Scaling smart, selling big 🎺 | Nick Telson (Trumpet)

I know it's not very PC to talk about now, but you have to work yourself like a dog at the start. I don't care what anyone says, you cannot get your business off the ground without working incredibly hard. Yes, you need to be aware of your own mental health and take steps to look after your mental health. If you are not prepared to put in the hours 7 days a week at the start, it's just not going to be successful. I've never seen a super successful entrepreneur that works like 9 to 5, Monday to Friday. It's just not possible.

This week's Millennial Master is Nick Telson, entrepreneur, investor, and podcaster. Nick co-founded DesignMyNight, which sold in 2019 for over $30 million. Now an angel investor in over 50 startups worldwide, he's also the co-founder of Trumpet, a SaaS sales platform revolutionizing the buyer journey. In this episode, Nick shares his wisdom on scaling a business while keeping its culture, why mastering sales is crucial for startup success, and how to build ambition into a smart exit strategy. Millennial Masters is proudly sponsored by Jolt, the UK's top web hosting service. Whether you're launching a WordPress site or scaling up a custom app, every great project needs a reliable home. That's why Jolt has hosting plans starting at just £3.95 a month, with unbeatable deals on domain registrations too. Why Jolt? It's a no-brainer. There's no waiting around with support within 30 seconds on live chat. Your site stays live no matter what with over 99.99% network uptime. And you can also pay with Bitcoin or American Express, so you can rack up those points too. How good is that? Sign up today and enjoy your first 3 months free. Head to jolt.co.uk to get started. This episode is brought to you by Offware. Gym memberships, gift cards, free coffee, and pizza Fridays. Well, these staff perks just don't cut it anymore. That's why OffWork gives your team something they already love—travel! They can book their own flights, pick their own hotels, and plan the perfect getaway, all with the travel fund you set up for them. It's super easy—just set the contributions, and OffWork handles the rest. Better time off means less burnout, more motivation, and happier employees. Give your team a perk they'll actually love. Check out OffWork today on offwork.com.

Welcome to Millennial Masters.

Thank you for having me, Daniel.

So let's start with your entrepreneurial journey, because like many good ideas, yours came on a boozy night out when you were out with your friend in New York, right?

Yes. The first business Design My Night was, was very much that we weren't trying to think of a business, we weren't considering setting up a business. But yeah, the idea for Design My Night came from that, where Andrew, sort of my best friend from university, we were out in New York, and we'd had a few drinks. And lots of things happened that night that then combined to make us think of the idea of Design My Night, the first being the hotel concierge asking like what type of night did we want, what type of area did we want, sort of really drilling down and giving us recommendations. And then there was a website that we then went on that was talking about sort of drinks promotions in that area. And then yeah, on that night out, we were thinking, I think London needs sort of this type of combination, but digitally, and this was back in 2000. And that's how the, the seed of the idea for DMN started.

So it was basically a digital concierge for your night out.

Yeah, that's, that's, that was sort of the first idea. We took it a step further thinking of the idea of price comparison. So especially in London, you can get very expensive drinks and cheaper drinks. And at that time, there were lots of websites like CompareTheMarket and GoCompare, all these price comparison sites coming out. So we thought, what if you could launch a sort of price comparison site for going out in London. And yeah, that was, that was the first iteration of the product.

It was quite a different era. 2009, the iPad didn't even come out. We didn't have an App Store. It came out a year later, but you were still going to go against some big players on the market back then, like OpenTable. How did you drill down on a niche within a niche?

Yeah, there was, there was a few. So there was Time Out, which was more just a big listing site. There was actually one called ViewLondon, which is no longer, but that was a very big listing site. And then yeah, the more booking sites like OpenTable. We wanted to drill in, A, being digitally first, which sounds crazy now, but we were focusing on a sort of millennial market rather than now everyone wants the Gen Z market. And yeah, phone, you know, iPhone was out, people were on their phones. So we wanted people to have an experience that was easy to use on their phones and their laptops. And yeah, we very much focused at the start on the more casual end of the market. So bars, pubs, party bars, whereas OpenTable and the likes of that were more focused on restaurants. So that was the two sort of niches that we were looking at. And then the element of price comparison on top of that was sort of the hook to get people onto the site.

Your background is in marketing and sales. How did you go around the technical side of creating a digital tech product?

So to launch Design My Night, we used an agency. Again, it was serendipitous. So it was at a friend's, I think, engagement drinks. I was just chatting to someone who owned a digital agency. And we'd just come back from New York. And I started talking about the idea. And he said, I'd love to help you on this. I just want to be involved. It'd be great for my portfolio if it becomes something. So we worked with him, he gave us a really good price, and he got it going. And then Our first hire when we raised our first angel round was to bring in someone technical to take on everything.

I wanted to ask you about hires a bit later on, but before that, you mentioned in another podcast that just after 6 months of starting Design My Night, both you and your co-founder quit your jobs. What was the turning point to be able to do that?

So we did it slightly differently. So I quit mine, Andrew stayed at Accenture where he worked, and we actually split his salary for probably another sort of 7 to 8 months. So I went full-time for 6, 7 months while he was still working at Accenture. And then we would just meet up in the evenings and weekends. I think it was two turning points. One, we were getting some traction. So we were trying to do our day jobs. I was at L'Oréal, he was at Accenture, um, and trying to like speak to bar owners and just getting on the street and going and meeting managers and stuff was very difficult while having our job. And actually, my boss at the time at L'Oréal, who's a very good friend of mine now, he pulled me into a side room and said, I can see you're up to something. Just be mindful that in your L'Oréal contract, you can't be setting up another business. And if you do, it might actually be the property of them, because it's on their time. And so he was like, if you are doing something and you're serious about it, either be very careful or take the plunge. So we saw, we saw traffic, we saw the bars and pubs we were speaking to were very interested. I left L'Oréal on very, very good terms, wasn't leaving to a competitor. So I made it clear that if it went wrong, I'd love to come back. And they said, no problem, we'd love to have you back. So I sort of had a buffer, a sort of safety net in case it didn't go right. And then I carried on full-time, got even more traction. And then Andrew and I thought, okay, we're either going to do this or we're not. So then we went.

