisk) creates a strong, cohesive team for a new startup, emphasizing the importance of pre‑existing relationships and cultural fit. Speaker H articulates a concise entrepreneurial exit principle: when an entrepreneur perceives that someone else can generate more value for the company than they can, they should step aside, distinguishing the creator‑entrepreneur from a mere business owner. Speaker G reflects on life after an exit, describing a purpose‑driven consultancy (SCaLE) that deliberately remains small and relationship‑focused, rejecting heavy automation in favor of human connection, and highlighting the need for meaningful work beyond financial freedom. Together, the conversation weaves a narrative about building trusted teams, recognizing the right moment to exit, and finding purposeful engagement after a liquidity event.
Chapters
We took the money and ran. We had over 3 offers, I think, that were over $100 million. And at some point in time, you're like, just doing the math, you're like, this is an insane amount of money. You know?
When the figure finally came, it was a bit of an anticlimax and a bit weird because it was a Monday afternoon. I was still at work. I had to go straight into a big presentation with the team, literally like an hour after the money hit my account. It was just the most bizarre. They didn't know, couldn't tell them at the time.
I was like, Jesus, this is why I started a business. I don't want to work for anyone else. And then suddenly this new acquirer is telling you how to run your own business. So it's almost doubly worse.
But I gained so much more on the other side, right? I gained my freedom and my financial freedom. I met David, my co-founder and my husband, my life partner on the way. I discovered music and community in Amsterdam, and I got to travel because I met him. So I gained a lot more.
They call it holdback, where part of the cash I was paid for the acquisition was held in an escrow. If I left the company, they, they would not give it to me. So I had to stay for 3 years. 3 years went, all the money was paid to me. And I was like, what do I, what do I do?
I wish I would have never sold it. Like, that company today would probably be a unicorn. It would probably be worth a billion dollars. I didn't at that time have any idea what a startup was or venture capital or even entrepreneurship. I was just a guy trying to build some software and we had customers that wanted to pay for it. That was it. It was just a business. We started a business. We had customers from the very beginning and it just slowly grew. We never raised any outside capital at all. We did get to a phase where we were very rapidly growing into like 2007, 2008. And we wanted to raise capital then for growth. But if you remember what happened in the United States in that time, that's when General Motors went bankrupt, Chrysler went bankrupt, Ford closed a lot of stores. Was not a good time to be raising capital, especially when you're in the automotive sector and it's like kind of doom and gloom with all the automotive, you know, big manufacturers. But it was actually all a huge positive for us. You know, when car dealers are making a lot of money, they spend a lot of money, right? They're like TV ads, radio ads, newspaper. They're just throwing money everywhere. They're making lots of money. When they're not making a lot of money, they're trying to figure out how to save money. And we were the perfect solution to help them save money and move to digital. Like, we're not going to pay for radio and TV anymore. We're going to spend more money on autotrader.com and cars.com and eBay, but we need a tool to help manage these internet leads and how we do this digital thing that was new. And we had the right product at the right time. And so that recession actually was a huge boom for us. We were growing way faster than we could even keep up with it. We bootstrapped this all the way over $30 million a year in revenue. And we didn't, we didn't have enough servers. We didn't have enough support people. Like we, we were just struggling to keep up with all of it. And we really could have used like a big influx of cash to like really overhire and do some things the right way. Although it's interesting, when we got to the end of it, we became so profitable, we really didn't even need to raise capital anymore.
We'd always had pretty strong margins, actually. We were fortunate and pretty much doubling each year. So the revenue part's fine, but I think turnover's vanity, you know, profit sanity, as they say. So we always had a very healthy bottom line number, 25 to 30%, which again, for a service-based business is pretty good. One of the things at scale that I certainly hadn't anticipated was just how difficult it would be to bring in the team members, support them, give them the structure. And I always talk about having like a seesaw effect. So if you bring in sales, it leans on the operational team and then they need to try and counterbalance. And you've got this constant seesaw of trying to like bring sales, balance the internal work. And if one of those things doesn't do a good job, then you can have a leaky bucket over here, or, you know, so trying to support the team at that scale was difficult. I would say on average, we were bringing in at least 2 team members a month. There was a few months where we brought 5 or 6 new team members. And it's hard to do a good enough job of like looking after those individuals when from a management team structure, we didn't always have it together either. So It was a lot of firefighting. I would say that was probably the hardest thing and it was exciting. The growth was great.
Zebra reached unicorn scale.
Yes.
I'm wondering, what does that type of success start to cost personally? Because not a lot of people on this planet had a taste of that either way.
Yeah, it took us about 8 years to reach a billion-plus valuation, and it certainly did not happen in any sort of linear path. Like we were entering a space that was, it's very regulated, it's very stodgy. And it's complex. And, and so the players in the space are used to doing things a certain way, which was obviously what we were trying to disrupt. So we had to, we had to almost adopt their methodology first because it was, there was this element of like, okay, if we're going to change this space, we need to kind of get in on the playing field that they're currently on. And, and as long as we keep that vision, we will incrementally We will get there. It'll take time, and it did, but we will get there. And so going through that journey though was very, very confusing because we had to sell people, certainly the investors, on, you know, hey, we're heading this path, which looks like it's like completely disparate from where we're wanting to go, but you have to trust us that in order to get there, we're going to need to do this first. And then, you know, We will evolve into what we want to, but that process is very stressful. So, and it takes a lot of faith and you're constantly questioning yourself and every— because everybody's questioning you. And so, you know, you find yourself having to put on a brave face, smile, and like tell the story and get people fired up. And you're going to bed at night kind of like wondering, like, am I losing my mind? Is this really how I should be building this company? But ultimately, like, that instinct was right and it worked, but it was a very emotional, like, or I guess emotional, yeah, but just very challenging thing to do. So I like to joke that it took like 10 years off my life building that business, but also it was, it was as challenging as it was, of It's certainly not a straight line, is it?
We fought very fiercely for our culture because I believe the saying that, you know, go fast, go alone, go far, go together. And I realized that pretty quickly. I was very fortunate to have a really good advisor who became a non-exec for our business, actually, that kind of helped me kind of understand the importance of that as well. And I think we Several times we realized that we weren't setting the bar high enough culturally. So people were kind of, you know, you can't carry anyone in a small business. And, you know, we were 10 people, then we were 20 people, then we were 30, then 40, then 50. And so several times we had to kind of make difficult decisions about, you know, not carrying people and removing them. And that was, that's never easy, particularly in a people-based business, right? To do that in the right way. There's a period in business where you look at somebody in the room that you're employing and you think, If they leave, we are in trouble. And they become really, really important to you. But then you get a little bit further on in your growth stage and they can become the problem or the blocker actually. The business has outgrown them. And that's a really difficult scenario. And I think a lot of the work that I do now is helping people understand and seeing that early and making sure that they have a plan to move those people into the right seat or off the bus because you need better people around you.
