From a £2.30 Sale to a Billion-Dollar Business

15 Sep 2026 · 58 min · 25 chapters

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In short

Zego’s journey from selling a £2.30 insurance policy to becoming a billion-dollar insurance business, including founder lessons on risk, focus, hiring, scaling, and surviving shocks like COVID.

Guest background

Alex Chisnall interviews a founder (Zego) who started a notepad business at 17 in Estonia via Junior Achievement, expanded to four countries, and by 21 led a team of 22 with $1M revenue. At 22 he moved to London on a one-way ticket with no plan B, built a network via meetups, and later worked in sales for an engineering outsourcing firm before helping build Zego.

Key claims

“Nothing to lose” decisions drive action; ask “why” repeatedly (first principles) to solve structural problems; focus on vehicles/insurance lines with unit economics; scaling breaks processes around ~20 people; hiring quality must be protected during rapid growth; COVID caused an 80% revenue drop in three weeks.

Notable examples

first policy sold day one to Mohammed (£2.30); COVID shuttered restaurants and ride-hailing; Zego’s hourly vehicle insurance grew into a product generating 20–25% of revenue; initial insurance pricing assumptions were challenged (per-minute/unit-of-work model).

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

Chapters

Tap a time to open that second in VO

The Journey Begins

0:00 to 0:57

Explore the early challenges faced by the entrepreneur.

“I also asked my dad to take out the mortgage.”

First Business at 17

1:09 to 2:04

Learn about starting a business in school and its early success.

“at 17, selling notepads to students and eventually took it to I believe like four countries?”

Lessons Learned from Youth

2:06 to 2:56

Discuss the impact of early entrepreneurship on confidence and mindset.

“So what did building a business that young teach you that you still use today?”

Moving to London

3:01 to 3:59

Explore the challenges of moving to a new country and starting over.

“When we did a student company, there was four of us.”

Building a New Network

4:03 to 5:02

Understand how to build a network in a new environment after relocation.

“And then I was very logical, like, where can I go where people speak English and it's closest?”

The Importance of Experience

5:03 to 7:37

Discuss the value of learning through employment after entrepreneurship.

“And how old were you when you moved here, did you say?”

The Nature of Entrepreneurship

7:39 to 9:26

Explore the hidden responsibilities and challenges of being an entrepreneur.

“when you're in environments where there are high caliber people working together, you learn so much more.”

Deliveroo Insights and Insurance

9:27 to 14:01

Insights into the growth of Deliveroo and the insurance market problems.

“What were you seeing amongst drivers that made you think that there could be a problem that was worth solving there?”

Insurance Market Insights

14:01 to 14:48

Explore the unique dynamics of vehicle usage and insurance during COVID.

The First Policy Sale

14:48 to 16:10

Learn about the significance of selling the first policy and its impact.

“We're like, look, we need to record this.”
Show all 25 chapters

Expanding Product Offerings

16:15 to 18:17

Discover the growth of the insurance product line and market focus.

“And when the opportunity is telling you to broaden that vision.”

Challenges of Scaling a Business

18:17 to 20:58

Understand the operational challenges faced as a company grows.

“Maybe a fraction of insurance traditional companies have an app which is half super buggy.”

The Importance of Hiring Quality Talent

20:58 to 23:21

Reflect on lessons learned from hiring practices and maintaining quality.

“And externally, it's like, ooh, they've done redundancies, but internally in tip-top shape.”

Leadership and Team Structure

23:21 to 27:10

Examine the significance of effective team structure in a growing company.

“working very closely with the individuals.”

Future Visions and Company Culture

27:10 to 28:01

Discuss the role of culture and future planning in business success.

“There are ultimately like 10%, 15 % of people who are the pillars.”

Building Team Culture and Future Vision

28:01 to 30:52

Learn about the importance of cultivating team culture and envisioning future innovation.

“But I definitely think about the team, the culture.”

Navigating Challenges as a Founder

30:53 to 35:16

Discover the hardships faced by founders and how to overcome significant business setbacks.

“So in the first five years, so there were twice where, you know, I went home and I was like, I don't have a business tomorrow.”

Adapting Leadership Through Growth

35:17 to 38:22

Understand the need for personal adaptation and changing leadership roles as a business evolves.

“Anything that you'd look back on and think you've made a mistake and you'd go back and change that decision that you made?”

Evolving Views on Success and Ambition

38:23 to 42:00

Reflect on how achieving significant milestones changes one's perspective on success and ambition.

“because I don't know what the business needs are as the business kind of grows and develops, right?”

The Drive Behind Building a Business

42:00 to 43:46

Explore the personal motivations and challenges in entrepreneurship.

“So it's a constantly growing kind of a challenge.”

Understanding Unicorns and Pressure

43:46 to 46:26

Discuss the implications of achieving 'unicorn' status in business.

“And that is an exciting challenge and I love competing.”

The Complexities of International Expansion

46:26 to 48:56

Learn about the challenges and strategies for expanding an insurance business globally.

“But in the UK, I want like, you know, 70 million population.”

Taking the Leap: Key Moments in Entrepreneurship

48:56 to 50:47

Reflect on pivotal moments that define entrepreneurial journeys.

“But that's more like a joint venture kind of a partnership setup.”

Defining the Entrepreneurial Spirit

50:47 to 54:31

Dive into the qualities that define successful entrepreneurs and their journeys.

“So always finish with a quick fire round.”

The Role of Timing and Luck in Success

54:31 to 57:50

Discuss the importance of timing and luck in achieving business success.

“So I truly felt like I'm this incredible guy.”
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Transcript

Automatic transcript. May contain errors.

0:00I also asked my dad to take out the mortgage. I spent that into one project. So six months later, no money, no project left. Bought one-way ticket six months ahead. One-way ticket? One-way ticket. No plan B? No plan B. The day one we saw the policy. It was£2.30, first customer, Mohammed. We invited him to the office, took a photo, gave him some merch and it was like a great moment. You went from a£2.30 first policy, over$300 million. We went from 200 people to 600 people only in six months. There were twice where, you know, I went home and I was like, I don't have a business to do. Second was when COVID happened.

