Nick Telson-Sillett: Angel Investing, Being Creative and Getting Wiser

0:00I unashamedly want to win in everything I do. Nick Telson-Sillett. He isn't just a famous host of Pitch Deck, a go-to podcast for angel investing insights. He's a real deal entrepreneur who, after selling his own company five years ago, decided to give back. Through Horseplay Ventures, he supports up-and-coming startups. And with his new software company, Trumpet, he's still in the game. Eloquent and open-hearted, Nick's here to share with us his personal wisdom and the lessons he's picked up from his numerous podcast guests. Us three have like an hour intense meeting about some form of strategy without them thinking, oh, someone on our advisory board took this product to America and scaled it to 100 million.

0:42Let's get them on the phone now. Imposter syndrome is a funny one. I don't really buy into it. The dopamine hit of buying stuff is a hit that goes. We're all just humans muddling through life. Time is the greatest gift that anyone can give you.

1:04Nick, thank you so much for joining me today. I'm really happy to see you. You sold your business seven years ago. So you had a chance to process the whole experience. And I know you've done a lot since then. I'm really looking forward to discuss that. But did money make you happy? Money, yes. Money's made me happy because it's afforded me time to do things that bring me joy. What's next for you? In the immediate, what's next for me is succeeding with Trumpet and winning in that, whatever winning looks like to my competitive nature. And then I haven't thought that far ahead, but I will reflect after Trumpet and think what's next for me.

1:44Is angel investing a good investment decision? Yes, if you surround yourself with more experienced investors than you, start small, learn the ropes, and then it can exceed most safe financial investments. What are the most important lessons you learned since your exit? Time is the greatest gift that anyone can give you. Anything else? find your joy in the smallest things and you'll realize that climbing your Everest whatever that is isn't the thing that will will give you joy you know really try and find joy in the smallest things in life and you'll be a lot more fulfilled because you might not reach the peak for starters and you'll and if that was what you were banking your joy on you'll be disappointed and at the same time, when you do reach that peak, you'll realize that what's next.

2:49So if you can find joy in the little moments throughout the day, you'll be a much happier person. How do you want to be remembered? As a nice guy. I hate the word nice, but a nice guy that really helped the UK startup ecosystem. Fantastic. Can I take you back to that moment when you sold the company, you got your financial a reward and also you were free so you got your time and your money how did it feel yeah it was it was twofold for me because um I sold in 2017 but then I had a two-year earn out so um you know pretty much the day we signed was a Friday we had the weekend and then we were back in the office on Monday um as if nothing had happened which I actually I think helped the transition um you You could sort of come to terms with the new life you were going to have, but it wasn't like a sudden cutoff.

3:45So actually those two years, we could start thinking about ideas and what did we want to do next. But interestingly, 2019, when we fully, fully exited, I do remember sort of waking up that first morning on a Monday and just thinking to myself, I have nothing to do. Like, what am I going to do now? um you know design my night it was 10 years in total you know I was early mid-20s when I started it and it was you know my whole identity was was design my night and that's what my family would speak to me about that's what my friends would speak to me about as a founder I was obsessed with it so I was working non-stop um so yeah I had I had you know actually a real couple of weeks and I'm very like positive character quite a strong mental character as well but I really felt very flat for two weeks when I was like okay my whole purpose has gone yeah what's my new purpose um so I really had to sort of dig deep to try and find what that was and for some people it takes years of course um and I just sort of and I'm you know I'm still you're always still looking for it I think but yeah it was a couple of weeks of feeling really really low and flat while I was trying to figure out what would be next well two weeks I've never heard such a short period of time And before usually it's like five years.

5:11Okay. So after those two weeks, what happened? I would really love you to describe how your relationships with ideas like purpose evolved over time from what they were before you exited. Yeah. You know, the funny thing, when I think of purpose, I took out sort of loved ones and family because that's always there for me. So that's, you know, always part of my purpose. but I always say to my loved ones is you know you're 50 % of my everything and my other 50 % was startups and I need both in my life to be fulfilled yeah like um you know if I had one but not the other I wouldn't feel fulfilled um so I really looked deep and I just thought what did I really love about a my first job which was at L 'Oreal I did marketing at L 'Oreal for four or five years what did I really love there what got me out of bed there um you know apart from the the politics and the corporate side of things and then what did I really enjoy about Design My Night um and it's the zero to one um you know I've constantly constantly coming up with ideas um Some awful, some good, some very good.

6:28But my mind is constantly going wherever I am. And I just thought, oh, if I can find a way to ideate without the pressure, because obviously you've got no financial pressure at that time, which is one of the biggest pressures people have. So to take the financial load off my shoulders and actually just be creative and take the time to ideate and take the time to create a brand, take the time to build that MVP. And then what we decided, so that actually became our next startup, which is Trumpet, was to bring in a third founder. So myself and Andrew, who had designed my night, and then we brought in a third founder to be CEO.

