Nick Telson, Co-Founder @ Trumpet & DesignMyNight

Welcome back to another episode of The Graduate Guide. Today we're joined by Nick. Nick has been the founder of many well-known companies, he's an angel investor, and yeah, he's also a podcast host. So Nick, welcome to the podcast.

Thanks for having me.

If you could just start off by giving us a quick run-through from your, your side, your, your journey so far in your career.

Yeah, I'll try and make it as short as possible. So I At uni, I went to Nottingham Uni, studied languages, so nothing to do with business. I did Spanish and Portuguese. Then, as soon as I left uni, I did a graduate scheme at L'Oréal in the marketing sphere, worked my way up there, so stayed there for 4 or 5 years, became marketing manager of one of their brands, then decided to leave that in my sort of early to mid-20s and started Design My Night. Which was a 9-year journey to exit. And yeah, we were lucky enough to exit that in 2019. And then since then I've been angel investing in startups. I invest in about 50 startups at the moment around the world and have gone on to sort of found a few new businesses as well.

Yeah, there's so many places we can start this interview, but really want to start the, the core of your journey, which is entrepreneurship, right? And obviously you graduated from Nottingham and initially entered a more corporate career. Was it something you always knew you wanted to do? Was it something when you entered the corporate career you found out, oh no, okay, I need to be doing something for myself? Like, how did that, uh, Design My Night come about?

Yeah, like, definitely not. So I didn't always think I was going to be a founder, um, and this was, you know, over like 12 years ago now. So, you know, being a founder and startups weren't as big a thing in the UK then, um, where now you know, it's quite a fashionable thing to be like a startup founder. So always thought I'd play it safe, go into corporate, do marketing, knew I'd enjoy that. But it's when I was there, I actually loved it there, it was great, but my sort of best mate from uni who we met week one in halls, he always had a bit more of an entrepreneurial flair. He worked at Accenture, so a lot more dry than L'Oréal, and he always wanted to do something, and we always discussed, oh, we'd be quite a good pair to do something together with quite different skill sets. And we were actually in New York on holiday, drunk in a bar, which is a good place to start Design My Night, and came up with the idea, which it wasn't what it became, but the sort of fruit of the idea of Design My Night, and then did like a year working our corporate jobs and starting Design My Night. So we met every weekend, most nights as well, and started building up Design My Night while we were at our corporate jobs. And then after a year of doing that, we then left and went full-time.

And to do both those jobs at the same time, you need to have either a massive passion for what you're doing, or I think the other motivator for building a startup can also be just really annoyed that the solution you're trying to make doesn't exist. With Design My Night, which one do you think it was? Because Clearly you were very innovative in terms of offering a solution that didn't exist in the nightlife space.

I think we became innovative. Like, Design My Night, when we launched, actually wasn't, you know, Time Out existed, which still exists today. So when we launched Design My Night, it was just a discovery platform. It sounds crazy now, but we focused more like mobile first, digital. So we were really playing into the millennial audience. Now everyone wants the Gen Z audience. For us, it was the millennial audience who were mobile first, everyone had iPhones, so we were like, okay, well, if we can help people while they're on a night out to make a good decision on where to go, that's a good starting point. So it wasn't hugely innovative. We became innovative, we like made software when we were there. So we made booking software for bars and pubs, similar to OpenTable, but we sort of left them to restaurants. So that was our big innovation, was actually changing the whole booking culture in the bar scene in London to start with, where we went to bar managers and said, "Hey, you should be doing bookings like restaurants." And then we were saying to end customers, "Hey, you can book into a bar for the first time," because back in the day you didn't book into bars, you would just show up with, like, your backpack on, try and get a space, you'd sit by the bar. So we were like, this needs to change. So I think that was our innovation, was changing both sides of the industry. and we started in bars and then went to pubs.

Yeah, and I think obviously a big element of making that idea work would be actually like pitching this idea to the bars to buy into it and to consumers to go on it. And actually, funnily enough, like, the podcast you do now is all about pitching, people pitching to you, successful businessmen. And it makes me think, from what you were doing originally and the learnings you might have made and from your podcast, What is it exactly that you think makes a good pitch, and how can students maybe start to get better at pitching from a younger age?

Yeah, I think a big part is confidence. So, um, that's why for me a language degree was awesome. So a language degree gives you a lot of confidence because you've got to be ready to make a fool out of yourself. You know, you're going speaking different languages and invariably making mistakes, um, so you need to back yourself. Um, you know, I've never really enjoyed a pitch where I can see I want to see the person pitching to me. I want to help them if they don't look very confident, which isn't the best place to start on. You want to be front-forward, like, "I'm confident in what we're doing. I'm confident in the plan." Also learning sort of sales skills. Sales is always like the unsexy part. It's sort of like the estate agent of startups. But actually, sales is fundamental. Like, every good startup needs great salespeople. And I think that's one of the best skills you can have as a founder, is the art of selling. And there's plenty of books that you can learn about the art of selling. So I think that's super important as well. So yeah, it's those two things probably put you in front of anyone else when I'm sat in front of someone.