0:37No one was doing any ride hailing.

0:39Alex Chisnall:We lost 80 % of revenue in three weeks. What would you say was like your biggest screw it, just do it moment?

0:57Alex Chisnall:of getting started. I'm Alex Chisnell and this is Screw It Just Do It, the podcast for people who are ready to stop waiting, take action and make things happen. You started your first business at 17, selling notepads to students and eventually took it to I believe like four countries? Yes, that's right. So back in Estonia when I was 17, we just wanted to start a business ultimately. I'm part of a school program called Junior Achievement and started the business, brainstormed for two weeks, came up with the idea of like usual paper notepads, but inside of the covers, we put like study aids, maths, physics, chemistry, and so forth.

1:38And then did the product, became a huge hit, went through the program. And like, you know, before we were 18, it was like, we want to set up a real business and had to wait to turn 18 to then legally set up a company. We set it up and then went from there. And then expanded that to other three countries. When I was 21, had a team of 22, made a million dollars revenue. The most profitable business I've built so far. And it was great fun.

2:05Alex Chisnall:Wow, and you were 21 years old and you had that many people. Yes, yes. Crikey. So what did building a business that young teach you that you still use today? There must be a few things maybe, or one particular thing. I think one thing often is like there's a kind of an imposter syndrome or just like, oh, I don't know, I can't do it. and all that. But when I was like, nothing to lose, 17, we started, had a great idea and went for it. So definitely I carry with any industry, any area I look into, I don't think there's anything that anyone can't do. When it's something new, you're going to do a ton of mistakes.

2:40That's totally fine. But again, you need to be smart to surround yourself with great people. But it definitely has given me that that I've taken forward. Wherever you see a problem, it looks interesting, go in there. dig it. So confidence, like massively? Yeah, confidence in ability to figure out the unknown. And do you have co-founders then or was that just yourself, did you say? When we did a student company, there was four of us. After that, then it was two of us who moved forward to a real company. And after a year and a half, the co-founder went abroad. So I then bought out his share and then I did on my own.

3:16Alex Chisnall:Eventually, you left Estonia and moved here to London, right? How important, in hindsight was it like putting yourself in a completely different environment and how that's impacted the person you've become would you say i think it's been massive like i remember when i was in estonia i did this business it was a huge success but at the same time i did another like four projects that completely failed so i spent all the money there and then um i also you know asked my dad to take out the mortgage i spent that into one project so six months later no money, no project left, still had to continue paying.

3:55But what it did, all of this, the success and also those failures was like this hunger to build a great business, the desire to prove myself, can I have an impact? And then I was very logical, like, where can I go where people speak English and it's closest? So London bought one-way ticket six months ahead and then started to hand over my business to the back then management there. One-way ticket. One-way ticket. No plan B. No plan B. And it was hard because you are starting from scratch. I tried to then do the same business here and it just didn't work. The school system is different. Also culturally, how do you do sales?

4:39How do you approach people? There were so many unknowns. And I was literally back at square one. And back in Estonia, I was like, you know, the poster boy of like kind of a young entrepreneurship. And here, nothing, no one. Right. So it's definitely a character building exercise where I, you know, learned and developed. And just you have to persevere. I just went for it. And then eventually, you know, started building up again and learn how businesses turn here, how culturally things work, etc.

5:09Alex Chisnall:And how old were you when you moved here, did you say? I was 22. 22 by then. Okay. Did you know anybody here? No, not really. I just reached out to the embassy and said hi, but that was it. But no one. And how did you start to build a network or even just get friends, let alone build a network maybe as a first step? Came here and then reached like the meetup was a website, right? So went there, what are the events coming up, startup events, and just went to those. and then again one in 10 events I met a person who introduced me to another person who then was impressed and you know offered me a job after 10 months of trying to do the same here when I you know ran out of money I was like I really need to find a job now and that but so it was a good positive coincidence and then I joined the company here doing sales was that one fine stay delivery that was before that there was a back then quick start global which is a company that effectively you as a company needing engineers would hire on your behalf.

6:14Or like an outsourcing company in multiple countries around the world. So my job was to find the companies to effectively wanting to hire people abroad and doing sales there.

6:28Alex Chisnall:Because a lot of entrepreneurs think about this during the journey of having to go and get a job. having been an entrepreneur and had businesses, how difficult was it to then go and work for somebody else again? Not at all, actually. So one of my questions when I interview people, I ask them like, what's been your career-defining role so far in your career? And because that tells a lot about what they've learned, where, when, all that. and when I think about my career and my job before Zika I would say it was one fine stay because that was where I learned and developed the most so I actually if one day in whichever future I wouldn't mind working for another company or another person or people I don't mind because I think I think it's a bit of a fallacy that you can't learn and develop by working at companies and this sense of freedom, perception of a freedom by being entrepreneur, it's completely wrong.

7:36Like you don't have that, right? And at the same time, when you're in environments where there are high caliber people working together, you learn so much more. You being an individual playing football versus you playing with 10 other people who are all elite, great sports people, you learn so much more. And therefore, I'm a big supporter of both. Like, you want to start the business? Great. Sign up for a long list of sacrifices. You want to, you know, work at the company? Great. Choose A team, A players. That's when you're going to learn the most. And therefore, to me, like, both are great opportunities with their own pros and cons.

8:17Alex Chisnall:Yeah, and I was just having this conversation before that not everybody is necessarily cut out to own a business, right? And have that capacity for risk that everybody else does. you know even chatting to people again with businesses are worth you know hundreds of millions of pounds or billions of pounds and they've still had those days where they're not sure they're going to make payroll you know and and and you say that to the average person in the street they might not realize that's even a thing for any business to have that challenge right because they've never been in that situation exactly it's i mean it's the same i would use like you know if you have a 10 year old and they've got world problems on them they feel big for them And when you're an adult, world problems feel big for you, but the 10-year-old problems don't feel as big for you, right?