Being bold and brave enough to push back on clients is something that agencies don't do enough and they need to do more of. You know, I actually got the bug in the end, like addicted to sacking clients. It sounds awful, but you know, there is such thing as bad revenue, right? You know, if your team members are stressed, under pressure, unhappy at work, it affects all of your good clients as well as that one or two bad clients. might have. So I used to find that team morale from one bad client could be completely decimated week over week, month over month. So if there was a client that consistently caused problems, regardless of revenue, I would allow a kind of 3-strike rule, and then we would sack them. So I think if I look back at Digital Ethers, I must have sacked 20 clients for just being bad operators and bad business people. Just, they didn't fit our ethos, they didn't fit our mentality. And There was a situation I always remember. It was a $120K a year client, a decent revenue, $10 grand a month client. They'd only worked with us for 4 months, but I had 2 team members come into my office in tears because they were— the client was just not listening, was screaming down the phone, just bad business. So I called them and let them go. And, you know, it was a very liberating thing to do. I think it was good for the team. The morale went up, the outputs and outcomes then for the other clients arguably increased. But as a business owner, I think a couple of years prior to that, I'd have never dared to do it. I was like, no, no, because you need the money. You're always chasing more retainers. You're chasing the— you want to see things spiking, but actually there is bad revenue and having the ability and the kind of guts and the bravery to make those bold decisions is the difference between leading or just managing. You just need to have the COVID there and a business that can survive the founder effectively. That's really what it comes down to. So for me, it was all about putting the right people in the right place. I didn't always get that right, by the way. I hired a few people that didn't work out and like all of those things, like it takes time. And I was fortunate that I started doing this 2 years before I was ready to sell. So, you know, I started bringing in the individuals. I had a really clear goal to have my chief operating officer effectively, you know, as the MD or ready to be the MD. And I spent a lot of time coaching and putting my thoughts and talent into those individuals. And we had a board internally of 5 people. So if one of us fell over, the other 4 could still pick up. And that became more attractive at a point of sale. Having been through those burnout stages, okay, arguably a lot of people, when I say that, they're like, yeah, but you got an exit. It's like, yeah, I did. But I'm lucky that I did. I'm lucky that I had the leadership team around me at the time because my burnout would have crippled the business otherwise if it had all been on my shoulders. When I had those burnout stages, the business would have no way been able to be sellable in the end. It's only because of the structure I put in place before that happened, thank God, that we were able to get there.
A lot of the luxuries that I have in my life right now, like the freedom, the friends, the community, you know, being able to travel, work remotely, these are all earned privileges. But before eWebinar, I had almost 10 years of Pure suffering, working on products that weren't great, that didn't have potential to be great. You know, really tiny industries, fighting for every sale, living very frugally, being in a house with 5 other people, right? Paying myself $2,000 a month and then $3,000 a month and $4,000 a month until I was 36, right? Like going to a restaurant and, and picking the cheapest thing or meeting my friends after they eat and making up an excuse as to why I couldn't go for dinner. Missing all the weddings that I was supposed to go to, you know, not going to all the, any of the bachelorette parties, losing friends over it because I, I was choosing a business trip over, you know, going on, going on a fun trip. You know, those are, you know, maybe probably friendships that wouldn't have lasted, but at that time it was important. You know, just life stuff, right? I used to think that founders should get paid last and the least. And after 10 years of pain and not being in a good mental state to build my companies, I now believe that Founder should get paid first, at least something, and then in the end, the most to support their lifestyle because you are the company. The biggest variable to success is the founder. So the founder should not put themselves in a painful position to build their company.
But that pain tends to be something that people expect.
Yeah, but it doesn't have to be your reality. You can change that. Sacrifice and pain doesn't mean success. It's just sacrifice and pain. If you are constantly in survival mode, which I have been in for years, you cannot make good decisions for your company. You just can't. I mean, ironically, I started a company to be rich and then nobody told me that starting a company would be the quickest way to lose all your money. But I gained so much more on the other side, right? I gained my freedom. and my financial freedom. I met David, my co-founder and my husband, my life partner, on the way.
Because Design My Night was sort of my mid-20s, I sort of sacrificed like that fun stage, the sort of coming of age stage. I had university, loved it, sort of came of age at university. But then, you know, those 20s where you've got maybe your first job and you're getting a salary for the first time. You know, I definitely sacrificed that sort of fun, fancy-free, you know, no responsibilities sort of part of my life, which is regrettable, but I don't regret building Design My Night. I was very lucky that my, my other half, my friends, my family in the main were all very understanding of the work that I was doing on Design My Night. So I probably wasn't the best friend and son, etc. But they were understanding of that. And I've sort of made up for that since. So again, I'm very deliberate with the relationships I have now with my loved ones and hugely appreciate that as well. And I think that's another thing when, when I speak to founders is like saying, making sure your loved ones and your friends and family are very aware of the journey you're going on. Because they are going to have to support you. And they're going to have to accept that you're not going to be the best version of yourself with them. So if you can have that support base, it's really important. But yeah, it's mainly around that. But you know, the flip of that is I love it. I love building companies. I've loved building Design My Night. I love the financial freedom that that's now given me to have a wonderful 30s, 40s, 50s, and beyond. So yeah, I don't necessarily regret anything, but yeah, obviously just missed out on some things.
It's, it's, it's hard to say because at some point to me, it's not a sacrifice. You know, I'm definitely, I definitely worked a lot in my life. You know, I've got those friends that I put all my money in my business. You know, I've got those friends who went, uh, went on holiday constantly, were having, you know, partying constantly. And I worked a lot. That's for sure. And I didn't have much peace in terms of sleep. I'd say, okay, honestly, until 35, every month I didn't know how this is going to end. Am I going to have enough money to pay the rent? And of course, sometimes you insist more, it's better. And then, uh, and then you get back on the, I, I don't know how it's gonna end. Uh, this, I, I think the sacrifice is the peace of mind.
There we go.
Uh, that's, that's the sacrifice I did.
Andrew and I were very deliberate with the exit of Design by Night. So it was not something we, we knew that we wanted to work on forever. As I said, we were young when we started it. We sold it in 2017. So that was 7 years of sort of just nonstop work, 24/7, 7 days a week. So it took a toll mentally on us. But we'd also agreed what we wanted out of Design by Night. And it's something a lot of founders don't do when they start. I think a lot of founders just think, I want to build a unicorn. You know, because that's what you're told to do in TechCrunch and stuff. But actually, when you decide what you genuinely want out of a business, and for Andrew and I, it was to become financially free. And financially free doesn't mean you need to build a unicorn. You know, if you save as much equity as possible in your business and don't raise a ton of money, actually, you can get a total life-changing exit for, you know, the amount that we sold it for or less. And you don't have to go and build that unicorn. So Andrew and I sort of worked back from a rough figure of what we wanted to sell it for. And it was less than what we originally— what we did sell it for. And we sort of mapped that out over the next sort of 5, 6 years on what ARR we needed to get to, to have a chance of selling it for the value that we wanted, looking at other hospitality multiples of exits. And yeah, we pretty much mapped that ARR and profit out over the 5 years. We tracked that every quarter. And then when we were probably like 8, 9 months away from hitting that ARR goal, we thought, okay, let's speak to a broker. Let's see what they think about the business. Do they think it could sell for what we want?
We took the money and ran. I mean, when, when, you know, we had, we had over 3 offers, I think, that were over $100 million. And at some point in time, you're like, just doing the math, you're like, this is an insane amount of money. You know, at some point in time you take the money and run. But there's a big part of me looking back today, I wish I would've never sold it. I wish I would've never sold it. Like that company today would probably be a unicorn. It would probably be worth a billion dollars. Would you say that you fell in the trap of selling early rather than waiting for longer? You know, I don't, I don't have any remorse for it, but it's just, you know, it's just one of those things in life. You roll the, you roll the dice and figure out, you know, what to do at the time. And it wasn't just my decision. I had other business partners too. They were a little older than me.
