Financial freedom after 'The Craziest Exit Day in History'™ | Nick Telson-Sillett [REPLAY]

0:00Did you start it with any inkling that this would be a 30 million dollar business? We had a very clear intention on where we wanted to take the business. And we became very intentional. So we became very revenue focused and very profit focused. Instantly global, instantly huge opportunity. It did nearly fall through on the last day. Well, we're going to go there. This is called strategy and tragedy for a reason. What the hell happened? And we just sat there in silence while this person was on a call with the acquirer. Yeah, we were panicking. We were like, is it all going to fall through on the last day?

0:35We ended up in A &E until like 1am. And then, yeah, I remember the next day I was like, I'm just going to stay in bed.

0:45If you've ever booked a fun night out before, then the chances are you've come across Design My Night. Founded back in 2009 and sold for over$30 million 10 years later, the founder has since gone on to angel invest in over 55 startups via Horseplay Ventures. and is now the co-founder of Trumpet. Nick Towson-Sillett, welcome to the show. Thanks for having me. Amazing to have you here on the show. Thank you so much for coming on Strategy and Tragedy. So obviously Design My Night is kind of the headline, the headliner, and I'm sure you're sick of recounting the early days, but we are going to rewind the clock and go back to the start.

1:23So what I love about your founder story is that I feel like we've all been there, where we've all been out with friends on a night out, and we've maybe had a couple of beers and we all come up with this great business idea and we all get excited we have to do it this is the best business idea ever but this actually happened to you yeah and it was actually an amazing success so tell us the story of that one night in New York City when Design My Night was born yeah so we so when I say we is Andrew my co-founder so we've been best mates since day one of university actually and um yeah we were in new york um out for drinks quite a few drinks um and we yeah we we don't really remember whose idea it was but we were sat there the concierge of the hotel was like you know where what type of night do you guys want what type of venue so i think that was stewing and then there was a website we used that had lots of deals in New York and one of us we can't remember who we're like oh if you can combine that and maybe make that into a site in London at the time this was back in 2009 210 there was only like time out and not many others actually so it doesn't sound very revolutionary and it wasn't very revolutionary but we were like let's just do it better than what's out there and yeah it started from from that night and then we we came home carried on research and then decided to to get on with it amazing there's already there are so many little nuggets and little lessons even just within that but one of those you just said there is not actually doing something like revolutionary but just a bit better than what's out there and you kind of taken me back I think 2010 was when I first came to London and I remember I didn't know anyone I was looking for fun things to do and all I would do was go on time out so how exciting I love also how I hear the story quite frequently about seeing something over in the states and then bringing it over here So, all right.

3:22So what happened next? So you started Design My Night and did you start it with any inkling that this would be a 30 million dollar business in 10 years time? No. So at the start, we weren't thinking like that. So I worked at L 'Oreal doing marketing. Andrew was at Accenture and we carried on those jobs. So we built Design My Night for a year. The classic story like weekends, weeknights, we'd meet up pretty much every weeknight, every weekend and build the platform on weekends. Once the product was actually launched, the site, we would doorstop bars, pubs. It's not as fun as people think it was.

3:59We were doorstepping them in the day before they were open, trying to speak to the managers, really understand what they wanted in a discovery platform. that's what we called it um and you know what they liked about timeout what they didn't like about timeout and just trying to gather all that knowledge and it's a great trade to work in very giving people very friendly people um so we did that for a year um the site grew slowly slowly slowly and we're like okay we could be onto something here um and it was actually a moment my boss at l 'oreal at the time is a very good friend of mine now he pulled me aside and he said I know you're up to something because it was an open plan office he's kept seeing me like run into meeting rooms and he was like I just want to remind you that in your L 'Oreal contracts you can't start anything else while working at L 'Oreal okay and so he he and he knew I was entrepreneur and wanted to do my own thing so that was a bit of a jolt so that was like okay are we going to do it are we not going to do it so can I just jump in a quick sec so sorry because so what I thought you were going with there was like something competitive like obviously but like nothing entrepreneurial at all or at least I think have to like tell them and get advice or um I didn't actually look at my contract after then um but that that was just a job we almost needed um I so what we did was I I left pretty soon after that Andrew stayed at Accenture um and we split his salary for six months um so we could still survive um carried on working nights and weekends and then after another six months and you then came on board fully so it's actually like 18 months since the idea to both of us working full-time on it interesting so you what was the deal then so he was okay to so he continued working so you could split the salary yeah and the deal was you would have your time yeah so I was full-time on on design my night interesting okay I've never come across that before amazing and i love also just going back to how you were literally like food like feet on the ground like going around the bars restaurants actually talking directly to people i think for me and we still do this today so before we launched trumpet which is in the sales space we spoke to 150 sales people i think um you know a lot of founders hide behind their desks or their laptops now um where actually you have to just get out on the ground and speak to people and and they come up with the best ideas so a lot of the early ideas for design my night we when we pivoted to software as well which was the game changer for us that was a marketing manager of a bar chains idea it wasn't our idea um so if we're not constantly speaking to them you're going to miss out on some incredible ideas oh my god amazing gang whether or not you like it if you're in business you're in sales full stop and in today's day and age there is no excuse not to leverage the best tech to make you smash your sales and commercial strategy.