And in the following years, you scaled Design My Night from just the two of you to almost 100 employees. Now, a lot of the people I've spoken to say that the business becomes a slightly different beast once you go over 50 employees. How did you find that scaling experience? What were the learnings you had from such a huge growth in a relatively quick amount of time? Yeah, it's very tricky.

And don't forget, we were sort of mid-20s ourselves. So we had management experience, management experience, just at our companies, but we were still very young. So I mean, that the first hires, the first like 20 were sort of pivotal. And I sort of look at those as sort of like an iron ring around the founders. So like those first 20, you hope are going to stay for the long haul. You hope they will imbue the culture and desire for Design by Night to win to the rest of the team when, you know, the founder can't be so close to everyone. And so we really nurtured those initial hires. We really hired on personality. You know, did they have the right drive? Did they know, did they want to forge a career almost? So we hired quite junior. And we were like, you know, let's do this together, we will coach you. You know, if you want to do a career in customer success or sales or whatever, do it here. And like, let's be passionate about that job role and be passionate about Design My Night. We were very fortunate with the people we hired early on, 95% stayed right till the end, and they remained that sort of protective layer around us. And then yeah, correctly, as you scale beyond maybe 50, you don't know everyone as personally as you do towards the end. Bizarrely, there were people coming into the office that I didn't even know because I wasn't involved in their hiring and meeting them at the coffee machine. They're like, what do you do? And I'm like, oh, well, I'm the founder. So that is very strange when you sort of lose control of that. But if you set up the culture correctly, and you have a good management structure in place, and you you've got those initial people from day one, the culture can filter through to everyone else.

So what are your learnings from doing so many hirings, either directly yourself or through other people on your team? What are your red flags and your green flags besides personality, as you mentioned just before?

Yes, so hiring, I think we mentioned it, but hiring personality over CV. So I think red flags were people that actually came with what looked like a very good CV, but, you know, had worked at various companies, but then actually they come with very preconceived ideas of their role and a company culture. And actually, I especially preferred at Design My Night to have more of like a blank slate to work with. So we could sort of put our culture and values onto that person. Also, I guess people jumping around jobs a lot. So if I would see on their CV that maybe they only lasted a sort of year at every job, that would be a bit of a red flag to me because we were looking for people for the long term and to grow. Very humble people, even at levels of seniority. I would always look for them to be very humble about what they don't know, how they want to grow, what are the gaps in their knowledge that they want to improve on while working at Design My Night. Um, I don't buy into people just knowing everything. So if I'm on an interview and they just almost feel too polished and too perfect, for me, I feel like I'm not chatting to the genuine person there. So I want really like a genuine person. And, and so it's, it's a word I don't use a lot, but nice. This is not a very descriptive word, but that goes a very, very long way, like hiring people without egos that will fit into the culture that won't upset the apple cart. And it's very difficult to judge that, but I get a sense for people when I start chatting to them. And actually, one story is we hired— actually, I wasn't involved in an engineering hire. Day one, it was Friday, and we had Friday drinks at the office. And I hadn't met him and I was speaking to him. And there was just something really off about him. And he was being quite, quite critical and almost insulting the work that our CTO had done to date., and you know, he was joining his team. And I was like, this is not going to work. And I sort of told the CTO, I was like, I was not sure. And actually, 3 days later, they let him go because the negativity that he was going to put across the team wasn't the type of person that we wanted at Design My Nights. Very, very cultural person fit over, you know, being a top, top, top talent. I think that's the way we looked at it at Design My Nights.

You mentioned the office and remote work.

Wasn't a thing during your Design My Night time, but with your new venture, Trumpet, which we'll, we'll go into it in a little bit, you started at a very different time. What's your take on remote and hybrid working? Does it allow you to hire better talent from around the place, or it could hamper the developing a culture and learning within the business? I think both are true.

I don't think Design My Night would have been successful if we were remote.. So it was such a— I don't like the word family because like a company shouldn't be a family as such. But it was a very tight togetherness, a bond that we were in this together, we would go out a lot together, tight friendships were born at Design My Night, you know, people then ending up living together romantically, non-romantically. And I think when you're remote, I personally think you can only bond so much with someone, like on a more personal level. And then you've got all the learnings, the collaboration. So just being in an office, and my sales team, for example, hearing me on a sales call, you just don't get that now. So yes, you can do recording tools, and they can listen back. But just seeing how I spoke to people, the intonation I use, the tips and tricks I was using, just because they're sat on my bank of desks, I think so valuable. And that goes across all different departments. And also just the time it takes to get stuff done. Now, you're in Slack. And to make one decision, you can see, yeah, and you're chatting. And then I might be on a call, and then I've missed a whole thread. And I come in and disagree with that whole thread. And then it all starts again, versus actually like, come to my desk, let's have a 5-minute chat, and it gets done. So I'm really in favour of like in-person collaboration. But that doesn't mean necessarily that you have to be in the office 5 days a week. I totally understand the benefits of mental health and not having to, in London at least, get on the tube at rush hour, time saved. So I totally get the benefit. And as you alluded to, being able to hire beyond London is important. And in the New Venture trumpet, not everyone is in London, and we've got some great talent around the UK and the world. But I do think that there's something missing when you don't have that in-person collaboration, especially in a startup, you know, when you're working for like a PwC or an Accenture, when that connection is actually less important. But when you are building a startup, the connection of the team and the connection of the team to the founders is so important. And I just don't think you can get that over video calls.