9:04And it's the same with entrepreneurship. If the buck stops with you, you carry a lot of responsibility that's not visible, not understood, and that's okay. That's part of the job. And therefore, the rare upsides are also very special and unique.

9:24Alex Chisnall:It's a good analogy. I like that. Um, take me back to Deliveroo. Was that like 2016? Yes. What were you seeing amongst drivers that made you think that there could be a problem that was worth solving there? Yeah. Back then at Deliveroo, we were growing really fast, like 25 % week on week, right? Week on week, not even month, right? Week on week and doubling every, you know, eight weeks. It was wild. And you needed drivers to do the deliveries. And then when we started looking into it, we just couldn't hire enough drivers. And then we tried to really dig in there. Why? Why can't drivers come and easily work?

10:04And we realized the pitch was ultimately, come and work for us. We'll pay you a job. We can't guarantee you income. We don't know when and how the jobs come up. And I need to see your£1 ,000 insurance certificate up front before I interview you. I mean, who would commit costs before interview, right? So we then thought, well, why can't, and super naive, why can't you do it based on units of work? You work, you pay, you don't work, you don't pay. Makes sense. We told lots of people who weren't in insurance, they said it's a brilliant idea. And then we told lots of insurance people, they said it's a terrible idea until one said, you know, let's give it a go.

10:45So that's how it kind of came about. But it was a pure business problem. But it didn't make sense to do it within Deliverrider because one is a regulated insurance company or distribution company and the other one is like a marketplace platform for food.

11:01Alex Chisnall:And how long before you realized that this isn't just a delivery problem, this could actually become a business then? It's been very gradual. I mean, we started and thought, you know what, if we could get like a thousand drivers, that would be amazing. And then we rolled with that and didn't think anything more than that. and then started got to a thousand like oh my god there's actually 10 000 drivers would need that then we realized oh same problems apply in ride hailing and and you know it's just like a snowball that started to grow and you started to uncover the true structural problems that customers are facing with insurance and what are the true you know limitations on an industry side and why and fixing those so it's been very gradual genuinely was initial like you know about nothing to lose just turned 30 nothing to lose we'll give it a go if it doesn't work six months learned a lot great fun right and then it's just like a snowball and if i would be very skeptical if founders are telling that like hey i'm here to do this this this on a retrospect everyone can perfectly tell a story and put it all together and that's the duty of founders to be great at storytelling yeah yeah but i think uh i'll be skeptical if like kind of everyone had this grand plan where they've ended up but you knew nothing about insurance zero so how did you educate yourself i just went to a lot of people like tell me about insurance tell me how does it work and then the very like a childlike mind that you ask questions why why why why why is it happening like this why it's done like this and you know 80 % of answers was just because it's always been done yes and then you start unpicking from that so i think that's a very crucial ability both when you're building something within a business or yourself to ask questions why why why and not stop at the first why yeah like just really try and get it to you know it's called first principles or whatever naming you want to use but they're just asking that question and and that's how you learn a lot and then you realize actually the reason why no one's been doing an annual policy is because third party supplier charges in certain cost structure and therefore it wouldn't be economical but there is no um like insurance legal construct reason why it can't be done for example and then that's you go on multiple kind of avenues to just get to the true answers and the true answers are often pretty embarrassing and silly why things have not been done how many um people do you think told you that this couldn't be done before you actually proved that it could be done i think we had less people saying it can't be done And a lot of people are like, I can't believe it's not been done.

13:38So there was like suspicion that it's so obvious that why it hasn't been done.

13:46But the insurer said no, because the way insurance works is you have a car, you buy a policy, and they sell you an annual policy 365 days. On average, your vehicle across all the vehicles and drivers around the UK are driven 2 % over the year. Okay? very little across everybody's across everybody so most of vehicles are just like sitting there right and um you know there's less like five days per year vehicles are driven so they love that insurance love when vehicles don't move you know insurance loved covid like by the way you know so but but what our pitch was we're gonna have vehicles driving 100 over the time and they're like this is why and you want to charge per minute like cents or pounds like they just couldn't come comprehend that how are you going to able to afford it 10 years later it's a great product doing well and all those myths have been busted that that they all had and today you know we've taken it much further today that product is like 20 25 of our total revenues so you just go and apply all of those principles in in other products because insurance is massive like huge tell us

14:59Alex Chisnall:more shortly but maybe take me back to um first policy you sold um how much was that for and what did the first first customer like mean to you at that point in time yeah i think uh we launched and again because we had such a perfect product market fit which i appreciate does not happen often yeah the day one we sold the policy um and uh there's two pound 30 first customer Mohamed, great guy. We're like, look, we need to record this. We invited him to the office. We took a photo, gave him some merch. And it was like a great, great moment. And then he went and referred other people. One of the best parts of hosting Screw It, Just Do It is getting to sit down with incredible founders.

15:44Alex Chisnall:And once a year, instead of interviewing them one at a time, I bring hundreds of them together. This November, I'm going to be hosting the Festival of Entrepreneurs at the NEC in Birmingham. You're going to be able to hear from founders including Richard Harpin, Ray Kelvin, Juliet Barrett, Piers Linney and over 200 speakers across two days. So if you're looking for ideas, inspiration and genuine business connections, I'd love to see you there. Just go to festivalofentrepreneurs.co.uk to register for your free, yes, free ticket. How do you know when to stay focused? And when the opportunity is telling you to broaden that vision.