7:17Because we thought, well, what didn't we love? and we don't want to do things we don't love and that was you know managing a big team and the office and you know all of that stuff but my my passion is brand and marketing and go to market so I was like look let's bring in a CEO I can be CMO if that's what you want to call me and just do things I'm passionate about and so that's the sort of road we went down and I know we'll talk about it probably but then you know we looked at angel investing as well yeah um I started a podcast and the one mantra that I landed on which I still hold dear today is I enjoy being busy but I don't enjoy being stressed yeah and when you're in the trenches of design my night I was busy and stressed constantly so I said to myself how can I make myself busy but not stressed um And that's constantly the sort of tightrope I'm walking now.

8:17And if I ever start to feel stressed for whatever reason, I'll reflect and think, okay, what's making me stressed and how can I change that? And I think that's the luxury I wanted to afford myself from my exit was time, of course, but not having to feel stressed to earn a living. So what motivates you to keep going, to have a podcast and a new business? I know you also do quite a lot of advisory work. Why are you still doing it? Well, A, I do love creativity. I love speaking to creative people. I love learning from creative people. So I think if you've got an open mind to constantly improve yourself, you know, mine was one exit, great.

9:05But, you know, someone like yourself has had like three plus exits, you know. So there's always people I can learn from. You know, I'm not, okay, I've exited, I'm done now. And I've got that hunger to learn, to improve myself professionally, not just personally. So that always drives me. Being involved in startups, creativity, ideation, brand, go to market, I love. And I have a mentality to win. I unashamedly want to win in everything I do. And that's what drives me. You know, yes, Design My Night, a big part of that was financial. um but i achieved that so now it's my inner drive that i want to succeed i'm very competitive and when i start something or do something i don't want to do it i half-assed i want to do properly and i want to succeed at it and and succeeding is very different for different people so i know what my mind of of succeeding is um but yeah i i want to win so like trumpet it you know we've got an idea of what we want that to become and for me now it's like I want I want to win I want that number two um and it's for my own it's not for my ego it's just for my own personal achievement yeah because you you now know that you are naturally competitive you've embraced that that personality trait of yours and you decided why not I will continue being competitive yes in everything I do okay sounds good to me so you mentioned that the motivation for Design My Night for your first business was primarily financial.

10:40So was it financial freedom? Was it just pure greed? How would you define that reason for starting your first business back then? Yeah, I think A, it's interesting because especially in the UK at least, money is seen as like a dirty conversation. You know, it's very different to say America where money and success is celebrated. I really feel in the UK that if you're successful or want to earn money, people will try and knock you down. It's a very different environment in the UK. But again, yeah, I'm unashamed that, you know, I wanted, if I was going to work that hard, yes, obviously the joy of starting your own company and not working for a corporate and challenging myself on that.

11:24But myself and my co-founder were very aligned that we want financial freedom. We actually sat down and did an exercise together on what financial freedom looks like. Okay. Because at the time he had one child, he's now got three lovely boys. I don't have children. So, you know, that's a very different financial burden on him than me. You know, I'm not materialistic as such. So people will see if I'm on podcast, I'm normally wearing just like normal clothes. I didn't need a fast car. So what we did was actually, and I recommend everyone doing this, is we drew up a list of everything we spend money on.

12:09Everything from rent or buying a property down to Spotify, Netflix, you know, haircuts, etc. And actually just seeing what your expenditure is, which I don't think most people do. We just spend. A, that was interesting. And then secondly, what in an ideal world without thinking, you know, crazy, crazy, crazy, what do we want our life to look like? so for example my holidays before costs x and then what i would love is that i can fly business or first and always stay in a five-star hotel in in one of the nicest rooms okay so what is the difference in price there and there so okay my new spreadsheet my holidays are going to go up x percent and this is what they're going to cost car i don't want a new car so that can stay the same food shopping will stay the same um so it helps you figure out what your priorities are yeah uh and if someone loves a fast car that's great like i'm not saying that's like some of our friends in common yeah like that's great like i'm not saying that's a bad thing if that brings you joy great okay but then on your spreadsheet that ferrari or whatever is going to cost you x and then we just summed up how much our sort of new life being realistic so not you know i don't want to get a helicopter everywhere I go for example so being realistic um and then when we summed that up you sort of saw what you had to get to you know okay well what is your monthly outgoing is gonna become and um we weren't miles off each other obviously said it was his more his children that made the difference um so we were like okay look if we can get from design my night to x amount of money when we sell that will afford us this life okay and then we can decide where we want to go after that So what that does is it puts it in context for you that actually we might, you know, we might sell for, might be happy to sell for 50 million instead of reading TechCrunch and thinking you have to sell for 300 billion.

14:13So it just sort of really focused our minds on how big Design My Night had to get for us to achieve our ultimate goal. And I think a lot of founders forget that. You just carry on the hamster wheel without thinking, what actually do you want out of this? So going back, it sounds like you're happy you did that exercise. You do not necessarily feel that you put an artificial ceiling on your ambitions. You don't have that feeling. No, it's a really good question. Maybe, maybe. So maybe we settled for still a great exit. But, you know, so for example, Design My Night, we never took global. So we, which was very strategic at the time.