The good thing about an earnout is, well, when we exited, so on the Friday, Which was very surreal. And a very proud moment rather than a sad moment. We were in work on Monday, the next day, because we had another 2 years and targets to hit. So this sort of allowed us to ease ourselves out of the business. And then probably like 6 months out from the end of the earnout, you know, everything was in place, management was in place, we'd handed most stuff over to our acquirers. So I think we were able to come to terms with the handover, ease ourselves out, think about what's next. And, you know, after 2 years of them working for someone else on your own business, you're sort of done anyway, to be honest. So not, not that it's— how was it? But you're like, okay, actually, you know, this is why I started a business, because I don't want to work for anyone else. And then suddenly this new acquirer is telling you how to run your own business. So it's almost doubly worse. So by the end, you know, like a year and a half, Andrew and I were like, okay, you've sort of fallen out of love With your baby anyway. So you're like, it's time to let it go. We're excited about what we could do next. And yeah, it allowed us mentally to prepare for having nothing to do with Design My Night.
The plan was get to $10K per month in revenue and try to sell for pretty much a million and start over just the day after. It didn't really go that way because we grew way more than $10K per month. I think when we sold, we were something like $130K per month. And something that we didn't anticipate is all the buyers out there, they were asking us to stay 2 years in business with the acquisition. And 2 years was huge, like was really not the plan. They were asking for that because the, the business was incredibly risky, like Elon Musk was there, he was changing the rules already. Things could just go sideways. Like this guy is like super unpredictable. And then at the same time, like we got like a sister product, which is Taplio, the equivalent of Twitter for LinkedIn. And this product was just starting to bring revenue. But it was not compliant with the LinkedIn rules. So the two things together, it was very hard and very risky to acquire us. And the company who got interested in us, one company from the US, one company from India, it was hard for us to even consider working with them for 2 years without knowing absolutely nothing about them, like their culture until we found this French company. Like I used to know the founder. He was actually in the same class as me in middle school. So when we were like 13 years old and he was a user of Taplio, he was like a customer. So he knew the product pretty well. And it was, it was a strong match because it was, it was like a very small team, 50 people, same age, same culture, same country, same language. And it worked out. We found a way to create this deal where only 20% of the amount of the acquisition amount would be paid upfront. Because of how risky the business is, but then 80% of the acquisition amount could be unlocked with revenue milestones over the next 2 years. What I really appreciated is how, like, how this guy understood that we were entrepreneurs as well, as we, we need, we absolutely need this independence to, to build things and to be successful. And so during the 2 years We got pretty much like, we, we had all the freedom that we wanted to execute the plan and to, to grow. And so that's why it went very smoothly. The issue is that is like to, to give us a lot of freedom, it, it makes it very hard for teams to collaborate together. So we, we mostly succeed, like we unlocked 5 out of 6 of the revenue milestones. We grew from $1.5 million per year to $8 million per year in less than 2 years. But at the same time, I, I think that, I don't know how, but, uh, by working together a little bit more, we could have achieved a little bit more like higher growth, which is very hard because we wanted this freedom.
I can't say that I knew exactly what I was doing at 14, but I was figuring it out as I went and ended up selling that business actually right before I turned 18 because it became so overwhelming as a teenager trying to manage a business. Somebody gave me an offer on the business that was way more money than I had ever seen and thought that, you know, I wasn't really thinking about selling it, but When that number came across my radar, I decided that, okay, yeah, maybe it was a good time to sell it. The first company I started was MediaCatch, and then I invested in this record label called Next in Line Records, which ultimately did not go anywhere. But it did lead me to my third company, which was a company called ShowClicks, which was also in the entertainment space. But it was a lot different in the sense that we were building software for event organizers and venues. And I learned of that or saw the need for that from my experience at the record label because our artists were going on tour and they didn't have any means of like distributing their tickets and promoting their events online. The first business I had happened organically and it And bootstrapped it. And so with ShowClicks, it was a little bit of a different story and something I just did not know. I didn't realize, my thought was like an investor comes in and they have, they want to see you hit a home run, right? They want to see you kind of grow this to as big as possible. That may not be a billion-plus dollar outcome. It may just be something that's Maybe they want to put in a million and their kind of goal is to see the business get to $15, $20 million in revenue and exit for 4 or 5x that. And that's a big success story for them. But if you don't understand that and you end up surrounding yourself with investors that are in that camp, you can create a lot of heartache for yourself, right? But ultimately, Once I realized that, hey, you know, what success looks like for them is way different than what I had really been dreaming of for this, a lot of things started to click and make sense as to why, you know, why they were giving me feedback a certain way and why, you know, they're kind of helping to drive the business in a different direction or something.
Valued my company, I think was $10 million back then, something. The valuation was the sum of all the different ventures that was inside the startup studio. And I evaluate each of those. I don't know the valuation of it, but let's say that one of them was $2 million. And I say the sum of all this is $10 million. So my valuation is $10 million. Um, at some point, uh, I had a deal to sell one of the ventures where we literally put $200K $100K in the company. And after 6 months, we were able to sell it $1 million. So, it was beautiful, like a timestamp, like in 6 months, it was the proof that the startup studio was going ahead and all this. And my investor was against it because the valuation was too low because I evaluate this venture, the double of it to justify the global valuation. And I got stuck with it, even though the deal was splendid.
Maybe I sold too early. Maybe I, you know, exited before I could have grown that into a larger business, et cetera. Um, and I think now also, I mean, I'm less, you know, back then I was more focused on, well, can I raise investment for it? Can I grow it, et cetera? And I'm still there, probably not raising investment, but it's still in terms of I want to grow this. But there's some great statistics. It's like the people that make money are the ones that see the business through for 10 years plus. That's, if you've got the grit to get it through the 10 to 15, 20 years over that lifetime, you will make much more money than most of the exits because you'll be pulling half a million, maybe a million profit out of it a year. You know, do that over 10 years and you've suddenly got $10 million. Well, that's, you know, the average exit certainly in the UK is way below that. So even if you started off with 50% as a co-founder or whatever, you might be down at 10, 20, but maybe even single digits by the time you get to an exit. And yeah, so, you know, I think if you've got a good established solid business, you could actually be taking out more over the long run than somebody that has a good exit or what looks like a good exit.
It's a very risky business in terms of exit, because if you are constantly raising hundreds of millions of dollars, you are diluting yourself, you are handing the power over to the VC. There are terms, you know, when you're raising hundreds of millions of dollars, there will be terms in those term sheets that are not favorable to the founders unless it becomes a decacorn. And I know personally people that have IPO'd All built a unicorn. And actually the founders have taken less money than I did from Design My Life. If you want to build a generational product that changes the world, like your Ubers and stuff, then yeah, okay, you go down that path, but it's a very different path.