What's the setup for Trumpet, which is also a SaaS business? Which means that is a lot more flexible and technically minded. Yeah, so we, we started fully remote.

And we have since changed. And we've got a really nice office in the London Bridge area in London, I would say 65% of the team are in or around London, we insist that anyone that is in or around London comes in at least on Wednesday, we're starting to find actually that more and more because the office is nice, that more and more people actually want to get out of their flats and houses and actually come into the office. But we insist Wednesday people come into the office, and that has to come from the team leads, of course. And then the one— and then the team we've got around the UK, we try and get them down for a few days, at least like once every 3 weeks. We obviously put them up in hotels, and they collaborate in, in the office together. And then the ones we've got abroad, it's virtual most of the time. And you've just got to be very aware that you need them to feel part of it as well. So we do in-person socials. For every in-person social, we'll also do a virtual social. If we send gifts or thank-yous out to the team, we will also send that out wherever in the world you are. So they have to get the same treatment. From a startup's point of view, it's way more expensive. So I think everyone was like, oh, well, no office, it's remote, it's cheaper. But actually, now we've got an office. And then you have to do in-person socials, virtual socials, send stuff around the world. You have to use tools to do payroll across the world, and which cost a lot of money. On the face of it, it's more efficient, and you can hire people across the globe. But actually, doing in-person and virtual is actually a much bigger cost base for a startup.

Going back to Design My Night, in 2017, you sold the business for 30 million, but you stayed for a further 2 years for an earn-out agreement. How do you get to the point where you decided that the business is ready to be acquired, and how did this earn-out agreement work?

So Andrew and I were very deliberate with the exit of Design My Night. So it was not something we knew that we wanted to work on forever. As I said, we were young when we started it, we sold it in 2017. So that was 7 years of sort of just nonstop work, 24/7, 7 days a week. So it took a toll mentally on us. But we'd also agreed what we wanted out of Design My Night. And it's something a lot of founders don't do when they start. I think a lot of founders just think I want to build a unicorn, because that's what you're told to do in TechCrunch and stuff. But actually, when you decide what you genuinely want out of a business, and for Andrew and I, it was to become financially free. And financially free doesn't mean you need to build a unicorn. If you save as much equity as possible in your business and don't raise a ton of money, actually, you can get a total life-changing exit for, you know, the amount that we sold it for or less.. And you don't have to go and build that unicorn. So Andrew and I sort of worked back from a rough figure of what we wanted to sell it for. And it was less what we originally, what we did sell it for. And we sort of mapped that out over the next sort of 5, 6 years on what ARR we needed to get to, to have a chance of selling it for the value that we wanted, looking at other hospitality multiples of exits. And yeah, we pretty much mapped that ARR and profit out over the 5 years. We tracked that every quarter.. And then when we were probably like 8, 9 months away from hitting that ARR goal, we thought, okay, let's speak to a broker. Let's see what they think about the business. Do they think it could sell for what we want? And at that time, we then weren't the small upstart. So all the great stuff we had done, competitors were copying us with bigger pockets than us. Our secret sauce on why we sold Design My Night was actually the software, not the actual front end website. So we had a reservation software, ticket software. And we totally changed the game in that arena. So a lot of the stuff you see OpenTable, BookATable, those doing now was, was originally our idea. So one example is now when you book a restaurant, you're able to ask for a deposit or your card details. We, we, that was our idea, trying to tackle no shows. So we were the first software to put that into ours. So it became a lot tougher to sort of stand out from the crowd. And all eyes were on us. Rather than us going under the radar. So we just thought, look, 7 years in, we could get the money hopefully that we want. And without raising another ton of money, it might be difficult to stay ahead of the competition. So we just thought that was the right time. And then from engaging the broker, it was probably about an 8-month process to exit. Yeah, we followed a very formal process to exit. We had a few offers on the table at the end, so we were able to negotiate. And the earnout that you mentioned, the extra 2 years was part of that negotiation. So any exit in that multiple, that amount of money, the acquirer is more than likely going to ask the founders to stay, to sort of carry on the business and then hand it over. And it could be anything from 6 months to 5 years. So again, Andrew and I were like, ideally 1, if it was 2, that would be fine. And so as part of our negotiation with our acquirer was the length of the earnout, but also the terms of the earnout. So without getting too technical, the other part of an earnout is a part of your sum, your exit value will be attributed to your earnout. So we got X percent upfront the day we sold, and then the rest was linked to revenue targets over the next 2 years. But there's lots of different ways of tracking that from an acquirer's point of view. It could be based on profit, it could be based on revenue and profit, it could be based on customers, it could be based on churn. And our acquirer had quite a nice, simple metric on revenue. And it was like, if you hit these revenue multiples, we will give you X. And Andrew and I were confident that we would hit those. So that was another reason why we went with their offer versus someone else.

So you were very deliberate in setting up and growing the business in such a way to get it acquired later on down the line, up to 5 years ahead. So that's something everybody tuning in should keep in mind. It doesn't happen overnight. And you also stayed for a further 2 years to ensure the terms of the earnout. Nevertheless, how did it feel to basically leave your business baby?