And has there ever been like a pitch where you thought like this was amazing? Or has there ever been a pitch as well that complete opposite? And like, do you think when you're pitching, for example, that one can bounce back if they already give like a bad impression?

Yeah, definitely. So I've seen plenty of great ones, plenty of terrible ones. For me, what people are pitching me is for investment into a startup. So the best ones I've seen come with a very clear plan of what the startup is. You know, what is the problem we're solving? There's a big phrase you use in the startup world of, is it a painkiller or is it a vitamin? And a vitamin startup is one that's a nice-to-have, and a painkiller is one that really solves a problem. So I think before you think about your business, think, is this a painkiller or a vitamin for the audience that I'm solving? So when I'm presented with the problem that they're solving, I'm immediately thinking, okay, is this a painkiller, is this a vitamin? If I don't know the market, I'm looking for them to tell me why it's a painkiller problem they're solving. And then you can just follow a very clear format of problem, this is the solution, this is how we're going to bring it to market, this is why I'm the best person to bring it to market, this is the team I've got, and this is where I think it can go. Like, if you can knock off all of those points. And the final thing that I love is being concise. When someone starts to waffle when you ask them a question, you sort of know they're covering their back a bit. So always give very concise, to-the-point answers.

If I talk about my experience as a recent student, a student who was looking to do entrepreneurship while at university, I went through some accelerators and not to say there's no value in them at all, there is of course, but there was a lot of focus that was put on load of ideating and ideating before you actually, and to the point that you don't even go ahead with an idea that could have been very good and I feel like With the GraduGuard, like, this has accidentally become my career and my business and everything that's come from it. I never started off as a business, I just went out and did it. And, you know, if we use your first company as an example, Design My Nights, did you, how long did you spend with your co-founder thinking, okay, is this gonna work, before you just went out and did it?

Yeah, it's a good point. So, I'll answer it in two. So, one, Design My Night was just, we were young, we had no idea, there wasn't all this, startup content that's out there, there is now. We just did it, like we literally just threw ourselves into it. We often say if we knew the toll it was going to take on us, we probably would have thought long and hard before doing it. It's ended up brilliantly for us, so we would have done it again, but I don't think there's anything that can prepare you mentally and physically for what a startup, if it's going to be successful, is going to take a toll on you. So I'm always glad I didn't know at that time how difficult it was going to be. Where I am now, ideation is mega important. You know, we've launched a few businesses since Design My Night, and we've probably had 15 good ideas that I would say, but we've only launched 2 because we go quite deep when we ideate. Back to that painkiller vitamin, I see a lot of people pitch me, they've already spent a year on it, and I'm just looking at this thinking, "Ah, this is just not a good idea, like it's just not gonna work." So my advice when you come up with an idea is I flip it on its head, and I tell people to try and do everything you can to dissuade yourself it's a good idea. What most people do is they come up with an idea, they get excited, which is great, but then they'll go out and try and prove that it's a good idea. And if you're trying to prove to yourself that it's a good idea, the way you frame questions when you're asking people in the industry will be very different to trying to prove that it's a bad idea. So for Trumpet, one of my new businesses, we spoke to 150 salespeople, and before we even lifted a line of code, and we were saying to them, "Why won't this work? What do you use already that means you don't need Trumpets?" All those questions versus, "Why is it great? Why do you think this will work?" And that gives you, like, a really good balance, and if you can get through that process, you'll then be like, "Okay, maybe this is a good idea." But I totally agree with you that sometimes you've just got to do it. So when we do a green tick on the ideation, we go and do it. We then don't falter because, yeah, you can get into this state of just paralysis.

It seems like a very uncertain and very complex part of starting a business. And you mentioned that you really enjoy— this is probably your most enjoyed moment that you— of starting a business, like the early stage. Why, why is that? Because personally, from my own experience, like I'm working on a startup as a university undergrad, and it's been very difficult. It's been very difficult.

Yeah.

So like, how do you find— it's interesting, I guess, for the audience to see how you find enjoyment in that.

Yeah, I mean, it's going to get harder. So if— I hope your startup's successful, and as it gets bigger, it will get harder. Um, I actually look at the early stages, there's less pressure. Um, I haven't really got a team that are relying on a salary that I'm paying them. Trumpet, we're VC-backed, which is a whole nother pressure. So actually, at the start, when you're ideating and coming up with ideas and launching it, it's, in my mind, it's still fun. I've got nothing to lose here, you know. I'm, in my core, I'm a marketing guy, so I love coming up with the brand and go-to-market strategies. So for me, it's still like a hobby at the start. And then the minute you start getting an inkling of it being a success and you're hiring people and you might need to raise money from angels, that's when the screw turns and you're like, oh, okay, this is, this is serious. But you're right, it will always be hard work, but I love, I thrive off hard work.