15:00We thought, okay, let's dominate the UK. And we ended up in like 20 cities in the UK. You know, every city in the UK used Design My Night. And then maybe an acquirer will come and want to take us to America, for example. what we were worried about was let's if we go to america and it doesn't take off then wouldn't acquire a look at that and think oh well the upside being america isn't there so we were strategic but also we were thinking okay well to hit this number that we need to achieve we don't need to go to america we can hit that number in the uk in terms of revenue and ebit So, yeah, maybe there is an element of us capping our sort of expectations.

15:41But at the same time, when we did sell, it felt right. Emotionally, the market felt right. You know, we were sort of the new upstart and, you know, the cool new design. My night was also a lot of software that we sold to restaurants that most people don't see when they obviously use the site. You know, we were the cool new software, look great. we were you know much easier and better to use than like open table and all of those but then you know after five six years all these competitors were seeing what we were doing and sort of adding features that we had of course and then we started to think oh okay they're sort of catching up with us now and they've got billions behind them maybe it's maybe it is the right time just to get out so so there was strategic thinking but but it's an interesting question that yeah maybe we we so you kept ourselves a bit you managed to control your natural competitiveness at that point and decide you know what it's time to quit this game and start a new one yeah and and I I told myself that I'd succeeded so you know we we hit what we needed to achieve to which was the the goal of design my night so my competitive nature was like okay you've won that round that's what you wanted to achieve that's great and then to be honest by the end of it I was exhausted like it was my first startup as I said we started in mid-20s sacrificed my 20s really to do design my night because it was just all encompassing so yeah I think we were both just emotionally drained by it as well and I don't think we had the fight to go to America or carry on again have you ever regretted selling no definitely not um and you know when we fully exited in december 2019 then covid hit three months later and i cannot tell you how thankful i was for not having to run design my night a going out business uh during covid you know we had a team of 100 um and just dealing with what's the what the government um put in for for employees.

17:45Oh, okay. Yeah. Dealing with furlough and who's going to stay working, who's not, what do we do at the office? You know, I was genuinely so thankful every day that I didn't have to deal with that. So it was relief more than anything. So you were so rational about planning the financial side of your business, knowing when you want you to exit. How is this different if it is from how you're thinking about trumpet now um so yeah trumpet similar plans in our minds just on a bigger scale and so rory our third founder is very on board with how we think you know you know we're very tight three um and yeah i think we you know internally which you know we won't talk about externally we've got our own goals that we want to achieve with trumpet it um so very similar um but probably just on a bigger scale you know it's it's a much it's a pure play sass business it's instantly global um it's for sales teams every company has a sales team so you know the time is is huge um so similar thoughts um we brought rory on our thinking but it's it's on a bigger scale so you would say the financial considerations are still the primary once or your motivation changed a i think we had to be mindful of rory so this was his first business um so he probably has the thoughts that we had at design my night yeah he's thinking financially free so we have to be very respectful of that uh which we are um so and we speak very openly as a three um so you know we're very mindful of he might have slightly different priorities to us and that's absolutely fine with us.

19:35My motivation in the sort of winning bracket with Trumpet is less financial. I would like a bigger exit, just my competitive side. But it's more the learning of a much bigger SaaS company. So like, you know, a go-to market in America, building a team in America, for example, um a go-to-market for a pure play sass can I do it like I'm challenging myself and I'm just constantly speaking to people that are smarter than me in this field trying to learn and I think I would see trumpet uh when we exit I say when not if um and I want to look back on it and think all the new stuff that I've learned yeah um so it's for me it's more learning without the stress without the financial pressure on my own shoulders, which really does help you as a founder.

20:32And then the exit is the competitive tick in the box, which would also then be great for Rory as well, which we want to make his financial dream come true as well. You said before that your identity was merged with the identity of your first business, Design My Night. How did you solve that problem over time? Yeah, with difficulty. um I did notice like in the early years after I exited like friends and family almost struggled to ask me what I'm doing because they sort of don't understand design my night was even though a lot of them didn't understand what I was doing behind the scenes and the software and stuff they could see a website and knew it was my business and you know how's design my night I used design my night the other day or people would text me like oh I just booked on design my night So even before sort of Trumpet and those new projects, I think they were just like, what, you know, what do you do?

21:29Like, they didn't really understand angel investing, sort of understand podcast. A lot of my friends are not in the startup world, you know, so, you know, didn't really understand the podcasting I was doing. So I think they had to sort of re-engage with me on understanding what I'm doing now day to day. um which is interesting and I think now with trumpet in their mind it's is sort of back back again so they can ask me about trumpet and how that's going and all of that sort of stuff but I suppose the identity I've wanted to create especially with my podcast as well is like a startup guy like I don't see my identity necessarily as an investor and I see myself on the operational side and that's what I genuinely love and whether I'm mentoring advising helping starting operating that's my new identity is is the startup side of things growing and starting businesses rather than I think some people would see me as an investor but yeah it's definitely not the my identity that I want to portray.

