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Bootstrap Fireside Chats, Part One – Nick Telson, Co-Founder, Design My Night

Nick Telson is a podcaster, investor and entrepreneur who rose to prominence when he founded the iconic nightlife comparison site DesignMyNight (DMN).

He sold the business in November 2017 for £25 million, growing the company to a team of 65 with a site that received over 8 million hits a month, becoming a household name.

DMN began from bootstrapped beginnings, and we are hugely privileged that Nick has agreed to tell us his story and how the seed of an idea in a New York bar grew into one of the most iconic tech businesses in the UK.

Over the course of a two-part interview, we’ll learn about the genesis and growth of DMN, how he and his Co-Founder defied a lack of sector experience to build up a wealth of knowledge and expertise from day one, and the lessons that he has learned that other entrepreneurs can use today.

It’s a conversation jam packed full of insight, learnings and invaluable advice. Here’s part one of the Nick Telson interview.

Please introduce yourself?

I’m Nick Telson, an entrepreneur and investor, and the Founder of Design My Night (DMN), a UK hospitality discovery website helping millions of people a year find great things to do. We founded DMN back in 2011 and grew the business to a successful exit in 2019.

Today, I’m the Co-Founder of Venture investment firm Horseplay Ventures, and also Co-Founder of Trumpet, a tech business creating better buyer journeys and supercharging the sales cycle, more on that later….

Tell us about the genesis of Design My Night?

Before starting DMN I began life in the corporate world. I left university and joined L’Oreal on their marketing grad scheme, working my way up the ladder to marketing manager for one of their professional brands. When I looked ahead at what the future held, my path was going to lead me to becoming GM for one of the L’Oreal brands. A great role, but for me there was a key problem, the higher you go the less marketing you do, so I really began thinking whether I wanted to stay to do less and less marketing or look elsewhere for other opportunities.

At the same time my mate Andrew was at Accenture, and it was on holiday in NYC where we started ideating on DMN over a few frozen margaritas! Back then there was a similar site in NYC which was focused more around drinks offers, and we thought to ourself, they don’t really do that in London, so why not do it ourselves. The idea for DMN grew from there.

Why did you decide to bootstrap your venture, rather than opt to raise investment?

The world was a different place back then in 2010. There were not as many angel investors as there are today, Venture Capital was a very San Francisco connected sector and the notion of raising VC funding was quite alien.

For us, deciding to bootstrap was more a case of not knowing that path existed, and we were both very pragmatic founders who wanted to build a real business, not something that we could just keep fuelling with cash. 

It’s an approach I still bring to my role as an investor today, I like to see some form of traction when looking at a business. Traction doesn’t need to be mass revenue, but you need to see that the founders have gone out and done some thinking, and spoken to potential buyers, not just sat behind a laptop and built the idea out. A lot of founders are very insular.

Then there is the question of how much you’re raising, especially in a tough world like we’re in today. The advice I always give founders if you are looking to raise is raise small. Why raise £1 million when you can raise £100k faster with angels who will be more helpful and involved in your business.

Did you get worried about not having sector experience when you started Design My Night?

Not really because we had got out and done the market research. Before we even wrote a line of code, we had spoken to hundreds of bar owners. Every weekend we were out asking to speak to the manager of a bar we were in, asking what they liked about TimeOut and other similar sites, because we really wanted to understand their pain points. To your question, we did not have any experience in this space, so we had to go and learn as much as we could about the sector.

Tell us about those first few years, how the business grew and some of the top challenges you faced getting the venture off the ground organically?

A central challenge of building a bootstrapped business is that you are the one who has to do everything, we did not have budget to build a big team. That put a lot of pressure on us as founders, having to wear a lot of hats all day every day can be draining. To ease some of that, we relied heavily on interns in the early years, or those from a university course who wanted to work with us for experience. 

What that teaches you though is to upskill and learn to do tasks yourself. For us, digital marketing was an example of this. When we exited DMN the site was getting millions of hits a day, and 65% of those were coming from Google. We were self-taught SEO specialists, and having no choice but to learn that ourselves meant we really threw ourselves in and learnt a skill that was central to our eventual success. We didn’t have to spend on hiring someone to do that either!

At my new start-up Trumpet we have raised investment, so it’s very different. We already have a team of 16 in six months which means I can lean on my strengths and just focus on marketing.

Stay tuned for part two next week….