You did a languages degree and then obviously worked at L'Oréal, and it seems that everything you know about business you've sort of self-taught, is that fair to say? Or have you done any other courses? I'm not sure, but yeah, my question is to you, when you were at university, what are some things, like granted you do need to learn something on the job and you can't prepare for everything, but things that you wish you knew from a younger age?

Yeah, so I learned a lot at L'Oréal, so I'm not one of these startup guys that is like, you know, screw corporate, blah blah blah, like actually for me, you know, 3, 4 years there I learned how to run a P&L, how to manage a budget, how to forecast, how to report upwards like I do now to investors, how to manage a team. So you learn a lot if you go and work in a corporate, you know, and there's no problem going and working corporate for a few years, you know, we've all got time, touch wood, on our side, so you don't need to rush into anything. For me, I'm not one saying you need to do a business degree, and I know there's courses on entrepreneurship and all of that, which is great, and hopefully it will give you that motivation to be a founder, But the best skills you can learn to be a good founder is more like interpersonal skills. It's, you know, I've always said like I'm not a genius, like I'm not, you know, like Elon Musk or Jobs or any of those people. You don't need to be that type of genius to be a founder. You just need to get people to like you, whether that's your team, whether that's your customers. You need to be able to sell your ideas and yourself. So I'm selling myself as my founder to my team every day, and I'm selling myself to our investors, and I'm selling the product to our customers. I always say, just don't be a dick. Like, I meet a lot of founders that are, unfortunately, and like, nice people, I think, do land on top. Like, you need to be ruthless sometimes as a founder, unfortunately, but you don't need to do it in a horrible way. People will want to join you if you're a nice person. And communication skills. So it's all these sort of soft skills that you're not necessarily taught, which I think we should be teaching at school, which make you be a good founder. Because a founder, you need to do everything at the start. And, you know, unless you are a genius, you're not going to be exceptional at maths and selling and marketing and video editing. But you need to be able to do a bit of everything well, and then you hire a team to actually show you how you properly do it. Um, so yeah, it's the more interpersonal skills.

I think, um, potentially because you've done so much in your career and so much business-related investing and podcasts, it'd be easy to overlook the fact that you actually did land a very impressive first job at L'Oréal, you know. And one of the main missions with this podcast is to sort of humanize CV and, and make it seem that much more attainable than, than people build it up in their head to be. So You go from Nottingham to L'Oréal, talk me through how you did that.

So again, I don't know if this happens now, but there was graduate schemes. So there was, you know, probably like 10 FMCG companies that were always coming to campuses. L'Oréal was one, Procter Gamble, who make most of the home products that we have, Orange, who I don't think exist anymore, who were like EE, so a phone network. And basically they say like, come onto our grad scheme. So I applied for like 4 of them I fancied the L'Oréal one because L'Oréal is a beauty company, but essentially it's a marketing company. There's only so many ways you can make a new mascara. It's actually what you call it and how you market it is how, you know, their innovation. And you then, you, we went through a process. So there was, we went in, we had to do an online application, which again comes back to interpersonal skills, like knowing how to write, write concisely, sell yourself, which was the first application. I see people using ChatGPT for job applications to trump it, and I put it straight in the bin. Like, even if they are a great candidate and I can smell ChatGPT a mile off, so do not do that. And then, funnily enough, for L'Oréal, we had an assessment day. So you go into their office and they test you on reasoning and marketing, and we got to the end of the day, they pulled me in, they're like, we're in a bit of a dilemma with you, Nick, because you got the worst maths score we've ever had, but probably the best marketing. So they made us do like a marketing challenge for like half a day. It was like The Apprentice. And they were like, what do you think we should do? Is what they said to me on the spot. And I was just like, well, I don't— I'm really good at Excel, and you didn't test me on my Excel skills. You were doing A-level maths for some reason. Tell me where I'm going to need A-level maths in, in this marketing job, but let me show you how I can manage a budget in Excel. I was like, because I am terrible at maths and I'm not going to get better at that, but that's why I've taught myself Excel, so I don't need to be good up here in maths. And luckily they went along with that, so they did hire me in the end. But yeah, I could have not made it.

And would you still recommend graduate schemes in general? Um, obviously it got to— got you to where you are now, but I guess now with, um, hard skills now being a lot easier to obtain with AI and stuff, would you still recommend it?

I've always said it gave a really good grounding, like, to just, you know, I see a lot, and I'm, I'm one of the biggest champions of young founders, and that's what I'm for. Um, however, I do see the other side of people that come, like, maybe in uni and starting, or come straight out of uni and be a founder. Like, you've never really managed someone, you've never— I actually learnt management from two amazing managers I had at L'Oréal. So it was actually learning these skills by being in a corporate role, which I enjoyed at the same time, made me the manager that I was at 24, 25 when I started Design My Night. If I would have gone straight from Nottingham to Design My Night, I think I would have been just a fish out of water. So I'm in favor of it. I'm also, you know, it doesn't have to be the corporate world. So now if you're really interested in startups, what I say to a lot of founders is, okay, you don't have to have the idea yet, go and work in a scale-up. You know, there's now the world of scale-ups that have raised a Series A, Series B, you know, they're like corporates nowadays. So if you want to learn the startup world, go and learn the ropes in a scale-up and see how the chaos of a startup works, but a bit more a bit more advanced. Go and learn the ropes there, then maybe when you learn that, maybe go to an earlier stage startup and see real chaos at work and see what you can add to that, and then maybe go and start your own thing.