Well, I didn't really have a choice because nobody would invest in us. Like when, when we were doing super poorly and I was in so much debt, I was trying to raise money, but it wasn't a venture scalable product. It wasn't a product that people could reasonably invest in, right? Because it didn't have a big market. I was trying to raise money, but at the same time I was trying to make money and I became profitable instead. And then I realized how much freedom you would have when you're profitable, whereas all my friends that were raising money were constantly raising money. I actually ended up selling because I just wasn't having fun anymore, and I was actually complaining to a friend in the industry. Wondering if I could just get rid of this thing, like maybe even sell my shares so like my co-founder would let me move on. Like I was just seeing so much opportunity cost and not doing something else. And he was the one that was like, well, if you're serious about that, maybe we can buy you, but you have to stay on for 2 years. And that was actually how the conversation started.
What drained you and what took the fun out of it? Which part do you think was the— Last straw.
I mean, it's true that I don't like managing people. That's why I'm, I'm a bit of a lone wolf. And luckily, like, we didn't have a big team. Everyone else was on product. So my, my CTO co-founder was managing them and he, he loved that. He was like the opposite of me. I think I just realized that there wasn't potential in the company. Like it was, it was a good company. It was a good business. But it was never gonna be a great business. I never paid myself more than like $4,000 US a month, and nobody on my team ever got a real market salary. And like, it was just, it was always struggling, right? It was like just a super niche product and I could have kept pushing it, but every sale was hard. Like it was a vitamin, not a painkiller.
Buyer's job is really quite different to what you think it is. What they're trying to do is mitigate risk, not look for upside. Good investors mitigate risk. And so what they're looking for is things like what they call quality of earnings. So how much is retained versus projects, you know, how much client concentration is there, all of those kinds of things.
What's the biggest pitfall and how did you structure your deal so you actually got paid what you were worth at the end of the day.
I vividly remember the first meeting that I had with, you know, real money people. And we had corporate dev kind of people come in, not actually from our acquirer, but from one of the other interested parties. And they were talking a language that I just did not understand, quite frankly. And that scared the bejesus out of me. There is a saying in the world, I spend a lot of time around it now, that, you know, never separate price and terms. It cost us a lot of money to sell it. But in doing so, we got really good advice, legal, tax, professional, M&A broker, all of that kind of stuff to get the terms right. We definitely leaned into the kind of the expertise there. And we did things like we had a long earnout. We had sort of 3, almost 3 and a half years because we actually took a deal that most people thought we were crazy for taking in that we took less upfront with a longer earnout, but we backed ourselves to really grow because we'd figured out a couple of really key things about that growth trajectory and thought we'd unlock them. Because as you go along this journey, there's a series of kind of like growth plateaus and we kind of figured out, we thought how to break one of that glass ceiling that we were in. Thankfully that turned out to be the case, but we, so we backed ourselves to grow and we created a bit of an environment that allowed us to really profit from that. And yeah, probably when, if I think about percentage terms, you know, how it ended out, we, we probably only got about. Less, just less than a third upfront, I would say. And the rest of it was on earnout. And yeah, we made sure that we had a series of interim payments. So we didn't wait right until the end to be paid. We had a payment probably after 6 months, we had a payment after 18 months. I mean, they made a payment at the end. So it wasn't all deferred all the way to the end, which I think is really good advice. And then we had lots and lots of really good control clauses in to make sure that ultimately we could control our own destiny and make sure that our acquirer couldn't, for all the right reasons, put too much strain on our P&L for integration reasons, for instance, and that kind of stuff.
It was less about what we got right and more about what we were forced to get right, because investors didn't want to fund us anymore. So investors basically were like, you've had a long time trying to build this like consumer-facing food app. And we haven't seen the money. So we're not going to give you any more money.
So the pressures were coming already from the investors?
Oh, absolutely. You know, it was 2014. 2016, massive pressure of like, you're not going to get any more money from us. And that made us really focused of like, oh, actually forced us basically anything that didn't make money. I just said no, I had to say no to, because I had, it wasn't like a, it wasn't, I would have loved to say yes to all these things, but I really had no choice. I had to say no. So, and then people would come to me, like big companies and go, hey, can we work with you and do a free trial? And I'd be like, we don't do free trials.
Sorry.
And it worked. It's amazing, right? So the confidence or the cheek of asking for the money comes out of desperation too. So I think it was really like, you know, that forced us to make money. With money, you can hire smart people. I hired some super smart people in sales as well, who like understood how to price stuff. And then we were able to go for much larger contracts. Literally, we were like 100x-ing our contracts. So I, and that was like, and I was like mind blown. It's like, what? Like, there's no way we can get this much money out of these people. But they said yes. And actually, it turns out you need that kind of money too. If you really want to be serious and build something really serious, you do need those kinds of sales contracts. But it felt weird to me initially. Again, as you start to do it, you learn it. And people can tell you and you can go, yeah, that sounds right. But you have to kind of feel it and experience it. And once you felt and experienced it, it just kind of like, the momentum carries on. So we basically, you know, we became profitable. And at that point, it's kind of weird as well. We didn't try and sell ourselves. Like, I never went and contacted a company and said, hey, do you want to buy me? We just suddenly had literally probably like 5 or 6 large companies all asking to buy us. 3 of them put like, literally flew in M&A teams and like tried really hard to buy us. And then, and it was like, I was like, sure, you can come and talk to me about buying the business, but like, you know, it's not something I'm like actively trying to do. We initially, you don't know they're actually looking at M&A, but suddenly they like want to fly in 5, 10 people to Birmingham to our tiny little office. And I'm like, we've only got like 2 people in our office, like really? And like, yeah, yeah, we want to come into a workshop. You know, we're going to bring like all sorts of people with us, translators and all sorts of stuff. And I was like, okay, sure. And then it's only kind of like 3 or 4 months later, you realize that, oh, I think they're like, I think they want something more than just like, you know, a SaaS API agreement. And then, you know, we had that, they all kind of in the same 6 months, suddenly all these companies wanted to work, started talking to us in this way. Ultimately, we chose to go with Samsung because for a few reasons. One was they had a super smart team. So it was a guy called Travis Bogard was like the head of this new Samsung Next division. He was previously a head of product for Uber. He had a really good like track record, like sort of history of building tech stuff in Silicon Valley. And he had a great team behind him too. He had like leaders and these other like leaders from companies I really respected. And I never had had the opportunity to work with before. So he was like, the team there was wanting to buy us and I really wanted to work with them. I wanted to learn from them and learn how they built stuff. So I was like, that was really attractive. And then also Samsung's distribution. So like they wanted to put our app across hardware they have. That was really attractive. Suddenly, you know, the users that could access our stuff, we could build something much more meaningful. And then of course, the money was good too. It wasn't actually in financial terms, the best offer alone. There was some like attractive parts of it, like, you know, all cash and stuff like that. But it wasn't like the biggest number. But it was when you kind of, you know, we spoke about this with my other team members. And I was like, you know, actually, think on balance, this is probably the right deal to go for. And I think it absolutely was.
Not many founders experience an acquisition and sometimes it comes with a few strings attached. So I wonder what yours were.
You're right. There are always strings attached. So we had an earnout, which means depending on the performance of the company over 12 months after acquisition would depend on how much cash and equity So we were not hired full-time, but we were basically hired as advisors to work and make sure the product and the service continued to grow. And this is where we were incentivized and we worked. And so we weren't selling a lemon, we were selling something that actually had some legs and traction. And so the whole team was very involved. And I can say, thankfully, we hit all of our milestones so that we received our full earnout.