Yeah, most people think, was it like incredibly tough? I think the good thing about an earnout is, well, when we exited, so on the Friday, which was very surreal and a very proud moment rather than a sad moment, we were in work on Monday, the next day, because we had another 2 years and targets to hit. This sort of allowed us to ease ourselves out of the business. So we were back in on Monday, we couldn't sort of go wild and enjoy all the new fruits of our labor. So life didn't change massively. So we were very head down again, back into the business. And then probably like 6 months out from the end of the earnout, you know, everything was in place, management was in place, we'd handed most stuff over to our acquirers. So I think we were able to come to terms with the handover, ease ourselves out, think about what's next,. And after 2 years of them working for someone else on your own business, you're sort of done anyway, to be honest. So not, not that it's— how was it? But you're like, okay, actually, this is why I started a business. I don't want to work for anyone else. And then suddenly this new acquirer is telling you how to run your own business. So it's almost doubly worse. So by the end, you know, like a year and a half, Andrew and I were like, okay, you've sort of fallen out of love with your baby anyway. So you're like, it's time to let it go. We're excited about what we could do next. And yeah, it allowed us mentally to prepare for having nothing to do with Design My Night.

And when you finished your transition period with Design My Night, the world quickly took a very different turn in 2020. It wasn't what you expected, right?

Yeah, so I think we expected We have, we had other halves at the time and you had two kids. So I think we were both looking forward to just taking a huge break, going super long holidays, um, at least having a year off to just fully relax, have some fun. As I said, we built it through our sort of mid-twenties and onwards. And so we didn't really live our mid to late twenties like most people do. So I think, yeah, you know, help our families and just have, have some fun, relax, downtime. But then obviously, yeah, COVID hit pretty soon after our earnout. So like everyone else, we were sort of locked up in our properties. So that I think, well, it definitely did escalate what we did next. Fortunately and unfortunately, so we didn't take a huge break and we're dealing with all the COVID stuff. So that sort of forced our hand just to sort of crack on and do what was next for us. So next was Trumpet. Yeah, so Trumpet, Andrew and I thought, look, We're sort of early-ish 30s. We're too young not to do anything now. We love building businesses. We love operating. So going again seemed natural, like do what we love. I think we knew we could come at it a bit differently. We knew we didn't have to work ourselves to the bone because we were more mature. We'd learned a lot. We also brought in a third founder for Trumpet to be CEO. So he could become the sort of face of the brand and manage the team and the office and all of that stuff that we didn't really want to do. We, again, we're very deliberate with how we approach Trumpet. We had about 5 or 6 ideas. So we're very good at coming up with ideas, we ideate an idea hard. And I think that's one thing a lot of founders don't do enough. So when we come up with an idea, we don't immediately think of a name and a brand, etc. We give it a project name. So Project X, and then we go out and ideate probably for at least a month or two months. And the mission on ideation for us is to prove to ourselves that it's a terrible idea. So if you go out with the mindset that you're trying to prove that it's a terrible idea, you will ask questions differently, you will approach the topic differently. If you're going out to prove to yourself that it's a great idea, you will spin stuff you will ask the wrong questions, and you will paint too much of a rosy picture for yourself. So we go out to the market, we normally put together a one-pager about the idea. And we'll go on to LinkedIn, use our network, and ask people that we would be selling to be like, hey, I've got this idea. I've got a type— made a little Typeform. It will take you 5 minutes to go through. If you want to jump on a call, great. If you don't, just use the Typeform. And the questions are, it gives an outline and it is like, what do you have that already solves for this? Why won't this work? What don't you like about the idea? And then do you think this does solve a problem? Looking for some positives. And then we take all of that back. We have like a huge sort of notion board of positive, negative, indifferent, and then we assess it. And then we're like, okay, do we think there's an opportunity here? And then the other thing we look at is, are we the right founders for this opportunity? So we had quite, we thought quite a good idea in the fintech space, we ideated it, it got quite positive feedback. But then Andrew and I said, are we the right people to run a fintech business? Like, not, it's not really something I can get that passionate about. So we thought, however hard it is, we're like, no, actually, that's not the right one. But Trumpet was the one out of all the ideas that got, you know, super positive feedback. It suited the time, like post-COVID or during COVID when everything was going digital. And ours is around digital selling. And so it suited the sort of timeframe. So we could jump on that as well. Rory, who became our CEO, we'd known for ages and knew he would be like the perfect third founder because he's like a sales guru. So the sort of stars aligned for Trumpet. And that was the idea that we followed through on.

One quick question. What was the project codename for Trumpet? Good question.

What was it called? It was, I don't know, off the top of my head, it was, I actually think it was originally called Project Loop. Because the initial idea is about keeping everyone in the loop around the sales cycle. So I think, I think we knew we weren't going to call it Loop, but I think we just called it Project Loop. I'm pretty sure it was Project Loop.

Yeah. And then you previously said on another podcast, I was listening to you the other day, sales is the new engineering. Were in the, you said how important sales were for design by Knight, and obviously now you started a SaaS business in the sales area. What, and you also said that your CEO was also very sales-minded. What is something that founders and entrepreneurs get wrong about sales?