Interesting. And Trumpet, so you mentioned about killing the sales deck, what does that actually mean?

So, Trumpet was an idea born out of Design My Night. So, Andrew, my co-founder, and I, when we were ideating, we looked back at Design My Night, we had 100 people when we sold, And we looked at the sales team and we were like, the sales team is the only team in this company that doesn't have technology. The engineering team had a new tool like every week they wanted to buy. Marketing had like Canva was just coming out then and other marketing tools. And if you think about sales, and it still is to this day, you've got, without boring you about sales, you've got CRM on one, so Salesforce, HubSpot, where you're tracking all your deals. You've then got like LinkedIn Navigator and outreach tools to like get in front of the prospect. Once you get in front of the prospect, it goes back to email, and you're, you know, 60 days is the average sales cycle. You're going back over email, you're sending each other decks. PDFs were invented in the '70s, so we were like, this, this has to be more modern with, you know, with like Notion and Google Workspace and all of those. We were like, we need to bring that element to sales. So we created the concept of Trumpet, which was sort of digital sales rooms, where once you like have a demo call with someone, you follow up with this digital space, which is all branded to the prospect, which a salesperson can make in like 10 seconds, like Canva. And then within that digital space, you can put in your sales deck, you can put a video note, you can put in case studies, you can put in pricing proposals, but it all lives in this digital link between you and the buyer. So rather than just sending loads of emails back and forward, you just keep adding to this space until you get the deal done. And the other part of that that's really interesting to people is the data. So obviously when you're emailing back and forward, you've got no idea about what's actually happening on your customer's end. But in the digital space, you can see when they've logged in, what are they looking at, have they passed it to anyone else in their team. So we call that buyer engagement data. So like, how engaged is the buyer? So that's a big, a big thing for us, is that the data play. So yeah, we're trying to sort of move sales into the modern age.

And you mentioned you could, uh, you could tell if someone's applied to a role at Trumpet with ChatGPT, and I think basically what you were alluding to there is that you need authenticity of voice. Yeah, it's a very important thing for the people you look to onboard in your team. How does that actually work in practice then? So you're obviously involved in who you recruit into the team. What's a good candidate to you?

So we always ask for like a covering note, so we use I actually don't care about a CV. I actually very rarely will look at the CV now. For me, the roles we're hiring, unless they are like engineering, and ideally you've done like computer sciences, but actually at Design My Night, some of the best devs we had were home, home-taught coders. You know, the roles we're hiring in startups are like account management, customer success, design is a bit different, again you need that specialist skill, but Those two roles, which are huge in startups, it's just about personal relations. Like, can you get on with someone? Can you get on with the team, and can you get on with the customer? So in an application, I'm just looking for that element of personalization to see, like, who you really are. I don't want an essay, but it's literally like, A, I've gone to look at what the hell Trumpet is, which some people don't. They don't even mention Trumpet. And two, like, just tell me in like 3 or 4 lines why you genuinely think you would be really good for this role, and tell me in 3 or 4 lines why you really want to work for Trumpet. Like, just show me that you've looked at the team, you've looked at our website. And I know it's difficult because people are applying for hundreds of roles, but I don't really care about that. I want to look for people that really want to work for Trumpet. And, you know, using ChatGPT, you can just see it scraped it off our site. It's like, "I'm excited to work for Trumpet because it's a digital sales room, and then, then, then." I was like, "Okay, well, that's like our H1 header on the website. That's why you're saying that." So, just a bit of personalization. Show that you're, like, a human being. Tell me why you really want this role, where you want to get to. Like, it's all the standard stuff, but write that in a concise way and check that there's no spelling mistakes. Like, double-check your stuff. Put it into spell check. Like, there's enough stuff now to show there's no spelling mistakes, um, and just show that you really want this job.

So you're currently building your team with Trumpet, but with Design Art, you, you built that whole team yourself, you delegated, it was your baby. And in 2019, you know, people come in to acquire you. What, what's going through your head when that happens? Because, you know, not that I'm near that happening for me, but there are like, you know, partnerships, and you know, with partnerships comes giving away part of maybe a business you do, or like complete creative freedom. What were the considerations you had to have then, and what ultimately made it feel right to do it?