16:26So actually, by the way, now we also do personal cars. So all the 40 million license holders in the UK can buy our product. And that's our second largest product now. And we launched it like 18 months ago. So that's grown well as well. So yeah, so we effectively ensure either two-wheel or four-wheel with an engine, either electric or petrol or diesel. And that's our kind of focus. Now, you're absolutely right. And we found this the same. The biggest challenge is what often one of the three top reasons that kills businesses is lack of focus. And I used to wrestle with this a lot more. And after going through all those mistakes, I realized I just have to get more focused.

17:11And in that sense, we did commercial lines as well, fleet business. We then stopped because the unit economics just didn't add up. and a couple of countries as well stopped because they weren't adding up. So it's important as a leader of a business to make those tough calls. They matter more quite often. What matters more, what you're not doing, what you're actually doing. And so it was very clear by looking what are those kind of constituent parts that we built in the business that we can build up on rather than something from scratch. And therefore it was very obvious that our playground for the next three, four years until we get to a billion on premium is vehicles.

17:54Vehicles, vehicles, and build an exceptional product in that space. And then after that, we will go into other lines of business, maybe home, maybe pet, maybe something else, right? So the plan is to build the next generational insurance company that future generations use like they do Monzo or Revolut. There isn't anything in insurance at the moment that is serving those needs. Maybe a fraction of insurance traditional companies have an app which is half super buggy. The other ones just send you the policy documents. That's it. So I think the future generations truly deserve equally good insurance experience like what we've done in banking.

18:38Interesting.

18:42Alex Chisnall:You went from a£2.30 first policy, right, as you say, to raising, I think you told me earlier, like over$300 million, something like that. What changes inside a company as you make that journey that nobody can prepare you for? I think it's the, I've found the hardest when processes and communication breaks as the team size increases. there's there's like kind of a threshold of like 20 people kind of works or like you know five works one way 20 by that time you get 20 everything breaks you need to rebuild your 50 150 and so forth and uh i i just didn't realize those were like the car got stuck in mud like that's how it how it felt then you had to start unpicking this again and then um you know the pressure there's a lot of pressure that comes on when you raise money like i did a big fundraise in 21 150 million dollars and it was like okay the way you're operating now does not apply go go go and you know we hired lots of people who were externally very popular but internally as we added more people things got slowed down things didn't move fast enough became highly inefficient in many areas and it took several years of unpicking afterwards.

20:08So growing too quick to keep pace, the teams. Exactly, because back then as well, a lot of company knowledge was sitting in people's heads and then if one function increased the headcount, the other one felt that, oh, I need to keep up. It was almost like competing for who has, like competing to keep up with the team size. and that's been the biggest policy of success, quite frankly. And now I'm obsessed with keeping the team size to bare minimum and seeing how far we can push it in that way. And that's something that no one really prepares. Externally, it looked like, ooh, incredible, incredible, incredible, but internally slowed down on delivery.

20:54And then a couple of years later, after having to have to correct the team size, And externally, it's like, ooh, they've done redundancies, but internally in tip-top shape.

21:03Alex Chisnall:You're more efficient. More efficient, higher caliber people, moving super fast.

21:11Now this AI, we use a huge amount. I'm very proud of what we built and continue to build, but we're still in insurance. So don't have this kind of AI glamour. That will get busted soon as well, and then everyone will kind of reset. but it's incredible. I'm very excited about the team, the quality of people and how fast we move now. And how much influence do you have

21:40Alex Chisnall:these days after a decade when it comes to hiring? More than ever. Really? Okay. One of my top three biggest mistakes I did up until the big round, I was interviewing every single person and we're like, you know, 180 people. And I was interviewing every single person, part of a process. I then stopped because we had to, you know, move fast. We went from 200 people to 600 people. And I, you know, only in six months. Yes. Triple. Triple in six months. Yes. And I only interviewed, you know, for certain of my roles. Yeah. That was the biggest mistake because the quality bar wasn't held. Yeah. and I got one or two hires wrong and then they went and hired like another 10 people.

22:30And then when, you know, two years later after this, when I was like, we're going to turn this around, I changed the process where I'm going to be part of every single hiring process, other than, you know, operating roles like level one, because there's lots of hiring there. But other than that involved, and I've been religiously doing that for the last three years, regardless of seniority, like, you know, a kind of a junior engineer to like kind of a junior legal person to senior C-level person, I am heavily involved. And by doing so, I will protect the quality of the talent. And it's been day and night.

23:15So to your point, influencing, I'm all over this. and I'm all like in the business as well working very closely with the individuals. Like I don't care about hierarchy. If there's a product manager, there's something interesting I want to know, but I'll go and speak to them. And I encourage everyone else as well. Like it's hierarchies for insecure people who want to protect who you speak to and so forth.

23:40Alex Chisnall:How much have you like then used your, trusted your gut for those decisions? For hiring? Yeah. Hiring is, at the end of the day, like a numbers game. And, you know, they say, statistically speaking, 50 % of senior hires you get wrong, you know, on average in the market. 50%. I couldn't believe it. For, you know, mid-level, you get 30 % wrong. So three out of 10, you just get wrong. Now, your hiring process is an element of, like, helping to reduce that error rate. And there needs to be a rigorous process. So we have a five-step process. It's well thought through what questions are being asked at this stage.

24:24And I ask, in my interview process, I ask the same questions. I've asked like thousands of candidates those questions. So I built a kind of very clear calibration in my own kind of head. And so it's less about kind of a gut. It's more about actually proof points. and then at the end of the day you don't know until someone is actually in the business as well. It's like dating, right? So if there are two people dating and they don't work for whatever reason, they'll go and find new partners and live happily ever after. That doesn't mean that they were bad people because if their relationship didn't work.

25:03Same with businesses. Like certain businesses are where talent buys B people. In others it's A. Of course, the B people don't succeed in where the team is A. And also like depending on kind of industry and interest. So it's like, therefore, hiring is and always will be with humans, a bit fluid. Also, humans change. Their priorities change. Family, friends, like whatever kind of goes through their life that also calibrates that. So I don't think it's ever constant.