Well, I think firstly, I think people look at sales as like a dirty word. I think people look at salespeople, and as I said, it's changing as like the estate agents of SaaS. That you can just find young, ballsy, hungry people, and they'll make great salespeople. Where actually, and it's something I've learned from doing Trumpet and working with Rory, sales is an incredible skill. And not everyone possesses that skill. And it's not just about having the gift of the gab. You know, there is a real psychological skill to selling. It's also a very particular mindset and person that makes a good salesperson. And I don't— and as a founder, you are constantly selling. So you are selling to investors, you are selling to your team, you are selling to customers. When, as an investor, when I'm looking at founders, I think that's a skill that I look for, because I know even if you're technical, when you're an engineer, can they sell as well? And founder-led sales always has to be the start of your business, you have to be the first one to go out and make those first sales, and then bring founders in, you know, now, so from here, we've got a team of 5 salespeople, but they'll still bring us in on larger deals to sort of just seal the deal. So I think, yeah, salespeople are often sort of just not highly regarded and people think, okay, we need to get good tech people in or we need to get good product or designers in and then they think of sales as an afterthought. But as I said, it's a real skill to find the right people. You have to give them time to ramp up. You have to be very decisive with salespeople. If they're not going to work, you have to get rid of them. You haven't got time to waste on bad salespeople and they understand.

How long do you give a salesperson to prove themselves?

Probably, so we ramp them up to target within 3 months and then probably a couple more months after that to see, so our probation period is normally 6 months. So within that, if we think it's not going to happen, it probably won't happen. So it's better to get rid and start again.

One of the key threads in our discussion so far and your story was having a co-founder. And then a third co-founder in your second business. What are your learnings from this business marriage, as many others in the interviews have called it? What should people look for in a co-founder rather than going solo? Are there advantages? Are there disadvantages?

I personally think it's mainly advantages. I don't think I could have done Design My Night or Trumpet by myself. I have huge admiration for founders that go it alone. I just, I just think it's incredibly hard to cover all the bases you need to cover as a founder, and especially at the start before you get to your 50 employees, to do that all by yourself. I just, I just don't know how people do it and do it to a high level. And of course, it is possible. So Andrew and I made the perfect partnership, a, because we were very, very good friends, we trusted each other, I think trust has to be the first building block of a co-founder. Not only trust personally, but trust in each other's skills. So I know that if Andrew is going to go off and do a project about something, he doesn't have to keep sort of signing stuff off with me. I can know he can just do it, and I know it'll be high quality. So you, you can't think you're better than your co-founder, but what you do have to have is obviously complementary sets of skills. So for example, I am more focused on visuals, brand, marketing, sales. Andrew's more focused on sort of product operations, the technical side of things. So we can just let each other get on and then come back together to discuss how things are going. I do get lots of founders asking like, yeah, where do I find a co-founder? And I don't think there is a magic answer to that. A lot of that comes down to networking. There are like things like Entrepreneur First and other programs where you can go in accelerators and meet co-founders. If you do find someone, do not jump into it. Before anything is signed, you need to, I think, spend at least, at least 3 months like dating each other. And literally dating, like going out for drinks, going out for coffees, understanding each other's personalities, understanding each other's drives, understanding family life, understanding what gets them out of bed in the morning, understanding what they want out of the business. Is that the same as you? Understanding what their values are, understanding what type of culture they want to build, All of these things, which you do with a partner as well, you have to get right with your co-founder. It's not just, do you both think it's a great idea? Yes. Because the biggest reason why startups fail, apart from running out of money, is the co-founders split. And they normally split because their cultural values are misaligned rather than product. So yeah, really take your time, even if you're super excited. For example, let's say you're a sales-led founder and you need an engineer, and you find that engineer, and that engineer is brilliant and believes in your idea, and you're so excited. Stop, pause, take the time and see if they are that personal fit as well.

So what lessons have you taken from building and scaling up Design by Night and applied them to starting Trumpet? Because one of the main differences, if I understand correctly, is that you raised VC money and took investment with Trumpet from the beginning.

Yeah, so that was a very different— Design My Night was pretty much bootstrap. And so we only ever raised half a million from angels and took that to exit. And I'm a big advocate of bootstrapping. I guess why we did it differently is one of the main reasons with Trumpet is the scale opportunity. So Trumpet is instantly global, it's got a product-led growth motion, it can grow globally overnight, and people can just sign themselves up to the product. Sales is a very busy space, and it's become even more busy with AI. So we had to move quickly. And it was a much bigger opportunity, like Design My Night had a ceiling of what it could become, really. So all of those facets together, we thought, okay, actually, we need sort of serious money to get this, this going. However, we run the business with a bootstrap mentality, which sometimes winds up on VCs. So, but you know, we haven't just like hired 100 people. And we haven't just spent millions on marketing. Like, we're still very deliberate with everything we do. We'll test with small amounts of money. And we don't just hire the person with the best CV and the biggest salary. So we still have the same thought process. It just allows us to test, I guess, test quicker with money, find more people quicker than we would have when we're bootstrapping. But we still have the same mentality that we're not building a boom or bust cut, you know, we're not thinking, let's spend all the money, raise again, spend all the money, raise again, because that invariably bursts. And I think VCs are seeing that now. So we are still raising, running quickly with Trumpet, but with a sensible mindset of trying to build a sustainable business, which I think all businesses should do. So I think that was a big difference. I think one of the main things I've learned is around focus. You can get very easily distracted by opportunities, especially as a first-time founder. And I think you've just really got to focus in on what's going to drive you revenue, because that's how you're going to raise money if that's what you want to do, even with angels. How can I build a product that builds revenue? And the quickest way to do this is just stay close to your customer. So block out the noise of everything around you, take, take away your ego, just stay very close to your customer and build for your customer in the early stages and just stay very focused on the levers of revenue. And what different things in your business are going to drive revenue and just focus on those. Almost do less experimenting in the early years because you haven't got the cash normally to do it. You know, your partnership opportunities come up and speaking opportunities and all of these things actually don't move the needle, especially in the early years. So I'm very much a believer in get your head down, build a great product, stay close to your customer. And if you are building something that there is a need for, if you do it like that, you'll get to that sort of $500K ARR bracket where you're like, okay, we've got something here. Then you can build on that, maybe raise more money, experiment more, but always try and stay focused, especially as a founder.