Yeah, I think, so we actually sold it in 2017, and then we had a, it's called an earn-out, so we had a 2-year earn-out where you have targets with your acquirer, to hit, and then once you hit those targets, you get more cash basically, and it also allows you to hand over the business in that time. When we came to exit, we, to be honest, we were ready, like we were emotionally ready. It'd been like 7 years, we'd put everything into it, and we, our fault at Design by Night, where we were quite sort of too involved in everything, like micromanaging. So we were across every part of Design My Night, and the thing about running a booking software is it has to be live 24/7. So if our booking software went down at 9 o'clock on a Saturday night, we were screwed. So we had alerts on all of our phones, so, you know, I was out for dinner and if my phone was vibrating in my pocket, my first thing was just like, oh shit, the software's gone down, but it was just like my mum calling me. So like, I was like living on the edge every time my phone was vibrating. So we were too, you know, I should have had, you should have an on-call team that can do stuff like that, so we were probably way too involved in everything. So when it came to exit, to be frank, financially it was the right thing. Andrew and I had, didn't want to run Design My Night forever, we knew that. We were very clear with each other how much money we wanted to make from this, and that was a big driving factor to start a startup. I don't think that's talked about enough. So we got to enough revenue to sell it for a big enough value that we would be happy with the return. And then, yeah, it's more of that and protecting the team. So we just wanted to make sure the team were okay when we did the handover. But because we were there for 2 years, you know, it gave us enough time to sort of fall out of love with running it and then sort of handing it over And then, to be honest, the way my mind— I'm thinking about the next thing anyway. So probably like the last 6 months, I checked out and I was already thinking about what the next thing is.

I've interviewed over 50 founders, and all of them have a slightly different take on the kind of person that should be a founder, like based off their own experience. And I'm always interested, like some people will be like, you know, it's really not for everyone, I wouldn't recommend it, I'm not, you know, I'm just I'm a weirdo, like, you're not like me. And others will just be like, you know, completely normal people who are just like trying to make, build something and make something. Like, and there's obviously a spectrum there, right? Like, as you said, like, not all founders— not to call out any of my previous guests— but like, they're not all, you know, the nicest people or the easiest people to work with. Where do you fall on the spectrum, or at least in terms of your thoughts on entrepreneurship? Like, what is it that you really love about it? Like, why would you sell it to a student?

Yeah, I think, well, firstly, when you talk about being a founder, I think you need to realize that there's different levels. So you can start a startup that you might never hire someone and take, and it's your own baby, and you take a brilliant salary from it every year. That's a startup. Or you are a startup that doesn't need to exit, but you might have a team of 10, and again, you are taking a great salary from it every year. It's getting bigger and bigger and bigger. You might exit one day, but that's not on the plan. You then got the Design My Night level, which we never took venture capital money, but we'd always planned to build it and sell it. And then you've got the ones that are counting to take venture capital money, and I want to build a unicorn essentially and take it global and big. So you've got this whole spectrum of different startups that you can do, um, which are probably suited to different people, I would say. I would say most people can do it. I say I don't think you need to be a weirdo. I don't think you need to be a genius. I think you need to be ready for hard work. It sounds obvious, but I think you need to just be ready to put everything into it. Like, no startup will be successful unless the founder, you know, I don't care, there's this whole move away from like hustle culture and all of that, but if you don't work really, really, really hard, harder than you have on anything, it won't be successful. Successful, and that's just a fact, at least for like the first 3 years to get it going. So I think you need to have grit, you need to have determination, you need to be a problem solver, you need to not be someone that gets in your head too much. I think one of the best advice I look for when I give to a founder is being able to stay on an even keel. So like when you do something great, don't get too high. And equally when something goes wrong, which it will regularly, don't go too low. So if you can keep your emotions quite level, that will put you in a good emotional state. Because I see a lot of founders just break down because they just can't cope with the level of pressure. So I think you need to really ask yourself, like, I don't like using this term, but am I mentally strong enough, mentally willed enough to pull through? I think most people, if you have that, can be a founder.

A lot of people say that the best investors are the people who invest in the person or the people behind the company. And I wonder, your experience as an investor, how has that maybe shaped how you look at yourself as an entrepreneur? Like, if you're, you know, if you're vouching for teams and maybe instead of the person and like, Yeah, and also, to what extent do you agree with that statement?

I don't think they can live independently. So I haven't backed a great founder because I thought the idea was crap. But equally, I haven't backed a startup that I thought was great when I didn't think the founder was up to it. And I've seen both fail. So I have backed great founders— that I thought were great founders that had a great idea, but they weren't great founders. And didn't have everything that I just mentioned, and invariably the company failed. So I think you need both. You need to have that killer idea that, as I say, you're really solving a problem, and also you need to be the right type of founder. I've learned a lot as a founder, so, you know, some of the founders I've invested in are exceptional, and I see how they run their business, and I've taken some of those skills from them and implemented it into myself. I'm learning, I'm relatively young, so I'm learning still as well. Um, but yeah, they can't live independently. They're like, you, as an investor, I have to see the idea is amazing and that the founder is amazing.

Do you think you're going to get the founder bug again?