22:40So your podcast which I am a huge fan of as you know it's fantastic why did you start it identity is part of it you just mentioned yeah how did the idea come to you it was you know so I grew up watching Dragon's Den um Shark Tank in America um loved it as entertainment I think people forget it's an entertainment show and having angel invested myself and then had friends who were angel investors it just dawned on me that it's so different to what people think and I think a lot of founders that necessarily don't have a network and want to raise money and I still think raising your early money from angels is the best way to go before sort of diving into VC just have no no no idea how you know what a conversation with an angel investor looks like what questions are they ask um who are these mythical angels uh that are investing um you know everyone knows vc names but angel investors tend to not have a brand or a personal identity or anything like that so i just wanted to lift the lid and just be like look everything you're seeing on dragon's den is not what an angel investing meeting is like uh they're not going to give you 50 grand and ask for 50 % of your business either uh you know that's not what you should be doing so i really just wanted to lift the lid on what a conversation looks like um either just with myself and another angel investor from and me i can ask some questions as an operator or sometimes on the format we do is an angel investor will pitch us and we just we have almost that first 30 minute angel investment meeting live on air um and it is all live like they don't know the questions that are coming to them the founders and yeah that's the feedback i love is from founders just being like oh just from that episode I learned that one thing or that one question that actually I didn't have the answer for on my own business or okay seeing how different angel investors think you know we're just people at the end of the day that think very differently and analyze businesses very differently um so yeah it was more I just wanted to lift the lid on that world which seemed a very secretive network driven world and I wanted to be more inclusive for founders that can't just phone up a friend to give them a hundred grand you know you have to go out outbound angel investors on linkedin or on their personal website how you do that how you then prepare yourself for that 30 minute call how do you build fomo how do you give them what you they want and need so yeah that was sort of what drove me for that yeah your podcast is obviously exceptionally successful you're in top three global business yeah it was yeah well then you took a break for a while But at some point, you know, it happened and it's a fantastic confirmation that the podcast is giving value to people.

25:32And, you know, we talked about it. I do think it's extremely valuable what you're doing. I hope you'll continue. I can see how startups benefit greatly from actually listening to how you analyze and your angel guests analyze their particular business. It's fantastic. I hope you keep doing it forever. I am. I know, I know you are. And that's really good. But I'm very curious what it gives you personally, on a very personal level. It's a great way to meet other investors on a more like personal level. Because, you know, you sort of build a new friendship group when you once you've exited, you know, I've got my friends that will always be my friends from school and university.

26:17but then you're meeting new people and so it's a great way to expand my network on less of just like email basis you know it's a bit more personal if they've been on my podcast and I've really studied them before they come on my podcast as well um so so I love that and I love meeting the founders um I love seeing their ups and downs of how nervous they are and And then they're excited and they do the show. And after, you know, whether they're disappointed in themselves or excited in what they've done to go on the show and what they've learned from it. But then I mainly do it for sort of the messages after of just like, oh, I learned that thing from your podcast.

27:02You know, a lot of the content I try and put out is educational. I don't want to do content that's sort of self-aggrandizing and just just bigging myself up every time I put content out whether it's written or audio I do think okay that the target market who's listening can they learn at least one thing from what I'm putting out so yeah when I get the messages confirming that it makes me feel really really good that I'm doing it so you mentioned that you were looking for a new purpose how does your podcast and trumpet fit into your idea of your purpose today seven years after you exited your business so yeah on the purpose side it's um you know the the trumpest side i said i'm more like the cmo um but still a startup guy so i'm fulfilling all of the things that i love doing in in the startup world and that's been really successful for me um and rory was amazing and is amazing as our ceo so that does take the pressure off me and Andrew so I wake up in the morning excited to work on Trumpet not not oh I don't want to look at my emails but sometimes I design my night it felt like that like I don't want to open slack today um Trumpet I very very very rarely feel like that so that's great um and I'm learning a ton um which I'm excited about learning new skills uh we're VC backed um design my night was never bc it was only ever angel so i'm learning that world as well from an operator side um which is great and and then the podcast is you know fulfilling that need for me to to educate people and just meet cool people um to to expand my own sort of personal networks i like to sort of actually build friendships from it as well so do you feel you're in a good place now yeah generally i feel like uh i'm in a good place i have a purpose i'm already thinking about you know what's next I'm always self-checking myself as well you know is this the path I want to be on and go down so yeah I think that's something I never did at design my night so never sort of self-checked in so I'm being more aware of doing that now on a scale from zero to 10 how fulfilled you you feel i would say i'm currently at a seven and a half okay did you expect it to be higher no but it's a seven and a half it's not just seven it's very specific i feel like seven and a half is good um i've got purpose i enjoy my day um but there's more i want to achieve so what would take it to 10 theoretically I don't think I'll ever get to 10 I don't think anyone will ever get to 10 I think that would probably be sort of my post trumpet days and I will look back on my trumpet journey and think okay everything that I thought I wanted to do after design my night what mistakes did I make by going back into operating again so quickly with trumpet and trying to build a big business again so I think I will reflect on that and and see some mistakes that I've made or making from a personal point of view um and I think probably expand my horizon rather than being laser focused to actually think okay how can I how can I have my fingers in several pies and and doing stuff that I enjoy on a day to day across multiple businesses that I'm heavily involved with rather than the one business like I am with Trumpet.