6:53Because here's the thing, I bet whichever CRM you're using is simply telling you what happened after the matter, but gives little to no insight on why deals are stalling or closing. That's why I am genuinely so happy to tell you about Gong, the revenue AI platform that turns every customer interaction into actionable intelligence. Whether you're trying to improve prospecting, sales productivity, customer expansion or revenue predictability, Gong offers a single AI platform purpose-built for revenue teams. Identify what separates your top performers from the rest, surface the objections that kill deals, reveal the patterns behind your wins and losses, and know exactly which messaging resonates with prospects.

7:36With powerful tools to understand every customer interaction, you can finally put an end to the guesswork and start scaling what actually works. Honestly, gang, this is such a cool tool for building sales machines. This isn't just about better data, it's about predictable revenue growth. Now, while your customers rely on gut feelings and outdated playbooks, you'll have an AI-powered insights driving every strategic decision. If you're ready to turn your sales conversations into competitive advantage, then head straight to the show notes for your unique Gong link and see why thousands of revenue teams trust their growth to revenue AI because in sales, strategy beats tragedy every time.

8:19All right, gang, let's get back to the episode. Okay, so picking up some steam. So you're both now kind of full time on this and it's kind of growing. I read also that you only took what was it like 500k investment in total. It wasn't a huge sum of money, especially compared to today's standards. And you turned that into an ultimate but 30 million. So congratulations. So how, how did you, how did you grow the company? So like you had 500 K, was it just a case of like, we only need a little bit more just to nudge the product market fit. We've already got all this great traction or. It was even slower than that.

8:56So we probably didn't raise the first slot, which was 250, probably three years into it. So for the next 18 months, we were just growing the business. We were very big on SEO, so we didn't need to spend that much on marketing. The great thing about that industry is there's just tons of searches. If you think in London, rooftop bars, and then it's rooftop bars in Shoreditch in the West End, in Mayfair, especially in London. So there was all these customers out there Googling stuff. So we were like, well, if we can get that market, we don't then need to spend a lot of marketing. So we work very hard on SEO.

9:34and to this day luckily if you google most things design my night's number one or two so that's how we got our first sort of traction was pure SEO didn't need to spend much had sort of interns working with us then we raised 250 which allowed us to hire an editor really sort of kick on the business we sort of implemented bookings into the platform as well again very startupy we just decided overnight let's start taking bookings so we just put make an inquiry button on every bar page on the website um and then when you made an inquiry on the site it came through to Andrew and I and we were just booking people in manually uh 24 7 um trying to give people a great experience the whole mechanical Turk thing right yes yes behind the scenes going that's literally what we were doing um and at that time booking into a bar was really difficult so there was no booking software um you would phone a bar no one would be there till six o 'clock and when you did it was the manager picks up he doesn't really care about taking bookings so we were like okay if we can just provide a better service than that so we would text them and say oh we haven't managed to book you in yet but we're working on it and then when we did book them in we sent them a text um so all very basic stuff but just elevated the customer experience um so did that got more revenue then could reinvest that back into the business through bookings.

10:55Then the next year, so year four, was when we launched our software, so our booking software, which was the total game changer for us. And then we raised another 250 from the same six angel investors to kick on software. And so that was exactly what I was just going to ask actually. So the reason for taking external investment was purely for the product development mainly for that. Yeah, because we then had to sort of pivot internally as well. So before that, we were a very editorial team but obviously launching software we needed more dev we needed customer success account management sales um so we sort of stripped back the editorial team uh hired more in the software space um and then cracked on into becoming a software platform as well it's amazing it must i mean even just kind of going down memory lane a little bit now to like the 2010s what a different time like not that long time not that long ago but completely different in terms of everything talent tech VC the rest of it would you agree because you were obviously there and building yeah you know London yeah the especially raising money there there was it didn't seem that there was all these angel investors and individuals that could give you money the VC world was very much um Silicon Valley San Fran based um so it didn't feel very realistic to raise money even um yes people wanting to work in startups you know it's less of a leap of faith nowadays you know working in startup is what a lot of people want to do um so it's a very different scene um interestingly it's similar it was in a recession so 210 it was a recession um which actually worked out well for us because we learned that brits in a recession still like to drink so they didn't go on holiday but they wanted to go to the pub or a bar so actually for us the nightlife space during a recession was actually very boring yeah that's hilarious so good for you I so I was gonna ask like given it was such a different time is what what worked for you back then that you think would still work for a version of design my night now but I might revise that question because you said that actually that was in the last recession things were tough then yeah So do you think that like if we were to pick up the 2009, 2010 design my night and put it into present day?