I don't think it goes. Uh, I think that's why we did like Trumpet, and we've got other ones as well. Um, I don't have to work now, I'm in a very fortunate position, but I just ask myself, like, what do I enjoy? I love starting businesses, I love getting them from zero to one. We've done a slightly different model because of that, so we have a third co-founder in Trumpet, and he's the CEO, so he's sort of the face of the business, whereas Andrew and I can focus on the stuff we enjoy. We've got the founder bug, but we're doing it in a slightly different way where we're not like neck-deep into it. We've got the third founder to sort of take some of that weight off us.

And when you started your career in marketing, you obviously learned how to present a brand and make it very compelling and make people want to buy into the brand. And then obviously, I'm not sure exactly when the LinkedIn boom happened, but at some point in time personal branding became a term, and you have a very big personal brand yourself, and, you know, a large LinkedIn following, and you post pretty regularly. When was it that you realized the power of personal branding and how you could harness that in a business sense?

Yeah, when it launched, I, I would guess, like, it feels like 5 years ago it started to become a thing. Um, interestingly, I didn't have any other social media in my life, so I don't use TikTok, Instagram, Facebook, Snapchat. I don't have any of that from a personal point of view. Um, so LinkedIn is, is like the only one I use, but I'm not sharing personal stuff on there, so it's definitely for business. Um, I made a conscious effort when we sold DMN, knowing that I would still have the founder bug, that eventually I would create more businesses and I would need them to be sold to people. So I made the conscious effort to start building my personal brands, get followers in this space, and then I knew that when I was ready to launch businesses, I would have a ready customer base. And actually, when we launched Trumpet, we did a waitlist, and we only did that waitlist on LinkedIn, and we had like 3,000, 4,000 people on the waitlist, and probably like 75% of those came from LinkedIn. And a lot of our customers today look at the content we put out on LinkedIn, then look at Trumpet, then sign up. So for me, it's become a bit of a must, and it doesn't cost anything. So the whole personal branding thing is what you've said a few times, is authenticity. Like, be authentic, only talk about stuff you know about. I see people who are talking about exiting startups that haven't exited startups. So, you know, you'll always have a tribe that want to hear what your point of view— so from yours, it's student who's now a startup founder, that take us through that journey. Mine was how I built and exited a business and now starting a new business. This is the journey that I'm going to take you on if you follow me. Um, and try and educate. I always try and think, okay, what have I learned that I can put out in my content that people can at least take one thing from that post? Um, so it's not just all like pictures of yourself saying, I'm great and my, my new startup is great. Like, try and help your audience. As well.

So clearly, um, Design My Night and, um, Trumpet are very different businesses. Um, would you say in terms of the founder bug that you're very open in terms of the problem you'd be solving, or is there a thought process behind that?

Yeah, that's an interesting one. I, I think I know what my skill set is, which became— Design My Night was a big consumer site, but actually our business was the software, is why we were acquired. So I know how to build SaaS products and scale SaaS products, and actually, if you've got a problem and you solve it, the playbook of growing a SaaS company is the same, like, whether it's Slack or Notion or Trumpet, pretty much the same playbook. So once you've learned that playbook, which we did at Design My Night, with not much money either, I know in my head that if I find another SaaS solution with a big enough problem that we're solving, I can apply that same playbook. If I had a great idea for a, I don't know, a nutrition drink or something, would I do it? Probably not, because yeah, like my whole like PPC side, paid adverts, all of that is probably not my strongest suit because it's something I've sort of been out for a while. And TikTok and all of that is something that I've sort of been out of the frame a bit now, so I probably wouldn't launch something like that.

Selfishly, I want to ask you a question, as you're also a fellow podcast host. Uh, it may not be for the audience, but, but I feel like that there is a lot of value that can be derived from this question, in that for a successful podcast to do well, especially given that it's very manic-depressive thing, like especially people that put everything into it, like you need to love the conversation, the concept, you need to you know, not really care about the views and the money you're getting from it. And obviously, maybe the money wasn't a problem when you started it, the connections weren't hard to get, and, you know, you did do quite a lot of episodes. Maybe you didn't, you know, do the whole video and proper shebang, but there was obviously a passion, a love and drive for the concept, you know. How did you come up with the concept? And maybe for listeners, what is it?

So it's called Pitch Deck. So it started out So I love Dragon's Den. I always— I loved, I should say, Dragon's Den and Shark Tank, which is the American equivalent, which is like Dragon's Den on steroids. But I was watching those shows as entertainment, knowing that other people were watching them as fact. And, you know, going into Dragon's Den is not fact. You know, you're not asking for £20,000 for 50% of your business. Like, that's not the real world. It just sort of bugged me, and I'd built up a following of founders and startups, and I just didn't want people to think that is how you raise money. It's not. Like, it's an entertainment show. So the concept was I bring in an angel investor alongside me for every episode, and we then got a startup founder to pitch their business in like 2 minutes. And then we sort of lifted the lid on what angel investors ask founders. So the founders, fair play to them, they came, it was a live roasting, like they weren't prepped or anything. And we asked them questions like I would in a 30-minute meeting if they were presenting their startup to me in the real world. And then the last 5 minutes of the episodes are without the founder there, that myself and the angel investor discuss the opportunity, and very honestly as well. We're not looking to like tear anyone down. So for people listening, it shows like how to pitch, what some good pitches are, what some bad pitches are, how an angel investor will analyze that business and what questions they might ask you, and then how an angel investor might think when you're not in the room. So yeah, I just wanted to bring a bit of reality to the startup world. It's good fun to do as well.