30:49Okay, makes sense. So how does your view on money and the wealth changed from before you sold your company to today? I think there's the cliches that are true. And it's a very privileged position to say but you know the dopamine hit of buying stuff is a is a hit that goes um so as I said luckily I'm not very sort of possession focused but you think okay well if I buy that or if I can buy that I'm gonna feel great and you feel great for an hour and then it's gone again so it's a very privileged thing to say but yeah that that dopamine hit of buying stuff is very much that so that I've experienced that now which I didn't before um so that's good to know in my head that buying stuff isn't going to make me happy I think what it affords you is is time time to try and do the things you love doing and try and give yourself over as a person to be more present with the people that you love.

31:57I think when you're chasing, either it's a salary just to survive, or if you're chasing an exit to achieve that financial freedom that you want, you're just so wrapped up in the day to day. And your day is get up, work, from Design My Night, get home, work, have dinner with friends, but not really be present. And, you know, sort of looking on my phone and thinking about design my night saying go and see my family who I love very much very close with them you know go and see my parents I'm not really being there because I'm thinking about other things I think what having the financial freedom does is it allows you it takes that pressure off you so you know I as I said I look at trumpet not now as like I have it it has to be successful financially for me like that and that just takes a load off you so I'm still working incredibly hard but it allows me to reframe my day do stuff like this without thinking oh my god I'm gonna get back to 100 emails I need to deal with um be more present with my friends and family um and just yeah it gives you that time to think about what what you want to do and and you don't have to do the day-to-day grind.

33:16And, you know, all I'm looking forward to is my one or two holidays a year where, hey, I'm probably going to be on my phone as well. So it's trying to bring that joy to your life. I look at it as weekly. So how can I bring joy, more joy to my life weekly rather than thinking, yeah, one or two nice holidays a year for my joy. way so basically wealth um gives you the luxury of time and presence and only doing joyful activities is that yeah as many joyful activities as you can and when i look at joy it's very small moments so you know i find what are the small moments i just feel calm and happy um and could be you know since covid i've discovered like walking never walked before really um i'd go to the gym and then come home and then i just realized actually i can keep fit walking and i love walking so every day now i will try and have an hour at least walking when my phone is in my pocket and i'm listening to a podcast um or an audio book i'm not thinking about work um and i'm just wandering I'm not even any walking anywhere with purpose I'm just wandering around and I love being in the city so just wandering around London enjoying whatever I'm listening to so it's things like that you know it's not the big moments of joy all the time um so it's where are those little things that I can yeah reflect on and think I'm enjoying this yeah yeah I I do exactly the same thing I can very much relate to it and every now and then I think oh my god I don't feel guilty that I'm not doing some kind of productive money earning activity.

35:05Yes. That actually gives me a lot of joy just thinking about it. A gratitude exercise. So I know exactly what you're talking about. Yeah, that's a good way of framing it. You don't have to be productive slash money making all the time. Yeah, you can be productive in other ways, but not necessarily with this pressure. Yeah, a good example actually. So I love scents and fragrances. um my mother had bought for me a fragrance making course like a one-on-one with a perfumer for a day loved it when then I went back and bought my own ones um and then set up a tiny little lab at home um where I've got all the little the scents that go into making fragrance um and in my head my first instinct was oh okay well I can create some scents create a brand you know did it and my half said to me just stop like just do it for yourself like you don't have to build a business of it you know you love doing it you sit down for an hour and a half or two hours to make a new scent um it's meditative for you you love the output you you wear it you know like you know I'll give some to family and stuff and that's good enough so it was very good that I had that was told to just do it for enjoyment, not money-making purpose.

36:29Absolutely. You know, a couple of years ago, we did this as a family. We went to France to Grasse and we did a professional creation of our own perfumes. And I found it also an amazing bonding exercise with the family because we shared, you know, what kind of fragrances we like. And you never have these conversations. it almost felt like we went deeper into understanding each other through this different thing yeah it's it's such a i could talk about yeah it's easy to miss but it's an important sense that we have it's one of the most important and and people will relate to smelling something and it taking you back to a memory yeah um and scent like no other can trigger your memory like that um and And then as you say, like when you start talking about the different sort of scents you like, and then as you become a bit more skilled in it and go a bit deeper, understanding how layering scents gives the different fragrance and, you know, what a scent is made up of.