25:35Alex Chisnall:Yeah. Now, it's interesting because I've kind of been reflecting on, you know, like nearly 10 years of this podcast I've done nearly 750 interviews. And I think one of the things that I didn't realize when I started was that how many or the percentage of founders who still have their finger on the pulse of the hiring in that company. I assumed, you know, you go from startup to scale up, you hand that off to HR and you focus on, I don't know, you know, whatever. but it surprises me and I've had a number of those conversations and just in the last 24 hours of people who've got you know very substantial businesses that still um and and you know one of my regrets with with it you know I think I'm on business number five now but um was one of my biggest regrets was handing off that function as well I think when we got to like towards 30 people and I just thought all right this is like a traditional like handoff point and then you know Like literally your gut's telling you that this person is massively underperforming, she's never been hired, and then you leave it and leave it because you're like, I no longer look after this.

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26:43Alex Chisnall:And then at some point, I just need to step in here and do something about it and take back control. Because like you said, the bar has then been lowered, right? And that's the new bar. Yes, exactly. And then, I mean, it sounds harsh, but it's true. That, you know, another analogy, like a group of people in a company, often there are pillars and there are walls. In other words, if you think of a house, what holds the house up? It's the pillars. And then the walls, walls, they are to make it look like a room, but walls don't hold the house up. Same with people. There are ultimately like 10%, 15 % of people who are the pillars.

27:23And you have to obsess about it. And having like 10 % or 15 % or 20 % of those individuals makes a huge difference to the success of a company. And you as a leader, you just have to obsess about it all the time, all the time, because that's where your leverage comes from.

27:42Alex Chisnall:Yeah. What do you lose the most sleep over when it comes to the business? I sleep really well, by the way. I go flat and then three to five minutes, I'm… Same. I don't even remember going to sleep when I go to sleep, right? Exactly. So I feel I'm very blessed actually when I speak to quite a lot of people. But I definitely think about the team, the culture. Again, culture is like a garden. It has to be thought through where what plants grow. You're going to have weeds growing. You have to take them out. You have to consciously decide which plants are in the shadows, which ones are in the kind of broad sunlight, all of those things.

28:22And that's constantly evolving and moving. And the same is culture. So I do think a lot about the team, the individuals, the problems they're facing, how they're thinking about, you know, solving the problems, all that. And then secondly, like also spend a lot of time what the future will look like and how can we enable that, you know, autonomous vehicles all over this too. I can't wait to kind of ensure all of them. I can't wait to kind of that to be like millions and millions. and you know it's my duty to kind of as a leader to look beyond and place some bets

29:03Alex Chisnall:interesting and I believe was it today that Uber announced autonomous vehicles for trials in London I think they announced something a couple of weeks ago as well about trials yeah exactly but you know even though like we zoom out that's still small like there's 33 million vehicles in the uk uh probably 350 000 currently ride hailing licenses out there across the country um you know one percent yeah so if they all become autonomous and let's say you double that because people want to enjoy it more it's like two percent of uh vehicles right it's still tiny so it actually needs to become where like a 70-year-old in the countryside just puts in, I want to go from A to B and then does whatever they want to do.

29:56So that needs to be enabled. And as we know, because of the Strait of Hormuz, because of insurance, vehicles don't move. Insurance is like a microchip in a mobile phone. It's a lovely experience if it works and you don't think about it. But if the microchip doesn't work, it's a piece of metal. useless piece of metal insurance is exactly the same across all industries and i find it's very exciting that uh you know it's like uh you're almost like hidden but you're enabling temperature same story we don't think about temperature until it's too hot or too cold if it's optimal you're happy but but if it's not then you really it really bothers you and really like you paralyzes you right and the same is with insurance so it's it's exciting you have the best analogies by the

30:48Alex Chisnall:way of like anyone of a especially like the garden one with the culture i'm like you're good at that thank you it's very kind of you tell me about like some of the hardest times that you've you've had to go through as a founder in the zigo journey um maybe the moment when the version people read about in the headlines that i've maybe seen as part of my research that that look very different from like the reality of the company. Can you talk about that at all? I mean, there's a few. So in the first five years, so there were twice where, you know, I went home and I was like, I don't have a business tomorrow.

31:25And now, you know, then Reflectic gathered yourself and then next day you started fighting and then, you know, by the end of the second day still had a business and had figured out the plan. But definitely there's been a couple of times where, you know, such impactful things happen. Most of the people don't know about it. Second was when COVID happened. So we were selling hourly policies and mostly for food delivery back then and also like ride hailing. You know, restaurants shut down. No one was doing any ride hailing. We lost 80 % of revenue in three weeks. Three weeks? Yes. And I was about to go to raise money, which are like three, four months out.

32:14So immediately, 30 % redundancy. And that was really hard. A, seeing that happen that I can't control and also having to have to make those changes. And then two months later, all restaurants opened. Delivery came back booming. Yeah, yeah. And then the other way, kind of the pendulum swung. Yeah. And then the other one was after the team had tripled in six months and then to unpick that in 22 and 23. That was hard. It was like everyone was doubting in you. Everyone was saying you're the bad leader and all of those things, but you just had to persevere and kind of work through this. And it's hardcore mentally.

33:07Yeah, I mean, I don't think I've ever mentioned it as well, but that, you know, like 2020, and like you say, losing that much of your business, like in 2019, I started a podcast agency, and a

33:22Alex Chisnall:specific model of how many clients we wanted and how much revenue, you know, those clients we bringing in. and it's like really high value clients and we had like the biggest provider of office space in europe we had the biggest zoo in europe all making content with us and then literally overnight lost every client inside a month except one and you just look at those industries now what happened in 2020 like no one was in the office no one was buying office space no one was going to any outside attractions right because they're all shut down and you couldn't even have a conversation with the marketing department because they're all on furlough so they just stopped paying the checks and you couldn't even have a conversation about but here's the contract it was like there is no contract anymore it was a big big reset right again like the the analogy but i own a grand scheme of things i think some of those things are good as well like we were thinking of like a two-year timeline to take our in-office custom service to be more like kind of a offsite somewhere in another location or like just working from home.