13:18Yeah. Do you think that I mean, I know we can't A-B test or anything. Right. But like, do you think that you would come up against the same challenges? Do you think the stuff that worked for you back then would still work for you now? Yeah, I think I'd still play the SEO game from a B2C point of view. obviously post-COVID you know my contacts and hospitality it's recovered somewhat but it's more of a recession on the bar side this time than the consumer side so I think they're a lot stricter on the money they spend the software they buy so I think it's a tougher market to sell software in at the moment just because the economy's so unsure but by all accounts design my night's still doing very well um for the contacts i have there so it's still the same model for design my night is still pretty much in place and it's still pretty buoyant so doing things a little bit better and uh and prioritizing seo as part of your marketing channels is there anything else that you would attribute your success to with design my night i think anything you'd do again i think the team the way we built that team um was um Not that planned.

14:33We were early, mid-20s, so we fell into managing big teams and growing teams. But that sense of unity we had at Design My Night, the early team, and I say this when I speak to founders now, that first 10 hires are the most important. Not necessarily in terms of skill, but they have to believe in the vision. they have to really like you as founders and then they become your sort of eyes and ears as you grow so when design my night when we sold were over 100 people i think nine out of those 10 were still there um and they were the ones when andrew and i couldn't be on the ground or on team nights out they were the ones you know pro design my night um so making sure they're the right type of person that really believe in your vision and want to see it through to the end with you um is is pivotal And we've taken all of those learnings through to Trump it as well.

15:30This is what many call culture, right, is those first hires. It's how you scale your founder DNA without codifying it in SOPs or doing it in a more rigid kind of structure. But it's just that kind of vibe culture. It's that sense that, you know, culture is banded around a lot. And we were pre-COVID, so obviously everyone was in the office. So we had 100 people in an office in Hoxton in London. so the vibe was amazing it's got a young team as well um obviously they were getting three nights out and all of that stuff so it's like a very just fun environment to be in so people loved to work there um it's a lot harder now with flex working and and not having an office um but for me the founders are the ones that just yeah the the the untouchable thing um And I think as founders, it's more actually about the sense of who you are.

16:28So, you know, I always want to be very humble with the team. I want to be very open with the team. The team know that sometimes a founder needs to put their foot down when things aren't going well, but it doesn't come from a sense of, you know, being the leader. It's about driving the business forward. It's about having a clear strategy. It's pulling everyone along with you for the ride. um so it's all of those sort of untouchables um that go beyond perks and mental well-being and all of that stuff that's important but that has to come from the founders yeah absolutely i feel like the perks is just it gets the engines going in a job description and he's like oh cool that looks you know maybe i'll put a bit more effort into the cover letter right then when you get in there you're like okay thanks for the bean bags and you know free popcorn yeah I mean if you hate your day-to-day work but get a free gym membership right it's probably still not enough to convince you to stay yeah I don't think yeah this is the sort of stuff that I feel like you only learn through experience as well I mean you said you're in your 20s it was a young team and you're just kind of thrown in there so we start to kind of move things along and so the exit is on the horizon so like what was that process like for you selling design my night so obviously at the very beginning you didn't have that foresight those intentions which is just kind of like let's give it a go you both had your day jobs anyway but now it's like okay this is going well yeah where did that process start for you then so it was after the second round so four years in we had a very clear intention on where we wanted to take the business and Andrew and I set ourselves a four to five year horizon and we would talk very openly about this with the team so the team knew we didn't want to stay at design my night for 10 15 years they all had shares as well so we were like if we do exits for your good as well um and we became very intentional so became very revenue focused and very profit focused because in our heads we were like if we can build a profitable business and a growing revenue business at the same time your exit chances are going to be much bigger so it's not just an industry buyer but it could be private equity as well if you're spitting out cash.

18:37So we, not that we were ever big spenders, because we only had half a mil from investors, but we were very careful with what we spent, we made sure most things that we spent were sort of revenue drivers, we were very focused when it came to product on, you know, what's going to stop churn and get new customers on board. So just all the basic metrics that sometimes founders forget, that become the revenue levers. And what we actually did was we looked at exits in hospitality and started to plan out a rough multiple of revenue and profit. And Andrew and I agreed a sum with each other five years previous on what we would be happy with as founders.