I would argue that some of the biggest businesses continue being loss-making for up to a decade before they hit it big. And we're talking here about Facebook, when it was Facebook, We're looking at Uber and even Airbnb, but there seems to be a lot of focus on starting generating revenue early. Does that stop you from becoming a unicorn that takes over the market when you're too focused on generating revenue, especially when we're talking about global scale businesses rather than small scale?

Not generating revenue. So, you know, Uber and alike are doing a lot of revenue, just not profit. So I think it, you can still scale revenue quickly, but you just have to decide that you want to go down that path. I don't— Trumpet could be that, but I don't want to go down that path. I don't want to be a company that doesn't think about profitability at all, and just thinks about, I'm going to spend all this cash I've got, see what happens, raise more, spend— it's such a risky game to play. And that's why there are so few. Like, you know, we talk, you can list your Airbnbs, your Ubers, your Googles, your Facebooks, it seems like there's a lot. But there's, there's not when there's probably millions of startups that have started since Facebook. And you know, there are hundreds that have come on to be these sort of ubiquitous tools that are either worth billions or on the stock market. So you've got to be a very particular type of founder, you've got to make sure that there is a generational type of product that you that you can build. And also to become a unicorn, you don't have to follow that path. You know, you can look at the likes of Canva, for example. Great example. Raised VC, but built a product that people wanted and focused on that and scaled it. And people think they were overnight success. But from what I understand of Canva, you know, it took like sort of 6 years to then find their stride, and then it, and then it took off. Same with Figma, same with Slack to a certain certain case as well. So if, if building a unicorn is what you want to do, and as I said at the top, it's not something that you have to be to be successful, there are other ways of doing it. Don't forget, it's a very risky business in terms of exit, because if you are constantly raising hundreds of millions of dollars, you are diluting yourself, you are handing the power over to the VC. When you're raising hundreds of millions of dollars, there will be terms in those term sheets that are not favorable to the founders unless it becomes a decacorn. And I know personally, people that have IPOs or built a unicorn, and actually the founders have taken less money than I did from Design My Night. If what you want is whether it's generational wealth or just be financially free, you don't have to build a unicorn. If you want to build a generational product that changes the world, like your Ubers and stuff, then yeah, okay, you go down that path. But it's a very different path.

AI is also the new player, and by new player, we're talking about a couple of years, but Is it something you took into account from the beginning when you started Trumpet, or is something that's changing the game in sales and tech development now? How are you looking at implementing it into the product, and how are you using AI personally?

Yeah, so we were aware of AI, and our lead investor, they're called Albion VC, a very AI evergreen fund in London, and they have been been for like 15 years. So they're way ahead of the game on actual like AI, not this new wave of crazy valuations again for just sort of shiny products on top of OpenAI. So A, I think there's going to be a burst coming again. VCs have not learned their lesson clearly. Okay, stupid valuations for AI products that most are going to fail 100%. You know, they really are gambling on that one, one or two winners. I think it's the fundament— the sort of fundamental LLMs your OpenAIs, all of those that will hold all the power. And then obviously the hardware behind that, you know, they say it's the investing in the shovels during like the gold rush, you know, you know, that's what we're seeing, you know, in the, with NVIDIA in the stock market. So I think that yes, true. I think AI is not like Web3 and stuff where I think AI is definitely happening. I think it's definitely going to happen. Agentic AI where agents are going off and just talking to each other and doing tasks for you and coming back. I think that is going to happen. And I'm very excited about it. How I look at it from a business perspective is we've made it very clear with Trumpet that we're not an AI product, but we're going to be AI enabled. And especially in sales, I think there's a lot of elements which can be done with AI. But I'm a big believer in sales, at least that is human to human. When you are doing large deals, if you are selling anything over, say, $50,000 and above, the person taking the bet on buying a software will want to speak to someone. And I, I am doubling down on that. I do not think it will be an AI version of yourself. I just don't. SMBs selling 2 grand, 1 grand, 3, 5 grand deals, yes, like that can probably all be done with AI. So, you know, at Trumpet, we're looking at AI in how can we make our users more efficient? So how can they build— we call them pods in Trumpet, which is our tool, How can they spin up pods quickly, efficiently, and make their life easier? And then on the other side of it, we're thinking about the buyer that interacts with our pods is how can they get the information they want without having to hop on a call with the buyer? So whether that's using AI search on their Intercom or AI search of our pods or asking the market using our AI Copilot, everything they need to know about Trumpet or whatever. There's stuff that can be done async. And that's what we want to help power. But there will always be a human-to-human element, at least in sales. And I do really, really believe that. So, you know, we're staying true to that value at Trumpet. How we personally use it is I'm trying to encourage it more and more across the team. So our engineering team, yes, of course, use AI and AI Copilots with their coding and GitHub and stuff. So very big on that. We use it a lot in marketing as well. So creating video content, imagery, SEO content, So big proponents of AI for that use case as well. We just launched Intercom's AI, Finn, across our customer success. And I think at the moment, about 70% of our support tickets are now answered by AI. So that then human to human allows our CS team to work with our customers on the important stuff. So I'm not looking at just getting rid of a customer support team. I'm looking at still white gloving my customers, but on important stuff. And growing their account versus asking all the standard support tickets that invariably come in. So big proponent of AI for that as well. So yeah, we're looking at it across all elements of our business just to make our business more efficient and hire less people and the people that we hire to focus on the more important tasks.