It's very typical in service-based businesses to have what's called an earnout. So it's a period of acceleration of your capital, or often you can earn a bit more than the headline figure of the deal if you hit certain numbers, but also you can earn less if you don't hit them. So it's a bit of a caveat. Now, I negotiated something a little bit different. It wasn't my first rodeo. I've sold 2 other businesses prior to that business. So I negotiated that I would get some group-based stock in the larger mothership company that acquired me, but I didn't have an earnout at all. I just had the headline figure. I cleared off majority of the cash upfront, and then I traded the other part of the value into group stock, knowing full well that if I wanted to exit, the group stock would be as valuable, if not more valuable, because they had a huge acquisition spree that they were on. So when I came to finally exit, I was paid out based on group value. Not on my individual agency value, which actually, to be honest, was a, was a good thing at the time because they'd grown as a group much faster than we did as an individual agency. And then when the figure finally came, it was a bit of an anticlimax and a bit weird because it was a Monday afternoon, I was still at work, I had to go straight into a big presentation with the team literally like an hour after the money hit my account. It was just the most bizarre. They didn't know, couldn't tell them at the time. I was like, Jesus.
I knew that I wanted to build the business to sell from day one. I didn't know what the timeframe on that was. About 3 years ago, my daughter had just been born. I've had an itch for a while to get my teeth stuck into another business. I'd been in the marketing and advertising world for around 10 years. Daughter was born. And so I started flirting with the idea of why don't we see what the business looks like if we are going to sell it, what it's valued at, how much interest is there? And so I started working with an M&A consultancy for agencies. And eventually we had the conversation with Velstar. And from the first call, there was a great connection with them. And that's of course who we eventually sold to. So it was mainly a case of I felt it was time to go in and the offer was great. So I had a 9-month earnout, which is relatively short. And actually, we got to month 8 and I said to them, look, I'm not really adding any value anymore to the business. It doesn't need me.
The company I'd sold into expected a pound of flesh because they'd spent a lot of money and they wanted a lot of my time, hours, and attention and focus and wouldn't allow me to take my foot off the gas and neither would I anyway. So it felt for 3 years after the exit, like still full throttle. It didn't feel— obviously I had numbers in the bank, but actually In the end, when you have that type of capital, you have to spread it across lots of accounts, you have to invest it, you have to make a lot of decisions, which again are quite heavy things to try and figure out. Wasn't taking breaks, wasn't taking holidays, and I had some bad burnout. So I felt like if I wasn't still holding on quite tight in those first few months, like the wheels on the bus might come off. And I'm like, you know, I need to justify the the sale. That's how I felt, probably wrongly so in hindsight. But so the first few months were very pressured. And I really liked the team that I'd sold into. So I spent a lot of time, felt comfortable. I was in a co-CEO role, the other CEO was excellent, spent a lot of time getting to know him. And then we kind of went on this fun journey of trying to grow the business together, trying to change it, the structure changed a lot within 4 months of selling We completely rebranded the business completely, um, that I'd built disappeared from the public eye. You know, we became this global entity which I'd sold into and all that legacy, all that work kind of just dwindled away, you know, on all the social media accounts just disappeared. That side of it was quite emotionally draining and strange, bizarre. I knew it was, I think it happened quicker than I expected. And then I was in this new world with 1,300 colleagues. All my team members, you know, were in this new world. They were in Brazil, you know, in South America, completely different kind of way of operating and doing things. And yeah, it was bizarre, but an enjoyable process, I have to say overall, and being part of that bigger entity, you know, it comes with challenges, but also I learned so much by having exposure to that structure. It's funny, you know, as a founder, you peg yourself to your business, don't you? And actually, as an entrepreneur, you know, it was the thing that I'd built that I'd been most successful at. And it gave me that kind of validation, internal validation, external validation. I'd won awards, I'd done all these things. And then all of a sudden, the brand's dead. It's gone. So there is this kind of mourning process that you go through, trying to refine purpose. And yes, it's a strange thing. It is a really strange thing to go through. But You just have to keep reminding yourself that again, nothing is permanent. It is part of the process. And I always, I've always been entrepreneurial, you know, I've had multiple businesses now. So I knew I would go again and I'd do something and it's just part of the story. You know, you're very grateful and humble and all of those things about the fact that you've managed to achieve something that most people do not, but there is some pain through the process as well.
I think there's a couple things there. Like people always ask, like, you know, it was your baby and you sold it and how does that make you feel? And what I usually tell people is like, she's not a baby anymore. It's like she's 21 and like running out into the world and like has a boyfriend and like they're doing all sorts of things I probably don't approve of anymore. But at some point in time, you're like, I've done this for so long. It's not my baby anymore. After many, many years, it's like, I'm fine. You detach from it. You know, when you're first trying to get a startup going, yeah, you're very more emotionally attached to this thing. You're trying to will it into existence, right? Like you're the only one that has the vision to make this thing work and you're trying to just make it happen. And then eventually it takes a life of its own. Eventually. Not many people talk about leaving. And with 2 departures on board by that point, what was the hardest thing emotionally about stepping away?
I think it's the fact that you feel like you poured everything into your business because you do. Entrepreneurs don't shut off. their work at 5 or 6 o'clock in the evening. They're— it's always on. You very much pour your life into it and everything around you takes some sort of sacrifice because of that. And so when you get to that place where you're starting to think about, or you're moving forward with moving on, there is a— there is a letting go that A process that I think is, yeah, it's not talked about enough, but it's, it's, it takes a while that really makes you kind of question a lot because you, you almost question your own ability, even though maybe like, you know, in my case, my last company was wildly successful or is wildly successful.
It—
the fact that you feel like you kind of work yourself out of a role or you just poured all of this time and many years into it and now suddenly, like, you're kind of restarting back from ground zero. I don't know. There's a sense of imposter syndrome because you're, you're wondering, like, you know, why, you know, why do I no longer feel like I'm a fit in my own company like that? I designed You know, and I spent so long investing in. And so it, there's, there's a bit of it that, that, that like impacts your, your confidence level. And I think the second time, like with, with, with the zebra moving away or moving out of management, it was a little easier because I'd done it once before. And I went into it knowing that I was going to go through this process. of like detaching myself, trying to stop my head from thinking about it all the time and just trusting that, you know, there's new hands that are kind of taking care of my baby and they're going to do much better than I could at this stage. And so when you realize that, like, you're— some folks are just like me, you know, I'm not— I don't think I'm that person that's going to take a company that's at $100 million and take it to a to, you know, $10 billion. Like, I, I'm more, you know, 0 to 100 sort of thing.
You've sold twice. What did you misunderstand about exit before the first one? I think what is hard to understand is how it changes people's perception about you and relationships, family relationships, family dynamics. Is that because of the money? Yeah. I mean, all of that is the part that's hard to understand.
Okay.
It has a, a dramatic effect on family and friends in an all negative way. No positive. Is it because expectations change or? Well, I mean, I'll give you an example. Like nobody invites me to their house. They know where I live. They know I live in a, in a super nice house. They're not gonna invite me to their house. It, it changes weird dynamics with relationships with people. And it's like, if you want to go out to dinner with family, you're buying or you're going to Taco Bell.
And I'm guessing they didn't get any easier with time either.