37:33You know, a scent is the finished product, even each individual ingredient, but then it's made up of different molecules and how that starts to work. So you can go really deep. And before you make a fragrance, which I'm sure you did in grass, was you you have to come up with a story of okay what is the scent I'm trying to create so you know my first one for example I love Scandinavia so I wrote down I'm you know I'm in Copenhagen I'm wandering around um the the city uh the sights the smell of the city I'm I'm seeing a trendy coffee bar the people are very cool and you're just sort of rambling around um and you know you finish on the water and I'm having a cocktail by the water and you create this story and then you you know what sense then apply to each part of the story to try and build a sense so yeah doing that as a family I can imagine is a really nice exercise actually yeah but there's also meditative for yourself I can absolutely see yeah throw it away and I'm in it yeah and uh talking about presence I think when we engage more senses we tend to be more present uh we are more aware that there are these senses like like smell that we've been ignoring for years yeah yeah and makes the experience richer so much richer and you know that's why now all the from my design my night days all these immersive experiences you know people are just going to have dinner you know there's play there's scent there's uh you know acting there's food so i think society at least the entertainment industry has cottoned onto this to try and give people these more immersive experience because it makes the experience so much richer yeah absolutely um you mentioned that you were exhausted after your exit yeah how did you get your health back I mean COVID was great for that so it feels really bad saying because obviously it was a terrible time for everyone um but I couldn't do anything so actually it just gave me the time to do very little at home without the pressures of having to be social I'm naturally a very introverted person which people find surprising but I find social engagements quite stressful um and and I enjoy it when I'm there but it takes a lot of my energy so I'll leave you know we've talked about meeting up for dinners and stuff and I will enjoy it but then I will leave that feeling very drained you know where other people feel buzzed from that so it takes a lot out of me um so I'm a I am a social person and I spend time with my friends and love them dearly um but I'm a um I like being alone as well so COVID allowed me to fulfill that fantasy of not having to make plans and just being at home not feeling guilty exactly as that I was not feeling guilty I couldn't see my family I couldn't see my friends we would stay connected on zoom and stuff but it was a great excuse just to just just do nothing at home and I'm very happy in that state so yeah luckily that was sort of my regeneration again how about the mental health side of things like did you struggle with depression or imposter syndrome or any other things that are very common in the post exit community as you know imposter syndrome is a funny one like I've talked about that before I don't really buy into it I feel like imposter syndrome I feel a lot of people talk about and then you have to ask yourself with imposter syndrome who are you comparing yourself to that's making you feel like an imposter and most people are comparing themselves to the a plus person in that community that you know they're comparing themselves to which is just unrealistic in anything you know I love design but I'm never gonna be like you know Apple designers and that's fine doesn't mean that when I'm playing around with design I'm an imposter of design and you know we're all just humans muddling through life we've all got our own issues and problems and doubts and I think once you just realize that and you just act you don't have to pretend to be anyone else and I think that's where imposter syndrome comes in especially in the founder community and maybe investment community is you think you have to be this persona of what a founder is or what an investor is and actually you realize that you don't and the minute you get over that will make you a much better investor and a founder so yeah I'm quite anti-imposter syndrome and maybe I have confidence in my own ability and that's where that comes from and but I'm also aware that I'm not the finished product and I'm constantly learning and that's totally fine and I'm going to make mistakes and that's totally fine and I tell my team all the time hey I might challenge you but challenge me back and I might be wrong and as a founder I can be wrong that's fine it doesn't mean you're going to lose respect for me so yeah quite big on that I think my mental health really suffered during design my night but I wasn't aware of it so I think the more we talk about it now is great the towners are very aware of it I just burnt out I just worked myself into the ground um unfortunately enough I could keep going and I did get through it and we got the exit but it was an obsession to to the next level um and as I said there were days that I'd wake up and I didn't want to wake up or I didn't want to open slack or I didn't want to check my emails and that's depression essentially yeah uh but without realizing it um so I'm a lot more aware of that now and that's why I was talking about stress management earlier um that's a big part of that because I don't want to get back to how I felt then and yeah post exit there was that week those weeks wobble where yeah I was very very flat and didn't really have any you know purpose to get out of bed for which again it's difficult to understand if you haven't exited yet because people are like oh you've got all this money you can do whatever you want come on sort of get on with it yeah and I but I agree with that to a certain extent yeah um that's why I said for me it only lasts you know a few weeks and then I sort of got myself out of it and thought come on you're super lucky in the position you're in now let's let's let's crack on um so yeah I got through that um and now I'm enjoying the purpose that I've got so yeah I'm not feeling those feelings post exit how would you define that purpose for me purpose when I was asking myself the question is that having something or some things that when you wake up that you're excited to focus on and that can be across multiple things so for me the startup side was the fun as I discussed about go to market and brand and building something new without the pressures of being CEO but then it's stuff like fragrance so the stuff in like your personal life that you get joy out of and And I think purpose and joy are so closely linked.

44:33And if you can have the purpose in your professional life and then bring out the joy in your personal life and appreciate small moments of joy, I think that's sort of the perfect bubble to be in of the mixture of purpose and joy. Whom do you want to be when you grow up? Thanks for saying I look young still. I'm still a teenager. Um, I, I do visualize, you know, what I will look like, not physically when, when, when I'm older. Um, and for me, it's having made some sort of impact on the community that I love that is the startup community. I'm not going to sit here and be like Mother Teresa and, you know, I want to cure the world of this and cure the world of that.