And because podcasting wasn't necessarily something you needed to do within the trajectory of your career, It seems to me that there's an element of you that likes putting yourself in uncomfortable positions in order to maybe grow, um, and that all comes under this phrase of imposter syndrome. So at some point you may have had it a lot more than you have it now, but, um, and you're watching people invest, uh, pitch you, and you're deciding who you invest in. But from the perspective of looking at other people pitching to you and your own experience How do you think you can harness imposter syndrome to actually be like your superpower in terms of business or pitching?

Imposter syndrome is actually a phrase that I hate. Okay. And I hear it all the time. And look, far be it for me to tell someone they don't have something, that's not what I'm trying to do here, but just the whole notion of telling yourself that I don't fit in here or I'm not good enough is just such BS in my mind. Like, Who are you comparing yourself to that you think you're not good enough? Are you looking at TechCrunch and seeing these founders raise hundreds of millions of dollars? Okay, well great, but you don't have to raise hundreds of millions of dollars to be a good founder and have a successful exit. Are you looking at Elon Musk and Steve Jobs? Okay, well, one in 10 billion are those type of people. So this whole notion of imposter syndrome for me has become a phrase that just allows people to get in their head and tell them they're not good enough. And if other people are telling you you're not good enough, you cut them out of your life because they're no good for you either. So for me, it just shouldn't exist. If you do have this notion of imposter syndrome where you think you're not good enough, I think the only way you can get over it is just by getting out there. Putting yourself in uncomfortable positions, again, which is why languages was great. And that is ultimate imposter syndrome, because you're like, well, I actually don't speak this language, but I'm coming into your country trying to speak your language. So I think you just need to put yourselves in these uncomfortable positions. You have to put your ego at the door. I think ego is a big thing at the moment. So everything I try and do is ego-less. I'm very aware if my ego is taking over. I always tell founders, before you make a decision or before you're doing something, if it's led by ego, don't do it. Like, what is the real reason you want to do something? So yeah, put yourself out there. I can't just tell you you're great. And you know what, you might not be the right person to be a founder. Maybe you could be a COO in a startup, or, you know, not Just because you might not be a good founder or the right person to be a founder doesn't mean you don't have other great skills. So yeah, if you're telling yourself you're not good enough, think about what— why, like, what am I telling myself I'm not good enough at, and what am I benchmarking myself against to tell myself I'm not good enough? And just, just do it. Most people are actually really nice, and they won't try and tear you down either.

Yeah, on that, I think we've spoken a lot about, um, building the team from the ground up, but obviously one of the most important things is the people at the top who are managing. And you've had a few co-founders in your time, and I wonder how you go about the process of, you know, selecting or deciding who's right for you. Is it a case of them complementing you, or do they need to just understand the mission statement? They need to have the same work ethic? Like, what are all the things that you consider?

Yeah, it's a hugely important decision. So I see people get into co— they get a co-founder, they make the decision like that, like they've met them once or twice and yeah, he or she's cool, like we can be co-founders. Like, it's a relationship and you're probably with your co-founder more than you are your partner actually. So you need to be on exactly the same level. So what do you want to achieve? A work ethic is huge. If ever you think one of you is working harder than the other, that's going to start causing resentment. So you need to both be on the same work ethic. You both need to probably have the same style, the approach, the niceness that I talked about. I don't think I could work with a co-founder that wasn't that. I think that would really rub me up the wrong way. But then for me, it should really be about complementing. Like, Andrew and I work great together because he's a lot more analytical. He's more operations, more data-driven, and I'm more marketing and sales. So actually, when we come together, we're like the fully rounded person. So that's super important. And then the other side is trust. Why we've worked so well is we implicitly trust each other. From like a small thing to do with like money, you know, you're having a joint bank account, and if you suddenly think someone's spending more than you, why, what are they spending that on, like even that type of thing, like you would trust a partner, but then also trust their skills. You have to respect and trust their skill. So what we did at Design My Night was Andrew did ABC, I did XYZ, we didn't ask each other's opinion, but we would come together as co-founders and be like, oh, I've been working on this, this, and this, this is working well, this hasn't been working so well, what do you think? So we're not like micromanaging each other, you just gotta trust each other to get on. So when you pick a co-founder, like, really need to get under the skin of all of that, really get to know them properly. And because that's the biggest reason why startups fail, is co-founders fall out.