19:20And then we just multiplied that up. So we're like, okay, we need to have this much equity. We need to sell the business for X if we're going to take Y. And we modeled it out and we were like, okay, so in three to four years, we need to be at this revenue and this profit. And then we've got a good shot of selling it for what we want and we track that quarterly Andrew and I had a chart that we're tracking revenue profit on our exit trajectory and actually a year out from exit we were like okay next year we're going to be at those numbers let's start engaging so we engaged a broker so it wasn't the dream scenario that people were reading TechCrunch of you know OpenTable emailing us saying we want to give you a hundred million dollars so we engaged a broker and that was like an eight-month process from engaging the broker to to actually selling the business interesting I'm just going to back up a sec there because uh hey you make it sound so simple and easy this is like three-year-old maths here like yeah just you know how much do you want no but I've definitely come to learn the importance of of that decision making and charting your own course whether it's in business or otherwise and being like okay well how much you want and let's you've just got to put the stake in the ground somewhere to then start developing a strategy around that so I love that and then one thing I wanted to come back to is your two focus areas of the revenue and the profit that you mentioned I don't know whether this is just too many years in the nitty-gritty of marketing land but to me they sound like you know sometimes they can be in opposition to each other right because either you've got the I'm sure I'm oversimplifying this but you've either got the revenue focus which is like gain market share at all costs which can then of course be more expensive to acquire which eats into your profitability or it is no we're going to double down and have more of that quality so how did you manage to achieve both the revenue the market share and profit margins well I think it doesn't to have to be as binary as A or B.

21:23So, you know, when we wanted to focus on both, the revenue arm wasn't necessarily, let's go global. So we had every month someone wanting to take us to a different country. We were like, no, don't need to. We can achieve the targets we need in the UK. There's enough big cities in the UK. So we sort of knocked that on the head um and the beauty of software which is why i love sas is um once you find the model so a once you've got product that people want and it's good that's the first bit the actual scaling up a sas product which is why venture vc love it is you don't it's not like growing a d2c brand where actually it's just sales people um and actually you just model it out okay well one customer success person can look after 150 customers those 150 customers might be worth a million annual revenue to us and it's looked after by one customer success person a sales person once they've got the playbook right let's say they're earning with commission 80 grand a year but they're bringing in 300 400 grand a year you just add another one on you're like okay well we've got the product we've got the playbook this person's costing us 80 grand and making us 400 grand let's add another one and then once they start ticking let's add another one and once the customers start spinning up we add another customer success person um so the beauty of software is you can do it both i think the the boom or bust that we see in the world at the moment the ones that spring to mind you know like your ubers actually just turned profitable i believe um weworks you know all of those are more b2c which is more marketing land of you need to spend the dollars and go global quickly big but in sort of sass land and I think now VC have wised up to that like you don't have to do boom or bust to grow a very big business that is also profitable it's simple maths again isn't it and I'm really bad at maths so I keep it simple if all else fails you can always go back exactly for kindergarten basic maths I love that quick one this is future Steph coming to you from beyond.

23:39If you're enjoying this episode, then you can probably guess what I want you to do. Please do me one tiny favor that costs you nothing and takes a second of your time. Hit that subscribe button. It really helps to support the show. And I'm really grateful for you listening. Let's get back into it. Okay, super interesting. So you so coming back onto the exit. So that was an eight month process you mentioned. And I guess first only last time that you've that you've gone through that whole exit so i've never been through this so what was that like if we were flying a wall yeah up the road at the hoxton offices yeah what would we have been seeing during those eight months of the exit process of selling design my night if you're in the office you wouldn't have seen much so you have to keep it very quiet so the team didn't know we were exiting until the night before so apart from our finance manager obviously who was helping us prepare everything so um you have to keep it very quiet um and our broker was great and basically the sort of first four or five months uh they're building the story with you so they come in they want to understand the business um design my night when it came to exit was quite complicated so we had the b2c arm we actually had three bits of sass by the end uh all very all different revenue models um so they really had to understand the business they remodeled the business with us and then you put together something called an IM, which is essentially like an 80 page slide deck about like where you've been, where you are, where you want to go.

25:06Um, and that literally took like three or four months with the broker. Um, and then they start shipping you out to people. So, um, we drew a list up of all the people we thought would want to buy us. So the obvious ones were us. So like TripAdvisor, OpenTable, et cetera. Um, they had ones we'd never heard of and ones in Asia, et cetera. and I remember the day we drew up those lists the broker said I guarantee the acquirer won't be any any of these lists he was like it always happens that way and our crowd wasn't originally on any of those lists and yeah it starts shipping you out you start sending out the packs the broker does it all to the heads of M &A at TripAdvisor and all of those and then you just go through interview processes so if they're interested they'll have like a 20 minute chat if they're more interested they'll pull you into the office and have a chat with the CEO and the head of M &A.