45:29um I look at communities that I can have an impact on and and I want to look back and think I have made an impact and people externally might have not seen the impact but the 500 founders that have messaged me I've made the impact on them so I really do want to have a positive impact on on the communities that I I love I want to be proud of the businesses that I've set up and there's going to be plenty more after Trumpet um and what I've achieved with them and I I just want my friends and family to look at me and think that I'm a good guy that I that I'm a nice guy I I care about them I love them I will I I want them to know oh you know Nick was the one that we could depend on when we needed him um that's really important to me and something that I probably lost when I was doing design my night um so yeah I think that's that's what I want to look back on and try and be in a healthy position as well and look after my body as much as possible this is such a beautiful answer thank you for it never been asked that before so that was a I could see that you thought about it and came up with a beautiful beautiful answer thank you so talking about your favorite community startups and angel investing which is one of the ways how you give and impact that community you care about so now you've you've you've done quite a lot of investment over 50 yeah yeah yourself yeah so help me understand what you get out of it why you do it and why you've done it for so long and where you are right now in terms of your plans for the future in angel investing yeah angel investing is a funny one so i think it's a natural progression when you sell your startup like back in the day for us I'm glad that's changed now you go to school you go to university you get a job that was your progression um and I feel like the progression is that you start a business you sell it you become an angel investor I feel like that's like the natural progression and I fell into that trap um what I thought and what I do love about angel investing is meeting call founders learning different areas that of business you know I'm very sort of sass focused and consumer website design my life so having my eyes open to that new world um you know genuinely learning from the ones I've invested in because some are doing really well and I'm like okay you know I can learn I've actually asked their opinion on trumpet on a few things even as a investor I'm like oh what would you do and here I'm struggling with this I've seen actually you've done it really well so love that I love making an impact and that's what I thought engine investing would be a lot more of so I think that's the thing that's let me down on it is I thought I would be able to meet meet founders um have have coffees with them uh basically be the operator that I love being at arm's length so my whole stress thing so hey look if I could be let's say out of the 50 I could work closely with 25 of them and my day is meeting these brilliant founders for coffee discussing the business challenges giving my view on it they go away implement it it impacts the business for the positive amazing um when the reality really of angel investing is a you're a money box so you know that's your it's a transactional relationship number one which is fair enough and number two rightly so to a certain extent you know they are their own people they're founders they have their own views on their own business and yes they might respect your opinion but they're well within their rights to ignore it totally And I think I just got started getting a bit frustrated that I was taking the time to really think about replies and helping them where I can.

49:36And it was sort of falling on deaf ears. And then I saw the mistakes happening in the business and then eventually closing or hitting hard times. As an operator, competitive person, that really hit me. And I was like, God, am I enjoying this? like taking all this time to really think about their challenges and how I would deal with them and then it just been ignored and then also the sad reality is a lot of founders don't really keep you that updated so I make it very clear when I engine invest I am here here's my number what's at me whenever I don't pick up the phone a lot but what's at me well voice note any challenges let me know I want you've got my money now I can't take it back so let's be honest any problems you've got let me know and let's try and sort them out um I don't just want your monthly update where I'll reply and you'll ignore me that's not the relationship I want yeah and the sad reality is and I know as an operator things get on top of you but you know probably out of all my investments 50 % send a monthly update max and probably only five or six I have a whatsapp relationship with um and ironically that's what I want I want to help the founders more I'm not just a money person take my money grow it I don't want to hear from you so yeah I lacked the fulfillment and the joy from it and I just sort of asked myself that question I'm putting in a lot of my own financial wealth into this which is incredibly risky as well um and I just wasn't getting the joy from it so sort of where I am now is I still put out a lot of content what content where I'm helping founders um that never stops um but I've sort of taken a pause I think on putting anything net new in um and ironically it's a great time I think because you know valuations are lower so actually if I was doing it from the start reality of making money this year would actually probably be a good year to invest but it wasn't bringing me joy and that that is my focus so I focusing on my current portfolio trying to help them as much as possible get the joy out of that get the joy out of the ones that are working with me closely helping them wherever I can and I hope that if you spoke to those founders you know I would be one of those angels that they're like oh yeah Nick is really helpful and he you know he really tries to help us where we can so yeah I've been on a funny journey with angel investing and I'm sure you know I'll get back into it again and just try and think maybe a part of it is on me maybe I was approaching it wrong as well so thinking how I can approach it differently how I can not have to spend loads of time analyzing decks and all of that sort of thing after all most of my best investments have probably come from referrals to maybe not worrying about all the decks I get sent I don't have to open them and analyze them all you know and don't feel guilty for doing that you can't get back to every founder you know it's not my day job yeah and maybe rely on more referrals and groups I mean of trusted angel investors and just look at those decks um and yeah just maybe reframe what angel investing is in my mind because I think it's very romanticized externally why do you think so many founders are not taking advantage of people like you in terms of getting advice I think because uh and as I said I was in it it's you you're so wrapped up in your day-to-day and we like that with trumpet like we I make a point of stepping back regularly and especially saying to Rory who can we ask to help us you know us three have like an hour intense meeting about some form of strategy without them thinking oh one someone on our advisory board you know took this product to America and scaled it to 100 million what let's get them on the phone now like let's not us three try and thrash it out and I think a lot of founders just don't think like that they get caught up in their bubble yeah um that's all they focus on and And they almost see updating investors as a chore rather than actually something that can be super positive.