One of the other things you've done since selling Design My Night, besides starting a whole new business, you've done a lot of angel investing and also became an investor yourself in a range of other the businesses. What type of businesses are you looking at investing in? And is it more about the idea or the founders themselves? So I'm pretty sector agnostic.

I've done about 50 now. I have leaned towards B2B SaaS, like that's what I know. And it's not only what I know, it's I know how easy B2B SaaS is to grow versus other tools like hardware, consumer, etc. B2B SaaS has a playbook, no matter what industry you're focused on. If you are B2B SaaS, there is a sort of sales operations playbook, which I've done, I'm doing again, so I can help my investments with. So I definitely lean towards that. I've got it across telco, I've got it across sports tech, I've got it across sales tech, I've got it across martech. So ad tech I've got as well. So lots of different areas. So I actually quite like learning these different areas. So I don't necessarily have to know the area, I just need to have to understand if it's a problem solution, which leads you on to the other point of is it, is it the product or the founder? It's definitely both. I lean more towards the founder. I do want to see that obviously, there is that problem solution. Once I get my head around that, I have turned down opportunities that I thought were good opportunities, but not the right founder. And so I have said no to investments on that. And I will do that more than the other way around. Because as a founder, you're always pivoting. So Design My Night became successful pretty much because of our software. Software was not in our thinking right at the start. Trumpet, we've already pivoted a few times. So what I look for in a founder is less problem solution, even though obviously I am looking for them to be solving something, is how well do they understand the market they want to operate in. So when they have to pivot, or if something's not going right, they just really understand the market, where it's going, and they really understand their customer. And if they're smart, and they're the right temperament, from what I look for in a founder, then I know they will then pivot to something useful to keep that business going. So I'm definitely looking at that sector knowledge, sector experience, founders that want to stay close to their customers, that really go deep with their customers from the off and understand their pain points. I'm looking for grit and determination, which is very difficult to put your finger on. But I sort of get that sense. When I speak to a founder, I get quite personal with my investments in terms of where they come from. So what in your life has led you to become a founder? Who are you doing this for? And the challenging— the upbringing, the more challenging stories they've had to overcome will probably make them a better founder versus founders that have just been handed everything on a plate since day one. Because when it gets tough, those people invariably fold. Whereas the ones that have been through hardships know what it takes to move forward. So ironically, even though investing in underrepresented founders is low, that's— it's actually exactly what I look for. Normally face something that the middle to upper class white straight male probably hasn't tackled. I'm looking for smarts as well. You just get a sense of someone just if they're smart, if they're switched on, if they're plugged on, as I said, if they understand sales. So yeah, all of those different facets I'm trying to gauge before I invest in a business.

So what type of investor are you, hands-on or hands-off?

I say I'm hands-on, and then I leave it down to the founder. So if the— I prefer if they're coming to me more regularly. I will always give them my number, WhatsApp me, any time of the day. And just be deliberate. I think that's just all I want. So if you've got something very specific you want, just be very clear and ask me and I'll come back with my thoughts. You know, we don't have to hop on an hour call constantly, like just here's my number, tell me what you want. And when I've got, whether it's at midnight, 9 AM on one of my morning walks, when I've got time, I will listen to it. And I will get back to you. So like, I'm very big on just like quick quick async collaboration with my investments. But yeah, really up to the founders. I think it's criminal for founders that don't speak to their investors. You bring on investors because of their knowledge, especially angel investors. So I think it's crazy that you don't use that. So even Trumpet now, we're pretty scaled, pretty big. We've got like 5 different VCs, angel investors. The first of every month, they get an investor update. Update. And if that first is on a Sunday, we will get it to them on a Sunday, the first of every month, they get an investor update. And the first thing I put at the top of that investor update is our asks. If you don't want to read anything else about the business, just, just this is how you can help us. These are the 3 things that you can help us with this month. And we get so much help from that. So I just think it's crazy that founders don't speak to their investors more, keep their investors up to date. Once you've got our money, we can't take it back. Simple as that. So if things aren't going well, that's when you should be leaning on your investors, like for help. So don't shy away from speaking to your investors. Try and be as much of an open book as possible. And then you'll get the best back from them as well.

Great tip there. And I know, even from my own experience, sometimes you shy, you get shy on, on sharing what's not going so well, instead of asking for help. But you also do a popular podcast, Pitch Deck, where you speak to investors as well as entrepreneurs, and you've done almost 70 episodes if my count is right. What have you learned from all those interviews and speaking to so many people?