25:58Then if they're still interested, they'll probably get someone in from the business to chat to you. So with our acquirer, we probably had about six chats to get to offer stage. We had three offers on the table at the end. Then you enter negotiation with those three partners. It's about a month negotiation. Then you sign exclusivity. so we signed exclusivity with one that our actual acquirer um and um then you go into due diligence um so due diligence for us was about a month which is quite light um and then if you get through due diligence you then sign the papers wow how did this compare to like the fundraising process like it sounds pretty similar to like you know lots of conversation yeah it's it's more it's a it's a weird feeling of excitement but not wanting to get carried away yeah same as fundraising I suppose but you know we'd worked so hard to get the business to where it had and the one thing Andrew and I would always say to each other was what if no one wants to buy it like okay great you're doing this and this but what if no one's interested you're like you don't know that anyone wants to buy it especially at the number that we wanted so um it was that nervous excitement um but as the groundswell starts to happen and you have more and more conversations they're more interested and then offers start to come in um it's it's yeah it's a very strange scenario our broker again did say do not celebrate until you literally sign the paper and for us it did nearly fall through on the last day um so that was a absolutely crazy well we're gonna go there this is called strategy and try to do for a reason what the hell happened there was so we were meant to sign the papers so the night before we told the team we pulled the team in and our lawyer said to us okay we're going to go to the acquirers um legal offices fancy legal offices in in central london um i think it was at like half 9 a.m we'll sign the papers they're going to take you out for lunch and then we were going to celebrate with our team we booked a bar for our team um and we said oh we'll meet you at like 5 p.m at the bar um and then we got a phone call at like half 7 a.m from the lawyer it's like can we jump on a call we were like yeah and there was a new eu law around payments that come out and we had a payment system in our product we'd never heard of it and he said the acquirers would like to know what your view is on this new payment law and we were like we said to our lawyer we have never even heard of this law and they're known what we're going to do and they were like well they want to know because a payment was a big part of our platform um so we used stripe at the time so we phoned up our stripe account manager and we were like you know we couldn't tell him we were exiting so we were like we need you to jump on a call with our board members to explain the new law and he was like asap like quarter to eight in the morning and we were like today he said I can't tell you why but this is the most important thing on your agenda today and it gets it wasn't because he was like I'm on the way to hospital because my wife's giving birth oh my god so we were like okay we were like brilliant well done uh is there anyone else um and he was like yeah I'm sure I can I'll get someone else to do it because we were like it's really important but we managed to get someone and we just sat there in silence while this striped person was on a call with the acquirers even You know, we said it was our board members and they were asking him all about this law.

29:27And that was at like three o 'clock by that time. Do you remember what you were feeling on this day? Yeah, we were panicking. Going through the ring. Yeah, we were like, is it all going to fall through on the last day? Oh my God. And then, yeah, we put the phone down, just sat and waited. And then an hour later, the lawyer phoned and was like, they're satisfied. Let's go to the lawyer. So we didn't get to the lawyer's office till like five, six. um finished finished signing the papers at like seven obviously they didn't take us out for lunch um and we didn't get to the bar till like eight where they drunk all the champagne and they were wasted and we rocked it don't eat the champagne anyway give me the hard stuff so yeah we and then as you remember that night one of our team members tripped up and smashed her face on the table so we ended up in a and e andrew and i with her uh till like 1am um and And then, yeah, I remember the next day I was like, I'm just going to stay in bed till about 11 and just recover.

30:25So it was a wild exit day. Oh, my God. This sounds like just the stuff of, like, films and books. What a rollercoaster. Do you remember the date, the exact date that was happening? I do, actually, because one of my best friends had twins who were born on the same day. Oh, my God. What is this? All these people being born on the same day. And I'm godparent to the twins. So when we celebrate their birthday, he always says happy exit day as well. I can't remember it now. It was recently. It was in December. Jesus. No, end of November. Yeah. So it was crazy. Wow. So you've also got just like winter and cold and everything as well with all this going on.

31:05My God, Nick, I feel like I need to like catch my breath after that. I mean, just hearing the story, like empathising with that. I'm like, bloody hell. Like that's that's given my heart a run for it. It's good fun. I guess that's where you must have been so thankful to have a co-founder with you during all of that as well. Could you imagine being on your own? I say the whole ride I can. I have a lot of admiration for solo founders, even as an investor. I'll be honest, I prefer to invest in two or three founders because I just know how hard it is. You'll know how hard it is. Well, thank you so much for serving that segue on a platter there, because moving on from Design My Night.