I don't, nothing's really changed from any of it over the time. I think in some way you, You figure out who your friends are and who your family really is. And like a lot of people, I have family members I don't even talk to. Um, and your friends change over time. I think that's the big thing is you find, you find some new friends that you have different, you know, shared experiences with. It's a lonely place to be an entrepreneur is what I will say. It's a very lonely place. Very few people understand the problems that you're trying to deal with or The solutions to them. And you're just thinking at a different level usually. And, you know, you go hang out with some random guys and they just want to drink beer and talk about sports or something. And I'm thinking about like some crazy business problems and they just don't understand. Like they just don't relate at all.
Right.
So you have to find new friends. You gotta find new people you can relate to. It totally upends like some of the dynamics, like people that you were friends with your whole life, they're gonna look at you differently all of a sudden.
One of the things that happens when you sell is you hand over, of course, the reins to your business, but your identity, which has been so tied up in that business, doesn't change on day one of selling. I had to spend a lot of time just thinking, what do I want? Who am I? What am I trying to build? What sort of dad do I want to be? Sort of these existential questions that when you're head down building a business, you don't actually sit up and think about. The business is more important than yourself in some circumstances. So I found myself slowly as I was doing that work, finding myself drifting back to the desk to the point that I was like, actually, I really want to build something. When I first got into business, I thought this success for me meant freedom, but actually success for me is building something and building something with great people.
I think it's, it's ultimately it's time, right? It's time and it's relationships. And I would tell you to some degree, being a builder ended up being a coping mechanism, I think, for my previous marriages where I wasn't very happy in the marriage. And So I would avoid her and spend more time working on my business. And I don't know if you call that a blessing or a curse or sacrifice, but it was just the reality. But yeah, you sacrifice a lot of time and everything along the way, and that includes relationships. And I look back where it delayed how early, how young I had kids. Like I waited to have kids a little longer because we were worried about the uncertainty of things. And probably the thing I sacrificed the most is just not spending enough time with my kids or as much time with my kids as I would've liked to. But I would also say that's not entirely the fault of the business. It's because I also have ADHD and it's super diff— like most founders do. We do. Let's not lie about it. My brain is always thinking about something else. And so when I sit down with my kid, My ADHD doesn't want to sit down and play with Legos with them. My mind is thinking about some business problem or some idea or whatever. And that's difficult. And that's not necessarily because of the business. It's because of, I have ADHD, but it's the combination of the two. My mind never stops. And so it makes it difficult at times for me to do things. The struggle is to be present, right? It's like, how do I be present? And At some point in time, it's really difficult for me to do that, but I think it's just trying to create a schedule for you that works. You know what I, what I have long did, it's like, okay, I work till 5 o'clock, whatever. I have dinner, I spend time with my family until bedtime. And a lot of times after bedtime, I would work, I would work more for years. I'd put the kids to bed and then go back to work for years. I think some of it's just trying to get that schedule of like, okay, I've gotta focus. Like there will always be more work. And this is why I tell I tell my kids this a lot because they're worried about how many episodes they watch of some TV show. I'm like, there will always be more TV shows to watch, man. Don't feel guilty because you haven't watched enough TV shows. It's the same thing with work. There will always be more work to do. So it's like, at some point in time, you got to stop and you got to focus on other things. There will be more work and it will still be there.
It's actually fun as well. Investing is fun. And yeah, I might end up making more money from my investments than I made from selling my own businesses, which maybe says I should stop building stuff and start investing instead. And I did some advisory. I just mentored some other startups and helped some other startups. But the main, I was a bit of a weird situation like 2, 3 years ago and I didn't know what to do. I'd finished my thing at, my mandatory time at Samsung, my kind of, they called it a holdback where part of the cash that I was paid for the acquisition was held in an escrow. And if I left the company, they would not give it to me. So I had to stay for 3 years. 3 years went, all the money was paid to me. And I was like, what do I do? And I don't kind of feel like I don't know what to do. I'm happy with, I like the team, I like the mission, I like working at Samsung. It's great. Like why? So I hired a personal coach, worked with that personal coach, kept things like diaries and all sorts of things, did some experiments to try and figure out what do I actually, what motivates me? And I think what the truth of what motivates me is At least what I think, and I still, who knows, I think everyone is still trying to a little bit figure that out, right? I don't think anybody truly knows exactly what it is, but kind of where my current thinking is, is I love the creative process of building stuff. I like, it's also really important to me, like who I'm working with every day. I like to see progress and speed, but mainly I love the creative stuff. I love building stuff and like being like really hands-on. And when you're at a larger company, inside Samsung Food and Samsung, a lot of my role was more politics, which is also, actually, I did also enjoy some of that, but it's also a lot about aligning the whole org to make sure we have the budgets each year and make sure that our overall mission and vision is aligned with what Samsung's is and everyone knows what we're doing and all this stuff. So I started doing more creative stuff outside of work, like started painting and started doing more DIY in the house. And then I kind of realized, I think I just need to do a startup.
What didn't change is probably, you know, the mission of the company and why any of our technology existed. And you'll see the company today, I'm not involved with Prenetics at all nowadays, but they're doing incredible things in consumer health. And I think consumer health has definitely been, was my passions over the years. And I think we just, um, you know, it reached a natural point where actually I was just after the listing and actually before the listing, I had been thinking about this as like, well, I'll probably move on. You know, after, after this listing and take some time off. Primarily, I wanted to take some time off. It'd been a long 10 years of building startups through to that thing. I needed some time to breathe. And I actually think it took me about a year to really decompress after I moved on. Took a little bit of time off and then I had a few sort of consultancy and advisory pieces of work. I was a fractional chief product officer at a health concierge business and on the board of a couple of others. And while I enjoyed that, I actually found myself deeply unsatisfied at not building something. Like I found, you know, really, I'd get very anxious. I didn't find it very easy to just give like meaningful advice to others on their business. I wanted to actually help them do it. And so I had this sort of this dichotomy of, let's say, like, I'm very happy to be paid and do about 7 days of work a month, you know, and have a sort of a semi-relaxed life and so on. I had a young child at the time and so on. But actually, I just couldn't help escape the fact that I really wanted to be in the weeds building something. And that's like I've been brainwashed by my sports career, my startup success to just go again. So the thing I, what I ended up doing was again, being sort of open to opportunity and a few things conspired, which led me to co-found Stride. But really it was driven by this kind of deep unease with not physically building something every day. I feel much more comfortable even going through the uncomfortable parts of building a business. And that's, that's where, that's where I'm currently at right now in the midst of that.
So it was about 25, 26 when you sold your first company. Did it give you confidence? Or did it just like reset your appetite to build again?
Yeah, a bit of both actually. So the weird thing is sold it, had a kind of an earnout exit on it. I was there for a few years afterwards, fairly standard with consultancy businesses. But I had this hubris of like, I'm young, I've figured out how this works. It's easy. Like I'll just do this again. But there was quite a lot of naivety in that because lots of ways I just got lucky. But you put that down to your own skill and expertise and really it wasn't, it was just a bunch of luck. So the next one, and the next one, you know, the ones after that were proving that it's actually a bit harder than it looks.