Yes, I tend to speak with investors, so anyone that invests early stage, so that could be an exited founder, an athlete, a VC, an angel. And on the one hand, it's interesting to see how differently everyone approaches investing, because at the end of the day, investors are just human beings. So one person might be very big on the founder story, someone else might be very big on the market size. So it's very difficult to know that as a founder, on which lever am I pulling when I'm speaking to a potential investor? However, there are very similar common threads that come through. Which is around traction. And I think traction is a very interesting word, because if you're going pre-seed, traction could actually just be how many customers have you spoken to? Like when I was talking about ideating, like that doesn't cost you anything. So if you haven't sold $1 yet of your product, but you come to me with interviews of 100 people you've spoken to, that's traction at pre-seed. And is there intent to buy? How many from those 100? So just again, have you had the smarts to go out and prove that this is going to be a good idea? I think that comes up constantly. And obviously, as we go seed, Series A, traction is obviously ARR, reduced churn, sales velocity, growth, etc. So I think that's very big. Founder, founder staying power, determination, grit. I know it's not very PC to talk about now, but you have to work yourself like a dog at the start. I don't care what anyone says, you cannot get your business off the ground without working incredibly hard. Yes, you need to be aware of your own mental health and take steps to look after your mental health. But if you are not prepared to put in the hours 7 days a week at the start, it's just not going to be successful. I've never seen a super successful entrepreneur that works like 9 to 5, Monday to Friday. It's just not possible. I don't care what anyone says. And you're looking for that. Every, every, every investor I speak to off the record or on the record are looking for that. And the other thing thing that most talk about is, interestingly, a lot like the idea of starting in a niche and then expanding beyond that niche. So especially pre-seed, if a founder comes to you and goes, well, my TAM is 100 billion, and it's this, it's this, it's this, actually what a lot of investors like is, have you found a niche that you are going to get a core group of users that love your product, talk about your product, eulogize about your and spread the word for you, that's super attractive for investors. It's much easier to build product for a niche as well. And then you build out from that niche. But once you find— like Slack started with engineers, it was a communication tool for engineers, and they doubled down on engineers, they built a huge engineering community. That is how they built Slack, and then it spread. So while VCs are looking for that huge TAM, that billion-dollar outcome, especially when you're speaking to angels, pre-seed, dial in on what your niche is, how you're solving for that niche, and then how you'll spread beyond that, that niche in years to come. That comes up a lot as well.

You said, and from my experience as well, hard work 7 days a week, especially at the beginning of a business, is inevitable for a successful startup. So what habits and routines keep you grounded and productive when there's so much to do? But also you have to be wary about not burning out because that could bring the whole business down.

Yeah, so I think you just gotta be very self-aware, which I wasn't in my early days of Design My Night. So be aware when you feel like you might be overwhelmed or you do start to burn out. Like how I sort of counteract that is, um, so every morning I go for a walk without fail, pretty much, uh, normally about an hour. I literally roll out of bed, put a hoodie on and go for a walk. I don't look at my phone during that walk. I think that's important. So I'm listening to music or I'm listening to a podcast or an audiobook. Book, and I'm just walking aimlessly. Just wake your body up, get your mind going. If you wake up, you look at your phone, you look at your Slack messages, and you look at emails, you're on straight away. And it's just not a great way to start the day. So for me, it's walking. Other people, it might be gym, Pilates, yoga, whatever, meditation. I think that's super important, like switch on your body in a nice way in the morning. And then this is where working from home is tough, where an office is good, is setting boundaries. So as I say, like, yeah, you are going to work 7 days a week. But that doesn't mean you have to work every evening as well. So making sure you make time to say, actually, today, and almost put it in your calendar, like laptop shut 6:30. And I'm a big believer in like blocking stuff out in your calendar, whether that be going to the gym or going for a walk. If it's in your calendar, there's some psychological aspect that forces you to do it more. And you know, if, okay, on Tuesdays and Thursdays, my laptop shuts at 6:30 unless there's a fire going on in my business. And make plans, make plans to see your friends, your family. Again, it's something I didn't do at the start of Design My Nights. I was just, I thought, well, if I'm out with my friends for dinner, I should be thinking about the business. And again, that's, that's, you'll burn out quicker. So make time to spend with your loved ones, be outside, exercise, I think they're the main ones that I do. And then because I do lots of things, so podcast, investing, trumpet, again, I block that out in my diary. So I work in sort of 40-minute spurts. And so I will do like a 40-minute spurt and then have like a 20-minute break, which is why I don't really like long meetings either. But I'm like, okay, 40 minutes, I'm going to do these 3 things on my to-do list. Phone is turned over, Slack notifications are off, I'm gonna do my 40-minute burst, burst, then get up, stretch, move away from my laptop. I've got 20 minutes to look at Slack, look at my phone, et cetera, et cetera. Then do another 40-minute burst. It's something very similar called the Pomodoro Technique on like how to stay focused. Great way for learning for exams as well. So I try as much as possible to apply that every day as well.

As we are getting close to wrapping up, I wanna ask you a self-reflective question. That I ask all my interviews. What sacrifices have you had to make to be the Nick that you are today?

Yeah, I think because, as I said, because Design My Night was sort of my mid-20s, I sort of sacrificed like that fun stage, the sort of coming-of-age stage. I'd had university, loved it, sort of came of age at university. But then those 20s where you've got maybe your first job and you're getting a salary for the first time, I definitely sacrificed that sort fun, fancy-free, you know, no responsibilities sort of part of my life, which is regrettable, but I don't regret building Design My Night. Because I think they're actually such great periods in people's lives, you know, your sort of carefree, no responsibility 20s. Definitely that I was very lucky that my, my other half, my friends, my family, in the main, were all very understanding of of the work that I was doing on Design My Night. So I probably wasn't the best friend and son, etc. But they were understanding of that. And I've sort of made up for that since. So again, I'm very deliberate with the relationships I have now with my loved ones and hugely appreciate that as well. And I think that's another thing when, when I speak to founders is like saying, making sure your loved ones and your friends and family are very aware of the journey you're going on, because they are going to have to support you and they're going to have to accept that you're not going to be the best version of yourself with them. So if you can have that support base, it's really important. But yes, it's mainly around that. But the flip of that is I love it. I love building companies. I've loved building Design My Night. I love the financial freedom that that's now given me to have a wonderful 30s, 40s, 50s, and beyond. So yeah, I don't necessarily regret anything. But yeah, obviously just missed out on some things.

And on this positive note, Thank you so much for sharing all this wisdom and insight, Nick. Thanks for having me, Daniel.

I really appreciate it.

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