Is there like a trend in how co-founders meet? Would you say the most successful businesses were co-founders who are friends initially, or do you think it's irrelevant?

I don't know, I haven't seen any stats on that. The ones that I've worked with, and speaking from personal experience, I've always known them a long time, so we had a friendship before we went into business together. Like Andrew and I knew each other for like 8 years before we went into business together. So I don't think there's any formula that you have to have been friends before, but if you are in an accelerator or a program where you meet another co-founder, don't just jump into it. Like, spend months working together on it before formalizing it, you know. So you can do that as well, but it's almost like, let's road test this relationship before we like sign the papers and set up the company and become co-directors and we give each other shares. Like, maybe let's just work together for a few months and see how we work together, because yeah, it's a real risk if you don't.

To summarize, I guess for students, what would you say, 4 or 5 key steps would you say in terms of how to actually build a startup? So like, when, for example, you think is the right stage to start building a team or start invest— trying to get investors down, like, what would you say are those steps to summarize?

So you need to put the business out there first and see if there is a potential business. And again, that doesn't have to cost you anything. So what we do when we— before we actually commit to like building a product is we'll drop a one-pager of the problem, the solution, and what we think it's going to be, and just put it out there. So if this were a product, this one-pager I'm giving you, what do you think? Would you buy it? What's good? What's not good? The stuff I talked about, like trying to prove it's a bad idea, like that should always be step one before you think of a brand name, before you think of a logo and all of that.

Would you call that validation?

Validation, yeah. Ideation to validation. Then most businesses nowadays with technology, you shouldn't require money to get early customers or get nibbles or get interest. I love it if a startup come to me and say, "We've already got," it might only be like 15 customers, "but we've got 15 customers who are paying for the product." That just shows that there's some validation of your idea as well. 'Cause there's one thing validating it and there's another thing getting people to pay for it. Then you need to start forecasting, is just what people forget to do, like, and someone who's terrible at maths, I actually love our forecast sheet. So we have a forecast sheet that we have basically forecasted the business for 5 years. At the start of it, we have lots of variables that you change, you know, because you didn't know, I'm not going to forecast correctly, and you just start to build out the business on paper, mathematically, And you're like, okay, well, to get to this revenue, it looks like we're going to need these 2 devs, these 3 customer support, da da da da da. So actually, to get to that phase 1, we might have to raise, looking at, okay, we're going to need $200 grand. So then, raise $200 grand and go and speak to angels. A, you don't always have to raise money. I think we're taught this now, that to be a successful startup, you have to raise money. Generate revenue, invest that back into the business, grow, invest that back into the business, grow, and own 100% or 50% each. Don't forget, if you then sell it for 10 mil and you get 5 mil each versus selling it for 30 mil but you've only got 10%, you actually make more money selling it for 10 mil. So, I think people just think you have to raise. So, it depends what business you want to grow. I think we talked about way back, you know, do you just want a lifestyle business, take a good salary, do you want to grow it to exit? And probably the next step is not having to raise, like, tons of money from the start. I think, again, a lot of people come to me and go, "I'm raising a million." And I'm like, "Okay, why are you raising a million? Like, why don't we raise 250 grand now at a lower valuation, so you're not giving up much equity? Let's get the business going, let's get some customers, let's build a little team, then let's go and raise another 250 grand, and you'll probably close that round quicker as well." So I always suggest doing like smaller rounds, lower valuation, you'll get the round done quicker, and then you decide where you want to take it from there.

My final question to you is, what is your definition of success and how has it changed from when you first started your career at L'Oréal?

Yeah, success is a tricky one, so I sort of look at success as like an escalator going up a mountain. So I think a lot of people will look at the peak of a mountain and be like, once I hit that, I've been successful. But for me, success is also like wrapped up in like happiness and purpose. And I think if you look at the top of the mountain and be that success, it would have been for me exiting a business and being financially comfortable. But okay, well, once you do that, I hope I've got 60 years left to live, so what comes next? So I always see it as like a moving target. So like, that's now my success, but then I'm looking at my next success as, okay, well, I want 5 startups that, you know, I've got 5 co-founders on that are all successful, and 3 might have exited. Or I want to learn about setting up a media company, which is why I've started this podcast. So for me, success is just about winning every task I set myself. So whether it's a podcast, whether it's a business, that's always trying to move. And I think you should do that in your personal life as well. So like, I'm teaching myself Japanese now, because I just love languages. So I know that would be a challenge. There's no success. I'm never going to be fluent in Japanese, but I'm just constantly challenging myself. So again, I think if you put that marker in what is success, I don't think you'll ever be happy because you either won't achieve it or you will achieve it, and then what do you do next? So I think always just try and keep, keep that moving, like more look at what is my purpose, what brings me happiness, and then you'll find success, I think.

Nick, thank you so much, you've been great. And, uh, Jake, thanks so much for co-hosting your first episode with me.

Thank you. Thanks for having me.

Thank you for interviewing me on your first one.

Cheers, mate. I loved it.