31:44So congratulations, you exited and got to have a lie in the next day. So you set up Horseplay Ventures, which is your vehicle, as I understand it, for angel investments into other founders and startups. So thank you for half answering the next question, which was, of course, what is it that you look for in your angel investments? So we've got a couple, two or three of founders. That's the first kind of checkbox. What else is it that you look for? We've always been pretty sort of sector agnostic. I think Andrew and I's philosophy is we just need to understand the business. We obviously really understand SaaS and we like SaaS.

32:20So software is big for us. We've invested in some D2C brands, but I'm not the biggest fan of D2C brands. And it's not something I'm that knowledgeable on, you know, like Google Ads and CAC and all that stuff. um so yeah we've invested in loads of random stuff from like agri-tech uh to like robots that make coffee uh to more standard stuff that i fully understand some very similar products to design my night but in different um areas um and we're in yeah like 55 56 now um is there a commonality that most of them all share we're looking back now you've got over 55 is there something that you're like okay that's that's actually the magic i think the best the best ones because they're not all great um the founders so the ones that are really working well um and there are a few that are solo founders actually um the founders just have that something special that when i speak to them i'm like and it's very difficult to explain but i just get that feeling that you get it you get what you need to build you get how hard it's going to be you really understand the market you work in and that's really important to me um you don't have to have worked in the market I never worked in hospitality but we researched hard and we were speaking to bar owners all the time so I really quiz founders on you haven't just come up with an idea about how well do you know the problem you're solving how well do you know that pain point um all of the ones that are doing really well all tick that box um is that where they say you know there's like a touch of like founder crazy that all successful entrepreneurs have yeah I think you I mean you do have to be crazy to start your own business like I think it's been glorified a lot um on social media but it's the hardest thing you're likely to do um I hope for people that there's not harder stuff than that um so I think you do have to be a bit nuts to start your own thing um and I just it sounds really now I just look for good people you know you you people idolize the Elon Musks and the Bezos of this world.

34:30And obviously, they're a different form of genius. You know, unfortunately, I don't get to invest in Tesla when it was a pre-seed investment. You know, you don't tend to meet those people. So the founders I meet, I'm just like, can I see you running a team? Can I see that team following you? Are you a decent person? Are you going to make the right decisions at the right time? And have you got that route? You have to have a ruthless streak you can't be mr or mrs nice the whole time but just if you're a decent person you're more than likely to bring customers and your team along with you it's it's really interesting i feel like we could just literally talk for hours on like the founder profile and what it takes to be a successful entrepreneur and i was just chatting with my partner about it the other day because he is incredibly smart like he's studied at cambridge he's super intelligent he's a lovely guy obviously i'm a bit biased but you know he's decent he's got like a lot of these traits going for him and he and he's not at all in the in the entrepreneurial startup world which i am he was like oh could i do you think i could be a fan i was like definitely not and it's like you're you could be so amazing at so many things but like you my view is after working with over like 100 founders over the past like five plus years as well is I feel like you have to be so outstandingly excellent at so many different things in order to be a successful entrepreneur like you have to have i just feel like you can't be halfway on one or two of the things i mean you can you still be great still you know have a great business whatever but to really be like to really make it yeah be a real and then you've obviously you've got your the luck of the draw and yeah macro external factors and everything else into it i sort of look at it that i'm like if if you are exceptional at one thing um that could be marketing that could be sales it could be product design whatever um and then good at everything else because the first two years you have to do everything um i think that's a a good way to go i i also look at founders can you sell i don't care if you're an engineer um or if you're normally behind the laptop like the founder has to be able to sell if one of you cannot sell to investors to customers to your team you have to be a salesperson um so that for me the best founders i've come across have that sales instinct as well such a fundamental skill isn't it we don't get taught it we don't get enough training in that no um you are great at handing me these segues on a silver platter nick because the whole selling and having a great sales skill set brings us onto trumpet which is your new venture now right so tell us what is trumpet so trumpet is um digital sales rooms um for sales teams to collaborate with their buyer so we looked at we look back at design my night actually and we were thinking okay what what what could where could we have implemented tech into design my night where we haven't before um and the sales team we were like they're just starved to technology like on the one hand you've got your outreach tools to try to reach the person and on the other hand you've got your crm where you're logging everything and then you've got that whole thing in the middle of getting the deal done which is over email and pdfs and slides and we're like there's just no technology there so we wanted to create these digital spaces where you can collaborate with your buyer you can drop in case studies and proposals and video and audio and create a really collaborative space for you and the buyer to get the deal done.