53:41So you have VC investors now in your company, Trumpet. So do you think that the lessons you learned as an angel investor is helping you structure your relationships with them differently? Yeah, and we were fortunate enough to be able to pick the VCs we wanted to work with. And we were very clear that we want help. and actually the ones that have invested in us are smaller so we didn't want the tier ones and it was a great decision because you know the ones that are around us are mega helpful every monthly update which we send on the first of the month without fail even if it's a weekend they will get a monthly update the top thing of that monthly update is asks so if you don't read the rest of the update the one thing we ask you to read is our asks yes because what we're putting in there is important.

54:31And we've got most of them on WhatsApp. So yeah, I'm trying to follow those things. So we're like, oh, actually, can you help us with this? Or can you connect us with this person? Or we're thinking about pricing, do you know someone we can speak to about pricing or something? So yes, we're trying to use our investors as much as possible beyond cash. So I know for your podcast, you've interviewed a number of exited founders, you also have them in your network do you think that most existent founders who get involved with startups do it for more or less the same reasons as you or yours are different than what you see in others I think if most were honest with themselves financial freedom would be top of the list um I see a lot of founders you know they I want to make an impact or um you know I don't want to work you know I want to do my own thing I want the freedom I'm going to get so much enjoyment out of that freedom um but I think if people were honest with themselves especially the first one is financial freedom is is a big part of it um so yeah I think I think that is the same for for most founders that's founders but I I was even more curious about what exited founders get out of being angel investors ah okay um i think most they want financial rewards and and look angel investing is incredibly risky but the stats are out there the vc funds historically outperform most markets um so if you can get access to the right deal flow it's important um and don't make just rash decisions with angel investing it can give you a very good return so i think that is definitely top of market for most people but i genuinely think most ex-founders are it's that arm's length but still involved i don't want to be an operator anymore because i'm exhausted but i still want to be in the ecosystem and i still want to be able to influence a startup um but then yeah I would say the reality of that is very different.

56:44Yeah, yeah, yeah. Okay. So you see your experience is quite typical comparing to exit founders you see. I think so, the ones I speak to, yeah. So you mentioned friends and the relationships you had, how they changed after you exited. So I'm very curious about that. How do you find your exit affected your romantic relationships, but also your closest friends and family? Yeah, I think apart from the not really understanding, look, when you meet people, you know, the first thing you'll sit down and talk to with your friends probably is how's work? How's work? What you're up to? So when people don't really understand what you're doing anymore, I think that that was the difficult part.

57:31I don't think it if anything it's made me I would like to think a better friend because as I said I'm more present I can give them more time and I'm I'm really there when I'm meeting with friends and enjoying each other's company I don't think it's changed the sort of financial aspect just so that the type of person I am I'm not materialistic I don't have any social media apart from LinkedIn so I'm not one for like posting you know a selfie of me on in a suite with an infinity pool or something. I keep that to myself when I'm enjoying my holidays. I don't need to share that with anyone. That's not what brings me joy.

58:08Other people being like, wow, look at what he's doing. So my actual relationship, I hope my friends would agree, hasn't really changed me at all. And if anything, yeah, it just makes me more present when I'm there, same with loved ones. Okay, great. Did you have the situations when you had to say no to money requests from friends or family? No, I think the friends I've accumulated over the years are close enough to not bring money into it. Okay. You know, my friends have all done well as well themselves. I have offered to some friends that have been in a bind and I've said, look, I know this is really awkward and you probably don't want this.

58:52But I just want you to know that the situation you're in, if you need any help and if it just stays between us two, that's fine. I'm I can help you um so I have made that clear to some friends but yeah I think the friends I've got wouldn't come to me unnecessarily um asking for money same with my family I'm from an entrepreneurial family so you know they've they've done well so I like to sort of gift them things and treat them to things um but you know my parents haven't had to come to me like can you pay off our mortgage type type relationship with money so I'm lucky from that aspect but I you know as in I would have helped them anyway so your parents were entrepreneurs as well yeah do you think this is why you became one I think it opened my mind to that as a path you can go down um so I always saw that from my mum and my dad separately in separate businesses um yeah not going to work nine to five um working incredibly hard long hours um but then like my dad's office especially I would go into when I was a kid and run around and get to know the team and that was normal to me that dad set this up he's the boss and you know I'm the boss's son and I'm running around causing havoc um so I don't think it made me want to become an entrepreneur but yeah it opened my eyes to the normality of that because I think with anything you know that's why there's a problem with like minority founders because if you don't see something you don't think you can achieve that or that's normal so I think having an entrepreneurial mum and dad it was just normal to me yeah having said that when I said I'm leaving L 'Oreal to do design my night they were like well what what but you're doing so well there and you love it and you've got a career there and you go to Paris.