Andrew and I thought, look, we're sort of early-ish 30s, we're too young not to do anything now. We love building businesses, we love operating. So, you know, going again seemed natural, like, do what we love. I think we knew we could come at it a bit differently. We knew we didn't have to work ourselves to the bone because we were more mature. We'd learned a lot. We also brought in a 3rd founder for Trumpet to be CEO. So he could become the sort of face of the brand and manage the team and the office and all of that stuff that we didn't really want to do. So we, again, we were very deliberate with how we approached Trumpet. We had about 5 or 6 ideas. So we're very good at coming up with ideas. We ideate an idea hard. And I think that's one thing a lot of founders don't do enough. So when we come up with an idea, we don't immediately think of a name and a brand, etc. We give it a project name. So Project X, and then we go out and ideate probably for at least a month or 2 months. And the mission on ideation for us is to prove to ourselves that it's a terrible idea. So if you go out with the mindset that you're trying to prove that it's a terrible idea, you will ask questions differently, you will approach the topic differently. If you're going out to prove to yourself that it's a great idea, you will spin stuff, you will ask the wrong questions, and you will paint too much of a rosy picture for yourself. And then we're like, okay, Do we think there's an opportunity here? And then the other thing we look at is, are we the right founders for this opportunity? So we had quite— we saw quite a good idea in the fintech space, we ideated it, it got quite positive feedback. But then Andrew and I said, are we the right people to run a fintech business? Like, not— it's not really something I can get that passionate about. So we thought, you know, however hard it is, we're like, no, actually, that's not the right one. But Trumpet was the one out of all the ideas that got, you know, super positive feedback. It suited the time, like post-COVID or during COVID when everything was going digital. And ours is around digital selling. So it suited the sort of timeframe. So we could jump on that as well. And Rory, who became our CEO, we'd known for ages and knew he would be like the perfect third founder because he's like a sales guru. So the sort of stars aligned for Trumpet. And that was the idea that we followed through on. Design My Night was pretty much bootstrapped. So we only ever raised half a million from angels and took that to exit. And I'm a big advocate of bootstrapping. I guess why we did it differently is one of the main reasons with Trumpet is the scale opportunity. So Trumpet is instantly global. We need sort of serious money to get this, this going. However, we run the business with a bootstrap mentality, which sometimes winds up our VCs. So, but you know, we haven't just like hired 100 people. And we haven't just spent millions on marketing. Like, we're still very deliberate with everything we do. We'll test with small amounts of money. We don't just hire the person with the best CV and the biggest salary. So we still have the same Thought process. It just allows us to test, I guess, test quicker with money.
One thing that I'm doing, I think different than most people is I, I don't have employees. I have 4 different products right now. For each one of those products, I have been partnering up with one very skilled maker. Like who owns share of the product. So I'm not managing the person. He's a self-aware, self-managed person who I'm working with to find some kind of success. And I think that we are going more and more into this direction of less management because the The, the guy you manage can be replaced by AI these days. If he wants peak motivation and like peak involvement, equity share is, is the must.
By the time I sold, I was already an entrepreneur for 9 years. So I really think that business is like a series of deductions. And, and I mean, so is life, right? It's like, what do you look for in a friend, right? It's like, what do you look for in the next business? Right? It, it's just by doing a lot of things that you don't like. So by the time I'd sold Spacio, I already knew the type of business that I wanted to build and the kind of lifestyle I wanted to have. And it wasn't like this was the product I wanted. It was more like, these are the things that would make me happy as a person, and I needed to find a business and a product that would fit that. After 2020, like everybody has a similar aspiration. Right. So fully remote team. I don't wanna manage anybody. So every, like everyone has to be a contractor, no employees. I want everyone, I want everyone to be there because they want to, not because they have to. And I wanna be able to have that honest conversation and say, hey, you know what? If you're not having fun, you should go and find something else. Right? 'Cause we have a very, very small team and everything you do and everything you don't do is very visible. Right? So I want to build a company. When I say a lifestyle company, Mm-hmm. It means I want everybody involved to have a great life, not just myself and my co-founder, but everybody involved.
Right.
So I also want a product that's not bounded by geography or language or industry because I was so bounded before. And when things weren't good, I couldn't just change the product and go sell it to car dealerships. I had to be in real estate. Yeah. And, and so it was just too limiting. Right. And so, um, I wanted to be able to you know, build a company with friends. I wanted to be able to share my successes, you know, things like that. I wa— I wanted a product that could be sold 100% through the internet. I didn't wanna go to any conferences, live events. I didn't wanna do any live demos, no one-on-one calls, like none of that. So just by having those like 10 non-negotiables, I probably eliminated 95% of ideas that I have, because ideas are a dime a dozen. Everything makes money. But as you start digging, you realize, oh, that, that idea's actually not for me.
Did it tick all your 10 Commandments in terms of what type of new business you would want to be involved in?
It did. It did. And, and that's, that's the reason why I started it. I mean, recently I had to kind of go back on those things a little bit, but It was a good check-in because immediately when I went back on those things, I immediately started hating my life again. It's a familiar feeling that I had in the past, like I was working for my business instead of trying to make my business work for me. In the last year, year and a half, I hit this burnout, hit a wall. I Took a year off and I didn't take a year off like I didn't do anything. I just kind of maintained it. I, I wasn't like actively building the business cuz I, I like actually mentally and physically could not do it. And in the last few months as I'm trying to get back and, you know, get the business back into growth mode, I was like, okay, how can I do that? I know I'll go back into sales cuz sales is my background, but I built this product to have a low price point because it was self-serve. Because I wanted it to be self-serving. But when I didn't know how to get the company into growth mode, I was like, I know, I'll just do something I know. I'll just go and talk to people. I'll just go and sell this thing. But I found myself having all these calls, doing demos for people where my product does the demo. That is the product. So I was getting on these calls to prove to myself That I could be productive and that I could do something, but it, it wasn't yielding the results because that's just not how this product is sold. So I did that for a few months and I realized I'm really going against what I wanted to do in the first place. And then I realized these guys don't even know they have pain. I can't sell benefits if they don't understand the pain. I first have to educate them that they have pain to begin with. Have them identify with that pain and then bring in the solution to say, this is how you can solve that. And it made so much more sense. So we have enough revenue, enough business for me to think we're onto something and enough to give me this false positive. But I didn't wanna see that it wasn't a good business. I wanted to see that it's a good business, so I only paid attention to the signs that are working. I did not pay attention to the signs that it's not working, which is 8 out of 10 people come here and they don't understand what we sell. And then all of a sudden it stops growing. I thought it was my burnout. I thought I caused it, but now I realize it would've hit a ceiling anyway because we were only swimming in the 2%. My, my burnout didn't cause it, but it was because I was in my burnout. That I wasn't in the mental space to get ourselves out of it. But now that I'm back in it, I'm seeing it so clearly.
There was this blog platform that I really loved. It's called feather.so. I was in the process of acquiring that product, which by the way is my, my biggest acquisition so far. Like I've done more than 10, but it's way smaller. $250,000, which is just my personal money, which is the biggest risk I ever took. While I was in this process, something quite unexpected happened is that I just received an email from Beehive, the newsletter platform that I was using, telling me that they would just raise their prices. And I would, I would have to pay 2.5 more from what I was paying. And at the same time, I was seeing here an opportunity to have a little bit of fun on, on Twitter and to just like call them out asking about to like, what's, what's this about? And I did that and I got some traction. And so it started make me think about if there was some space for building my own newsletter platform. And what happened here is, uh, pretty much at the same time, I found this other product that was meant to send newsletters and emails from Notion. So I reached out to the, to the guy and asking if he was willing to sell. And he did, and the acquisition happened. I merged feather.so, the blog platform, plus this other tool to send newsletters and emails, and added all the capabilities, all the newsletter capabilities in Feather. It took way more time than I thought, but we actually got pretty successful with that, and I'm now using My own products instead of Beehive. I'm using Feather to send my daily newsletter to, to 137,000 people.