38:19That's ultimately what you want. If they're interested and you're selling it, how can you get the deal done better and quicker for the buyer? So that was the original premise is how can we make the buying experience better? The sales industry is very focused on how do you make salespeople better hunters? But actually, buyers don't want to deal with hunters. They want to deal with authentic people that are helping them get the deal done over the line quicker. So that was the sort of the initial thought process two years ago now. And now it's this huge trend, luckily, called buyer enablement, which is all about helping the buyer get the deal done.

38:54So luckily for us, Trumpet is a buyer enablement tool and is sort of riding the crest of that wave at the moment. OK, amazing. Congratulations. I've been following your journey and it all. You've really embraced the whole building in public kind of thing, right? Was that a conscious decision? And if so, why? Why are you being so brazenly transparent on LinkedIn especially? Yeah. When I sold DMN, I knew I would do something again. And I just made the conscious decision to build a profile. It's easier once you've exited so people sort of want to hear your story. But in my head, I thought if I can build a following, then it will be easier to sell to that following.

39:36um so for like a year after I exited I worked hard on LinkedIn I don't have any other social media in my life so I have no sort of personal social media I don't really want that in my life and I focus on LinkedIn um and it's been amazing for me like Trumpet when we launched we had like 5 ,000 people on the wait list I would say 70 % of that came from LinkedIn originally a lot of our customers come from LinkedIn seeing what we're doing sales people are on LinkedIn It's the natural place to be. And yeah, if you share the highs and the lows, you show you're authentic, you show what you're trying to build, that will naturally allow people to come to you.

40:14And like Design My Night where SEO was free, LinkedIn is free. So Rory, who's our third co-founder in Trumpet, I schooled him on how to build a LinkedIn profile and he's amazing at sales. So he does a lot of sales education on there. He's nearly caught me up actually in followers in much less time. and we encourage our team to be like get get on LinkedIn share the journey share learnings and it's been amazing for us like yeah I absolutely love it I've definitely seen all of it happening as well so I can see all the fantastic success that you're having on there I love also how you're like oh this was the free thing that worked for us back at you know DMN 10 years ago with the SEO and then this is kind of the equivalent now in like modern day you just mentioned about encouraging the team as well how have you got any practical tips about how to do that because i've always been very you know your linkedin profile is yours it's your personal but i try to inspire and set an example but i how how do you go about kind of motivating others if they're not yeah i mean you can't force anyone so we don't say you have to be posting on linkedin our managers our leaders in our teams um we we tell them to it's about building your profile as well like you know you're not going to be a trumpet for 20 years i imagine so start to build your journey now um and show your expertise and i think with linkedin as long as you're authentic um because there's a lot of inauthenticity there and people will resonate with that and you find your tribe everyone's got a tribe in some instance you know me it's more founders rory it's more sales people our head of customer success there's loads of cs people on on linkedin as well so like share what we're doing share your learnings help people um as long as it's not a one-way street um a lot of the content i always say is it's about can the reader take one thing from that post or the podcast or something and if they've taken at least one thing from that post then it's worthwhile and they'll engage with it if you're just telling them how good you are um it's just not serving no it doesn't serve anything it's just the the chest beating which there's definitely enough so what are you doing differently this time around with trumpet i was going to ask you know what made you want to take up another venture because i'm guessing after design my night you don't necessarily need to go through the craziness of startup again but um yes i mean that was a big decision to go again it was during covid so we we sold in 2019 so andrew and i just soul searched yet we were luckily financially free and can go on holiday and do nothing for the rest of our lives but we were like we're too young to do that what do we love doing and we agreed that we just love building businesses and actually just with less pressure this time um and we brought in a third co-founder Rory so um you know he can shield uh a lot of the crap that we don't want to deal with on the second startup which is great he's amazing um so yeah there's that sort of zest for it you know we're doing it because we love it rather than we have to with trumpet um different wise we've we've gone VC so we we we raised money pre-product pre-revenue so very different um very different to the mantra I was spouting before about bootstrapping but there's no one way to run a business and for us trumpet was instantly global instantly huge opportunity every team has a sales element to it so every company in the world can and could use trumpet so we wanted to seize that opportunity which is why we raised VC and that has different pressures different stresses that we didn't have a design by night so we're learning that as well we're learning how to handle VCs as well and the raising game.