34:29I mean, two-year plan that then got executed in four working days, right? So a lot of magic happened, even like cash economy, like completely disappeared because of that. So I think there's a lot of like structural changes that take place. And I, you know, another analogy, when you think of like seasons, you've got like the autumn storms and so forth, like there's loose branches, not strong branches and trees. they have to be blown off so that new ones can grow, right? I think it's the same in the economies and businesses. That's why we have those cycles of like, you know, crashes and kind of booms.

35:02They're both required in order for the healthiness overall to exist in economies. As in business, like you say. Exactly. And I think COVID was a bit of a wildfire in business. Yeah, yeah, for sure. In economy.

35:17Alex Chisnall:Anything that you'd look back on and think you've made a mistake and you'd go back and change that decision that you made? I made so many mistakes. I think I still make constantly mistakes. But I don't, I generally operate on a kind of a strong opinions, loosely held principle and decision making as well. If you're at this moment, you're making a decision with information available and then time goes by and you realize it was the wrong decision, then fair enough. now like make a new decision to fix that and i don't think it's fair to like kind of hold yourself and then kind of beat yourself up about some of those things because you you generally as long as you had good intentions you tried your best right yeah um and like you say you're dealing with the information at the time right which yeah exactly so therefore like this i made lots of mistakes where i you know on hindsight i maybe didn't look at the information well enough or didn't didn't dig deep enough but you know it was what it was right for me measure is like am i embarrassed about how i operated like six or 12 months ago and if i am embarrassed i'm like okay that's been good progress if i feel like okay actually it's the same then i'm like am i developing like quick enough fast enough to become better so so i don't necessarily i don't have like regret there's been laundry list of mistakes, some bigger, some less, some that are literally in tens of millions, right?

36:50But they've made me and the business who we are. And as long as you embrace those learnings in your next decisions, next steps, that's what matters. And to your point, you've obviously had to change as a person.

37:13Alex Chisnall:what do you think you may need to change to become the person that you need to be to take the business where you ultimately want to take it if you follow my line of thought yes i i say that like i've been hired and fired seven times at ziga you know metaphorically speaking because the job has changed so much and you do have to reset and that mental model does help me like okay, I got the business here, but that doesn't really work. So I need to fire myself. And I now need to hire myself again, but recontract with myself that what are the expectations? That mental model has really helped because when you start the business early on with a handful of people all the way, what, 370 people, you're doing different roles, different jobs as you go.

38:06So from...

38:10sorry, I lost your question.

38:13Alex Chisnall:Yeah, about becoming the person that you need to become to take the business where you ultimately want to take it, yeah. I think I, I don't think I know the answer fully because I don't know what the business needs are as the business kind of grows and develops, right? There will be different challenges. But I think I need to be always adaptable, always open-minded to very quickly kind of build on certain skills. Like, for example, now I'm very actively kind of in pricing world, very actively much more in product world, because I know that those skills really help to drive the business forward.

39:02But those are two areas that are critically important over the next 12 to 24 months for the business. So I need to be knowing they're enough to be dangerous, to be really challenging the team, working with the team and all that. So I think they come in waves of certain what the business's requirements are that I need to be adopting to.

39:24Alex Chisnall:Anything that you've changed your mind about since starting Zego? yeah i mean um one thing we idolize a lot of kind of uh ceos and entrepreneurs and i'm like someone in delt is like it's me it's me i'm like well it's not often it's the teams behind them that are they just had the initial guts to go for something and um and they've been clever enough smart enough to attract talent, great talent, and keep them that ultimately makes the business success. And definitely, I thought that those individuals, leaders are incredible, but yes, they are to the degree, but it's not like the success equals that.

40:19There's a ton of people that actually have to be doing exceptional job. So that's one. Um, hiring, I, I, similarly to what you described about yourself, like the importance of hiring, I, um, it was, it was kind of a, it was more like, uh, you know, we need to do finances, you know, one of those things you just have to do. Whereas it is like top two, top three priorities for me all the time now.

40:48Alex Chisnall:If you look at the headlines when you research Seago and yourself, um, you've already built a company with a billion dollar valuation, right? Does achieving something that big make you even more ambitious or does it completely change what your definition of, I think I know the answer, but does it completely change your definition of what success could be? I think I'm like, I say like, I can't live with what I'm doing. I can't live without what I'm doing. It's a borderline of addiction. It's a borderline of obsession, right? And why often people don't sell their businesses? Because they're terrified what comes after.

41:35Because that kind of intensity, stress, you name it, has been keeping them healthy. You take that away, like they don't know what to do with themselves, right? So, and I think like to me, it's just a, like a base camp of a base camp, you know, imagine we're climbing Mount Everest. Like, can I get to base camp one? Great. Okay. I got to one. Can I get to two? Great. Can I get to three? So it's a constantly growing kind of a challenge. And maybe initially you try to kind of prove it to people around you. now I'm like can I do it? I'm excited to see do I have the skills, abilities to hire people build products with teams to build something incredible and that is just fascinating and that's the driver for me I don't really like I'm not kind of a money motivated as such of course everyone wants a certain kind of a lifestyle yeah that gets resolved but like at the end of the day like i just want to see people enjoying the product when i did my first notebook business that was like i got very emotional because we we made the products make once a year for school season put them into the shops and then you can see all those kids and parents opening and looking them like Like, mom, look at this.

43:09This is cool. I didn't see this. And this like seeing the satisfaction, excitement of the product you created, knowing what went in there to create this just was an incredible highlight. And I think that's what a lot of founders as well, those kind of peak moments that like, that you live for. And mostly it's a kind of a challenge with myself. like can I build a company that is a generational business that generally solves problems for millions of people in the UK? Can I do that? And that is an exciting challenge and I love competing. I love all of that and that's what it ultimately is.