I'm pretty much full-time now building Strides. I'd call it a preventative health membership. And this was driven by, one, I wanted to build something. Two, I felt a little bit dissatisfied that we never quite delivered on our promise and what I thought we could have built. In the previous 2 businesses, in DNAFit and Prenetics. As soon as we started making revenue, it grew much quicker than I expected. And I realized there's a moment, there's a societal shift happening. And if I don't, you know, capitalize on this, we may lose out.
And what was the experience for fundraising?
It's been a funny experience. I've never really done it before, right? You could easily doubt yourself very much. Every time I got a no from an investor, it felt to me the same as when I used to get, if I missed out on selection for a major team when I was an athlete, right? The same thing. I've done this. I missed out on many, many competitions. And also I was lucky enough to be selected for many competitions. But every time you didn't make the cut, it felt like someone else was saying you're not good enough. And every time you get a no from a VC, It does feel the same and you've got to be able to like take it, learn from it, brush it off and move on. And I think like that could crush you if you, if you, you know, I'm so glad I had this sporting experience of going through that feeling before because it could be very detrimental.
Post-Yatter, as I'm thinking about what am I doing, I essentially created a Google Doc and every business idea that's ever come into my head goes into that Google Doc. And then I started to think about, how do you choose a business? Because post-exit, I'm not really working anymore from a necessity standpoint. It's more, what am I really interested in? And so, I've always been interested in health and fitness and wellness and longevity. And so, I started to think about, what does that look like? And what happened one day was I needed to go get a prescription from the pharmacist. And to get the prescription from the pharmacist, anyone in the UK will probably relate to this experience. You have to fight to get a doctor's appointment at 8 in the morning. You then have to take half a day off to go to the doctor. By the time you've gone to the doctor, had a conversation, gone to the pharmacist, Half a day's wasted. So my brother-in-law's a pharmacist. So I say to him, Dave, we need to meet. We need to get a coffee. So we started talking about, well, what about the world of online pharmacy and private healthcare? And we started to go down the route and that's when we decided, right, I think there's an opportunity here for us to go into the world of online pharmacy.
So we started full scale. I think it was 2018. I needed to hire software engineers for a different company of mine. 3 of my top developers got recruited away. One of them went to work at Microsoft, one went to Amazon. Like, so I lost 3 of my key people. And what I realized is like the cost of those 3 people, I could hire like 10 people overseas. And I'd had a little bit of experience hiring people in Russia and Latin America and different places as software engineers and had good experience. And just decided to give it, I was going to give it a try. I'm like, I got to go all in. I really need these 10 developers to go help build all this stuff. And my friend already had a handful of employees in the Philippines and we decided to create a little partnership. We'll get a little coworking space. Maybe we'll have 20 people there and we'll create a little business out of it. And if we find somebody else that needs this, maybe we can help them. And at that time, he did have one customer. He had one customer that He was doing this work for. And next thing you knew, man, we hired 100 people in the first 12 months. It just exploded. We grew from zero to like $5 million a year in revenue in one year, which was incredible.
To be honest, I took the best practice of things that I learned last time and tried to apply them here. So I've done a lot of the same things, a lot of the same team. My co-founder who had, who had left Whisk decided to join us. Some of the engineers I previously worked with decided to join us. The marketing person who had previously worked, led the Whisk marketing has joined us. The designer who previously led some of the design in Whisk joined us. So a lot of the team members that I previously worked with have come again. So that's good experiences. And that's probably the most important thing was like, who's the team? Do they work well together? As I was lucky because I knew all these people and they knew me and they wanted to work together again.
Well, to me it's, it's very simple. There is, in business, there is nothing better than the appreciation of creation of value. The moment you feel that someone else will create more value than you for your business, then you have to leave. If you don't leave, you're not an entrepreneur anymore. You're just a business owner. And there is plenty of business owners who are super happy. They're not creating value anymore for the business. They just run the business. You're a business owner. An entrepreneur is there because he's the one, the person who's creating the most value for the company. The moment he feels that someone else would add more value at his place, he needs to leave the stage. As simple as that.
I think SCaLE ironically is not massively scalable, right? It's very much a passion project for me. That's our consultancy advisory business. So I'm not looking to kind of perhaps optimize it in the same way that you would ordinarily. I have to obviously understand the privilege of being able to say that. So for me, it's about working with a few of the really right businesses over the long term, you see, and building human connection and helping. Sometimes I'm a counselor, sometimes I'm holding feet to fire, sometimes I'm a strategist. It varies. So I'm trying not to let too much automation get in the way of that at the moment. It was very validating for the lessons that we learned through building our business because first time you do it to a certain level of scale, it's the first time. So it could be luck, but then you see it play the same problems playing out through all other businesses and you realize that there's a way through this. And then for me personally, I was very lucky in that it, I really loved doing it and I think I found purpose and passion and all of those things. And do in that process. People that have exited talk a lot about the importance of finding purpose afterwards because you can't just go and sit and play golf and tidy your garden, right? If you're built like that. So yeah, I was very lucky to have that for a time and really enjoyed it.
I've been fortunate now that what the one thing with the capital allows you to do is to try and avoid some of those mistakes that you have to go through all those, certainly those periods of having to do things on your own. And instead with Unusual, I've been able to hire really good operators and people into the business early on. So even before we launched, we had 10 staff. I'd built the structure that I dreamed I wanted and been able to hire these people. And then we started bringing in clients. So very different to anything I've been able to do before. So that is a luxury, but it's certainly given me the freedom to then still stay strategic. Don't get me wrong, I still feel like there's days where I'm like, what am I doing? 14, 15-hour days. I should be out enjoying the Portuguese sunshine. But I'm not always doing that. But again, it's about that purpose piece. But I'm now connected to 5 businesses and I don't operate any of them. I own part of or all of them. And it's a fascinating thing. I love doing that. I love working with founders. I love Working, trying to solve the problems that happen in day-to-day business. I always try and remind myself it's a privilege, isn't it, to have these opportunities and these problems and these things to deal with. And yeah, that's where I am. It's been a ride. The burnout stages have been absolutely dreadful, you know, to the point where it genuinely was like in a deep hole of struggle. You know, I left home at 16. I've fended for myself since then, lost my mum. You know, there's been lots of stuff along the way. And I've also had the 3 exits, which sounds great and really impressive, but I've had 4 other businesses along the way that didn't work out, a couple of which landed me in quite severe debt that I then had to pay off. And there's been lots of periods of probably more periods of failure or falling backwards than falling forwards. And I think it's important to note that because when you see the highlight reel, it always looks like just a linear line straight to success and earning money, but that's certainly not the case. It's the complete opposite of that. And even now, my partner often says to me, why are you still working like you're You're broke, you know, you still work like every day, like, you know, it's, you have, and I just don't know any other way actually. I think it's this fear of, so I left home so young and I've had to fend for myself from a very early age, this fear of like, it could all be taken away. It could all, like, I still don't feel safe or completely comfortable.