44:09But a lot of the core principles we've done the same. It's about the team. It's about building great product. It's about speaking to your customers all the time, sharing publicly how things are going. All of those core principles have stayed the same from Design My Night. Even with VC money, we're still very strict with what we spend. everything has to have a goal to revenue and that is what we are fanatical about is again revenue and getting to profit so it's the same principles but on a bigger scale this time exciting where can people go to find out more about trumpet so trumpet um we're on sendtrumpet.com people think the product's called send trumpet which annoys me because it's a big logo that says trumpet not send trumpet we unfortunately couldn't buy trumpet.com all the time it is well how much the url yeah influences what people think the company is called all the time yeah they're like oh i was looking at send trumpet and i'm like no it's called trumpet does that annoy you yes it was like design my night so many people called it design by night right and i was like that doesn't even make sense what does design by night mean even in interviews people call it design by night and I just like so it's called trumpet but you can go to sendtrumpet.com check it out um if you look for us on LinkedIn as well we're talking about it all the time yeah and do follow them on LinkedIn it is um definitely put out lots of really really help like genuinely like educational inspirational posts um one of which as well um is just to touch on I know that you're really um you know the lgbtq initiative is important to you as well would you like to shed a bit more light on some of that yeah i think like representation as a gay founder like representation is super important um you know it's nuts in in 2023 that uh women are still considered a minority in terms of businesses even though they're 50 percent of population obviously like ethnic minorities um and those are two that are often talked about and rightly so um but obviously the one that i know um is is the lgbt stuff um and yeah just a be a i don't want to use the word figurehead but you know representation for sort of other lgbt founders that you can be successful sometimes that's all it takes being visible being visible um and there's a group of us we've set up something called proud ventures which is a group of investors so mainly VCs actually so people at VCs who are LGBT plus and some angel investors as well and yeah we we did like a conference for found LGBT plus founders all about just being your authentic self like be who you are that will be you will be the best founder if you can authentically be yourself and so we put out lots of educational content we're doing conferences um we want to help them raise money give them feedback on their decks feedback on their business and just create a safe space for that part of the community because yeah it's a very sort of straight white male world still um especially in venture and startup land do you know what was funny about one of the comments that i saw on one of your posts about being just more visible in the space and just touching on that really important representation piece i saw somebody post about um ability uh as in kind of you know disabled and these other these other segments of the population and it was just like it's it's a funny because it's like you open the door yeah to the wider representation diversity piece and it's like but what about this but what about this and you've already mentioned there like women and ethnic minorities and different levels of ability and neurodiversity it's like we are all the rainbow of like yeah but it's funny how some people is like they can't just let you have your story to tell and your particular mission it's oh but what about this but what about yeah and yeah and you know I my whole life I try and be authentic so I'm not a woman um I'm not from an ethnic minority so I will support that um but I can't talk with any authenticity about that or lived experience.

48:30So while I'll always support initiatives around, you know, all the different sectors of society, I think being in sort of the LGBT plus community, it makes you more open to all different sectors of society because, you know, we're so marginalized that I think it just makes you more of an open person because you've seen what persecution looks like. But I can only talk about my lived experience. And that is all I will ever do. Yeah, that makes complete sense. Well done you, Nick. Honestly, I love that. It's awesome. So closing question, the tradition on this podcast. So it's called strategy and tragedy for a reason.

49:11You said yourself, you know, entrepreneurship has been glamorized. And the truth is, it's not that glamorous. There's also the belief that often the best lessons can come from the biggest mistakes. so with that in mind what is one tragedy because your exit did go through eventually yes a few hours later what is a tragedy that stuck with you that's taught you a lesson that you won't forget yeah so um it was actually at design my night um early years probably two years in we i talked about seo a lot so we actually gave our seo to an agency um and andrew and i at that time didn't really understand SEO.

49:51And this agency was doing at the time, it was called Black Hat Techniques, which was like tricking Google, basically. And traffic was going great. And we were climbing up the rankings. We were like, great, keep doing what you're doing, agency, not knowing what they were doing. I remember, I'll always remember, we came in one morning, we looked at analytics every morning, and we lost about 80 % of our traffic. And we just thought it was a glitch in analytics. we'll check back later no still gone next day still gone googled it um and they'd released a new algorithm it's called penguin at the time um which cut out all the black hat techniques um so we just lost our ranking overnight basically um and from that moment on it's always taught me to understand what I'm doing um and not just blindly hand over so bring in expertise but really understand what they're doing and and from that day on Andrew and I taught ourselves SEO and we still work with agencies at Trumpet but we really understand what they're doing this time we just don't have the time to do it so I always try and even on a surface level educate myself on something that affects a business rather than just blindly handing over because that was a very harsh lesson.

51:07Well thank you so much for sharing that Nick and thank you again for coming on the podcast it's been such a pleasure to sit down with you and hear some of your story I feel like you've got many many more but we'll leave that there for the podcast and thank you so much for listening really hope you enjoyed this episode please hit that subscribe button really helps us out and tune in for the next one