43:54Alex Chisnall:Ask a mutual friend a similar question like Stephen Mendel when you got that acquisition of the business for Double Unicorn. What did that mean? and he was like nothing I was like what do you mean nothing and he went that particular phrase you know like unicorn double unicorn the exit doesn't actually register anything with me you know yes again um it's great to um just to sell the business for x amount of money and uh you know it's enabled me to buy you know another place down near me and in in sandbanks and dorset have a nice you know family home and but ultimately that just gives me more options it gives me more more time and more options to choose what to do with my time.

44:36But he said that was never the aim.

44:40Alex Chisnall:So whenever that came around and people asked that, he said it doesn't actually register. Yeah, I think if I could, I would not have a unicorn status. I would have like 10 pounds less or something, you know, just so it wouldn't be. Because it actually comes with a lot of pressure, expectations and connotations, attracting potentially wrong people and all those things, right? so and it's not actually very helpful so but yeah I mean funny thing was when the money landed on the bank account it looked the same size because banks the way they signed their software is like the cell size is the same but whether you got like I don't know five numbers or seven numbers they just made smaller font then but really otherwise nothing else really of course then it's like there's In our case, my case, it was a pressure to now drive growth.

45:37And then you just went to do some pretty silly things. But otherwise, yeah, I think it's like funding grounds often are like petrol stations on the way to somewhere, like to Europe. You just stop in Paris, you stop, I don't know, Berlin, you fuel your car, but it's not the destination. At the moment, it's a destination. I think you're moving in the wrong direction. And you said the mission.

46:06Alex Chisnall:Is there a destination as well? Is there a particular point? I want to build a Viva Admiral combined household name insurance company for future generations in the UK and also maybe beyond. Insurance is super complicated internationally, so we can talk about that separately. But in the UK, I want like, you know, 70 million population. I want ZEGO genuinely be the household name that like, they don't even think about that, how easy it is to have all the insurance needs served. And I truly feel that like, like the future generations deserve that. And I think it's, I, and we are one of the companies who are the most well placed to kind of achieve that.

46:54And I have this sense of responsibility, I feel, to not to F it up and actually, you know, try and achieve it for the future generations. And that's the aim.

47:05Alex Chisnall:Sounds like you've got the ambition and the energy to do that. Yeah, tell me a little bit about internationally then. What have, what are you doing? What are you not doing? What have you thought about doing? Yeah, so initially I thought like international expansion is like super straightforward. and at some point we were in like 12 markets. But insurance at the end of the day comes down to your claims. So if I sell you a£100 policy, after that probably around£65-70 depending on the product is to pay out the claims. So that really matters how well you do that and that really varies country by country.

47:52In the UK, the largest loss we have is 24 million pounds. In Europe, the maximum loss you'll ever have is 10 million. In the US, it's like half a million. US is a very litigious country where everything is lawyers, whereas here, like very marginally. There's a lot of nuances. So you really have to go super deep in each of those countries in order to do that really well. So therefore, you have to really go deep. And going deep, it's lots of hard work. However, I would expand and we are actively exploring that with our technology and to partner up with someone. So because we have built an end-to-end operating system of an insurance company that we do everything.

48:36And it's like incredible and super fast, super slick. And if we partner up with another insurer who then handles claims and provides the insurance capacity and then run all of that business in our own infrastructure, that's something that we're looking into already. That's the way to do that. But that's more like a joint venture kind of a partnership setup.

49:01Alex Chisnall:Like you said, there's different ways to get there, isn't there? You can acquire companies who are already operating in that space as well, right? Okay, last couple of questions and then we've got a little quick fire round. looking back across everything so from like the notepads when you're 17 through to building Zigo what would you say was like your biggest screw it just do it moment like the decision where you've stopped acting you stopped like waiting procrastinating and you've you've taken action and there might be more than one of those but one was moved to the UK I was like look just something's telling me I need to be abroad and in an international location.

49:44That was that. It was like, yep, buy the ticket. Let's go. One-way ticket. Yes, exactly. And then second one was we're starting Ziga. I remember very clearly having a conversation that, look, we are 30, well-paid, exciting job, but at the same time, we got nothing to lose if you do it. The worst thing happens six months from now. We're just not paid ourselves, no salary, no income, worked really hard, and that's it. And then you'll go and find another job. So actually nothing to lose. It's like, let's do it. And now it's that, let's go. And I think that's been it too. And I encourage people thinking that way because the risk is actually pretty minimal.

50:32Alex Chisnall:And the younger you are, the less risk is. You haven't got any responsibilities. Yeah, you don't have the expensive lifestyle that you need to support. That's the biggest problem. That's the biggest challenge that people fall in a trap to. They have their fixed kind of cost base so high that they just cannot get away from it. Yeah, yeah. No, I agree with you. So always finish with a quick fire round. So it's whatever comes to your head. No right or wrong answers, okay? What would you say an entrepreneur is, your definition? A builder, a greater, someone who loves to bring something else in their mind.

51:06to life, I'd say. What about a scale-up business? What is a scale-up business? It's like a business who's gone from zero to one, and now they're going from one to 10. They're like, they figured it out, the kind of things at the moment, because the world moves so fast. So at the moment, they figured stuff out. And now there's like, how can we do more of the same and move really fast? That's a scale-up.

51:29Alex Chisnall:And which entrepreneur do you admire the most? And that can be like historically or somebody that's come on your radar and you started following them? There's a ton of founders who are like, they built exciting businesses. But I guess I said earlier, like often of them, there's like a whole team behind them. So I don't really like to kind of glorify them. Again, the ones, you know, you maybe hear more about, they're just doing more press. Half the time, they're just doing press. So I wouldn't, but I have a lot of respect for founders and businesses who take really hard problems, who solve like hardware, software problems combined, like people in defense, people in energy.

52:09Like these are some like hardcore, this is like chewing metal, right? You've got software problems combined with hardware problems, right? And also add regulation on top, right? Software, hardware, regulation, I have a huge amount of respect for people who kind of pick up some real big problems and go and solve for those.

52:27Alex Chisnall:I like that answer. What film has stayed with you or had an impact on you, your life? I often watch a movie like one and then my wife loves to watch movies, multiple, same movie many, many times whereas I'm like once I'm done. But the movie I watched the most is Inception. Ah, okay. I think there's something like, it's on the borderline of reality and creativity and I find that that's been a movie I've enjoyed watching every now and again. That's a cool movie I need to re-watch, yeah. what's something your parents taught you that you've carried through your life i think like uh one is sales my parents are both pretty good sales people in general like maybe that comes with like you know ability to explain persuade you know motivate all that um but um yeah that's probably the first one are you into your music i am but i'm more like a pop pop boy so can you pick a song that best reflects your journey so far maybe that's like i think it's so far it's like backstreet boys as a band this is where i like do my best focus work with i put on backstreet boys playlist and there's the best focus work and uh everyone's got their jam yes exactly so several songs by them okay i've been a guest on the show um you don't have to give me your answer now.

53:51Alex Chisnall:Is there anyone you'd recommend as a future guest that maybe people haven't heard of but have got like a really good screw it, just do it story? Stream founders are building an incredible business. So they are great two guys that are also super funny and smart. British and American, put them in a room. So much fun. Okay, sounds good. last question finally when all is said and done how would you best like to be remembered I don't really care whether people remember me as such as an individual I just want to make sure that like if I interact with people I've interacted in general that like they come out net net positive so I just want to be like a positive impact on society and people I interact with so So pretty low kind of, I don't care about, like when I was building my own business when I was 17, at some point I got to the place that like, I felt like everything I touched turned into gold.

54:59So I truly felt like I'm this incredible guy. And then, you know, five projects completely failed and then reality hits home. So I'm very pleased it happened early on in my career. So I, therefore I'm kind of like, like I want to do something I enjoy, something that's fun and something that has an impact. And if net-net people come out from interacting with me and the products companies I build are positive, then it's a win.

55:24Alex Chisnall:It's interesting. And I don't think it's happened very often, but there's a few people I've chatted to over the years and they haven't started a business till maybe their 30s or something. And the first thing they start is successful. And then they then exit it in their mid-40s or 50s. And then they go and try the next thing. And the next thing fails. and they're just like absolutely gobsmacked. Like how can it possibly fail? And they try something else and that fails as well. And it's like, right, that's it. Yes. Time out. Exactly. And then literally the success rates are like so small. First of all, to building a successful business, like odds are all against you.

56:01And yet you're going to have a second home run. I mean, nearly, it's like very, very slim odds, right? It literally is like tiny, isn't it? 0.00. Exactly. So I think there's the humility and realization there is very relevant. And, you know, people often think it's just them, but it's more so. It's the timing. It's, you know, which is all macro, right? Yeah. And then, you know, a good, healthy amount of luck and then relentless work, right? Yeah. So you only actually control one of the three.

56:42Alex Chisnall:so timing's everything right that's something i was reflecting on last night with so many of the people that i've interviewed and and you know them you know some people say there's no such thing as luck some people say you know the harder i work the luckier i get um but i think so much is timing yes yes like i mean who who knew like even ziga when we started insurance wasn't popular like all those companies that are currently getting funding or got funding a couple of years ago, they were going three, four years before. Or the founders or the core founding teams were in that problem several years before.

57:18And people, you need to be ahead of the wave. And you don't know when the wave is going to hit to then like take defense, right? Very unpopular. There's a bunch of energy, not popular at all compared to now. So you can't forecast those. And if you're like, okay, defense is popular. Let me go and start doing it. you're already late. So I think timing is something that you can't control and therefore you need to default to what you actually enjoy doing and follow that. Massively. Good advice.

57:50Alex Chisnall:Stan, thank you very much indeed. That's an awesome conversation. Thank you for having me. It was great fun. Thanks for listening. And if today's episode has inspired you to take action, why not take the next step? Come and meet me at the Festival of Entrepreneurs this November at the NEC in Birmingham. them. You'll be able to meet many of the founders you've heard on this podcast, along with hundreds of ambitious entrepreneurs from across the UK. I'd love to see you there. So just go to festivalofentrepreneurs.co.uk to register for your free, yes, free ticket.

From the publisher

From a £2.30 first insurance policy to building a billion-dollar business.Sten Saar started his first business at just 17 in Estonia. By 21, he had a team of 22 and a business generating around $1 million in revenue.Alongside the success came painful failures. After putting money into projects that collapsed—including money his father had raised against his own home—Sten bought a one-way ticket to London with no Plan B. Years later, while working at Deliveroo, he spotted a glaring problem: delivery drivers were being forced to pay £1,000 upfront for annual insurance before earning a single pound. That problem became Zego.

The first policy sold for just £2.30.Zego went on to achieve unicorn status and raise more than $300 million. But rapid success brought an entirely new set of problems:• Tripling the team from 200 to 600 people in six months—and why Sten considers it one of his biggest mistakes• Losing 80% of revenue in three weeks when COVID hit• Metaphorically "firing himself" seven times as CEO as the business outgrew each stage• Why reaching unicorn status is merely a "petrol station on the way" and never the final destination

Key Takeaways

• Growth is only valuable if the organizational culture and quality bar underneath can support it

• How asking "why?" repeatedly uncovers multi-million pound market opportunities

• Why founders must continually "fire" their past selves to evolve with the company

• The power of defining the worst-case scenario: "Nothing to lose. Let's do it."

🎧 Listen to the full episode of Screw It Just DO It

🎟️ Join us at the Festival of Entrepreneurs, November 3–4 at NEC Birmingham👉 www.festivalofentrepreneurs.co.uk

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